Patent ID: 6403632
Filing Date: 2002-06-11
Classification: C07D

Abstract:
A compound of formula I: or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein;A is selected from COR5, â€”CO2H, CH2CO2H, â€”CO2R6, â€”CONHOH, â€”CONHOR5, â€”CONHOR6, â€”NHRa, â€”N(OH)COR5, â€”SH, â€”CH2SH, â€”SO2NHRa, SN2H2Ra, PO(OH)2, and PO(OH)NHRa; ring B is a 5 membered cyclic amide containing 0-1 additional carbonyl groups and 0-1 double bonds; R1 is Uâ€”Xâ€”Yâ€”Zâ€”Uaâ€”Xaâ€”Yaâ€”Za; U is absent or is selected from: O, NRa, C(O), C(O)O, OC(O), C(O)NRa, NRaC(O), OC(O)O, OC(O)NRa, NRaC(O)O, NRaC(O)NRa, S(O)p, S(O)pNRa, NRaS(O)p, and NRaSO2NRa; X is absent or selected from C1-10 alkylene, C2-10 alkenylene, and C2-10 alkynylene; Y is absent or selected from O, NRa, S(O)p, and C(O); Z is selected from a C3-13 carbocyclic residue substituted with 0-5 Rb and a 5-14 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S and substituted with 0-5 Rb; Ua is absent or is selected from: O, NRa, C(O), C(O)O, OC(O), C(O)NRa, NRaC(O), OC(O)O, OC(O)NRa, NRaC(O)O, NRaC(O)NRa, S(O)p, S(O)pNRa, NRaS(O)p, and NRaSO2NRa; Xa is absent or selected from C1-10 alkylene, C2-10 alkenylene, C2-10 alkynylene; Ya is absent or selected from O, NRa, S(O)p, and C(O); Za is selected from H, a C3-13 carbocyclic residue substituted with 0-5 Rc and a 5-14 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S and substituted with 0-5 Rc; provided that one of Z and Za is a heterocycle and Za is other than quinolinyl; R2 is selected from H, Qâ€², C1-10 alkylene-Qâ€², C2-10 alkenylene-Qâ€², C2-10 alkynylene-Qâ€², (CRRâ€²)râ€²O(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²NRa(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²NRaC(O)(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²C(O)NRa(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²C(O)(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²C(O)O(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²S(O)p(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²SO2NRa(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²NRaC(O)NRa(CRRâ€²)râ€”Qâ€², (CRRâ€²)râ€²OC(O)NRa(CRRâ€²)râ€”Qâ€², and (CRRâ€²)râ€²NRaC(O)O(CRRâ€²)râ€”Qâ€²; R, at each occurrence, is independently selected from H, CH3, CH2CH3, CH&boxH;CH2, CH&boxH;CHCH3, and CH2CH&boxH;CH2; Râ€², at each occurrence, is independently selected from H, CH3, CH2CH3, and CH(CH3)2; Qâ€² is selected from H and a C3-13 carbocyclic residue substituted with 0-5 Rb; R3 is selected from H, Q, C1-10 alkylene-Q, C2-10 alkenylene-Q, C2-10 alkynylene-Q, (CRRâ€²)râ€²O(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRa(CRRâ€²)râ€”Q, (CRRâ€²)rC(O)(CRRâ€²)râ€”Q, (CRRâ€²)rC(O)O(CRRâ€²)rQ, (CRRâ€²)râ€²OC(O) (CRRâ€²)râ€”Q, (CRRâ€²)rC(O)NRa(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRaC(O) (CRRâ€²)râ€”Q, (CRRâ€²)râ€²OC(O)O(CRRâ€²)râ€”Q, (CRRâ€²)râ€²OC(O)NRa(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRaC(O)O(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRaC(O)NRa(CRRâ€²)râ€”Q, (CRRâ€²)râ€²S(O)p(CRRâ€²)râ€”Q, (CRRâ€²)râ€²SO2NRa(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRaSO2(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRaSO2NRa(CRRâ€²)râ€”Q, (CRRâ€²)râ€²NRaC(O) (CRRâ€²)râ€³NHQ, (CRRâ€²)râ€²NRaC(O)(CRRâ€²)rNHC(O)ORa, and (CRRâ€²)râ€²NRaC(O) (CRRâ€²)rNHC(O) (CRRâ€²)rNHC(O)ORa; Q is selected from H and a C3-13 carbocyclic residue substituted with 0-5 Rb; R4 is selected from H, C1-10 alkylene-H, C2-10 alkenylene-H, C2-10 