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A kind of preparation method of sugammadex sodium

A technology of sugammadex sodium and reagents, which is applied in the field of medicinal chemistry, can solve the problems of many impurities and low conversion rate, and achieve the effects of high purity, simple and safe reaction operation

Active Publication Date: 2022-08-05
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] Aiming at the problems of low conversion rate and many impurities generated in the current process of preparing sugammadex sodium, the purpose of the present invention is to provide a kind of simple operation, mild reaction conditions, high product yield, low production cost and high safety. Process for industrial production of sugammadex sodium with high and low pollution

Method used

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  • A kind of preparation method of sugammadex sodium
  • A kind of preparation method of sugammadex sodium
  • A kind of preparation method of sugammadex sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0075] Synthesis of sugammadex ethyl ester (intermediate I)

[0076] Under argon protection and shading conditions, dry γ-cyclodextrin (64.86g, 0.05mol), ethyl 3-mercaptopropionate (75.15g, 0.56mol), triphenylphosphine (230.82g, 0.88mol) were mixed Add it to anhydrous dimethyl sulfoxide (1000mL), after all the materials are dissolved, control the temperature to 0~5℃ and add diisopropyl azodicarboxylate (DIAD, 177.94g, 0.88mol) dropwise. The temperature is 30~35 ℃ and react for 8 hours, the detection reaction is completed, the reaction is finished, filtered, methanol / purified water (V:V=2:1, 2000mL) is added to the filtrate for crystallization, after the crystallization is completed, the filter cake is 35~40 After vacuum drying at °C, ethyl sugammadex (intermediate I) was obtained with a yield of 96% and a purity of 98.52%.

Embodiment 2

[0078] Synthesis of sugammadex ethyl ester (intermediate I)

[0079] Under argon protection and shading conditions, dry γ-cyclodextrin (64.86g, 0.05mol), ethyl 3-mercaptopropionate (64.41g, 0.48mol), triphenylphosphine (230.82g, 0.88mol) were mixed Add it into anhydrous dimethyl sulfoxide (1000mL), after all the materials are dissolved, add diethyl azodicarboxylate (DEAD, 153.14g, 0.88mol) dropwise at a temperature of 0 to 5°C. After the addition is complete, the temperature is controlled. 30~35 ℃ of reaction for 8 hours, detection reaction is completed, end the reaction, filter, add methanol / purified water (V:V=2:1, 2000mL) to the filtrate for crystallization, filter after the crystallization, filter cake 35~40 ℃ After drying in vacuo, ethyl sugammadex (intermediate I) was obtained with a yield of 91% and a purity of 96.34%.

Embodiment 3

[0081] Synthesis of sugammadex ethyl ester (intermediate I)

[0082] Under argon protection and shading conditions, dry γ-cyclodextrin (64.86g, 0.05mol), ethyl 3-mercaptopropionate (60.38g, 0.45mol), triphenylphosphine (230.82g, 0.88mol) Add it into anhydrous dimethyl sulfoxide (1000mL), after all the materials are dissolved, add diethyl azodicarboxylate (DEAD, 153.12g, 0.88mol) dropwise at a temperature of 0 to 5°C, after the dropwise addition is completed, the temperature is controlled 30~35 ℃ of reaction for 8 hours, detection reaction is completed, end the reaction, filter, add methanol / purified water (V:V=2:1, 2000mL) to the filtrate for crystallization, filter after the crystallization, filter cake 35~40 ℃ After vacuum drying, ethyl sugammadex (intermediate I) was obtained with a yield of 85% and a purity of 91.80%.

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Abstract

The invention discloses a preparation method of sugammadex sodium. The method uses γ-cyclodextrin as raw material, reacts with 3-mercaptopropionic acid substituted ester under the action of phosphine reagent and azo reagent to generate sugammadex; Hydrolysis in temperature and solvent to obtain the target product, sodium sugammadex. The method for preparing sodium sugammadex has mild reaction, omits the γ-cyclodextrin perhalogenation reaction process, is simple and time-saving in operation, has high yield of the obtained target product, and is suitable for industrial scale-up production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of sugammadex sodium. Background technique [0002] Sugammadex Sodium, chemical name is eight-6-all-deoxy-6-all (2-carboxyethyl) thio-γ-cyclodextrin sodium salt, CAS number: 343306-79-6, The specific structural formula is as follows: [0003] [0004] Sugammadex sodium is a new type of muscle relaxant reversal agent, which was first developed by Organon in the Netherlands. It is used to reverse the blocking effect of the commonly used neuromuscular blocking drugs rocuronium bromide or vecuronium bromide. Reversal of the effects of rocuronium bromide used in adults and routine reversal of the effects of rocuronium bromide used in children and adolescents (2-17 years). Sugammadex sodium is the first and only selective relaxant binding agent (SRBA), the first major drug development in the field of anesthetics in the past 20 years, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 鲍广龙彭祥龙
Owner LUNAN PHARMA GROUP CORPORATION
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