Broadspecturm 2-amino-benzoxazole sulfonamide HIV protease inhibitors

US7622490B2 · kind B2 · utility

Assignee

• Tibotec Pharmaceuticals Ltd. · IE

Inventors

• Dominique Louis Nestor Ghislain Surleraux · Braine-le-Comte, BE
• Sandrine Marie Helene Vendeville · Woluwe-Saint-Pierre - Sint-Pieters-Woluwe, BE
• Wim Gaston Verschueren · Berchem, BE
• Marie-Pierre De Bethune · Everberg, BE
• Herman Augustinus De Kock · Arendonk, BE
• Abdellah Tahri · Anderlecht, BE

Key dates

• Filing date: May 10, 2002
• Grant date: Nov 24, 2009
• Expiry date: Jul 15, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D513/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention concerns the compounds having the formulaN-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein R1 and R8 each are H, optionally substituted C1-6alkyl, C2-6alkenyl, C3-7 cycloalkyl, aryl, Het1, Het2; R1 may also be a radical of formula (R11aR11b)NC(R10aR10b)CR9—; t is 0, 1 or 2; R2 is H or C1-6alkyl; L is —C(═O)—, —O—C(═O)—, —NR8—C(═O)—, —C1-6alkanediyl-C(═O)—, —NR8—C1-6alkanediyl-C(═O)—, —S(═O)2—, —O—S(═O)2—, —NR9-S(═O)2; R3 is C1-6alkyl, aryl, C3-7cycloalkyl, C3-7cycloalkylC1-4alkyl, or arylC1-4alkyl; R4 is H, C1-4alkylOC(═O), carboxyl, aminoC(═O), mono- or di(C1-4alkyl)aminoC(═O), C3-7 cycloalkyl, C2-6alkenyl, C2-6alkynyl or optionally substituted C1-6alkyl; R5 and R6 are H or C1-6alkyl. It further relates to their use as broadspectrum HIV protease inhibitors, processes for their preparation as well as pharmaceutical compositions and diagnostic kits comprising them. It also concerns combinations thereof with another anti-retroviral agent, and to their use in assays as reference compounds or as reagents.