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full description

invention background

The present invention relates to anionic compounds intended for therapeutic and/or prophylactic use, for administration of an active ingredient or active ingredients to humans or to animals.

Ionic compounds according to the invention in which the main chain consists of polysaccharide units

5 saccharide units comprising carboxyl groups, due to their structure and biocompatibility, are indisputably of interest to the pharmaceutical industry, especially for stabilizing active ingredients, such as proteins.

Polysaccharides and/or oligosaccharides that have the properties of making interactions with active ingredients, eg proteins, are known from International Applications 01 Nos. 8111/111000 and 8101/110000, which are patent applications filed under the name

.Adocia

In these patent applications, polymers or oligomers are defined by their degree of polymerization (DP), which is the average number of repeating units (monomers) in each polymer chain. It is calculated by dividing by 05 the molecular weight. molar mass is the numerical average over the average weight of the repeating unit.It is also defined by the semantic of the chain length distribution, also called the polydispersity

.index (Ip)

Therefore, these polymers are compounds consisting of chains of statistically variable lengths, which are highly rich in potential sites of interaction with protein active components.

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It results in a lack of specific propensity for interaction significance, while a better defined smaller fraction is likely to have a more specific slope in this respect.

Moreover, a polymer chain can interact with different positions on a protein component, but can also, due to the chain's length, interact with several protein components, thus 5 giving rise to the bridging phenomenon. This bridging phenomenon can, for example, produce clumping of proteins or an increase in viscosity. The use of a small molecule with a well-defined main chain makes it possible to minimize these bridging phenomena.

In addition, a molecule with a well-defined main chain is generally more easily traceable (MS/MS mass spectrum, for example) in biological media 01 during pharmacokinetic experiments or administration, distribution, metabolism In comparison with a polymer, elimination generally gives a very diffuse signal with high background noise in the mass spectrum.

In contrast, it is not excluded that for a shorter, well-defined molecule it is likely to display a lack of potential sites of interaction with protein active components.

05 Despite their well-defined structures, the anionic compounds of the invention consist of a main chain consisting of a discrete number U between 0 and 1 (1 ≤ 0 ≥ U) of identical or different saccharide units and also have the property of making reactions with active ingredients, active ingredients proteinuria, for example.

They nevertheless have certain properties with respect to certain active ingredients that make them a candidate of choice81 for pharmaceutical formulations.

The formation of functional groups of these anionic compounds with carboxyl groups advantageously makes it possible to modify the interaction forces involved between the anionic compound and the active ingredient.

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Due to the influence of the specific structure of the main chain, the formation of functionalization groups is easier and more accurate and thus the nature of the obtained anionic compounds is more homogeneous than when the main chain is of a polymeric nature.

General description of the invention

5 Thus, the present invention aims to provide anionic compounds intended for fixation, administration, and delivery of active ingredients, which can be prepared by methods that are relatively easy to implement. Thus, the goal of the current invention is to provide anionic compounds capable of fixing, giving, and delivering a wide variety of active ingredients.

The invention also relates to obtaining anionic compounds that can exhibit biodegradability that are fast and sufficiently suitable for use in the preparation of a broad class of pharmaceutical formulations, including drugs intended for long-term administration and/or many marts. In addition to the requirement for biodegradability that can be modified after administration, the invention aims to provide anionic compounds which comply with the restrictions imposed by the pharmaceutical industry, particularly in terms of persistence under normal conditions of preservation and storage, especially in solution.

05 As will be shown in the examples, anionic substitution compounds of the invention make it possible to prepare solutions that are not turbid in the presence of certain model proteins for formulation, such as lysozyme, which is not possible with certain polymeric compounds, but are nonetheless able to Interaction with model proteins such as albumin. This duplication makes it possible to modify its properties and obtain good formulations candidates for formulation of components

81 Protein activity without the defects shown by some of the compounds mentioned in the previous art.

The invention relates to substituent anionic compounds forming a main chain consisting of a discrete number U between 0 and 1 (1 ≤ 0 ≥ U) of identical or different saccharide units, connected by identical or different glycosidic bonds, the said saccharide units being selected from A group consisting of pentoses and hexoses, uronic acids, and compounds

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N-acetylhexosamines are in a cyclic form or in an open reduced form, and are characterized by their substitution by:

At least one substituted set has the general form I:

I formula –[R1]a–[[Q]–[R2]n]m

5 Substituted sets are identical or different when there are at least two of them, and in which:

If n = zero, then the radical -[Q]- is derived from a C3 carbon-based chain to C15 which is optionally branched or substitutable, optionally unsaturated and/or optionally comprising one or more rings, and/or comprising At least one heterogeneous atom selected from oxygen (O, nitrogen (N), sulfur (S), and one functional group

01 At least L selected from amine or alcohol functional groups, and the said moiety -[Q]- is attached to the main chain of the compound by means of an R1 linker arm linked to it by a T functional group, or directly linked to the main chain by a G functional group,

If 0 = n or 8, then the notch -[Q]- is derived from a C2 to C15 carbon-based chain

which is optionally branched or has substitution, optionally unsaturated and/or optionally includes a ring

05 one or more, and/or comprising at least one inhomogeneity atom selected from N, O, and S,

. At least one functional group L selected from the amine or alcohol functional groups, and delivered

Said mole -[Q]- is attached to the main chain of the compound by means of a linker arm R1 linked to it by a functional group T, or directly linked to the main chain by a functional group G,

The slit -R1- is:

81 Either ligatures then a = zero, and the [Q]- notch is attached directly to the main chain via the functional group G;

or a carbon-based chain C2 to C15, then a = 0 which is optionally substitutable and/or comprising at least one heteroatom selected from the N, O, and S group

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At least one acid function prior to interaction with the -[Q]- moiety, and the aforementioned chain being attached to the -[Q]- moiety, by a functional group T that results from the interaction of the acid function of the R1- acid function of radical- with a functional group An alcohol or amine of the -[Q]- moiety, and the aforementioned moiety R1 is attached to the main chain by a 5-functional group F resulting from the reaction between a hydroxyl functional group or a hydroxyl group

A carboxylic acid functionalization carried by the main chain and a functional group or substituent group carried by the radical-producing substance -R1-;

01

The R2- moiety is a C1 to C30 carbon-based chain which is optionally branched or substitutable, optionally unsaturated, and/or optionally comprising one or more rings and/or one or more selected heterogeneous atoms of N, O, and S, It is with the -[Q]- radical, a functional group Z produced by the reaction between the alcohol, amine or acid functional groups carried by the -[Q]- and R2-producing substances;

F is a functional group selected from the ether, ester, amide, or carbamate functional groups;

05 T is a functional group selected from the amide, or ester, functional groups;

Z is a functional group selected from the ester, carbamate, amide, or ether functional groups;

G is a functional group selected from the ester, amide, or carbamate groups,

n = zero, 0, or 8;

81 0 = m or 8;

The degree of substitution of j, saccharide units, by R1[a-[[Q]-[R2]n]m] varies between 1010 and 6,6 ≤ 1010 ≥ j;

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and optionally one or more substituent groups 1`R-;

The substituent group 1`R- is a C2 to C15 carbon-based chain which has an optional substitution and/or includes at least one heterogeneous atom selected from the N, O, and S and at least one acidic functional group as an alkali metal cation salt, And the chain is linked

5 mentioned in the main chain by a functional group F resulting from the reaction between a hydroxyl functional group or a carboxylic functional group carried by the main chain and a functional group or a substituted group by the substance producing the substituent -1`R;

degree of substitution for polysaccharide units, i, by -1`R, ranging from zero to 6-i ≥ 6-j, j ≤ zero;

01 and if n ≠ is zero and if the main chain does not carry anionic charges before substitution, then i ± zero;

1`R- is identical to or different from -R1-;

The free salifiable acid functions carried by -1`R- are in the form of alkali metal cation salts;

05 `F is a functional group selected from the ether, ester, amide, or carbamate functional groups;

Z, T, F`, F, and G are the same or different,

6. ≤ i+j

In one embodiment, U is between 1 and 1;

In one embodiment, U is between 1 and 5;

81 In one embodiment, 1 = U;

In one embodiment, L is an amine functional group.

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In one embodiment, L is an alcohol functional group.

In one embodiment, it is 6 ≤ 1015 ≥ j.

In one embodiment, it is 1 ≤ 1015 ≥ j.

In one embodiment, it is 1 ≤ 100 ≥ j.

5 In one embodiment, it is 8 ≤ 100 ≥ j.

In one embodiment, it is 005 ≤ 108 ≥ j.

In one embodiment, it is 008 ≤ 101 ≥ j.

In one embodiment, it is 008 ≤ 105 ≥ j.

In one embodiment, 000 ≤ 106 ≥ j.

01 In one embodiment, it is 1 ≤ 1085 ≥ i.

In one embodiment, it is 805 ≤ 105 ≥i.

In one embodiment, it is 8 ≤ 106 ≥ i.

In one embodiment, 005 ≤ 106 ≥i.

In one embodiment, 000 ≤ 106 ≥i.

05 In one embodiment, it is 6 ≤ 101 ≥ i + j.

In one embodiment, it is 6 ≤ 105 ≥ i+ j.

In one embodiment, it is 1 ≤ 105 ≥ i+ j.

In one embodiment, it is 805 ≤ 105 ≥ i + j.

In one embodiment, it is 8 ≤ 0 ≥ i + j.

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In one embodiment, it is 8 = m.

In one embodiment, 0 = m.

In one embodiment, 8 = n.

In one embodiment, 0 = n.

5 In one embodiment, n = zero.

In one embodiment, the anionic compounds of the invention are characterized by the fact that the -[Q]- moiety is derived from alpha-amino acid.

In one embodiment, the anionic compounds of the invention are characterized in that the -[Q]- moiety is derived from alpha-amino acid and n = zero.

01 In one embodiment, the anionic compounds of the invention are characterized as the alpha-amino acid is selected from a group comprising alpha-methylphenylalanine, alpha-methyltyrosine, o-methyltyrosine, alpha-1-phenylglycine. - Hydroxyphenylglycine-4

hydroxyphenylglycine, 1,5-dihydroxyphenylglycine -3,5

05 dihydroxyphenylglycine, as D, L, or racemic

In one embodiment, the anionic compounds of the invention are distinguished in that the alpha-amino acid is selected from natural alpha-amino acids.

In one embodiment, the anionic compounds of the invention are characterized as the natural alpha-amino acid is selected from non-hydrophobic amino acids selected from a group comprising of

81 Tryptophan, leucine, alanine, isoleucine, glycine, phenylalanine, tyrosine, and valine, as L, D, or racemic.

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In one embodiment, the anionic compounds of the invention are characterized as the natural alpha-amino acid is selected from the polar amino acids selected from a group comprising aspartic acid, glutamic acid, lysine, serine, and threonine, in their D, L forms , or the Arismic.

<p>5 In one embodiment, the material producing the moiety -[Q]- is selected from diamines</p>

In one embodiment, the radical-producing material -[Q]- is selected from diamines and is n = 0 or n = 8.

In one embodiment, the diamines are selected from a group consisting of ethylenediamine, lysine, and their derivatives.

01 In one embodiment, the diamines are selected from a group consisting of diethylene glycol diamine

amine diethylene glycol diamine and triethylene glycol diamine.

In one embodiment, the substance producing the -[Q]- moiety is selected from amino alcohols.

In one embodiment, the radical-producing substance -[Q]- is selected from amino alcohols and n = 0 or n = 8.

05 In one embodiment, the amino alcohols are selected from a group consisting of 8-ethanolamine, 2-aminopropanol, ethanolamine, and isopropanolamine.

<p>1 0-isopropanolamine, 3-amino-1,2-propanediol diethanolamine, diisopropanolamine, diisopropanolamine tromethamine (Tris, 8-(8-aminoethoxy) ethanol, 3-amino-1,2-propanediol</p>

.2-(2-aminoethoxy)ethanol 81

In one embodiment, the notch-producing material -[Q]- is selected from dialcohols.

In one embodiment, the crack-producing material -[Q]- is selected from di-alloys and n = 0 or n = 8.

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In one embodiment, di is selected as alcohol from a group consisting of glycerol, diglycerol, and triglycerol.

In one embodiment, dialcohol is triethanolamine

.triethanolamine

5 In one embodiment, the diethylenes are selected from a group consisting of diethylene glycol and triethylene glycol.

In one embodiment, the di-alloys are selected from a group consisting of polyethylene glycols

.polyethylene glycols

In one embodiment, the notch-producing substance -[Q]- is selected from trialcohols.

01 In one embodiment, trialcohol is taryethanolamine

.triethanolamine

In one embodiment, when the -[Q]- moiety is selected from amino acids, the invention relates to substitution anionic compounds that form a main chain consisting of a discrete number U between 0 and 1 (1 ≤ 0 ≥ U) of identical or different, connected polysaccharide units by glycosidic bonds

05 Identical or different, said polysaccharide units are selected from a group consisting of pentoses and hexoses, uronic acids, and N-acetylamines in a cyclic or open reduced form, and are characterized by their substitution by:

At least one substituted set has the general formula II:

II Formula –[R1]a–[[AA]–[R2]n]m 81

Substituted sets are identical or similar when there are at least two substituted sets, and in them:

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If n = zero, then the moiety -[AA]- denotes an amino acid residue comprising a C3 to C15 carbon-based chain linked to the main chain by a functional group `G;

If 0 = n or 8, then the -[AA]- moiety refers to an amino acid residue comprising a C2 to C15 carbon-based chain bearing n -R2 moieties attached to the compound's main chain

5 by an R1 linker arm attached to it via an amide functional group, or directly linked to the main chain via a `G' functional group;

The slit -R1- expresses:

Either ligand then a = zero, and the amino acid residue -[AA]- is attached directly to the main chain via the `G' functional group;

01 or a C2 to C15 carbon-based chain, then a = 0, which has an optional substitution and/or includes at least one heterogeneous atom selected from the S,N,O, at least one acidic functional group prior to the reaction of the amino acid, and the chain It forms an amide functional group with the amino acid residue -[AA]-, and is attached to the main chain by a functional group F resulting from a reaction between a hydroxyl functional group or a functional group

05 A carboxylic acid carried by the main chain and a functional group or substituent group carried by the -R1- moiety-producing substance.

The radical R2- is a C1 to C30 carbon-based chain which is optionally branched or substitutable, optionally unsaturated and/or optionally comprising one or more rings and/or one or more selected heterogeneous atoms of N, O, or S, It forms, together with the building block of an amino acid

81 -[AA]-, functional group `Z resulting from a reaction between a hydroxyl functional group, acidic, or

An amine carried by the R2 moiety- and an acidic, alcohol, or amine-borne functional group by the moiety-producing [AA]-;

F is a functional group selected from the ether, ester, amide, carbamate functional groups;

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`G is a functional group selected from the ester, amide, or carbamate functional groups;

`Z is a functional group selected from the ester, amide, or carbamate functional groups;

n = zero, 0, or 8;

0 = m or 8;

5 The degree of substitution for the cardioid units, j, by R1[a-[[AA]-[R2]n]m]- between 1010 and 6, 6 ≤ 1010 ≥ j;

and optionally one or more substituent groups 1`R-;

The substituent group 1`R- is a C2 to C15 carbon-based chain that has an optional substitution and/or includes at least one heterogeneous atom selected from N, O, and S

01 At least one acidic functional group in the form of an alkali metal cation salt, and the said chain is attached to the main chain by a functional group F resulting from the reaction between a hydroxyl functional group or a carboxylic functional group carried by the main chain and a functional group or a substituted group by the substance Producer of the substituent group -1`R;

05 degree of substitution for polysaccharide units, i, by -1`R, ranging from zero to 6-i ≥ 6-j, j ≤ zero;

If n ≠ is zero and if the main chain does not carry ionic charges before substitution, then i ± zero;

1`R- is identical to or different from -R1-;

81 The free, salt-forming acidic groups carried by -1`R- are in the form of salts of an alkali metal cation;

`F is a functional group selected from the ether, ester, amide, or carbamate functional groups;

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Z, T, F`, F, and G are the same or different,

6. ≤ i+j

In one embodiment, U is between 1 and 1;

In one embodiment, U is between 1 and 5;

5 In one embodiment, 1 = U;

In one embodiment, it is 6 ≤ 1015 ≥ j.

In one embodiment, it is 1 ≤ 1015 ≥ j.

In one embodiment, it is 1 ≤ 100 ≥ j.

In one embodiment, it is 8 ≤ 100 ≥ j.

01 In one embodiment, 005 ≤ 108 ≥ j.

In one embodiment, it is 008 ≤ 101 ≥ j.

In one embodiment, it is 008 ≤ 105 ≥ j.

In one embodiment, 000 ≤ 106 ≥ j.

In one embodiment, it is 1 ≤ 1085 ≥ i.

05 In one embodiment, it is 805 ≤ 105 ≥ i.

In one embodiment, it is 8 ≤ 106 ≥ i.

In one embodiment, 005 ≤ 106 ≥ i.

In one embodiment, it is 000 ≤ 106 ≥ i.

In one embodiment, it is 6 ≤ 101 ≥ i + j.

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In one embodiment, it is 6 ≤ 105 ≥ i + j.

In one embodiment, it is 1 ≤ 105 ≥ i + j.

In one embodiment, it is 805 ≤ 105 ≥ i + j.

In one embodiment, it is 8 ≤ 0 ≥ i + j.

5 In one embodiment, it is 8 = m. In one embodiment, 0 = m. In one embodiment, 8 = n. In one embodiment, 0 = n. In one embodiment, n = zero.

01 In one embodiment, the invention relates to substituted anionic compounds forming a main chain consisting of a discrete number U between 0 and 1 (1 ≤ 0 ≥ U) of identical or different polysaccharide units, connected by identical or different glycosidic bonds, and the said polysaccharide units selected of a group consisting of

of pentose and hexose units, bronic acids, and N-acetylamines in cyclic form or

in an open reduced form, characterized by random substitution by:

05 At least one substituted set has the general formula II:

II Formula –[R1]a–[[AA]–[R2]n]m

Substituted sets are identical or different when there are at least two substituted sets, and in them:

The -[AA]- moiety refers to an amino acid residue that optionally bears n chain-linked R2 moieties.

