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Claims for Patent: 9,006,387

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Claims for Patent: 9,006,387

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): Wagner; Rolf (Antioch, IL), Pratt; John K. (Kenosha, IL), Liu; Dachun (Waukegan, IL), Tufano; Michael D. (Chicago, IL), DeGoey; David A. (Salem, WI), Kati; Warren M. (Gumee, IL), Hutchins; Charles W. (Green Oaks, IL), Donner; Pamela L. (Mundelein, IL), Randolph; John T. (Libertyville, IL), Motter; Christopher E. (Oak Creek, IL), Nelson; Lissa T. (Highland Park, IL), Patel; Sachin V. (Round Lake, IL), Matulenko; Mark A. (Libertyville, IL), Keddy; Ryan G. (Beach Park, IL), Jinkerson; Tammie K. (Pleasant Prairie, WI), Rockway; Todd W. (Grayslake, IL), Maring; Clarence J. (Palatine, IL), Hutchinson; Douglas K. (Antioch, IL), Flentge; Charles A. (Salem, WI), Betebenner; David A. (Libertyville, IL), Sarris; Kathy (Mundelein, IL), Woller; Kevin R. (Antioch, IL), Wagaw; Seble H. (Evanston, IL), Califano; Jean C. (Whitefish Bay, WI), Li; Wenke (Gumee, IL), Caspi; Daniel D. (Evanston, IL), Bellizzi; Mary E. (North Chicago, IL), Gao; Yi (Vernon Hills, IL), Krueger; Allan C. (Gumee, IL)
Assignee: AbbVie Inc. (North Chicago, IL)
Application Number:14/180,886
Patent Claims: 1. A method of treating HCV infection, comprising administering to an HCV patient a compound of Formula I or a pharmaceutically acceptable salt thereof, ##STR00900## wherein: X is ##STR00901## wherein the nitrogen ring atom is directly linked to -L.sub.3-D, and wherein X is optionally substituted with one or more R.sub.A; L.sub.1, L.sub.2 and L.sub.3 are bond; A and B are each independently ##STR00902## and 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; Y is --N(R.sub.B)C(O)C(R.sub.1R.sub.2)N(R.sub.5)-T-R.sub.D or --N(R.sub.B)C(O)C(R.sub.3R.sub.4)C(R.sub.6R.sub.7)-T-R.sub.D; Z is --N(R.sub.B)C(O)C(R.sub.8R.sub.9)N(R.sub.12)-T-R.sub.D or --N(R.sub.B)C(O)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') 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 or C.sub.2-C.sub.6haloalkynyl; 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; 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.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 method 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 method of claim 1, wherein: Y is --N(R.sub.B)C(O)C(R.sub.1R.sub.2)N(R.sub.5)-T-R.sub.D; Z is --N(R.sub.B)C(O)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.

4. The method 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 ##STR00903## 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 ##STR00904## which is optionally substituted with one or more R.sub.A.

5. The method of claim 1, wherein R.sub.A is independently selected at each occurrence from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, 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 or cyano.

6. The method of claim 5, wherein 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.

7. The method of claim 4, wherein R.sub.A is independently selected at each occurrence from halogen, hydroxy, mercapto, amino, carboxy, nitro, oxo, phosphonoxy, phosphono, thioxo, 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 or cyano.

8. The method of claim 7, wherein 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.

9. A method of claim 1, wherein said compound is dimethyl (2S,2'S)-1,1'-((2S,2'S)-2,2'-(4,4'-((2S,5S)-1-(4-tert-butylphenyl)pyrroli- dine-2,5-diyl)bis(4,1-phenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrol- idine-2,1-diyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate.
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