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Synthetic method of iopamidol impurity C

A synthesis method and a technology for iopamidol, applied in the field of medicine, can solve the problems of affecting the quality of iopamidol products, difficult to remove, etc., and achieve the effects of simple solvent category and easy separation and purification

Inactive Publication Date: 2016-02-03
ZHEJIANG HAIZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Since the impurity C has similar chemical properties to the iopamidol product, it is difficult to completely remove it in the subsequent purification process, which will eventually affect the quality of the iopamidol product
After searching, there is no synthetic method of iopamidol impurity C reported in the literature, therefore, providing a synthetic method of iopamidol impurity C is of great significance to the preparation of impurity standards and the quality control of iopamidol products

Method used

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  • Synthetic method of iopamidol impurity C
  • Synthetic method of iopamidol impurity C
  • Synthetic method of iopamidol impurity C

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) 5-[(acetyl)amino]-1,3-dibenzoyl chloride shown in the synthetic formula III

[0024] According to the mass volume ratio of 5-amino-1,3-dibenzoyl chloride and N,N-dimethylacetamide is 1g:1.5mL, put 23.8g of 5-amino-1,3-dibenzoyl chloride in 1000mL In three-necked reaction flask, N 2 Add 36mL of N,N-dimethylacetamide dried over 4A molecular sieves under protection, stir to dissolve, cool down to 0-5°C in an ice bath, slowly add 4.1g of acetyl chloride, 5-amino-1,3-benzidine The molar ratio of acid chloride to acetyl chloride is 1:1.3. During the dropwise addition, the temperature of the solution is kept below 5°C. After the dropwise addition, the temperature is naturally raised to 15-20°C for reaction. TLC detection and tracking (developing agent is tetrahydrofuran: dichloromethane=1 : 1), after reacting for 15 hours, the raw material disappeared substantially, and 72mL of dichloromethane was dripped into the solution, and then washed 4 times with water successively,...

Embodiment 2

[0028] (1) 5-[(acetyl)amino]-1,3-phthaloyl chloride shown in synthetic formula III

[0029] According to the mass volume ratio of 5-amino-1,3-dibenzoyl chloride and N,N-dimethylacetamide is 1g:3mL, put 20g of 5-amino-1,3-dibenzoyl chloride in 1000mL three-port reaction bottle, N 2 Add 60mL of N,N-dimethylacetamide dried with 4A molecular sieves under protection, stir to dissolve, cool down to 0-5°C in an ice bath, slowly add 3.4g of acetyl chloride, 5-amino-1,3-benzidine The molar ratio of acid chloride to acetyl chloride is 1:1.3. During the dropwise addition, the temperature of the solution is kept below 5°C. After the dropwise addition, the temperature is naturally raised to 15-20°C for reaction. TLC detection and tracking (developing agent is tetrahydrofuran: dichloromethane=1 : 1), after reacting for 13 hours, the raw material disappeared substantially. In the solution, drip 120mL of dichloromethane, then wash with water 4 times successively, each 100mL, saturated saline...

Embodiment 3

[0033] Synthesis of impurity C according to the method of Example 1, the difference is that triethylamine is replaced by diisopropylethylamine, other steps are the same as in Example 1, 9.5g of impurity C is obtained, the yield is 70.8%, and the purity is high as determined by HPLC at 95%.

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Abstract

The invention relates to a synthetic method of a non-ionic X-radiographic contrast agent iopamidol impurity C. according to the synthetic method, 5-amino-1,3-dibenzoyl dichloride is used as a starting material. The iopamidol impurity C can provides a qualified reference substance for quality control of iopamidol.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a synthesis method of impurity C in iopamidol. Background technique [0002] Iopamidol is one of the non-ionic X-ray contrast agents widely used at present, and its impurity C is required to be controlled within 0.1% in the European Pharmacopoeia and the United States Pharmacopoeia, and its structure is as follows: [0003] [0004] Because impurity C and iopamidol product have relatively similar chemical properties, therefore, it is difficult to completely remove in the follow-up purification process, which will eventually affect the quality of iopamidol product. After searching, there is no report on the synthesis method of iopamidol impurity C. Therefore, providing a synthesis method of iopamidol impurity C is of great significance to the preparation of impurity standards and the quality control of iopamidol products. Contents of the invention [0005] The object of t...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C237/46
Inventor 宋卫怀哲明马刚陈胜叶新权蒋冬华
Owner ZHEJIANG HAIZHOU PHARMA CO LTD
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