Process of preparing cycloalkano(1,2-B)indole-sulphonamides
AssigneeBayer Aktiengesellschaft
InventorsHorst Boshagen, Ulrich Rosentreter, Folker Lieb, Hermann Oediger, Friedel Seuter, Elisabeth Perzborn, Volker-Bernd Fiedler
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Abstract
Cycloalkano[1,2-b]indole-sulphonamides of the formula ##STR1## where appropriate in an isomeric form, and their salts are disclosed. These compounds are useful to inhibit platelet aggregation and to antagonize thromboxane A.sub.2.
Claims1
A process for preparing a cycloalkano[1,2-b]indole-sulphonamide of the formula ##STR86## or a salt thereof comprising reacting a (benzenesulphonamidoalkyl)cycloalkano[1,2-b]indole of the formula ##STR87## in which R.sup.1 represents hydrogen, halogen, trifluoromethyl, carboxyl or alkoxycarbonyl;
- or represents a group of the formula --S(O).sub.m R.sup.3,
- in which
- R.sup.3 denotes alkyl or aryl, and
- m denotes one of the numbers 0, 1 or 2;
- represents a group of the formula ##STR88## in which R.sup.4 and R.sup.5 are identical or different and represent hydrogen, alkyl, aryl, aralkyl or acetyl;
- or represents a group of the formula --OR.sup.6,
- in which
- R.sup.6 denotes hydrogen, alkyl, aryl, aralkyl, alkyl-SO.sub.3 --, aryl-SO.sub.2 --, aralkyl-SO.sub.2 -- or trifluoromethyl;
- or represents alkyl, alkenyl or cycloalkyl each of which is unsubstituted or substituted by carboyl, alkoxycarbonyl, halogen, hydroxyl, alkoxy, alkylthio or cyano,
- R.sup.1 represents aryl which is unsubstituted or substituted up to 5 times by halogen, cyano, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, alkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxy, alkylthio, hydroxyl, carboxyl, alkoxycarbonyl, phenyl, phenoxy, benzyloxy, benzylthio or by a group of the formula ##STR89## in which R.sup.4 and R.sup.5 have the abovementioned meanings,
- x represents the number 1, 2 or 3, and
- y represents the number 0 or 1, with acrylonitrile inthe presence of an inert solvent, hydrolyzing the resultant N,N'-biscyanoethyl compound, and then in the case where a cycloalkano[1,2-b]dihydroindole-sulphonamide is being prepared, hydrogenating the cycloalkano [1,2-b]indolesulphonamide in the presence of an acid and of a reducing agent, or in the case where the salts are being prepared, conducting a reaction with an appropriate base.
Dependencies are inferred from the claim text.