Merck Patent Gesellschaft MIT Beschrankter Haftung

Walter Hameister

Helmut Wahlig

Rolf Bergmann

Werner Rogalski

Rolf Gericke

Rudolf Gottschlich

Richard Kirchlechner

Juergen Seubert

Novel pyridone-acetic acid derivative, viz. 3,5-dichloro-4-pyridone-1-acetic acid (I) is used as an intermediate in the production of certain cephem derivatives having anti-bacterial activity against gram-negative and gram-positive bacteria. The acid (I) is prepared by methods generally known in the art, e.g. by reacting 3,5-dichloro-4-pyridone with chloracetic acid or bromoacetic acid.

Pyridone-acetic acid derivative

Cephem derivatives of the formula ##STR1## wherein Z is 1,4-dihydro-4-oxo-1-pyridyl or the corresponding group substituted by one or more of alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, OH, F, Cl, Br, I, NO.sub.2 and NH.sub.2 ; and R is H, --OCOCH.sub.3 or -S-Het, wherein Het is 3-methyl-1,2,4-thiadiazolyl-5, 5-methyl-1,3,4-oxadiazolyl-2, 5-hydroxymethyl-1,3,4-oxadiazolyl-2, 5-methyl-1,3,4-thiadiazolyl-2, 5-hydroxymethyl-1,3,4-thiadiazolyl-2, tetrazolyl-5, 1-methyltetrazolyl-5, 1,2,3-triazolyl-4, 4-methyl-oxazolyl-2 or 1-oxidopyridinio-2, and the readily cleavable esters thereof and the physiologically acceptable salts thereof, possess anti-bacterial activity and can be prepared by reacting a 3-CH.sub.2 R-7-amino-3-cephem-4-carboxylic acid or a functional derivative thereof with a pyridone acetic acid of the formula Z-CH.sub.2 -COOH or a functional derivative thereof.

1,4-Dihydro-4-oxo-pyridylacetamido cephalosporins and their utilization

7-Methoxy-6-thiatetracyclines of the formula ##SPC1## Wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each are H or alkyl of 1 to 4 carbon atoms, and the physiologically acceptable acid addition salts thereof.

7-Methoxy-6-thiatetracyclines and their preparation

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Walter Hameister