Verfahren zur Herstellung von neuen N-substituierten 4-Phenyl-piperidin-4-carbon-saeureaethylesterabkoemmlingen

• Main Authors: DENSS ROLF, MEISELS ALEX, RYF HUGO
• Format: Patent
• Language: German
• Published: 09.03.1967
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

The invention comprises compounds of the formula: <FORM:0949732/C2/1> (wherein R1 is hydrogen or alkyl of at most 3 carbon atoms; R2 is hydrogen, cycloalkyl, cycloalkyl-alkyl, aryl, aralkyl, heterocyclic or heterocyclic-alkyl which may be substituted by alkyl or alkoxy groups of at most 4 carbon atoms or by dialkylamino groups the alkyl portions of which each contain at most 4 carbon atoms or, in rings of aromatic character, by halogen atoms or nitro carbethoxy or acetylamino groups; R3 is hydrogen or alkyl or alkenyl of at most 4 carbon atoms, or the alkyl radical R3 can be bound to an alkyl radical R2 direct or by way of an oxygen atom, an imino group or an alkylimino group of at most 4 carbon atoms) and their salts; and their preparation by reacting 4-phenyl-4-carbethoxy-piperidine with a reactive ester of the appropriate hydroxy-alkane carboxylic acid amide, or by reacting the amine NHR2R3 with the appropriate carboxylic acid or a reactive functional derivative thereof, or, when R1 and R2 are hydrogen, by saponifying the corresponding nitrile. Examples are given. 1 - Cyanomethyl -4- phenyl -4- carbethoxypiperidine is prepared from 4-phenyl -4- carbethoxy - piperidine, formaldehyde and potassium cyanide 1-carboxymethyl -4- phenyl -4- carbethoxy piperidine is prepared from 4-phenyl -4- carbethoxy-piperidine and chloroacetic acid. This last-named process is also referred to in more general terms for other corresponding carboxyalkyl compounds, which, with inorganic acid halides, give 1-halocarbonylalkyl -4- phenyl -4- carbethoxy-piperidines. The piperidine derivatives of the invention, which are stated to have central depressing, antitussive, analgesic and spasmolytic activity, may be made up into pharmaceutical compositions with suitable carriers. Aqueous solutions of the salts with organic and inorganic acids are referred to.