2′-fluoronucleoside phosphonates as antiviral agents

• US 8,895,531 B2
• Filed: 03/22/2007
• Issued: 11/25/2014
• Est. Priority Date: 03/23/2006
• Status: Expired due to Fees

• Current Assignee: Cocrystal Pharma, Inc.
• Original Assignee: RFS Pharma, LLC (Cocrystal Pharma, Inc.)
• Inventors: Shi, Junxing
• Primary Examiner(s): McIntosh, III, Traviss C
• Application Number:
  US11/726,686
• Publication Number:
  US 20070225249A1
• Time in Patent Office: 2,805 Days
• Field of Search: None
• US Class Current: 514/47
• CPC Class Codes: A61P 31/18 for HIV
• CPC Class Codes: C07F 9/65586 at least one of the hetero rings does not contain nitrogen as ring hetero atom
• CPC Class Codes: C07F 9/65616 containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/16 Purine radicals
• CPC Class Codes: C07H 19/20 with the saccharide radical esterified by phosphoric or polyphosphoric acids

Abstract

The present invention includes compounds and compositions of ®-2′-fluoronucleoside phosphonates, as well as methods to treat HIV, HBV, HCV or abnormal cellular proliferation comprising administering said compounds or compositions.

Claims

1. A compound having a structure consistent with formula (1) or a pharmaceutically acceptable salt thereof,

5. The compound of claim 1 comprising a 2′

-fluoronucleoside phosphonate of the formula;

6. The compound of claim 1 comprising a 2′

-fluoronucleoside phosphonate of the formula;

11. A pharmaceutical composition comprising the compound of claim 1 or 3 and at least one of a pharmaceutically acceptable carrier, diluent, vehicle, and excipient.

12. The pharmaceutical composition of claim 11 further comprising a compound selected from the group consisting of cytokines, protease inhibitors, antiviral agents, proteases, caspase inhibitors, antibodies and protease inhibitors.

13. A method of treating a viral infection, or a symptom thereof in a subject in need thereof comprising administering to the subject an effective amount the composition of claim 11.

14. The pharmaceutical composition of claim 11, further comprising at least one of an enzyme therapy agent and an immune system modulator.

2. A compound having a structure consistent with formula (II) or a pharmaceutically acceptable salt thereof,

4. The compound of claim 2 comprising a 2′

-fluoronucleoside phosphonate of the formula;

3. A compound having a structure consistent with formula (III) or a pharmaceutically acceptable salt thereof,

7. The compound of claim 3 comprising a 2′

-fluoronucleoside phosphonate of the formula;

8. The compound of claim 3 comprising a 2′

-fluoronucleoside phosphonate of the formula;

9. The compound of claim 3 comprising a 2′

-fluoronucleoside phosphonate of the formula;

10. The compound of claim 3 comprising a 2′

-fluoronucleoside phosphonate of the formula;

15. A compound having a structure consistent with formula (II) or a pharmaceutically acceptable salt thereof,

17. A pharmaceutical composition comprising the compound of claim 2, 15, or 16, and at least one of a pharmaceutically acceptable carrier, diluent, vehicle, and excipient.

18. The pharmaceutical composition of claim 17, further comprising a compound selected from the group consisting of cytokines, protease inhibitors, antiviral agents, proteases, caspase inhibitors, antibodies and protease inhibitors.

19. A method of treating a viral infection, or a symptom thereof in a subject in need thereof comprising administering to the subject an effective amount the composition of claim 17.

20. The pharmaceutical composition of claim 17, further comprising at least one of an enzyme therapy agent and an immune system modulator.

16. A compound having a structure consistent with formula (II) or a pharmaceutically acceptable salt thereof,