| US 7,517,898 B2 | ||
| Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof | ||
| Ziping Liu, St. Laurent (Canada); Daniel Pagé, St. Laurent (Canada); Christopher Walpole, St. Laurent (Canada); and Hua Yang, St. Laurent (Canada) | ||
| Assigned to AstraZeneca AB, Sodertalje (Sweden) | ||
| Appl. No. 10/557,813 PCT Filed Jun. 09, 2004, PCT No. PCT/GB2004/002427 § 371(c)(1), (2), (4) Date Nov. 22, 2005, PCT Pub. No. WO2004/108688, PCT Pub. Date Dec. 16, 2004. |
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| Claims priority of application No. 0301699 (SE), filed on Jun. 10, 2003. | ||
| Prior Publication US 2007/0060583 A1, Mar. 15, 2007 | ||
| This patent is subject to a terminal disclaimer. | ||
| Int. Cl. A61K 31/4184 (2006.01); C07D 235/04 (2006.01) | ||
| U.S. Cl. 514—394 [548/300.1; 548/301.7; 548/302.7; 548/304.4; 548/309.7; 514/385] | 8 Claims |
1. A compound of formula I or a pharmaceutically acceptable salt thereof:
 Z is selected from O═ and S═;
R1 is selected from R5R6N—C1-6alkyl, R5O—C1-6alkyl, R5C(═O)N(—R6)—C1-6alkyl, R5R6NS(═O)2—C1-6alkyl, R5CS(═O)2N(—R6)—C1-6alkyl, R5R6NC(═O)N(—R7)—C1-6alkyl, R5R6NS(═O)2N(R7)—C1-6alkyl, C6-10aryl-C1-6alkyl, C6-10aryl-C(═O)—C1-6alkyl, C3-10cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocyclyl-C1-6alkyl, C3-6heterocyclyl-C(═O)—C1-6alkyl, C1-10hydrocarbylamino, R5R6N—, R5O—, R5C(═O)N(—R6)—, R5R6NS(═O)2—, R5CS(═O)2N(—R6)—, R5R6NC(═O)N(—R7)—, R5R6NS(═O)2N(R7)—, C6-10aryl-C6-10aryl-C(═O)—, C3-10cycloalkyl, C4-8cycloalkenyl, C3-6heterocyclyl and C3-6heterocyclyl-C(═O)—; wherein said C6-10aryl-C1-6alkyl, C6-10aryl-C(═O)—C1-6alkyl, C3-10cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocyclyl-C1-6alkyl, C3-6heterocyclyl-C(═O)—C1-6alkyl, C1-10hydrocarbylamino, C6-10aryl, C6-10aryl-C(═O)—, C3-10cycloalkyl, C4-8cycloalkenyl, C3-6heterocyclyl or C3-6heterocyclyl-C(═O)— used in defining R1 is optionally substituted by one or more groups selected from carboxy, halogen, cyano, nitro, methoxy, ethoxy, methyl, ethyl,
hydroxy and —NR5R6;
R2 is selected from the group consisting of C1-10alkyl, C2-10alkenyl, C2-10alkynyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocycloalkyl-C1-6alkyl, C4-8cycloalkenyl, R5R6N—, C3-5heteroaryl, C6-10aryl and C3-6heterocycloalkyl, wherein said C1-10alkyl, C2-10alkenyl, C2-10alkynyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-6alkyl, C4-8cycloalkenyl-C1-6alkyl, C3-6heterocycloalkyl-C1-6alkyl, C4-8cycloalkenyl, C3-5heteroaryl, C6-10aryl or C3-6heterocycloalkyl used in defining R2 is optionally substituted by one or more groups selected from halogen, cyano, nitro, methoxy, ethoxy, methyl, ethyl, hydroxy,
and —NR5R6;
wherein R5, R6 and R7 are independently selected from —H, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and a divalent C1-6group that together with another divalent R5, R6 or R7 forms a portion of a ring; and
R3 and R4 are independently selected from —OH, R8 and —O—R8, wherein R8 is independently selected from C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and a divalent C1-6group that together with another divalent R8 forms a portion of a ring, wherein R3 and R4 are not —H at the same time, and wherein said C1-6alkyl, C2-6alkenyl, C2-6alkynyl, or divalent C1-6group in defining R8 is optionally substituted by one or more groups selected from carboxy, halogen, cyano, nitro, methoxy, ethoxy, hydroxy, carboxy
and —NR5R6; or R3 and R4 together with the nitrogen connected thereto form a portion of a 5- or 6-membered ring, wherein said ring is optionally substituted
by one or more groups selected from carboxy, halogen, cyano, nitro, methoxy, ethoxy, hydroxy, carboxy and —NR5R6.
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