HIV inhibiting 5-carbo- or heterocyclic substituted pyrimidines

US7531548B2 · kind B2 · utility

Assignee

• Tibotec Pharmaceuticals Ltd. · IE

Inventors

• Jérôme Emile Georges Guillemont · Andé, FR
• Jan Heeres · Vosselaar, BE
• Paulus Joannes Lewi · Turnhout, BE

Key dates

• Filing date: Sep 29, 2005
• Grant date: May 12, 2009
• Expiry date: Sep 29, 2025

Classification

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

Abstract

HIV replication inhibitors of formula (I) N-oxides, a pharmaceutically acceptable addition salts, a quaternary amines or a stereoisomeric forms thereof, wherein -a1=a2-a3=a4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; -b1=b2-b3=b4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; optionally substituted C1-6alkyl; C1-6alkyloxycarbonyl; R2 is OH; halo; optionally substituted C1-6alkyl, C2-6alkenyl or C2-6alkynyl; substituted carbonyl; carboxyl; CN; nitro; amino; substituted amino; polyhalomethyl; polyhalomethylthio; —S(═O)rR6; C(═NH)R6; R2a is CN; amino; substituted amino; optionally substituted C1-6alkyl; halo; optionally substituted C2-6alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R16; optionally substituted C1-6alkyloxy C1-6alkyl; substituted C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7 or —X3—R7; X1 is —NR1—, —O—, —C(═O)—, CH2, —CHOH—, —S—, —S(═O)r—; R3 is CN; amino; C1-6alkyl; halo; optionally substituted C1-6alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R16; substituted C1-6alkyl; optionally substituted C1-6alkyloxy C1-6alkyl; substituted C2-6alkenyl or C2-6alkynyl; —C…