Verfahren zur Herstellung von neuen 5,6-Dihydro-dibenz(b,e)-azepinen

Novel compounds of Formula I in which R1 is hydrogen or alkyl, R2, R3, R4 and R5 are hydrogen or alkyl, and R6 is alkyl, or R6 and one of R2, R3, R4 and R5 together with the nitrogen atom and any intervening carbon atoms form a saturated 5-, 6- or 7-membered heterocyclic ring which may be interrupted by a further hetero atom and may be substituted by at least one alkyl group, the alkyl groups having 1-5 carbon atoms, X and Y are hydrogen or halogen, and Z is a carbonyl or methylene group, and their non-toxic acid addition and quarternary ammonium salts, are prepared (1) when Z is a carbonyl group, by dehydrating the corresponding 11-hydroxy-11-aminoalkyl-5, 6-dihydromorphanthridine-6-one, or by simultaneous rearrangement and dehydration of the corresponding 10-hydroxy-10-aminoalkylanthrone oxime, (2) when Z is a methylene group, by reducing a compound of Formula I wherein Z is a carbonyl group, using a complex metal hydride in an anhydrous solvent, and (3) when R1 is an alkyl group, by alkylating the corresponding compound of Formula I wherein R1 is hydrogen. The 11 - hydroxy - 11 - aminoalkyl - 5,6 - dihydromorphanthridine-6-ones may be prepared by treating the corresponding 5, 6-dihydromorphanthridine-6, 11-diones with an aminoalkyl magnesium halide in an anhydrous solvent. The 10-hydroxy-10-aminoalkylanthrone oximes are made by reacting an anthraquinone with an aminoalkyl magnesium halide and treating the 10 - hydroxy - 10 - aminoalkylanthrone with hydroxylamine. Therapeutic compositions having antihistamine, psychotropic, antiemetic, narcosis-potentiating, adrenolytic, antipyretic, hypothermal, spasmolytic, antitussive, antichlinergic, sedative and/or antisertonin activity, which may be administered orally, rectally, parenterally or topically, contain as active ingredients compounds of Formula I above or the non-toxic acid addition and quaternary ammonium salts thereof.