Patent ID: 6407074
Filing Date: 2002-06-18
Classification: C07H

Abstract:
A compound of the formula or a pharmaceutically acceptable salt thereof, wherein:X is CH(NR9R10), C(O), C(&boxH;NOR9), CH2NR9, or N(C1-C6 alkyl)CH2; R1 is H, hydroxy or methoxy; R2 is hydroxy; R3 is C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, cyano, â€”CH2 S(O)nR8 wherein n is an integer ranging from 0 to 2, â€”CH2OR8, â€”CH2N(OR9)R8, â€”CH2NR8R15, â€”(CH2)m(C6-C10 aryl), or â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4, and wherein the foregoing R3 groups are optionally substituted by 1 to 3 R16 groups; or R2 and R3 are taken together to form an oxazolyl ring as shown below R4 is H, â€”C(O)R9, â€”C(O)OR9, â€”C(O)NR9R10 or a hydroxy protecting group; R5 is â€”SR8, â€”(CH2)nC(O)R8 wherein n is 0 or 1, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, â€”(CH2) m(C6-C10 aryl), or â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4, and wherein the foregoing R5 groups are optionally substituted by 1 to 3 R16 groups; each R6 and R7 is independently H, hydroxy, C1-C6 alkoxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, â€”(CH2)m(C6-C10 aryl), or â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4; each R8 is independently H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, â€”(CH2)qCR11R12(CH2)rNR13R14 wherein q and r are each independently an integer ranging from 0 to 3 except q and r are not both 0, â€”(CH2)m(C6-C10 aryl), or â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4, and wherein the foregoing R8 groups, except H, are optionally substituted by 1 to 3 R16 groups; or where R8 is as â€”CH2NR8R15, R15 and R8 may be taken together to form a 4-10 membered monocyclic or polycyclic saturated ring or a 5-10 membered heteroaryl ring, wherein said saturated and heteroaryl rings optionally include 1 or 2 heteroatoms selected from the group consisting of O, S and â€”N(R8)â€”, in addition to the nitrogen to which R15 and R8 are attached, said saturated ring optionally includes 1 or 2 carbon-carbon double or triple bonds, and said saturated and heteroaryl rings are optionally substituted by 1 to 3 R16 groups; each R9 and R10 is independently H or C1-C6 alkyl; each R11, R12, R13 and R14 is independently selected from the group consisting of H, C1-C10 alkyl, (CH2)m(C6-C10 aryl), and â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4, and wherein the foregoing R11, R12, R13 and R14 groups, except H, are optionally substituted by 1 to 3 R16 groups; or R11 and R13 are taken together to form â€”(CH2)pâ€” wherein p is an integer ranging from 0 to 3 such that a 4-7 membered saturated ring is formed that optionally includes 1 or 2 carbon-carbon double or triple bonds; or R13 and R14 are taken together to form a 4-10 membered monocyclic or polycyclic saturated ring or a 5-10 membered heteroaryl ring, wherein said saturated and heteroaryl rings optionally include 1 or 2 heteroatoms selected from the group consisting of O, S and â€”N(R8)â€”, in addition to the nitrogen to which R13 and R14 are attached, said saturated ring optionally includes 1 or 2 carbon-carbon double or triple bonds, and said saturated and heteroaryl rings are optionally substituted by 1 to 3 R16 groups; R15 is H, C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl, wherein the foregoing R15 groups are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halo and â€”OR9; each R16 is independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R17, â€”C(O)OR17, â€”C(O)OR17, â€”OC(O)OR17, â€”NR6C(O)R7, â€”C(O)NR6R7, â€”NR6R7, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, â€”(CH2)m(C6-C10 aryl), and â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4, and wherein said aryl and heteroaryl substituents are optionally substituted by 1 or 2 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R17, â€”C(O)OR17, â€”C(O)OR17, â€”OC(O)OR17, â€”NR6C(O)R7, â€”C(O)NR6R7, â€”NR6R7, hydroxy, C1-C6 alkyl, and C1-C6 alkoxy; each R17 is independently selected from the group consisting of H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, â€”(CH2)m(C6-C10 aryl), and â€”(CH2)m(5-10 membered heteroaryl), wherein m is an integer ranging from 0 to 4; with the proviso that R8 is not H where R3 is â€”CH2S(O)nR8.