Patent ID: 6660764
Filing Date: 2003-12-09
Classification: A61P,C07D

Abstract:
A carboxylic acid amide of formula I whereinR1 is a hydrogen atom or a C1-3-alkyl group, R2 is a hydrogen, fluorine, chlorine or bromine atom or a C1-3-alkyl group, R3 is a hydrogen atom or a C1-5-alkyl group, A is a bicyclic heteroaryl group consisting of a 5-membered heteroaryl group optionally substituted in the carbon skeleton by a fluorine, chlorine or bromine atom or by a C1-3-alkyl or C1-3-alkoxy group, wherein the 5-membered heteroaryl group contains an oxygen or sulphur atom, and a phenyl ring fused to the abovementioned monocyclic heteroaryl groups via two adjacent carbon atoms, by means of which the bicyclic heteroaryl group is linked to the R1-substituted alkene-carbon atom and which may also be substituted in the carbon skeleton by a fluorine, chlorine or bromine atom or by a C1-3-alkyl or C1-3-alkoxy group, and B is a phenyl or naphthyl group which is substituted in each case by a carboxy group, by a group which may be converted into a carboxy group in viva or by a group which is negatively charged under physiological conditions, while the abovementioned phenyl group may additionally be substituted by a fluorine, chlorine, bromine or iodine atom, by a C1-3-alkyl, trifluoromethyl, phenyl, hydroxy, C1-3-alkyl-sulphonyloxy, phenylsulphonyloxy, carboxy, C1-3-alkoxycarbonyl, formyl, C1-3-alkylcarbonyl, C1-3-alkylsulphonyl, phenylsulphonyl nitro, pyrrolidino, piperidino, morpholino, Nâ€”(C1-3-alkyl)-piperazino, aminosulphonyl, C1-3-alkylaminosulphonyl- or di-(C1-3-aminosulphonyl group, by an n-C2-3-alkoxy group substituted in the 2 or 3 position by a di-(C1-3-alkyl)-amino group, by an amino group, by an Nâ€”(C1-3-alkyl)-amino or N, N-di-(C1-3-alkyl)-amino group wherein the alkyl moiety in the 2 or 3 position relative to the nitrogen atom may be substituted in each case by a C1-3-alkoxy group, by an N-phenylamino, N-(phenyl-C1-3-alkyl)-amino or N-(pyridyl-C1-3-alkyl)-amino group, by an aminocarbonyl group which may be mono- or disubstituted at the amino-nitrogen atom be a C1-3-alkyl group, by a pyrrolidinocarbonyl piperidinocarbonyl morpholinocarbonyl or Nâ€”(C1-3-alkyl)-piperazinocarbonyl group, by a sulphonyl group substituted by an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, pyrrolidino, piperidino, morpholino or Nâ€”(C1-3-alkyl)-piperazino group, by an amino or Nâ€”(C1-3-alkyl)-amino group which is substituted in each case at the amino-nitrogen atom by an aminocarbonyl, C1-3-alkylaminocarbonyl, phenyl-C1-3-alkylaminocarbonyl, phenylaminocarbonyl, pyridylaminocarbonyl, pyrrolidinocarbonyl, piperidinocarbonyl, morpholinocarbonyl or Nâ€”(C1-3-alkyl)-piperazinocarbonyl group, whilst in the abovementioned aminocarbonyl groups any hydrogen atom present may additionally be replaced by a C1-3-alkyl group, or by a 5- or 6-membered heteroaryl group, whilst the abovementioned phenyl groups may additionally be substituted by another fluorine, chlorine or bromine atom or by another C1-3-alkyl or C1-3-alkoxy group and two C1-3-alkoxy groups in the o position may be replaced by a methylenedioxy group, and the abovementioned 6-membered heteroaryl groups contain one, two or three nitrogen atoms and, unless stated otherwise, the abovementioned 5-membered heteroaryl groups contain an imino group optionally substituted by a C1-3-alkyl group, an oxygen or sulphur atom, or an imino group optionally substituted by a C1-3-alkyl group and an oxygen or sulphur atom or one or two nitrogen atoms, an isomer thereof or a salt thereof.