Halogenated biaryl heterocyclic compounds and methods of making and using the same

A method of treating a microbial infection in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the formula:

• or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein:
• A is phenyl;
• B is selected from the group consisting of:
• phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl;
• Het-CH2—R3 is selected from the group consisting of:
• M is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein
• i) any of a)-c) is substituted with one or more moieties selected from the group consisting of F, Cl, Br, and I;
• and
• ii) any of a)-c) optionally is further substituted with one or more R4 groups;
• X is selected from the group consisting of:
• a) —O—, b) —NR5—, c) —N(O), d) —N(OR5)—, e) —S(O)p—, f) —NR5—N═, g) ═N—NR5—, h) —O—N═, i) ═N—O—, j) —N═, k) ═N—, l) —NR5—NR5—, m) —NR5C(O)O—, n) —OC(O)NR5—, o) —NR5C(O)NR5—, p) —NR5C(NR5)NR5—, and
• L is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein any of a)-c) optionally is substituted with one or more R4 groups;
• R1, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R2, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R3 is selected from the group consisting of:
• a) —OR7, b) —NR7R7, c) —C(O)R7, d) —C(O)OR7, e) —OC(O)R7, f) —C(O)NR7R7, g) —NR7C(O)R7, h) —OC(O)NR7R7, i) —NR7C(O)OR7, j) —NR7C(O)NR7R7, k) —C(S)R7, l) —C(S)OR7, m) —OC(S)R7, n) —C(S)NR7R7, o) —NR7C(S)R7, p) —OC(S)NR7R7, q) —NR7C(S)OR7, r) —NR7C(S)NR7R7, s) —NR7C(NR7)NR7R7, t) —S(O)pR7, u) —SO2NR7R7, and v) R7;
• R4, at each occurrence, independently is selected from the group consisting of:
• a) H, b) F, c) Cl, d) Br, e) I, f) ═O, g) ═S, h) ═NR5, i) ═NOR5, j) ═N—NR5R5, k) —CF3, l) —OR5, m) —CN, n) —NO2, o) —NR5R5, p) —C(O)R5, q) —C(O)OR5, r) —OC(O)R5, s) —C(O)NR5R5, t) —NR5C(O)R5, u) —OC(O)NR5R5, v) —NR5C(O)OR5 w) —NR5C(O)NR5R5, x) —C(S)R5, y) —C(S)OR5, z) —OC(S)R5, aa) —C(S)NR5R5, bb) —NR5C(S)R5, cc) —OC(S)NR5R5, dd) —NR5C(S)OR5, ee) —NR5C(S)NR5R5, ff) —NR5C(NR)NR5R5, gg) —S(O)pR5, and hh) R5;
• R5, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) —C(O)—C1-6 alkyl, f) —C(O)—C2-6 alkenyl, g) —C(O)—C2-6 alkynyl, h) —C(O)O—C1-6 alkyl, i) —C(O)O—C2-6 alkenyl, and j) —C(O)O—C2-6 alkynyl,
• wherein any of b)-j) optionally is substituted with one or more R6 groups;
• R6, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, and u) —S(O)pC1-6 alkyl;
• R7, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)C1-6 alkyl, h) —C(O)—C2-6 alkenyl, i) —C(O)—C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more R8 groups;
• R8, at each occurrence, is independently selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) ═O, f) ═S, g) ═NR9, h) ═NOR9, i) ═N—NR9R9, j) —CF3, k) —OR9, l) —CN, m) —NO2, n) —NR9R9, o) —C(O)R9, p) —C(O)OR9, q) —OC(O)R9, r) —C(O)NR9R9, s) —NR9C(O)R9, t) —OC(O)NR9R9, u) —NR9C(O)OR9, v) —NR9C(O)NR9R9, w) —C(S)R9, x) —C(S)OR9, y) —OC(S)R9, z) —C(S)NR9R9, aa) —NR9C(S)R9, bb) —OC(S)NR9R9, cc) —NR9C(S)OR9, dd) —NR9C(S)NR9R9, ee) —NR9C(NR9)NR9R9, ff) —S(O)pR9, gg) —SO2NR9R9, and hh) R9;
• R9, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)—C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more moieties selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, u) —SO2NH2—, v) —SO2NHC1-6 alkyl, w) —SO2N(C1-6 alkyl)2, and x) —S(O)pC1-6 alkyl;
• m is 0, 1, 2, 3, or 4;
• n is 0, 1, 2, 3, or 4;
• and
• p, at each occurrence, independently is 0, 1, or 2.

