2′,4′-substituted nucleosides as antiviral agents

• US 9,296,777 B2
• Filed: 04/30/2014
• Issued: 03/29/2016
• Est. Priority Date: 11/20/2007
• Status: Active Grant

• Current Assignee: Gilead Sciences Inc.
• Original Assignee: Gilead Pharmasset LLC (Gilead Sciences Inc.)
• Inventors: Sofia, Michael Joseph, Du, Jinfa
• Primary Examiner(s): McIntosh, III, Traviss C
• Application Number:
  US14/265,840
• Publication Number:
  US 20140235563A1
• Time in Patent Office: 699 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 31/7064 containing condensed or non-condensed pyrimidines
• 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: A61K 31/7076 containing purines, e.g. adenosine, adenylic acid
• 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 31/18 for HIV
• CPC Class Codes: A61P 31/20 for DNA viruses
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/073 with 2-deoxyribosyl as the saccharide radical
• CPC Class Codes: C07H 19/14 Pyrrolo-pyrimidine radicals
• CPC Class Codes: C07H 19/16 Purine radicals
• CPC Class Codes: C07H 19/173 with 2-deoxyribosyl as the saccharide radical

Abstract

Embodiments of the invention are to compounds, methods, and compositions for use in the treatment of viral infections. More specifically embodiments of the invention are 2′,4′-substituted nucleoside compounds useful for the treatment of viral infections, such as HIV, HCV, and HBV infections.

Claims

1. A compound of the following formula:

2. The compound of claim 1, wherein R² is F;

R is H; and

R³ is OH.

3. The compound of claim 2, wherein R⁴ is a lower alkyl, CH₂F, N₃, halogen, alkenyl, alkynyl, or Br-vinyl.

4. The compound of claim 3, wherein R⁴ is N₃.

5. The compound of claim 3, wherein R⁴ is a lower alkyl.

6. The compound of claim 5, wherein R⁴ is an ethyl.

7. The compound of claim 3, wherein R⁵ and R⁶, are independently H, OH, NH₂, or alkyl of C₁-C₆.

8. The compound of claim 7, wherein R⁵ is NH₂, and R⁶ is H.

9. The compound of claim 4, wherein the compound is:

10. A compound of the following formula:

11. The compound of claim 10, wherein the compound is selected from the group consisting of: