Nouveaux dérivés du dibenzocycloheptadiène et leur préparation

摘要

Novel compounds of the Formula I and their acid addition and quaternary ammonium salts, wherein R1 and R2, the same or different, represent hydrogen atoms or alkyl, hydroxyalkyl or dialkylaminoalkyl radicals or R2 may also represent an alkanoyl radical or NR1R2 represents one of the heterocyclic radicals of the Formula II, wherein each of R and R1 represent hydrogen atoms or hydroxy, monoalkylamino, dialkylamino, N-alkylalkanoylamino or phenyl radical with the proviso that R does not represent a hydroxy radical when R1 represents a monoalkylamino, dialkylamino, N - alkylalkanoylamino or hydroxy radical and R11 represents a hydrogen atom or an alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkoxyalkyl, alkoxycarbonylalkyl, N-phenyl-carbamoylalkyl, phenyl, phenylalkyl or phenylalkenyl, the aforesaid phenyl radicals being optionally substituted by halogen atoms or alkyl, alkoxy, nitro, amino, or cyano radicals and the aforesaid alkyl, alkenyl, alkynyl, alkoxy and alkanoyl radicals having up to 5 carbon atoms, are prepared by reacting a compound of the Formula III, wherein X represents a halogen atom or a sulphuric or sulphonic ester residue, with an amine of the formula NHR1R2, or where -NR1R2 represents a 4-substituted-piperazino or -hexahydro-1,4-diazepin-1-yl radical by reacting the corresponding 4-unsubstituted compounds with a compound of the formula X-R111, where R111 has the same meaning as R11 except that it does not represent a hydrogen atom and, if desired, converting a resultant compound of the Formula I into another compound of the Formula I using known methods and, if desired, converting a resulting free base into an acid addition or quaternary ammonium salt thereof. The compound of the Formula I where -NR1R2 represents -NH2 may be prepared by reducing 10-oximino - 5H - 10,11 - dihydrodibenzo[a,d]-cycloheptene. 10 - Chloro - 10,11 - dihydro - 5H - dibenzo-[a,d]cycloheptene may be prepared by reacting the corresponding 10-hydroxy-compound with thionyl chloride. 1 - (1 - Phenylethyl)piperazine may be prepared by reacting 1-chloro-1-phenylethane with piperazine. 1 - (2 - Methylbenzyl)piperazine may be prepared by reacting 2-methylbenzyl bromide with piperazine. 4 - Dimethylaminopiperidine may be prepared by hydrogenating a mixture of 1-benzyl-4-piperidone and dimethylamine in the presence of Raney nickel and hydrogenating the resulting 1-benzyl-4-dimethylaminopiperidine in the presence of palladium on carbon black. Therapeutic compositions with sedative, anti-depressant, anti-histaminic, anti-serotoninic, analgesic and spasmolytic properties in forms suitable for oral, parenteral, or rectal application, comprise compounds of the Formula I or a non-toxic acid addition or quaternary salt thereof with a suitable carrier.