A method of treating a disorder in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the formula:

• or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein:
• A is phenyl;
• B is selected from the group consisting of:
• phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl;
• Het-CH2—R3 is selected from the group consisting of:
• M is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein
• i) any of a)-c) is substituted with one or more moieties selected from the group consisting of F, Cl, Br, and I;
• and
• ii) any of a)-c) optionally is further substituted with one or more R4 groups;
• X is selected from the group consisting of:
• a) —O, b) —NR5—, c) —N(O), d) —N(OR5)—, e) —S(O)p—, f) —NR5—N═, g) ═N—NR5—, h) —O—N═, i) ═N—O—, j) —N═, k) ═N—, l) —NR5—NR5—, m) —NR5C(O)O—, n) —OC(O)NR5—, o) —NR5C(O)NR5—, p) —NR5C(NR5)NR5—, and
• L is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein any of a)-c) optionally is substituted with one or more R4 groups;
• R1, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7 s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R2, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R3 is selected from the group consisting of:
• a) —OR7, b) —NR7R7, c) —C(O)R7, d) —C(O)OR7, e) —OC(O)R7, f) —C(O)NR7R7, g) —NR7C(O)R7, h) —OC(O)NR7R7, i) —NR7C(O)OR7, j) —NR7C(O)NR7R7, k) —C(S)R7, l) —C(S)OR7, m) —OC(S)R7, n) —C(S)NR7R7, o) —NR7C(S)R7, p) —OC(S)NR7R7, q) —NR7C(S)R7, r) —NR7C(S)NR7R7, s) —NR7C(NR7)NR7R7, t) —S(O)pR7, u) —SO2NR7R7, and v) R7.
• R4, at each occurrence, independently is selected from the group consisting of:
• a) H, b) F, c) Cl, d) Br, e) I, f) ═O, g) ═S, h) ═NR5, i) ═NOR5, j) ═N—NR5R5, k) —CF3, l) —OR5, m) —CN, n) —NO2, o) —NR5R5, p) —C(O)R5, q) —C(O)OR5, r) —OC(O)R5, s) —C(O)NR5R5, t) —NR5C(O)R5, u) —OC(O)NR5R5, v) —NR5C(O)OR5, w) —NR5C(O)NR5R5, x) —C(S)R5, y) —C(S)OR5, z) —OC(S)R5, aa) —C(S)NR5R5, bb) —NR5C(S)R5, cc) —OC(S)NR5R5, dd) —NR C(S)OR5, ee) —NR C(S)NR5R5, ff) —NR5C(NR5)NR5R5, gg) —S(O)pR5, and hh) R5;
• R5, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) —C(O)C1-6 alkyl, f) —C(O)—C2-6 alkenyl, g) —C(O)—C2-6 alkynyl, h) —C(O)O—C1-6 alkyl, i) —C(O)O—C2-6 alkenyl, and j) —C(O)O—C2-6 alkynyl,
• wherein any of b)-j) optionally is substituted with one or more R6 groups;
• R6, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, and u) —S(O)pC1-6 alkyl;
• R7, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more R8 groups;
• R8, at each occurrence, is independently selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) ═O, f) ═S, g) ═NR9, h) ═NOR9, i) ═N—NR9R9, j) —CF3, k) —OR9, l) —CN, m) —NO2, n) —NR9R9, o) —C(O)R9, p) —C(O)OR9, q) —OC(O)R9, r) —C(O)NR9R9, s) —NR9C(O)R9, t) —OC(O)NR9R9, u) —NR9C(O)OR9, v) —NR9C(O)NR9R9, w) —C(S)R9, x) —C(S)OR9, y) —OC(S)R9, z) —C(S)NR9R9, aa) —NR9C(S)R9, bb) —OC(S)NR9R9, cc) —NR9C(S)OR9, dd) —NR9C(S)NR9R9, ee) —NR9C(NR9)NR9R9, ff) —S(O)pR9, gg) —SO2NR9R9, and hh) R9;
• R9, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)—C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more moieties selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, u) —SO2NH2—, v) —SO2NHC1-6 alkyl, w) —SO2N(C1-6 alkyl)2, and x) —S(O)pC1-6 alkyl;
• m is 0, 1, 2, 3, or 4;
• n is 0, 1, 2, 3, or 4;
• and
• p, at each occurrence, independently is 0, 1, or 2;
• thereby to ameliorate a symptom of the disorder, wherein the disorder is selected from the group consisting of:
• a skin infection, nosocomial pneumonia, post-viral pneumonia, an abdominal infection, a urinary tract infection, bacteremia, septicemia, endocarditis, an atrio-ventricular shunt infection, a vascular access infection, meningitis, surgical prophylaxis, a peritoneal infection, a bone infection, a joint infection, a methicillin-resistant Staphylococcus aureus infection, a vancomycin-resistant Enterococci infection, a linezolid-resistant organism infection, and tuberculosis.

