Preparation method of ioxaglic alcohol

A technology of iodixanol and triiodoisophthalamide, which is applied in the field of preparation of iodixanol, can solve the problems of long and expensive reaction steps, achieve simple operation, control and side reactions, and shorten reaction time Effect

Active Publication Date: 2009-09-09
ZHEJIANG HAIZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Though it can avoid the difficult last step dimerization condensation reaction in the above-mentioned 2 kinds of processes, because this operational route starts from 5-nitroisophthalic acid, it needs to react through eight steps, and the reaction steps are too long, and Premature introduction of iodine atoms in the synthetic sequence, iodine being the most expensive reagent in the process

Method used

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  • Preparation method of ioxaglic alcohol
  • Preparation method of ioxaglic alcohol
  • Preparation method of ioxaglic alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1—8

[0029] Embodiment 1-8 , iodixanol preparation

[0030] As shown in Table 1, take 0.6mol solid sodium hydroxide, dissolve it in 400ml solvent, heat up to 45°C, add 0.501mol compound 5-acetamido-N,N'-bis(2,3-dihydroxypropyl )-2,4,6-triiodoisophthalamide (hereinafter referred to as "compound A").

[0031] After all the solid raw materials are dissolved, the temperature is lowered to below 15°C, and 0.167mol of dimerization reagent containing the general structural formula (I) is added, and after stirring and reacting for 2 hours below 10°C, the temperature is raised to room temperature for reaction; Take a sample in 2 hours, the sample detects the iodixanol content wherein with the HPLC method, plots the iodixanol content with the reaction time (embodiment 6), the result is as follows image 3 shown.

[0032] Depend on image 3 It can be seen from the results that after reacting for about 18-20 hours, the content of iodixanol in the reaction mixture no longer significantly i...

Embodiment 9—20

[0036] Embodiment 9-20 , iodixanol preparation

[0037] As shown in Table 1, take 0.6 mol of solid sodium hydroxide, dissolve it in 400 ml of solvent, heat up to 45° C., and add 0.501 mol of compound A (recovered raw material + fresh raw material).

[0038] After all the solid raw materials are dissolved, the temperature is lowered to below 10°C, and 0.167mol of a dimerization reagent containing the general structural formula (II) is added, stirred and reacted at below 15°C for 2 hours, then warmed up to room temperature for reaction; Take a sample in 2 hours, the sample detects the iodixanol content wherein with the HPLC method, plots the iodixanol content with the reaction time (embodiment 12,17), the result is as follows image 3 shown.

[0039] Depend on image 3 The results can be seen that after about 18-20 hours of reaction, the content of iodixanol in the reaction mixture no longer significantly increases, thus it can be determined that the reaction time is 18-20 hou...

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Abstract

This invention relates a method that use dimeric 5 - azodermine - N, N - double ( 2, 3 - dioxy- propyl) - 2 and 4, 6 - triiodo meta xyylene diamine amide to prepare iodixanol. The characteristic is it takes reagent has following structure general expression (1) or (2) as dimeric reagent. After the dimeric step, generated iodixanol is extracted from hybrid for purification, and the rest not reactant raw material could be recovered. The iodixanol produced by this method not only be able to control and decrease subsidiary reaction effectively, advance reaction positive direction ongoing degree and greatly short reaction time, but also be able to recovery utilize not reactant raw material.

Description

technical field [0001] The invention belongs to the field of chemical medicines, and in particular relates to a preparation method of iodixanol. Background technique [0002] Iodixanol (chemical name: 1,3-bis(acetamido)-N,N'-bis[3,5-bis(2,3-dihydroxypropylaminocarbonyl)-2,4,6 -triiodophenyl]-2-hydroxypropane) is a kind of triiodobenzene ring non-ionic X-ray contrast agent, developed by Norway Nycomed company and listed in 1993, the trade name is Visipaque (Visipaque), It is currently being produced in large quantities, and some preparation methods are well known, but the processes of these preparation methods are multi-step, so it is very important to optimize these processes from the aspects of economy and environmental protection. [0003] The preparation method of iodixanol mainly contains three kinds (EP108638, WO0047549 and CN1340042), and they all start from 5-nitroisophthalic acid: [0004] The technological route that the first kind of technical process (NO161358) ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/46C07C231/12
CPCY02P20/582
Inventor 史命锋
Owner ZHEJIANG HAIZHOU PHARMA CO LTD
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