Benzimidazolones and analogues

US6380235B1 · kind B1 · utility

Assignees

• Amerimas Home Products, Inc. · US
• Ligand Pharmaceuticals Incorporated · US

Inventors

• Puwen Zhang · Audubon, US
• Reinhold H. W. Bender · Valley Forge, US
• Jay E. Wrobel · Lawrenceville, US
• Lin Zhi · San Diego, US
• Todd K. Jones · Solana Beach, US
• James P. Edwards · San Diego, US
• Christopher M. Tegley · Thousand Oaks, US

Key dates

• Filing date: Apr 19, 2000
• Grant date: Apr 30, 2002
• Expiry date: Apr 19, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D487/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides compounds and pharmaceutical formulations useful as progesterone receptor agonists and antagonists and having the general formula: wherein:A is O, S, or NR4;B is a bond between A and C═Q, or the moiety CR5R6;R4, R5, R5 are independently selected from H or optionally substituted C1 to C6 alkyl, C2 to C6 alkenyl, C2 to C6 alknyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl, or heterocyclic groups, or cyclic alkyl constructed by fusing R4 and R5 to from a 5 to 7 membered ring; R1 is selected from H, OH, NH2, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C6 alkenyl, substituted C1 to C6 alkenyl, alkynyl, substituted alknyl, —COH, or optionally substituted —CO(C1 to C3 alkyl), —CO(aryl), —CO(C1 to C3 alkoxy), or —CO(C1 to C3 aminoalkyl) groups; R2 is selected from H, halogen, CN, NO2, or optionally substituted C1 to C6 alkyl, C1 to C6 alkoxy, or C1 to C6 aminoalkyl groups; R3 is selected from a trisubstituted benzene ring; or a 5- or 6-membered heteroaromatic ring containing 1 or 2 substituents; Q is O, S, NR8, or CR9R10; or a pharmaceutically acceptable salt thereof. The invention also includes methods…