GB1075358A - New azetidine derivatives and the preparation thereof - Google Patents

Abstract

Novel compounds of the general formulae <FORM:1075358/C2/1> <FORM:1075358/C2/2> wherein R is (C1-C6) alkyl, (C1-C6) hydroxy-alkyl, cycloalkyl or aralkyl, R1 is (C1-C6) alkyl, (C1-C6) hydroxyalkyl, or (C1-C6) dihydroxyalkyl monoesterified with an alkyl sulphonic acid, aryl sulphonic acid or alkaryl sulphonic acid, or R and R1 may, together with the adjacent nitrogen atom in the azetidine ring, form a heterocyclic ring, and R2 is (C1-C6) alkyl, alkaryl or aryl, are prepared either by heating a compound of the general formula X.CH2.CH(OH).CH2N.R.R1 or <FORM:1075358/C2/3> wherein X is a halogen atom, with a compound of the general formula Ag.OSO2.R2, or by ion exchange from compounds of the formulae <FORM:1075358/C2/4> <FORM:1075358/C2/5> wherein X(-) is a halide ion, by either using an ion exchange resin or treatment with the appropriate sulphonic acid or silver salt thereof, or by reacting at low temperature a primary or secondary amine of the general formula HNR3R4, wherein R3 is H, alkyl or hydroxyalkyl and R4 is alkyl, hydroxyalkyl, cycloalkyl or aralkyl or R3 and R4 together represent a heterocyclic ring, with a b ,g -epoxy-a -alkyl- or arylsulphonyloxypropane of the general formula <FORM:1075358/C2/6> of the molar ratio of 1:2 in the case of a primary amine or in the case of a secondary amine in the molar ratio of 1 : 1. b ,g -Epoxy-a -alkyl or aryl-sulphonyloxypropanes of the above general formula are prepared by the reaction of an alkyl- or aryl-sulphonyl chloride with glycidol in benzene in the presence of triethylamine. g -Halo-b -hydroxylamines of the third formula above are prepared by the reaction of epichlorohydrin with a secondary amine of the general formula NHR1R in equimolar proportions. Therapeutic compositions for oral and parenteral administration, having anti-tumour properties, comprise a compound of the first general formula above and an inert carrier and/or diluent.