Gist-brocades N.v.

Roussel Uclaf

Gist-brocades B.v.

Jagdish C Kapur

Herman P Fasel

Arthur F Marx

Peter W Henniger

Johannes K Van Der Drift

Willem J Van Zoest

Jacobus N Batist

Gerard J Van Veen

Penicillin glycolate

New 9-alpha-hydroxy steroids are prepared by the introduction of substituents on the D-ring of 9-alpha-hydroxy-androst-4-ene-3,17-dione. The resulting compounds are useful intermediates in the synthesis of corticosteroids.

9-alpha-hydroxy steroids, process for their preparation, process for the

In a process for the preparation of 6,6-dibromo-penicillanic acid-1,1-dioxide comprising reacting 6.beta.-amino-penicillanic acid-1,1-dioxide with a nitrosating agent in the presence of bromine and an inorganic acid or strong organic acid, the improvement comprising effecting the reaction in the presence of an alcohol resulting in a high purity product.

Preparation of 6,6-dibromo-penicillanic acid-1,1-dioxide

A novel process for the preparation of high purity penicillanic acid-1,1-dioxide comprising subjecting 6,6-dibromo-penicillanic acid-1,1-dioxide to dehalogenation with magnesium in association with an acid in high yields.

Dehalogenation process of a penicillanic acid derivative

A process for the preparation of penicillanic acid-1,1-dioxides of the formula ##STR1## wherein X is selected from the group consisting of hydrogen and substituent such as halogen or acetoxy and R is selected from the group consisting of hydrogen, a pharmaceutically acceptable metal ion and/or ester radical comprising debrominating a 6-.alpha.-bromo- and/or 6,6-dibromo-penicillanic 1,1-dioxide selected from the group consisting of the formula ##STR2## wherein X and R have the above definition in an aqueous containing medium with zinc in association with an acid having a pK.sub.a -value measured in water less than 3.5 and optionally if R is H converting the acid into a pharmaceutically acceptable salt or ester.

Process for the preparation of penicillanic acid 1,1-dioxides

A process for the preparation of [D-.alpha.-amino-p-hydroxyphenylacetamido]-penicillanic acid or cephalosporanic acid compounds comprising reacting a compound having a formula selected from the group consisting of ##STR1## wherein X is selected from the group consisting of hydrogen, acetoxy and five-membered heterocyclic group containing at least one hetero atom of the group consisting of oxygen, sulfur and nitrogen and optionally substituted with e.g. lower alkyl, this residue being attached to the 3-CH.sub.2 group via sulfur atom and wherein a NH radical if present has optionally been silylated with at least one mole equivalent of a silylating agent producing ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of lower alkyl, benzyl, cycloalkyl and phenyl in an inert anhydrous, organic solvent, preferably a water-inmiscible organic main-solvent, to form a compound having a formula selected from the group consisting of ##STR3## adjusting the pH to a scale value of 5.5 to 7.5 and reacting the resulting compounds in a pre-cooled solution with an at least equimolar amount of a compound of the formula wherein R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.6 and R.sub.7 are lower alkoxy.

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Delft, Netherlands

Jagdish C Kapur