A method of treating a microbial infection in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the formula:

• or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein:
• A is phenyl;
• B is selected from the group consisting of:
• phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl;
• Het-CH2—R3 is selected from the group consisting of:
• M is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein
• i) any of a)-c) is substituted with one or more moieties selected from the group consisting of F, Cl, Br, and I;
• and
• ii) any of a)-c) optionally is further substituted with one or more R4 groups;
• X is selected from the group consisting of:
• a) —O—, b) —NR5—, c) —N(O), d) —N(OR5)—, e) —S(O)p—, f) —NR5—N═, g) ═N—NR5—, h) —O—N═, i) ═N—O—, j) —N═, k) ═N—, l) —NR5—NR5—, m) —NR5C(O)O—, n) —OC(O)NR5—, o) —NR5C(O)NR5—, p) —NR5C(NR5)NR5—, and
• L is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein any of a)-c) optionally is substituted with one or more R4 groups;
• R1, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R2, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R3 is selected from the group consisting of:
• a) —NR7R7, b) —C(O)R7, c) —C(O)OR7, d) —OC(O)R7, e) —C(O)NR7R7, f) —NR7C(O)R7, g) —OC(O)NR7R7, h) —NR7C(O)OR7, i) —NR7C(O)NR7R7, j) —C(S)R7, k) —C(S)OR7, l) —OC(S)R7, m) —C(S)NR7R7, n) —NR7C(S)R7, o) —OC(S)NR7R7, p) —NR7C(S)OR7, q) —NR7C(S)NR7R7, r) —NR7C(NR7)NR7R7, s) —SOR7, t) —SO2R7, u) —SO2NR7R7, and v) R7;
• R4, at each occurrence, independently is selected from the group consisting of:
• a) H, b) F, c) Cl, d) Br, e) I, f) ═O, g) ═S, h) ═NR5, i) ═NOR5, j) ═N—NR5R5, k) —CF3, l) —OR5, m) —CN, n) —NO2, o) —NR5R5, p) —C(O)R5, q) —C(O)OR5, r) —OC(O)R5, s) —C(O)NR5R5, t) —NR5C(O)R5, u) —OC(O)NR5R5, v) —NR5C(O)OR5, w) —NR5C(O)NR5R5, x) —C(S)R5, y) —C(S)OR5, z) —OC(S)R5, aa) —C(S)NR5R5, bb) —NR5C(S)R5, cc) —OC(S)NR5R5, dd) —NR5C(S)OR5, ee) —NR5C(S)NR5R5, ff) —NR5C(NR5)NR5R5, gg) —S(O)pR5, and hh) R5;
• R5, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) —C(O)C1-6 alkyl, f) —C(O)C2-6 alkenyl, g) —C(O)—C2-6 alkynyl, h) —C(O)O—C1-6 alkyl, i) —C(O)O—C2-6 alkenyl, and j) —C(O)O—C2-6 alkynyl,
• wherein any of b)-j) optionally is substituted with one or more R6 groups;
• R6, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, and u) —S(O)pC1-6 alkyl;
• R7, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more R8 groups;
• R8, at each occurrence, is independently selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) ═O, f) ═S, g) ═NR9, h) ═NOR9, i) ═N—NR9R9, j) —CF3, k) —OR9, l) —CN, m) —NO2, n) —NR9R9, o) —C(O)R9, p) —C(O)OR9, q) —OC(O)R9, r) —C(O)NR9R9, s) —NR9C(O)R9, t) —OC(O)NR9R9, u) —NR9C(O)OR9, v) —NR9C(O)NR9R9, w) —C(S)R9, x) —C(S)OR9, y) —OC(S)R9, z) —C(S)NR9R9, aa) —NR9C(S)R9, bb) —OC(S)NR9R9, cc) —NR9C(S)OR9, dd) —NR9C(S)NR9R9, ee) —NR9C(NR9)NR9R9, ff) —S(O)pR9, gg) —SO2NR9R9, and hh) R9;
• R9, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)—C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more moieties selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, u) —SO2NH2—, v) —SO2NHC1-6 alkyl, w) —SO2N(C1-6 alkyl)2, and x) —S(O)pC1-6 alkyl;
• m is 0, 1, 2, 3, or 4;
• n is 0, 1, 2, 3, or 4;
• and
• p, at each occurrence, independently is 0, 1, or 2.

