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Crystallization of iodixanol in isopropanol and methanol

A technology of iodixanol and isopropanol, used in organic chemistry, separation/purification of carboxylic acid amides, etc.

Active Publication Date: 2010-09-15
GE HEALTHCARE AS
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  • Abstract
  • Description
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Problems solved by technology

This is a challenge because even small amounts of water in the mother liquor of crystallization can significantly increase the solubility of iodixanol

Method used

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  • Crystallization of iodixanol in isopropanol and methanol

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Embodiment 1

[0039]Crude iodixanol dissolved in water (about 700 kg, HPLC purity 83-84%) was concentrated on a falling film evaporator, followed by conventional distillation to a viscous solution containing about 0.17-0.18 L water / kg Crude iodixanol. Methanol (1400 L) was added at reflux and the solution was inoculated with crystalline iodixanol (approximately 2-3 kg). Isopropanol (540 L) was added at a rate of 50-100 L / h under reflux. After 30 hours, more isopropanol (approximately 700 L) was added at the same low rate. A third portion of isopropanol may be added. At least 65 hours after inoculation and when the concentration of the mother liquor is 7.0 w / v% or less, the suspension is filtered on a pressure filter at 60° C. under a nitrogen pressure of up to 1 bar. The formed filter cake was washed with methanol at approximately 60°C (total 750 L). The HPLC purity of the crystals was 98.0-98.5%, and the crystallization yield was 85-90% relative to crude iodixanol.

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Abstract

The present invention relates to crystallization of iodixanol in isopropanol and methanol, concretely relates to a process for the manufacture of iodixanol by performing a crystallization process of the crude product in a solvent mixture comprising water, methanol and isopropanol. The crude product may be obtained in aqueous solution from dimerisation of 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-isophthalamide (''Compound A'').

Description

[0001] Cross-Referenced Related Applications [0002] This application claims the benefit of priority under 35 U.S.C. §119(e) of US Provisional Application No. 61 / 227,104, filed July 21, 2009, the entire disclosure of which is hereby incorporated by reference. technical field [0003] The present invention relates to iodixanol (1,3-bis(acetylamino)-N,N'-bis[3,5-bis(2,3-dihydroxypropylaminocarbonyl)-2,4,6-tri Production of iodophenyl]-2-hydroxypropane). Background technique [0004] Iodixanol is available under the brand name Visipaque TM Nonproprietary name of the chemical drug marketed under Non-Ionic X-ray Contrast Media. Visipaque TM is one of the most widely used reagents in diagnostic X-ray methods and is manufactured in large quantities. [0005] The manufacture of such non-ionic X-ray contrast agents involves the production of chemical substances (known as primary production) followed by formulation into pharmaceutical products (known as secondary production). Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/46C07C231/24
CPCC07C231/24C07C237/46
Inventor O·M·霍梅斯泰德
Owner GE HEALTHCARE AS
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