HIV inhibiting pyrimidines derivatives

US7125879B2 · kind B2 · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

• Paul Adriaan Jan Janssen · Vosselaar, BE
• Patrice Palandjian · Louviers, FR
• Marc René de Jonge · Tilburg, NL
• Lucien Maria Henricus Koymans · Retie, BE
• Hendrik Maarten Vinkers · Ekeren, BE
• Frederik Frans Desiré Daeyaert · Beerse, BE
• Jan Heeres · Vosselaar, BE
• Koen Jeanne Alfons Van Aken · Kortrijk, BE
• Paulus Joannes Lewi · Turnhout, BE
• Jrme Emile Georges Guillemont · Andé, FR

Key dates

• Filing date: Aug 9, 2002
• Grant date: Oct 24, 2006
• Expiry date: Apr 14, 2023

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/12
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention concerns HIV replication inhibitors of formula (I) the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof, wherein the ring containing −a1=a2−a3=a4—and −b1=b2−b3=b4represents pheynl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl; n is 0 to 5; m is 1 to 4; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyl; C1-6alkyloxycarbonyl, substituted C1-6alkyl, C1-6alkylcarbonyl; R2 is hydroxy, halo, optionally substituted C1-6alkyl, C3-7cycloalkyl, optionally substituted C2-6alkenyl, optionally substituted C2-6alkynyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, —S(═O)pR6, —NH—S(═O)pR6, —C(═O)R6, —NHC(═O)H, —C(═O)NHNH?2?, —NHC(═O)R6, —C(═NH)R6 or a 5-membered hetrocycl; X1 is —NR5—, —NH—NH—, —N═N—, —O—, —C(═O)—, C1-4alkanediyl, —CHOH—, —S—, —S(═O)p—, —X2—C1-4alkanediyl- or —C1-4alkanediyl-X2—; R3 is NHR13, NR13R14; —C(═O)—NHR13; —C(═O)—NR13R14; —C(═O)—R15; —CH═N—NH—C(═O)—R16; substituted C1-6alkyl; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl; substituted C2-6alkyn…