Pyrrolo[3,2-d]pyrimidine derivatives for the treatment of viral infections and other diseases

• US 10,259,814 B2
• Filed: 10/25/2016
• Issued: 04/16/2019
• Est. Priority Date: 10/10/2012
• Status: Active Grant

• Current Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Original Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Inventors: McGowan, David Craig, Last, Stefaan Julien, Pieters, Serge Maria Aloysius, Embrechts, Werner, Jonckers, Tim Hugo Maria, Raboisson, Pierre Jean-Marie Bernard
• Primary Examiner(s): Balasubramanian, Venkataraman
• Application Number:
  US15/333,947
• Publication Number:
  US 20170044169A1
• Time in Patent Office: 903 Days
• Field of Search: 544280, 5142591
• CPC Class Codes: A61K 31/407 condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
• CPC Class Codes: A61K 31/519 ortho- or peri-condensed with heterocyclic rings
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

This invention concerns pyrrolo[3,2-d]pyrimidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treatment and/or therapy of diseases.

Claims

1. A compound of formula (I)

2. A compound of formula (I) according to claim 1 wherein R₁ and R₂ are each hydrogen.

3. A compound of formula (I) according to claim 1 wherein R₁ is fluorine and R₂ is hydrogen.

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

5. A compound of formula (I) according to claim 1, wherein R₃ is methyl.

6. A compound of formula (I) according to claim 5, wherein R₃ is substituted by a substituent selected from the group consisting of phenyl, pyridinyl, thiazolyl and pyrimidinyl.

7. A compound of formula (I) according to claim 6, wherein each substituent is optionally further substituted by methoxy or halogen.

8. A compound of formula (I) according to claim 1, wherein R₄ is methyl.

9. A compound of formula (I) according to claim 8, wherein R₄ is substituted by oxadiazolyl or isoxazolyl.

10. A compound of formula (I) according to claim 9, wherein each substitutent is optionally further substituted by methyl.

11. A compound of formula (I) according to claim 1, wherein R₃ and R₄ are each methyl.

12. A compound of formula (I) according to claim 1, wherein R₃ is substituted with pyridinyl, and R₄ is substituted with isoxazolyl.

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

15. A pharmaceutical composition comprising a compound according to claim 13 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

18. A method of treating HCV infection in a subject in need thereof comprising administering to said subject an effective amount of a compound of claim 1, wherein administering said compound to said subject induces interferon.

19. A method of treating HCV infection in a subject in need thereof comprising administering to said subject an effective amount of a compound of claim 13, wherein administering said compound to said subject induces interferon.

14. A compound selected from the group consisting of

16. A pharmaceutical composition comprising a compound according to claim 14 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

20. A method of treating HCV infection in a subject in need thereof comprising administering to said subject an effective amount of a compound of claim 14, wherein administering said compound to said subject induces interferon.

17. A method of treating HCV infection in a subject in need thereof comprising administering to said subject an effective amount of a compound of formula (I)