IP Library Granted Patent US 8,329,703
Granted Patent B2
US 8,329,703 · App. 11/058,852 · Granted Dec 11, 2012

Pyrazole compounds

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,329,703
App. No.
11/058,852
Granted
Dec 11, 2012
Kind
B2
Abstract

Aryl substituted pyrazole derivatives are provided, as well as processes for their preparation. The invention also provides compositions and methods for the treatment of HCV by administering a compound of the present invention, alone or in combination with additional antiviral agents, in a therapeutically effective amount.

Claims (36)

1. The compound having the formula V:

wherein:

each R 1 is independently selected from alkyl, alkenyl, alkynyl, aralkyl, —O—R 11 , —N(R 12 )(R 13 ), —N(R 11 )C(O)R 11 , —N(R 11 )SO 2 R 11 , —SR 11 , —C(O)R 11 , —C(O)OR 11 , —C(O)N(R 12 )(R 13 ), —OC(O)R 11 , —OC(O)N(R 12 )(R 13 ), CN, CF 3 , NO 2 , SO 2 , —SOR 11 , —SO 3 R 11 , —SO 2 N(R 12 )(R 13 ), -alkyl-O—R 11 , cycloalkyl, cycloalkenyl, halo, aryl or heteroaryl;

additionally or alternatively two R 1 substituents on adjacent ring atoms may be combined to form a fused 5 or 6-membered ring, wherein the fused 5- or 6-membered ring may contain from 0 to 3 ring heteroatoms;

each R 11 is independently selected from H, alkyl, alkyl-O-alkyl, alkyl-O-aryl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, aryl or heteroaryl;

each R 12 and R 13 is independently selected from H, alkyl, cycloalkyl, cycloalkenyl, alkyl-O-alkyl, alkyl-O-aryl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl; or R 12 and R 13 may be taken together with the nitrogen to which they are attached to form a 5- to 7-membered ring which may optionally contain a further heteroatom;

n is 0 to 4;

R 3 is H;

R 45 is selected from the group consisting of H, alkyl, -alkyl-O-alkyl, -alkyl-O-aryl, aryl, aralkyl, cycloalkyl, cycloalkenyl, and —(CH 2 ) a —R 42 ;

R 42 is selected from the group consisting of —N(R 421 )C(O)R 421 , —N(R 421 )SO 2 R 421 , —OR 421 , —SR 421 , —C(O)R 421 , —C(O)OR 421 —C(O)N(R 422 )(R 423 ), —OC(O)R 421 , —OC(O)N(R 422 )(R 423 ), CN, CF 3 , NO 2 , SO 2 , —SOR 421 , —SO 3 R 421 , —SO 2 N(R 422 )(R 423 ), -alkyl-O-alkyl, -alkyl-O-aryl, halo, cycloalkyl, cycloalkenyl, aryl and heteroaryl; or

R 42 is

each R 421 is independently selected from H, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl;

each R 422 and R 423 is independently selected from H, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl; or R 422 and R 423 may be taken together with the nitrogen to which they are attached to form a 5- to 7-membered ring which may optionally contain a further heteroatom;

each R 424 is independently selected from H, OH, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl;

each R 425 and R 426 is independently selected from H, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl or heteroaryl; or R 425 and R 426 may be taken together with the carbon to which they are attached to form a 5- to 7-membered ring which may optionally contain a further heteroatom;

a is 1 to 6;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 having the formula

3. The compound of claim 1 having the formula

4. The compound of claim 1 having the formula

5. The compound of claim 1 having the formula

6. The compound of claim 1 having the formula

7. The compound of claim 1 having the formula

8. The compound of claim 1 having the formula

9. The compound of claim 1 having the formula

10. The compound of claim 1 having the formula

11. The compound of claim 1 having the formula

12. The compound of claim 1 having the formula

13. The compound of claim 1 having the formula

14. The compound of claim 1 having the formula

15. The compound of claim 1 having the formula

16. A pharmaceutical composition for the treatment of HCV infection, comprising a therapeutically effective amount of a compound of according to claim 1 in a pharmaceutically acceptable carrier.

17. The pharmaceutical composition of claim 16 , further comprising a second antiviral agent.

18. The pharmaceutical composition of claim 17 , wherein the second anti-viral agent is selected from the group consisting of an interferon, ribavirin, an HCV protease inhibitor, an HCV polymerase inhibitor, an HCV IRES inhibitor, an HCV Helicase, and an HCV ATPase inhibitor.

19. The pharmaceutical composition of claim 18 , wherein the second agent is an interferon.

20. The pharmaceutical composition of claim 19 , wherein the second agent is α-interferon.