THIAZOLIDINE DERIVATIVES AND PROCESS FOR THEIR MANUFACTUR

摘要

1513948 Sulphamoyl- and sulphonyl-containing thiazolidines HOECHST AG 24 July 1975 [27 July 1974] 30973/75 Heading C2C The invention comprises novel compounds (I) (including salts thereof) in which R1 stands for alkyl or alkenyl radicals of 1 to 4 carbon atoms, cycloalkyl radicals of 3 to 6 carbon atoms, or dialkylamino groups having a total of 7 carbon atoms, which may from together with the nitrogen-atom of the amino group a saturated heterocyclic ring. R2 stands for an alkyl or alkenyl or alkynyl radical of 1 to 8 carbon atoms, optionally substituted by alkoxy groups of 1 to 4 carbon atoms, cycloalkyl radicals of 3 to 8 carbon atoms; phenylalkyl radicals of 1 or 2 carbon atoms in the alkyl moiety, optionally substituted in the phenyl ring by halogen, alkyl, alkoxy or alkylene dioxy, further for alkyl groups of 1 or 2 carbon atoms which are substituted by cycloalkyl radicals of 3 to 6 carbon atoms or 5- or 6- membered saturated or unsaturated heterocyclic radicals containing oxygen, nitrogen or sulfur, or for dialkylamino groups having a total of 7 carbon atoms, which may form together with the nitrogen atom of the amino group a saturated heterocyclic ring, and in which R1 and R2 together, may also stand for an alkylene group of 2 to 4 carbon atoms, R3 stands for hydrogen or alkyl of 1 or 2 carbon atoms, R4 and R5 are identical or different and each stands for hydrogen, alkyl or alkenyl radicals of I to 6 carbon atoms, optionally substituted by alkoxy of 1 to 4 carbon atoms, cycloalkyl or cycloalkylalkyl of 3 to 9 carbon atoms, phenyl, phenylalkyl of 1 to 3 carbon atoms in the alkyl moiety, the phenyl ring may, optionally, be substituted by halogen, alkyl, alkoxy or alkylenedioxy, further for alkyl groups of 1 or 2 carbon atoms which are substituted by 5- or 6-membered unsaturated heterocyclic radicals containing oxygen, nitrogen or sulfur, R4 and R5 may also form together with the nitrogenatom a saturated, optionally methyl-substituted 5- or 6-membered heterocyclic ring, in which optionally a CH 2 -group may be replaced by oxygen, and Y stands for hydrogen, halogen, methyl or trifluoromethyl. They are made (a) by reacting compounds (II) (Z is a radical of an activated ester) with thioureas (III) of formula (b) by halogenating (IV) and reacting compounds (V) obtained with (III) and thereafter reacting (VI) obtained with R4R5NH, (c) by reacting compounds (VIII) with Hal . C(:NR1). NHR2 or with (e) by oxidizing compounds (XI) and (f) by interacting (XII) and (XIII) and hydrolysing the products obtained (R4 and R5 are not H, Y is not Br or I and M is Li or MgBr); compounds (I) where R4 and/or R5 are H can be alkylated to give other compounds (I). Pharmaceutical preparations having saluretic and diuretic actions contain (I) as active ingredient. Administration is parenterally.