81 The main of the compound by the R1 link arm, or directly connected to the main chain via the `G' functional group;

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R1- is:

either ligatures then a = zero;

or a carbon-based chain C2 to C15, then a = 0, which has an optional substitution and/or has at least one heterogeneous atom selected from the S,N,O, and at least one 5 acidic functional group prior to the reaction of the amino acid, The said string is formed with the building unit

amino acid -[AA]-, an amide functional group, is attached to the main chain by an F functional group resulting from a reaction between a hydroxyl functional group or a carboxylic functional group carried by the main chain and a functional group or substituent carried by the radical producer -R1-;

01

The radical R2- is a C1 to C30 carbon-based chain which is optionally branched or substitutable, optionally unsaturated and/or optionally comprising one or more rings and/or one or more selected heterogeneous atoms of N, O, or S, It forms, with the amino acid residue AA]-]-, bonds of the type of ester, carbamate, amide, or ether resulting from the reaction between an R2-borne functional group and a functional group carried by the radical producer -[-[AA].

05 F is a functional group selected from the ether, ester, amide, carbamate functional groups;

`G is a functional group selected from the ester, amide, or carbamate functional groups;

`Z is a functional group selected from the ester, amide, or carbamate functional groups;

n = zero, 0, or 8;

0 = m or 8;

81 The degree of substitution for the cardioid units, j, by R1[a-[[AA]-[R2]n]m]- between 1010 and 6, 6 ≤ 1010 ≥ j;

and optionally one or more substituent groups 1`R-;

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R1- is a carbon-based chain which has a selective substitution and/or includes at least one heterogeneous atom selected from N, O, and S, and at least one acidic functional group as an alkali metal cation salt, and said chain is attached to the main chain By means of the `F functional group resulting from the reaction between a hydroxyl functional group or an acid functional group

5 A carboxyl carried by the main chain and a functional group carried by the -1`R-producing substance;

substitution degree i, by -1`R, varies between 0 and 6-i ≥ j-6, j ≤ zero;

and if n ≠ is zero and if the main chain does not carry any ionic charges before substitution, then i ≠ is zero;

01 1`R is identical or different from -R1-;

The free, salt-formable acidic functional groups carried by R1, are in the form of salts of an alkali metal cation;

`F is an ether, ester, amide, or carbamate functional group;

F and `F are identical or different;

05 6 ≤ j + i;

In one embodiment, U is between 1 and 5.

In one embodiment, 1 = U;

In one embodiment, it is 6 ≤ 1015 ≥ j.

In one embodiment, it is 1 ≤ 1015 ≥ j.

81 In one embodiment, it is 1 ≤ 100 ≥ j.

In one embodiment, it is 8 ≤ 100 ≥ j.

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In one embodiment, 005 ≤ 108 ≥ j.

In one embodiment, it is 008 ≤ 101 ≥ j.

In one embodiment, it is 008 ≤ 105 ≥ j.

In one embodiment, 000 ≤ 106 ≥ j.

5 In one embodiment, it is 1 ≤ 1085 ≥ i.

In one embodiment, it is 805 ≤ 105 ≥ i.

In one embodiment, it is 8 ≤ 106 ≥ i.

In one embodiment, 005 ≤ 106 ≥ i.

In one embodiment, it is 000 ≤ 106 ≥ i.

01 In one embodiment, it is 6 ≤ 101 ≥ i + j.

In one embodiment, it is 6 ≤ 105 ≥ i + j.

In one embodiment, it is 1 ≤ 105 ≥ i + j.

In one embodiment, it is 805 ≤ 105 ≥ i + j.

In one embodiment, it is 8 ≤ 0 ≥ i + j.

05 In one embodiment, it is 8 = m.

In one embodiment, 0 = m.

In one embodiment, 8 = n.

In one embodiment, 0 = n.

In one embodiment, n = zero.

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In an embodiment, the substituted anionic compound is selected from the substituted anionic compounds, in isolated form or as a mixture that forms a main chain consisting of a discrete number U between 0 and 1 (1 ≤ 0 ≥ U) of identical or different saccharide units, connected by By identical or different glycosidic bonds, the said polysaccharide units are selected from a group consisting of pentose units.

5 Hexose, bronic acids, and N-acetylamines are in cyclic or open reduced form, and are characterized by their substitution by:

At least one substituted set has the form V:

V Formula –[R1]a–[AA]m

Substituted sets are identical or different when there are at least two substituted sets, 01 and in which:

The moiety -[AA]- indicates an amino acid residue;

The slit -R1- expresses:

Either ligand then a = zero, and the amino acid residue -[AA]- is directly attached to the main chain via the Ga functional group;

05 or a C2 to C15 carbon-based chain, then a = 0, which has a selective substitution and/or has at least one heterogeneous atom selected from N, O, and S and at least one acidic group before reacting with the amino acid, and said chain forms With the amino acid residue -[AA]- an amide functional group, it is attached to the main chain by a Fa functional group resulting from the reaction between a hydroxyl functional group carried by the main chain and a Fa functional group.

81 A functional or substituent group carried by the -R1-producing material;

Fa is a functional group selected from the ether, ester, or carbamate functional groups;

Ga is a carbamate functional group;

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0 = m or 8;

The degree of substitution of polysaccharide units, j, by R1[a-[AA]m]- is strictly greater than zero and less than or equal to 6, 6 ≤ j &lt; zero;

Optionally, one or more substituent groups 1`R-;

<p>5 The substituent group R1- is a carbon-based chain that has a selective substitution and/or includes at least one heterogeneous atom selected from N, O, and S, and at least one acidic functional group as an alkali metal cation salt, and the said chain is linked to the main chain via a functional group F`a resulting from the reaction between a hydroxyl functional group or a carboxylic acid functional group carried by the main chain and a functional group carried by 01 the substance producing 1`R-;</p>

F`a is an ether, ester, or carbamate functional group;

The degree of substitution of polysaccharide units, i, by -1`R, varies between 0 and ≥6 i ≥ j-6, j 0,

Fa and F`a are the same or different;

05 Fa and Ga are the same or different;

<p>6 ≤ j + i;</p>

<p>1 `R- is identical or different from -R1-;</p>

The free, salt-formable acidic functional groups carried by the substituent group -1`R are in the form of salts of an alkali metal cation;

<p>81 The same or different glycosidic bonds mentioned are chosen from a group consisting of (0, 0), (0, 8), (0, 1), (0, 1), or (0, 6), in An alpha or beta geometric image.</p>

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In one embodiment, the anionic compounds of the invention are characterized in that the [AA]- moiety is derived from alpha-amino acid and n = zero.

In one embodiment, the anionic compounds of the invention are characterized as the alpha amino acid is selected from a group comprising alpha-methylphenylalanine.

<p>5 methylphenylalanine, alpha-o-methyltyrosine, alpha-methyltyrosine-O-methyltyrosine, alpha-1-phenylglycine, alpha-phenylglycine 4-hydroxyphenylglycine, and 1,5-dihydroxyphenylglycine-3,5</p>

dihydroxyphenylglycine, in its D, L, or L-arsenic forms.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the alpha-amino acid is selected from the natural 10 alpha-amino acids.

In one embodiment, the anionic compounds of the invention are characterized as the natural alpha-amino acid is selected from non-hydrophilic amino acids selected from a group comprising tryptophan, leucine, leucine alanine, isoleucine, glycine, phenylalanine, tyrosine, and valine, in its D, L, or Arctic forms.

05 In one embodiment, the anionic compounds of the invention are characterized by the natural alpha-amino acid being selected from selected polar amino acids from a group comprising aspartic acid, glutamic acid, lysine, serine, and threonine, in their D, L, or L-arramine forms. .

In one embodiment, the ionic substitution compounds are distinguished by being selected from the 81 substituent ionic compounds of the formula I, II, or V and where a = zero.

In one embodiment, the anionic substitutions are distinguished by being selected from the substituted anionic compounds of formula I, in which G is an ester functional group.

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In one embodiment, the anionic substituent compounds are distinguished by being selected from the substituted anionic compounds of formula I, in which G is an amide functional group.

In one embodiment, anionic substituted compounds are characterized by being selected from the substituted anionic compounds of formula I, in which G is a carbamate functional group.

5 In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula II, in which `G is an ester functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula II, in which `G is an amide functional group.

In one embodiment, the substituted anionic compounds are characterized as being selected from the 01 substituted anionic compounds of formula II, in which `G is a carbamate functional group.

In one embodiment, the anionic substituent compounds are distinguished by being selected from the substituted anionic compounds of the formula I, II, or V in which a = 0.

In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula I, or II, in which F is an ether functional group.

05 In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula I, or II, in which F is an ester functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II, in which F is an amide functional group.

In one embodiment, the ionic compounds that have the substitution are distinguished by being selected from the anionic compounds

81 which has a substitution of formula I, or II, and in which F is a carbamate functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula V, in which Fa is an ether functional group.

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In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula V, in which Fa is an ester functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula V, in which Fa is a carbamate functional group.

5 In one embodiment, the anionic substitution compounds are distinguished by being selected from the substituted anionic compounds of formula I, in which T is an amide functional group.

In one embodiment, the anionic substitution compounds are distinguished by being selected from the substituted anionic compounds of formula I, in which T is an ester functional group.

In one embodiment, the ionic compounds that have the substitution are distinguished by being selected from the anionic compounds

01 which has a substitution of formula I, in which T is an amide functional group, and F is an ether functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, in which T is an amide functional group, and F is an ester functional group.

05 In one embodiment, the anionic substitution compounds are characterized by being selected from the substituted anionic compounds of formula I, in which T is an amide functional group, and F is a carbamate functional group.

In one embodiment, the anionic substituent compounds are characterized by being selected from the substituted anionic compounds of formula I, in which T is an amide functional group, and F is an amide functional group 81.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, in which T is an ester functional group, and F is an ether functional group.

٥٤٤٣

-٢٤-

In one embodiment, the anionic substituent compounds are characterized by being selected from the substituted anionic compounds of formula I, in which T is an ester functional group, and F is an ester functional group.

In one embodiment, the ionic compounds that have the substitution are distinguished by being selected from the anionic compounds

5 which has a substitution of formula I, in which T is an ester functional group, and F is a carbamate functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, in which T is an ester functional group, and F is an amide functional group.

01 In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula I, or II and in which `F is an ether functional group.

In one embodiment, anionic substituted compounds are distinguished by being selected from substituted anionic compounds of formula I, or II and in which `F is an ester functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the 05 substitution anionic compounds of formula I, or II and in which `F is an amide functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II and in which `F is a carbamate functional group.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II in which Fa is an ether functional group.

81 In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II in which Fa is a carbamate functional group.

٥٤٤٣

-٢٥-

In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula I, or II in which F`a is an ether functional group.

In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula I, or II in which F`a is an ester functional group.

5 In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II in which F`a is a carbamate functional group.

In one embodiment, the substituted anionic compounds are distinguished by being selected from the substituted anionic compounds of formula I, or II in which F and F` are identical.

In one embodiment, the substituted anionic compounds are characterized as being selected from the 01 substituted anionic compounds of formula I, or II in which the F and F are ether functional groups.

In one embodiment, anionic substituted compounds are distinguished by being selected from substituted anionic compounds of formula I, or II in which the F and `F are ester functional groups.

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II in which the F and `F are amide functional groups.

05 In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds of formula I, or II in which the F and F' are carbamate functional groups.

In one embodiment, the substituted anionic compounds are characterized as being selected from the substituted anionic compounds of formula II, I, or V in which, when the -R1- moiety is a carbon-based chain, it optionally includes a heterogeneous atom selected from a group made up of N,O,

81 and S.

٥٤٤٣

-٢٦-

In one embodiment, the substituted anionic compounds are characterized by being selected from the substituted anionic compounds by substituted groups of formula A, A, or L and in which the —[R—] moiety is chosen from the following 7 formulas:

Ha R,

R2 Flame E Ri

R Rj

IV form

And in it:

e 0 and t which are identical or different and greater than, equal to, or less than or equal to 12;

R4, R3, R3, and R4 which are identical or different, chosen from a group consisting of a hydrogen atom, linear, saturated or unsaturated, branched or cyclic 6-Cl alkyl alkyl, benzyl C7-O, benzyl alkyl - aryl, optionally comprising heterogeneous atoms selected from a group consisting of 0, N, and/or 5, or functional groups selected from group 0 1 consisting of a carboxylic acid, an amine, an alcohol, or a thiol.

In one embodiment, substituent anionic compounds are characterized by being selected from substituent anionic compounds by substitutions having the formula A, A, I and having the moiety — [R — before connecting to the moiety — [AA] — or to the radical —[Q]— the expression About CH2-C00H-, and after the connection is -CH2-.

5 1 In one embodiment, substituent anionic compounds are characterized by being selected from substituent anionic compounds by substituents having the formula A, A, I and having the moiety — [R — before the linkage to the moiety — [AA] — or to the radical — [Q] — is a C2 to CIO carbon-based chain bearing a carboxylic acid group, and after connection it is a C2 to CIO carbon-based chain.

٥٤٤٣

-٢٧-

In one embodiment, the substituted anionic compounds are characterized as being selected from the anionic compounds that are substituted by substitutions of formula II, I, or V and in which the -R1- moiety is attached to the -[AA]- or to the -[Q]-terminus From a C2 to C10 carbon-based chain bearing a carboxylic acid group, and after connection it is a C2 to C10 carbon-based chain.

5 In one embodiment, the substituted anionic compounds are characterized as being selected from the anionic compounds that are substituted by substitutions of formula II, I, or V and in which the -R1- moiety is attached to the -[AA]- or to the -[Q]-terminus From a C2 to C5 carbon-based chain bearing a carboxylic acid group, and after connection it is a C2 to C5 carbon-based chain.

In one embodiment, the ionic compounds that have the substitution are characterized as being selected from among the compounds

01 Anionic substitution by substituents of formula II, I, or V and having the -R1- moiety before

Connection to the moiety -[AA]- or to the moiety -[Q]- is a C2 to C5 carbon-based chain bearing

For a carboxylic acid group, after the connection is a C2 to C5 carbon-based chain.

In one embodiment, substituent anionic compounds are characterized by being selected from anionic compounds substituted by substitutions of formula II, I, or V and having the -R1- moiety before

05 Connection to the notch -[AA]- or to the notch -[Q]-, chosen from the following groups, in which the connection position is represented by F:

<img file="SA5443B1_D0001.tif" />

or its salts of alkali metal cations selected from a group consisting of sodium ion Na + or potassium ion K +.

٥٤٤٣

In one embodiment, the substituent anionic compounds are characterized by being selected from the substituted anionic compounds by substituents having the formula A, A, I and having the -RI- moiety before connecting to the -[AA]- or to the -[Q]- moiety, being Derived from citric acid.

In one embodiment, anionic compounds with a substitution are characterized as being selected from among the compounds

The anionic e substituents have the formula A, 11, or V and have the -RI- moiety before

The moiety -[AA]- or moiety -[Q]-, is derived from malic acid.

In one embodiment, anionic compounds with a substitution are characterized as being selected from among the compounds

Anionic substitutions of formulas A, A, or 7 do not have a substituted group.

.-R'l-

0 1 In one embodiment, anionic compounds with substitution are characterized as being selected from among the compounds

An ionic substitution by substituents has the formula A, A, or 7, and in which when

The substituent group 1 R- is a carbon-based chain, optionally comprising a heterogeneous atom selected from a group consisting of 0, no, and c.

In one embodiment, anionic compounds with a substitution are characterized as being selected from among the compounds

15 anionic substituents having the formula A, A, or 7, and in which when they are

The substituent group 1 R- is chosen from the fractions having the following formulas:

•T 3

ο0ω5Η-)— R2 2b,b = ^Ri

The IV form is the . form

In an embodiment, the substituent compounds are characterized as being selected from the anionic compounds that are substituted by substituent groups of formula A, A, or 7 in which the substituted group is

-R'l is for CH2C00H-.

٥٤٤٣

-٢٩-

In one embodiment, the substituted anionic compounds are characterized as being selected from the anionic compounds that are substituted by substitutions of formula II, I, or V and in which the -R1- moiety is attached to the -[AA]- or to the -[Q]-terminus From a C2 to C10 carbon-based chain bearing a carboxylic acid group, and after connection it is a C2 to C10 carbon-based chain.

5 In one embodiment, the substituted anionic compounds are characterized as being selected from the anionic compounds that are substituted by substitutions of formula II, I, or V and in which the -R1- moiety is attached to the -[AA]- or to the -[Q]-terminus From a C2 to C10 carbon-based chain bearing a carboxylic acid group, and after connection it is a C2 to C10 carbon-based chain.

In one embodiment, the ionic compounds that have the substitution are characterized as being selected from among the compounds

01 Anionic substitution by substituents of formula II, I, or V and having the -R1- moiety before

Connection to the moiety -[AA]- or to the moiety -[Q]- is a C2 to C5 carbon-based chain bearing

For a carboxylic acid group, after the connection is a C2 to C5 carbon-based chain.

In one embodiment, the substituted anionic compounds are characterized as being selected from the anionic compounds substituted by substitutions of formula II, I, or V and in which the -R1- moiety before 05 is attached to the -[AA]- or -[Q]- moiety. It is a C2 to C5 carbon-based chain carrier

For a carboxylic acid group, after the connection is a C2 to C5 carbon-based chain.

In one embodiment, the substituent anionic compounds are characterized as being selected from the anionic compounds substituted by substitutions of formula I, or II, in which -1`R- is chosen from the following groups and in which * represents the position of contact with F:

<img file="SA5443B1_D0002.tif" />

or its salts of selected alkaline metal cations from a group consisting of Na+ or K+.

