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filingDate 1981-12-23^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 1982-07-21^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-0056144-A1
titleOfInvention Carboxylic acid derivatives, their preparation and use as pharmaceuticals
abstract m die Zahl 0 oder 1, n die Zahl 1 oder 2, R ein Wasserstoffatom oder eine Alkylgruppe mit 1 bis 3 Kohlenstoffatomen, R, ein Wasserstoff-, Fluor-, Chlor-, Brom- oder Jodatom, eine Alkyl- oder Alkoxygruppe mit jeweils 1 bis 4 Kohlenstoffatomen, eine Cyano-, Hydroxy- oder Trifluormethylgruppe oder eine gegebenenfalls durch eine Alkylgruppe mit 1 bis 3 Kohlenstoffatomen, ein Fluor-, Chlor-oder Bromatom substituierte Phenylgruppe, R 2 und R 3 zusammen mit dem dazwischen liegenden Stickstoffatom eine Piperidino-, 3,5-Dimethyl-piperidino-, Octahydro-1H-azonino-, Decahydro-azecino-, 1,3-Dihydro-isoindolo-, Hexahydro-isoindolo- oder Octahydro-isoindologruppe, eine durch eine Alkylgruppe mit 5 bis 10 Kohlenstoffatomen substituierte Piperidinogruppe, eine Azabicycloalkylgruppe mit 7 bis 12 Kohlenstoffatomen im Bicycloalkanring, der durch eine oder mehrere Alkylgruppen mit jeweils 1 bis 3 Kohlenstoffatomen substituiert sein kann, oder eine durch ein Halogenatom, eine Alkoxygruppe mit 1 bis 3 Kohlenstoffatomen oder eine Aminogruppe substituierte 1,3-Dihydro-isoindolgruppe oder auch, wenn m die Zahl 1 darstellt, die Pyrrolidino-, Hexamethylenimino- oder Heptamethyleniminogruppe, X eine CH-Gruppe oder ein Stickstoffatom, R, ein Wasserstoffatom, eine Alkylgruppe mit 1 bis 3 Kohlenstoffatomen oder eine Arylgruppe und Z eine gegebenenfalls veresterte Carboxygruppe bedeuten, deren optisch aktive Antipoden, sofern sie ein asymmetrisches Kohlenstoffatom enthalten, und deren Salze, insbesondere deren physiologisch verträgliche Säureadditionssalze mit anorganischen oder organischen Säuren oder Basen. Außerdem sind 2-Amino-carbonsäure-Derivate beschrieben, die wertvolle Zwischenprodukte zur Herstellung der Verbindungen der allgemeinen Formel 1 darstellen. Carboxylic acid derivatives of the general formula in the m is the number 0 or 1, n is the number 1 or 2, R is a hydrogen atom or an alkyl group with 1 to 3 carbon atoms, R, a hydrogen, fluorine, chlorine, bromine or iodine atom, an alkyl or alkoxy group each having 1 to 4 carbon atoms, a cyano, hydroxyl or trifluoromethyl group or, if appropriate, an alkyl group having 1 to 3 carbon atoms Fluorine, chlorine or bromine atom-substituted phenyl group, R 2 and R 3 together with the nitrogen atom in between are piperidino, 3,5-dimethyl-piperidino, octahydro-1H-azonino, decahydro-azecino, 1,3-dihydro-isoindolo, hexahydro-isoindolo or Octahydro-isoindo group, a piperidino group substituted by an alkyl group having 5 to 10 carbon atoms, an azabicycloalkyl group having 7 to 12 carbon atoms in the bicycloalkane ring, which may be substituted by one or more alkyl groups each having 1 to 3 carbon atoms, or one by a halogen atom, an alkoxy group 1,3-dihydro-isoindole group substituted with 1 to 3 carbon atoms or an amino group or, if m represents the number 1, the pyrrolidino, hexamethyleneimino or heptamethyleneimino group, X is a CH group or a nitrogen atom, R, a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an aryl group and Z represents an optionally esterified carboxy group, its optically active antipodes, provided that they contain an asymmetric carbon atom, and their salts, in particular their physiologically tolerable acid addition salts with inorganic or organic acids or bases. In addition, 2-amino-carboxylic acid derivatives are described, which are valuable intermediates for the preparation of the compounds of general formula 1. n n n The compounds can be prepared by methods customary for analog compounds.
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