Boehringer Mannheim Gmbh

Ruth Heerdt

Felix Helmut Schmidt

Manfred Hubner

Hans Kuhnle

Elmar Bosies

Kurt Stach

Rudi Weyer

Ernst-Christian Witte

Volker Hitzel

Kurt Stach, Deceased

Hans P Wolff

Hans-Frieder Kuhnle

Michael Oellerich

Rainer Haeckel

Max Thiel

Wolfgang Schaumann

Rudi Gall

Uwe Bicker

Fritz Kaiser

Anna E Ziegler

Helmut Weber

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

2-Substituted-1-aziridine-carboxylic acid esters exhibiting immuno-stimulant activity and of the formula ##STR1## wherein X is a carbamoyl or alkoxycarbonyl radical, and

1-Aziridine carboxylic acid derivatives with immunostimulant activity

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

Phenyl-alkane-carboxylic acids of the formula ##STR1## wherein A is an aryl, aralkyl or arylvinyl radical optionally substituted by hydroxy, halogen, trifluoromethyl, alkyl, alkylthio, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino, aryloxy or alkoxy-substituted aryloxy, or is an aryloxyalkyl or arylthioalkyl radical, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy,

A 2-hydrazonopropionic acid derivative of the formula ##STR1## wherein R is an aliphatic hydrocarbon radical, and

Hypoglycaemically active 2-alkyl- or -alkenyl-hydrazono propionic acid

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

Hypoglycemically and hypolipidemically active derivatives of

New indole-2-carbaldehyde compounds of the formula ##STR1## wherein R.sub.1 is lower alkyl

Indole-2-carbaldehyde compounds and blood sugar reducing compositions

New biguanide compounds of the formula: ##STR1## wherein A is saturated or unsaturated cycloaliphatic hydrocarbyl, and the physiologically compatible salts thereof; display outstanding anti-diabetic effectiveness in the treatment of diabetes mellitus, without showing the typical side effects of biguanide treatment, viz., lactacidosis.

Biguanide compounds and anti-diabetic compositions

New indole derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are hydrogen or halogen or lower alkyl or, taken together, represent a --CH=CH-CH=CH- bridge, with the proviso that R.sub.1 and R.sub.2 are not both hydrogen, and wherein, when R.sub.2 is halogen or alkyl, R.sub.1 can also be alkoxy; Are outstandingly effective in blood sugar lowering action in mammals.

Growing community of inventors

Mannheim-Feudenheim, Germany

Ruth Heerdt