٥٤٤٣

-٣٠-

In one embodiment, the substituent anionic compounds are characterized by being selected from substituent anionic compounds by substituent groups of the formula V, in which the substituted group 1`R- is selected from the following groups and in which * represents the contact position of Fa:

<img file="SA5443B1_D0003.tif" />

5 or its salts of alkaline metal cations of a group consisting of Na+ or K+.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

Replacement by substituted groups of the form I, II, or V in which the group is derived

Substituted 1`R- by citric acid.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

01 Replacement by substituted groups of the form I, II, or V in which the group is derived

Substituted 1`R- of malic acid.

In one embodiment, the anionic substituent compounds are characterized by being selected from the anionic compounds substituted by substituent groups of formula I, in which Z is an ester functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds of 05 substituted by substituted groups of formula I, in which Z is an amide functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from substituent anionic compounds by substituent groups of formula I, in which Z is a carbamate functional group.

In one embodiment, anionic substituents are distinguished by being selected from substituted anionic compounds by substituent groups of formula II, in which `Z is an ester functional group.

٥٤٤٣

-٣١-

In one embodiment, anionic substituents are distinguished by being selected from substituted anionic compounds by substituent groups of formula II, in which `Z is an amide functional group.

In one embodiment, the substituent anionic compounds are characterized by being selected from the anionic compounds substituted by substituent groups of formula II, in which `Z is a carbamate functional group.

5 In one embodiment, anionic substituents are characterized by being selected from substituted anionic compounds by substituent groups of formula I, in which `Z is an ester functional group, T is an amide functional group, and F is an ether functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from substituted anionic compounds by substituent groups of formula I, in which `Z is an ester functional group, and T is an ester functional group.

01 is an amide functional group, and the F is an ester functional group.

In one embodiment, anionic substituents are characterized by being selected from anionic substituents by substituted groups of formula I, in which `Z is an ester functional group, T is an amide functional group, and F is a carbamate functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

05 Substitution by substituted groups of formula I, in which `Z is an ester functional group, T is an amide functional group, and F is an amide functional group.

In one embodiment, anionic substituted compounds are characterized by being selected from substituted anionic compounds by substituted groups of formula I, in which `Z is an ester functional group, T is an ester functional group, and F is an ether functional group.

81 In one embodiment, anionic substituted compounds are characterized by being selected from substituted anionic compounds by substituted groups of formula I, in which `Z is an ester functional group, T is an ester functional group, and F is an ether functional group.

٥٤٤٣

-٣٢-

In one embodiment, anionic substituent compounds are characterized by being selected from anionic substituted compounds by substituted groups of formula I, in which `Z is an ester functional group, T is an ester functional group, and F is a carbamate functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

5 Substitution by substituted groups of formula I, in which `Z is an ester functional group, T is an ester functional group, and F is an amide functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic substituents by substituted groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is an ether functional group.

01 In one embodiment, the anionic substituent compounds are characterized by being selected from substituent anionic compounds by substituent groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is an ester functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from substituent anionic compounds by substituent groups of formula I, in which Z is an amide functional group, and T is an amide functional group.

05 is an ester functional group, and the F is a carbamate functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds substituted by substituted groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is an amide functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

81 Substitution by substituted groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is an ether functional group.

٥٤٤٣

-٣٣-

In one embodiment, the anionic substituent compounds are characterized by being selected from substituent anionic compounds by substituent groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is an ester functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

5 Substitution by substituted groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is a carbamate functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds substituted by substituted groups of formula I, in which Z is an amide functional group, T is an ester functional group, and F is an amide functional group.

01 In one embodiment, the substituent anionic compounds are characterized by being selected from anionic compounds replaced by substituted groups of formula I, in which Z is a carbamate functional group, T is an amide functional group, and F is an ether functional group.

In one embodiment, the anionic compounds that are replaced are characterized by being selected from anionic compounds that are replaced by substituent groups of formula I, and in which Z is a carbamate functional group,

05 T is an amide functional group, and F is an ester functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds replaced by substituted groups of formula I, in which Z is a carbamate functional group, T is an amide functional group, and F is a carbamate functional group.

In one embodiment, the anionic compounds that have substitution are characterized by being selected from 81 anionic compounds that are substituted by substituted groups of formula I, in which Z is a carbamate functional group,

T is an amide functional group, and F is an amide functional group.

٥٤٤٣

-٣٤-

In one embodiment, anionic substituent compounds are characterized by being selected from anionic substituents by substituted groups of formula I, in which Z is a carbamate functional group, T is an ester functional group, and F is an ether functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

5 Substitution by substituent groups of formula I, in which Z is a carbamate functional group, T is an ester functional group, and F is an ester functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic substituents by substituent groups of formula I, in which Z is a carbamate functional group, T is an ester functional group, and F is a carbamate functional group.

01 In one embodiment, the anionic substituent compounds are characterized by being selected from anionic compounds replaced by substituted groups of formula I, in which Z is a carbamate functional group, T is an ester functional group, and F is an amide functional group.

In one embodiment, the substituent anionic compounds are characterized by being selected from the anionic compounds substituted by substituted groups of formula I, in which G is an ester functional group, and Z 05 is an ester functional group.

In one embodiment, the substituent anionic compounds are characterized by being selected from anionic compounds replaced by substituted groups of formula I, in which G is an amide functional group, and Z is an ester functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

81 Substitution by substituent groups of formula I, in which G is a carbamate functional group, and Z is an ester functional group.

٥٤٤٣

-٣٥-

In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds substituted by substituted groups of formula I, in which G is an ester functional group, and Z is an amide functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

5 Substitution by substituted groups of formula I, in which G is an amide functional group, and Z is an amide functional group.

In one embodiment, the anionic substituent compounds are characterized by being selected from anionic compounds replaced by substituent groups of formula I, in which G is a carbamate functional group, and Z is an amide functional group.

01 In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds replaced by substituted groups of formula I, in which G is an ester functional group, and Z is a carbamate functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from substituent anionic compounds by substituent groups of formula I, in which G is an amide functional group, and Z

05 It is a carbamate functional group.

In one embodiment, the anionic substituent compounds are characterized by being selected from anionic compounds replaced by substituent groups of formula I, in which G is a carbamate functional group, and Z is a carbamate functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

81 Substitution by substituent groups of formula II, in which `G is an ester functional group, and `Z is an ester functional group.

٥٤٤٣

-٣٦-

In one embodiment, anionic substituents are characterized as being selected from substituted anionic compounds by substituent groups of formula II, in which `G is an amide functional group, and `Z is an ester functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

5 Substitution by substituted groups of formula II, in which `G is a carbamate functional group, and `Z is an ester functional group.

In one embodiment, the substituent anionic compounds are characterized by being selected from anionic compounds substituted by substituent groups of formula II, in which `G is an ester functional group, and `Z is an amide functional group.

01 In one embodiment, anionic substituents are distinguished by being selected from substituted anionic compounds by substituent groups of formula II, in which `G is an amide functional group, and `Z is an amide functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from substituted anionic compounds by substituent groups of formula II, in which `G is a functional group

05 carbamate, and `Z is an amide functional group.

In one embodiment, anionic substituents are characterized as being selected from anionic substituents by substituent groups of formula II, in which `G is an ester functional group, and `Z is a carbamate functional group.

In one embodiment, anionic compounds that have a substitution are distinguished by being selected from anionic compounds in them

81 Substitution by substituent groups of formula II, in which `G is an amide functional group, and `Z is a carbamate functional group.

٥٤٤٣

-٣٧-

In one embodiment, the substituent anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II, in which `G is a carbamate functional group, and `Z is a carbamate functional group.

In one embodiment, anionic substituent compounds are characterized by being selected from 5 substituent anionic compounds by substituent groups of formula I or II, in which the R2- radical is a benzyl radical.

In one embodiment, anionic substituent compounds are characterized by being selected from anionic compounds substituted by substituted groups of formula I, or II, and in which the R2- moiety is derived from a non-hydrophobic alcohol.

01 In one embodiment, the anionic compounds of the invention are characterized in that a hydrophobic alcohol is selected from alcohols consisting of a saturated and/or unsaturated, branched, or unbranched alkyl chain comprising 1–01 carbon atoms.

In one embodiment, the anionic compounds of the invention are characterized as the non-hydrophilic alcohol is selected from alcohols consisting of a saturated and/or unsaturated, branched, or unbranched 05 alkyl chain comprising 10-6 carbons.

In one embodiment, the anionic compounds of the invention are characterized in that a hydrophobic alcohol is selected from alcohols consisting of a saturated and/or unsaturated, branched, or unbranched alkyl chain comprising 1–01 carbon atoms.

In one embodiment, the anionic compounds of the invention are characterized as a hydrophobic alcohol of 81 octanol.

In one embodiment, the anionic compounds of the invention are distinguished as the hydrophobic alcohol is 2-ethylbutanol.

٥٤٤٣

-٣٨-

In one embodiment, the anionic compounds of the invention are characterized as the non-hydrophilic alcohol is selected from myristyl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, butyl alcohol, and oleyl alcohol.

In one embodiment, the anionic compounds of the invention are distinguished that the non-hydrophilic alcohol is selected from 5 groups consisting of cholesterol and its derivatives.

In one embodiment, the anionic compounds of the invention are distinguished by the hydrophobic alcohol being cholesterol.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that a hydrophobic alcohol is selected from menthol derivatives.

01 In one embodiment of the invention, the anionic compounds of the invention are distinguished by the fact that the hydrophilic alcohol is a menthol in its racemic form.

In one embodiment of the invention, the anionic compounds of the invention are distinguished by the fact that the hydrophilic alcohol is a D isomer of menthol, the D isomer of menthol.

In one embodiment of the invention, the anionic compounds of the invention are characterized as the hydrophilic alcohol being the L-isomer of menthol.

In one embodiment of the invention, the anionic compounds of the invention are distinguished by the fact that the hydrophilic alcohol is selected from the tocopherols.

In one embodiment, the anionic compounds of the invention are characterized as the tocopherol being alpha tocopherol.

.alpha-tocopherol

81 In one embodiment, the anionic compounds of the invention are characterized as alpha-tocopherol being a racemate of alpha-tocopherol.

٥٤٤٣

-٣٩-

In one embodiment, the anionic compounds of the invention are characterized as tocopherol being a D . isomer

Alpha-tocopherol.

In one embodiment, the anionic compounds of the invention are characterized as tocopherol being an L . isomer

Alpha tocopherol.

5 In one embodiment, the anionic compounds of the invention are distinguished by the fact that a hydrophobic alcohol is selected from aryl-bearing alcohols.

In one embodiment, the anionic compounds of the invention are characterized by the selection of an aryl-carrying alcohol from a group consisting of benzyl alcohol and phenethyl alcohol.

In one embodiment, the substituted anionic compounds are characterized as being selected from the 10 anionic compounds substituted by substituted groups of formula I or II and in which the R2- moiety is derived from a non-hydrophilic acid.

In one embodiment, the anionic compounds are characterized as the hydrophobic acid is selected from the fatty acids.

In one embodiment, anionic compounds are characterized as the fatty acids are selected from a group of 05 of acids consisting of a saturated or unsaturated, branched or unbranched alkyl chain having 6–11 carbon atoms.

In one embodiment, the anionic compounds are characterized as the fatty acids are selected from a group consisting of linear fatty acids.

In one embodiment, anionic compounds are characterized as linear fatty acids being selected from a group of 81 consisting of caproic acid, enanthic acid, capyrlic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, palmitic acid arachidic acid, behenic acid, tricosanoic acid, lignoseric acid

٥٤٤٣

-٤٠-

lignoceric, heptacosanoic acid, octacosanoic acid, and melissic acid

In one embodiment, anionic compounds are characterized as the fatty acids are selected from a group consisting of unsaturated fatty acids.

5 In one embodiment, anionic compounds are characterized as the unsaturated fatty acids are selected from a group consisting of myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, linoleic acid, alpha linoleic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, and docosahexaenoic acid

01 In one embodiment, anionic compounds are characterized as fatty acids are selected from a group consisting of bile acids and their derivatives.

In one embodiment, the anionic compounds are characterized by the bile acids and their derivatives being selected from a group consisting of cholic acid, dehydrocolic acid, deoxycholic acid, and chinodeoxycholic acid.

05 In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = zero, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds

By substituent groups of the form II in which n = row t, and the notch -[AA]- is

81 Building unit of an amino acid.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds

By substituent groups of the form II and in which n = zero, in which the notch is -R1- and the set

٥٤٤٣

-٤١-

The substituent 1`R- is identical or different and is carbon-based chains, and the -[AA]- moiety is a phenylalanine residue.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = zero, in which the -R1- moiety and the group

5 The 1`R-substituted identical or different are carbon-based chains linked to the main chain by an ether functional group, and the -[AA]- moiety is a phenylalanine residue.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = zero, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains linked to the main chain

01 Via a carbamate functional group, the -[AA]- moiety is a phenylalanine residue.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = zero, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains linked to the main chain by An ether functional group, and the -[AA]- moiety is a phenyltryptophan residue

.tryptophan 05

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = zero, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains linked to the main chain by An ether functional group, and the -[AA]- moiety is a leucine residue.

81 In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which n = zero, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains linked to the main chain by An ether functional group, and the -[AA]- moiety is an alpha-phenylglycine residue.

٥٤٤٣

-٤٢-

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = zero, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains linked to the main chain by An ether functional group, and the -[AA]- moiety is a tyrosine residue

.tyrosine 5

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds

By substituted sets of the form II in which n and a = zero.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds

By substituent groups of formula II in which n and a = zero and the -[AA]- moiety is 01 phenylalanine residue linked directly to the main chain via a carbamate functional group.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains.

In one embodiment, anionic compounds are characterized as being selected from the 05 substituted anionic compounds by substituent groups of formula II in which n = 0, in which the -R1- moiety and the group

The substituent 1`R- is identical or different and is a carbon-based chain, and the -[Q]- moiety is a diamine derivative.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the 81 substituent group 1'R- are identical or different and are carbon-based chains, and the - radical is - [Q]-

Derived from diamine, moiety R2- is derived from linear fatty acid.

In one embodiment, anionic compounds are characterized as being selected from the anionic substituents by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains attached to the main chain

٥٤٤٣

-٤٣-

Via an ether functional group, the -[Q]- moiety is a diamine-derived, and the R2- moiety is a linear fatty acid.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the group

5 The 1'R-substituted identical or different are carbon-based chains linked to the main chain by an ether functional group, the -[Q]- moiety is derived from a diamine, and the R2- moiety is a linear fatty acid.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 01'R- are identical or different and are carbon-based chains linked to the main chain of the Through an ether functional group, the -[Q]- moiety is derived from R-ethylenediamine, and the R2- moiety is from dodecanoic acid.

05

81

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = 0, in which the -R1- radical and the substituent group 1`R- are identical or different and are carbon-based chains, and the radical -[ Q]- is derived from a diamine, and the R2- moiety is derived from a non-hydrophilic alcohol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = 0, in which the -R1- radical and the substituent group 1`R- are identical or different and are carbon-based chains, and the radical -[ Q]- is derived from diamine, and the R2- moiety is derived from cholesterol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 1'R- are identical or different and are ether-based chains, and the -[-] radical Q]- is derived from ethylenediamine, and the R2- moiety is derived from cholesterol.

٥٤٤٣

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In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = 0, in which the -R1- radical and the substituent group 1`R- are identical or different and are carbon-based chains, and the -[-] Q]- is derived from an amino alcohol, and the R2- moiety is derived from a linear fatty acid.

5 In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains, linked to the main chain by By an ether functional group, the -[Q]- moiety is derived from an amino alcohol, and the R2- moiety is a linear fatty acid.

01 In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains, linked to the main chain by Through an ether functional group, the -[Q]- moiety is derived from ethanolamine, and the -R2 moiety is derived from a linear fatty acid.

05 In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, in which the -R1- moiety and the substituent group 1`R- are identical or different and are carbon-based chains, linked to the main chain by Through an ether functional group, the -[Q]- moiety is derived from ethanolamine, and the -R2 moiety is derived from dodecanoic acid.

81 In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1'R- are identical and are carbon-based chains.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, and the -R1- moiety and the group

٥٤٤٣

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The substituent 1`R- is identical and is a carbon-based chain, and the R2- moiety is a linear fatty acid derivative.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the 5 substituent group 1'R- are identical and are carbon-based chains linked to the main chain by a functional group An ether, and the R2- moiety is a linear fatty acid derivative.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by a 10 functional group An ether, the -[AA]- moiety is a lysine residue, and the R2- moiety is a linear fatty acid derivative.

In one embodiment, anionic compounds are characterized as being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by 05 functional groups An ether, the -[AA]- moiety is a lysine residue, and the R2- moiety is a derivative of dodecanoic acid.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n, the -R1- moiety and the identical substituent group 1`R- are carbon-based chains, and the R2- moiety derived from an alcohol 81 is not waterproof.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by an ether functional group The R2 radical is derived from a non-hydrophilic alcohol.

٥٤٤٣

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In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by an ether functional group , the -[AA]- moiety is a leucine residue, and the R2-5 moiety is derived from a non-hydrophilic alcohol.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by an ether functional group , moiety -[AA]- is a residue of leucine, and moiety R2-01 is a cholesterol derivative.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by an ether functional group , and the -[AA]- moiety is an aspartic acid residue, and the moiety is

05 R2- Derived from benzyl alcohol.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by an ether functional group , the -[AA]- moiety is a glycine residue, and the 81 R2- moiety is a decanol derivative.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula II in which 0 = n, and the -R1- moiety and the substituent group 1`R- are identical and are carbon-based chains linked to the main chain by

٥٤٤٣

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01

05

81

An ether functional group, the -[AA]- moiety is a phenylalanine residue, and the -R2 moiety is a 1,7-dimethyloctanol derivative.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which 0 = n and a = 0.

