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Details for Patent: 8,716,454

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Details for Patent: 8,716,454

Title:Solid compositions
Abstract: The present invention features solid compositions comprising Compound I.sub.A, I.sub.B or I.sub.C, or a pharmaceutically acceptable salt thereof, in an amorphous form. In one embodiment, Compound I.sub.A, I.sub.B or I.sub.C, or a pharmaceutically acceptable salt thereof, is formulated in an amorphous solid dispersion which comprises a pharmaceutically acceptable hydrophilic polymer and preferably a pharmaceutically acceptable surfactant.
Inventor(s): Kullmann; Simon (Neustadt an der Weinstrasse, DE), Westedt; Ulrich (Schriesheim, DE), Pauli; Mirko (Ludwigshafen, DE), Schroeder; Rudolf (Worms-Pfeddersheim, DE), Woehrle; Gerd (Eppelheim, DE), Heitermann; Tanja (Wiesloch, DE), Koenig; Renato (Hassloch, DE), Thiel; Madlen (Schifferstadt, DE), Gao; Yi (Vernon Hills, IL), Wu; Jianwei (Libertyville, IL), Erickson; Bryan K. (Pleasant Prairie, WI)
Assignee: Abbvie Inc. (North Chicago, IL)
Filing Date:Jun 09, 2011
Application Number:13/156,793
Claims:1. A solid composition comprising (1) a compound, or a pharmaceutically acceptable salt thereof, in an amorphous form, (2) a pharmaceutically acceptable hydrophilic polymer; and (3) optionally a pharmaceutically acceptable surfactant, wherein said compound is selected from the group consisting of: methyl[(2S)-1-{(2S)-2-[4-(4-{5-(4-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)am- ino]-3-methylbutanoyl}pyrrolidin-2-yl]-1H-imidazol-4-yl}phenyl)-1-[6-(pipe- ridin-1-yl)pyridin-3-yl]-1H-pyrrol-2-yl}phenyl)-1H-imidazol-2-yl]pyrrolidi- n-1-yl}-3-methyl-1-oxobutan-2-yl]carbamate (Compound I.sub.A), methyl{(2S,3R)-1-[(2S)-2-{6-[(2R,5R)-1-(4-tert-butylphenyl)-5-(2-{(2S)-1-- [N-(methoxycarbonyl)-O-methyl-L-threonyl]pyrrolidin-2-yl}-1H-benzimidazol-- 6-yl)pyrrolidin-2-yl]-1H-benzimidazol-2-yl}pyrrolidin-1-yl]-3-methoxy-1-ox- obutan-2-yl}carbamate (Compound I.sub.B), and methyl{(2S)-1-[(2S)-2-{5-[(2R,5R)-1-[2,5-difluoro-4-(trifluoromethyl)phen- yl]-5-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}pyrroli- din-2-yl]-1H-benzimidazol-5-yl}pyrrolidin-2-yl]-1H-benzimidazol-2-yl}pyrro- lidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (Compound I.sub.C).

2. The composition of claim 1, comprising a solid dispersion which includes: (1) said compound or salt thereof, and (2) said polymer.

3. The composition of claim 2, wherein said polymer has a T.sub.g of at least 50.degree. C.

4. The composition of claim 3, further comprising said surfactant.

5. The composition of claim 4, wherein said solid dispersion comprises said surfactant.

6. The composition of claim 4, wherein said polymer is a homopolymer or copolymer of N-vinyl pyrrolidone.

7. The composition of claim 4, wherein said polymer is copovidone.

8. The composition of claim 7, wherein said surfactant is D-alpha-tocopheryl polyethylene glycol 1000 succinate.

9. The composition of claim 7, wherein said surfactant is a combination of D-alpha-tocopheryl polyethylene glycol 1000 succinate and propylene glycol monolaurate.

10. The composition of claim 7, wherein said surfactant is sorbitan mono laurate.

11. The composition of claim 4, wherein said solid dispersion is an amorphous solid dispersion.

12. The composition of claim 4, where said solid dispersion is a solid solution which comprises said surfactant.

13. The composition of claim 1, further comprising another anti-hepatitis C virus (HCV) agent.

14. The composition of claim 1, further comprising an HCV protease inhibitor.

15. The composition of claim 1, further comprising an HCV polymerase inhibitor.

16. The composition of claim 4, wherein said compound is Compound I.sub.A.

17. The composition of claim 4, wherein said compound is Compound I.sub.B.

18. The composition of claim 4, wherein said compound is Compound I.sub.C.

19. A process of making the composition of claim 1, comprising dissolving said compound or salt in a solvent.

20. The process of claim 19, wherein said solvent is said polymer.

21. A method of treating HCV comprising administering the composition of claim 1 to a patient in need thereof.

22. The method of claim 21, comprising administering another anti-HCV agent to said patient.
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