Anti-viral 7-deaza D-nucleosides and uses thereof

• US 20050026853A1
• Filed: 07/25/2003
• Published: 02/03/2005
• Est. Priority Date: 07/25/2002
• Status: Abandoned Application

• Current Assignee: Migenix Inc. (Global Gaming Technologies Corp.)
• Original Assignee: Micrologix Biotech Incorporated
• Inventors: Mekouar, Khalid, Deziel, Robert
• Application Number:
  US10/627,586
• Publication Number:
  US 20050026853A1
• 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 19/00 Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
• CPC Class Codes: C07H 19/22 Pteridine radicals

Abstract

The present invention relates generally to anti-viral compounds, particularly anti-viral 7-deaza D-nucleosides and analogues, or derivatives thereof. The invention also relates to the use of such compounds to treat or prevent hepatitis B virus (HBV) infections, and to the use of such compounds to examine the biological mechanisms of HBV infection.

Claims

1. An anti-viral compound and pharmaceutically acceptable salts thereof, according to structural formula (I):

2. The compound according to claim 1 wherein R¹ is NH₂;

R² is a halogen or C₁-C₄ alkyl; and

R³ and R⁴ are hydrogen.

3. The compound according to claim 1 wherein R¹ is NH₂;

R² is hydrogen or a halogen;

R³ is a halogen or C₁-C₄ alkyl; and

R⁴ is hydrogen.

4. The compound according to claim 1 wherein R¹ is NH₂;

each of R² and R³ are independently hydrogen or a halogen; and

R⁴ is C₁-C₄ alkyl.

5. The compound according to claim 1 wherein R¹ is NH₂;

R² and R³ together with the carbon atoms they are attached to form a pentene ring; and

R⁴is hydrogen.

6. The compound according to claim 1 wherein R¹ is hydrogen or C₁-C₄ alkyl;

each of R² and R³ are independently hydrogen or a halogen; and

R⁴ is hydrogen.

7. The compound according to claim 1 wherein R¹ is NH2;

each of R² and R³ are independently hydrogen or a halogen; and

R⁴ is NHZR⁵;

wherein Z and R⁵ are as defined in claim 1.

8. The compound according to claim 1 wherein R⁶, R⁷, R⁸ and R⁹ are hydrogen.

9. The compound according to claim 1 wherein R⁶, R⁸ and R⁹ are hydrogen;

and R⁷ is OH.

10. The compound according to claim 1 wherein R⁶ and R⁹ are hydrogen;

R⁷ is C₁-C₄ alkyl; and

R⁸ is OH.

11. The compound according to claim 1 wherein R⁶ and R⁹ are hydrogen;

R⁷ is NHZR⁵; and

R⁸ is OH;

wherein Z and R⁵ are as defined in claim 1.

12. The compound according to claim 1 wherein R⁶ and R⁹ are hydrogen;

R⁷ is F; and

R⁸ is OH.

13. The compound according to claim 1 wherein R⁶ is C₁-C₄ alkyl, R⁷ and R⁹ are hydrogen;

and R⁸ is OH.

14. The compound according to claim 1 wherein said compound has structure (II):

15. A pharmaceutical composition comprising a compound according to any one of claims 1 to 14 and a pharmaceutically acceptable carrier, excipient or diluent.

16. A method of treating or preventing a viral infection, comprising administering to a subject in need thereof an anti-viral compound according to any one of claims 1 to 14 in an amount effective to treat or prevent a viral infection.

17. The method of claim 16 in which said anti-viral compound is administered orally.

18. The method of claim 16 wherein said anti-viral compound is administered systemically.

19. The method of claim 16 wherein said viral infection is caused by hepatitis B virus (HBV).

20. A method of treating or preventing a viral infection, comprising administering to a subject in need thereof a composition according to claim 15 in an amount effective to treat or prevent a viral infection.