US 4,193,926 AGranted

4-(Polyalkoxy phenyl)-2-pyrrolidones

AssigneeSchering Corporation

InventorsRalph Schmiechen, Reinhard Horowski, Dieter Palenschat, Gert Paschelke, Helmut Wachtel, Wolfgang Kehr

Life of this patent

Estimating the term…

Loading patent…

Abstract

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-(polyalkoxyphenyl)-2-pyrrolidones of the formula ##STR49## selected from the group consisting of 4-(3-ethoxy-4-metoxyphenyl)-2-pyrrolidone;

4-(3-propoxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-butoxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-hexyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-isopropoxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(1-methylpropoxy)-4-methoxyphenyl)-2-pyrrolidone;
4-(3-isobutoxy-4-methoxyphenyl)-2-pyrrolidione;
4-(3-allyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(3-methyl-2-butenyloxy)-4-methoxyphenyl)-2-pyrrolidone;
4-(3-methoxymethoxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(2-hydroxyethoxy)-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(2,2,2-trifluoroethoxy)-4-methoxyphenyl)-2-pyrrolidone;
4-(3-benzyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-phenoxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-methoxy-4-ethoxyphenyl)-2-pyrrolidone;
4-(3-methoxy-4-butoxyphenyl)-2-pyrrolidone;
1-acetyl-4-(3,4-dimethoxyphenyl)-2-pyrrolidone;
4-(3-decyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-83-octadecyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(2-methylbutyl)-oxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-neopentyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-isopentyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(2-propinyl)-oxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-cyanomethyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-cyclobutoxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-cyclohexyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(3-methylcyclopentyl)-oxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(2-methylcyclopentyl)-oxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(3-tetrahydrothienyl)-oxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-(3-tetrahydrofuryl)-oxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-cyclopropylmethyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-cyclopentylmethyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(3-methallyloxy-4-methoxyphenyl)-2-pyrrolidone;
4-(4-propinyloxy-3-methoxyphenyl)-2-pyrrolidone;
4-(4-cyclopentyloxy-3-methoxyphenyl)-2-pyrrolidone;
4-(3,4-diethoxyphenyl)-2-pyrrolidone;
4-(3,4-diisobutoxyphenyl)-2-pyrrolidone;
4-(3-isobutoxy-4-methoxyphenyl)-pyrrolidine-2-thione;
4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidine-2-thione;
and
4-(3-(2-tetrahydrofuryloxy)-4-methoxyphenyl)-2-pyrrolidone.

38 more elements

Facts

Application

05/659,082Filed 18 Feb 1976 · continuation in part

Priority

DE 241393520 Mar 1974

Granted

18 Mar 1980

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 207/277
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07D 207/24
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07D 207/26
Oxygen or sulfur atoms: 2-Pyrrolidones
C07D
Heterocyclic compounds

Abstract

Claims45