In one embodiment, anionic compounds are characterized by being selected from substituent anionic compounds by substituent groups of formula II in which 0 = n and a = zero, and R2 is a carbon-based chain.

In one embodiment, anionic compounds are characterized by being selected from substituted anionic compounds by substituent groups of formula II in which 0 = n and a = zero, and the [AA]- moiety is a phenylalanine residue linked directly to the main chain via an amide functional group. R2 is a carbon-based chain.

In one embodiment, anionic compounds are characterized by being selected from substituted anionic compounds by substituent groups of formula II in which 0 = n and a = 0, and the [AA]- moiety is a phenylalanine residue linked directly to the main chain via an amide functional group R2 is derived from methanol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula I in which n = 8, the -R1- moiety and the acceptor group --1`R are identical and are carbon-based chains.

In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula I in which 8 = n, the -R1- moiety and the acceptor group --1`R being identical and are carbon-based chains linked to the main chain by a functional group An ether and the -[Q]- moiety is a derivative of a diamine conjugated to an amino acid.

٥٤٤٣

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In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula I in which 8 = n, the -R1- moiety and the acceptor group --1`R being identical and are carbon-based chains linked to the main chain by a functional group An ether and the -[Q]- moiety is derived from a diamine conjugated to an amino acid, and is

5 The R2 moiety is coupled to a linear fatty acid.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula I in which 8 = n, and the -R1- moiety and the acceptor group --1`R are identical and are carbon-based chains, and the -[Q] moiety is - Derived from ethylenediamine conjugated to an amino acid and the R2 moiety is derived from a linear fatty acid.

01 In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula I in which 8 = n, the -R1- moiety and the acceptor group --1`R are identical and are carbon-based chains linked to the main chain by a functional group An ether and the -[Q]- moiety is derived from ethylenediamine conjugated to plesine and the R2 moiety is a linear fatty acid derivative.

05 In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula I in which 8 = n, the -R1- moiety and the acceptor group --1`R are identical and are carbon-based chains linked to the main chain by a functional group An ether and the -[Q]- moiety is derived from ethylenediamine conjugated to plesine and the R2 moiety is a derivative of dodecanoic acid.

81 In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula I in which 8 = n, the -R1- moiety and the acceptor group --1`R are identical and are carbon-based chains linked to the main chain by a functional group An ether and the -[Q]- moiety is derived from ethylenediamine conjugated to plesine and the R2 moiety is a derivative of dodecanoic acid.

٥٤٤٣

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In one embodiment, anionic compounds are characterized by being selected from the anionic substituents by substituent groups of formula I in which 8 = n, the -R1- moiety and the acceptor group --1`R are identical and are carbon-based chains linked to the main chain by a functional group An ether and the moiety -[Q]- is derived from ethylenediamine conjugated to lysine

5 The R2 moiety is a derivative of octanoic acid.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by n = 8 substituent groups of formula II, and the -R1- moiety and the acceptor group -1`R- are identical or different and are carbon-based chains.

In one embodiment, the anionic compounds are characterized as being selected from the substituted anionic compounds 01 by substituent groups of formula II in which n = 8, the -R1- moiety and the acceptor group -1`R- are identical or different and are carbon-based chains linked to the main chain of the Through an ether functional group, the R2- moiety is derived from a non-hydrophilic alcohol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by substituent groups of formula II in which n = 8, the -R1- moiety and the group

05 The -1'R-receptor is identical or different and is carbon-based chains linked to the main chain via an ether functional group and the moiety -[AA]- is derived from a non-hydrophilic alcohol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by n = 8 substituent groups of formula II, and the -R1- moiety and the acceptor group -1`R- are identical or different and are carbon-based chains attached to the main chain

81 Via an ether functional group and the moiety -[AA]- is derived from dodecanol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by n = 8 substituent groups of formula II, and the -R1- moiety and the acceptor group -1`R- are identical or different and are carbon-based chains linked to the main chain by An ester functional group and the R2- moiety is derived from a non-hydrophilic alcohol.

٥٤٤٣

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In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by n = 8 substituent groups of formula II, and the -R1- moiety and the acceptor group -1`R- are identical or different and are carbon-based chains linked to the main chain by An ester functional group and the -[AA]- moiety is an aspartic acid residue, 5 and the R2- moiety is derived from a non-hydrophilic alcohol.

In one embodiment, anionic compounds are characterized by being selected from the substituted anionic compounds by n = 8 substituent groups of formula II, and the -R1- moiety and the acceptor group -1`R- are identical or different and are carbon-based chains linked to the main chain by An ester functional group and the -[AA]- moiety is a 01-aspartic acid residue and the R2- moiety is a derivative of dodecanol.

In one embodiment, the substituent anionic compound is in isolated form bearing a substituent group of general formula I, II, or V.

In one embodiment, the substituent anionic compound is in isolated form with two substituent groups of general formula I, II, or V.

05 In one embodiment, the substituent anionic compound is in isolated form bearing three substituent groups of general formula I, II, or V.

In one embodiment, the substituent anionic compound is in isolated form bearing four groups of general formula I, II, or V.

81 In one embodiment, the substituent anionic compound is in isolated form bearing five groups of general formula I, II, or V.

In one embodiment, the substituent anionic compound is in isolated form bearing six groups of general formula I, II, or V.

٥٤٤٣

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In one embodiment, the substituent anionic compound is isolated with one substituent group of general formula I, II, or V per saccharide unit.

In one embodiment, the substituent anionic compound is in isolated form bearing two substituent groups of general formula I, II, or V for each saccharide unit.

5 In one embodiment, the substituent anionic compound is in isolated form bearing three substituent groups of general formula I, II, or V for each disaccharide unit.

In one embodiment, the substituent anionic compound is in isolated form bearing four substituent groups of general formula I, II, or V for each disaccharide unit.

In one embodiment, the anionic compounds of the invention are characterized by at least one polysaccharide unit being in 10 cyclic form.

In one embodiment, the anionic compounds of the invention are characterized as at least one polysaccharide unit being in the open reduced form or the open oxidized form.

In one embodiment, the anionic compounds of the invention are characterized that at least one polysaccharide unit is selected from a group of pentose units.

05 In one embodiment, the anionic compounds of the invention are characterized by the pentose units being selected from a group consisting of arabinose, ribulose, xylulose, lyxose, ribose, xylose, deoxyribose, arbitol, xylitol, arabitol .ribitol

In one embodiment, the anionic compounds of the invention are characterized in that at least one 81 polysaccharide is selected from a group of hexoses.

In one embodiment, the anionic compounds of the invention are characterized by the fact that the hexose units are selected from a group consisting of mannose, glucose, fructose, and fructose,

٥٤٤٣

-٥٢-

tagatose, psicose, galactose, allose, altrose, talose, idose, gulose, fucose, fuculose, rhamnose, mannitol, xylitol, xylitol.

5 In one embodiment, the anionic compounds of the invention are characterized in that at least one polysaccharide unit is selected from a group of uronic acids.

In one embodiment, the anionic compounds of the invention are characterized as uronic acids are selected from a group consisting of glucuronic acid, iduronic acid, galacturonic acid, mucic acid, glucaric acid, and galactonic acid.

In one embodiment, the anionic compounds of the invention are characterized as at least one polysaccharide unit being N-acetylhexosamine.

In one embodiment, the anionic compounds of the invention are characterized as N-acetylglucosamine is selected from a group consisting of N-acetylgalactosamine, N-acetylgalactosamine-acetylglucosamine, and N-acetylmannosamine.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the main chain is composed of a discrete number of U = 0 polysaccharide units.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the polysaccharide unit is selected from a group consisting of hexose units in cyclic or open form.

81 In one embodiment, the anionic compounds of the invention are distinguished by the fact that the unit of the polysaccharide is selected from a group consisting of glucose, mannose, xylitol, or sorbitol.

In one embodiment, the anionic compounds of the invention are characterized by the fact that the polysaccharide unit is selected from a group consisting of fructose or arabinose.

٥٤٤٣

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In one embodiment, the anionic compounds of the invention are characterized as the polysaccharide unit being N-acetylglucosamine.

In one embodiment, the anionic compounds of the invention are characterized as the polysaccharide unit being N-acetylgalactosamine.

5 In one embodiment, the anionic compounds of the invention are characterized by the fact that the polysaccharide unit is selected from a group consisting of uronic acids.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that a unit of the polysaccharide is selected from a group consisting of glucose, mannose, mannitol, xylitol, or sorbitol.

01 In one embodiment, the anionic compounds of the invention are characterized by the fact that the polysaccharide unit is selected from a group consisting of fructose or arabinose.

In one embodiment, the anionic compounds of the invention are characterized by at least one of the disaccharide units being N-acetylglucosamine.

In one embodiment, the anionic compounds of the invention are characterized by that at least one of the 05 polysaccharide units is N-acetylgalactosamine.

In one embodiment, the anionic compounds of the invention are characterized by the main chain being composed of a discrete number of 1 ≤ 8 ≥ U of identical or different polysaccharide units.

In one embodiment, anionic compounds are characterized according to the invention, that identical or different polysaccharide units, which make up the main chain of a discrete number of U ≤ 8 ≤ 1 disaccharide units, are

81 Selected from a group of pentoses in ring form and/or open form.

٥٤٤٣

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In one embodiment, anionic compounds are characterized according to the invention, that identical or different polysaccharides, which make up the main chain of a discrete number of U ≤ 8 ≤ 1 polysaccharide units, are selected from the hexose units in a cyclic and/or open form.

In one embodiment, anionic compounds are characterized according to the invention, that identical or 5 different polysaccharide units, which make up the main chain of a discrete number of U ≤ 8 ≤ 1 polysaccharide units, are selected from a group of uronic lidonic acids in a cyclic form and/or open image.

In one embodiment, anionic compounds are characterized according to the invention, that identical or different polysaccharides, which make up the main chain of a discrete number of U ≤ 8 ≤ 1 polysaccharide units, are selected from the disaccharide units, are selected from a combination of hexose and pentose units.

01 In one embodiment, anionic compounds are characterized according to the invention, that identical or different polysaccharides, which make up the main chain of a discrete number of U ≤ 8 ≤ 1 polysaccharide units, are selected from the polysaccharide units, are selected from a set of hexose units.

In one embodiment, anionic compounds are characterized according to the invention, that identical or different polysaccharide units, which make up the main chain of a discrete number of U ≤ 8 ≤ 1 of the disaccharide units, are selected from the disaccharide units, are selected from a group consisting of glucose and mannose .

In one embodiment, the anionic compounds are characterized according to the invention, being identical or different polysaccharide units, which make up the main chain of a discrete number of U = 8 identical or separate polysaccharide units.

In one embodiment, the anionic compounds are characterized according to the invention, that the polysaccharide units are identical.

81 In one embodiment, the anionic compounds are distinguished according to the invention, that the units of the disaccharides are different.

In one embodiment, the anionic compounds are characterized according to the invention that the polysaccharide units are identical or different and are selected from hexose and/or pentose units and are connected by glycosidic bonds of type (0, 0).

٥٤٤٣

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In one embodiment, the anionic compounds are characterized according to the invention, that the polysaccharide units are identical or different and are selected from hexose and/or pentose units and are connected by glycosidic bonds of type (0, 8).

In one embodiment, the anionic compounds are characterized according to the invention, that the polysaccharides are identical or 5 different and are selected from hexose and/or pentose units and are connected by glycosidic bonds of type (0, 1).

In one embodiment, the anionic compounds are characterized according to the invention that the polysaccharide units are identical or different and are selected from hexose and/or pentose units and are connected by glycosidic bonds of type (0, 1).

01 In one embodiment, the anionic compounds are characterized according to the invention, that the polysaccharide units are identical or different and are selected from hexose and/or pentose units and are connected by glycosidic bonds of type (0, 6).

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain of discrete number U = 8 of identical or different polysaccharide units selected from hexose units connected by 05 by glycosidic bonds of type (0, 0).

In one embodiment, anionic compounds, according to the invention, are characterized as forming a main chain of discrete U = 8 of identical or different polysaccharide units selected from hexose units connected by glycosidic bonds of type (0, 0), and selected from a group consisting of from trehalose

and sucrose.

81 In one embodiment, anionic compounds, according to the invention, are characterized as forming a main chain of discrete U = 8 units of identical or different polysaccharides selected from hexose units connected by glycosidic bonds of type (0, 8).

٥٤٤٣

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In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain consisting of a discrete number U = 8 of identical or different polysaccharide units selected from hexose units connected by type (0, 8) glycosidic bonds that are kojibiose.

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain of 5 discrete U = 8 units of identical or different polysaccharides selected from hexose units connected by (0, 1) glycosidic bonds.

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain consisting of a discrete number U = 8 of identical or different polysaccharide units selected from hexose units connected by glycosidic bonds of type (0, 1) selected from a group consisting of Nigerians

01 nigeriose and laminaribiose.

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain of discrete U = 8 units of identical or different polysaccharides selected from hexose units connected by glycosidic bonds of type (0, 1).

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain of 05 discrete U = 8 units of identical or different polysaccharides selected from hexose units connected by glycosidic bonds of type (0, 1) selected from a set of maltose, lactose, and cellobiose.

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain of discrete U = 8 units of identical or different polysaccharides selected from hexose units connected by 81 glycosidic bonds of type (0, 6).

In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain consisting of a discrete number U = 8 of identical or different polysaccharide units selected from hexose units connected by glycosidic bonds of type (0, 6) selected from a group consisting of Isomaltose

isomaltose, melibiose, and gentiobiose.

٥٤٤٣

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In one embodiment, the anionic compounds, according to the invention, are characterized as forming a main chain of discrete number U = 8 of identical or different polysaccharide units selected from hexose units connected by glycosidic bonds of type (0, 6) being isomaltose.

In one embodiment, the anionic compounds of the invention are characterized as consisting of a main chain of 5 discrete U = 8 polysaccharide units, one in the cyclic form and the other in the open reduced form.

In one embodiment, the anionic compounds of the invention are characterized as consisting of a main chain consisting of a discrete number U=8 of polysaccharide units, one in a cyclic form and the other in an open reduced form, and selected from a group consisting of maltitol and isomaltitol.

01 In one embodiment, the anionic compounds of the invention are characterized by the main chain being composed of a discrete number of 1 ≤ 1 ≥ U of identical or different polysaccharide units.

In one embodiment, the anionic compounds of the invention are characterized that at least one of the identical or different polysaccharide units, which makes up the main chain of a discrete number of 1 ≤ 1 ≥ U of the polysaccharide units, is selected from a group consisting of connected hexose and/or pentose units 05 via identical or different glycosidic bonds.

In one embodiment, the anionic compounds of the invention are characterized that at least one of the identical or different polysaccharide units, which makes up the main chain of a discrete number of 1 ≤ 1 ≥ U of the polysaccharide units, is selected from the hexose and/or topose units and connected by At least one glycosidic bond of type (0, 8).

81 In one embodiment, the anionic compounds of the invention are characterized that at least one of the identical or different polysaccharide units, which makes up the main chain of a discrete number of 1 ≤ 1 ≥ U of the polysaccharide units, is selected from the hexose and/or topose units and connected by At least one glycosidic bond of type (0, 1).

٥٤٤٣

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In one embodiment, the anionic compounds of the invention are characterized that at least one of the identical or different polysaccharide units, which makes up the main chain of a discrete number of 1 ≤ 1 ≥ U of the polysaccharide units, is selected from the hexose and/or topose units and connected by At least one glycosidic bond of type (0, 1).

5 In one embodiment, the anionic compounds of the invention are characterized that at least one of the identical or different polysaccharide units, which makes up the main chain of a discrete number of 1 ≤ 1 ≥ U of the polysaccharide units, is selected from the hexose and/or topose units and connected by At least one glycosidic bond of type (0, 6).

In one embodiment, the anionic compounds of the invention are characterized by the main chain being composed of a discrete number of U = 1 01 of identical or different polysaccharide units.

In one embodiment, the anionic compounds of the invention are characterized as having at least one polysaccharide unit selected from a group consisting of hexose units in cyclic form and at least one polysaccharide unit selected from a group consisting of hexose units in open form.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the units of the three polysaccharides are identical.

05 In one embodiment, the anionic compounds of the invention are distinguished by the fact that two of the three polysaccharide units are identical.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that identical polysaccharide units are selected from the hexose units, two of which are in the cyclic form and one of them is in the open reduced form, and they are connected by glycosidic bonds of type (0/1).

81 In one embodiment, the anionic compounds of the invention are distinguished by the fact that the identical polysaccharide units are selected from the hexose units, two of which are in the cyclic form and one of them is in the open reduced form, and they are connected by glycosidic bonds of the type (0/6).

٥٤٤٣

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In one embodiment, the anionic compounds of the invention are characterized that identical or different polysaccharide units are selected from the hexose units and that the central hexose unit is connected by glycosidic bonds of type (0,8) and by glycosidic bonds of type (0,1).

In one embodiment, the anionic compounds of the invention are characterized as identical or different polysaccharide units

5 Its choice of hexose units and that the central hexose unit is connected by glycosidic bonds of type (0, 1) and through glycosidic bonds of type (0, 1).

In one embodiment, the anionic compounds of the invention are characterized that identical or different polysaccharide units are selected from the hexose units and that the central hexose unit is connected by glycosidic bonds of type (0, 8) and by glycosidic bonds of type (0, 6).

01 In one embodiment, the anionic compounds of the invention are characterized that identical or different polysaccharide units are selected from the hexose units and that the central hexose unit is connected by glycosidic bonds of type (0,8) and by glycosidic bonds of type (0,1).

In one embodiment, the anionic compounds of the invention are characterized that identical or different polysaccharide units are selected from the hexose units and that the central hexose unit is connected by 05 glycosidic bonds of type (0, 1) and by glycosidic bonds of type (0, 6).

