New indole derivatives

摘要

Novel indole derivatives of the general formula wherein X is hydrogen, fluorine, chlorine' bromine or C1-C4 alkyl or alkoxy, R1 is hydrogen, C1-C4 alkyl, or benzyl, Y is hydrogen or a radical where Z is phenyl optionally substituted by one or more substituents defined by X, or is a pyridyl radical, and R2 is hydrogen or C1-C4 alkyl, and the acid addition salts thereof, are prepared by reacting a phenyl hydrazine with a hexahydro-4H-azepin-4-one, and immediately ring-closing the resulting phenyl hydrazone in the presence of an acid condensing agent; or by condensing a substituted phenyl hydrazine in aqueous acid medium with a ketal of a hexahydro-4H-azepine-4-one; or by reacting the compound of the above general formula wherein the 6-position is unsubstituted with a reactive ester of a compound of formula HO-CHZ-R2 in the presence of an alkaline condensing agent, or by reacting the compound of the above general formula wherein the 3-position or the 3- and 6-positions are unsubstituted with a reactive ester of the required alkanol in the presence of an acid binding agent, or with the required alkanal under reducing conditions; or by debenzylating compounds with R1 representing benzyl to form the 3-unsubstituted compounds. 2,3,4,5 - Tetrahydro - azepino - [4,5 - b]-indole is also prepared by reacting 3-methyl-2,3,4,5 - tetrahydro - 1H - azepino - [4,5 - b]-indole with chloroformic acid ethyl ester and heating the resulting 3-ethoxycarbonyl-2,3,4,5-tetrahydro - 1H - azepino - [4,5 - b] - indole with a solution of potassium hydroxide in diethylene glycol monomethyl ether. Therapeutic compositions with antihistaminic and antitussive properties which may be administered orally, rectally or parenterally, and which contain as the active ingredient a compound of the above general formula or an acid-addition salt thereof in admixture with an inert carrier.