Anti-viral 7-deaza L-nucleosides

• US 20060003951A1
• Filed: 06/10/2005
• Published: 01/05/2006
• Est. Priority Date: 12/21/2001
• Status: Abandoned Application

• Current Assignee: Micrologix Biotech Incorporated
• Original Assignee: Micrologix Biotech Incorporated
• Inventors: Mekouar, Khalid, Iyer, Radhakrishnan P., Deziel, Robert, Mounir, Samir
• Application Number:
  US11/150,591
• Publication Number:
  US 20060003951A1
• Time in Patent Office: Days
• US Class Current: 514/43
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/20 for DNA viruses
• CPC Class Codes: C07H 19/044 Pyrrole radicals
• CPC Class Codes: C07H 19/16 Purine radicals
• CPC Class Codes: C07H 19/23 Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22

Abstract

The present invention comprises 7-deaza L-nucleosides having unexpectedly high inhibitory activity against the hepatitis B virus. The invention further comprises pharmaceutical compositions comprising such compounds as well as methods of treating mammals, particularly humans, infected with HBV and other viral infections.

Claims

1-7. -7. (canceled)

8. A compound of formula (I):

and pharmaceutically acceptable salts thereof wherein;

(a) R¹ is C₁-C₄-alkoxy or —

NH₂;

(b) R is —

H, C₁-C₆-alkyl, —

Cl, —

I, —

Br, or —

F;

(c) R³ is —

H or C₁-C₆-alkyl;

(d) R⁴ is —

H or —

NH₂; and

(e) X and Y independently are —

N—

or —

CH—

.

9. The compound according to claim 8 wherein:

(a) R¹ is methoxy or —

NH₂;

(b) R² and R³ are independently —

H, methyl, or —

I;

(c) R₄ is —

H or —

NH₂;

or

(d) X and Y are —

N—

.

10. The compound according to claim 8 wherein:

(a) R¹ is —

NH₂;

(b) R¹ is —

NH₂, R² and R³ independently are —

H or C₁-C₆-alkyl, and R⁴ is —

H;

(c) R¹ is —

NH₂, R² and R³ independently are —

H or methyl, and R⁴ is —

H or —

NH₂;

or

(d) R¹ is —

NH₂, R² and R³ independently are —

H or —

I, and R⁴ is —

H.

11. The compound according to claim 8 wherein R¹ is —

NH₂, R², R³ and R⁴ are —

H, and X and Y are —

N—

.

12. The compound according to claim 8 wherein R¹ is —

NH₂, R² is methyl, R³ is —

H, R⁴ is —

H, and X and Y are —

N—

.

13. The compound according to claim 8 wherein R¹ is methoxy, R² and R³ are —

H, R⁴ is —

NH₂, and X and Y are —

N—

.

14. The compound according to claim 8 wherein R¹ is —

NH₂, R₂ is —

H, R³ is methyl, R⁴ is —

H, and X and Y are —

N—

.

15. The compound according to claim 8 wherein R¹ is —

NH₂, R₂ is —

I, R³ is —

H, R⁴ is —

H, and X and Y are —

N—

.

16. The compound according to claim 8 wherein R¹ is —

NH₂, R² and R³ are —

H, R⁴ is —

NH₂, and X and Y are —

N—

.

17. A pharmaceutical composition comprising a compound according to any one of claims 8-16 and a pharmaceutically acceptable carrier.

18. A method of treating a mammal infected with HBV comprising administering to the mammal an effective amount of a composition according to claim 17.

19. The method according to claim 18 wherein the mammal is a human.