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Chemical synthesis of albendazole-sulphone

A technology of albendazole sulfone and chemical synthesis, applied in the direction of organic chemistry and the like, can solve the problems of many reaction steps, low purity, difficult purification and the like, and achieve the effects of avoiding loss, simple purification method and few reaction steps.

Inactive Publication Date: 2009-10-21
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) The reaction time is long, and the resulting product has low purity
(2) There are many reaction steps, the yield is low, and the consumption of reagents is large and toxic
(3) The reaction temperature is low, a large amount of sulfoxide is generated in the medium, and it is difficult to purify
During the reaction, substances are precipitated, and the raw materials are precipitated together, resulting in many impurities and low purity
(4) The purification method is complicated, and complex operations such as column chromatography are required

Method used

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  • Chemical synthesis of albendazole-sulphone
  • Chemical synthesis of albendazole-sulphone
  • Chemical synthesis of albendazole-sulphone

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Add 13.25 g of albendazole into a 500 ml four-necked flask equipped with a spherical condenser, then add 120 mL of glacial acetic acid, and stir in a 60°C water bath until dissolved. 12 mL of 30% hydrogen peroxide was added, and 12 mL of hydrogen peroxide was added at intervals of 6 h, and the reaction was continued for 6 h. The reaction mixture was obtained after the reaction was completed. Use 1mol·L -1 The sodium hydroxide solution neutralized the above reaction mixture to pH 5.0, filtered, and the filter cake was placed in an oven to dry. 13.07 g of crude albendazole sulfone were obtained.

[0029] 10.07g of crude albendazole sulfone was dissolved in a three-necked flask equipped with a spherical condenser, a water bath at 90°C, and 100mL of dimethyl sulfoxide solution (dimethyl sulfoxide: water=5: 1, V / V) was added and stirred until Dissolved, filtered while hot, the filtrate was slowly cooled at room temperature and then placed in a refrigerator at 4°C for 5 ho...

Embodiment 2

[0031] Add 13.25 g of albendazole to a 500 ml four-necked flask equipped with a spherical condenser, then add 120 ml of glacial acetic acid, and stir until dissolved in a water bath at 80°C. 18 mL of 30% hydrogen peroxide was added, and 18 mL of hydrogen peroxide was added at intervals of 5 h, and the reaction was continued for 5 h. The reaction mixture was obtained after the reaction was completed. Use 4mol·L -1 The sodium hydroxide solution neutralized the above reaction mixture to pH 6.5, filtered, and the filter cake was placed in an oven to dry. 14.03 g of crude albendazole sulfone were obtained.

[0032] 10.10g of albendazole sulfone crude product was dissolved in a three-necked flask equipped with a spherical condenser, 90 ° C water bath, 100 mL of dimethyl sulfoxide (dimethyl sulfoxide: water = 7: 1, V / V) solution was added and stirred until Dissolved, filtered while hot, the filtrate was slowly cooled at room temperature and then placed in a refrigerator at 4°C for...

Embodiment 3

[0034] Add 13.25g of albendazole to a 500ml four-necked flask equipped with a spherical condenser, add 120ml of glacial acetic acid, and stir in a 100°C water bath until dissolved. 24 mL of 30% hydrogen peroxide was added, and 24 mL of hydrogen peroxide was added at intervals of 6 h, and the reaction was continued for 6 h. The reaction mixture was obtained after the reaction was completed. Use 8mol·L -1 The sodium hydroxide solution neutralized the above reaction mixture to pH 7.0, filtered, and the filter cake was placed in an oven to dry. 14.18 g of crude albendazole sulfone were obtained.

[0035] Dissolve 10.05g crude albendazole sulfone in a three-necked flask equipped with a spherical condenser, water bath at 90°C, add 100mL dimethyl sulfoxide solution (dimethyl sulfoxide: water = 9: 1, V / V) and stir until Dissolved, filtered while hot, the filtrate was slowly cooled at room temperature and then placed in a refrigerator at 4°C for 5 hours, and filtered to obtain a rec...

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Abstract

The invention belongs to the field of synthesizing drug metabolites by chemical methods, in particular to a chemical synthesis method of albendazole sulfone, one of albendazole in vivo metabolites. Albendazole is used as a raw material, glacial acetic acid is used as a reaction medium, 30% hydrogen peroxide is used as an oxidizing agent, the amount of hydrogen peroxide is properly controlled, and albendazole is oxidized to obtain a crude albendazole sulfone, and the crude product of albendazole is recrystallized to prepare Albendazole sulfone was obtained with a purity of over 99.5%. In the invention, the conditions are easy to control, the route is simple, the solvent is easy to obtain, and the obtained product has high purity. The synthesis of albendazole sulfone not only provides a reference for the metabolism research and residue detection of albendazole, but also provides a reference for the synthesis of similar compounds.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of drug metabolites, in particular to a chemical synthesis method of albendazole sulfone, one of the metabolites of albendazole in vivo. Background technique [0002] After entering the body, albendazole is first metabolized to albendazole sulfoxide through the first-pass effect, and albendazole sulfoxide is then metabolized to albendazole sulfone, and finally metabolized to albendazole-2-aminosulfone. The main metabolic processes of albendazole in the body are: figure 1 shown. Albendazole sulfone is one of the main target metabolites in the detection of albendazole residues. Therefore, the preparation of albendazole sulfone is of great significance for the metabolism, pharmacology, toxicology and residue studies of albendazole. [0003] The reports on the preparation method of albendazole sulfone have the following relevant documents. Olivia et al reported that albendazole sulfone was prepar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/14
Inventor 袁宗辉刘振果陶燕飞王玉莲黄玲利陈冬梅彭大鹏戴梦红刘振利谢长清斯琴朝克图邱荣超刘志亮
Owner HUAZHONG AGRI UNIV
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