Klinge Pharma Gmbh

Klinge Pharma Gmbh & Co.

Helmut Grill

Roland Loser

Rainer Hans Zschocke

Josef Wagner

Friedemann Reiter

Klaus Seibel

Michael Schliack

Gernot Hofrichter

P Stefan Janiak

Axel Woschina

Helmut Schickaneder

Hans-Helmut Henschel

Gerhard Lang

Method for the production of E-1-�4'- (2- Dimethylaminoethoxy) -

The invention relates to p-oxibenzoic acid derivatives of the general formula (1) where: ##STR1## their diastereomers and enantiomers in pure form or as mixture of stereoisomeric forms and their physiologically compatible salts, a process for the preparation thereof and the use thereof for preparing drugs with hypolipemic effect.

New p-oxibenzoic acid derivatives, process for their preparation and

Novel (E)-1-[4'-(2-alkylaminoethoxy)phenyl]-1- (3'-hydroxyphenyl)-2-phenylbut-1-enes of the general formula ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different, provided that, when R.sup.1 and R.sup.2 are the same, each of them is a methyl or ethyl radical, and when R.sup.1 and R.sup.2 are different, one of them is hydrogen and the other is a methyl or ethyl radical, and the therapeutically compatible salts thereof, have a marked anti-estrogenic effect and are suitable for treating hormone-dependent mammary tumors. The compounds can be prepared by dehydrating carbinols of the general formula ##STR2## wherein R.sup.1 and R.sup.2 may be the same or different, provided that, when R.sup.1 and R.sup.2 are the same, each of them is a methyl or ethyl radical, and when R.sup.1 and R.sup.2 are different, one of them is a benzyl radical and the other is a methyl or ethyl radical; and wherein R.sup.3 is hydrogen or an easily hydrolyzable protecting group, through the action of mineral acid while removing any protecting group present, isolating through crystallization the E-form from the pair of isomers obtained, and removing by hydrogenolysis any benzyl group present. Compositions comprising the subject 1,1,2-triphenylbut-1-ene derivatives are described also. The corresponding novel 1,1,2-triphenylbut-1-ene derivatives having the (Z) configuration are also disclosed.

1,1,2-triphenylbut-1-ene derivatives

The invention concerns the direct preparation of trans-1,1,2-triphenyl-but-1-ene derivatives having the general formula 1 by dehydration of carbinols having the general formula 2 by heating in a strongly hydrochloric or sulphuric acid medium with the exclusion of organic solvents. ##STR1##

Process for the preparation of trans-1,1,2-triphenyl-but-1-ene

Para substituted benzoic acid derivatives of general formula (1) ##STR1## and their physiologically compatible salts, where R.sup.1 may be H, isopropyl, t-butyl p0 X may be ##STR2## and R.sup.2 may be --OH, --OR', where R' is a linear or branched, saturated or unsaturated C.sub.1 to C.sub.3 alkylmoiety, or a --NHCH.sub.2 COOH-- group, have hypolipedemic activity. They may be obtained by known methods either from the corresponding unsaturated ketones or from saturated hydroxycompounds, where the esterified benzoic acid moiety may be saponified or converted to a carboxymethylamide.

New benzoic acid derivatives, as well as processes for their production

P-oxybenzoic acid derivatives of formula (1) ##STR1## wherein R.sup.1 is hydrogen, or straight or branched alkyl of one to four carbon atoms;

Novel p-oxybenzoic acid derivatives, processes for their production and

Compounds of the formula ##STR1## wherein R.sup.1 is Cl, Br, CH(CH.sub.3).sub.2 or C(CH.sub.3).sub.3 ; A is a single bond, --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; and R.sup.2 is H, the cation of a pharmaceutically acceptable salt or an alkyl of up to three carbons, are strong hypolipaemic agents.

Novel derivatives of 1,3-diphenoxypropane-2-on, process of their

New 1,3-disubstituted propanol-(2) derivatives and their nicotinic acid esters of the general formula ##STR1## and their therapeutically acceptable salts, processes for preparing the same and the use thereof and pharmaceutical preparations containing the same for the treatment of hyperlipemia.

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Vaterstetten, Germany

Helmut Grill