Gruenenthal Gmbh

Werner P Vollenberg

Oswald K Zimmer

Ulrich G Seipp

Werner Guenter Englberger

Michael Haurand

Johannes Schneider

Werner Winter

Erwin O Kiesewetter

Gerriet K Loschen

Cornelia Geist

Horst R Boehlke

Gudrun E Michel

Ulrich G Seippl

Brigitte J Bosman

Bernd Mueller

Oxyalkyne compounds corresponding to the formula I ##STR1## in which the substituent Y in the meta- or para-position is R.sup.1 represents CH.sub.3 or NH.sub.2, R.sup.2 represents H or CH.sub.3, R.sup.3 represents H, C.sub.1-3 -alkyl or COCH.sub.3, and Ar represents an aromatic residue selected from the group ##STR2## with the proviso that the substituents R.sup.4, R.sup.5 and R.sup.6 are the same or different and each substituent represents H, F, Cl, Br, C.sub.1-6 -alkyl, CF.sub.3 or C.sub.1-6 -alkoxy, and R.sup.7 represents H, F, Cl, Br, C.sub.1-3 -alkyl or CF.sub.3, in the form of their racemates or mixtures of diastereoisomers or in optically active form, which are suitable active ingredients in pharmaceutical compositions.

Oxyalkyne compounds, pharmaceutical compositions containing them and

Substituted 3,4-dihydronaphthalenes of the formula I ##STR1## wherein R.sup.1 is a methyl or an amino group, R.sup.2 represents a hydrogen atom or a methyl group, and R.sup.3 is a linear or branched chain alkyl residue having 1 to 4 carbon atoms, an allyl or a crotyl group or a cyclopentyl group are disclosed which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of disorders attributable to the action of leucotrienes. The dihydronaphthalenes may be prepared by reacting a compound of formula II ##STR2## with hydroxylamine or a salt thereof to form the corresponding oxime, reducing the oxime to a hydroxylamine of formula III ##STR3## and introducing a --CO--R.sup.1 group.

Substituted 3,4-dihydronaphthalenes, pharmaceutical compositions

Substituted phenylacetylenes of the formula ##STR1## wherein one of the groups R.sub.1 is a hydrogen atom and the other represents the group of the formula ##STR2## in which R.sub.3 is hydrogen, methyl or ethyl and R.sub.4 is a methyl or an amino group and wherein R.sub.2 represents mono- or binuclear aromatic or heterocyclic residues containing sulfur, nitrogen or oxygen as hetero atoms and optionally being substituted by 1 to 3 substituents as defined, which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds may be prepared by reacting a compound of the formula ##STR3## wherein R.sub.2 has the same meaning as above and one of the groups R.sub.7 is a hydrogen atom and the other represents the group of the formula --COR.sub.3, with hydroxylamine to form the oxime which then is reduced to the corresponding hydroxylamine compound into which the group of the formula --COR.sub.4 is introduced.

Substituted phenylacetylenes, pharmaceutical compositions containing

Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.5 into another carboxylic acid derivative. By hydrogenation A and B may be varied within the scope of the definition.

Phenol derivatives, pharmaceutical compositions containing these

Phenol derivatives and pharmaceutical compositions containing these

The invention relates to a process for the preparation of 2-Oxabicyclo[3.3.0]octane derivatives of the general formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.5 represent organic radicals and R.sub.2 and R.sub.3 also may represent hydrogen and wherein R.sub.4 is an acyl group or an tri-organo-silyl group and to the compounds of formula I produced by the process of the invention which compounds are valuable intermediates for the preparation of pharmacologically active compounds. The process of the invention comprises reacting a compound of the formula ##STR2## wherein R.sub.14 is lower alkyl or phenyl with a compound of the formula ##STR3## wherein R.sub.15 is trimethylsilyl or lower alkanoyl in an inert solvent at temperatures from about -80.degree. C. to about +60.degree. C. in presence of one or more Lewis acids.

Process for the preparation of 2-oxa-bicyclo [3.3.0] octane derivatives

Disclosed are new heterocyclic compounds, medicaments containing them (for oral or parenteral administration) and processes for the preparation and use of these heterocyclic compounds and medicaments. The new compounds which particularly act as inhibitors of blood platelet aggregation and as blood pressure lowering agents correspond to the general formula ##STR1## wherein R.sup.1 is hydrogen, a cation or the residue of an alcohol, R.sup.2 represents hydrogen or methyl, A is a member of the group consisting of the radicals --CH.sub.2 --CH.sub.2 --, (trans)--CH.dbd.CH-- and --C.tbd.C--, and wherein B represents an alkyl or a cycloalkyl radical. In these compounds the phenyl radical may be arranged with respect to the double bond in the E- and/or in the Z-configuration and at the carbon atom bearing the group R.sup.2 (and others) may exist RS- or S-configuration. The compounds of formula I are prepared in a manner known per se starting from derivatives of 3.alpha.,5.alpha.-dihydroxycyclopentane-1.alpha.-acetaldehyde .gamma.-lactol substituted accordingly and phosphonium salts of the formula ##STR2## wherein R.sup.6 represents hydrogen or alkyl and wherein Hal is chlorine, bromine or iodine.

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Stolberg, Germany

Werner P Vollenberg