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Preparation method of hydroxychloroquine sulfate impurity

A technology of hydroxychloroquine sulfate and impurities, applied in the field of drug synthesis, can solve problems such as retinopathy, decreased corneal sensitivity, dangerous abnormal heart rhythm, etc., and achieve the effect of simple raw materials, easy access to raw materials, and simple synthesis operations

Pending Publication Date: 2022-04-22
SHENZHEN SUNGENING BIO-MEDICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the safety issues of hydroxychloroquine sulfate limit its use to a certain extent. Studies have shown that hydroxychloroquine may cause headaches, hair loss, decreased corneal sensitivity, and retinopathy; One of the drugs that can predispose people to very dangerous abnormal heart rhythms
The invention discloses a synthetic method of chloroquine hydroxysulfate impurity, which has not been reported at home and abroad

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Add 5-chloro-2-pentanone (6g, 50mmol), N-ethylbenzylamine (6.75g, 50mmol), potassium carbonate (13.8g, 100mmol) and potassium iodide (8.3g, 50mmol), acetonitrile (100ml); the mixture was reacted at 80°C for 12h, the reaction solution was filtered, the filter cake was washed with DCM (50ml), the filtrate was concentrated, and the residue was purified by column chromatography to obtain compound II.

[0024] (2) Add compound II (4.4g, 20mmol), benzylamine (2.5g, 23mmol), methanol (30ml) and sodium cyanoborohydride (1.26g, 20mmol) to a 100ml single-necked bottle, react at 75°C for 1h, and react The solution was concentrated, and the residue was purified by column chromatography to obtain compound III.

[0025] Compound III (5.0g, 16mmol) was dissolved in methanol (30ml), palladium carbon (500mg) was added, and reacted at 70°C for 24h in a hydrogen atmosphere. The reaction solution was concentrated to obtain oily compound IV.

[0026] Add 4,7-dichloroquinoline (2.5g, 12...

Embodiment 2

[0029] (1) Add 5-chloro-2-pentanone (6g, 50mmol), N-ethylbenzylamine (6.75g, 50mmol), potassium carbonate (13.8g, 100mmol) and potassium iodide (8.3g, 50mmol), acetonitrile (100ml); the mixture was reacted at 100°C for 12h, the reaction solution was filtered, the filter cake was washed with DCM (50ml), the filtrate was concentrated, and the residue was purified by column chromatography to obtain compound II.

[0030] (2) Add compound II (4.4g, 20mmol), benzylamine (2.5g, 23mmol), methanol (30ml) and sodium acetate borohydride (8.4g, 40mmol) to a 100ml single-necked bottle, react at 75°C for 1h, and the reaction solution After concentration, the residue was purified by column chromatography to obtain compound III.

[0031] Compound III (5.0 g, 16 mmol) was dissolved in isopropanol (30 ml), palladium hydroxide on carbon (500 mg) was added, and reacted at 25°C for 50 h in a hydrogen atmosphere. The reaction solution was concentrated to obtain oily compound IV.

[0032] Add 4,7-d...

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PUM

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Abstract

The invention discloses a preparation method of a hydroxychloroquine sulfate impurity, and belongs to the field of drug synthesis, the preparation method provided by the invention is reasonable in process design, strong in operability, high in yield and capable of realizing mass production. 5-chloro-2-pentanone is taken as a raw material, synthesis of the hydroxychloroquine sulfate impurity is realized through electrophilic reaction, reductive amination, hydrogenation deprotection and nucleophilic substitution reaction, the target impurity prepared by the method provides an important basis for scientific evaluation of quality and safety of hydroxychloroquine sulfate, and the method is suitable for industrial production. The method is of great significance to reasonable medication of hydroxychloroquine sulfate.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis and relates to a preparation method of hydroxychloroquine sulfate impurities. Background technique [0002] Hydroxychloroquine sulfate was successfully developed by Winthrop Company. It was first listed in the United States in 1956 and has been listed in France, Denmark, Japan, Germany, Finland and other countries and regions. U.S. FDA approved hydroxychloroquine sulfate tablets on May 29, 1998 for the treatment of lupus erythematosus and rheumatoid arthritis. Compared with other similar drugs, hydroxychloroquine sulfate has obvious safety advantages. It can not only improve the symptoms of arthritis in patients, but also has various effects such as anti-virus, anti-thrombosis, and hypoglycemia, and has a wide application prospect. [0003] However, the safety issues of hydroxychloroquine sulfate limit its use to a certain extent. Studies have shown that hydroxychloroquine may cause he...

Claims

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Application Information

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IPC IPC(8): C07D215/46
CPCC07D215/46
Inventor 周佳李方林孙坤杰
Owner SHENZHEN SUNGENING BIO-MEDICAL CO LTD
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