US 4,376,731 AGranted

1-Aziridine carboxylic acid derivatives with immunostimulant activity

AssigneeBoehringer Mannheim GmbH

InventorsElmar Bosies, Ruth Heerdt, Rudi Gall, Uwe Bicker, Anna E. Ziegler

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Abstract

2-Substituted-1-aziridine-carboxylic acid esters exhibiting immuno-stimulant activity and of the formula ##STR1## wherein X is a carbamoyl or alkoxycarbonyl radical, and R.sup.1 is an aliphatic hydrocarbon radical optionally substituted by halogen, alkoxy, amino, carbamoyloxy, cycloalkyl, hydroxyl, an imido or heterocyclic radical, cycloalkyl; or aryl, aralkyl, aryloxyalkyl or arylthioalkyl wherein the aryl moiety is optionally substituted by halogen, alkyl, alkoxy, hydroxyl, amino, nitro, cyano, acyl, carbalkoxy, thioalkyl, alkylsulphonyl, phenyl or trifluoromethyl. Counterparts where X is --CN and R.sup.1 is as above, except for ethyl, are also new.

Claims8

Dependent claims

A 1-aziridine-carboxylic acid ester compound of the formula ##STR9## wherein R.sup.1 is methyl;

propyl;
butyl;
amyl;
a C.sub.2-5 unsaturated aliphatic hydrocarbon radical;
a C.sub.1-5 aliphatic hydrocarbon radical substituted up to three times by chlorine, bromine, fluorine, C.sub.1-5 alkoxy, amino, carbamolyoxy, C.sub.3-10 cycloalkyl, hydroxyl, a phthalimido radical, or a tetrahydrofuryl or tetrahydrothienyl radical, cycloalkyl;
or phenyl, naphthyl, benzyl, phenethyl, phenoxyethyl or phenylthioethyl wherein the phenyl or naphthyl moiety is optionally substituted up to 3 times by chlorine, bromine, fluorine, C.sub.1-5 alkyl, C.sub.1-5 alkoxy, hydroxyl, amino, nitro, cyano, formyl, acetyl, carbo C.sub.1-5 alkoxy, -SCH.sub.3, phenyl or trifluoromethyl.

3 more elements

Dependencies are inferred from the claim text.