Katsutada Masuda

Biotransformation of Molsidomine (N-Ethoxycarbonyl-3-morpholinosydnonimine), a New Anti-anginal Agent, in Rats

Abstract1. After oral administration of [14C]N-ethoxycarbonyl-3-morpholinosydnon-imine (molsidomine) to rats, 85.0% of the ingested radioactivity was excreted in urine in 24 h. Metabolites found in the urine were molsidomine (0.6% of urinary radioactivity), 3-morpholinosydnonimine (compound A, 8.4%) and N-cyanomethylenaminomorpholine (compound C, 15%). About 48% of urinary radioactivity was accounted for by approximately equal amounts of the two weakly acidic metabolites N-cyanomethylenaminomorpholine-2-one (compound D) and N-cyanomethylenamino-N-(2-hydroxyethyl)-glycine (compound E).2. In 24 h after intraduodenal injection of [14C]molsidomine to rats, 13.3% of the radioactivity was excreted in the gastric juice as molsidomine (95%) and compound C (4.8%). Much of the molsidomine in the gastric juice was present a polar, conjugate-like compound, which on purification by t.l.c. was converted to the parent drug.3. After intravenous injection of [14C]molsidomine to rats, the blood level declined biphasically ...

Studies on mesoionic compounds. Part 11. Alkylation of 5-acylamino-1,2,3-thiadiazoles

The alkylations of 5-acylamino-1,2,3-thiadiazoles (4) have been investigated; the N-3 position is preferably alkylated forming new mesoionic heterocycles (5) and (10). The mesoionic 1,2,3-thiadiazolium-5-alkoxy- and -5-aryloxy-carbonylaminides are converted into the corresponding salts of the 5-imine derivatives (11) by hydrolysis with hydrochloric acid.

Studies on mesoionic compounds. Part 10. Synthesis and chemical properties of mesoionic 1,2,5-thiadiazolium-3-olates

The preparation of a novel mesoionic heterocycle is described; derivatives of 4-aryl-5-alkyl-1,2,5-thiadiazolium-3-olates (6a–f) are obtained by treatment of α-N-substituted aminophenylacetamides with sulphur monochloride followed by base.

Mesoionic 1,2,5-thiadiazolium-4-olates

α-Alkylaminophenylacetamide derivatives (1) reacted with sulphur monochloride followed by treatment with base to give a new mesoionic heterocyclic system, 1,2,5-thiadiazolium-4-olates (3).