In one embodiment, the anionic compounds of the invention are characterized as the main chain being erlose.

In one embodiment, the anionic compounds of the invention are distinguished that the three identical or different polysaccharides are hexose units selected from a group consisting of mannose and glucose.

In one embodiment, the anionic compounds of the invention are characterized as the main chain being maltotriose.

81 In one embodiment, the anionic compounds of the invention are characterized as the main chain being isomaltotriose.

٥٤٤٣

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In one embodiment, the anionic compounds of the invention are characterized by the main chain being composed of a discrete number of U = 1 identical or different polysaccharide units.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the four polysaccharide units are identical.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that three of the four polysaccharide units are 5 identical.

In one embodiment, the anionic compounds of the invention are distinguished that the four polysaccharides are hexose units selected from a group consisting of mannose and glucose.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the main chain is maltotate arrow.

In one embodiment, the anionic compounds of the invention are characterized that identical or different polysaccharide units are selected from the hexose units and that the terminal hexose unit is connected by glycosidic bonds of type (0, 8), and that the other units are connected to each other by glycosidic bonds of type (0, 6).

In one embodiment, the anionic compounds of the invention are characterized by that identical or different polysaccharide units are selected from hexose units and are connected by glycosidic bonds of type (0, 6).

05 In one embodiment, the anionic compounds of the invention are distinguished by the fact that the main chain is made up of a discrete number

5 = U of identical or different polysaccharide units.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the five polysaccharide units are identical.

In one embodiment, the anionic compounds of the invention are characterized as the five disaccharides being hexose units selected from a group consisting of mannose and glucose.

81 In one embodiment, the anionic compounds of the invention are characterized by the fact that identical or different polysaccharide units are selected from hexose units and are linked by glycosidic bonds of type (0, 1).

٥٤٤٣

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In one embodiment, the anionic compounds of the invention are characterized as the main chain being maltopentose

.maltopentaose

In one embodiment, the anionic compounds of the invention are characterized by the main chain being composed of a discrete number of U = 6 different identical polysaccharide units.

5 In one embodiment, the anionic compounds of the invention are distinguished by the fact that the six polysaccharide units are identical.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that identical or different polysaccharide units are selected from hexose units linked by glycosidic bonds of the type (0, 1).

In one embodiment, the anionic compounds of the invention are characterized that identical or different polysaccharide units are selected from hexose units selected from a group of mannose and glucose.

01 In one embodiment, the anionic compounds of the invention are characterized as the main chain being maltohexose.

.maltohexaose

In one embodiment, the anionic compounds of the invention are characterized by the main chain being composed of a discrete number of U = 7 identical or different polysaccharide units.

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the seven polysaccharide units are identical.

05 In one embodiment, the anionic compounds of the invention are characterized by the fact that identical or different polysaccharide units are selected from hexose units and are linked by glycosidic bonds of type (0, 1).

In one embodiment, the anionic compounds of the invention are distinguished that the seven polysaccharides are hexose units selected from a group consisting of mannose and glucose.

In one embodiment, the anionic compounds of the invention are characterized as the main chain being maltoheptose.

<p>81 In one embodiment, the anionic compounds of the invention are distinguished by the fact that the main chain is made up of a discrete number</p>

<p>1 = U of identical or different polysaccharide units.</p>

٥٤٤٣

-٦٢-

In one embodiment, the anionic compounds of the invention are distinguished by the fact that the octahedron units are identical.

In one embodiment, the anionic compounds of the invention are characterized by the fact that identical or different polysaccharide units are selected from hexose units and are linked by glycosidic bonds of type (0, 1).

In one embodiment, the anionic compounds of the invention are characterized by the octahedral units being

5 Hexose is selected from a group consisting of mannose and glucose.

In one embodiment, the anionic compounds of the invention are characterized as the main chain being malto-octose

.maltooctaose

In one embodiment, an anionic compound comprising a discrete number of polysaccharide units is a natural compound.

01 In one embodiment, an anionic compound comprising a discrete number of disaccharide units is a synthetic compound.

In one embodiment, the anionic compounds of the invention are characterized as being obtained by enzymatic degradation of a polysaccharide and then purification.

In one embodiment, the anionic compounds of the invention are characterized as being obtained by chemical degradation of polysaccharides and then purification.

In one embodiment, the anionic compounds of the invention are characterized as being chemically obtained by covalent coupling of molecular-weight precursors

.precursors

In one embodiment, the anionic compounds of the invention are characterized as the main chain being sufforose

.sophorose 81

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is sucrose.

٥٤٤٣

-٦٣-

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is lactulose.

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is maltulose.

5 In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is leucrose.

In one embodiment, the anionic compounds of the invention are characterized by being selected from anionic compounds whose main chain is N-acetyllactosamine.

In one embodiment, the anionic compounds of the invention are characterized as being selected from anionic compounds whose main chain is N-acetylallulactosamine.

In one embodiment, the anionic compounds of the invention are characterized as being selected from anionic compounds whose main chain is rutinose.

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is isomaltulose.

05 In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is fucosyllactose.

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is gentianose.

In one embodiment, the anionic compounds of the invention are characterized as being selected from the 81st anionic compounds of the main series being raffinose.

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is melezitose.

٥٤٤٣

-٦٤-

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is panose.

In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is kestose.

5 In one embodiment, the anionic compounds of the invention are distinguished by being selected from anionic compounds whose main chain is stachyose.

The nomenclature used hereafter and in the examples section is a simplified nomenclature with reference to the substance producing the compounds in which a functional group has been introduced.

In one embodiment, the anionic compound of the invention is sodium maltotriosemethylcarboxylate reacted with L-phenylalanine having i = 001 and 1065 = j.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacting with L-phenylalanine has i = 1065 and 001 = j.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

05 A carboxylate reacting with L-phenylalanine has i = 1015 and j = 1065.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

Reactive carboxylate with L-tryptophan has i = 1065 and 001 = j.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacts with a leucine whose i = 0056 and j = 1010.

81 In one embodiment, the anionic compound of the invention is N-methyl mannitol carboxylate

His-L phenylalanine modified by N-methylcarboxylate mannitol carbamate carbamate

101 = i and 105 = j.

٥٤٤٣

-٦٥-

In one embodiment, the anionic compound of the invention is sodium N-phenylalanine mannitol.

101 = i has sodium N-phenylalaninate mannitol hexacarbamate hexacarbamate

and 601 = j.

In one embodiment, the anionic compound of the invention is sodium methyltriose methyl 5-carboxylate reacted with L-phenylalanine having i = 0085 and j = 101.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacting with L-phenylalanine has i = 101 and j = 1065.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacting with L-phenylalanine has i = 8065 and j = 1065.

01 In one embodiment, the anionic compound of the invention is sodium maltopentose methyl

His-L phenylalanine reacts with sodium maltopentaosemethylcarboxylate carboxylate

001 = i and 1075 = j.

In one embodiment, the anionic compound of the invention is sodium malto-octose methyl carboxylate reacted with L-phenylalanine having i = 001 and j = 1075.

05 In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with cholesteryl leucinate of i = 0076 and j = 1011.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with cholesteryl leucinate of i = 0011 and j = 1080.

81 In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with cholesteryl leucinate of i = 1010 and j = 1080.

٥٤٤٣

-٦٦-

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

Carboxylate reacts with cholesteryl leucinate of i = 0060 and j = 1001.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacts with cholesteryl leucine with i = 0000 and j = 1010.

5 In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with β-benzyl aspartate of i = 0005 and j = 1051.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with dilauryl aspartate of i = 8017 and 1016 = j.

01 In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with 8-[(8-dodecanoyl amino-6-dodecanoyl amino) hexanoyl amino]

2-[(2-dodecanoylamino-6-ethaneamine

dodecanoylamino (hexanoylamino]ethanamine has i = 8058 and 1080 j.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

05 Carboxylate reacted with (8)-N-aminoethyl (dodecanamide-2)-N

aminoethyl)dodecanamide has i = 0017 and 1087 = j.

In one embodiment, the anionic compound of the invention is sodium maltotriose succinate.

8016 = i has dilauryl aspartate interacting with dilauryl aspartate maltotriosesuccinate

and 1010 = j.

81 In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with decanoyl glycinate having i = 0011 and 1080 = j.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with L-leucine of i = 0016, and j = 1051.

٥٤٤٣

-٦٧-

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with cholesteryl aminoethylcarbamate 2 = i = 8015 and 1081 = j.

In one embodiment, the anionic compound of the invention is sodium methyltriose methyl 5-carboxylate reacted with alpha-phenylglycine of i = 0008 and j = 1058.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with 8-[(8-dodecanoyl amino-6-dodecanoyl amino) hexanoyl amino]

2-[(2-octanoylamino-6-ethaneamine

01 octanoylamino (hexanoylamino]ethanamine has 0016 i = and 1081 = j.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacting with L-tyrosine has i = 1011 and j = 1010.

In one embodiment, the anionic compound of the invention is sodium methyl maltotriose.

A carboxylate reacted with 8-aminoethyl dodecanoate having i = 05 0017 and 1087 = j.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with 1,7-dimethyloctanoylphenylalanine 3,7-dimethyloctanoyl phenylalaninate having i = 0085 and 1010 = j.

In one embodiment, the anionic compound of the invention is sodium hyaluronate tetrasaccharide.

methyl reacted with sodium hyaluronate tetrasaccharide 81

phenylalaninate has 1081 = i and 1088 = j.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with 8-[(8-dodecanoyl amino-6-dodecanoyl amino) hexanoyl amino]

٥٤٤٣

-٦٨-

2-[(2-decanoylamino-6-decanoyl-ethaneamine

amino)hexanoylamino]ethanamine has i = 0011 and 1080 = j.

In one embodiment, the anionic compound of the invention is sodium maltotriose methyl carboxylate reacted with 1-N-dodecanoyl-L-lysine ε-N-dodecanoyl-L-lysine having i 5 = 0087 and 1017 = j.

In one embodiment, the anionic compound of the invention is N-phenylalanine, 1, 1, 8, 1, 5, and tetracarbamate tetracarbamate having i = 0 and j = 1.

The invention also relates to processes for the production of substituted anionic compounds, in isolated form or as a mixture, 10 selected from substituted anionic compounds by substituted groups of formula I or II.

. In one embodiment, the ionic compounds that have the selected substitution are distinguished from the ionic compounds that are

It is replaced by substituted groups of the form I or II that it can be obtained by

Random inoculation of the substituent groups on the major polysaccharide chain.

. In one embodiment, the ionic compounds that have the selected substitution are distinguished from the ionic compounds that are

05

It is replaced by substituted groups of the form I or II that it can be obtained by

Grafting of the substituent groups at precise locations on the polysaccharide units by a process that implements the protective/deprotective steps of the alcohol or carboxylic acid groups carried naturally by the main chain. This strategy produces a selection, especially a zonal selection, grafting of the substituting groups onto the main chain. Protective groups include, but are not limited to, those mentioned in the textbook

PGM Wuts, et al., Greene's Protective Groups in Organic Synthesis 81 by

.2007

The main polysaccharide chain can be obtained by hydrolysis of a high-molecular-weight polysaccharide. methods of degrading

٥٤٤٣

-٦٩-

Includes, but is not limited to, chemical degradation and/or enzymatic degradation

.enzymatic degradation

The main polysaccharide chain can also be obtained by forming glycosidic bonds between molecules

oligosaccharide and monosaccharide molecules

5 Using a chemical coupling strategy or an enzymatic pairing strategy.

JT Smooth et al., Advances in Pairing strategies include those mentioned in the publication and in the book, Carbohydrate Chemistry and Biochemistry 2009, 62, 162-236 TK Lindhorst, Essentials of Carbohydrate Chemistry and Scholastic

2007-209, 157 Biochemistry. The coupling reactions can be carried out in a solution on said carrier. The polysaccharide molecules before conjugation can carry groups

Specific substituents and/or can be interacted with a functional set either randomly or selectively domain-selectively coupled with each other.

So, for example, the compounds of the invention can be obtained according to one of the following processes:

random inoculation of the substituent groups on the main polysaccharide chain;

05 one or more steps of inserting a glycosylation group between substituent-bearing monosaccharide or oligosaccharide molecules;

One or more steps of inserting a glycosylation group between one or more monosaccharide or oligosaccharide molecules bearing substituent groups and one or more monosaccharide or oligosaccharide molecules.

one or more steps of introducing protective groups to alcohols or acids naturally carried by the main polysaccharide chain 81, followed by one or more grafting reactions of a substituted group and, finally, a step of removing protective groups;

one or more steps of introducing a glycosylation group between one or more monosaccharide or oligosaccharide molecules bearing protective groups for alcohols or acids carried naturally by a chain

٥٤٤٣

-٧٠-

master polysaccharide, and one or more steps to graft the substituent groups onto the obtained main chain, and then a step to remove the protecting groups;

One or more steps of introducing a glycosylation group between monosaccharide molecules

One or more carrier oligosaccharide or monosaccharide molecules

5 Protecting groups from alcohols or acids carried naturally by the main polysaccharide chain, one or more monosaccharide or oligosaccharide molecules, one or more substituent group grafting steps, and thereafter a step of removing the protecting groups.

The compounds of the invention, isolated or as a mixture, may be separated and/or purified by various methods after they have been obtained, particularly by the above-mentioned processes.

01 It is worth mentioning the chromatography methods, especially the so-called "preparative" methods, such as:

flash chromatography, especially on silica,

HPLC (high performance liquid chromatography) type, especially RP-HPLC or reverse phase 05 HPLC.

Selective precipitation methods can also be used.

The invention also relates to the use of anionic compounds of the invention to prepare pharmaceutical compositions.

The invention also relates to a pharmaceutical composition that includes one of the anionic compounds of the invention as mentioned before and at least one active ingredient.

81 The invention also relates to a pharmaceutical composition characterized by the fact that the active ingredient is selected from a group consisting of

It consists of proteins, glycoproteins, peptides, and nonpeptide therapeutic molecules.

٥٤٤٣

-٧١-

The term “active ingredient” means produced as a single chemical entity and/or as a combination that has a physiological activity. The said active ingredient can be exogenous, i.e.

It is provided by the composition of the invention. It can be endogenous, for example growth factors

which will be secreted into a wound during the first healing phase and which can be kept on the said wound

5 By the combination of innovation.

Depending on the target conditions, they are intended for topical and/or systemic treatment.

In the case of local releases and systemic, the expected modes of administration are by intravenous route, subcutaneous, intradermal, transdermal, intramuscular, oral, nasal, nasal, vaginal, ocular. ocular, buccal, pulmonary,

etc.

Pharmaceutical compositions for the invention are either in liquid form or in an aqueous solution, or as powder, implant, or film. They may also include conventional 05 pharmaceutical excipients that are well known to those skilled in the art.

Depending on the pathological conditions and methods of administration, pharmaceutical formulations may usefully include excipients to be formulated into the form of a gel, sponge, injectable solution, oral solution, or disintegrated oral tablet, etc.

Brief explanation of the drawings

81 Figure 0 shows the mass spectrum.

Detailed description:

The invention also relates to a pharmaceutical composition, which is characterized as being able to be administered in the form of a support, film or coating of an implantable biomaterial, or an implant.

٥٤٤٣

Examples

(A) Preparation of compounds and corresponding examples.

The structural formulas of the compounds of the invention are given in a table. The structural formulas of the corresponding examples are given in Table (2).

