Hoffmann-la Roche Inc.

Basilea Pharmaceutica Ag

Reuter Chemischer Apparatebau Kg

Basilea Pharmaceutica Ag, a Swiss Company

Glaxo Group Limited

Milan Soukup

Teodor Lukac

Erich Widmer

Karl Reuter

Marc Muller

Florian Stolz

Viktor Meier

Mark Kantor

Jofzsef Balint

Paul Spurr

Claude Stritt

Rolf Thomessen

Mario Mazzuchelli

The invention relates to a process for preparing chiral octenoic acid derivatives, which constitute important intermediates in the preparation of medicament active ingredients, and also to novel intermediates which are used in the process for preparing the octenoic acid derivatives mentioned.

Process for preparing octenoic acid derivatives

Process for preparing chiral octenoic acid derivatives

Novel halophenyl derivatives of the general formula (I), wherein Ris halogen, a leaving group or 1H-1,2,4-triazol-1-yl and Ris ethynyl or carboxy, Xis halogen and Xand Xare each independently hydrogen or halogen, and their manufacture are described. They are intermediates for manufacturing azole derivatives of the general formula (V) which are valuable medicaments useful for treating systemic mycoses.

Intermediate halophenyl derivatives and their use in a process for preparing azole derivatives

The invention is concerned with a process for the manufacture of vinylpyrrolidinone-cephalosporin derivatives from 3-amino-pyrrolidine derivatives of the formula wherein

Process for the manufacture of 3-amino-pyrrolidine derivatives

A process for the production of 9-(Z)-retinoic acid is described which comprises reacting an alkali metal salt of 3-methyl-4-oxocrotonic acid with a C-triphenyl-phosphonium salt. 9-(Z)-retinoic acid is used in the treatment of dermatological diseases.

Process for the production of 9-(Z)-retinoic acid

The invention is concerned with a process for the manufacture of 3-amino-pyrrolidine derivatives of the formulawherein

The present invention is directed to a process, and novel intermediates used in the manufacture of, dicarboxamides of the formula I ##STR1## wherein A, G, L, Q, X and Y have the meaning given in the specification, starting from corresponding N-substituted aspartic acid and from corresponding amines G-NHCH(X,Y), via corresponding N-substituted oxazolidinone and N,N-substituted aspartates.

Intermediates for the manufacture of dicarboxamides having thrombin

Process for the manufacture of dicarboxamides

A process for the manufacture of compounds of the general formula ##STR1## wherein R.sup.1 signifies hydroxy or an etherified hydroxy group, and of zeaxanthin by converting a compound of the general formula ##STR2## wherein R.sup.1 has the above significance, in an inert organic solvent into the acetylenide and reacting this with methyl vinyl ketone, reducing the alcoholate obtained or the alcohol (obtained after hydrolysis of the alcoholate) of the general formula ##STR3## wherein R.sup.1 has the above significance, in an inert organic solvent with an aluminum hydride of the general formula

Ethynylcyclohexene compounds and processes for manufacture thereof

A process for the manufacture of certain cycloalkenylalkenes, e.g. vitamin A acetate, comprises dehydrating 1-(5-acetoxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclo hexanol or 4 aetoxy-1-(5-acetoxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohexano l or 1-(9-acetoxy-3,7-dimethyl-4-hydroxy-nona-2,5,7-trienyl)-2,6,6-trimethyl- cyclohexene in the presence of an alkali metal bromide or of manganese bromide or of a hydrate of such a bromide as the catalyst and in an organic solvent. The products are especially suitable as intermediates in carotinoid syntheses.

Process for producing cycloalkenylalkenes

A process for the manufacture of compounds of the general formula ##STR1## wherein R.sup.1 signifies hydroxy or an etherified hydroxy group, and of zeaxanthin by converting a compound of the general formula ##STR2## wherein R.sup.1 has the above significance, in an inert organic solvent into the acetylenide and reacting this with methyl vinyl ketone, reducing the alcoholate obtained or the alcohol (obtained after hydrolysis of the alcoholate) of the general formula ##STR3## wherein R.sup.1 has the above significance, and subsequently hydrolyzing to give the compound of formula IV and, if desired, converting the compound of formula IV obtained into zeaxanthin.

Ethynylcyclohexene compounds

A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.

Process for carotenoid intermediates

Compounds of the formula ##STR1## wherein n is either 0 or 1; R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen, hydroxy, oxo group, a protected hydroxy or protected oxo group; R.sup.3 is hydroxy oxo group, .dbd.CH--CH.sub.2 --OH, .dbd.CH--CHO or one of the foregoing groups where the hydroxy or oxo functions are protected; R.sup.4 is --CO--OR.sup.6, --CO--R.sup.6, --CO--NR.sup.6 R.sup.7, --CO--Cl or --SO.sub.2 --R.sup.6 ; R.sup.6 is saturated or aromatic hydrocarbon; and R.sup.7 is saturated or aromatic hydrocarbon or hydrogen, are converted by cleavage of R.sup.4 OH into corresponding cycloalkenes and protecting groups, if present, are hydrolyzed. The compounds obtained are valuable intermediates in carotenoid syntheses.

Substituted alkynes useful as intermediates in the synthesis of

A process for the manufacture of 3-hydroxy-2,6,6,-trimethyl-2-cyclohexen-2-one, an intermediate in canthaxanthin synthesis, by isomerizing 1,1,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one in the presence of a palladium(O) complex of an acetone derivative of the formula ##STR1## wherein R.sup.1 and R.sup.2 are aryl and R.sup.3 and R.sup.4 are hydrogen or monovalent hydrocarbon groups optionally carrying a carbonyl function, a bis-(diphenylphosphino) derivative of the formula

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Bottmingen, Switzerland

Milan Soukup