AT253688B - Process for the preparation of the new 3- (dibenzo) - [a, d] -1, 4-cycloheptadien-5-yloxy) -nortropane and its pharmaceutically acceptable salts - Google Patents

Description

       

   <Desc / Clms Page number 1>
 



   Process for the preparation of the new 3- (dibenzo- [a, d] -l, 4-cycloheptadien-5-yloxy) -nortropane and its pharmaceutically usable ones
Salts
The invention relates to a process for the preparation of a new dibenzocycloheptane compound having valuable pharmacological properties and to the preparation of pharmaceutically acceptable salts thereof.



   A compound with an analogous structure was already known from Austrian patent specification No. 221495, which, however, differs from the present one in that a methyl group is bonded to the nitrogen atom of the heterocyclic ring. The new compound prepared according to the invention, like this known compound, has a spasmolytic effect, but shows to a much lesser extent some side effects of the latter, namely the mydrotic effect and the effect on the central nervous system.



   The new compound can also serve as an intermediate in the preparation of other therapeutically active compounds, e.g. B. those in which the hydrogen atom on the nitrogen atom is substituted by other groups, such as alkyl groups.
 EMI1.1
 
 EMI1.2
 
 EMI1.3
    (Dibenzo- [a, d] -1, 4-cycloheptadien-- 5-yloxy) -tropane is demethylated in a known manner, in which the starting material is first treated with a cyano halide, whereby the methyl group on the nitrogen atom in the tropane ring is replaced by a cyano group becomes. The N-cyano-nor-tropane compound is then hydrolyzed to form the corresponding N-carboxynortropane compound, from which the desired compound is finally obtained by decarboxylation.



   The salts of 3- (dibenzo- [a, d] -l, 4-cycloheptadien-5-yloxy) -nortropane can be prepared in a known manner. So you can z. B. the base in a suitable solvent, such as diethyl

 <Desc / Clms Page number 2>

 ether, treated with an equivalent amount of the desired acid. The salt usually precipitates out and can be separated off by filtration.



   A salt is expediently used for the therapeutic application of the new compound. Acids suitable for the preparation of these salts are e.g. B. inorganic acids, such as the hydrohalic acids, especially hydrochloric acid and hydrobromic acid, and organic acids such as oxalic acid, maleic acid, fumaric acid, citric acid, tartaric acid, lactic acid, acetic acid, and emboxylic acid (2,2'-dihydroxy- -1,1'-dinaphthylmethane -3,3'-dicarboxylic acid).



   The following example is intended to explain the invention.



   Example 1: a) Preparation of N-cyano-3- (dibenzo- [a, d] -1, 4-cycloheptadien-5-yloxy) - nor- trepan,
To 11.66 g of cyanogen bromide in 100 cm3 of benzene, a solution of 33.0 g of 3- (dibenzo- [a, d] -1,4-cycloheptadiene-5-yloxy) tropane (prepared as in the Austrian . Patent No. 221495) was added in 100 cm3 of anhydrous benzene. The temperature rises a little. The mixture is refluxed for 3 hours and, after cooling, treated with water. The benzene layer is separated and dried over sodium sulfate. After filtration and removal of the solvent by distillation, an oil is obtained.

   Treating the oil with ethanol gives 14 g of crystalline N-cyano-3- (dibenzo- [a, d] -1,4-cycloheptadien-5-yloxy) -nortropane with a melting point of 152 - 1550 C.



  Recrystallization from ethanol gives 12.5 g of the pure compound with a temperature of 158-1600 C.



   Analysis for CZ3HuNp calculated: C = 80, 1910 H = 7.02% N = 8, 13% found: C = 80, 59go H = 6, 96% N = 8, 14%.
 EMI2.1
 river cooling cooked. It is then poured into water and extracted with ether. The layers are separated and the ether layer is dried. After filtering, the nortropane compound is in
 EMI2.2
 d. Th.) The.



   Analysis for CHNOs
 EMI2.3
 : found: C = 71.92%, H = 6.59%, N = 3.52%.



   The compound 3- (dibenzo- [a, d] -1,4-cycloheptadien-5-yloxy) - - nortropane or a salt of this compound prepared according to the invention can be brought into an administration form suitable for pharmaceutical use.


    

Claims (1)

PATENT CLAIM: Process for the preparation of the new 3- (dibenzo- [a, d] -1,4-cycloheptadien-5-yloxy) -nortropane and its pharmaceutically acceptable salts, characterized in that 3- (di- EMI2.4 benzo- [a, d] -1,4-cycloheptadien-5-yloxy) -nortropane to N-carboxy-3- (dibenzo- [a, d] -l, 4-cycloheptadien-5-yloxy) -nortropane , e.g. B. with alkalis, hydrolyzed and the latter compound, e.g. B. by heating, decarboxylated, after which the compound obtained is optionally converted into a pharmaceutically acceptable salt.