HIV replication inhibiting pyrimidines

US8530655B2 · kind B2 · utility

Assignee

• Janssen Pharmaceuticals, Inc. · BE

Inventors

• Bart De Corte · Southampton, US
• Marc René de Jonge · Tilburg, NL
• Jan Heeres · Vosselaar, BE
• Chih Yung Ho · Lansdale, US
• Paul Adriaan Jan Janssen · Vosselaar, BE
• Robert W. Kavash · Glenside, US
• Lucien Maria Henricus Koymans · Retie, BE
• Michael Joseph Kukla · Masontown, US
• Donald Ludovici · Quakertown, US
• Koen Jeanne Alfons Van Aken · Kortrijk, BE
• Koenraad Jozef Lodewijk Marcel Andries · Beerse, BE

Key dates

• Filing date: Jul 6, 2011
• Grant date: Sep 10, 2013
• Expiry date: Jul 6, 2031

Classification

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

Abstract

This invention concerns the use of compounds of formulathe N-oxides, the pharmaceutically acceptable addition salts, quaternary amines and the stereochemically isomeric forms thereof, wherein -a1=a2-a3=a4- forms a phenyl, pyridinyl, pyrimidinyl, pyridazinyl or pyrazinyl with the attached vinyl group; n is 0 to 4; and where possible 5; R1 is hydrogen, aryl, formyl, C1-6alkylcarbonyl, C1-6alkyl, C1-6alkyloxycarbonyl, substituted C1-6alkyl, or substituted C1-6alkyloxyC1-6alkylcarbonyl; each R2 independently is hydroxy, halo, optionally substituted C1-6alkyl, C2-6alkenyl or C2-6alkynyl, C3-7cycloalkyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C1-6alkylamino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, —S(═O)pR6, —NH—S(═O)pR6, —C(═O)R6, —NHC(═O)H, —C(═O)NHNH2, —NHC(═O)R6, —C(═NH)R6 or a 5-membered heterocyclic ring; p is 1 or 2; L is optionally substituted C1-10alkyl, C2-10alkenyl, C2-10alkynyl or C3-7cycloalkyl; or L is —X—R3 wherein R3 is optionally substituted phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl; X is —NR1—, —NH—NH—, —N═N—, —O—, —C(═O)—, —CHOH—, —S—, —S(═O)— or —S(═O)2—; Q is hydrogen, C1-6alkyl, halo, polyhalo-C1-…