Patent ID: 6518251
Filing Date: 2003-02-11
Classification: A61P,C07H

Abstract:
A compound of Formula 1: or a pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein:X is â€”CH2NR7â€” or â€”NR7CHR6â€”, wherein the first dash of each of the foregoing X groups is attached to Y and the last dash of each of the foregoing X groups is attached to the C-8 carbon; Y is â€”CH(CH3)â€”; or X, Y, and R3 can be taken together to form the moiety of Formula a Z is selected from the group consisting of â€”C(O)â€”, â€”CH(â€”OR8)â€”, and the moiety of Formula b R1 is H or a hydroxy protecting group; R2 is â€”OR3, or R2 and R3 are taken together to form the moiety of Formula c or if X is â€”NR7CHR6â€”, R2 and R6 can be taken together to form the moiety of Formula d R3 is â€”OC(O)R14, or R3, X, and Y are taken together to form the moiety of Formula a, or R3 and R2 are taken together to form the moiety of Formula c; R4 is â€”OR15; R5 is an alpha-branched C2-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C2-C8 alkoxyalkyl, or C2-C8 alkylthioalkyl group optionally substituted with at least one hydroxyl group; an alpha-branched C2-C5 alkyl group attached to a C5-C8 cycloalkyl group; a C3-C8 cycloalkyl or cycloalkenyl group optionally substituted with at least one moiety selected from the group consisting of methyl, hydroxyl, halo, and C1-C4 alkyl groups; or a 3-6 membered saturated, or fully or partially unsaturated, heterocycle comprising at least one atom of oxygen or sulphur and optionally substituted with one or more C1-C4 alkyl groups or halogen atoms; R6 is H, or if X is â€”NR7CHR6â€”, R6 and R2 can be taken together to form the moiety of Formula d; R7 is 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 the alkyl, alkenyl, aryl, heteroaryl, and alkynyl moieties of the foregoing R7 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl; R8 is selected from the group consisting of H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, â€”C(O)R7, â€”C(O)NR17R18, â€”(CH2)m(C6-C10 aryl), and â€”(CH2)m(5-10 membered heteroaryl), wherein the alkyl, alkenyl, alkynyl, aryl, and heteroaryl moieties of the foregoing R8 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl; R9 is hydroxy; R10 is selected from the group consisting of H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, cyano, â€”CH2S(O)nR11, â€”CH2OR11, â€”CH2NR11R12,â€”(CH2)m(C6-C8 aryl), and â€”(CH2)m(5-10 membered heteroaryl), wherein the alkyl, alkenyl, alkynyl, aryl, and heteroaryl moieties of the foregoing R10 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R2, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl; each R11 and R12 is independently selected from the group consisting of H, C1-C6 alkyl, C2-C6 alkenyl, (CH2)m(C6-C10 aryl), (CH2)m(5-10 membered heteroaryl), and C2-C10 alkynyl, wherein the alkyl, alkenyl, aryl, heteroaryl, and alkynyl moieties of the foregoing R11 and R12 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, C1-C6 alkyl, and C1-C6 alkoxy; R13 is selected from the group consisting of H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, â€”R16(C6-C10 aryl), and â€”R16(5-10 membered heteroaryl), wherein the alkyl, alkenyl, alkynyl, aryl, and heteroaryl moieties of the foregoing R13 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl; R14 is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, â€”(CH2)m(C6-C10 aryl), and â€”(CH2)m(5-10 membered heteroaryl), wherein the alkyl, alkenyl, aryl, heteroaryl, and alkynyl moieties of the foregoing R14 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl; each R15 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 the alkyl, alkenyl, alkynyl, aryl, and heteroaryl moieties of the foregoing R15 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl; R16 is selected from the group consisting of C1-C6 alkyl, C3-C6 alkenyl, and C3-C6 alkynyl, wherein the alkyl, alkenyl, and alkynyl moieties of the foregoing R16 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”C(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, and 5-10 membered heteroaryl, and wherein at least one carbon atom of each of the foregoing R16 groups can optionally be replaced with 1 to 3 atoms or moieties independently selected from group consisting of O, N(R15), and S; each of R17 and R18 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 the alkyl, alkenyl, alkynyl, aryl, and heteroaryl moieties of the foregoing R17 and R18 groups are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halo, cyano, nitro, trifluoromethyl, azido, â€”(O)R11, â€”OC(O)R11, â€”NR11C(O)R12, â€”C(O)NR11R12, â€”NR11R12, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, 5-10 membered heteroaryl; each n independently represents an integer of from 0 to 2; and each m independently represents an integer of from 0 to 4.