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Improved process for synthesizing ioversol

A synthesis method and technology of ioversol are applied in the improved synthesis field of ioversol, can solve the problems such as inability to meet the needs of industrial production, difficulty in recovering solvent, etc., and achieve the effects of low cost, easy recovery of solvent and mild reaction conditions

Inactive Publication Date: 2007-10-24
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using this purification method, although the amount of recrystallization solvent has been greatly reduced compared with the use of n-butanol alone, it still needs two recrystallizations, and after using a mixed solvent, it is relatively difficult to recover the solvent
[0009] Therefore, the above process cannot meet the needs of industrial production.

Method used

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  • Improved process for synthesizing ioversol
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Embodiment 1

[0019] The synthesis of embodiment 1 ioversol:

[0020] In a three-necked flask equipped with a stirrer and a reflux condenser, add 152.6 g (0.2 mol) of 5-hydroxyacetamido-N, N'-bis(2,3-dihydroxypropyl)-2,4 , 6-triiodo-1,3-benzenedicarboxamide, 24g (0.6moL) sodium hydroxide and 600mL water, after stirring and dissolving, add 200mL acetonitrile, stir for 5 minutes, then add 96.6g (1.2moL) 2 -chloroethanol, then warming up to 50°C, stirring for 6 hours to stop the reaction. Neutralize with dilute hydrochloric acid, then distill off the solvent under reduced pressure. The residue was dissolved in 300mL of methanol, filtered, the filtrate was evaporated to remove methanol, and the residue was dissolved in 500mL of water. The solution was treated with 732 cation exchange resin and 717 anion exchange resin to remove cations and anions in the solution. The solvent was evaporated under reduced pressure to obtain a residue, which was dried in vacuo to obtain 155 g of a white solid (...

Embodiment 2

[0022] The synthesis of embodiment 2 ioversol:

[0023] In a three-necked flask equipped with a stirrer and a reflux condenser, add 152.6 g (0.2 mol) of 5-hydroxyacetamido-N, N'-bis(2,3-dihydroxypropyl)-2,4 , 6-triiodo-1,3-benzenedicarboxamide, 16g (0.4moL) sodium hydroxide and 600mL water, after stirring and dissolving, add 200mL acetonitrile, stir for 5 minutes, then add 64.4g (0.8moL) 2 -chloroethanol, then warming up to 30°C, stirring for 4 hours to stop the reaction. Neutralize with dilute hydrochloric acid, then distill off the solvent under reduced pressure. The residue was dissolved in 300mL of methanol, filtered, the filtrate was evaporated to remove methanol, and the residue was dissolved in 500mL of water. The solution was treated with 732 cation exchange resin and 717 anion exchange resin to remove cations and anions in the solution. The solvent was evaporated under reduced pressure to obtain a residue, which was dried in vacuo to obtain 145 g of a white solid (...

Embodiment 3

[0025] The synthesis of embodiment 3 ioversol:

[0026] In a three-necked flask equipped with a stirrer and a reflux condenser, add 152.6 g (0.2 mol) of 5-hydroxyacetamido-N, N'-bis(2,3-dihydroxypropyl)-2,4 , 6-triiodo-1,3-benzenedicarboxamide, 32g (0.8moL) sodium hydroxide and 600mL water, after stirring and dissolving, add 200mL acetonitrile, stir for 5 minutes, then add 128.8g (1.6moL) 2 -chloroethanol, then warming up to 70°C, stirring for 8 hours to stop the reaction. Neutralize with dilute hydrochloric acid, then distill off the solvent under reduced pressure. The residue was dissolved in 300mL of methanol, filtered, the filtrate was evaporated to remove methanol, and the residue was dissolved in 500mL of water. The solution was treated with 732 cation exchange resin and 717 anion exchange resin to remove cations and anions in the solution. The solvent was distilled off under reduced pressure to obtain a residue, which was dried in vacuo to obtain 148 g of a white sol...

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Abstract

The invention provides an improved method for synthesizing Ioversol, belonging to technology preparing non-ionic X contrast agent. The invention employs 5- hydroxyethyl amido- N, N' - (2,3-dihydroxy propyl)- 2, 4, 6- triiodide-1, 3- benezene diformamide and 2- chlorethanol to proceed nitrogen alkylation reaction in mixing solution of caustic soda and acetonitrile, neutralizing, desalting and desalting reacting solution, re-crystallizing with methyl glycol single dimethyl ether, and getting Ioversol. The invention is characterized by soft reacting condition, short reaction time, and stable quality, low cost and suitable for industrialized production.

Description

technical field [0001] The invention relates to an improved synthesis method of ioversol. The compound is a non-ionic X-ray contrast agent, which is suitable for CT examination, arteriovenous contrast and urography, etc., and belongs to the preparation technology of the non-ionic X-ray contrast agent. Background technique [0002] Ioversol, the chemical name is N,N'-bis(2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)-glycolamide]-2,4,6-tri Iodine-1,3-phthalamide, the trade name of its preparation is Anxili, structural formula (I): [0003] [0004] Ioversol has the advantages of large water solubility, low viscosity, low osmotic pressure, and low incidence of adverse reactions. Its preparation, Ioversol Injection, is widely used clinically for cardiovascular angiography and intravenous digital subtraction angiography. [0005] U.S. Patent No. 4,396,598 discloses a synthetic technique of ioversol, the last step reaction of which is 5-hydroxyacetamido-N, N'-bis(2,3-dihydroxypro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/46C07C231/12
Inventor 邹霈罗世能谢敏浩刘娅灵何拥军
Owner JIANGSU INST OF NUCLEAR MEDICINE
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