Thieno[3,2-d]pyrimidines derivatives for the treatment of viral infections

• US 10,316,043 B2
• Filed: 01/30/2017
• Issued: 06/11/2019
• Est. Priority Date: 07/30/2013
• Status: Active Grant

• Current Assignee: Janssen Sciences Ireland Unlimited Company (Johnson & Johnson)
• Original Assignee: Janssen Sciences Ireland Unlimited Company (Johnson & Johnson)
• Inventors: McGowan, David Craig, Raboisson, Pierre Jean-Marie Bernard
• Primary Examiner(s): Murray, Jeffrey H
• Application Number:
  US15/420,055
• Publication Number:
  US 20170298079A1
• Time in Patent Office: 862 Days
• Field of Search: 5142601, 544278
• CPC Class Codes: A61K 31/519 ortho- or peri-condensed with heterocyclic rings
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: A61P 37/04 Immunostimulants
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 495/04 Ortho-condensed systems

Abstract

This invention relates to thieno[3,2-d]pyrimidines derivatives, processes for their preparation, pharmaceutical compositions, and their use in treating viral infections.

Claims

1. A compound of formula (I)

2. A compound according to claim 1 wherein R₁ and R₂ are both hydrogen and wherein R₃ is C_1-8 alkyl substituted by hydroxyl.

3. The compound of claim 1, wherein R₁ and R₂ are each hydrogen.

4. The compound of claim 1, wherein at least one of R₁ and R₂ is methyl.

5. The compound of claim 1, wherein R₁ is hydrogen.

6. The compound of claim 1, wherein R₁ is methyl.

7. The compound of claim 1, wherein R₂ is hydrogen.

8. The compound of claim 1, wherein R₂ is methyl.

9. The compound of claim 1, wherein R₂ is t-butyl.

10. The compound of claim 1, wherein R₃ is C_1-8 alkyl substituted by hydroxyl.

11. The compound of claim 1, wherein R₃ is C_1-8 alkyl substituted by C_1-6 alkoxy.

12. The compound of claim 1, wherein R₃ is C_1-8 alkyl substituted by carboxylic acid.

13. The compound of claim 1, wherein R₃ is C_1-8 alkyl substituted by carboxylic ester.

14. The compound of claim 1, wherein R₁ and R₂ are each hydrogen, and R₃ is C_1-8 alkyl.

15. The compound of claim 1, wherein R₁ and R₂ are each hydrogen, and R₃ is C_1-8 alkyl substituted by hydroxyl.

16. The compound of claim 1, wherein at least one of R₁ and R₂ is methyl, and R₃ is C_1-8 alkyl.

17. The compound of claim 1, wherein at least one of R₁ and R₂ is methyl, and R₃ is C_1-8 alkyl substituted by hydroxyl.

18. A pharmaceutical composition comprising a compound according to claim 1 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

19. A method of treating a viral infection in a subject, said method comprising administering to said subject the pharmaceutical composition according to claim 18, wherein at least one of TLR7 and/or TLR8 is activated.

20. A method of treating a viral infection in a subject, said method comprising administering to said subject an effective amount of the compound according to claim 1, wherein at least one of TLR7 and/or TLR8 is activated.