Antiviral compounds

• US 8,822,430 B2
• Filed: 07/31/2013
• Issued: 09/02/2014
• Est. Priority Date: 05/13/2009
• Status: Active Grant

• Current Assignee: Gilead Sciences Inc.
• Original Assignee: Gilead Pharmasset LLC (Gilead Sciences Inc.)
• Inventors: Bacon, Elizabeth M., Canales, Eda, Cho, Aesop, Cottell, Jeromy J., Desai, Manoj C., Graupe, Michael, Guo, Hongyan, Halcomb, Randall L., Kato, Darryl, Kim, Choung U., Kirschberg, Thorsten A., Krygowski, Evan S., Lazerwith, Scott E., Link, John O., Liu, Hongtao, Liu, Qi, Mackman, Richard L., Parrish, Jay P., Pyun, Hyung-Jung, Saugier, Joseph H., Schroeder, Scott D., Sun, Jianyu, Taylor, James G., Trenkle, James D., Tse, Winston C., Vivian, Randall W., Watkins, William J., Xu, Lianhong, Mitchell, Michael L.
• Primary Examiner(s): Yoo, Sun Jae
• Application Number:
  US13/956,195
• Publication Number:
  US 20140051656A1
• Time in Patent Office: 398 Days
• Field of Search: None
• US Class Current: 514/49
• CPC Class Codes: A61K 31/4025 not condensed and containing further heterocyclic rings, e.g. cromakalim
• CPC Class Codes: A61K 31/4178 not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
• CPC Class Codes: A61K 31/4184 condensed with carbocyclic rings, e.g. benzimidazoles
• CPC Class Codes: A61K 31/427 not condensed and containing further heterocyclic rings
• CPC Class Codes: A61K 31/435 having six-membered rings with one nitrogen as the only ring hetero atom
• CPC Class Codes: A61K 31/437 the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
• CPC Class Codes: A61K 31/4439 containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole nicotine A61K31/465
• CPC Class Codes: A61K 31/454 containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
• CPC Class Codes: A61K 31/496 Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
• CPC Class Codes: A61K 31/519 ortho- or peri-condensed with heterocyclic rings
• CPC Class Codes: A61K 31/5377 not condensed and containing further heterocyclic rings, e.g. timolol
• CPC Class Codes: A61K 31/5415 ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
• CPC Class Codes: A61K 31/55 having seven-membered rings, e.g. azelastine, pentylenetetrazole
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: C07D 207/16 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 : containing three or more hetero rings
• CPC Class Codes: C07D 413/14 : containing three or more hetero rings
• CPC Class Codes: C07D 417/14 : containing three or more hetero rings
• CPC Class Codes: C07D 471/04 : Ortho-condensed systems
• CPC Class Codes: C07D 471/08 : Bridged systems
• CPC Class Codes: C07D 471/10 : Spiro-condensed systems
• CPC Class Codes: C07D 487/04 : Ortho-condensed systems
• CPC Class Codes: C07D 491/113 : with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
• CPC Class Codes: C07D 495/04 : Ortho-condensed systems
• CPC Class Codes: C07F 5/025 : Boronic and borinic acid compounds

Abstract

The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

Claims

1. A compound of formula:

2. The compound of claim 1 that is:

3. The compound of claim 1 that is:

4. The compound of claim 1 wherein P is selected from:

5. The compound of claim 1 wherein P is

6. The compound of claim 1 wherein P is

7. The compound of claim 1 that is:

8. The compound of claim 1 that is:

11. The compound of claim 1 wherein each V is:

14. A pharmaceutical composition comprising the compound as described in claim 1 and at least one pharmaceutically acceptable carrier.

16. A method of inhibiting HCV in a human comprising administering a compound of claim 1.

9. A compound:

10. A compound:

12. A compound of formula:

13. A compound of formula:

15. A pharmaceutical composition comprising a compound of formula:

17. A method of inhibiting HCV in a human comprising administering a compound of formula: