Alpha-amino-acides, compositions et procédé pour la préparation de ces composés

Alpha-Aminosäuren, Präparate und Verfahren zur Herstellung dieser Verbindungen

Alpha-amino acids, compositions and process for preparing said compounds

Abstract

a-Amino Acids, compositions and process for preparing said compounds a-ethynyl- and - a-vinyl- 3,4- disubstituted pheynylalanines and esters thereof, have been prepared by reaction of methyl 3,4-dihydroxybenzoate with diphenyldichloromethane, reduction of the so obtained methyl 3,4-diphenylmethylene- dioxy- benzoate to 3,4-diphenylmethylenedioxybenzyl- alcohol, and transforming this to the benzylchloride. This 3,4-diphenylmethylenedioxybenzylchloride reacts with 1-trimethyl- silyl-N- benzylidene-3-aminoprop-1-yneto form 3-(3,4- diphenylmethylenedioxybenzyl) -1-trimethysilyl N-benzylidene-3- aminoprop-1-yne. With methyl chloroformate this compound gives 3-carbomethoxy-3- (3,4- diphenylmethylenedioxybenzyl-1-trimethylsilyl -N-benzylidene -3-aminoprop-1-yne. The benzylidene-group, the trimethylsilyl-group and the diphenyl-methylene- group are removed, which results in the formation of a-ethynyl- 3,4-dihydroxy- phenylalanine. The a-vinyl- analog is obtained by hydrogenation of an intermediate. The compounds have a pharmaceutical activity.

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Patent Citations (2)

    Publication numberPublication dateAssigneeTitle
    FR-1850-MDecember 31, 1969Merck & Co IncDérivés de la phénylalanine.
    US-3132176-AMay 05, 1964Merck & Co IncPreparation of o, o-dialkanoyl derivatives of d, l-alpha-alkyl-beta-3, 4-dihydroxyphenylalanine by preferential acylation

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Cited By (11)

    Publication numberPublication dateAssigneeTitle
    DE-2827805-A1January 18, 1979Merrell Toraude & CoAlpha-vinyl-aminosaeuren und verfahren zu ihrer herstellung
    DE-2827824-A1January 18, 1979Merrell Toraude & CoAlpha-acetylenische aminosaeuren
    DE-2827866-A1January 18, 1979Merrell Toraude & CoAlpha-acetylenische derivate von alpha-aminosaeuren sowie verfahren zu deren herstellung
    EP-0007615-A2February 06, 1980Merck & Co., Inc.Verfahren zur Herstellung von Aminosäuren und Estern
    EP-0007615-A3May 28, 1980Merck & Co. Inc.Process for preparing amino acids and esters, and intermediates therefor
    EP-0008657-A1March 19, 1980Merck & Co., Inc.Alpha-vinyl-alpha-aminoacids and their esters and pharmaceutical compositions containing them
    EP-0008658-A1March 19, 1980Merck & Co., Inc.Alpha-éthinyle-alpha-amino-acides et leurs esters et compositions pharmaceutiques les contenant
    EP-0309827-A1April 05, 1989Banyu Pharmaceutical Co., Ltd.Dérivés de L-dopa ou leurs sels d'addition, procédé pour les produire et leur utilisation
    FR-2401133-A1March 23, 1979Merrell Toraude & CoNouveaux derives d'aminoacides a-acetyleniques, leur preparation et leur utilisation comme inhibiteurs de la decarboxylase des aminoacides aromatiques
    FR-2724654-A1March 22, 1996Roussel UclafNouveaux derives de l'acide gallique, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant
    WO-9608483-A1March 21, 1996Roussel UclafGallic acid derivatives, method for their preparation and their use as drugs