Angiogenesis inhibiting 5-substituted-1,2,4,-thiadiazolyl derivatives

US6833369B2 · kind B2 · utility

Assignee

• Janssen Pharmaceuticals, Inc. · BE

Inventors

• Raymond A. Stokbroekx · Beerse, BE
• Marc André Ceusters · Diest, BE
• Marcel Jozef Maria Van der Aa · Kasterlee, BE
• Marcel G. M. Luyckx · Geel, BE
• Marc Willems · Beerse, BE
• Robert W. Tuman · Spring House, US

Key dates

• Filing date: Oct 19, 2001
• Grant date: Dec 21, 2004
• Expiry date: Oct 19, 2021

Classification

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

Abstract

This invention concerns compounds of formula the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein X is CH or N; R1 is hydrogen, C1-6alkyl, C1-6alkyloxy, C1-6alkylthio, amino, mono- or di(C1-6alkyl)amino, Ar1, Ar1NH—, C3-6cycloalkyl, hydroxymethyl or benzyloxymethyl; R2 is hydrogen, C1-6alkyl, amino, aminocarbonyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl, C1-6alkylcarbonylamino, hydroxy or C1-6alkyloxy; R3, R4 and R5 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, trifluoromethyl, nitro, amino, cyano, azido, C1-6alkyloxyC1-6alkyl, C1-6alkylthio, C1-6alkyloxycarbonyl or Het1; is Ar2, Ar2CH2— or Het2; Ar1 and Ar2 optionally substituted phenyl; Het1 and Het2 are optionally substituted monocyclic heterocycles; having angiogenesis inhibiting activity; their preparation, compositions containing them and their use as a medicine.