1,2,4-triazine derivatives for the treatment of viral infections

• US 9,416,114 B2
• Filed: 10/01/2013
• Issued: 08/16/2016
• Est. Priority Date: 10/01/2012
• Status: Active Grant

• Current Assignee: Centre National De La Recherche Scientifique, Institut National Des Sciences Appliquees De Rouen (INSA), Universite de Rouen
• Original Assignee: Centre National De La Recherche Scientifique, Institut National Des Sciences Appliquees De Rouen (INSA), Universite de Rouen
• Inventors: Hoarau, Christophe, Bonfanti, Jean-Francois, McGowan, David Graig, Guillemont, Jerome Emile Georges, Gembus, Vincent, Jubault, Philippe, Levacher, Vincent
• Primary Examiner(s): Balasubramanian, Venkataraman
• Application Number:
  US14/432,269
• Publication Number:
  US 20150336907A1
• Time in Patent Office: 1,050 Days
• Field of Search: 544/182, 514/242
• US Class Current: 1/1
• 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 37/00 Drugs for immunological or allergic disorders
• CPC Class Codes: C07D 253/07 with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 253/075 Two hetero atoms, in positions 3 and 5
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links

Abstract

This invention relates to 1,2,4-triazine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treating viral infections.

Claims

1. A compound of formula (I)

2. The compound according to claim 1 wherein R₂ is butyl or pentyl and wherein R₁ is C_1-6alkyl, arylalkyl, heteroarylalkyl each of which is optionally substituted by one or more substituents independently selected from 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, di-(C_1-6)alkylamino, C_1-6 alkylamino, aryl, alkenyl, alkynyl, arylalkyl, heteroaryl, heteroarylalkyl and nitrile.

3. The compound according to claim 1 wherein R₂ is C_1-8 alkyl substituted with hydroxyl, and wherein R₁ is a substituted or unsubstituted arylalkyl group.

4. The compound according to claim 1 wherein R₁ is an arylalkyl and R₂ is C_1-8 alkyl substituted with a hydroxyl, or one of the following examples in any stereochemical configuration:

5. The compound according to claim 1 wherein R₁ is CH₃ and wherein R₂ is C_1-8 alkyl, optionally substituted by one or more substituents independently selected from halogen, hydroxyl, amino, C_1-3 alkyl, C_1-3 alkoxy, C_3-6 cycloalkyl, carboxylic acid, carboxylic ester, carboxylic amide, di-(C_1-6)alkylamino, C_1-6 alkylamino, aryl, heteroaryl, heteroarylalkyl and nitrile.

6. The compound according to claim 1 wherein R₁ is a heteroarylalkyl, and wherein R₂ is C_1-8 alkyl, optionally substituted by one or more substituents independently selected from halogen, hydroxyl, amino, C_1-3 alkyl, C_1-3 alkoxy, C_3-6 cycloalkyl, carboxylic acid, carboxylic ester, carboxylic amide, di-(C_1-6)alkylamino, C_1-6 alkylamino, aryl, heteroaryl, heteroarylalkyl and nitrile.

7. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt, tautomer(s), or solvate thereof according to claim 1 together with one or more pharmaceutically acceptable excipients, diluents or carriers.