Boehringer Mannheim Gmbh

Hans Kuhnle

Ruth Heerdt

Manfred Hubner

Rudi Weyer

Ernst-Christian Witte

Volker Hitzel

Felix Helmut Schmidt

Hans P Wolff

Elmar Bosies

Wolfgang Schaumann

Fritz Kaiser

Rainer Haeckel

Michael Oellerich

Manfred Hubner, Deceased

The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.1 is not a methyl or benzyl radical; and the physiologically acceptable salts, carboxylic acid esters and amides thereof. The invention also provides processes for the preparation of these compounds pharmaceutical compositions containing them, and their use in combating hypoglycaemia.

Pharmacologically active novel O-substituted pyruvic acid oximes

A pyruvic acid hydrazone derivative of the formula: ##STR1## wherein R is an aryl radical optionally substituted by lower alkyl or is an aliphatic hydrocarbon radical which can be substituted by a lower alkoxy, a cycloalkyl or an optionally substituted aryl radical,

N-Substituted pyruvic acid hydrazones, preparation thereof and

Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy,

Hypoglycaemically and hypolipidaemically active derivatives of

A 2-hydrazono-propionic acid derivative of the formula ##STR1## wherein R.sub.1 and R.sub.2, each independently is hydrogen, halogen, trifluoromethyl, alkyl, hydroxyl, acyloxy or alkoxy or together are methylenedioxy, and

Hypoglycaemically active 2-(phenylalkyl- or -alkenyl

An N-substituted carboxylic acid amide of the formula ##STR1## wherein A is a valency bond or an oxygen or sulphur atom or a methylene, ethylene, vinylene, ethyleneoxa or ethylenethia radical,

Hypoglycaemically and hypolipidaemically effective n-substituted

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Mannheim-Neuostheim, Germany

Hans Kuhnle