A method of treating a disorder in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the formula:

• or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein:
• A is phenyl;
• B is selected from the group consisting of:
• phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl;
• Het-CH2—R3 is selected from the group consisting of:
• M is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein
• i) any of a)-c) is substituted with one or more moieties selected from the group consisting of F, Cl, Br, and I;
• and
• ii) any of a)-c) optionally is further substituted with one or more R4 groups;
• X is selected from the group consisting of:
• a) —O—, b) —NR5—, c) —N(O), d) —N(OR5)—, e) —S(O)p—, f) —NR5—N═, g) ═N—NR5—, h) —O—N═, i) ═N—O—, j) —N═, k) ═N—, l) —NR5—NR5—, m) —NR5C(O)O—, n) —OC(O)NR5—, o) —NR5C(O)NR5—, p) —NR5C(NR5)NR5—, and
• L is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein any of a)-c) optionally is substituted with one or more R4 groups;
• R1, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R2, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7, R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R3 is selected from the group consisting of:
• a) —NR7R7, b) —C(O)R7, c) —C(O)OR7, d) —OC(O)R7, e) —C(O)NR7R7, f) —NR7C(O)R7, g) —OC(O)NR7R7, h) —NR7C(O)OR7, i) —NR7C(O)NR7R7, j) —C(S)R7, k) —C(S)OR7, l) —OC(S)R7, m) —C(S)NR7R7, n) —NR7C(S)R7, o) —OC(S)NR7R7, p) —NR7C(S)OR7, q) —NR7C(S)NR7R7, r) —NR7C(NR7)NR7R7, s) —SOR7, t) —SO2R7, u) —SO2NR7R7, and v) R7;
• R4, at each occurrence, independently is selected from the group consisting of:
• a) H, b) F, c) Cl, d) Br, e) I, f) ═O, g) ═S, h) ═NR5, i) ═NOR5, j) ═N—NR5R5, k) —CF3, l) —OR5, m) —CN, n) —NO2, o) —NR5R5, p) —C(O)R5, q) —C(O)OR5, r) —OC(O)R5, s) —C(O)NR5R5, t) —NR5C(O)R5, u) —OC(O)NR5R5, v) —NR5C(O)OR5, w) —NR5C(O)NR5R5, x) —C(S)R5, y) —C(S)OR5, z) —OC(S)R5, aa) —C(S)NR5R5, bb) —NR5C(S)R5, cc) —OC(S)NR5R5, dd) —NR5C(S)OR5, ee) —NR5C(S)NR5R5, ff) —NR5C(NR5)NR5R5, gg) —S(O)pR5, and hh) R5;
• R5, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) —C(OC1-6 alkyl, f) —C(O)C2-6 alkenyl, g) —C(O)C2-6 alkynyl, h) —C(O)O—C1-6 alkyl, i) —C(O)O—C2-6 alkenyl, and j) —C(O)O—C2-6 alkynyl,
• wherein any of b)-j) optionally is substituted with one or more R6 groups;
• R6, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, and u) —S(O)pC1-6 alkyl;
• R7, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more R8 groups;
• R8, at each occurrence, is independently selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) ═O, f) ═S, g) ═NR9, h) ═NOR9, i) ═N—NR9R9, j) —CF3, k) —OR9, l) —CN, m) —NO2, n) —NR9R9, o) —C(O)R9, p) —C(O)OR9, q) —OC(O)R9, r) —C(O)NR9R9, s) —NR9C(O)R9, t) —OC(O)NR9R9, u) —NR9C(O)OR9, v) —NR9C(O)NR9R9, w) —C(S)R9, x) —C(S)OR9, y) —OC(S)R9, z) —C(S)NR9R9, aa) —NR9C(S)R9, bb) —OC(S)NR9R9, cc) —NR9C(S)OR9, dd) —NR9C(S)NR9R9, ee) —NR9C(NR9)NR9R9, ff) —S(O)pR9, gg) —SO2NR9R9, and hh) R9;
• R9, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)—C1-6 alkyl, h) —C(O)—C2-6 alkenyl, i) —C(O)—C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more moieties selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, u) —SO2NH2—, v) —SO2NHC1-6 alkyl, w) —SO2N(C1-6 alkyl)2, and x) —S(O)pC1-6 alkyl;
• m is 0, 1, 2, 3, or 4;
• n is 0, 1, 2, 3, or 4;
• and
• p, at each occurrence, independently is 0, 1, or 2;
• thereby to ameliorate a symptom of the disorder, wherein the disorder is selected from the group consisting of:
• a skin infection, nosocomial pneumonia, post-viral pneumonia, an abdominal infection, a urinary tract infection, bacteremia, septicemia, endocarditis, an atrio-ventricular shunt infection, a vascular access infection, meningitis, surgical prophylaxis, a peritoneal infection, a bone infection, a joint infection, a methicillin-resistant Staphylococcus aureus infection, a vancomycin-resistant Enterococci infection, a linezolid-resistant organism infection, and tuberculosis.

