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Details for Patent: 9,394,279

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Details for Patent: 9,394,279

Title:Anti-viral compounds
Abstract: Compounds effective in inhibiting replication of Hepatitis C virus ("HCV") are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.
Inventor(s): Krueger; Allan C. (Gurnee, IL), Kati; Warren M. (Gurnee, IL), Carroll; William A. (Evanston, IL), Pratt; John K. (Kenosha, WI), Hutchinson; Douglas K. (Antioch, IL)
Assignee: AbbVie Inc. (North Chicago, IL)
Filing Date:Dec 16, 2011
Application Number:13/328,848
Claims:1. A compound of Formula I, or a pharmaceutically acceptable salt thereof, ##STR01035## wherein: X is cyclopropyl, and is optionally substituted with one or more R.sub.A; L.sub.1, L.sub.2 and L.sub.3 are each a bond; A is selected from ##STR01036## or ##STR01037## B is selected from ##STR01038## or ##STR01039## Z.sub.1 is independently selected at each occurrence from O, S, NH or CH.sub.2, Z.sub.2 is independently selected at each occurrence from N or CH, and W.sub.1, W.sub.2, W.sub.3, W.sub.4, W.sub.5 and W.sub.6 are each independently selected at each occurrence from CH or N, wherein A and B are each independently optionally substituted with one or more R.sub.A; D is C.sub.3-C.sub.12carbocycle or 3- to 12-membered heterocycle, and is optionally substituted with one or more R.sub.A; or D is C.sub.3-C.sub.12carbocycle or 3- to 12-membered heterocycle, and is substituted with J and optionally substituted with one or more R.sub.A, wherein J is C.sub.3-C.sub.12carbocycle or 3- to 12-membered heterocycle and is optionally substituted with one or more R.sub.A; Y is --C(R.sub.1R.sub.2)N(R.sub.5)-T-R.sub.D, or --C(R.sub.3R.sub.4)C(R.sub.6R.sub.7)-T-R.sub.D; Z is --C(R.sub.8R.sub.9)N(R.sub.12)-T-R.sub.D, or --C(R.sub.10R.sub.11)C(R.sub.13R.sub.14)-T-R.sub.D; R.sub.1 is R.sub.C, and R.sub.2 and R.sub.5, taken together with the atoms to which they are attached, form a 3- to 12-membered heterocycle which is optionally substituted with one or more R.sub.A; R.sub.3 and R.sub.6 are each independently R.sub.C, and R.sub.4 and R.sub.7, taken together with the atoms to which they are attached, form a 3- to 12-membered carbocycle or heterocycle which is optionally substituted with one or more R.sub.A; R.sub.8 is R.sub.C, and R.sub.9 and R.sub.12, taken together with the atoms to which they are attached, form a 3- to 12-membered heterocycle which is optionally substituted with one or more R.sub.A; R.sub.10 and R.sub.13 are each independently R.sub.c, and R.sub.11 and R.sub.14, taken together with the atoms to which they are attached, form a 3- to 12-membered carbocycle or heterocycle which is optionally substituted with one or more R.sub.A; T is each independently selected at each occurrence from bond, -L.sub.S-, -L.sub.S-M-L.sub.S'-, or -L.sub.S-M-L.sub.S'-M'-L.sub.S''-, wherein M and M' are each independently selected at each occurrence from bond, --O--, --S--, --N(R.sub.B)--, --C(O)--, --S(O).sub.2--, --S(O)--, --OS(O)--, --OS(O).sub.2--, --S(O).sub.2O--, --S(O)O--, --C(O)O--, --OC(O)--, --OC(O)O--, --C(O)N(R.sub.B)--, --N(R.sub.B)C(O)--, --N(R.sub.B)C(O)O--, --OC(O)N(R.sub.B)--, --N(R.sub.B)S(O)--, --N(R.sub.B)S(O).sub.2--, --S(O)N(R.sub.B)--, --S(O).sub.2N(R.sub.B)--, --C(O)N(R.sub.B)C(O)--, --N(R.sub.B)C(O)N(R.sub.B')--, --N(R.sub.B)SO.sub.2N(R.sub.B')--, --N(R.sub.B)S(O)N(R.sub.B')--, C.sub.3-C.sub.12carbocycle or 3- to 12-membered heterocycle, and wherein said C.sub.3-C.sub.12carbocycle and 3- to 12-membered heterocycle are each independently optionally substituted at each occurrence with one or more R.sub.A; R.sub.D is each independently selected at each occurrence from hydrogen or R.sub.A; R.sub.A is independently selected at each occurrence from halogen, nitro, oxo, phosphonoxy, phosphono, thioxo, cyano, or -L.sub.S-R.sub.E; R.sub.B and R.sub.B' are each independently selected at each occurrence from