Substituted 3,4-annelated benzimidazol-2(1h)-ones

Details Substituted 3,4-annelated benzimidazol-2(1h)-ones Substituted 3,4-annelated benzimidazol-2(1h)-ones

C - Chemistry, Metallurgy

07

D

167/209, 167/227

C07D 519/00 (2006.01) A61K 31/47 (2006.01) A61K 31/55 (2006.01)

Patent

CA 2032885

DIR 0456 ABSTRACT The present invention is concerned with compounds of formula 1 Image (1) wherein - R0 is alkyl, alkoxy or alkylthio having 1-4 carbon atoms, hydroxy, halogen, - Z, together with the carbon atom and the nitrogen atom and the intermediate carbon atom, constitutes a heterocy- clic group which consists of 5-8 ring atoms, in which, besides the already present nitrogen atom, a second hetero atom from the group N, O, or S may be present, which ring may be substituted with 1-4 methyl groups or which ring may be annelated with a phenyl group optional- ly substituted with fluorine, or a methyl or methoxy group; - A is a group of formula 2 or 3 Image (2) (3) wherein one of the groups R3, R4 and R5 is hydrogen, alkyl having 1-6 carbon atoms, cycloalkyl having 3-7 carbon atoms, alkenyl having 2-6 carbon atoms or phenyl alkyl having 1-3 carbon atoms in the alkyl group, and the two other groups independently of each other are hydrogen or alkyl having 1-4 carbon atoms, or wherein A is a polycyclic ring system in which one carbon atom is replaced by a tertiary nitrogen atom, for example, a ring system of formula 4, 5 or 6, Image (4) (5) (6) wherein p is an integer having the value 1 or 2, q is an integer having the value 2, 3 or 4, r is an integer having the value 1, 2 or 3, and R6 is alkyl having 1-4 carbon atoms, cycloalkyl having 3-6 carbon atoms, cyclopropylmethyl, allyl, propargyl or benzyl, and - B is an oxygen atom or a group =N-R, wherein R is hydrogen, alkyl having 1-6 carbon atoms or benzyl, or wherein - B-A represents a group of formula 7 Image (7) wherein R3 and R5 have the meanings defined above, and the pharmaceutically acceptable acid addition salts thereof, which are pharmaceutically active as 5-HT receptor antagonists, and pharmaceutical products containing these compounds.

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