A method of treating a microbial infection in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the formula:

• or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein:
• A is phenyl;
• B is selected from the group consisting of:
• phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl;
• Het-CH2—R3 is selected from the group consisting of:
• M is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein
• i) any of a)-c) is substituted with one or more moieties selected from the group consisting of F, Cl, Br, and I;
• and
• ii) any of a)-c) optionally is further substituted with one or more R4 groups;
• X is selected from the group consisting of:
• a) —O—, b) —NR5—, c) —N(O)—, d) —N(OR5)—, e) —S(O)p—, f) —NR5—N═, g) ═N—NR5—, h) —O—N═, i) ═N—O—, j) —N═, k) ═N—, l) —NR5—NR5—, m) —NR5C(O)O—, n) —OC(O)NR5—, o) —NR5C(O)NR5—, p) —NR5C(NR5)NR5—, and
• L is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein any of a)-c) optionally is substituted with one or more R4 groups;
• R1, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R2, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R3 is selected from the group consisting of:
• a) —OR7, b) —NR7R7, c) —C(O)R7, d) —C(O)OR7, e) —OC(O)R7, f) —C(O)NR7R7, g) —NR7C(O)R7, h) —OC(O)NR7R7, i) —NR7C(O)OR7, j) —NR7C(O)NR7R7, k) —C(S)R7, l) —C(S)OR7, m) —OC(S)R7, n) —C(S)NR7R7, o) —NR7C(S)R7, p) —OC(S)NR7R7, q) —NR7C(S)OR7, r) —NR7C(S)NR7R7, s) —NR7C(NR7)NR7R7, t) —S(O)pR7, u) —SO2NR7R7, and v) R7;
• R4, at each occurrence, independently is selected from the group consisting of:
• a) H, b) F, c) Cl, d) Br, e) I, f) ═O, g) ═S, h) ═NR5, i) ═NOR5, j) ═N—NR5R5, k) —CF3, l) —OR5, m) —CN, n) —NO2, o) —NR5R5, p) —C(O)R5, q) —C(O)OR5, r) —OC(O)R5, s) —C(O)NR5R5, t) —NR5C(O)R5, u) —OC(O)NR5R5, v) —NR5C(O)OR5, w) —NR5C(O)NR5R5, x) —C(S)R5, y) —C(S)OR5, z) —OC(S)R5, aa) —C(S)NR5R5, bb) —NR5C(S)R5, cc) —OC(S)NR5R5, dd) —NR5C(S)OR5, ee) —NR5C(S)NR5R5, ff) —NR5C(NR5)NR5R5, gg) —S(O)pR5, and hh) R5;
• R5, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) —C(OC1-6 alkyl, f) —C(O)C2-6 alkenyl, g) —C(O)—C2-6 alkynyl, h) —C(O)O—C1-6 alkyl, i) —C(O)O—C2-6 alkenyl, and j) —C(O)O—C2-6 alkynyl,
• wherein any of b)-j) optionally is substituted with one or more R6 groups;
• R6, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, and u) —S(O)pC1-6 alkyl;
• R7, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more R8 groups;
• R8, at each occurrence, is independently selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) ═0, f) ═S, g) ═NR9, h) ═NOR9, i) ═N—NR9R9, j) —CF3, k) —OR9, l) —CN, m) —NO2, n) —NR9R9, o) —C(O)R9, p) —C(O)OR9, q) —OC(O)R9, r) —C(O)NR9R9, s) —NR9C(O)R9, t) —OC(O)NR9R9, u) —NR9C(O)OR9, v) —NR9C(O)NR9R9, w) —C(S)R9, x) —C(S)OR9, y) —OC(S)R9, z) —C(S)NR9R9, aa) —NR9C(S)R9, bb) —OC(S)NR9R9, cc) —NR9C(S)OR9, dd) —NR9C(S)NR9R9, ee) —NR9C(NR9)NR9R9, ff) —S(O)pR9, gg) —SO2NR9R9, and hh) R9;
• R9, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)—C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more moieties selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, u) —SO2NH2—, v) —SO2NHC1-6 alkyl, w) —SO2N(C1-6 alkyl)2, and x) —S(O)pC1-6 alkyl;
• m is 0, 1, 2, 3, or 4;
• n is 0, 1, 2, 3, or 4;
• and
• p, at each occurrence, independently is 0, 1, or 2.

A method of treating a disorder in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the formula:

• or a pharmaceutically acceptable salt, ester or prodrug thereof, wherein:
• A is phenyl;
• B is selected from the group consisting of:
• phenyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl;
• Het-CH2—R3 is selected from the group consisting of:
• M is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein
• i) any of a)-c) is substituted with one or more moieties selected from the group consisting of F, Cl, Br, and I;
• and
• ii) any of a)-c) optionally is further substituted with one or more R4 groups;
• X is selected from the group consisting of:
• a) —, b) —NR5—, c) —N(O)—, d) —N(OR5)—, e) —S(O)p—, f) —NR5—N═, g) ═N—NR5—, h) —O—N═, i) ═N—O—, j) —N═, k) ═N—, l) —NR5—NR5—, m) —NR5C(O)O—, n) —OC(O)NR5—, o) —NR5C(O)NR5—, p) —NR5C(NR5)NR5—, and
• L is selected from the group consisting of:
• a) C1-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
• wherein any of a)-c) optionally is substituted with one or more R4 groups;
• R1, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R2, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OR7, g) —CN, h) —NO2, i) —NR7R7, j) —C(O)R7, k) —C(O)OR7, l) —OC(O)R7, m) —C(O)NR7R7, n) —NR7C(O)R7, o) —OC(O)NR7R7, p) —NR7C(O)OR7, q) —NR7C(O)NR7R7, r) —C(S)R7, s) —C(S)OR7, t) —OC(S)R7, u) —C(S)NR7R7, v) —NR7C(S)R7, w) —OC(S)NR7R7, x) —NR7C(S)OR7, y) —NR7C(S)NR7R7, z) —NR7C(NR7)NR7R7, aa) —S(O)pR7, bb) —SO2NR7R7, and cc) R7;
• R3 is selected from the group consisting of:
• a) —OR7, b) —NR7R7, c) —C(O)R7, d) —C(O)OR7, e) —OC(O)R7, f) —C(O)NR7R7, g) —NR7C(O)R7, h) —OC(O)NR7R7, i) —NR7C(O)OR7, j) —NR7C(O)NR7R7, k) —C(S)R7, l) —C(S)OR7, m) —OC(S)R7, n) —C(S)NR7R7, o) —NR7C(S)R7, p) —OC(S)NR7R7, q) —NR7C(S)OR7, r) —NR7C(S)NR7R7, s) —NR7C(NR7)NR7R7, t) —S(O)pR7, u) —SO2NR7R7, and v) R7;
• R4, at each occurrence, independently is selected from the group consisting of:
• a) H, b) F, c) Cl, d) Br, e) I, f) ═O, g) ═S, h) ═NR5, i) ═NOR5, j) ═N—NR5R5, k) —CF3, l) —OR5, m) —CN, n) —NO2, o) —NR5R5, p) —C(O)R5, q) —C(O)OR5, r) —OC(O)R5, s) —C(O)NR5R5, t) —NR5C(O)R5, u) —OC(O)NR5R5, v) —NR5C(O)OR5, w) NR5C(O)NR5R5, x) —C(S)R5, y) —C(S)OR5, z) —OC(S)R5, aa) —C(S)NR5R5, bb) —NR5C(S)R5, cc) —OC(S)NR5R5, dd) —NR5C(S)OR5, ee) —NR5C(S)NR5R5, ff) —NR5C(NR5)NR5R5, gg) —S(O)pR5, and hh) R5;
• R5, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) —C(O)C1-6 alkyl, f) —C(O)—C2-6 alkenyl, g) —C(O)—C2-6 alkynyl, h) —C(O)O—C1-6 alkyl, i) —C(O)O—C2-6 alkenyl, and j) —C(O)O—C2-6 alkynyl,
• wherein any of b)-j) optionally is substituted with one or more R6 groups;
