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Preparation of N-arylmethyl aziridine derivatives, 1,4,7,10-tetraazacyclododecane derivatives obtained therefrom and N-arylmethyl-ethanol-amine sulphonate esters as intermediates
   
Document Number
US Patent 6048979
Issued Date
April 11, 2000
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Abstract
Aziridines may be subjected to a cyclooligomerization reaction to produce polyazacycloalkane compounds useful for example in the preparation of chelating agents for use in diagnostic imaging contrast agents. N-benzyl-aziridine in particular is useful as it can be cyclotetramerized and debenzylated to yield cyclen, a key intermediate in chelating agent preparation. The invention provides a particularly attractive route to production of N-benzyl and other N-arylmethyl aziridines of formula (I) where each R.sub.1 is independently hydrogen or a group AR and Ar is an optionally substituted phenyl group. The process comprises reacting a purified N-arylmethylethanolaminesulphonate ester with a base. N-arylmethyl-ethanolamine sulphonate ester of the formula R'NHCH.sub.2 CH.sub.2 OSO.sub.3 H, wherein the N-arylmethyl group R' is an N-(bisarylmethyl) or N-(triarylmethyl) group, as intermediates. In a further aspect, the invention provides compounds of formula (II) ##STR1## where Ar and R.sub.1 are as hereinabove defined and at least two differing ArCHR.sub.21 moieties are present.
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Preparation of N-arylmethyl aziridine derivatives, 1,4,7,10-tetraazacyclododecane derivatives obtained therefrom and N-arylmethyl-ethanol-amine sulphonate esters as intermediates - US Patent 6048979 Drawing
Drawing from US Patent 6048979
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Number of Claims:
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Published
April 11, 2000
Application Number
08/894,790
Filed
December 2, 1997
US Classification
540/474   548/955 548/968 548/969
Int'l Classification
A61K   49/00   (20060101)   A61K   49/06   (20060101)   C07C   303/44   (20060101)   C07C   303/00   (20060101)   C07D   257/00   (20060101)   C07D   255/00   (20060101)   C07D   259/00   (20060101)   C07D   257/02   (20060101)   C07D   203/00   (20060101)   C07D   203/08   (20060101)   C07C   305/06   (20060101)   C07C   305/00   (20060101)  
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Parent Case
This application is a 371 of PCT/GB96/00552, filed Mar. 8, 1996.
Priority Data
Mar 10, 1995 [GB] 9504921 Dec 28, 1995 [GB] 9526616
USPTO Field of Search
548/955   548/968   548/969   540/474  
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Description
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