5 table (1)

<tr><td><p>group</p><p>LH 1,1106 H</p><p>-R1-[[Q]-</p><p>[R2]n]m</p></td><td><p>Inferred group -</p><p>R'l</p></td><td><p>Alaska Red Series</p></td><td><p>\</p></td><td><p>NS</p></td><td><p>compound</p></td></tr>

Compounds 1 to 6: Rl-[[Q]-[R2]n]m, R'l, R =R

<tr><td><p>2</p></td><td><p>hi</p></td><td><p>rude</p></td><td><p>٠,٦</p><p>p</p></td><td><p>١,٠</p></td><td><p>١</p></td></tr><tr><td></td><td><p>mm 0</p></td><td><p>yhe</p></td><td><p>١,٠</p></td><td><p>٠,٦٥</p></td><td><p>٢</p></td></tr><tr><td><p>circulate</p></td><td><p>How many</p></td><td><p>mmm beware</p></td><td><p>٠,٦</p><p>p</p></td><td><p>٠,٣٥</p></td><td><p>٣</p></td></tr><tr><td></td><td><p>i/Af</p><p>٠</p></td><td><p>Glissie</p></td><td><p>١,٠</p></td><td><p>٠,٦٥</p></td><td><p>٤</p></td></tr><tr><td></td><td><p>hmmm</p><p>O</p></td><td><p>sense</p></td><td><p>٠,٠</p></td><td><p>١,٥٦</p></td><td><p>p</p></td></tr>

٥٤٤٣

-٧٣-

<img file="SA5443B1_D0004.tif" />

<img file="SA5443B1_D0005.tif" />

Compounds 8 to 30: Rl-[[Q]-[R2]n]m, R'l, H =R

<tr><td><p>disappointed</p></td><td><p>NS</p><p>O</p></td><td><p>spell me</p></td><td><p>٠,٤</p></td><td><p>١,٢٥</p></td><td><p>٨</p></td></tr><tr><td><p>trot</p></td><td><p>M1M1A</p><p>O</p></td><td><p>jalihyi</p></td><td><p>0.6 p</p></td><td><p>٠,٨</p></td><td><p>٩</p></td></tr><tr><td></td><td><p>NS</p><p>O</p></td><td><p>sighs</p></td><td><p>0.6 p</p></td><td><p>٢,٦٥</p></td><td><p>١٠</p></td></tr><tr><td></td><td><p>how much</p></td><td></td><td><p>0.7 p</p></td><td><p>١,٠</p></td><td><p>١١</p></td></tr><tr><td><p>٢</p></td><td><p>camra ham</p></td><td></td><td><p>0.6 p</p></td><td><p>١,٠</p></td><td><p>١٢</p></td></tr>

٥٤٤٣

<a name="caption2"></a>

-٧٤-

<tr><td><p>s</p></td><td><p>“Sm? y</p></td><td><p>NS</p></td><td><p>٨</p></td><td><p>١,٧٦</p></td><td><p>١٣</p></td></tr><tr><td><p>tj</p></td><td><p>"why</p></td><td></td><td><p>٠,٢</p><p>٩</p></td><td><p>١,٣٣</p></td><td><p>١٤</p></td></tr><tr><td><p>-NS</p></td><td><p>m 1 m 1 ha</p></td><td><p>I will</p></td><td><p>٠,٢</p><p>٩</p></td><td><p>٣,٠١</p></td><td><p>١٥</p></td></tr><tr><td><p>■'١٠١٠٢!</p></td><td><p>^sa</p><p>O</p></td><td><p>«U9»</p></td><td><p>٠,١</p><p>٤</p></td><td><p>١,٦١</p></td><td><p>١٦</p></td></tr><tr><td><p>drag</p></td><td><p>^sNS</p><p>O</p></td><td><p>Welcome</p></td><td><p>٩</p></td><td><p>١,١١</p></td><td><p>١٧</p></td></tr><tr><td><p>Dunn</p></td><td><p>"Sniff/</p></td><td><p>„</p></td><td><p>٠,٥</p><p>٣</p></td><td><p>١,١٥</p></td><td><p>١٨</p></td></tr><tr><td><p>: ttttt = two</p></td><td><p>NS:</p><p>O</p></td><td></td><td><p>٠,٣</p><p>٦</p></td><td><p>٢,٣٧</p></td><td><p>١٩</p></td></tr><tr><td><p>Dr</p></td><td><p>O</p></td><td><p>0 ah</p></td><td><p>٠,٢</p><p>١</p></td><td><p>٢,٥٢</p></td><td><p>٢٠</p></td></tr><tr><td><p>M 76 m 1'ΆΛΆΆ'■</p></td><td><p>m9</p><p>" a</p></td><td><p>you will greet me</p></td><td><p>٠,٢</p><p>٧</p></td><td><p>١٣٧</p></td><td><p>٢١</p></td></tr><tr><td><p>:humping</p></td><td><p>deaf</p></td><td><p>snobber</p></td><td><p>٠,٤</p><p>١</p></td><td><p>٢,٣٦</p></td><td><p>٢٢</p></td></tr><tr><td></td><td><p>"millimeter;</p></td><td><p>jerky</p></td><td><p>٠,٢</p></td><td><p>١,٤٣</p></td><td><p>٢٣</p></td></tr>

٥٤٤٣

-٧٥-

<tr><td></td><td></td><td></td><td><p>١</p></td><td></td><td></td></tr><tr><td><p>beautiful 0</p></td><td><p>'mm h7</p></td><td></td><td><p>٠,٥</p><p>٨</p></td><td><p>١,٠٦</p></td><td><p>٢٤</p></td></tr><tr><td><p>thubbsds</p></td><td><p>O</p></td><td><p>,question</p></td><td><p>٠,٢</p><p>٨</p></td><td><p>٢,٤٥</p></td><td><p>٢٥</p></td></tr><tr><td><p>shake</p></td><td><p>blood</p></td><td><p>and</p></td><td><p>٠,٥</p><p>٢</p></td><td><p>١,١٢</p></td><td><p>٢٦</p></td></tr><tr><td><p>and</p></td><td></td><td><p>you will let</p></td><td><p>٠,٢</p><p>٨</p></td><td><p>١,٣٦</p></td><td><p>٢٧</p></td></tr><tr><td><p>to reply h</p></td><td><p>• a</p></td><td><p>٠</p></td><td><p>٠,٨</p><p>١</p></td><td><p>٠,٨٣</p></td><td><p>٢٨</p></td></tr><tr><td><p>Ssssammsalm</p></td><td><p>' &amp; m 116.6 n 2</p></td><td><p>repair</p></td><td><p>٠,٢</p><p>٧</p></td><td><p>١٣٧</p></td><td><p>٢٩</p></td></tr><tr><td><p>did not</p></td><td><p>κγ 3</p></td><td><p>I</p></td><td><p>٠,٣</p><p>٩</p></td><td><p>١,٢٥</p></td><td><p>٣٠</p></td></tr>

Compound 31: Q]-fR2][2, R=ONa]

<tr><td><p>y</p></td><td><p>/</p></td><td><p>™, jihadhagat 9</p></td><td><p>٠,٢٢</p></td><td><p>٠,٢٨</p></td><td><p>٣١</p></td></tr>

Compounds 32 to 33: Rl-[[Q]-[R2]n]m, R'l, R=H

٥٤٤٣

-٧٦-

<img file="SA5443B1_D0006.tif" />

<img file="SA5443B1_D0007.tif" />

<tr><td><p>Inferred group</p><p>-Rl-[[AA]-[R2]n]</p></td><td><p>group</p><p>underlining —</p><p>R'l</p></td><td><p>average molecular weight</p><p>My weight (kg/mol)</p></td><td><p>Series</p><p>Alaska Red</p></td><td></td><td></td><td><p>Examples</p><p>midwife</p></td></tr>

Corresponding examples 81, 82, Rl-[[Q]-[R2]n]m, R1l, Β2: RH Bl

<tr><td><p>mm/h</p></td><td><p>"mm h</p></td><td><p>١</p></td><td></td><td><p>p</p></td><td><p>١,٦</p><p>٤</p></td><td><p>81</p></td></tr><tr><td></td><td><p>Ο</p></td><td><p>p</p></td><td></td><td><p>٤</p></td><td><p>١,٦</p></td><td><p>Β2</p></td></tr>

Compound 1: sodium . methyltriose methyl carboxylate

L-phenylalanine L-phenylalanine reacts with maltotriosemethylcarboxylate 5

٥٤٤٣

-٧٧-

106 g (06 mmol) of sodium borohydride was added to 1 g (011 mmol of hydroxyl functional groups) of maltotriose (CarboSynth) dissolved in water at 65° C. After stirring for 11 minutes 81 g were added (811 mmol) of sodium chloroacetate. Then 81 ml was added.

5 Diverter 01p of sodium hydroxide (811) mmol dropwise into this solution and then the mixture was heated at 65°C for 10 min. Then 0606 g (011 mmol) sodium chloroacetate was added to the reaction medium , with 01 mL of a solution of 01P of sodium hydroxide (011 mmol NaOH) drop by drop. After heating for 0 h, the mixture was diluted with water, and neutralized with acetic acid.

01 acetic and then purified by ultrafiltration over a 0 kDa PES polyether sulfone film against water. The concentration of the compound for the final solution was determined by dry extraction, after which an acid/base experiment was conducted in a 51/51 (vol/v) water/acetone mixture in order to determine the degree of substitution by methylcarboxylate.

According to dry extract: [combined] = 1800 mg/g.

05 According to an acid/base experiment, the degree of substitution by methyl carboxylate was 0065/glucoside unit.

The sodium maltotriose methylcarboxylic acid solution was acidified on purolite (anionic) resin to obtain maltotriose methylcarboxylic acid and then freeze-dried for 10 hours.

81 10 g of methyl malto-triose carboxylic acid (61 mmol of methylcarboxylic acid functional groups) was dissolved in Dimethylformamide (DMF) and then cooled to zero. A mixture of 507 ethyl phenylalanine hydrochloride salt was prepared. g hydrochloride, 85 mmol) in dimethylformamide DMF. 805 g of tartethylamine was added

٥٤٤٣

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Triethylamine (85 mmol) was then added to this mixture. A solution of methylmorpholine (601 NMM, 61 mmol) and ethyl chloroformate (601) (EtOCOCl, 61 mmol) was then added to the mixture at 51°C. An ethylphenylalanine solution was added and the mixture was stirred at 10° C. Aqueous imidazole (111 g/L) 5 was added and the mixture was then heated to 11° C. The medium was diluted with water and then the solution was purified

It was obtained by ultrafiltration on a 0 kDa PES membrane against a solution of 100 p NaOH, 100% sodium chloride (NaCl), and water. The concentration of the compound was determined by dry extraction. A sample of the solution was lyophilized and analyzed by 1HNMR in D2O to determine the degree of substitution by methylcarboxylates reacting with phenylalanine.

According to dry extraction: [compound 0] = 8107 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/ glycoside unit was 1065 glycoside.

The degree of substitution by sodium methylcarboxylates/05 was 001 glycoside unit.

Compound 8: Sodium malto terose methyl carboxylate reacted with L-phenylalanine

Using a process similar to that used to prepare compound 0, sodium malto terose methyl carboxylate reacted with phenylalanine was obtained.

According to dry extraction: [compound 8] = 8001 mg/g.

81 According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 001.

The degree of substitution by sodium malto terose methyl carboxylate/glycoside unit was 1065.

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Compound 1: Sodium Malto Tariose Methyl Carboxylate Reacting With L-phenylalanine

106 g (06 mmol) of sodium boro hydride was added to 1 g (011 mmol of hydroxyl functional groups) of malto terose (CarboSynth) dissolved in water at 65° C. After stirring for 11 minutes 05 g (010 mmol) was added (from sodium chloroacetate

5 sodium chloroacetate. Then 81 mL adapter 01P of NaOH (811 mmol) was added dropwise to this solution and the mixture was then heated at 65°C for 10 min. Then 0606 g (011 mmol) sodium chloroacetate was added to the reaction medium , with 01 mL of a solution of 01P of sodium hydroxide (011 mmol NaOH) drop by drop. The mixture was diluted with water, neutralized with acetic acid and purified by ultrafiltration.

01 On a 0 kDa polyether sulfone PES film against water. The concentration of the compound for the final solution was determined by dry extraction, after which an acid/base experiment was carried out in a 51/51 (vol/v) water/acetone mixture in order to determine the degree of substitution by methyl carboxylate.

According to the dry extract: [Compound] = 8100 mg/g.

According to an acid/base experiment, the degree of substitution by methyl carboxylate was 001/unit

05 glycoside;

A solution of sodium malto terose methyl carboxylate was acidified on purolite (anionic) resin to obtain methyl malto terose carboxylic acid which was then freeze dried for 10 h.

Using a process similar to that used to prepare compound 0, sodium malto 81t taryose methyl carboxylate reacted with phenylalanine was obtained.

According to the dry extract: [compound 1] = 0000 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1065.

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The degree of substitution by methyl carboxylate/glycoside unit was 1015.

Compound 1: Sodium Malto T Areose Methyl Carboxylate reacted with L-tryptophan

Using a process similar to that described in the preparation of compound 0, 01 g of methyl t terose carboxylic acid with a degree of substitution by 0065 methyl carboxylic acid/unit was obtained.

5 glucoside and then lyophilized.

10 g of methyl terose methyl carboxylic acid (61 mmol of methyl carboxylic acid functional groups) was dissolved in dimethylformamide DMF and then cooled from 5 to 51 °C. Then a solution of methylmorpholine (701) N-Methylmorpholine (701) g was added EtOCOCl (705 g, 60 mmol) and Ethylchloroformate, 60 mmol). Then 0005 was added

01 g of L-tryptophan (57) (Aj inomoto mmol) and the mixture stirred at 01° C. An aqueous imidazole solution 111 g/L was added and the mixture was then heated to 11° C. The mixture was diluted with water and the resulting solution purified It was ultrafiltrated on a 0 kDa PES polyether sulfone membrane against 100% sodium chloride, NaCl, 1010p sodium hydroxide solution, and water.The concentration of the final solution was determined by

05 Dry extraction. A sample of the solution was lyophilized and analyzed by 1HNMR in D2O to determine the degree of substitution by methylcarboxylates reacted with tryptophan.

According to the dry extract: [Compound 1] = 1800 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with tryptophan/unit was 81 glucoside 001.

The degree of substitution by sodium methylcarboxylates/glucoside unit was 1065.

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Compound 5: Sodium Malto T Areose Methyl Carboxylate Reacted With Cholesterol Leucinate

cholesteryl leucinate

Using a process similar to that described for the preparation of compound 0, 10 g of methyl taryose carboxylic acid with a degree of substitution by 0065 methyl carboxylate/units was obtained.

5 glucoside and then lyophilized.

The salt of para-toluenesulfonic acid was prepared from cholesteryl and leucinate according to the process described in US patent No. 1186101 (Kenji M., et al).

01 g of 01 maltotriosemethylcarboxylic acid (61 mmol of methyl carboxylic acid functional groups) is dissolved in dimethylformamide DMF

And then cooled to zero. A mixture of the para-toluenesulfonic acid salt of cholesteryl leucinate (801 g, 1 mmol) in dimethylformamide DMF was prepared. 101 g of triethylamine (1 mmol) was added to the mixture. Once the mixture reached Zero, a solution of methylmorpholine (000 NMM g) was added,

05 00 mmol) and EtOCOCl (800 g, 00 mmol). After 10 minutes,

Cholesteryl leucinate solution was added and the mixture was stirred at 01° C. Then the mixture was heated to 51°C. An imidazole aqueous solution (111 g/L) was added and the medium was diluted with water. The resulting solution was purified by ultrafiltration on a polyethersulfone (0 kDa PES) membrane versus 1010p NaOH, 100% sodium solution.

<p>81 NaCl chloride, and water. The concentration of the compound in the final solution was determined by dry extraction.</p>

<p>A sample of the solution was lyophilized and analyzed by 1HNMR in D2O to determine the degree of substitution by methyl carboxylate grafted with cholesteryl leucinate.</p>

According to the dry extract: [Compound 5] = 0100 mg/g.

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According to 1HNMR: The degree of substitution by methyl carboxylate grafted by cholesteryl leucine/glucoside unit was 1010.

The degree of substitution by sodium methyl carboxylate/glucoside unit was 0056.

Compound 6: Sodium N-methyl mannitol carbamate modified by L-phenylalanine.

5 1 g (010 mmol of hydroxyl functional groups) of mannitol (Fluka) was dissolved in dimethylformamide DMF at 11°C. After stirring for 11 minutes, DABCO-Dimethylformamide (0,1) was added [8, 8, 8] octane, 801 g; 01 mmol) and 0 ml toluene, to the mixture heated to 081 °C with stirring and heterogeneous azeotropic distillation. After the reaction mixture was re-tempered to 11 °C, 11 g (861 mmol) isocyananoethyl acetate was gradually introduced. distance

01 005 hours of reaction, the medium was precipitated from an excess of water. The solids were separated by filtration

It was poured into a mixture of tetrahydrofuran (THF/methanol (MeOH) to which 865 ml of NaOH solution was added at air temperature. The solution was stirred overnight at air temperature and then concentrated in a rotary evaporator. The rest was acidified. aqueous purolite (anionic) resin in order to obtain

05 Mannitol N-methylcarboxylic acid. The concentration of the compound in the final solution was determined by dry extraction, and then an acid/base experiment was carried out in a 51/51 water/acetone mixture (v/v) in order to determine the degree of substitution by methylcarboxylate.

According to dry extraction: [Compound] = 8701 mg/g.

81 According to an acid/base experiment, the degree of substitution by methyl carboxylate/molecule of mannitol was 101.

The N-methyl carboxylic acid mannitol solution was then lyophilized for 01 h.

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01 g mannitol N-methylcarboxylic acid (71 mmol of methylcarboxylic acid functional groups) was dissolved in dimethylformamide (01 g/L) and then cooled to zero. A mixture of ethylphenylalanate hydrochloride salt (06 g) was prepared. 71 mmol) in dimethylformamide (011 g/L) was added to this mixture. 700 g of triethylamine (71 mmol 5 mol) was added to this mixture. Once the mixture had reached zero a solution of methylmorpholine was added.

(701 NMM g, 77 mmol) EtOCOCl (101 g, 77 mmol). After 10 minutes, ethyl phenylalanine solution was added and the mixture was stirred at 10 °C. An aqueous imidazole solution (111 g/L) was added. The mixture was then heated to 11°C and then diluted with water The obtained solution was purified by 01 ultrafiltration on a 0 kDa PES polyether sulfone membrane against 100% sodium chloride.

NaCl, a solution of 1010p sodium hydroxide, NaOH, and water. The concentration of the final solution was determined by dry extraction. A sample of the solution was lyophilized and analyzed by 1HNMR in D2O to determine the degree of substitution by phenylalanine-reactive methylcarboxylate.

05 According to the dry extract: [compound 6] = 701 mg/g.

According to 1HNMR: The degree of substitution by N-methyl carboxylate reacting with phenylalanine/molecule of mannitol was 1015.

The degree of substitution by sodium N-methyl carboxylate/molecule of mannitol was 1005.

Compound 7: sodium N-phenylalanine, mannitol hexacarbamate, sodium N-phenylalaninate

mannitol hexacarbamate 81

Ethyl L-phenylalanine isocyanate has been obtained.

Tsai, JH et al. Organic Syntheses 2004, 10, according to the process described in the publication

544-545 of Ethyl L-Phenylalanine Hydrochloride Ethyl L-phenylalanine

hydrochloride (Bachem) and triphosgene (Sigma.

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1000 g (5 mmol) mannitol (Fluka) was dissolved in toluene and then 108 g (17 mmol) ethyl L-phenylalanine isocyanate and 0 g (0808 mmol) of day-as-by-cyclo [8, 8, 8[diazabicyclo[2.2.2]octane (DABCO). The mixture was heated at 01° C. overnight. After concentrating under vacuum pressure, the medium was diluted in dichloromethane and after

5 This was washed with hydrochloric (HCl) solution. The aqueous phase was extracted with dichloromethane and then the organic phases were collected, dried, and concentrated under vacuum. Ethyl N-phenylalanine mannitol hexacarbamate ethyl

flash by chromatography N-phenylalaninate mannitol hexacarbamate

Chromatography (cyclohexane / ethyl acetate).

