5- or 6-substituted benzimidazole derivatives as inhibitors of respiratory syncytial virus replication

US8278455B2 · kind B2 · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

• Jean-François Bonfanti · Andé, FR
• Koenraad Jozef Lodewijk Marcel Andries · Beerse, BE
• Jérôme Michel Claude Fortin · Igoville, FR
• Philippe Muller · Val-de-Reuil, FR
• Frédéric Marc Maurice Doublet · Isneauville, FR
• Christophe Meyer · Oissel, FR
• Rudy Edmond Willebrords · Merksplas, BE
• Tom Valerius Josepha Gevers · Vosselaar, BE
• Philip Maria Martha Bern Timmerman · Hasselt, BE

Key dates

• Filing date: Oct 17, 2008
• Grant date: Oct 2, 2012
• Expiry date: Nov 17, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D405/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention concerns 5- or 6-substituted-benzimidazole derivatives having inhibitory activity on the replication of the respiratory syncytial virus and having the formulaa prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereochemically isomeric form thereof wherein Q is Ar2, R6, pyrrolidinyl substituted with R6, piperidinyl substituted with R6 or homopiperidinyl substituted with R6, G is a direct bond or optionally substituted C1-10alkanediyl; R1 is Ar1 or a monocyclic or bicyclic heterocycle; one of R2a and R2b is cyanoC1-6alkyl, cyanoC2-6alkenyl, Ar3C1-6alkyl, Het1C1-6alkyl, N(R8aR8b)C1-6alkyl, Ar3C2-6alkenyl, Het1C2-6alkenyl, Ar3aminoC1-6alkyl, Het1aminoC1-6alkyl, Ar3thioC1-6alkyl, Het1thioC1-6alkyl, Ar3sulfonylC1-6alkyl, Het1sulfonylC1-6alkyl, Ar3aminocarbonyl, Het1aminocarbonyl, Ar3(CH2)namino-carbonyl, Het1(CH2)naminocarbonyl, Ar3carbonylamino, Het1carbonylamino, Ar3(CH2)ncarbonylamino, Het1(CH2)ncarbonylamino, and the other one of R2a and R2b is hydrogen; in case R2a is hydrogen, then R3 is hydrogen;in case R2b is hydrogen, the R3 is hydrogen or C1-6alkyl. It further concerns their preparation and compositions comprising them, as well as their …