Synthesis and pharmacological study of symmetrical bis-quaternary salts related to 3-benzyl-3,9-diazabicyclo-[3.3.1]nnonane

Abstract

In preceding communications we have descr ibed the proper t ies of symmet r i ca l b i s -qua te rna ry salts of the 9-methyl-3,9-diazabicyclo[3.3.1]nonane se r i e s with methylene chains joining the nitrogens in the 3-posit ion [1-3]. The present study is devoted to the synthesis and pharmacological study of symmet r i ca l b i s -qua te rna ry salts (I) which are der ivat ives of 3-benzyl-3,9-diazabicyclo[3.3.1]nonane with a methylene chain joining the nitrogens in the 9-posit ions. These salts were prepared by the react ion of 3-benzyl -3 ,9diazabicyelo[3.3.1]nonane (II) [4] with the diacid chlorides of succinic, glutaric, adipic, pimelic and azelaic acids, with subsequent lithium aluminum hydride reduct ion of the amides which were formed, and convers ion of the t e r t i a ry amines IV into b i s -qua te rna ry salts with the aid of methyl iodide. The symmet r i ca l b i s -qua te rna ry salt containing a 3-methylene group chain (I, n = 1) was prepared by the reac t ion of II with f l -chloropropionyl chloride, with subsequent boiling of the amide of /3-chloropropionic acid formed with a second mole of compound H in alcohol. The so-synthes ized monoamide VI was then converted by the method descr ibed above into the symmet r i ca l b i s -qua te rna ry salt:

DOI: 10.1007/BF00759875

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@article{Nikitskaya2004SynthesisAP, title={Synthesis and pharmacological study of symmetrical bis-quaternary salts related to 3-benzyl-3,9-diazabicyclo-[3.3.1]nnonane}, author={E. S. Nikitskaya and Boris Medvedev}, journal={Pharmaceutical Chemistry Journal}, year={2004}, volume={2}, pages={182-184} }