Modified fluorinated nucleoside analogues

• US 8,415,322 B2
• Filed: 09/09/2010
• Issued: 04/09/2013
• Est. Priority Date: 05/30/2003
• Status: Expired due to Term

• Current Assignee: Gilead Sciences Inc.
• Original Assignee: Gilead Pharmasset LLC (Gilead Sciences Inc.)
• Inventors: Clark, Jeremy
• Primary Examiner(s): McIntosh, III, Traviss C
• Application Number:
  US12/878,262
• Publication Number:
  US 20110038833A1
• Time in Patent Office: 943 Days
• Field of Search: None
• US Class Current: 514/49
• CPC Class Codes: A61K 31/7068 having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
• CPC Class Codes: A61K 31/7072 having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/14 for RNA viruses
• CPC Class Codes: A61P 31/16 for influenza or rhinoviruses
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• 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 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 19/048 Pyridine radicals
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/14 Pyrrolo-pyrimidine radicals
• CPC Class Codes: C07H 19/16 Purine radicals

Abstract

The disclosed invention provides compositions and methods of treating a Flaviviridae infection, including hepatitis C virus, West Nile Virus, yellow fever virus, and a rhinovirus infection in a host, including animals, and especially humans, using a (2′R)-2′-deoxy-2′-fluoro-2′-C-methyl nucleosides, or a pharmaceutically acceptable salt or prodrug thereof.

Claims

1. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

21. A method as recited in any one of the preceding claims, wherein the antivirally effective amount of the compound is administered in combination or alternation with at least one treatment selected from the group consisting of an antiviral treatment, an antibacterial treatment, an anticancer treatment, and interferon.

2. A method of inhibiting the proliferation of a hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

3. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

4. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

5. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

6. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

7. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

8. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

9. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

10. A method of inhibiting the proliferation of hepatitis C virus in a human subject infected with the virus comprising providing to the subject an antivirally effective amount of a compound of the structure:

11. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

12. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

13. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

14. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

15. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

16. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

17. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

18. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;

19. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound or its-pharmaceutically acceptable salt of the structure;

20. A method for the treatment of a hepatitis C infection, comprising:

providing to a human in need thereof an antivirally effective amount of a compound of the structure;