hydrogen; or C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl or C.sub.2-C.sub.6alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano or 3- to 6-membered carbocycle or heterocycle; or 3- to 6-membered carbocycle or heterocycle; wherein each 3- to 6-membered carbocycle or heterocycle in R.sub.B or R.sub.B' is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6haloalkynyl; R.sub.C is independently selected at each occurrence from hydrogen, halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl or cyano; or C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl or C.sub.2-C.sub.6alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano or 3- to 6-membered carbocycle or heterocycle; or 3- to 6-membered carbocycle or heterocycle; wherein each 3- to 6-membered carbocycle or heterocycle in R.sub.C is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6haloalkynyl; R.sub.E is independently selected at each occurrence from --O--R.sub.S, --S--R.sub.S, --C(O)R.sub.S, --OC(O)R.sub.S, --C(O)OR.sub.S, --N(R.sub.SR.sub.S'), --S(O)R.sub.S, --SO.sub.2R.sub.S, --C(O)N(R.sub.SR.sub.S'), --N(R.sub.S)C(O)R.sub.S', --N(R.sub.S)C(O)N(R.sub.S'R.sub.S''), --N(R.sub.S)SO.sub.2R.sub.S', --SO.sub.2N(R.sub.SR.sub.S'), --N(R.sub.S)SO.sub.2N(R.sub.S'R.sub.S''), --N(R.sub.S)S(O)N(R.sub.S'R.sub.S''), --OS(O)--R.sub.S, --OS(O).sub.2--R.sub.S, --S(O).sub.2OR.sub.S, --S(O)OR.sub.S, --OC(O)OR.sub.S, --N(R.sub.S)C(O)OR.sub.S', --OC(O)N(R.sub.SR.sub.S'), --N(R.sub.S)S(O)--R.sub.S', --S(O)N(R.sub.SR.sub.S'), P(O)(OR.sub.S).sub.2 or --C(O)N(R.sub.S)C(O)--R.sub.S'; or C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl or C.sub.2-C.sub.6alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl or cyano; or C.sub.3-C.sub.6carbocycle or 3- to 6-membered heterocycle, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6haloalkynyl, C(O)OR.sub.S or --N(R.sub.SR.sub.S'); R.sub.L is independently selected at each occurrence from halogen, nitro, oxo, phosphonoxy, phosphono, thioxo, cyano, --O--R.sub.S, --S--R.sub.S, --C(O)R.sub.S, --OC(O)R.sub.S, --C(O)OR.sub.S, --N(R.sub.SR.sub.S'), --S(O)R.sub.S, --SO.sub.2R.sub.S, --C(O)N(R.sub.SR.sub.S') or --N(R.sub.S)C(O)R.sub.S'; or C.sub.3-C.sub.6carbocycle 3- to 6-membered heterocycle, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6haloalkynyl; L.sub.S, L.sub.S' and L.sub.S'' are each independently selected at each occurrence from bond; or C.sub.1-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene or C.sub.2-C.sub.6alkynylene, each of which is independently optionally substituted at each occurrence with one or more R.sub.L; and R.sub.S, R.sub.S' and R.sub.S'' are each independently selected at each occurrence from hydrogen; or C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl or C.sub.2-C.sub.6alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano or 3- to 6-membered carbocycle or heterocycle; or --(R.sub.G--R.sub.H).sub.n--(R.sub.G--R.sub.H'), wherein each n is independently 0, 1, 2, 3 or 4; each R.sub.G is independently O, S or N(R.sub.B); each R.sub.H is independently C.sub.1-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene or C.sub.2-C.sub.6alkynylene, each of which is optionally substituted with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano or 3- to 6-membered carbocycle or heterocycle; and each R.sub.H' is independently C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl or C.sub.2-C.sub.6alkynyl, each of which is optionally substituted with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano or 3- to 6-membered carbocycle or heterocycle; or 3- to 6-membered carbocycle or heterocycle; wherein each 3- to 6-membered carbocycle or heterocycle in R.sub.S, R.sub.S' or R.sub.S'' is independently optionally substituted at each occurrence with one or more substituents selected from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, formyl, cyano, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6haloalkenyl or C.sub.2-C.sub.6haloalkynyl.

