Heterocyclic substituted 2-amino quinazoline derivatives for the treatment of viral infections

• US 10,253,003 B2
• Filed: 05/10/2017
• Issued: 04/09/2019
• Est. Priority Date: 11/16/2012
• Status: Active Grant

• Current Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Original Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Inventors: Last, Stefaan Julien, McGowan, David Craig, Embrechts, Werner, Pieters, Serge Maria Aloysius, Jonckers, Tim Hugo Maria, Raboisson, Pierre Jean-Marie Bernard
• Primary Examiner(s): Ward, Paul V
• Application Number:
  US15/591,473
• Publication Number:
  US 20170349557A1
• Time in Patent Office: 699 Days
• 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 239/84 Nitrogen atoms
• CPC Class Codes: C07D 239/95 with hetero atoms directly attached in positions 2 and 4
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

This invention relates to heterocyclic substituted 2-amino-quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and their use in treating viral infections.

Claims

1. A method of stimulating the innate immune system of a subject through activation of TLR7 and/or TLR8 of said subject, said method comprising administering to said subject an effective amount of a compound of formula (I)

2. The method of claim 1, wherein R₅ is CH₃, and R₉ and R₁₁ are each independently H or CH₃.

3. The method of claim 1, wherein R₁₃ is H, CH₃ or CH₂CH₃.

4. The method of claim 1, wherein R₁ is

5. The method of claim 4, wherein R₉ is CH₃.

6. The method of claim 4, wherein R₂ is OCH₃ or —

O—

C₂H₄—

O—

CH₃.

7. The method of claim 4, wherein

R₃, R₄, R₁₃ and R₈ are each H;

R₉ is CH₃; and

R₂ is —

O—

(C_1-3)-alkyl-O—

(C_1-3)-alkyl.

8. The method of claim 4, wherein

R₃, R₄, R₁₃ and R₈ are each H;

R₉ is CH₃, and

R₂ is OCH₃.

9. The method of claim 1, wherein R₁ is

10. The method of claim 9, wherein

R₅ is CH₃, and

R₈, R₉, R₁₀ and R₁₁ are each H.

11. The method of claim 1, wherein R₁ is

12. The method of claim 11, wherein

R₅ is CH₃ or CH₂OH.

13. The method of claim 1, wherein R₁ is

14. The method of claim 13, wherein

R₅ is CH₃, and

R₈ and R₉ are each H.

15. The method of claim 1, wherein R₁ is

16. The method of claim 15, wherein

each R₅ is CH₃, and

R₈ and R₉ are each H.

17. The method of claim 4, wherein R₁ is

18. The method of claim 17, wherein each R₁₃ is (C_1-3)-alkyl.

19. The method of claim 1, wherein R₁ is

20. The method of claim 19, wherein each R₁₃ is (C_1-3)-alkyl.

21. The method of claim 1, wherein the compound is selected from the group consisting of

22. The method of claim 1, wherein the compound is together with one or more pharmaceutically acceptable excipients, diluents or carriers in a pharmaceutical composition.