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The synthesis of a series of N-substituted O-(3-amino-2-hydroxypropyl)oximes of 1,3,3-trimethyl-5-endo-(1-piperidinyl or 4-morpholinyl)-2-oxabicyclo [2.2.2]octan-6-ones is described. Some of these ethers showed strong local anesthetic activity in mice and platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid, as well as moderate hypotensive, antiarrhythmic and analgesic activities in rats and mice.

The synthesis of [(1-methyl-1H-indazol-4-yl)oxy]acetic acid 4, 1-methyl-1H-indazole-4-acetic acid 9, 2-(1-methyl-1H-indazol-4-yl)propanoic acid 15 and [[(1,5,6,7-tetrahydro-1-methyl-4H-indazol-4-ylidene)amino]oxy]acet ic acid 16, as well as of amides and esters derived from 4 and 9, starting from 1,5,6,7-tetrahydro-1-methyl-4H-indazol-4-one is described. Some of the above compounds showed weak antiinflammatory, analgesic, antipyretic and hypotensive activities in rats and mice, as well as moderate platelet antiaggregating effects in vitro.

A series of omega-dialkylaminoalkyl esters of N-phenyl aminethiocarboximidic acids was prepared by reaction of N-phenyl 1-pyrrolidine, 1-piperidine, 4-morpholine, 1,2,3,4-tetrahydro-1-quinoline, 1,2,3,4-tetrahydro-2-isoquinoline, 10-phenothiazine, N-phenyl-2-pyridylamine and N-benzyl-2-pyridylamine-carbothioamides (prepared in situ from the appropriate secondary amine and phenyl isothiocyanate) with a number of omega-chloroalkyldialkylamines in anhydrous DMF or THF solution in the presence of sodium hydride. Good yields of the above esters were obtained provided that sodium hydride was added initially or after the formation of 3,3-disubstituted 1-phenylthiourea, according to the nature of the secondary amine. Some esters showed in mice local anesthetic activity comparable with that of lidocaine, as well as moderate hypoglycemic, antiarrhythmic, analgesic, antiacetylcholine, H1-antithistamine and platelet antiaggregating activities.

The synthesis in excellent yields of 1-acyl-3-furfuryl-1-phenylthioureas 2 by reacting at t less than or equal to 10 degrees C 3-furfuryl-1-phenylthiourea 1, prepared in situ from furfurylamine and phenyl isothiocyanate, with aromatic or heterocyclic acyl chlorides in pyridine solution is described. 1-Acylthioureas 2 rearranged in high yields to 3-acylthioureas 3 by treatment with sodium hydroxide in heterogeneous phase. 1,3-Diacyl-3-furfuryl-1-phenylthioureas 4 were obtained in satisfactory yields by treatment of 1 with two moles of acyl chloride as in the case of 1-monoacylation. The thiourea 1 prepared in situ reacted with iodomethane in dimethylformamide solution and in the presence of sodium hydride to give in high yield the S-methyl derivative, namely the methyl ester of N-phenyl-1-furfurylaminethiocarboximidic acid. Some acylthioureas 2 and 4 showed a platelet antiaggregating activity in vitro superior or comparable to that of acetylsalicylic acid. The 1,3-diacylthiourea 4 c exhibited an appreciable anticonvulsant activity in mice and some compounds 2 and 4 moderate competitive antiacetylcholine and H1-antihistamine effects in vitro.