- ENVIRONMENT-FRIEND PROCESS FOR THE SYNTHESIS OF QUATERNARY AMMONIO-STEROΙDS
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The invention relates to a new, environment-friend process for the synthesis of the known 4,4'-[3α,17β-bis(acetoxy)-5α-androstane-2β,l6β-diyl]-bis(l,l-dimethyl-ρiρerazinium) dibromide of formula (I) (from now on pipecuronium bromide) and l-[3α,17β-bis(acetoxy)-2β-(l-piperidinyl)-5α-androstane-16β-yl]-l-methyl-piperidinium bromide of formula (II) (from now on vecuronium bromide). Furthermore the invention relates to the new intermediates of formula (III) and formula (IV) of the process, wherein the meaning of X is benzenesulfonate - in given case para-substituted with a methyl or a nitro group or a bromine atom - methanesulfonate, ethanesulfonate or trifluoromethanesulfonate ion.
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Page/Page column 13-14
(2008/06/13)
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- Synthesis of 2β,16β-bis-(4'-dimethyl-1'-piperazino)-3α,17β-diacetoxy-5α-androstane dibromide and related compounds
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A series of bisquaternary ammonio steroids having androstane skeletons have been prepared some of which possessed high neuromuscular blocking activity. One of the series 2β,16β-bis-(4'-dimethyl-1'-piperazino)-3α,17β-diacetoxy-5α-androstane-dibromide (9, pipecurium bromide, Arduan) has proved to be a clinically useful agent of medium duration of action without side effects. The preparation of these ammonio steroids and structure-activity relationships within the series are described. The structure of 9 and related compounds was elucidated by spectrometric methods Ir, NMR and MS.
- Tuba
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p. 342 - 346
(2007/10/02)
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