Pyrrolopyrimidine nucleosides and analogs thereof useful as antiviral agents
Abstract
A compound of formula IB: ** (See formula) ** or a pharmaceutically acceptable salt, solvate, enantiomer, diastereoisomer, racemate or mixture thereof, wherein: A is: ** (See formula) ** X1 is -CR11R12- or -OCH2CH2-, wherein the oxygen atom is distal to the RIB moiety in A; R11 and R12 are independently hydrogen or C1-C4 alkyl, wherein the alkyl is optionally substituted with one or more of halogen, -OH, -SH, or -NH2; X2 is absent, it is -O-, -C (O) O-, or -OCH2-, wherein the oxygen atom is distal to the RIB moiety in A; each RIB is independently hydrogen, -C1-C6 alkyl, ** (See formula) ** or RIB is an amino acid residue attached via the carbonyl group, wherein the alkyl is optionally substituted with one or more halogen, -OH, -SH or -NH2; v is 0 or 1; n is 0, 1, 2 or 3 and when X2 is -C (O) O-, n is 0; p is 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; q is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18; Rz is hydrogen, halogen, -C1-C4 alkylthio, -C1-C4 alkoxy, -C1-C4 alkyl, -C2-C4 alkenyl, -C2-C4 alkynyl, aryl, heteroaryl, -C3-C8 cycloalkyl, -C4-cycloalkenyl C8 or 3- to 5-membered non-aromatic heterocycle, wherein each alkylthio, alkoxy, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, or heterocycle is optionally substituted with one or more of halogen, -OH, -SH, or -NH2; Ra, Rb, Rx, and Ry are each independently selected from the group consisting of hydrogen, halogen, -OH, -SH, -C1-C6 alkoxy, aryloxy, -C1-C6 alkylthio, arylthio, -OC (O) C1 alkyl -C6, -OC (O) aryl, -C1-C6 alkyl, -C2-C6 alkenyl, -25 C2-C6 alkynyl, aryl, heteroaryl, -C3-C8 cycloalkyl, and -C4-C8 cycloalkenyl, wherein each alkoxy , aryloxy, alkylthio, arylthio, alkyl, aryl, alkenyl, alkynyl, heteroaryl, cycloalkyl or cycloalkenyl is optionally substituted with one or more of halogen, -OH, -SH or -NH2; or any two Ra or Rb, together with the atom to which they are both attached, may combine to form a C3-C8 spirocycloalkyl or 3- to 8-membered spiroheterocycle; or any two Ra or Rb, when on adjacent atoms, can combine to form a carbon-carbon double bond or a cis or trans carbon-carbon triple bond; or any two Ra or Rb, when on adjacent atoms, may combine to form an aryl, heteroaryl, -C3-C10 -cycloalkyl, -C4-C10 -cycloalkenyl, or 5- to 10-membered ring-membered heterocycle; or any CRaRb can be replaced by -O-, -S-, -S (O) - or -SO2-; or any two Rx or Ry, together with the atom to which they are both attached, may combine to form a 3- to 8-membered - spirocycloalkyl or spiroheterocycle; or any two Rx or Ry, when on adjacent atoms, can combine to form a carbon-carbon double bond or a cis or trans carbon-carbon triple bond; or any two Rx or Ry, when on adjacent atoms, may combine to form an aryl, heteroaryl, -C3-C10 -cycloalkyl, -C4-C10 -cycloalkenyl, or 5- to 10-membered ring-membered heterocycle; or any CRxRy can be replaced by -O-, -S-, -S (O) - or -SO2-; R1 and R45 are each independently hydrogen, halogen, -N3, -OH, -NH2, -SH, -C1-C6 alkyl, -C3-C6 cycloalkyl, -C2-C6 alkenyl, -C4-C8 cycloalkenyl, -C2 alkynyl -C6, -C8-C12 cycloalkynyl, -C 1-6 alkoxy or -C 1-6 alkylthio in which each alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkoxy