Oxime derivatives of 3-alkyloxy- or 3-alkylthiomethyl 7-amino-thiazolylacetamido cephalosporanic acid, their preparation, their use as medicaments and compositions containing them

Abstract

Abstract 1. Claims for the Contracting States : BE, CH, DE, GB, IT, LI, LU, NL, SE The products with the general formula (I') : see diagramm : EP0034536,P52,F1 syn isomers in which A represents a hydrogen atom, an equivalent of an alkali or alkaline earth metal, magnesium, ammonium or aminated organic base, or A represents the residue of an easily cleavable ester group, R'a represents an alkyl radical, possibly interrupted by a hetero-atom, an alkenyl or alkynyl radical, with at most 6 carbon atoms, linear or branched or a benzyl or phenylethyl radical, possibly substituted by a carboxy, amino, aminoalkyl, alkylamino, dialkylamino, or dialkylaminoalkyl radical, n is 0, 1 or 2, X' represents a sulphur atom, possibly oxidized in the form of sulphoxide or sulphone, or an oxygen atom, as well as the salts of the products with the formula (I') with mineral or organic acids. 1. Claims for the Contracting State : AT Process for preparing the products with the general formula (I') see diagramm : EP0034536,P56,F1 syn isomers in which A represents a hydrogen atom, an equivalent of an alkali or alkaline earth metal, magnesium, ammonium or aminated organic base, or A represents the residue of an easily cleavable ester group, R'a represents an alkyl radical possibly interrupted by a hetero-atom, an alkenyl or alkynyl radical with at most 6 carbon atoms, linear or branched, or a benzyl or phenylethyl radical, possibly substituted by a carboxy, amino, aminoalkyl, alkylamino, dialkylamino, dialkylaminoalkyl radical, n is 0, 1 or 2, X' represents a sulphur atom, possibly oxidized in the form of sulphoxide or sulphone, or an oxygen atom, as well as the salts of the products with the formula (I') with mineral or organic acids, characterized in that a product with the formula (II) : see diagramm : EP0034536,P56,F2 in which n, X' and R'a have the significance previously indicated and A' represents a hydrogen atom or the residue of an easily eliminated ester group, is treated with a product with the formula (III) : see diagramm : EP0034536,P56,F3 or a functional derivative of this acid, in which formula (III) R1 represents a hydrogen atom or a protective group of the amino radical, R' represents a hydrogen atom or a protective group of the hydroxyl radical, so as to obtain a product with the formula (IV) : see diagramm : EP0034536,P57,F1 in which R1 , R', A', R'a, X' and n have the preceding significance, which product, if desired, when n is O and X' represents a sulphur or oxygen atom, is treated with an oxidation agent, so as to obtain a product with the formula (IV) in which n is 1 or 2 and X' represents an oxidized sulphur atom in the form of sulphoxide or sulphone or an oxygen atom, which product with the formula (IV) is submitted, if necessary or if desired, to one or more of the following reactions, in any order : a) cleavage by hydrolysis, hydrogenolysis or by action of thiourea of the ester group or the protective groups of the amino radical(s), b) esterification or salification of the carboxyl radical(s) by a base, c) salification of the amino radical(s) by an acid.

Inventors

• 👤 René Heymes
• 👤 Didier Pronine

Bibliographic Details