• R6, at each occurrence, independently is selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, and u) —S(O)pC1-6 alkyl;
• R7, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more R8 groups;
• R8, at each occurrence, is independently selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) ═O, f) ═S, g) ═NR9, h) ═NOR9, i) ═N—NR9R9, j) —CF3, k) —OR9, l) —CN, m) —NO2, n) —NR9R9, o) —C(O)R9, p) —C(O)OR9, q) —OC(O)R9, r) —C(O)NR9R9, s) —NR9C(O)R9, t) —OC(O)NR9R9, u) —NR9C(O)OR9, v) —NR9C(O)NR9R9, w) —C(S)R9, x) —C(S)OR9, y) —OC(S)R9, z) —C(S)NR9R9, aa) —NR9C(S)R9, bb) —OC(S)NR9R9, cc) —NR9C(S)OR9, dd) —NR9C(S)NR9R9, ee) —NR9C(NR9)NR9R9, ff) —S(O)pR9, gg) —SO2NR9R9, and hh) R9;
• R9, at each occurrence, independently is selected from the group consisting of:
• a) H, b) C1-6 alkyl, c) C2-6 alkenyl, d) C2-6 alkynyl, e) C3-14 saturated, unsaturated, or aromatic carbocycle, f) 3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, g) —C(O)—C1-6 alkyl, h) —C(O)C2-6 alkenyl, i) —C(O)C2-6 alkynyl, j) —C(O)—C3-14 saturated, unsaturated, or aromatic carbocycle, k) —C(O)-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, l) —C(O)O—C1-6 alkyl, m) —C(O)O—C2-6 alkenyl, n) —C(O)O—C2-6 alkynyl, o) —C(O)O—C3-14 saturated, unsaturated, or aromatic carbocycle, and p) —C(O)O-3-14 membered saturated, unsaturated, or aromatic heterocycle consisting of one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur,
• wherein any of b)-p) optionally is substituted with one or more moieties selected from the group consisting of:
• a) F, b) Cl, c) Br, d) I, e) —CF3, f) —OH, g) —OC1-6 alkyl, h) —SH, i) —SC1-6 alkyl, j) —CN, k) —NO2, l) —NH2, m) —NHC1-6 alkyl, n) —N(C1-6 alkyl)2, o) —C(O)C1-6 alkyl, p) —C(O)OC1-6 alkyl, q) —C(O)NH2, r) —C(O)NHC1-6 alkyl, s) —C(O)N(C1-6 alkyl)2, t) —NHC(O)C1-6 alkyl, u) —SO2NH2—, v) —SO2NHC1-6 alkyl, w) —SO2N(C1-6 alkyl)2, and x) —S(O)pC1-6 alkyl;
• m is 0, 1, 2, 3, or 4;
• n is 0, 1, 2, 3, or 4;
• and
• p, at each occurrence, independently is 0, 1, or 2;
• thereby to ameliorate a symptom of the disorder, wherein the disorder is selected from the group consisting of:
• a skin infection, nosocomial pneumonia, post-viral pneumonia, an abdominal infection, a urinary tract infection, bacteremia, septicemia, endocarditis, an atrio-ventricular shunt infection, a vascular access infection, meningitis, surgical prophylaxis, a peritoneal infection, a bone infection, a joint infection, a methicillin-resistant Staphylococcus aureus infection, a vancomycin-resistant Enterococci infection, a linezolid-resistant organism infection, and tuberculosis.

