Cyclocarbamate derivatives as progesterone receptor modulators

US6509334B1 · kind B1 · utility

Assignees

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

Inventors

• Puwen Zhang · Audubon, US
• Eugene A. Terefenko · Quakertown, US
• Andrew Fensome · Wayne, US
• Jay E. Wrobel · Lawrenceville, US
• Horace Fletcher, III · Pottstown, 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: Jan 21, 2003
• Expiry date: Apr 19, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention provides compounds of Formula (I): wherein R1 and R2 may be single substituents or fused to form spirocyclic or hetero-spirocyclic rings; R3 is H, OH, NH2, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C6 alkenyl, substituted C1 to C6 alkenyl, alkynyl, or substituted alkynyl, CORC; RC is H, C1 to C3 alkyl, substituted C1 to C3 alkyl, aryl, substituted aryl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, or substituted C1 to C3 aminoalkyl; R4 is H, halogen, CN, NO2, C1 to C6 alkyl, substituted C1 to C6 alkyl, alkynyl, or substituted alkynyl, C1 to C6 alkoxy, substituted C1 to C6 alkoxy, amino, C1 to C6 aminoalkyl, or substituted C1 to C6 aminoalkyl; and R5 is selected from a trisubstituted benzene ring of a five or six membered ring with 1, 2, or 3 heteroatoms from the group including O, S, SO, SO2 or NR6 and containing one or two independent substituents from the group including H, halogen, CN, N02, amino, and C1 to C3 alkyl, C1 to C3 alkoxy, C1 to C3 aminoalkyl, CORF, or NRGCORF; or pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions and methods using the compounds as antagonists of the progesterone receptor.