Pyrimidine derivatives for the treatment of viral infections

• US 9,422,250 B2
• Filed: 04/10/2012
• Issued: 08/23/2016
• Est. Priority Date: 04/08/2011
• Status: Active Grant

• Current Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Original Assignee: Janssen Sciences Ireland UC (Johnson & Johnson)
• Inventors: Mc Gowan, David, Raboisson, Pierre Jean-Marie Bernard, Embrechts, Werner, Jonckers, Tim Hugo Maria, Last, Stefaan Julien, Pieters, Serge Maria Aloysius, Vlach, Jaromir
• Primary Examiner(s): Wilson, James O
• Assistant Examiner(s): Sackey, Ebenezer O
• Application Number:
  US14/110,054
• Publication Number:
  US 20140045849A1
• Time in Patent Office: 1,596 Days
• Field of Search: 514/235.8, 514/272, 514/252.02, 514/255.05, 514/249, 544/298, 544/123, 544/238, 544/295
• US Class Current: 1/1
• CPC Class Codes: A61K 31/505 Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
• CPC Class Codes: A61K 31/506 not condensed and containing further heterocyclic rings
• CPC Class Codes: A61K 31/513 having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
• CPC Class Codes: A61K 31/5377 not condensed and containing further heterocyclic rings, e.g. timolol
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: C07D 239/48 Two nitrogen atoms
• CPC Class Codes: C07D 401/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/12 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 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems

Abstract

This invention relates to pyrimidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treating viral infections such as HCV or HBV.

Claims

1. A compound of formula (I)

2. A compound as claimed in claim 1 wherein R₃ is butyl or pentyl.

3. A compound as claimed in claim 1 wherein R₃ is C_4-8alkyl substituted with hydroxyl.

4. A compound as claimed in claim 3 wherein R₃ is selected from the group consisting of:

5. A compound as claimed in claim 1 wherein R₁ is hydrogen or —

CH₃.

6. A compound as claimed in claim 1 wherein R₂ is arylalkyl or heteroarylalkyl, each of which is independently, optionally substituted by one or more substituents selected from the group consisting of C_1-3alkyl, hydroxyl, alkoxy, nitrile, heterocycle and ester.

7. A compound of formula (I) according to claim 1 wherein R₂ is selected from the group consisting of:

8. A compound as claimed in claim 1 selected from the group consisting of:

9. A pharmaceutical composition comprising a compound as claimed in claim 1 or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof, and one or more pharmaceutically acceptable excipients, diluents or carriers.

10. A compound of claim 1 having the formula:

11. A compound of claim 1 having the formula:

12. A compound of claim 1 having the formula:

13. A pharmaceutical composition comprising the compound of claim 10 or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof.

14. A pharmaceutical composition comprising the compound of claim 11 or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof.

15. A pharmaceutical composition comprising the compound of claim 12 or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof.