Boehringer Mannheim Gmbh

Felix Helmut Schmidt

Ruth Heerdt

Manfred Hubner

Elmar Bosies

Kurt Stach

Wolfgang Kampe

Kurt Stach, Deceased

Werner Rothe

Hans Kuhnle

Helmut Heinemann

Hans-Frieder Kuhnle

Harald Stork

Gunter Betzien

Max Thiel

Manfred Kuhr

Hans P Wolff

Erich Fauland

Rainer Haeckel

Michael Oellerich

Klaus Koch

Manfred Hubner, Deceased

Vladimir Hrstka

Walter Aumuller

Helmut Weber

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

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,

Hypoglycaemically and hypolipidaemically active derivatives of

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

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

Indole-carboxylic acid compounds of the formula: ##STR1## wherein R.sub.1 is lower alkyl or alkoxy radical or halogen;

Indole-carboxylic carbon compounds and pharmaceutical compositions

A blood sugar lowering composition comprising as the active material particulate glibenclamide having a surface area of about 3 to 10 m.sup.2 /g in admixture with a pharmacologically acceptable non-ionic wetting agent present in about 2 to 20 times the weight of the glibenclamide. The preferred wetting agent is polyoxyethylene stearate present in about 5 to 10 times the weight of the glibenclamide.

Rapidly resorbable glibenclamide

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.

2-Hydroxymethyl indole compounds and blood sugar lowering compositions

New heterocyclic-substituted nebularin compounds of the formula: ##SPC1## Wherein

Heterocyclic-substituted nebularin compounds

Rapidly resorbable particulate glibenclamide having a particle surface area of active material of at least 3 m.sup.2 /g is produced by precipitating the active material from its solution in an organic solvent or in water or aqueous alcohol, preferably rendered alkaline, using water which is preferably acidified.

Preparation of rapidly resorbable glibenclamide

New N(6)-disubstituted adenosine compound of the formula ##SPC1## Wherein

Growing community of inventors

Mannheim-Seckenheim, Germany

Felix Helmut Schmidt