Angiogenesis inhibiting thiadiazolyl pyridazine derivatives

US6265407A · kind A · utility

Assignee

• Janssen Pharmaceutica NA · 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: Aug 14, 2000
• Grant date: Jul 24, 2001
• Expiry date: Aug 14, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention concerns compounds of formula ##STR1## the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.1-6 alkylthio, amino, mono- or di(C.sub.1-6 alkyl)amino, Ar.sup.1, Ar.sup.1 --NH--, C.sub.3-6 cycloalkyl, hydroxymethyl or benzyloxymethyl; R.sup.2 and R.sup.3 are hydrogen, or taken together may form a bivalent radical of formula --CH.dbd.CH--CH.dbd.CH--; R.sup.4, R.sup.5 and R.sup.6 are each independently selected from hydrogen, halo, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, trifluoromethyl, nitro, amino, cyano, azido, C.sub.1-6 alkyloxyC.sub.1-6 alkyl, C.sub.1-6 alkylthio, C.sub.1-6 alkyloxycarbonyl or Het.sup.1 ; or when R.sup.4 and R.sup.5 are adjacent to each other they may be taken together to form a radical of formula --CH.dbd.CH--CH.dbd.CH--; A is a bivalent radical of formula NR.sup.7, NR.sup.7 --Alk.sup.1 --X--, NR.sup.7 --Alk.sup.1 --X--Alk.sup.2 --, O--Alk.sup.1 --X--, O--Alk.sup.1 --X--Alk.sup.2 -- or S--Alk.sup.1 --X--; wherein X is a direct bond, --O--, --S--, C.dbd.O, --NR.sup.8 -- or Het.sup.2 ; R.sup.7 is hydrogen, C.sub.1-6 alky…