| US 7,468,375 B2 | ||
| Inhibitors of the HIV integrase enzyme | ||
| Klaus Ruprecht Dress, San Diego, Calif. (US); Qiyue Hu, Carlsbad, Calif. (US); Ted William Johnson, San Diego, Calif. (US); Michael Bruno Plewe, San Diego, Calif. (US); Steven Paul Tanis, Carlsbad, Calif. (US); Hai Wang, San Diego, Calif. (US); Anle Yang, San Diego, Calif. (US); Chunfeng Yin, San Diego, Calif. (US); and Junhu Zhang, San Diego, Calif. (US) | ||
| Assigned to Pfizer Inc., New York, N.Y. (US) | ||
| Filed on Apr. 25, 2005, as Appl. No. 11/115,003. | ||
| Claims priority of provisional application 60/565705, filed on Apr. 26, 2004. | ||
| Claims priority of provisional application 60/660502, filed on Mar. 09, 2005. | ||
| Prior Publication US 2005/0277662 A1, Dec. 15, 2005 | ||
| Int. Cl. C07D 471/02 (2006.01); A61K 31/4745 (2006.01) | ||
| U.S. Cl. 514—300 [546/113] | 20 Claims |
1. A compound of formula (I),
 R1 is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C1-C8 heteroalkyl, wherein said C1-C8 alkyl, C2-C8 alkenyl, or C1-C8 heteroalkyl groups may be optionally substituted with at least one substituent independently selected from:
halo, —OR12a, —N(R12aR12b), —C(O)N(R12a)2, —NR12aC(O)N(R12aR12b), —NR12aC(O)R12a, —NR12aC(NR12a)N(R12aR12b), —SR12a, —S(O)R12a, —S(O)2R12a, —S(O)2N(R12aR12b)2, C1-C8 alkyl, C6-C14 aryl, C3-C8 cycloalkyl, and C2-C9 heteroaryl, wherein said C1-C8 alkyl, C6-C14 aryl, C3-C8 cycloalkyl, and C2-C9 heteroaryl groups are optionally substituted with at least one substituent independently selected from halo, —C(R12aR12bR12c), —OH, and C1-C8 alkoxy;
R2 is hydrogen;
R3 is —(CR8R9)tNR10R11 or C1-C8 heteroalkyl, wherein said C1-C8 heteroalkyl is substituted with R24;
R4 is hydrogen, halo, C1-C8 alkyl, —OR12a, —NR12R12b, C1-C8 heteroalkyl, C2-C8 alkenyl, or C2-C8 alkynyl, wherein said C2-C8 alkenyl or C2-C8 alkynyl are optionally substituted with at least one R26;
R5 is hydrogen;
R6 is hydrogen, C1-C8 alkyl, C1-C8 heteroalkyl, or C2-C8 alkenyl, wherein said C2-C8 alkenyl is optionally substituted with at least one —OR12a group;
R7 is hydrogen, C1-C8 heteroalkyl, C6-C14 aryl, C2-C8 alkenyl, or C1-C8 alkyl,
wherein said C1-C8 alkyl is optionally substituted with at least one C3-C8 cycloalkyl or C6-C14 aryl group;
each R8 and R9, which may be the same or different, are independently selected from hydrogen and C1-C8 alkyl;
R10 and R11, together with the nitrogen atom to which they are attached, form a C2-C9 cycloheteroalkyl group optionally substituted with at least one C1-C8 alkyl;
each R12a, R12b, and R12c, which may be the same or different, is independently selected from hydrogen and C1-C8 alkyl;
R24 is C3-C8 cycloalkyl, C2-C9 cycloheteroalkyl, or C2-C9 heteroaryl, each of which is optionally substituted with at least one substituent independently selected from C1-C8 alkyl, C6-C14 aryl, C2-C9 heteroaryl, —CF3, and —OR12a;
each R26 is independently selected from —OR12a, halo, C6-C14 aryl, C2-C9 heteroaryl, C1-C8 heteroalkyl, C3-C8 cycloalkyl, C2-C9 cycloheteroalkyl, and —C(R12aR12bR12c); and
t is an integer from 1 to 3; or
a pharmaceutically acceptable salt or solvate thereof.
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