Gist-brocades N.v.

Cornelis A Bruynes

Theodorus K Jurriens

Johannes K Van Der Drift

Jan J De Koning

A novel process for the preparation of thioethers comprising reacting a silylated thiol of the formula

Preparation of thioethers

An improved process for the trimethylsilylation of organic compounds with at least one active hydrogen atom with hexamethyldisilazane, the improvement comprising effecting the reaction in the presence of 0.001 to 10 mole percent of a catalyst of the formula

Silylation process

A novel process for the preparation of 7-acylamino-3-(thio-substituted)-methyl-3-cephem-4-carboxylic acid 1-oxide derivatives comprising reacting a 7-acylamino-3-bromomethyl-3-cephem-4-carboxylic acid-1-oxide derivative with a silylated thiol of the formula

Preparation of 7-acylamino-3-(thio-substituted)-methyl

An improved process for the preparation of 3'-bromo-desacetoxycephalosphoranic acid sulfoxide compounds comprising protecting the 4-carboxy group of a 3'-unsubstituted cephalosporanic acid sulfoxide by silylating in an inert anhydrous organic solvent and brominating the silylated compound in situ which 3'-bromo compounds are valuable intermediates for the preparation of therapeutically useful cephalosporanic acid compounds.

Process for preparing 3'bromo-desacetoxycephalosporanic acid sulfoxide

Novel bromo-substituted deacetoxycephalosporins of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of benzamido, formamido, phenylacetamido and phenoxyacetamido, R.sub.2 is selected from the group consisting of hydrogen and bromine and R.sub.3 is a silyl group of the formula ##STR2## wherein R', R' and R'' are individually selected from the group consisting of alkyl of 1 to 6 carbon atoms, a halogen-substituted alkyl of 1 to 6 carbon atoms and aryl, which are suitable intermediates in processes for the preparation of antibiotics and their preparation.

Cephalosporin intermediates

An improved process for the preparation of 3-bromomethyl-3-cephem sulfoxide derivatives of the formula ##STR1## wherein R.sub.1 is an acylamido group and R.sub.2 is a group protecting the carboxy radical which are valuable intermediates for the preparation of various therapeutically useful cephalosporanic acid derivatives.

Preparation of 3-bromomethyl-3-cephem sulfoxides

Penicillanic acid derivatives of the formula ##STR1## wherein E is selected from the group consisting of hydrogen, a salt forming cation, and an ester forming residue which is known to improve the absorption characteristics of penicillanic compounds after oral administration to humans or animals, and Y is a group of the formula ##STR2## wherein Z.sub.1 and Z.sub.2 are individually selected from the group consisting of lower alkoxy, optionally substituted phenoxy, optionally substituted benzyl and benzyloxy group, optionally substituted lower alkyl, optionally substituted phenyl, hydroxy and -OM wherein M represents a salt forming cation, and hydrates of the said salts having antibacterial properties and their preparation and novel intermediates.

Novel penicillanic acid

Novel therapeutically useful and disinfecting penicillanic and cephalosporanic acid derivatives of the formula: ##SPC1## Wherein W represents a penicillanic or cephalosporanic acid residue or derivatives thereof and wherein Y represents a carbonamido group N-substituted by a phosphorous or sulfur containing residue or Y represents a phosphorous or sulfur containing substituent, and pharmaceutical and disinfecting compositions containing them and their use and process for the preparation of the said compounds.

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Koudekerk, Netherlands

Cornelis A Bruynes