Fused imidazole derivatives as multidrug resistance modulators

US6218381A · kind A · utility

Assignee

• Janssen Pharmaceutica NA · BE

Inventors

• Frans Eduard Janssens · Bonheiden, BE
• Joseph Elisabeth Leenaerts · Rijkevorsel, BE
• François Maria Sommen · Wortel, BE
• Dominique Louis Nestor Ghislain Surleraux · Braine-le-Comte, BE

Key dates

• Filing date: Sep 17, 1998
• Grant date: Apr 17, 2001
• Expiry date: Sep 17, 2018

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D495/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention concerns the compounds of formula ##STR1## the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein the dotted line is an optional bond; n is 1 or 2; R.sup.1 is hydrogen; halo; formyl; C.sub.1-4 alkyl optionally substituted with hydroxy, C.sub.1-4 alkyloxy, C.sub.1-4 alkylcarbonyloxy, imidazolyl, thiazolyl or oxazolyl; or a radical of formula --X--COOR.sup.5, --X--CONR.sup.6 R.sup.7 or --X--COR.sup.10 wherein --X-- is a direct bond, C.sub.1-4 alkanediyl or C.sub.2-6 alkenediyl; R.sup.5 is hydrogen, C.sub.1-12 alkyl, Ar, Het, C.sub.1-6 alkyl substituted with C.sub.1-4 alkyloxy, aryl or heteroaryl; R.sup.6 and R.sup.7 each independently are hydrogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, halo, C.sub.1-4 alkyl, hydroxyC.sub.1-4 alkyl, C.sub.1-4 alkyloxycarbonyl, carboxyl, formyl or phenyl; R.sup.3 is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyloxy; R.sup.4 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy or haloC.sub.1-4 alkyl; Z is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --CHOH--CH.sub.2 --, --O--CH.sub.2 --, --C(.dbd.O)--CH.sub.2 -- or --C(.dbd.NOH)--CH.sub.2 --; --A--B-- is a bi…