Broadspectrum substituted benzimidazole sulfonamide HIV protease inhibitors

US8143421B2 · kind B2 · utility

Assignee

• Tibotec Pharmaceuticals Ltd. · IE

Inventors

• Dominique Louis Nestor Ghislain Surleraux · Braine-le-Comte, BE
• Piet Tom Bert Paul Wigerinck · Terhagen, BE
• Marieke Voets · Herent, BE
• Sandrine Marie Helene Vendeville · Woluwe-Saint-Pierre - Sint-Pieters-Woluwe, BE
• Herman Augustinus De Kock · Arendonk, BE
• Bernhard Joanna Bernard Vergouwen · Maaseik, BE

Key dates

• Filing date: Apr 27, 2009
• Grant date: Mar 27, 2012
• Expiry date: Feb 2, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/04
• WIPO field: Pharmaceuticals
• 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, C3-7cycloalkyl, 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)—, —O—C1-6alkanediyl-C(═O)—, —NR8—C1-6alkanediyl-C(═O)—, —S(═O)2—, —O—S(═O)2—, —NR8—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), C3-7cycloalkyl, C2-6alkenyl, C2-6alkynyl or optionally substituted C1-6alkyl; A is C1-6alkanediyl, —C(═O)—, —C(═S)—, —S(═O)2—, C1-6alkanediyl-C(═O)—, C1-6alkanediyl-C(═S)— or C1-6alkanediyl-S(═O)2—; R5 is H, OH, C1-6alkyl, Het1C1-6alkyl, Het2C1-6alkyl, optionally substituted amino-C1-6alkyl; R6 is C1-6alkylO, Het1, Het1O, Het2, Het2O, aryl, arylO, C1-6alkyloxy-carbonylamino or amino; and in case -A- is other than C1-6alkanediyl then R6 may also be C1-6alkyl, Het1C1-4alkyl, Het1OC1-4alkyl, Het2C1-4alkyl, Het2OC1-4alkyl, arylC1-4a…