PYRIDONE DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS AND FURTHER DISEASES

• US 20160108021A1
• Filed: 05/23/2014
• Published: 04/21/2016
• Est. Priority Date: 05/24/2013
• Status: Active Grant

• Current Assignee: Janssen Sciences Ireland Unlimited Company (Johnson & Johnson)
• Original Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Inventors: RABOISSON, Pierre Jean-Marie Bernard, MC GOWAN, David Craig
• Granted Patent: US 10,377,738 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• 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 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 401/06 linked by a carbon chain containing only aliphatic carbon atoms

Abstract

This invention relates to pyridone derivatives, processes for their preparation, phamaceutical compositions, and their use in therapy.

Claims

1. A compound of formula (I)

2. A compound of formula (I) according to claim 1 wherein R₁ is n-butyl and wherein R₂, R₃, R₄, and R₅ are hydrogen.

3. A compound of formula (I) according to claim 1 wherein R₁ is n-butyl and wherein R₂ is fused with R₃ to form a ring structure, R₃ is fused with R₄ to form a ring structure, or R₄ is fused with R₅ to form a ring structure.

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

6. 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.

7. The method of claim 6, wherein the disorder is an infectious disease.

8. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl.

9. A compound of formula (I) according to claim 1, wherein R₂, R₃, R₄ and R₅ are each hydrogen.

10. A compound of formula (I) according to claim 1, wherein R₂ and R₃ are each independently hydrogen or CH₃.

11. A compound of formula (I) according to claim 1, wherein R₂ is fused with R₃ to form a ring structure.

12. A compound of formula (I) according to claim 1, wherein R₄ is CF₃ or CH₃.

13. A compound of formula (I) according to claim 1, wherein R₅ is F or hydrogen.

14. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl;

and R₂, R₃, R₄ and R₅ are each hydrogen.

15. A compound of formula (I) according to claim 1, wherein R₂ is CH₃;

and R₃, R₄ and R₅ are each hydrogen.

16. A compound of formula (I) according to claim 1, wherein R₂ is fused with R₃ to form a ring structure;

and R₄ and R₅ are each hydrogen.

17. A compound of formula (I) according to claim 1, wherein R₂, R₄ and R₅ are each hydrogen;

and R₃ is CH₃.

18. A compound of formula (I) according to claim 1, wherein R₂, R₃ and R₅ are each hydrogen;

and R₄ is CF₃ or CH₃.

19. A compound of formula (I) according to claim 1, wherein R₂, R₃ and R₄ are each hydrogen;

and R₅ is F or hydrogen.

20. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl;

R₂ is CH₃, and R₃, R₄ and R₅ are each hydrogen.

21. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl;

R₂ is fused with R₃ to form a ring structure; and

R₄ and R₅ are each hydrogen.

22. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl;

R₂, R₄ and R₅ are each hydrogen; and

R₃ is CH₃.

23. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl;

R₂, R₃ and R₅ are each hydrogen; and

R₄ is CF₃ or CH₃.

24. A compound of formula (I) according to claim 1, wherein R₁ is C_4-6 alkyl;

R₂, R₃ and R₄ are each hydrogen; and

R₅ is F or hydrogen.

25. A compound of formula (I) according to claim 1, wherein R₁ is selected from the group consisting of n-butyl, n-pentyl and n-hexyl.

26. A compound of formula (I) according to claim 1, wherein R₁ is n-butyl, and R₂ is CH₃, and R₃, R₄ and R₅ are each hydrogen.

27. A compound of formula (I) according to claim 1, wherein R₁ is n-butyl, and wherein R₂ is fused with R₃ to form a ring structure.

28. A compound of formula (I) according to claim 1, wherein R₁ is n-butyl;

R₂, R₄ and R₅ are each hydrogen; and

R₃ is CH₃.

29. A compound of formula (I) according to claim 1, wherein R₁ is n-butyl;

R₂, R₃ and R₅ are each hydrogen; and

R₄ is CF₃ or CH₃.

30. A compound of formula (I) according to claim 1, wherein R₁ is n-butyl;

R₂, R₃ and R₄ are each hydrogen; and

R₅ is F or hydrogen.

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

32. 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 31.

33. The method of claim 32, wherein the disorder is an infectious disease.

5. (canceled)

34. A method of preparing a compound of formula 1, said method comprising reacting compounds A, B, C and D as follows: