摘要 |
<p>The invention comprises compounds of the formula <FORM:0912789/IV (b)/1> and non-toxic cationic salts thereof, wherein R is cyclohexyl or cycloheptyl and X is the group -CO- or -CHOH- and non-toxic cationic salts thereof, and their preparation by treating an amide, imide or isocyanate having at least one para-substituted phenyl radical of the formula CH3.X.C6H4.SO2- with an isocyanate or an amine having a cycloalkyl radical and if desired concurrently or subsequently reacting with a base or basic salt and/or if X is a -CO- group, hydrogenating to produce the corresponding carbinol. Suitably, for example an ethyl phenylsulphonylcarbamate or a phenylsulphonylisocyanate is reacted with cyclohexyl- or cycloheptyl-amine; an N-cycloalkyl urethane is reacted with a phenylsulphonamide or the reaction product of two molecules of a p-substituted phenylsulphonamide is pyrolyzed with a cycloalkylamine. If the starting material is a carbinol (X = -CHOH-), the hydroxy group may be protected by an acyl or alkoxycarbonylamino group which is subsequently removed by hydrolysis. p-Acetylbenzenesulphonamide is made by converting p-aminoacetophenone to p-acetylbenzenesulphonyl chloride by diazotising and reacting with sulphur dioxide and cupric chloride, which is then reacted with ammonia. N - p - acetylphenylsulphonyl - carbamate is obtained by treating the above sulphonamide with ethyl chloroformate. Pharmaceutical preparations useful as antidiabetic agents comprise the compounds of the invention in oral dosage forms such as tablets or capsules containing conventional binders, fillers or other excipients.</p> |