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

• US 9,556,199 B2
• Filed: 07/29/2014
• Issued: 01/31/2017
• Est. Priority Date: 07/30/2013
• Status: Active Grant

• Current Assignee: Janssen Sciences Ireland Unlimited Company (Johnson & Johnson)
• Original Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Inventors: McGowan, David Craig, Raboisson, Pierre Jean-Marie Bernard
• Primary Examiner(s): Murray, Jeffrey H
• Application Number:
  US14/908,237
• Publication Number:
  US 20160168164A1
• Time in Patent Office: 917 Days
• Field of Search: None
• US Class Current: 1/1
• 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. A compound according to claim 2 having the structure

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

5. A method of treating a disorder in which the modulation of TLR 7 and/or TLR 8 is involved, comprising the administration of a therapeutically effective amount of at least one compound of claim 1.

6. The method of claim 5, wherein the disorder is a viral infection.

7. A compound according to claim 1 having the structure

8. A compound according to claim 1, wherein R₂ is H, CH₃ or C(CH₃)₃.

9. A compound according to claim 1, wherein R₃ is selected from the group consisting of

10. A compound according to claim 1 wherein R₁ is H and R₂ is CH₃.

11. A compound according to claim 1 wherein R₁ is CH₃ and R₂ is H.

12. A compound according to claim 1 wherein R₁ and R₂ are H.

13. A compound according to claim 1, wherein R₃ is selected from the group consisting of

14. A compound according to claim 1, wherein R₃ is

15. A compound according to claim 1, wherein said compound is selected from the group consisting of

16. A compound as claimed in claim 15, selected from the group consisting of

17. A pharmaceutical composition comprising a compound according to claim 15 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

18. A method of treating a disorder in which the modulation of TLR 7 and/or TLR 8 is involved, comprising the administration of a therapeutically effective amount of at least one compound as claimed in claim 15.

19. The method of claim 18, wherein the disorder is a viral infection.

20. A method of preparing a compound of claim 1, wherein said method comprises:

mixing intermediate I with cyanamide in a polar solvent containing acid to form intermediate II