01 Yield: 1011 g (51%).

1H NMR (DMSO-d6, ppm): 0.75-1.25 (6H); 2.75-3.15 (12H); 3.7-4.4 (22H); 4.8-5.2 (4h); 7.1-7.35 (30H); 7.4-7.85 (6H)

.MS (ESI): 1497.7 ([M+H]+); ([M+H]+ calculated: 1498.7)

8800 mL of a solution of 8N NaOH was added to 0107 g (7001 mL .).

05 mol) ethyl N-phenylalanine mannitol hexacarbamate ethyl N-phenylalaninate

/tetrahydrofuran (THF) dissolved in mannitol hexacarbamate/tetrahydrofuran mixture

Ethanol/water and the mixture was stirred at room temperature for 1 hour. After evaporating THF and ethanol under vacuum, the remaining aqueous phase was washed with dichloromethane, concentrated under vacuum, and acidified with 8H HCl. The suspension has been cooled

81 The resulting white solid was then thoroughly washed from the obtained N-phenylalanine mannitol hexacarbamate with water and then dried under vacuum pressure.

Yield: 0.081 g (07%).

1H NMR (DMSO-d6, TFA-d1, ppm): 2.6-3.25 (12H); 3.8-4.3 (10h); 4.75-5.0 (4H); 7.0-7.75 (36H).

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MS (ESI): 1329.6 ([M+H]+); ([M+H]+ calculated: 1330.4)

N-phenylalanine acid mannitol hexacarbamate was dissolved in water (51 g/L) and neutralized by the gradual addition of 01 p sodium hydroxide to give an aqueous solution of 5 N-phenylalanine mannitol hexacarbamate which was hexacarbamate. Then freeze-dry it.

1H NMR (D2O, ppm): 2.6-3.25 (12H); 3.8-4.3 (10h); 4.75-5.0 (4H);

6.9-7.5 (30H).

LC/MS (CH3CN/H2O/HCO2H (10 mM), ELSD, ESI in negative mode):

1328.4 ([M-1]); ([M-1] calculated: 1328.3)

01 This mass spectrum is shown in Figure (0).

Compound 1: Sodium Malto Tariose Methyl Carboxylate Reacting With L-phenylalanine

Using a process similar to that used to prepare compound 0, sodium malto terose methyl carboxylate reacted with phenylalanine was obtained.

According to the dry extract: [compound 1] = 0100 mg/g.

05 According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1011.

The degree of substitution by sodium methyl carboxylate/glucoside unit was 0085.

Compound 0: Sodium malto terose methyl carboxylate reacting with L-phenylalanine

106 g (06 mmol) of sodium boro hydride was added to 1 g (011 mmol of 81 hydroxyl functional groups) of maltotriose (CarboSynth) dissolved in water at 65° C. After stirring for 11 minutes 81 g (817 mm) was added mol) of sodium chloroacetate. Then 81 ml of adapter 01P of NaOH (811) mmol) was added dropwise.

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A drop was added to this solution and then the mixture was heated at 65°C for 01 min. Then 0606 g (011 mmol) sodium chloroacetate was added to the reaction medium, with 10 ml of a solution of 01 p of sodium hydroxide (011 mmol NaOH) drop by drop. The mixture was diluted with water, neutralized with acetic acid and purified by ultrafiltration over G will 0 kDa

5 Polyether sulfone PES vs. water. The concentration of the compound for the final solution was determined by dry extraction, after which an acid/base experiment was conducted in a 51/51 (vol/v) acetone/water mixture in order to determine the degree of substitution by methyl carboxylate.

According to dry extraction: [combined] = 0105 mg/g.

According to an acid/base experiment, the degree of substitution by methyl carboxylate was 0015/unit

01 glucoside;

The sodium malto- taryose methyl carboxylate solution was acidified on (anionic) borelite resin to obtain malto- methyl carboxylic acid, which was then lyophilized for 10 h.

Using a process similar to that used to prepare compound 0, sodium malto terose methyl carboxylate reacted with phenylalanine was obtained.

05 According to the dry extraction: [compound 0] = 0101 vol/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1065.

The degree of substitution by methyl carboxylate/glycoside unit was 101.

Compound 01: sodium malto t arose methyl carboxylate reacting with L-phenylalanine

81 Using a process similar to that described for the preparation of Compound 0, 1 g of sodium malto terose methyl carboxylate characterized by a degree of substitution by 0076 sodium methyl carboxylate was synthesized and lyophilized.

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1 g (51 mmol of hydroxyl functional groups) of the lyophilized product and 05 g (080 mmol) of sodium chloroacetate were dissolved in water at 65° C. 10 ml of NaOH solution was then added dropwise and then added dropwise to this solution. Then the mixture was heated at 65°C for 10 min. Then 0 g (71 mmol) of chlorine was added.

5 Sodium acetate was added to the reaction medium, with 1 ml of a solution of 01 p NaOH (11 mmol) dropwise. After heating for 0 h, the mixture was diluted with water, neutralized with hydrochloric acid and then the obtained solution was purified by ultrafiltration on a polyether membrane. Sulfone 0 kDa PES for 100% sodium chloride NaCl, 1010p sodium hydroxide solution NaOH, and water The concentration of the final solution was determined by extraction.

01 dry. A sample of the solution was lyophilized and analyzed by 1HNMR in D2O to determine the degree of substitution by methyl carboxylate reacting with sodium malto terose methyl carboxylate.

According to the dry extract: [Compound] = 0007 mg/g.

According to an acid/base experiment, the degree of substitution by methyl carboxylate was 1011.

05 A solution of sodium malto terose methyl carboxylate was acidified on borolite (anionic) resin to obtain malto terose methyl carboxylic acid, which was then lyophilized for 10 hours.

Using a process similar to that used to prepare compound 0, sodium malto terose methyl carboxylate reacted with phenylalanine was obtained.

81 According to dry extraction: [compound 01] = 0100 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1065.

The degree of substitution by methyl carboxylate/glycoside unit was 8065.

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Compound 00: sodium maltopentose methyl carboxylate reacting with L-phenylalanine

Using a process similar to that described for the preparation of compound 0, but implemented by maltopentose (CarboSynth), 10 g of methyl pentose carboxylic acid of substitution by methyl carboxylic acid 0075/glucoside units was obtained and then lyophilized.

5 Using a process similar to that used to prepare compound 0, sodium maltopentose methyl carboxylate reacted with phenylalanine was obtained.

According to dry extraction: [compound 00] = 700 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1075.

01 The degree of substitution by methyl carboxylate/glycoside unit was 001.

Compound 08: Sodium Malto-Octose Methyl Carboxylate Reacted with L-Phenylalanine

Using a process similar to that described for the preparation of Compound 0, but implemented by maltooctose (CarboSynth), 10 g of methyl carboxylic maltooctose acid of substitution by methyl carboxylic acid 0065/glucoside unit was obtained and then lyophilized.

05 Using a process similar to that used to prepare compound 0, sodium maltooctose methyl carboxylate reacted with phenylalanine was obtained.

According to dry extraction: [compound 08] = 8601 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1065.

81 The degree of substitution by methyl carboxylate/glycoside unit was 001.

Compound 01: Sodium Malto T Areose Methyl Carboxylate Reacted With Cholesteryl Leucinate

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Using a process similar to that mentioned in the preparation of compound 5, sodium malto terose methyl carboxylate was obtained, which was characterized as having a degree of substitution by sodium methyl carboxylate 0011 and was reacted with cholesteryl leucine.

According to dry extraction: [compound 01] = 0100 mg/g.

5 According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1011.

The degree of substitution by methyl carboxylate/glycoside unit was 0076.

Compound 01: Sodium Malto T Areose Methyl Carboxylate Reacted With Cholesteryl Leucinate

Using a process similar to that mentioned for the preparation of compound 5, sodium malto-01 taryose methyl carboxylate was obtained, characterized by its degree of substitution by sodium methyl carboxylate 0080.

It was reactive with cholesteryl leucine.

According to dry extraction: [compound 01] = 8001 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1080.

05 The degree of substitution by methyl carboxylate/glycoside unit was 0011.

Compound 05: Sodium Malto-Terose Methyl Carboxylate Reacted With Cholesteryl Leucinate

Using a process similar to that described in the preparation of Compound 01, 01 g of methyl carboxylic acid malto-triose carboxylic acid of substitution by 1011 methyl carboxylic acid/glucoside unit was obtained and then lyophilized.

81 Using a process similar to that described for Compound 5, sodium malto terose methyl carboxylate characterized as having a substitution degree with sodium methyl carboxylate 1011, was reacted with cholesteryl leucinate.

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According to the dry extraction: [Compound 05] = 0100 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1080.

The degree of substitution by methyl carboxylate/glycoside unit was 1010.

5 Compound 06: Sodium Maltopentose Methyl Carboxylate Reacted with Cholesteryl Leucinate

Using a process similar to that described for the preparation of compound 00, 01 g of methyl pentose carboxylic acid, characterized as having a degree of substitution by 0075 methyl carboxylic acid, was synthesized, after which it was lyophilized.

Using a process similar to that described for the preparation of compound 5, sodium malto01 pentose methyl carboxylate reacted with cholesteryl leucinate was obtained.

According to dry extraction: [compound 06] = 0100 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1001.

The degree of substitution by methyl carboxylate/glycoside unit was 0060.

05 Compound 07: Sodium Malto-Octose Methyl Carboxylate Reacted with Cholesteryl Leucinate

Using a process inspired by that described in the preparation of Compound 08, 01 g of maltooctose methylcarboxylic acid, characterized as having a degree of substitution by 008 methylcarboxylic acid, was synthesized and subsequently lyophilized.

Using a process similar to that described for the preparation of compound 5, sodium malto-octose 81-octose methyl carboxylate reacted with cholesteryl leucinate was obtained.

According to dry extraction: [Compound 07] = 0107 mg/g.

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According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1010.

The degree of substitution by methyl carboxylate/glycoside unit was 0000.

Compound 01: Sodium Maltoate methyl carboxylate reacting with β-benzyl aspartate

5 Using a process similar to that described in the preparation of Compound 0, 01 g of substitution of methyl carboxylic acid 0061/glucoside unit was obtained and then lyophilized.

6 g of MTA (11 mmol of methylcarboxylic acid functional groups) was dissolved in dimethylformamide DMF and then cooled to zero. 01 A mixture of β-benzyl aspartate (Bachem, 105 g, 06 mmol) was prepared. (Wattari Ethylamine

(06 mmol) in water. A solution of 108 NMM methylmorpholine (g, 18 mmol) was then added. and 101 g EtOCOCl (EtOCOCl, 18 mmol) was added to the solution of methylmalto-triose methylcarboxylic acid at zero. To this, a solution of benzyl aspartate and triethylamine was added and the mixture was stirred at 11° C. An aqueous imidazole solution (111 g/05 L) was added after 10 min. The medium was diluted with water and then the obtained solution was purified by

Ultrafiltration on a 0 kDa PES polyether sulfone membrane against 051 mM buffer solution 0101 = pH, NaHCO3/Na2CO3, 100% sodium chloride NaCl and water. A sample of the solution was freeze-dried and analyzed by 1HNMR in D2O to be graded by methylcarboxylate reacting with β-benzyl aspartate.

81 According to dry extraction: [compound 01] = 0501 mg/g.

According to 1HNMR: The degree of substitution by methylcarboxylate reacting with phenylalanine/glucoside unit was 1051.

The degree of substitution by methyl carboxylate/glycoside unit was 0005.

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Compound 00: sodium malto t erose methyl carboxylate reacted with dilauryl aspartate

The salt of P-toluene sulfonic acid of DLA was prepared from dodecanol and aspartic acid according to the process described in US Pat. No. 1186101 (Kenji M., et al).

Using a process inspired by that to prepare compound 01, 01 g of 5 methyl aryose carboxylic acid substitution by methyl carboxylic acid 8071/u glucoside was obtained and then lyophilized.

Using a process similar to that described in the preparation of compound 5, sodium malto terose methyl carboxylate, characterized by a degree of substitution by sodium methyl carboxylate 8071, was reacted with dilauryl aspartate in dimethylformamide DMF. The medium was diluted with water and then the obtained solution 01 was purified by ultrafiltration on a 0 kDa PES polyether sulfone membrane against 051 mM buffer solution 0101 = pH, NaHCO3/Na2CO3, 100% sodium chloride NaCl and water. A sample of the solution was freeze dried and analyzed by 1HNMR in D2O to be graded by methylcarboxylate reacting with dilauryl aspartate.

According to dry extraction: [compound 00] = 101 mg/g.

05 According to 1HNMR: The degree of substitution by methyl carboxylate reacting with phenylalanine/glucoside unit was 1061.

The degree of substitution by methyl carboxylate/glycoside unit was 8017.

Compound 81: Sodium malto terose methyl carboxylate reacted with:

2-[(2-dodecanoylamino-6-dodecanoylamino)hexanoylamino]ethanamine

81 The methyl ester of N,N-bis(dodecanoyl) lysine-N,N has been obtained.

Pal, A et al., Tetrahedron 2007, according to the process described in bis(dodecanoyl)lysine

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63, 7348-7334, from the methyl ester of the hydrochloride salt of L-lysine (Bachem) and from dodecanoic acid (Sigma).

2-[(2-dodecanoylamino-6-dodecanoylamino)hexanoylamino]ethanamine

According to the process described in US Pat. No. 8117810 (Weiner et al), from the 5-methyl ester of N,N-bis(dodecanoyl)lysine,N-bis(dodecanoyl)lysine and from ethylenediamine

.(Roth)

Using a process similar to that described in the preparation of compound (01), 10 g of methyl terose methyl carboxylic acid with a degree of substitution by 8071 methyl carboxylic acid/glucoside unit was obtained and then lyophilized.

01 Using a process similar to that described in the preparation of compound 00, sodium malto terose methyl carboxylate, characterized by a degree of substitution by sodium methyl carboxylate 8071, was reacted with:

2-[(2-dodecanoylamino-6-dodecanoylamino)hexanoylamino]ethanamine.

According to dry extraction: [compound 81] = 801 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacted with:

2-[(2-dodecanoylamino-6-dodecanoylamino)hexanoylamino]ethanamine 05

.1080

The degree of substitution by methyl carboxylate/glycoside unit was 8058.

Compound 80: sodium malto terose methyl carboxylate reacting with (8-N-aminoethyl)

N-(2-aminoethyl)dodecanamide dodecanamide

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According to the process described in US Pat. No. 801170810 (Weiner et al), (8-N-aminoethyl) dodecanoic acid was obtained from a methyl ester of dodecanoic acid (Sigma) and ethylenediamine (Roth).

Using a process similar to that described in the preparation of compound 01, 01 g of 5 methyl tearose carboxylic acid was obtained with a degree of substitution by methyl carboxylic acid 0061/glucoside unit and then lyophilized.

Using a process similar to that described in the preparation of compound 00, sodium maltotriose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with N-(8-aminoethyl) dodecanamide.

01 According to dry extraction: [compound 80] = 801 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with (8-N-aminoethyl) dodecanamide was 1087.

The degree of substitution by methyl carboxylate/glycoside unit was 0017.

Compound 88: Sodium Maltose Areose Succinate Reacted With Dilauryl Aspartate

05 85 g (i.e. 10511 mol of hydroxyl functional groups) of maltose aryose was dissolved in 68 ml DMSO at 61°C, after which the temperature was programmed at 11°C. 5001 g (10,508 mmol) succinic anhydride was added in solution in 68 mL dimethylformamide DMF and 5,000 g (10,508 mmol) of N-methylmorpholine, diluted in 68 mL dimethylformamide DMF, to this solution. After 1 81 hours of reaction, the reaction medium was then diluted in water (67 mL) and Purification of oligosaccharides by ultrafiltration. The molecular fraction of the succinic acid ester formed/glucoside unit was 8807 according to 1HNMR in D2O/NaOD.

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A solution of sodium maltotriosesuccinate was acidified on purolite (anionic) resin to obtain maltotriosesuccinic acid which was then freeze dried for 01 h.

Using a process similar to that described for the preparation of compound 00, sodium maltose aryose was reacted

5 Succinate is characterized by a degree of replacement by Sodium Succinate 8077, with Dilauryl Aspartate

.dilauryl aspartate

According to dry extraction: [compound 88] = 0800 mg/g.

According to 1HNMR: The degree of substitution by succinate reacting with dilauryl aspartate was 1011.

01 The degree of substitution by methyl carboxylate/glycoside unit was 8016.

Compound 81: Sodium Malto-Terose Methyl Carboxylate reacted with Decanoylglycinate

The para-toluenesulfonic acid salt of decanoyl glycinate was prepared from decanol and glycine according to the process described in US Pat. No. 1186101 (Kenji M., et al).

05 Using a process similar to that described in the preparation of compound 80, sodium malto terose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with decanoylglycinate.

According to dry extraction: [compound 81] = 801 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with decanoyl glycinate 81 was 1080.

The degree of substitution by methyl carboxylate/glycoside unit was 0011.

Compound 81: sodium malto t erose methyl carboxylate reacted with L-leucine.

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Using a process similar to that described for the preparation of compound 01, but including L-leucine (Roth), sodium malto taryose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with L-leucine.

According to dry extraction: [compound 81] = 801 mg/g.

5 According to 1HNMR: The degree of substitution by methyl carboxylate reacting with L-leucine was 1051.

The degree of substitution by methyl carboxylate/glycoside unit was 0016.

Compound 85: sodium malto t erose methyl carboxylate reacting with cholesteryl 8-aminoethyl

cholesteryl 2-aminoethylcarbamate carbamate

01 The hydrochloric acid salt of cholesteryl 8-aminoethylcarbamate was prepared according to the process described in I.A. No. 8101/151011 (Akiyoshi, K et al).

Using a process similar to that described in the preparation of compound 00, sodium maltotriose methyl carboxylate, characterized by a degree of substitution by sodium methyl carboxylate 1078, was reacted with cholesteryl 8-aminoethyl carbamate.

