GB1065965A - Dibenzocyclooctenes - Google Patents

Abstract

New compounds of general formulae <FORM:1065965/C2/1> <FORM:1065965/C2/2> where R is hydrogen or C1- 6 alkyl and R1 is C1- 6 or NRR1 is a piperidino, morpholino, pyrrolidino or N-(C1- 5 alkyl)-piperazino ring, and X and X1 are hydrogen, halogen, C1- 6 alkyl, C2- 6 alkenyl, C1- 4 perfluoroalkyl, phenyl, substituted phenyl, C1- 4 acyl or perfluoroacyl, amino, C1- 4 alkylamino, C1- 8 dialkyl-amino, C1- 4 alkylsulphopylamino, hydroxy, C1- 4 alkoxy or perfluoroalkoxy, cyano, carboxy, carbamoyl, dialkylcarbamoyl, C2- 6 carbalkoxy, mercapto, C1- 4 alkylmercapto or perfluoroalkylmercapto, C1- 4 alkylsulphonyl or perfluoroalkylsulphonyl, sulphamoyl, C1- 4 alkylsulphamoyl or C2- 8 dialkylsulphamoyl, more than one substituent being optionally present on each benzene ring, and their non-toxic acid addition salts are prepared by reacting a keto-dibenzocyclooctene with a tertiary amino-propyl-grignard reagent to form the 12 - hydroxy - 12 - (tertiary amino - propyl)-compound which is then dehydrated to compounds B or reduced (with hydrogen iodide) or dehydrated and then reduced to compounds A, an optional last step comprising direct or indirect dealkylation of the products. Intermediate 12 - [3 - (N - cyano - N - methyl)-aminopropyl] - 5,6,7,12 - tetrahydro-dibenzo-[a,d]-cyclooctene is prepared. Pharmaceutical compositions comprise the new compounds with carriers, particularly for oral and parenteral administration as tranquillizers and antidepressants. Reference has been directed by the Comptroller to Specification 1,004,926.