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US 2009/0156822 A1Published application
Hepatitis C Inhibitor Dipeptide Analogs
AssigneeBoehringer Ingelheim International GmbH
InventorsMurray D. BAILEY, Punit BHARDWAJ, Elise GHIRO, Nathalie GOUDREAU, Teddy HALMOS, Montse LLINAS-BRUNET, Marc-Andre POUPART, Jean RANCOURT
Life of this patent
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Abstract
Compounds of formula (I): wherein R1, R2, R3, R4, n and m are as defined herein. The compounds are useful as inhibitors of HCV NS3 protease.
Claims19
An azalactone intermediate compound of formula (III):
- wherein n is 1 or 2;
- R1 is (C1-6)alkyl (C2-6)alkenyl, or (C2-6)alkynyl;
- wherein the (C1-6)alkyl, (C2-6)alkenyl, and (C2-6)alkynyl are optionally substituted at one or more substitutable positions with from one to three halogen atoms;
- R2 is selected from —NH—R20, —O—R20, —S—R20, —SO—R20, —SO2—R20, —OCH2—R20, and —CH2O—R20, wherein
- R20 is aryl or Het, wherein the aryl and Het are optionally substituted with R200, wherein
- R200 is one to four substituents each independently selected from H, halogen, cyano, (C1-6)alkyl, (C3-7)cycloalkyl, aryl-(C1-6)alkyl-, aryl, Het, oxo, thioxo, —OR201, —SR201, —SOR201, —SO2R201, —N(R202)R201, and —CON(R202)R201;
- wherein each of the alkyl, cycloalkyl, aryl and Het is optionally further substituted with R2000;
- R201 in each case is independently selected from H, (C1-6)alkyl, aryl, (C2-4)alkenyl, (C2-4)alkynyl, —CO—(C1-6)alkyl and —CO—O—(C1-6)alkyl, wherein each of the alkyl and aryl is optionally further substituted with R2000;
- R202 is H or (C1-6)alkyl;
- R2000 is one to three substituents each independently selected from halogen, R2003, aryl, Het, —OR2001, —SR2001, —SOR2001, —SO2R2001, cyano and —N(R2002)(R2001), wherein the aryl and Het are each optionally substituted with one, two or three substituents each independently selected from (C1-6)alkyl and —O—(C1-6)alkyl;
- R2001 in each case is independently selected from aryl, aryl-(C1-6)alkyl-, —C(O)—R2003, —C(O)O—R2003, —CON(R2002)(R2004) and R2004;
- R2002 in each case is independently selected from H and (C1-6)alkyl;
- R2003 in each case is independently selected from (C1-8)alkyl, (C3-7)cycloalkyl and (C3-7)cycloalkyl-(C1-4)alkyl-, wherein the (C3-7)cycloalkyl and (C3-7)cycloalkyl-(C1-4)alkyl- are each optionally substituted with one to three substituents each independently selected from (C1-3)alkyl;
- and
- R2004 in each case is independently selected from H and R2003;
- R3 is selected from:
- (i) —C(O)OR31 wherein R31 is (C1-6)alkyl or aryl, wherein the (C1-6)alkyl is optionally substituted with one to three halogen substituents;
- (ii) —C(O)NR32R33, wherein R32 and R33 are each independently selected from H, (C1-6)alkyl, and Het;
- (iii) —SOvR34 wherein v is 1 or 2 and R34 is selected from:
- (C1-6)alkyl, aryl, Het, and NR32R33 wherein R32 and R33 are as defined above;
- and
- (iv) —C(O)—R35, wherein R35 is selected from (C1-8)alkyl, (C3-7)cycloalkyl, (C3-7)cycloalkyl-(C1-4)alkyl-, aryl, aryl-(C1-6)alkyl-, Het and Het-(C1-6)alkyl, each of which are optionally substituted with one or more substituents each independently selected from halo, (C1-6)alkyl, (C3-7)cycloalkyl, aryl, Het, hydroxyl, —O—(C1-6)alkyl, —S—(C1-6)alkyl, —SO—(C1-6)alkyl, —SO2—(C1-6)alkyl, —O-aryl, —S-aryl, —SO-aryl and —SO2-aryl, wherein the aryl portion of the —O-aryl, —S-aryl, —SO-aryl and —SO2-aryl are each optionally substituted with one to five halo substituents.
19 more elements
Dependencies are inferred from the claim text.