A method of treating a microbial infection in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the structure corresponding to any one of the compounds listed below:

• Compound
• Number
• Structure
• 1
• 2
• 3
• 4
• 5
• 6
• 7
• 8
• 9
• 10
• 11
• 12
• 13
• 14
• 15
• 16
• 17
• 18
• 19
• 20
• 21
• 22
• 23
• 24
• 25
• 26
• 27
• 28
• 29
• 30
• 31
• 32
• 33
• 34
• 35
• 36
• 37
• 38
• 39
• 40
• 41
• 42
• 43
• 44
• 45
• 46
• 47
• 48
• 49
• 50
• 51
• 52
• 53
• 54
• 55
• 56
• 57
• 58
• 59
• 60
• 61
• 62
• 63
• 64
• 65
• 66
• 67
• 68
• 69
• 70
• 71
• 72
• 73
• 74
• 75
• 76
• 77
• 78
• 79
• 80
• 81
• 82
• or a pharmaceutically acceptable salt, ester or prodrug thereof.

A method of treating a disorder in a mammal comprising the step of administering to the mammal an effective amount of one or more compounds having the structure corresponding to any one of the compounds listed below:

• Compound
• Number
• Structure
• 1
• 2
• 3
• 4
• 5
• 6
• 7
• 8
• 9
• 10
• 11
• 12
• 15
• 16
• 17
• 18
• 19
• 20
• 21
• 22
• 23
• 24
• 25
• 26
• 27
• 28
• 29
• 30
• 31
• 32
• 33
• 34
• 35
• 36
• 37
• 38
• 39
• 40
• 41
• 42
• 43
• 44
• 45
• 46
• 47
• 48
• 49
• 50
• 51
• 52
• 53
• 54
• 55
• 56
• 57
• 58
• 59
• 60
• 61
• 62
• 63
• 64
• 65
• 66
• 67
• 68
• 69
• 70
• 71
• 72
• 73
• 74
• 75
• 76
• 77
• 78
• 79
• 80
• 81
• 82
• or a pharmaceutically acceptable salt, ester or prodrug thereof,
• thereby to ameliorate a symptom of the disorder, wherein the disorder is selected from the group consisting of:
• a skin infection, nosocomial pneumonia, post-viral pneumonia, an abdominal infection, a urinary tract infection, bacteremia, septicemia, endocarditis, an atrio-ventricular shunt infection, a vascular access infection, meningitis, surgical prophylaxis, a peritoneal infection, a bone infection, a joint infection, a methicillin-resistant Staphylococcus aureus infection, a vancomycin-resistant Enterococci infection, a linezolid-resistant organism infection, and tuberculosis.