Ciba-geigy Corporation

Alex Meisels

Angelo Storni

Claus D Weis

Karl Schaffner

Jean Claude Roger

Compounds of the class of 2,2'-azines of 2,4-thiazolidinediones which are substituted in at least one of the 3-positions by allyl, 1-methylallyl, 2-methylallyl or 2-propynyl and in at least one of the 5-positions by hydroxy, and may further contain methyl groups in the remaining 3-position and in the 5-positions, and the corresponding tautomeric 1-[[4-oxo-2-thiazolidinylidene]amino]-5-hydroxy-2-thiohydantoins and 5,5'-dihydroxy-2,2'-dithio-1,1'-bihydantoins have valuable pharmacological properties. In particular, they inhibit the growth of tumours, while their toxicity is low in comparison with their tumour-inhibiting effectiveness. A specific embodiment is the 2,2'-azine of 3-(2-methylallyl)-5-methyl-2,4-thiazolidinedione and of 3-methyl-5-hydroxy-2,4-thiazolidinedione.

Derivatives of 2,4-thiazolidinedione

Compounds of the class of spiro[norbornane-2,3'-piperidines], spiro[bicyclo[2.2.2]octane-2,3'-piperidines], and corresponding spiro-pyrrolidine derivatives which are unsubstituted at the ring nitrogen atom or substituted by neutral or basic radicals, and the pharmaceutically acceptable acid addition salts of these new compounds possess valuable pharmacological properties and are active ingredients for pharmaceutical compositions. In particular, these new compounds have an antiviral activity. Specific embodiments are (1RS,2RS,4SR)-spiro[norbornane-2,3'-piperidine]-hydrochloride and 1'-[2-(2-azaspiro[5.5]undec-2-yl)-ethyl]-spiro[bicyclo[2.2.2]octane-2,3'-p iperidine]-dihydrochloride.

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Basel, Switzerland

Alex Meisels