alkynylene-H, (CRRâ€²)râ€²O(CRRâ€²)râ€”H, (CRRâ€²)râ€²NRa(CRRâ€²)râ€”H, (CRRâ€²)râ€²C(O) (CRRâ€²)râ€”H, (CRRâ€²)râ€²C(O)O(CRRâ€²)râ€”H, (CRRâ€²)râ€²OC(O)(CRRâ€²)râ€”H, (CRRâ€²)râ€²C(O)NRa(CRRâ€²)râ€”H, (CRRâ€²)râ€²NRaC(O) (CRRâ€²)râ€”H, (CRRâ€²)râ€²OC(O)O(CRRâ€²)râ€”H, (CRRâ€²)râ€²OC(O)NRa(CRRâ€²)râ€”H, (CRRâ€²)râ€²NRaC(O)O(CRRâ€²)râ€”H, (CRRâ€²)râ€²NRaC(O)NRa(CRRâ€²)râ€”H, (CRRâ€²)râ€²S(O)p(CRRâ€²)râ€”H, (CRRâ€²)râ€²SO2NRa(CRRâ€²)râ€”H, (CRRâ€²)râ€²NRaSO2(CRRâ€²)râ€”H, and (CRRâ€²)râ€²NRaSO2NRa(CRRâ€²)râ€”H; alternatively, R3 and R4 combine to form a C3-13 carbocyclic residue substituted with R1â€² and 0-3 Rb; Ra, at each occurrence, is independently selected from H, C1-4 alkyl, phenyl and benzyl; Raâ€², at each occurrence, is independently selected from H, C1-4 alkyl, phenyl and benzyl; Raâ€³, at each occurrence, is independently selected from H, C1-4 alkyl, benzyl, C3-7 carbocyclic residue, or a 5 to 6 membered heteroaromatic ring containing 1-4 heteroatoms selected from the group consisting of N, O, and S; alternatively, Ra and Raâ€² taken together with the nitrogen to which they are attached form a 5 or 6 membered ring containing from 0-1 additional heteroatoms selected from the group consisting of N, O, and S; Rb, at each occurrence, is independently selected from C1-6 alkyl, ORa, Cl, F, Br, I, &boxH;O, CN, NO2, NRaRaâ€², C(O)Raâ€³, C(O)ORa, C(O)NRaRaâ€², S(O)2NRaRaâ€², S(O)pRa, CF3, and CF2CF3; Rc, at each occurrence, is independently selected from C1-6 alkyl, ORa, Cl, F, Br, I, &boxH;O, CN, NO2, NRaRaâ€², C(O)Ra, C(O)ORa, C(O)NRaRaâ€², NRaC(O)NRaRaâ€², S(O)2NRaRaâ€², S(O)pRa, CF3, CF2CF3, â€”CH(&boxH;NOH), â€”C(&boxH;NOH)CH3, (CRRâ€²)sO(CRRâ€²)sâ€²Rd, (CRRâ€²)sS(O)p(CRRâ€²)sâ€²Rd, (CRRâ€²)sNRa(CRRâ€²)sâ€²Rd, phenyl, and a 5-14 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S; R5, at each occurrence, is selected from C1-10 alkyl substituted with 0-2 Rb, and C1-8 alkyl substituted with 0-2 Rd; Rd, at each occurrence, is independently selected from phenyl substituted with 0-3 Rb, biphenyl substituted with 0-2 Rb, and naphthyl substituted with 0-3 Rb; R6, at each occurrence, is selected from phenyl, naphthyl, C1-10 alkyl-phenyl-C1-6 alkyl-, C3-11 cycloalkyl, C1-6 alkylcarbonyloxy-C1-3 alkyl-, C1-6 alkoxycarbonyloxy-C1-3 alkyl-, C2-10 alkoxycarbonyl, C3-6 cycloalkylcarbonyloxy-C1-3 alkyl-, C3-6 cycloalkoxycarbonyloxy-C1-3 alkyl-, C3-6 cycloalkoxycarbonyl, phenoxycarbonyl, phenyloxycarbonyloxy-C1-3 alkyl-, phenylcarbonyloxy-C1-3 alkyl-, C1-6 alkoxy-C1-6 alkylcarbonyloxy-C1-3 alkyl-, â€”C1-10 alkyl-NR7R7a, â€”CH(R8)OC(&boxH;O)R9, and, â€”CH(R8)OC (&boxH;O)OR9; R7 is selected from H and C1-10 alkyl, C2-6 alkenyl, C3-6 cycloalkyl-C1-3 alkyl-, and phenyl-C1-6 alkyl-; R7a is selected from H and C1-10 alkyl, C2-6 alkenyl, C3-6 cycloalkyl-C1-3 alkyl-, and phenyl-C1-6 alkyl-; R8 is selected from H and C1-4 linear alkyl; R9 is selected from H, C1-8 alkyl substituted with 1-2 Re, C3-8 cycloalkyl substituted with 1-2 Re, and phenyl substituted with 0-2 Rb; Re, at each occurrence, is selected from C1-4 alkyl, C3-8 cycloalkyl, C1-5 alkoxy, phenyl substituted with 0-2 Rb; p, at each occurrence, is selected from 0, 1, and 2; r, at each occurrence, is selected from 0, 1, 2, 3, 4, and 5; râ€², at each occurrence, is selected from 0, 1, 2, 3, 4, and 5; râ€³, at each occurrence, is selected from 1, 2, and 3; s, at each occurrence, is selected from 0, 1, 2 and 3; and, sâ€², at each occurrence, is selected from 0, 1, 2, and 3.