Schering Aktiengesellschaft

Gert Paschelke

Wolfgang Kehr

Dieter Palenschat

Helmut Wachtel

Ralph Schmiechen

Reinhard Horowski

Rudolf Wiechert

Andreas Huth

Dieter Seidelmann

Ulrich Kerb

Bernd Muller

Herbert H Schneider

Karl Petzoldt

Dieter Rahtz

Eberhard Schroder

Klaus Kieslich

Otto Engelfried

Novel aminoalkoxyphenylpyrrolidones of the following formula show antihypertonic activity: ##STR1## wherein R.sub.1 is H or OCH.sub.3 ;

Aminoalkoxyphenylpyrrolidone antihypertonic agents and use thereof

4-(Polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR1## wherein R.sub.1 and R.sub.2 each are hydrocarbon of up to 18 carbon atoms at least one being other than methyl, a heterocyclic ring, or alkyl of 1-5 carbon atoms substituted by halogen, OH, COOH, alkoxy, alkoxycarbonyl or an amino group; R' is H, alkyl, aryl or acyl; and X is O or S; possess neuropsychotropic activity. The compounds wherein X is O can be produced by saponifying and decarboxylating a corresponding 2-pyrrolidone-3-carboxylic acid alkyl ester or cyclizing a corresponding 3-phenyl-4-amino-butyric acid or alkyl ester thereof. The pyrrolidones can be converted to the corresponding thiopyrrolidones by reaction with phosphorous pentasulfide in the presence of base.

4-(Polyalkoxy phenyl)-2-pyrrolidones

Novel 5-(substituted phenyl)-oxazolidinones and their sulfur analogs of Formula I ##STR1## wherein R.sub.1 is optionally substituted lower alkyl, cycloalkyl or cycloalkylalkyl;

5-(Substituted phenyl)-oxazolidinones and their sulfur analogs

4-(Polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrocarbon; R.sub.3 is hydrogen or methoxy;

4-(Polyalkoxyphenyl)-2-pyrrolidones (II)

Diacylapomorphines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are both acyl of 1-17 carbons are symptomatically effective agents in the treatment of motor disorders of the type associated with a dopamine deficiency of the extrapyramidal system of the central nervous system, e.g. Parkinson's disease. Pharmaceutical compositions containing these compounds as an active ingredient are described, as well as new compunds of the above formula wherein R.sub.1 and R.sub.2 are formyl or acyl of 3-17 carbon atoms.

Diacylapomorphines

D-homo-20-ketopregnanes of the formula ##STR1## wherein R.sub.1 is oxygen, ##STR2## in which R.sub.5 is hydrogen or lower acyl; R.sub.2 is hydrogen or methyl; R.sub.3 is oxygen, ##STR3## or two hydrogen atoms; R.sub.4 is hydrogen, hydroxy or acyloxy; R.sub.6 is hydrogen or methyl; and R.sub.7 is hydrogen, acetyl, hydroxy or lower acyloxy in the .alpha.- or .beta.-position possess CNS-depressant activity, including anesthesia upon parenteral administration, and are produced by hydrogenating the corresponding steroids having double bonded C.sub.5 and/or C.sub.16 carbon atoms.

D-Homo-20-ketopregnanes

18-Methyl-19-nor-20-keto steroids of the formula ##STR1## wherein R.sub.1 and R.sub.2 collectively are an oxygen atom, or each is hydrogen, or one of R.sub.1 and R.sub.2 is hydrogen and the other is hydroxy, and R.sub.3 is a ketonic oxygen atom or two hydrogen atoms, possess CNS-depressant activity, especially anesthetic-narcotic activity.

18-Methyl-19-nor-20-ketopregnanes and process for the preparation thereof

Benzomorphans of the formula ##STR1## wherein R.sub.1 is H, CH.sub.3 or C.sub.2 H.sub.5 ; R.sub.2 is CH.sub.3 or C.sub.2 H.sub.5 and R.sub.3 and R.sub.4, which can be alike or different, each are lower alkyl, and the acid addition salts thereof with physiologically acceptable acids have CNS activity, including analgesic, morphine antagonistic, anti-convulsive, muscle relaxant, sedative and neuroleptic activity.

Benzomorphan derivatives

4-(Polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR1## wherein R.sub.1 and R.sub.2 each are hydrocarbon of up to 18 carbon atoms or alkyl of 1-5 carbon atoms substituted by halogen, OH, COOH, alkoxy, alkoxycarbonyl, carboxamido or amino or collectively are alkylene of 1-3 carbon atoms, R.sub.3 is H or OCH.sub.3, R.sub.4 is H, alkyl, aryl or acyl and X is O or S possess neuropsychotropic activity. The compounds wherein X is O are produced by saponifying and decarboxylating a corresponding 2-pyrrolidone-3-carboxylic acid alkyl ester or cyclizing a corresponding 3-phenyl-4-aminobutyric acid or alkyl ester thereof. The pyrrolidones are converted to corresponding thiopyrrolidones in a conventional manner, e.g., by reaction with phosphorous pentasulfide in the presence of base.

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Berlin, Germany

Gert Paschelke