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Iodixanol and synthesis method thereof

A technology of iodixanol and its synthetic method, which is applied in the field of polymers, can solve the problems of low yield and cumbersome post-treatment in reaction route 1, and achieve the effects of low reaction cost, high yield and high purity

Inactive Publication Date: 2018-09-14
川金药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In order to obtain high-purity iodixanol in the prior art, according to the method of reaction route 1, it is necessary to remove the compound of formula (5) by sacrificing a large amount of products, which will eventually lead to lower yield of reaction route 1 and cumbersome post-treatment, etc. series of questions

Method used

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  • Iodixanol and synthesis method thereof
  • Iodixanol and synthesis method thereof
  • Iodixanol and synthesis method thereof

Examples

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Embodiment 1

[0043] The synthetic method of iodixanol provided by the embodiments of the present invention comprises:

[0044] Step 1: Add 100g of 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-isophthalamide to 500ML clean four-port burnt product Add it into 300ml of acetic acid, stir and add 62g of acetone, 1.5g of concentrated sulfuric acid, stir and heat to 40°C, and react at this temperature for 12 hours to obtain the compound of formula (3);

[0045] Step 2: After the above reaction is completed, distill off the solvent under reduced pressure, then dissolve it with 300ml of anhydrous methanol, add 40.7g of 3-methylamino-1,2-propanediol and 1.5g of sodium methoxide, and heat under reflux for 6 hours. After the reaction is completed, cool down To below 30°C, add 180ml of 10N sodium hydroxide aqueous solution dropwise, after dripping, raise the temperature to 50°C for reaction 3, cool down to room temperature, adjust the pH to 2 with concentrated hydrochloric acid, concentrate ...

Embodiment 2

[0048] The synthetic method of iodixanol provided by the embodiments of the present invention comprises:

[0049] Step 1: Add 100g of 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-isophthalamide to 500ML clean four-port burnt product Add it to 300ml of acetic acid, stir and add 62g of acetone, 1.5g of concentrated sulfuric acid, stir and heat to 65°C, and react at this temperature for 12 hours to obtain the compound of formula (3);

[0050]Step 2: After the above reaction is completed, distill the solvent off under reduced pressure, then dissolve it with 300ml of anhydrous methanol, add 40.7g of 3-methylamino-1,2-propanediol, 1.5g of sodium methoxide, and heat to reflux for 6 hours. After the reaction is completed, cool down When the temperature is below 30°C, add 180ml of 10N sodium hydroxide aqueous solution dropwise, after dropping, raise the temperature to 65°C and react for 3-5 hours, then cool down to room temperature, adjust the pH to 3 with concentrated hydro...

Embodiment 3

[0053] The synthetic method of iodixanol provided by the embodiments of the present invention comprises:

[0054] Step 1: Add 100g of 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-isophthalamide to 500ML clean four-port burnt product Add to 300ml of acetic acid, stir and add 62g of acetone, 1.5g of concentrated sulfuric acid, stir and heat to 55°C, and react at this temperature for 12 hours to obtain the compound of formula (3);

[0055] Step 2: After the above reaction is completed, distill the solvent off under reduced pressure, then dissolve it with 300ml of anhydrous methanol, add 40.7g of 3-methylamino-1,2-propanediol, 1.5g of sodium methoxide, and heat to reflux for 6 hours. After the reaction is completed, cool down When the temperature is below 30°C, add 180ml of 10N sodium hydroxide aqueous solution dropwise, after the dropwise temperature rises to 55°C and reacts for 3-5 hours, then cools down to room temperature, adjusts the pH to 2.5 with concentrated hyd...

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Abstract

The invention belongs to the technical field of macromolecules, and discloses iodixanol and a synthesis method thereof. With a compound 5-acetamido-N, N'-bis(2, 3-dihydroxypropyl)-2, 4, 6-triiodo-isophthalamide as a raw material, an intermediate compound 5-acetamido-N, N'-bis(2, 3-dimethyl-1, 3-dioxolan-4-yl)methyl)-2, 4, 6-triiodo-isophthalamide is produced through addition of acetic acid and concentrated sulfuric acid. In allusion to the defects of the existing methods for preparing the iodixanol, through production of the novel intermediate compound, production of difficultly removed O-alkylated impurities during a reaction is avoided. The invention provides a method for synthesizing the iodixanol, which is more reasonable, higher in yield and higher in purity. By the method, the reaction cost is lower.

Description

technical field [0001] The invention belongs to the technical field of macromolecules, and in particular relates to a kind of iodixanol and a synthesis method thereof. Background technique [0002] Iodixanol (trade name ) is a non-ionic X-ray contrast agent developed by Nycomed Company of Norway, which was launched in 1993 and is being mass-produced. [0003] Iodixanol injection is directly injected into human blood vessels, and the dosage specification is high, which undoubtedly determines the high requirements for the quality of its raw materials, even higher than the pharmacopoeia standards; however, for commercial drugs, the high efficiency of its primary production Sex and economy are equally important, so the advanced nature of the chemical synthesis and purification process of iodixanol is very critical. [0004] The relevant preparation method of iodixanol reported in the literature is disclosed in the patent EP 0108638. [0005] Patent EP0108638 discloses the pr...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/46C07D317/28
CPCC07C231/12C07C237/46C07D317/28
Inventor 彭开金鲁灵江郑涛
Owner 川金药业有限公司
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