or alkylthio is independently substituted with one or more halogen, - N3, -OH, -NH2 or -SH; R2, R3, R4, and R44 are each independently hydrogen, halogen, -N3, -OH, -NH2, -SH, -C1-C6 alkyl, -C1-C6 alkoxy, or -C1-C6 alkylthio, wherein each alkyl , alkoxy or alkylthio is optionally substituted with one or more of halogen, -N3, -OH, -NH2 or -SH; or R3 and one of R4 and R44, together with the atoms to which they are attached may form a carbon-carbon double bond; R5 is independently hydrogen, -RIB, M +, aryl, aralkyl, -C1-C6 alkyl, -C1-C6 heteroalkyl, cycloalkyl, non-aromatic heterocyclic ring or heteroaryl, wherein M + is a cation and wherein each aryl, aralkyl , alkyl, heteroalkyl, cycloalkyl, heterocycle, or heteroaryl is optionally substituted with one or more of halogen, -N3, -OH, -NH2, or -SH, and wherein R5 is not an amino acid; and Rc is -C1-C6 alkyl, -C3-C6 cycloalkyl, -C2-C6 alkenyl, -C4-C8 cycloalkenyl, -C2-C6 alkynyl, -C8-C12 cycloalkynyl or aryl, wherein each alkyl, cycloalkyl, alkenyl , cycloalkenyl or aryl is optionally substituted with one or more of halogen, -N3, -OH, -NH2 or -SH.
Term
9.9 yearsto projected expiry
Projected expiry 8 August 2036, counted from filing; an application has no term until it is granted.
- Priority
- Filed
- Published
- Today
- Projected expiry
27 members in 14 offices
Priority claims5
| Document | Office | Kind | Date |
|---|---|---|---|
| 201562202010 | United States of America | P | |
| 201562202010P | United States of America | – | |
| 201606645 | United Kingdom | A | |
| 201606645 | United Kingdom | – | |
| 2016046056 | United States of America | W |
Members27
| Document | Office | Kind | |
|---|---|---|---|
| CA2992278A1 | Canada | A1 | |
| WO2017024310A1 | World Intellectual Property Organization (WIPO) | A1 | |
| US2017044202A1 | United States of America | A1 | |
| US2017137454A1 | United States of America | A1 | |
| US9701706B2 | United States of America | B2 | |
| US9708359B2 | United States of America | B2 | |
| US2017253628A1 | United States of America | A1 | |
| AU2016301188A1 | Australia | A1 | |
| IL257122A | Israel | A | |
| IL257122D0 | Israel | D0 | |
| KR20180039666A | Republic of Korea | A | |
| CN108026136A | China | A | |
| MX2018001073A | Mexico | A | |
| EP3331895A1 | European Patent Office (EPO) | A1 | |
| EA201890454A1 | Eurasian Patent Organization (EAPO) | A1 | |
| PH12018500263A1 | Philippines | A1 | |
| JP2018523665A | Japan | A | |
| BR112018002399A2 | Brazil | A2 | |
| US10407457B2 | United States of America | B2 | |
| US2020199167A1 | United States of America | A1 | |
| EP3331895B1 | European Patent Office (EPO) | B1 | |
| US10941175B2 | United States of America | B2 | |
| ES2829254T3This record | Spain | T3 | |
| US2022002335A1 | United States of America | A1 | |
| KR102630013B1 | Republic of Korea | B1 | |
| US11981700B2 | United States of America | B2 | |
| US2025084119A1 | United States of America | A1 |
Numbers
- Publication
- 2829254
- Application
- 16753540
Titles2
- Spanish
- Nucleósidos de pirrolopirimidina y análogos de los mismos útiles como agentes antivíricos
- English
- Pyrrolopyrimidine nucleosides and analogs thereof useful as antiviral agents
Classification
- IPC, 4
- C07H19 16
- A61K31 06
- A61K31 7076
- A61P31 12