Benzimidazoline-2-one-1-carboxylic acid derivatives useful...

C - Chemistry – Metallurgy – 07 – D

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C07D 451/00 (2006.01) A61K 31/44 (2006.01) C07D 401/12 (2006.01) C07D 451/12 (2006.01) C07D 451/14 (2006.01) C07D 453/02 (2006.01) C07D 453/06 (2006.01) C07D 487/08 (2006.01)

Patent

CA 1337347

Pharmaceutically active benzimidazoline-2-oxo-1-carbo- xylic acid derivatives are described which are 5- HT receptor antagonists useful as antiemetic agents and as gastric prokinetic agents, of the following formula: Image (I) wherein R represents a hydrogen atom, or a C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl group; R1 and R2, which may be the same or different, represent a hydrogen atom, halogen atom, trifluoromethyl, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, C1-6 acyl, carboxyl, C1-6 alkoxycarbonyl, hydroxy, nitro, or amino group, optionally N-mono or di-substituted by a C1-4 alkyl group, C1-6 acylamino, C1-6 alkoxycar- bonylamino, carbamoyl optionally N-mono or di-substitu- ted by C1-4 alkyl group, cyano, C1-6 alkylsulphinyl, C1-6 alkylsulphonyl, aminosulphonyl optionally N- mono or di-substituted by a C1-4 alkyl group, aminosul- phonylamino optionally N-mono or di-substituted by C1-4 alkyl group; Y is oxygen or represents N - R3 in which R3 is a hydrogen atom, a C1-6 alkyl or benzyl group, optionally substituted by one or more C1-6 alkoxy groups; A is a group selected from: Image (a) Image (b) Image (c) Image (d) wherein p is 0 or 1; r is 0, 1, 2, or 3; R4 is a hydrogen atom or a C1-4 alkyl group; R5 is a hydrogen atom, C1-6 alkyl, C3-8 cycloalkyl, a C3-8 cycloalkylalkyl group having 1-4 carbons in the alkyl moiety or a phenylalkyl group having 1-4 carbons in the alkyl moiety or R5 is a group of formula Image wherein R6 is a hydrogen atom, C1-4 alkyl or an amino group and R7 is a hydrogen atom or C1-6 alkyl group. The processes for the preparation of the compounds of formula (I) as well as pharmaceutical compositions containing them are also described.

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