HIV inhibiting 1,2,4-triazin-6-one derivatives

US7923554B2 · kind B2 · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

• Georges Joseph Cornelius Hoornaert · Kessel-Lo, BE
• Amuri Kilonda · Tienen, BE
• Jan Heeres · Vosselaar, BE
• Paulus Joannes Lewi · Turnhout, BE
• Marc René de Jonge · Tilburg, NL
• Frederik Frans Desiré Daeyaert · Beerse, BE
• Hendrik Maarten Vinkers · Ekeren, BE
• Lucien Maria Henricus Koymans · Retie, BE
• Paul Adriaan Jan Janssen · Vosselaar, BE

Key dates

• Filing date: Aug 10, 2005
• Grant date: Apr 12, 2011
• Expiry date: Oct 26, 2027

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P31/18
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to HIV replication inhibitors of formulaa N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine or a stereochemically isomeric form thereof, wherein ring A and ring B represent phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl; n and m are 1 to 4; R1 represents hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyloxycarbonyl; optionally substituted C1-6alkyl; C1-6alkyloxyC1-6alkylcarbonyl substituted with C1-6alkyloxycarbonyl; R2 or R4 represents hydrogen; hydroxy; halo; optionally substituted C1-6alkyl; optionally substituted C2-6alkenyl; optionally substituted C2-6alkynyl; C3-7cycloalkyl; C1-6alkyloxy; C1-6alkyloxycarbonyl; C1-6alkylcarbonyloxy; carboxyl; cyano; nitro; amino; mono- or di(C1-6alkyl)amino; polyhaloC1-4alkyl; polyhaloC1-4alkyloxy; polyhaloC1-4alkylthio; —S(═O)pR6; —NH—S(═O)pR6; —C(═O)R6; —NHC(═O)H; —C(═O)NHNH2; NHC(═O)R6; C(═NH)R6; or R7; R2a or R3 represents cyano; aminocarbonyl; amino; halo; NHR13; NR13R14; —C(═O)—NHR13; —C(═O)—NR13R14; —C(═O)—R15; —CH═N—NH—C(═O)—R16; optionally substituted C1-6alkyl; optionally substituted C1-6alkyloxy; optionally substituted C1-6alkyloxyC1-6alkyl; optionally substituted C2-6al…