Hoechst Aktiengesellschaft

Theodor Wollmann

Rudolf Lattrell

Gerd Fischer

Elisabeth Defossa

Uwe Gerlach

Ulrich Stache

Dieter Isert

Norbert Krass

Rolf Horlein

Joachim-Heiner Jendralla

Rolf H Orlein

Adolf Heinz Linkies

Peter Hammann

Holger Wallmeier

Wolfgang Martin

Elisabeth Defobetaa

Rolf Hoerlein

The invention relates to a process which comprises a compound of the formula II ##STR1##

Process for the preparation of cephem prodrug esters

Lipopeptide derivatives of the formula I ##STR1## with R.sup.1 equal to OH or NH.sub.2 and R.sup.2 a C.sub.8 -C.sub.22 -acyl radical, pharmaceutical products which are effective for bacterial infections and contain such lipopeptide derivatives, process for preparing the lipopeptide derivatives and the pharmaceutical products, and the use of the lipopeptide derivatives for controlling bacterial infections are described.

Lipopeptide derivatives, a process for their preparation and their use

Enterally absorbable diastereomers of 1-(isopropoxycarbonyloxy)ethyl (6R, 7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-(methoxyme thyl)-3-cephem-4-carboxylate of the formula I ##STR1## and their physiologically acceptable salts and also diastereomerically pure salts of the compounds of the formula II ##STR2## where HX is a mono- or polybasic acid and where X is an inorganic or organic physiologically acceptable anion, and a process for the preparation of these compounds of the formula I or II, which comprises first precipitating the more sparingly soluble diastereomer of the formula IV in the mixing together of 1 equivalent of a solution of the diastereomer mixture of the formula III with 0.2-2 equivalents of a solution of the acid component HY and separating it off by filtration, then precipitating the more readily soluble diastereomer of the formula IV from the filtration solution, it being possible for the acid component HY to be identical or different in the consecutive steps.

Diastereomers of 1-(isopropoxycarbonyloxy)ethyl 3-cephem-4-carboxylate

Crystalline acid addition salts of diastereomerically pure 1-(2,2-dimethylpropionyloxy)ethyl 3-cephem-4-carboxylate The invention relates to crystalline acid addition salt of the two diastereomers of the 1-(2,2-dimethylpropionyloxy)ethyl 3-cephem-4-carboxylate of the general formula II ##STR1## in which X is the anion of a physiologically acceptable, mono- or polybasic, inorganic or organic acid and the group =N--OH is in the syn-position, pharmaceutical formulations which are active against bacterial infections and contain such cephem derivatives, processes for the preparation of the cephem derivatives and the use of the cephem derivatives for combating bacterial infections.

Crystalline acid addition salts of diastereomerically pure

The invention relates to a process for the preparation of cephem prodrug esters of the formula: ##STR1## in which R.sup.1 is C.sub.1 -C.sub.5 -alkanoyloxy-C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.5 -alkoxycarbonyloxy-C.sub.1 -C.sub.3 -alkyl and X is an inorganic or organic anion, and in which the hydroxyimino group is present in the syn-form.

The invention relates to crystalline acid addition salt of the two diastereomers of the 1-(2,2-dimethylpropionyloxy)ethyl 3-cephem-4-carboxylate of the general formula II ##STR1## in which X is the anion of a physiologically acceptable, mono- or polybasic, inorganic or organic acid and the group .dbd.N--OH is in the syn-position, pharmaceutical formulations which are active against bacterial infections and contain such cephem derivatives, processes for the preparation of the cephem derivatives and the use of the cephem derivatives for combating bacterial infections.

Enterally absorbable diastereomers of 1-(isopropoxycarbonyloxy)ethyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-(metho xymethyl)-3-cephem-4-carboxylate of the formula I ##STR1## and their physiologically acceptable salts and also diastereomerically pure salts of the compounds of the formula II ##STR2## where HX is a mono- or polybasic acid and where X is an inorganic or organic physiologically acceptable anion, and a process for the preparation of these compounds of the formula I or II, which comprises first precipitating the more sparingly soluble diastereomer of the formula IV in the mixing together of 1 equivalent of a solution of the diastereomer mixture of the formula III with 0.2-2 equivalents of a solution of the acid component HY and separating it off by filtration, then precipitating the more readily soluble diastereomer of the formula IV from the filtration solution, it being possible for the acid component HY to be identical or different in the consecutive partial steps and any desired sequence of addition of different acid components HY being possible, and optionally further purifying the obtained salts by crystallization, are described.

Diastereomers of 1-(isopropoxycarbonyloxy) ethyl 3-cephem 4-carboxylate

The present invention relates to a process for the preparation of 7-amino-3-methoxymethylceph-3-em-4-carboxylic acid (I) from 7-amino-3-methoxymethylceph-3-em-4-carboxylic acid esters (II) or their salts by ester cleavage. The process comprises treating the compound II with formic acid, trifluoroacetic acid, methanesulfonic acid or trifluoromethanesulfonic acid or a mixture of two of these acids in each case.

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Hofheim am Taunus, Germany

Theodor Wollmann