IL27994A - N-oxide derivatives of dibenzocycloheptenes and process for their preparation - Google Patents

Description

derivatives and process for preparation 2 The invention relates to derivatives of In particular the invention relates of and of the corresponding and to salts The new compounds according to the invention wherein Z is or R is a straight or branched chain lower preferably having up to 6 carbon or a radical wherein is halogen or lower alkyl having up to 4 carbon atoms and is or R is lower A is hydrogen when Z is OH or the radical R whe Z is OH or or and A together form the radicals or is hydrogen or and which may be the same or are straigh or branched lower alkyl preferably having up to 6 carbon or atoms be linked together through an atom of nitrogen or oxyge form heterocyclic ring having 6 atoms therein such as or the lower l substitue t of the preferably having up to 4 carbon is or a group wherein is 1 or n is 0 or is alkoxy or and X and which may be the same or different are an alk lsulfonyl group up to 4 carbon or a group having up to 8 carbon compounds represented by the above structural formulae can advantageously be employed in pharmaceutical applications because they have been found to possess depressant As a they be administered orally in the form of sustained release pellets and the like or they may be administered orally or in the form of aqueous solutions or when administered orally or satisfactory results are obtained at a daily dosage level of from about one mg to about preferably given in divided doses over the day or in sustained release The compounds are preferably administered in the form of thei acid addition salts and these salts are included within the scope of this invention also relates to a prooess for the preparation of of formulae or XXX by treating a compound of formulae XX or in the free base with hydrogen peroxide in an organic solvent such as a lower preferably free bases to be used as starting materials are also new compounds and have been described in Patent Specifications and Where starting materials are used in which both a primary and a tertiary amino group only the of the tertiary amino group is Where two tertiary amino groups are present the group is formed on both of The invention is by way of Example by the following trans trans and 20 of absolute methanol are stirred and cooled in an Hydrogen of is added Stirring is continued for 1 hour in the oold and for 19 hours at room temperature and the mixture then is allowed to stand for 24 hours at room After cooling in an the mixture is treated with a suspension of 100 of palladium on charcoal in 1 of water and stirred at room temperature for hours when a test for peroxide ia After filtration through a mat of the filtrate is evaporated below 4 under reduced The residual colorless glass weighs after drying for 3 days in a vacuum desiccator over phosphorus pe She base is converted to the hydrogen maleate by dissolving it in 20 of cold absolute ethanol and adding a solution of 860 of malelo aoid in of absolute Dilution to incipient crystallization with 25 of absolute ether precipitates the hydrogen in a yield of from cold absolute a o ether gives dec Analysis for By the same method as described above the following can be dimethyl oxide EXAMPLE 2 By the method as described in Example but using as starting rial the corresponding of formula XX has been 8 insufficientOCRQuality

Claims (1)

1. derivatives of cloheptenes and of the corresponding compounds of the is a straight or chain lower preferably having up to 6 carbon or a radical rein is haloge or to 4 carbon atoms and is 0 or is lower A is hydrogen when is or or the radical when 2 is OH or o Z and together form the radicals or is hydrogen or lower and which may be the same or different are straight or branched chain Or lower alkyl preferably having up to 6 carbon be linked together through an atom of nitrogen or oxygen to a heterocyclic ring having from 5 to 6 atoms therein such as or the lower alkyl substituent 9 of the latter preferably having up to 4 carbon is or a group wherein is 1 or n is 0 or B is alkoxy or and X and which may be the same or different are an alkylsulfonyl group having up to 4 carbon or a dialkylsulfamoyl group having up to 8 carbon acid addition salts of such and of and of the corresponding of formula I or II in Claim substantially as described and exemplified Λ process for the preparation of derivatives of according to wherein the corresponding dibenzocycloheptene compound having a tertiary propyl group in the position a tertiary amino group i the position reacted with hydrogen peroxide in an inert organic if the derivative is converted into an addition A process according to wherein the inert organic solvent is an A process for the preparation of derivatives of dibenzocycloheptenes according Claim substantially as described derivatives of and of corresponding compounds according to Claim when prepared by the process according to any of Claims to Pharmaceutical compositions comprising as an aotive ingredient an derivative of according to Claim 1 or a pharmaceutically acceptable acid addition salt Dated this day of May 1967 insufficientOCRQuality