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Iomeprol preparation method

A molar ratio, triiodoisophthalic acid technology, applied in the preparation field of iomeprol, can solve the problems of being unsuitable for industrialized large-scale production, the methylation yield is not high, and the preparation cost is high, and achieves low cost and side reactions. Less, stable quality effect

Inactive Publication Date: 2013-07-17
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the methylation reaction in the last step of this synthesis method uses expensive methyl iodide, and the methylation yield is not high (77%), so the preparation cost of this method is higher, and it is not suitable for large-scale industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of 5-methylamino-2,4,6-triiodoisophthaloyl chloride:

[0029] In a three-necked flask equipped with a stirrer and a reflux condenser, 76g (0.133mol) of 5-methylamino-2,4,6-triiodoisophthalic acid was dissolved in 250mL (2.53mol) of ethyl acetate at room temperature , after stirring evenly, add 29 mL (0.4 mol) of thionyl chloride, then raise the temperature to the acid chloride reaction temperature of 50°C, and stir for 6 hours to complete the reaction. After ethyl acetate and thionyl chloride were evaporated under reduced pressure, 100 mL of ethyl acetate was added to the residue, the solvent was evaporated, washed with ice water, and dried to obtain 68.9 g of the product, with a yield of 84.9% (based on 5-methanol Amino-2,4,6-triiodoisophthalic acid), m.p.167~169℃.

Embodiment 2

[0031] Synthesis of 5-methylamino-2,4,6-triiodoisophthaloyl chloride:

[0032] Acyl chloride reaction temperature is 80 DEG C, reaction time is 3 hours, all the other operations are the same as embodiment 1.

Embodiment 3

[0034] Synthesis of 5-[N-methyl-2-chloroacetamido]-2,4,6-triiodoisophthaloyl chloride:

[0035]Add 36.6g (0.06mol) of 5-methylamino-2,4,6-triiodoisophthaloyl chloride and 80mL of N,N-dimethylacetamide into the reaction flask at room temperature, heat to 50°C in a water bath, After stirring and dissolving, cool down to 10°C and start to add 10.2g (0.09mol) of chloroacetyl chloride dropwise. After the dropwise addition, raise the temperature to 50°C, stir for 3 hours, cool to 10°C, and add 150mL of ice water dropwise. It was filtered, washed with ice water, and dried to obtain 38.7 g of the product, with a yield of 94% (calculated as 5-methylamino-2,4,6-triiodoisophthaloyl chloride), m.p.194~196°C.

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Abstract

An Iomeprol preparation method belongs to the technical field of non-ionic X ray contrast agent preparation. The chemical name of Iomeprol is 5-[N-methyl-2-ethoxyl amido]-N,N'-dual(2,3-dihydroxy propyl)-2,4,6-triiodide-1,3-benzenedicarboxamide. The preparation method comprises the following steps of: using 5- dimethylamino-2,4,6-triiodoisophthalic acid as a starting raw material, respectively performing a sulfonyl chlorination reaction, a chloroacctylation reaction, an amidation reaction and a hydroxylation reaction to prepared the Iomeprol product. The medicament is a new-generation non-ionic X ray contrast agent with excellent security and contrast effect. The preparation method has advantages of stable quality, high yield and low cost, and is applicable to be used to realize industrialproduction.

Description

technical field [0001] The invention discloses a preparation method of iomeprol, which belongs to the technical field of non-ionic X-ray contrast agent preparation. The chemical name of iomeprol is 5-[N-methyl-2-hydroxyacetamido]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1 , 3-phthalamide, is a new generation non-ionic X-ray contrast agent showing excellent safety and contrast effect. Background technique [0002] Chemical name of iomeprol: 5-[N-methyl-2-glycolamino]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1 , 3-phthalamide, the English common name of this compound is Iomeprol, and the trade name of its preparation is Iomiron, structural formula (I): [0003] [0004] Iomeprol is a non-ionic X-ray contrast agent developed by Bracco Company in Italy. It was approved for marketing in May 1993 in Italy and December 1992 in the United Kingdom. Iomeprol is a nonionic compound with a chemically stable hydrophilic group introduced into the triiodobenzene ring, and is ea...

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王洪勇
Owner JIANGSU INST OF NUCLEAR MEDICINE