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Chemical synthesis of albendazole-sulfoxide

A technology for the chemical synthesis of albendazole sulfoxide, applied in the direction of organic chemistry, which can solve the problems of complex purification methods, many reaction steps, and harsh conditions, and achieve the effect of simple purification methods, fewer reaction steps, and reduced production

Inactive Publication Date: 2007-09-05
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) The reaction must be carried out at low temperature, and the conditions are relatively harsh
(2) The addition of solid oxidant is easy to introduce other impurities
(3) There are many reaction steps, the yield is low, and the consumption of reagents is large and toxic
(4) The purification method is complicated, and complex operations such as column chromatography and rotary evaporation are required
(5) Albendazole sulfoxide is insoluble in water and cannot be recrystallized with water

Method used

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  • Chemical synthesis of albendazole-sulfoxide
  • Chemical synthesis of albendazole-sulfoxide
  • Chemical synthesis of albendazole-sulfoxide

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 13.25g of albendazole into a 250mL four-neck flask, then add 70mL of glacial acetic acid, and stir at 15°C until dissolved. Slowly add 5.1 mL of 30% hydrogen peroxide dropwise with a dropping funnel, and react for 5 hours after the dropwise addition is completed. The end of the reaction is 1mol L -1 The reaction mixture was neutralized to pH 6.0 with a sodium hydroxide solution, filtered, and the filter cake was dried in an oven at 30°C. 13.76 g of crude albendazole sulfoxide was obtained.

[0026] Dissolve 10.02g of crude albendazole sulfoxide in a three-neck flask equipped with a spherical condenser, place in a 90°C water bath, add 100mL of 70% ethanol solution and stir until dissolved, suction filter while it is hot, slowly cool the filtrate to 4°C, and place it for 5~ Filter after 10h, the filter cake is rinsed with ethanol to obtain a recrystallization product of albendazole sulfoxide, and after the product is dried, the acetonitrile solution of N,N-dimethylf...

Embodiment 2

[0028] Add 13.25g of albendazole into a 250mL four-necked flask, add 70mL of glacial acetic acid, and stir in a 35°C water bath until dissolved. Slowly add 5.1 mL of 30% hydrogen peroxide dropwise with a dropping funnel, and react for 4 hours after the dropwise addition is completed. The reaction ends with 5mol L -1 The reaction mixture was neutralized to pH 6.5 with a sodium hydroxide solution, filtered, and the filter cake was dried in an oven at 40°C. 13.85 g of crude albendazole sulfoxide was obtained.

[0029] Dissolve 10.12g of crude albendazole sulfoxide in a three-neck flask equipped with a spherical condenser, place it in a water bath at 90°C, add 100mL of 85% ethanol solution and stir until dissolved, suction filter while it is hot, slowly cool the filtrate to 4°C, and place it for 5- After 10h, filter and wash the filter cake with ethanol to obtain a recrystallized product of albendazole sulfoxide. ) recrystallized twice, the filter cake was rinsed with N, N-dime...

Embodiment 3

[0031] Add 13.25g of albendazole into a 250mL four-necked flask, add 70mL of glacial acetic acid, and stir in a 50°C water bath until dissolved. Slowly add 5.1 mL of 30% hydrogen peroxide dropwise with a dropping funnel, and react for 3 hours after the dropwise addition is completed. The reaction ends with 8mol·L -1 The sodium hydroxide solution was neutralized to pH 7.0, filtered, and the filter cake was dried in an oven at 50°C. 13.71 g of crude albendazole sulfoxide was obtained.

[0032] Dissolve 10.07g of albendazole sulfoxide crude product in a three-neck flask equipped with a spherical condenser, place it in a water bath at 90°C, add 100mL of 90% ethanol solution and stir until dissolved, suction filter while it is hot, slowly cool the filtrate to 4°C, and place it for 5- After 10 hours, filter, and wash the filter cake with ethanol to obtain a recrystallized product of albendazole sulfoxide. After recrystallization twice, the filter cake was first washed with N,N-di...

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Abstract

A process for chemically synthesizing albendazole sulfoxide includes such steps as oxidizing reaction between albendazole, glacial acetic acid and H2O2 to obtain coarse albendazole sulfoxide, and recrystallizing.

Description

technical field [0001] The invention belongs to the field of synthesizing drug metabolites by chemical methods, in particular to a chemical synthesis method of albendazole sulfoxide, one of albendazole in vivo metabolites. Background technique [0002] Albendazole sulfoxide is a product of albendazole metabolized by the first-pass effect after entering the body, then metabolized into albendazole sulfone, and finally metabolized into albendazole-2-aminosulfone (see Figure 1). Albendazole sulfoxide is the main active ingredient of albendazole anthelmintic. The developmental effect test of albendazole sulfoxide on rats showed teratogenic toxicity (Committee for veterinary medical products Albendazole sulfoxide EMEA / MRL / 094 / 96-FINAL.June.1996). Therefore, albendazole sulfoxide is one of the target metabolites detected in the detection of albendazole residues. Therefore, the preparation of albendazole sulfoxide is of great significance for the study of the metabolism, pharmacol...

Claims

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Application Information

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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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