Bayer Aktiengesellschaft

Michael Preiss

Karl G Metzger

Hans-Bodo Konig

Michael Walkowiak

Wilfried Schrock

Peter Feyen

Wolfgang Krohn

Paul Naab

Arthur Haaf

Gunter Schmidt

Horst Behre

Wolfgang Gau

Rudolf Zerbes

Hermann Schutt

Wolfgang Koebernick

Werner Teller

Ulrich Schorsch

The invention relates to a continuous process for the preparation of enantiomerically pure biarylketocarboxylic acids, S-phenylethylamine being employed as an auxiliary base in the resolution. Biarylketocarboxylic acids, in particular substituted biaryl-4-ketocarboxylic acids, are inhibitors of enzymes of the matrix metalloproteinases class. By inhibition of the abovementioned enzymes, it is possible, for example, to control osteoarthritis, rheumatoid arthritis and metastases.

Production of enantiomer-free biarylketocarboxylic acids

##STR1## is reacted with an amine ##STR2## to give the compound of the formula ##STR3## Because the starting material (I) has F in 7-position rather than Cl, the reaction proceeds at relatively low temperature with minimum side reactions.

Preparation of quinolinecarboxylic acids

A process for the preparation of quinolone-carboxylic acid esters of the formulae I and II ##STR1## in which A represents nitrogen or .dbd.C--R.sup.4,

Process for the preparation of quinolonecarboxylic acid esters

Known quinolone carboxylic acid derivatives of the formula ##STR1## are treated so as to become readily administrable parenterally, the treatment comprising dissolving the active compound using an acid, allowing the solution to stand for about 0.15 to 150 hours at a temperature from room temperature to the boiling point of the solution, filtering the solution, precipitating the active compound from the solution using a basic reagent, and converting the precipitated active compound into a form which can be administered parenterally.

Process for the preparation of quinolonecarboxylic acids which can be

A process for the preparation of a benzylidene compound of the formula ##STR1## in which R.sup.1 is hydrogen or one or two substituents independently selected from the group consisting of nitro, cyano, halogen, SO.sub.3 H, alkyl, alkoxy and fluorinated alkyl, each with 1 to 4 C atoms and two or three fluorine substituents, and

Preparation of benzylidene compounds

In the preparation of a 1,4-dihydropyridine of the formula ##STR1## in which R is a phenyl radical which is optionally substituted once or twice by nitro and/or chlorine,

Process for the preparation of 1,4-dihydropyridinedicarboxylic esters

A process for the preparation of o-nitrobenzaldehyde, comprising converting to the corresponding acetals a mixture of nitrated benzaldehyde which contains about 10 to 30% of o-nitrobenzaldehyde and about 70 to 90% of m-nitrobenzaldehyde, removing the o-nitrobenzaldehyde acetal by distillation, and then converting the o-nitrobenzaldehyde acetal to o-nitrobenzaldehyde.

Preparation of o-nitrobenzaldehyde

The invention relates to optically pure heterocyclic amino acid compounds of the Formula I, as described hereinabove as well as a process for their preparation involving subject D, L-compounds to the action of a proteolytic enzyme. The compounds obtained are useful, inter alia, as intermediates for the manufacture of cephalosporins or penicillins.

Optically pure heterocyclic aminoacid compounds, a process for their use

.beta.-Lactam compounds of the formula ##STR1## in which B denotes an optionally substituted heterocyclic 5-membered or 6-membered ring or an optionally substituted phenyl ring,

.beta.-Lactam antibiotics and their medicinal use

2-Hetero-acetamido-penicillanates and cephalosporinates of the formula ##STR1## in which R is hydrogen or lower alkoxy,

2-Hetero-acetamido-cephalosporinates

New .beta.-lactam antibiotics carrying a terminal -ylidene-2-pyrrolidinon-1-yl radical and of the formula ##STR1## in which A and A' represent hydrogen, optionally substituted alkyl, aryl or a group of the formula R.sub.1 --X' in which

Antibacterial and growth promoting .beta.-lactam antibiotics carrying an

Antibacterially active and animal feedstuff supplement .beta.-lactam antibiotics of the formula ##STR1## in which R is H or --UR',

.beta.-Lactam antibiotics

New penicillin derivatives, or esters or salts thereof, of the formula ##STR1## in which R is H or alkoxy,

Penicillin derivatives

New .beta.-lactam antibiotics of the formula ##STR1## in which A is hydrogen or methoxy,

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Wuppertal, Germany

Michael Preiss