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Chemical synthesis of albendazole-2-amino-sulphone

A technology of albendazole and chemical synthesis, applied in the field of chemical synthesis of albendazole-2-aminosulfone, one of the metabolites of albendazole

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

[0004] There is no report about the chemical synthesis method of albendazole-2-aminosulfone both at home and abroad at present

Method used

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  • Chemical synthesis of albendazole-2-amino-sulphone
  • Chemical synthesis of albendazole-2-amino-sulphone
  • Chemical synthesis of albendazole-2-amino-sulphone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 13.24g of albendazole into a 500ml four-neck flask equipped with a spherical condenser, then add 120mL of glacial acetic acid, and stir in a 60°C water bath until dissolved. First add 12mL of 30% hydrogen peroxide, then add 12mL of 30% hydrogen peroxide at an interval of 6 hours, then react for 6 hours, and react for a total of 12 hours to obtain a reaction mixture A. In 2mol·L -1 Neutralize the above reaction mixture A to pH 6.0 with a sodium hydroxide solution, filter, and dry the filter cake in an oven at 75-90°C. 12.45 g of crude albendazole sulfone was obtained.

[0029] Dissolve 10.03g of crude albendazole sulfone in 200mL0.68mol L -1 Add the hydrochloric acid solution into a 500mL four-necked flask equipped with a spherical condenser, stir and heat to reflux for 48h to obtain the reaction mixture B. -1 Neutralize the above reaction mixture B to pH 6.8 with sodium hydroxide solution, put it in a refrigerator at 4°C for 4 hours, filter, and dry the filter ca...

Embodiment 2

[0032] Add 13.26g of albendazole into a 500ml four-necked flask equipped with a spherical condenser, then add 120mL of glacial acetic acid, and stir in a water bath at 80°C until dissolved. First add 12mL of 30% hydrogen peroxide, then add 12mL of 30% hydrogen peroxide at an interval of 5h, then react for 5h, and react for a total of 10h to obtain a reaction mixture A. In 2mol·L -1 Neutralize the above reaction mixture A to pH 6.5 with a sodium hydroxide solution, filter, and dry the filter cake in an oven at 75-90°C to obtain 12.39 g of crude albendazole sulfone.

[0033] Dissolve 10.07g of crude albendazole sulfone in 150mL3.4mol L -1 Add the hydrochloric acid solution into a 500mL four-necked flask equipped with a spherical condenser, stir and heat to reflux for 36h to obtain the reaction mixture B, and use 2mol L -1 Neutralize the above reaction mixture B to pH 7.0 with sodium hydroxide solution, put it in a refrigerator at 4°C for 6 hours, filter, and dry the filter cak...

Embodiment 3

[0036] Add 13.25g of albendazole into a 500ml four-neck flask equipped with a spherical condenser, then add 120mL of glacial acetic acid in a 100°C water bath, and stir until dissolved. First add 12mL of 30% hydrogen peroxide, then add 12mL of 30% hydrogen peroxide at an interval of 4 hours, then react for 4 hours, and react for 8 hours to obtain the reaction mixture A. In 2mol·L -1 Neutralize the above reaction mixture A to pH 7.0 with a sodium hydroxide solution, filter, and dry the filter cake in an oven at 75-90°C. 12.18 g of crude albendazole sulfone was obtained.

[0037] Dissolve 10.01g of crude albendazole sulfone in 100mL6.8mol L -1 Add the hydrochloric acid solution into a 500mL four-necked flask equipped with a spherical condenser, stir and heat to reflux for 24h to obtain the reaction mixture B, and use 2mol L -1 Neutralize the above reaction mixture B to pH 7.8 with sodium hydroxide solution, put it in a refrigerator at 4°C for 12 hours, filter, and dry the fil...

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Abstract

A process for chemically synthesizing albendazole-2-aminosulfone includes such steps as oxidizing reaction between albendazole, glacial acetic acid and H2O2 to obtain albendazole sulfone, reflux reaction in acid solution, regulating pH value to obtain coarse albendazole-2-aminosulfone, and recrystallizing.

Description

technical field [0001] The invention belongs to the technical field of synthesizing drug metabolites by chemical methods, in particular to a chemical synthesis method of albendazole-2-aminosulfone, one of albendazole metabolites in vivo. Background technique [0002] After entering the body, albendazole is first metabolized into albendazole sulfoxide through the first-pass effect, then into albendazole sulfone, and finally into albendazole-2-aminosulfone. The main metabolic process of albendazole in vivo is shown in Figure 1. [0003] In the evaluation of albendazole by the Food and Agriculture Organization of the United Nations (FAO), the Joint Expert Committee on Food Additives (JECFA) stipulates that the albendazole residue marker is albendazole-2-aminosulfone, that is, albendazole- 2-Aminosulfone is one of the main target metabolites in the detection of albendazole residues. At present, there is no commercial sale of albendazole-2-aminosulfone reference substance in Ch...

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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