Antimicrobial compounds and methods of making and using the same

Claim 1: A compound having formula (1), (2), (3) or (4) where -GHJ, alternatively, is selected from the rest of formula (5), where each H and J is independently selected , or -GHJ is selected from the remainder of formula (6), where Rx is selected from CH2, NH, N (C1-8 alkyl), S, or O; Ry and Rz are C or CH, where each is independently substituted with one or more F, CH3, CF3, OH and OCH3; or Rx, Ry and Rz are independently selected from CH2 or CRaRb where Ra and Rb are taken together to form a C1-5 carbocycle; J is selected from NH2, NH (C1-8 alkyl), N (C1-8 alkyl) 2, NHC (= O) CH3, NHC (= O) NH2, NHC (= NH) NH2, NHC (= NH) H ; where n is 0; 1 or 2; alternatively, -GHJ is selected from the rest of formula (7) where Rx is selected from CH2, NH, N (C1-8 alkyl), S or O; Rz is a C or CH, substituted with one or more CH3, or Rz is CRaRb where Ra and Rb are taken together to form a C1-5 carbocycle; where m is 1; 2 or 3; J is selected from NH2, NH (C1-8 alkyl), N (C1-8 alkyl) 2, NHC (= O) CH3, NHC (= O) NH2, NHC (= NH) NH2, NHC (= NH) H ; CBA-, -DEF and -GHJ are chemical residues, where: A, D and G are independently selected from the group consisting of: (a) a single bond, (b) - (C1-8 alkyl) -, ( c) - (C2-8 alkenyl) -, (d) - (C2-8 alkynyl) -, where: i) 0 - 4 carbon atoms in any of (b) - (d) immediately above are optionally replaced by a moiety selected from the group consisting of -O-, -S (O) p-, -NR6-, - (C = O) -, -S (O) pNR6-, -NR6S (O) p- and -NR6S ( O) pNR6-; ii) any of (b) - (d) immediately above is optionally substituted with one or more R5 groups; and iii) any of (b) - (d) immediately above is optionally substituted with - (C1-8-alkyl) -R5 groups; (e) -O-, (f) -NR6-, (g) -S (O) p-, (h) -C (O) -, (i) -C (O) O-, j) -OC (O) -, k) -OC (O) O-, (l) -C (O) NR6-, (m) -NR6CO-, (n) -NR6C (O) NR6-, (o) -C ( = NR6) -, (p) -C (= NR6) O-, (q) -OC (= NR6) -, (r) -C (= NR6) NR6-, (s) -NR6C (= NR6) - , (t) -C (= S) -, (u) -C (= S) NR6-, (v) -NR6C (= S) -, (w) -C (O) S-, (x) - SC (O) -, (y) -OC (= S) -, (z) -C (= S) O-, (aa) -NR6 (CNR6) NR6-, (bb) -CR6R6C (O) -, (cc) -C (O) NR6 (CR6R6) t -, (dd) a saturated, unsaturated 3-14 membered heterocycle, or aromatic containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; (ee) a saturated, unsaturated or aromatic 3-14 membered carbocycle; and (ff) - (CR6R6) t-; where (dd) or (ee) is optionally substituted with one or more R5 groups; B, E and H are independently selected from the group consisting of: (a) a single bond; (b) a saturated, unsaturated or aromatic 3-14 membered heterocycle, containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; (c) a saturated, unsaturated or aromatic 3-14 membered carbocycle; where (b) or (c) is optionally substituted with one or more R5 groups; (d) - (C1-8 alkyl) -, (e) - (C2-8 alkenyl) -, (f) - (C2-8 alkynyl) -, where: i) 0 - 4 carbon atoms in any of ( d) - (f) immediately above are optionally replaced by a residue selected from the group consisting of -O-, -S (O) p-, -NR6-, - (C = O) -, -C (= NR6) -, -S (O) pNR6-, -NR6S (O) p- and -NR6S (O) pNR6-; ii) any of (d) - (f) immediately above is optionally substituted with one or more R5 groups; and iii) any of (d) - (f) immediately above is optionally substituted with - (C1-8-alkyl) -R5 groups; and (g) - (CR6R6) t-; C, F and J are selected independently from the group consisting of: (a) hydrogen, (c) F, (d) Cl, (e) Br, (f) I, (g) -CF3, (h) -CN, (i) -N3, (j) -NO2, ( k) -NR6 (CR6R6) tR8, (l) -OR8, (m) -S (O) p (CR6R6) tR8, (n) -C (O) (CR6R6) tR8, (o) -OC (O) (CR6R6) tR8, (p) -SC (O) (CR6R6) tR8, (q) -C (O) O (CR6R6) tR8, (r) -NR6C (O) (CR6R6) tR8, (s) -C (O) NR6 (CR6R6) tR8, (t) -C (= NR6) (CR6R6) tR8, (u) -C (= NNR6R6) (CR6R6) tR8, (v) -C (= NNR6C (O) R6) (CR6R6) tR8, (w) -C (= NOR8) (CR6R6) tR8, (x) -NR6C (O) O (CR6R6) tR8, (y) -OC (O) NR6 (CR6R6) tR8, (z) -NR6C (O) NR6 (CR6R6) tR8, (aa) -NR6S (O) p (CR6R6) tR8, (bb) -S (O) pNR6 (CR6R6) tR8, (cc) -NR6S (O) pNR6 (CR6R6) tR8, (dd) -NR6R8, (ee) -NR6 (CR6R6) R8, (ff) -OH, (gg) -NR8R8, (hh) -OCH3, (ii) -S (O) pR8, (jj) -NC (O) R8, (kk) -NR6C (NR6) NR6R8, (II) a C1- alkyl group 8, (mm) a C2-8 alkenyl group, (nn) a C2-8 alkynyl group, (oo) a saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen , oxygen and sulfur, (pp) a saturated, unsaturated 3-14 membered carbocycle, or aromatic, (qq) - (CR6R6) tNR6 (CR6R6) tR8, (rr) -N [(CR6R6) tR8] [C = O (CR6R6) tR8], (ss) - (CR6R6) tN [(CR6R6) tR8 ] [(CR6R6) tR8], (tt) - (CR6R6) tNR6 (C = O) (CR6R6) tR8, (uu) -haloalkyl, (vv) -C (O) (CR6) [(CR6R6) tR8] R8 , (ww) - (CR6R6) tC (O) NR8R8, (xx) - (CR6R6) tC (O) O (CR6R6) tR8, (yy) -NR6C (O) CR8R8R8, (zz) -N [(CR6R6) tR8] C (O) R8 and (aaa) -S (O) pNR8R8; where (II) to (pp) are optionally substituted with one or more R7 groups; R5 is selected from (a) hydrogen, (b) F, (e) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3 (i) - NO2, (j) -NR6R6, (k) -OR8, (l) -NR6 (CNR6) NR6R6, (m) -C1-8 alkyl, (n) -C1-8 alkenyl, (o) -C1-8 alkynyl , (p) - (C1-8 alkyl) - (saturated, unsaturated, or aromatic 3-14 membered heterocycle, containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur), (q) - ( C1-8alkyl) - (saturated, unsaturated, or aromatic 3-14 membered carbocycle), (r) -haloalkyl, (s) -SR6, (t) -saturated, unsaturated, or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and (u) saturated, unsaturated, or aromatic 3-14 membered carbocycle; alternatively, two R5 groups are taken together to form a carbocycle; where (m) to (r) and (t) to (u) are optionally substituted with one or more R8; R6 is selected from (a) hydrogen, (b) -C1-8alkyl, or alternatively, two R6 groups are taken together to form a carbocycle, (c) -haloalkyl, (d) -saturated 3-14 membered heterocycle, unsaturated, or aromatic containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur; and (e) 3-14 membered saturated, unsaturated, or aromatic carbocycle; where (b) to (e) are optionally substituted with one or more R8; R7 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R6, (k) -OR6, (l) -NR6 (CNR) NR6R6, (m) -C1-8alkyl, (n) -C1-8alkenyl, (o) -C1-alkynyl 8, (p) - (C1-8 alkyl) - (saturated, unsaturated, or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur), (q) - ( C1-8alkyl) - (saturated, unsaturated, or aromatic 3-14 membered carbocycle), (r) -haloalkyl, (s) -NR6R8, (t) -OR8, (u) - (CR6R6) tNR6R8, (v) -CR6R8R8, (w) -SR6, (x) -saturated 3-14 membered heterocycle , unsaturated, or aromatic, containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (y) saturated, unsaturated or aromatic 3-14 membered carbocycle ((z) - (CR6R6) tC (O ) NR8R8, (aa) -S (O) pR8, (bb) -NR6C (O) NR6R6, (cc) -NR6C (O) R6, and (dd) -C (= NR6) NR6R6; where (m) to (q) and (x) to (y) are optionally substituted with one or more R9; R8 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R9, (k) -OR9, (l) -NR6 (CNR6) NR6R6, (m) -C1-8alkyl, (n) -C1-8alkenyl, (o) -C1-alkynyl 8, (p) - (C1-8 alkyl) - (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) - (alkyl C1-8) - (saturated, unsaturated or aromatic 3-14 membered carbocycle), (r) saturated, unsaturated, or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, (s) 3- saturated, unsaturated, or aromatic 3-14 membered carbocycle, (t) -haloalkyl, (u) -C (O) (CR6R6) tR9, (v) -SR6, (w) -OC (O) (CR6R6) tR9, (x) -NR6C (O) NR6R9, (y ) -NR6C (O) R9, (z) -NR6 (CNR9) (NR6R6), (aa) -ONR6 (CNR6) NR6R6, (bb) -C (= NR9) NR6R6, (cc) -S (O) pR9 , (dd) - (CR6R6) tC (O) NR6R9, (ee) - (CR6R6) tOR9 and (ff) - (CR6R6) tNR6R9; where (m) to (s) are optionally substituted with one or more R9; R9 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R10, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C (O) (CR6R6) tNR6R6, (n) -C1-8 alkyl, (o) -C1-4alkenyl, (p) C1-8alkynyl, (q) -saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) saturated, unsaturated or aromatic 3-14 membered carbocycle (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R10, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR10, (y) -S (O) pR6, (z) - (C1-8 alkyl) - (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa) - (C1-8 alkyl) - (saturated, unsaturated or aromatic 3-14 membered carbocycle), (bb) -O (CR6R6) tOR6, (cc) -C (= NR6) NR6R6, (dd) -ONR6R6, ( ee) -NR6C (O) NR6R6, (ff) -O (CR6R6) tOR6, (gg) -NR6C (O) R6 and (hh) - (CR6R6) tNR6R10; where (n) to (r) and (z) to (aa) are optionally substituted with one or more R10; R10 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R6, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C (O) (CR6R6) tNR6R6, (n) -C1-8 alkyl, (o) -C1-8alkenyl, (p) -C1-8alkynyl, (q) -saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r ) saturated, unsaturated or aromatic 3-14 membered carbocycle (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R6, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR6, (y) -S (O) pR6, (z) - (C1-8 alkyl) - (heterocyc