Synthesis of ioversol
AssigneeMallinckrodt Medical, Inc.
InventorsAllan R. Bailey, Sharad S. Sathe, Andre T. Spears, Richard C. Wisneski, Mills T. Kneller
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Abstract
The reduction of the O-alkyl isomer content of 5-[N-(2-acetoxyethyl)acetoxyacetamido]-N,N'-bis(2,3-diacetoxypropyl)-2,4,6 -triiodoisophthalamide to thereby reduce and/or eliminate the production of impurities comparatively more difficult to remove during the purification of crude ioversol.
Claims4
A process for the production of ioversol from 5-[N-(2-acetoxyethyl)acetoxyacetamido]-N,N'-bis(2,3-diacetoxypropyl)-2,4,6 -triiodoisophthalamide and an O-alkyl isomer of 5-[N-(2-acetoxyethyl) acetoxyacetamidol]-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalami de, comprising the steps of:
- a.) selectively hydrolyzing said O-alkyl isomer of 5-[N-(2-acetoxyethyl) acetoxyacetamido]-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamid e n 5-[N-(2-acetoxyethyl)-acetoyacetamido]-N,N'-bis(2,3-diacetoypropyl)-2,4,6- triiodoisophthalamide with water in a suitable solvent under selectively hydrolyzing conditions to produce 5-acetoxyacetamido-N,N'-bis(2,3-diacetoxypropyl)2,4,6-triiodoisophthalamid e in 5-[N-(2-acetoxyethyl) acetoxyacetamido]-N,N'-bis(2,3-diacetoxypropyl)-2,4,6-triiodoisophthalamid e;
- b.) acid hydrolyzing said 5-acetoxyacetamido-N,N'-bis(2,3-diacetoxypropyl)2,4,6-triiodoisophthalamid e and 5-[N-(2-acetoxyethyl)acetoxyacetamido]-N,N-bis(2,3-diacetoxypropyl)-2,4,6- triiodoisophthalamide under acid hydrolyzing conditions to produce ioversol and N,N'-bis-(2,3-dihydroxypropyl)-5-glycolamido-2,4,6-triiodoisophthalamide;
- and
- c.) purifying said ioversol produced to achieve purification thereof by removing said N,N'-bis-(2,3-dihydroxypropyl)5-glycamido-2,4,6-triiodoisophthalamide therefrom.
Dependencies are inferred from the claim text.