05 According to dry extract: [compound 85] = 800 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with cholesteryl 8-aminoethyl carbamate was 1081.

The degree of substitution by methyl carboxylate/glycoside unit was 8015.

Compound 86: Sodium malto t erose methyl carboxylate reacting with alpha-phenylglycine.

phenylglycine 81

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Using a process similar to that described for the preparation of compound 01, but including alpha-phenylglycine (Bachem), sodium malto terose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with alpha-phenylglycine.

According to dry extraction: [compound 86] = 000 mg/g.

5 According to 1HNMR: The degree of substitution by methyl carboxylate reacting with alpha-phenylglycine was 1058.

The degree of substitution by methyl carboxylate/glycoside unit was 0008.

Compound 87: Sodium malto terose methyl carboxylate reacted with:

2-[(2-octanoylamino-6-octanoylamino)hexanoylamino]ethanamine

Pal, A According to the process described in N,N-bis(octanoyl)lysine 01 a methyl ester was obtained for

L-methyl ester of the hydroxide salt of L-Tetrahedron, et al., 2007, 63, 7334-7348

Lysine (Bachem) and from dodecanoic acid (Sigma). Obtained:

2)]-2 according-octanoylamino-6-octanoylamino)hexanoylamino]ethanamine

For the process described in US Patent No. 8117810 (Weiner et al), from the methyl ester of:

05 N,N-bis(octanoyl)lysine and ethylenediamine (Roth).

Using a process similar to that described for the preparation of compound 80, sodium malto terose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with:

2-[(2-octanoylamino-6-octanoylamino)hexanoylamino]ethanamine.

According to the dry extract: [compound 87] = 101 mg/g.

81 According to 1HNMR: The degree of substitution by methyl carboxylate reacted with:

.1081 2-[(2-octanoylamino-6-octanoylamino)hexanoylamino]ethanamine

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The degree of substitution by methyl carboxylate/glycoside unit was 0016.

Compound 81: Sodium Malto-Terose Methyl Carboxylate reacted with L-Tyrosine

Using a process similar to that described for preparing compound 0, but including the hydrochloric acid salt, of methyl tyrosine (Bachem), sodium malto taryose methyl carboxylate, 5 characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with tyrosine.

According to the dry extract: [compound 81] = 000 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with L-tyrosine was 1010.

The degree of substitution by methyl carboxylate/glycoside unit was 1011.

01 Compound 80: sodium malto t erose methyl carboxylate reacted with 8-aminoethyl dodecanoate

aminoethyl dodecanoate

The p-toluene sulfonic acid salt of 8-aminoethyldodecanoate was obtained according to the process described in US Pat. No. 1186101 (Kenji M et al), from dodecanoic acid (Sigma) and from ethanolamine (Sigma).

05 Using a process similar to that described for the preparation of compound 80, sodium malto terose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with 8-aminoethyl dodecanoate.

According to the dry extract: (compound 80) = 001 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with 8-aminoethyl 81 decanoate was 1087.

The degree of substitution by methyl carboxylate/glycoside unit was 0017.

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Compound 11: sodium malto t erose methyl carboxylate reacting with 1,7-dimethyloctanyl

dimethyloctanoyl phenylalaninate phenylalanine

The para-toluenesulfonic acid salt of 1,7-dimethyloctanoylphenylalanine was prepared from 1,7-dimethyl

L-phenylalanine phenylalanine -L 3,7-dimethyloctan-1-ol 5-octane -0-ol

According to the process described in US Patent No. 101860101 (Kenji et al).

Using a process similar to that described in the preparation of compound 80, sodium maltotriose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methylcarboxylate, was reacted with 1,7-dimethyloctanoylphenylalanine

.dimethyloctanoyl phenylalaninate 01

According to the dry extract: [Compound 11] = 101 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with 1,7-dimethyloctanoylphenylalanine was 1010.

The degree of substitution by methyl carboxylate/glycoside unit was 0085.

05 Compound 10: sodium hyaluronate tetrasaccharide reacted with methyl phenylalanine

A solution of 4-mer sodium hyaluronate (Contipro Biotech) at a concentration of 11 g/L was acidified with Purulite (anionic resin) to obtain an aqueous solution of hyaluronic acid numbered.

81 pH 700 by adding an aqueous solution (11%) tetrabutylammonium hydroxide (Sigma). The solution was then lyophilized for 01 h.

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11 mg of tetrabutylammonium hyaluronate (11 μmol of tetrabutylammonium carboxylate functional groups) was dissolved in DMF. 5 mg of methyl phenylalanine (81 μmol) and 6 μmol of methyl phenylalanine) were added. (61 μmol), 0

5 mg 8-chloro-0-methylpyridinium iodide (2-chloro-1-methylpyridinium iodide (16 μmol Sigma) at 0°C and then stirred at 81°C for 06 h. The solvent was evaporated and the remainder analyzed by 1HNMR in D2O to be Determination of the degree of interaction of acid functional groups with methyl phenylalanine.

According to 1HNMR: The degree of substitution by carboxylate reactant with methylphenylalanine/01 polysaccharide unit was 1088.

The degree of substitution by sodium carboxylates/saccharide unit was 1081.

Compound 18: sodium . methyl carboxylate methyl carboxylate

maltotriosemethylcarboxylate interacts with :

2-[(2-decanoylamino-6-decanoylamino)hexanoylamino]ethanamine 05

The methyl ester of N,N-bis(decanoyl)lysine-N,N has been obtained.

Pal, A et al., Tetrahedron 2007, 63, according to the process described in bis(decanoyl)lysine

7334-7348, from the methyl ester of the hydrochloric salt of L-lysine (Bachem) and from dodecanoic acid (Sigma). Obtained:

2)]-2 according-decanoylamino-6-decanoylamino)ethanamine 81

For the process described in US Pat. No. 8117810 (Weiner et al), from a methyl ester of N, N-bis(decanoyl) lysine and from ethylenediamine (Roth).

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Using a process similar to that described for the preparation of compound 80, sodium malto terose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with:

2-[(2-decanoylamino-6-decanoylamino)hexanoylamino]ethanamine.

According to dry extract: [Compound 18]: 100 mg/g.

<p>5 According to 1HNMR: The degree of substitution by methyl carboxylate reacted with:</p>

.1080 2-[(2-decanoylamino-6-decanoylamino)hexanoylamino]ethanamine

The degree of substitution by methyl carboxylate/glycoside unit was 0011.

Compound 11: sodium malto-t aryose methyl carboxylate reacting with N-ε-dodecanoyl-L-lysine

-N-dodecanoyl-L-lysine

<p>01 The ethyl ester of the hydrochloric acid salt of N-ε-dodecanoyl-L-lysine from dodecanoic acid (Sigma) and the ethyl ester of the hydrochloride salt of L-lysine (Bachem), was prepared according to the process described in US Pat. No. 1086681 (Paquet AM).</p>

Using a process similar to that described in the preparation of Compound 0, sodium malto terose methyl carboxylate, characterized by a degree of substitution by 0061 sodium methyl carboxylate, was reacted with N-ε-05 dodecanoyl-L-lysine.

According to the dry extract: [Compound 11] = 108 mg/g.

According to 1HNMR: The degree of substitution by methyl carboxylate reacting with N-ε-dodecanoyl-L-lysine was 1017.

The degree of substitution by methyl carboxylate/glycoside unit was 0087.

81 Compound 11: sodium N-phenylalaninate mannitol 8, 1, 1, 5- 2,3,4,5-tetracarbamate carbamate

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0,6-ditaryisopropylsilylmannitol 1,6-ditriisopropylsilyl mannitol was obtained according to the process described in a publication:

Bhaskar, V et al., Journal of Carbohydrate Chemistry 2003, 22(9), 867

879.

5 Using a process similar to that described for the preparation of compound 7, it was obtained:

[1,6-ditriisopropylsilyl-2,3,4,5-tetra(sodium N-phenylalaninate)

carbamate)]mannitol

Using a process similar to the one mentioned in the post:

Tarry Collections Protection Removed, PJ Edwards et al., Synthesis 1995, 9, 898-900

01 Triisopropylsilyl to give:

N-phenylalanine acid mannitol 2,3,4,5-tetracarbamate

Using a process similar to that described in Compound 7, to obtain a compound:

sodium N-phenylalaninate mannitol 2,3,4,5-tetracarbamate

1H NMR (D2O, ppm): 2.6-3.25 (8H); 3.6-4.3 (8H); 4.75-5.0 (4H); 6.9

.7.5 (24H) 05

Example vs. A0: sodium . didexarne methyl carboxylate

L-phenylalanine L-phenylalanine reacts with dextranmethylcarboxylate

Sodium dextranmethylcarboxylate reacted with L-phenylalanine from Dexarn, having a -weight molecular mass

81 average molar mass 0 kg/mol (Pharmacosmos, medium 100 degree of polymerization) according to a process similar to that described in I.A. No. 8108/051171.

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The degree of substitution by sodium methylcarboxylates/glucoside unit was 001 glucoside.

The degree of substitution by methyl carboxylate reacting with L-phenylalanine/glucoside unit was 1065.

5 Example vs. A8: Sodium . didexarne methyl carboxylate

L-phenylalanine reacted with dextranmethylcarboxylate

Dexarne methyl carboxylate reactive sodium with L-phenylalanine was synthesized from Dixitarne with a mean molecular mass of 5 kg/mol (Pharmacosmos, medium polymerization degree 00) according to a process similar to that mentioned in I.A. No. 8101/088115.

01 The degree of substitution by sodium methyl carboxylate/glucoside unit was 1001.

The degree of substitution by methyl carboxylate reacting with L-phenylalanine/glucoside unit was 1066.

Example vs. B0: Sodium Dixatearne Methyl Carboxylate Reacted with Cholesteryl Leucinate

cholesteryl leucinate

05 The Reactive Sodium Dexarne Methyl Carboxylate with L-cholesteryl leucinate was synthesized from Dexarne with a mean molecular mass of 0 kg/mol (Pharmacosmos, M 100) according to a process similar to that described in I.A. No. 8108/051171.

The degree of substitution by sodium methyl carboxylate/glucoside unit was 0061.

The degree of substitution by methyl carboxylate reacting with L-phenylalanine/glucoside unit was 81 1015.

Example vs. B8: Sodium Dixatearne Methyl Carboxylate Reacted with Cholesteryl Leucinate

cholesteryl leucinate

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Dextran Sodium methyl carboxylate reactive with L-cholesteryl leucinate was synthesized from DextArn with an average molecular mass of 5 kg/mol (Pharmacosmos, MPO 00) according to a process similar to that described in I.A. No. 8101/110000.

The degree of substitution by sodium methyl carboxylate/glucoside unit was 006.

5 The degree of substitution by methyl carboxylate reacting with L-phenylalanine/glucoside unit

1011.

B- Turbidity measurement assays

The turbidity was analyzed in solutions in which a typical protein, lysozyme, and any of the invention compound or an example compound was synthesized, with molar ratios of compound/lysozyme 100 and 105.

01 The following solutions were prepared in advance: histidine buffer, pH 608 ± 100 at a concentration of 001 mM (11 mg/mL), sodium chloride solution (NaCl) at a concentration of 5107 M (801 mg/mL). (1015 mM), and solutions of each of the tested products (pH 608 ± 100), i.e. compounds of the invention and corresponding examples.

For each of the solutions of the compounds to be prepared, 1 mL of the aqueous solution of the compound was adjusted to pH 05 608 ± 100 using 51 ± 85 μl of 100H HCl.

(HCl).

The details of the solutions of the tested compounds are given in the following table (1).

Table (1)

<tr><td><p>pH</p><p>pH of solutions</p><p>Final</p></td><td><p>Final focus</p><p>For Vehicles (Mm)</p></td><td><p>Tested Products</p></td></tr><tr><td><p>601</p></td><td><p>601</p></td><td><p>0 . compound</p></td></tr>

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<tr><td><p>608</p></td><td><p>8708</p></td><td><p>Example vs A0</p></td></tr><tr><td><p>601</p></td><td><p>501</p></td><td><p>Example vs A8</p></td></tr><tr><td><p>601</p></td><td><p>006</p></td><td><p>Compound 01</p></td></tr><tr><td><p>608</p></td><td><p>0107</p></td><td><p>Example vs 0</p></td></tr><tr><td><p>601</p></td><td><p>501</p></td><td><p>example vs b8</p></td></tr>

The tested solutions were then prepared with the molar ratios of compound/lysozyme: zero, 100, and 105 as follows.

Sodium chloride solution was added at a concentration of 5107 mM, and the buffer solution of histidine at a concentration of 001 mM was added, and then the solution of the compound was successively added to water, which produced

5 The mixture was homogenized in a Stuart Roller Mixer SRT9D (roller mixer) for 1 minute.

Finally a lysozyme solution was added and then the final solution was homogenized on a Delphini mixer for 1 minute.

Turbidity (expressed as NTU) for each final laboratory solution was measured using a turbidimeter

.HACH 2100AN turbidity meter 01

The turbidity of the complex 0/lysozyme solution was analyzed in comparison with the turbidity of solutions of example A0/lysozyme and example versus A8/lysozyme. The turbidity of the solution of compound 01, lysozyme was analyzed in comparison with the turbidity of solutions of example B0, lysozyme and example versus B8/lysozyme. The results are shown in the following table (1).

Table (1)

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<tr><td><p>Turbidity of solutions at</p><p>molar ratio 105</p><p>(NTU)</p></td><td><p>Turbidity of solutions at</p><p>molarity ratio 100</p><p>(NTU)</p></td><td><p>Turbidity of solutions at zero molarity</p><p>(NTU)</p></td><td></td></tr><tr><td><p>101</p></td><td><p>55</p></td><td><p>0</p><p>zero</p></td><td><p>Complex 0-lysozyme solution</p></td></tr><tr><td><p>8111</p></td><td><p>060</p></td><td><p>zero</p></td><td><p>Example solution versus A0-lysozyme</p></td></tr><tr><td><p>0116</p></td><td><p>0801</p></td><td><p>zero</p></td><td><p>Example solution for A8-lysozyme</p></td></tr><tr><td><p>105</p></td><td><p>18</p></td><td><p>zero</p></td><td><p>Complex 01-lysozyme solution</p></td></tr><tr><td><p>761</p></td><td><p>01</p></td><td><p>zero</p></td><td><p>Example solution versus B0-lysozyme</p></td></tr><tr><td></td><td><p>0181</p></td><td><p>zero</p></td><td><p>B8- Lysozyme</p></td></tr>

The turbidity of the solution of compound 0/lysozyme was less than that of the solutions of the corresponding example compound A0/lysozyme and of the corresponding example compound A8/lysozyme, whatever the ratio

The turbidity of the solution of compound 01/lysozyme was less than that of the solutions of the corresponding example compound B0/lysozyme and for the corresponding example compound B8/lysozyme, whatever the ratio was.

5 Interaction with albumin

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It is known that the compounds of the previous art do not make it possible to obtain nonturbid solutions with lysozyme, and that they interact with proteins, especially with typical proteins such as albumin.

In order to follow the results obtained by the compounds of the invention in a test with lysozyme (i.e. the 5 turbidity experiments mentioned before) to determine whether there are, however, typical proteins

It can react with the compounds of the invention, a test for reaction with albumin was carried out.

The test performed was a “fluorescence” test with albumin, which by measuring the differences in the fluorescence of albumin, checks whether there is an interaction between the tested compound and albumin.

Compound/albumin solutions were prepared from crude solutions of the compounds and serum albumin 01 (BSA) by mixing appropriate volumes to obtain the concentration of bovine serum albumin.

serum albumin (BSA) was stable at 105 mg/ml, and BSA compound/by weight ratios were 005 and 01. These solutions were prepared in PBS buffer solution at −01 = pH .

811 μl of different compound/BSA solutions were introduced into a 06-well plate. Fluorescence measurements were made at room temperature (81°C) with a fluorescence spectrophotometer.

05 EnVision® from PerkinElmer. The excitation wavelength was 811 nm and the emission wavelength was 151 nm. This corresponds to the fluorescence of tryptophan residues of albumin. Ruiz-P.

et al., M, A. Physico-chemical studies of molecular interactions between non-ionic surfactants and bovine serum albumin, Colloids Surf. B

2009 Biointerfaces. F ratio (compound/BSA)/fluorine oxide (FO)

<p>81 (BSA alone). Makes it possible to evaluate the interaction between the compound and albumin. If this ratio is less than</p>

<p>0, this means that the compound induces partial quenching of albumin fluorescence related to a change in the environment of tryptophan residues. This change reflects an interaction between the compound and albumin. It was verified, as a comparison sample, that for all compounds tested, the fluorescence of the compound was</p>

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Alone could be omitted when the albumin fluorescence was taken into account (compound fluorescence &gt;8% of albumen fluorescence. The results are given in Table (5).

<tr><td><p>calendar</p><p>F/F0&lt;0.85</p></td><td><p>calendar</p><p>F/F0&lt;0.5</p></td><td><p>BSA compound by weight</p></td><td><p>compound</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>00</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>81</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>80</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>88</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>81</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>87</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>80</p></td></tr><tr><td></td><td><p>Yes</p></td><td><p>0</p></td><td><p>11</p></td></tr><tr><td><p>The</p></td><td><p>The</p></td><td><p>0</p></td><td rowspan="3"><p>8</p></td></tr><tr><td><p>Yes</p></td><td><p>The</p></td><td><p>5</p></td></tr><tr><td><p>Yes</p></td><td><p>The</p></td><td><p>01</p></td></tr>

explain

The results show that all compounds react with albumin.

5 For compounds 11-00, it causes a decrease in the fluorescence ratio so that it is &lt;105 F/F0 at compound/by weight of BSA = 0.

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For compound 8, it reduces the fluorescence ratio such that it is &lt; 1015 F/F0 at the weight ratio of compound/5 BSA and 01.

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