Azadibenzocycloheptene Derivatives

• Main Authors: PETRUS SIMON HOFMAN, CORNELIS VAN DER STELT
• Format: Patent
• Language: English
• Published: 10.09.1969
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1,163,921. Azadibenzocycloheptene derivatives. KONINKLIJKE PHARMACEUTISCHE FABRIEKEN v/h BROCADESSTHEEMAN & PHARMACIA N.V. 25 Jan., 1967 [27 Jan., 1966], No. 3785/66. Heading C2C. Novel compounds I (including acid addition and quaternary ammonium salts thereof) wherein X signifies -CH 2 .CH 2 or -CH = CH-, R 1 and R 2 signify hydrogen, halogen or alkyl and R 3 represents a basic nitrogen containing radical of less than 16 carbons selected from (a) groups of the formula -A-B, wherein A represents an alkylene radical and B represents alkylamino, dialkylamino, piperidino, pyrrolidino, morpholino or thiamorpholino, (b) groups of the general Formula II wherein R 4 signifies hydrogen or alkyl, m is 0, 1 or 2 and n is 1 or 2, and (c) saturated bicyclic nitrogen containing heterocyclic radicals, are obtained by the interaction of a compound III and a compound of the formula Z.R 3 , wherein one of the symbols Y and Z signifies halogen and the other a group -OM (wherein M signifies an alkali metal atom), or wherein Y signifies halogen or hydroxy and Z signifies hydroxy; the carbinols III (Y is -OH) are obtained by reducing, e.g. with sodium borohydride, the corresponding 5-oxo compound and the halides III (Y is halogen) are derived from said carbinols utilizing, e.g. thionyl chloride. Pharmaceutical preparations showing antihistaminic, sedative, spasmolytic and antidepressive properties and particularly useful in the treatment of asthmatic diseases, contain as active ingredient the above novel compounds; administration may be orally or parenterally.