Substituted pyrimidines as toll-like receptor modulators

Patent metadata

Field	Value
Publication number	US-9284304-B2
Application number	US-201314420066-A
Country	US
Kind code	B2
Filing date	Aug 9, 2013
Priority date	Aug 10, 2012
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

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

First claim

The invention claimed is:

1. A compound of formula (I)

or a pharmaceutically acceptable salt thereof, wherein
R 1 is hydrogen, fluoro, hydroxy, amino, C 1-6 alkyl, C 1-6 alkylamino, C 1-6 alkoxy, C 3-7 cycloalkyl, C 4-7 heterocyclyl, aryl, bicyclic heterocyclyl, arylalkyl, heteroaryl, heteroarylalkyl, aryloxy, heteroaryloxy, carboxy, carboxy ester, or amido each of which is optionally substituted by one or more substituents independently selected from halo, hydroxy, amino, di-(C 1-6 )alkylamino, (C 1-4 )alkoxy-(C 1-4 )alkyl, C 1-6 alkylamino, C 1-6 alkyl, C 1-6 alkoxy, C 3-6 cycloalkyl, carboxy, carboxy ester, amido, heterocyclyl, aryl, alkenyl, alkynyl, arylalkyl, heteroaryl, heteroarylalkyl, or cyano,
R 2 is C 1-6 alkyl, which is optionally substituted by one or more substituents independently selected from halo, hydroxy, amino, cyano, carboxy, carboxy ester, amido, C 1-3 alkyl, C 1-3 alkoxy or C 3-6 cycloalkyl,
with the proviso that N-(2-amino-5-phenethylpyrimidin-4-yl)-N-pentylamine is excluded.

2. A compound of formula (I)

or a pharmaceutically acceptable salt thereof, wherein
R 1 is a heterocyclyl, and
R 2 is C 1-6 alkyl substituted by one or more hydroxy.

3. The compound as claimed in claim 1 , wherein
R 1 is hydrogen, and
R 2 is optionally substituted by one or more substituents independently selected from halo, hydroxy, amino, cyano, carboxy, carboxy ester, amido, C 1-3 alkyl, C 1-3 alkoxy, or C 3-6 cycloalkyl.

4. A pharmaceutical composition comprising a compound as claimed in claim 1 or a pharmaceutically acceptable salt thereof together with one or more pharmaceutically acceptable excipients, diluents or carriers.

5. A method for modulating toll-like receptor 7 activity and/or toll-like receptor 8 activity in a human, comprising administering to said human a therapeutically effective amount of at least one compound as claimed in claim 1 .

6. A compound selected from the group consisting of:

Assignees

• Janssen Sciences Ireland Uc

Inventors

• Mcgowan David Craig
• Jonckers Tim Hugo Maria
• Raboisson Pierre Jean-Marie Bernard

Classifications

• A61P37/02

  Immunomodulators · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• A61P31/12

  Antivirals · CPC title

• A61P31/00

  Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics · CPC title