Pyrimidine derivatives for the treatment of viral infections

Patent metadata

Field	Value
Publication number	US-9422250-B2
Application number	US-201214110054-A
Country	US
Kind code	B2
Filing date	Apr 10, 2012
Priority date	Apr 8, 2011
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

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.

First claim

What is claimed is:

1. A compound of formula (I)

or a pharmaceutically acceptable salt, tautomer(s), solvate or polymorph thereof, wherein
R 1 is hydrogen, C 1-4 alkyl, cyclopropyl, C 1-6 alkoxy, halogen, hydroxyl, or trifluoromethyl;
R 2 is C 1-8 alkyl optionally substituted by one or more substituents independently selected from the group consisting of halogen, hydroxyl, amino, C 1-6 alkyl, di-(C 1-6 )alkylamino, C 1-6 alkylamino, C 1-6 alkoxy, C 3-6 cycloalkyl, carboxylic acid, carboxylic ester, carboxylic amide, heterocycle, aryl, alkenyl, alkynyl, arylalkyl, heteroaryl, heteroarylalkyl, and nitrile, wherein said aryl, heterocycle, or heteroaryl is further optionally substituted by C 1-3 alkyl, alkoxy, carboxylic ester or carboxylic amide;
and
R 3 is C 4-8 alkyl, C 4-8 alkoxy, C 2-6 alkenyl or C 2-6 alkynyl, each of which is optionally substituted by one or more substituents independently selected from the group consisting of halogen, hydroxyl, amino, C 1-3 alkyl, C 1-3 alkoxy or C 3-6 cycloalkyl, and nitrile.

2. A compound as claimed in claim 1 wherein R 3 is butyl or pentyl.

3. A compound as claimed in claim 1 wherein R 3 is C 4-8 alkyl substituted with hydroxyl.

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

5. A compound as claimed in claim 1 wherein R 1 is hydrogen or —CH 3 .

6. A compound as claimed in claim 1 wherein R 2 is arylalkyl or heteroarylalkyl, each of which is independently, optionally substituted by one or more substituents selected from the group consisting of C 1-3 alkyl, hydroxyl, alkoxy, nitrile, heterocycle and ester.

7. A compound of formula (I) according to claim 1 wherein R 2 is selected from the group consisting of:

each of which is optionally substituted with C 1-6 alkyl, hydroxyl, C 1-6 alkoxy, nitrile, heterocycle or ester.

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:

or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof.

11. A compound of claim 1 having the formula:

or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof.

12. A compound of claim 1 having the formula:

or a pharmaceutically acceptable salt, tautomer, solvate or polymorph thereof.

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.

Assignees

• Mc Gowan David
• Raboisson Pierre Jean-Marie Bernard
• EMBRECHTS Werner
• Jonckers Tim Hugo Maria
• Last Stefaan Julien
• Pieters Serge Maria Aloysius
• Vlach Jaromir
• Janssen Sciences Ireland Uc

Inventors

• Mc Gowan David
• Raboisson Pierre Jean-Marie Bernard
• EMBRECHTS Werner
• Jonckers Tim Hugo Maria
• Last Stefaan Julien
• Pieters Serge Maria Aloysius
• Vlach Jaromir

Classifications

• A61P31/12

  Antivirals · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• A61K31/513

  having oxo groups directly attached to the heterocyclic ring, e.g. cytosine · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title