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Improved process for synthesizing ioversol

A synthesis method and a technology for ioversol, applied in the improved ioversol synthesis field, can solve problems such as inability to meet the needs of industrial production, difficulty in recovering a solvent, and achieve the effects of low cost, easy solvent recovery, and improved yield

Inactive Publication Date: 2006-12-27
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
  • Improved process for synthesizing ioversol

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Experimental program
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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, 152.6g (0.2mol) of 5-hydroxyacetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4 was added at room temperature , 6-triiodo-1,3-benzenedicarboxamide, 24g (0.6moL) sodium hydroxide and 600mL water, after stirring and dissolving, add 200mL acetonitrile, after stirring for 5 minutes, add 96.6g (1.2moL) 2 - Chloroethanol, then the temperature was raised to 50°C, and the reaction was stopped after stirring for 6 hours. After neutralization with dilute hydrochloric acid, the solvent was evaporated under reduced pressure. The residue was dissolved in 300 mL of methanol, filtered, the filtrate was evaporated to remove methanol, and the residue was dissolved in 500 mL of water. The solution was treated with 732 cation exchange resin and 717 anion exchange resin, respectively, to remove cations and anions from the solution. The solvent was evaporated under reduced pre...

Embodiment 2

[0022] The synthesis of embodiment 2 ioversol:

[0023] In a three-necked flask equipped with a stirrer and a reflux condenser, 152.6g (0.2mol) of 5-hydroxyacetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4 was added at room temperature , 6-triiodo-1,3-benzenedicarboxamide, 16g (0.4moL) sodium hydroxide and 600mL water, after stirring and dissolving, add 200mL acetonitrile, after stirring for 5 minutes, add 64.4g (0.8moL) 2 - Chloroethanol, then the temperature was raised to 30°C, and the reaction was stopped after stirring for 4 hours. After neutralization with dilute hydrochloric acid, the solvent was evaporated under reduced pressure. The residue was dissolved in 300 mL of methanol, filtered, the filtrate was evaporated to remove methanol, and the residue was dissolved in 500 mL of water. The solution was treated with 732 cation exchange resin and 717 anion exchange resin, respectively, to remove cations and anions from the solution. The solvent was evaporated under reduced pre...

Embodiment 3

[0025] The synthesis of embodiment 3 ioversol:

[0026] In a three-necked flask equipped with a stirrer and a reflux condenser, 152.6g (0.2mol) of 5-hydroxyacetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4 was added at room temperature , 6-triiodo-1,3-benzenedicarboxamide, 32g (0.8moL) sodium hydroxide and 600mL water, after stirring and dissolving, add 200mL acetonitrile, after stirring for 5 minutes, add 128.8g (1.6moL)2 - Chloroethanol, then the temperature was raised to 70°C, and the reaction was stopped after stirring for 8 hours. After neutralization with dilute hydrochloric acid, the solvent was evaporated under reduced pressure. The residue was dissolved in 300 mL of methanol, filtered, the filtrate was evaporated to remove methanol, and the residue was dissolved in 500 mL of water. The solution was treated with 732 cation exchange resin and 717 anion exchange resin, respectively, to remove cations and anions from the solution. The solvent was evaporated under reduced pre...

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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, suitable for CT examination, arteriovenous contrast and urography, etc., and belongs to the non-ionic X-ray contrast agent preparation technology. Background technique [0002] Ioversol, chemical name is N,N'-bis(2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)-hydroxyacetamido]-2,4,6-tri Iodine-1,3-benzenedicarboxamide, the trade name of its preparation is Anxili, and its structural formula (I): [0003] [0004] Ioversol has the advantages of high water solubility, low viscosity, low osmotic pressure, and low incidence of adverse reactions. Its preparation, ioversol injection, is widely used clinically for cardiovascular angiography, intravenous digital subtraction angiography, etc. [0005] U.S. patent US4396598 discloses a synthesis process of ioversol. The last step of the process is to use 5-hydroxyacetamido-N,N'-bis(2,3-dihydroxypro...

Claims

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Application Information

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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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