2. The compound or salt of claim 1, wherein: T is independently selected at each occurrence from --C(O)-L.sub.S'-M'-L.sub.S''- or --N(R.sub.B)C(O)-L.sub.S'-M'-L.sub.S''-; and L.sub.S' is each independently C.sub.1-C.sub.6alkylene, and is independently optionally substituted at each occurrence with one or more R.sub.L.

3. The compound or salt of claim 1, wherein: Y is --C(R.sub.1R.sub.2)N(R.sub.5)-T-R.sub.D; Z is --C(R.sub.8R.sub.9)N(R.sub.12)-T-R.sub.D; T is independently selected at each occurrence from --C(O)-L.sub.S'-M'-L.sub.S''-; and D is C.sub.5-C.sub.6carbocycle, 5- to 6-membered heterocycle, or 6- to 10-membered bicycles, and is substituted with one or more R.sub.A; or D is C.sub.5-C.sub.6carbocycle or 5- to 6-membered heterocycle, and is substituted with J and optionally substituted with one or more R.sub.A, wherein J is C.sub.3-C.sub.6carbocycle or 3- to 6-membered heterocycle and is optionally substituted with one or more R.sub.A.

4. The compound or salt of claim 3, wherein T is independently selected at each occurrence from --C(O)-L.sub.S'-N(R.sub.B)C(O)-L.sub.S''- or --C(O)-L.sub.S'-N(R.sub.B)C(O)O-L.sub.S''-; and R.sub.2 and R.sub.5, taken together with the atoms to which they are attached, form ##STR01040## which is optionally substituted with one or more R.sub.A; and R.sub.9 and R.sub.12, taken together with the atoms to which they are attached, form ##STR01041## which is optionally substituted with one or more R.sub.A.

5. The compound of claim 4, wherein A is ##STR01042## B is ##STR01043## and A and B are each independently optionally substituted with one or more R.sub.A.

6. The compound of claim 1, wherein the compound is selected from the group consisting of: dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(3-(4-methoxyphenyl)cyclopropane-1,2-d- iyl)bis(4,1-phenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidine-2,1-- diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate; dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(3-(4-(benzyloxy)phenyl)cyclopropane-1- ,2-diyl)bis(4,1-phenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidine-- 2,1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate; dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(4,4'-(3-(4-methoxyphenyl)cyclopropane- -1,2-diyl)bis(4,1-phenylene))bis(1H-imidazole-4,2-diyl))bis(pyrrolidine-2,- 1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate; dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(4,4'-(3-(4-(benzyloxy)phenyl)cyclopro- pane-1,2-diyl)bis(4,1-phenylene))bis(1H-imidazole-4,2-diyl))bis(pyrrolidin- e-2,1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate; dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(5,5'-(3-(4-(benzyloxy)phenyl)cyclopropane-1- ,2-diyl)bis(1H-benzo[d]imidazole-5,2-diyl))bis(pyrrolidine-2,1-diyl))bis(3- -methyl-1-oxobutane-2,1-diyl)dicarbamate; dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(3-(4-cyclohexylphenyl)cyclopropane-1,- 2-diyl)bis(4,1-phenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidine-2- ,1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate; dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(2-(4-tert-butylphenyl)cyclopent-3-ene- -1,3-diyl)bis(4,1-phenylene)bis(azanediyl)bis(oxomethylene))bis(pyrrolidin- e-2,1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate; and dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-(2-(4-tert-butylphenyl)cyclopentane-1,- 3-diyl)bis(4,1-phenylene)bis(azanediyl)bis(oxomethylene))bis(pyrrolidine-2- ,1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate.

7. A pharmaceutical composition comprising a compound or salt according to claim 1 and another anti-HCV agent.
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