Angiogenesis inhibiting pyridazinamines

US5985878A · kind A · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

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

Key dates

• Filing date: Jul 9, 1998
• Grant date: Nov 16, 1999
• Expiry date: Jul 9, 2018

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 the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein X is CH or N; m is 2 or 3 and n is 1, 2 or 3; wherein 1 or 2 C-atoms of the CH.sub.2 groups of the ##STR1## moiety which may also contain one double bond, may be substituted with C.sub.1-6 alkyl, amino, aminocarbonyl, mono- or di(C.sub.1-6 alkyl)amino, C.sub.1-6 alkyloxycarbony, C.sub.1-6 alkylcarbonylamino, hydroxy or C.sub.1-6 alkyloxy; and/or 2 C-atoms of said CH.sub.2 groups may be bridged with C.sub.2-4 alkanediyl; 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, ArNH--, 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--; in case X represents CH then L is a radical L.sup.1, L.sup.2 or L.sup.3 ; or in case X represents N then L is a radical L.sup.2 or L.sup.3 ; L.sup.1 is Ar-C.sub.1-6 alkyloxy, Ar-oxy, Ar-thio, Ar-carbonylamino, di-Ar-methyloxy-, N-Ar-piperazinyl, N-Ar-homopiperazinyl, 2-benzimidazolinonyl, Ar--NR.sup.…