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Preparation method of sugammadex sodium

A technology of sugammadex sodium and a reagent, which is applied in the field of medicinal chemistry, can solve the problems of many impurities and low conversion rate, and achieves the effects of high purity, simple reaction operation and low production cost.

Active Publication Date: 2020-08-11
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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  • Preparation method of sugammadex sodium
  • Preparation method of sugammadex sodium
  • Preparation method of sugammadex sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0075] Synthesis of Ethyl Sugammadex Gluconate (Intermediate I)

[0076] Under argon protection and light-shielding conditions, dry γ-cyclodextrin (64.86g, 0.05mol), ethyl 3-mercaptopropionate (75.15g, 0.56mol), triphenylphosphine (230.82g, 0.88mol) Add it into anhydrous dimethyl sulfoxide (1000mL), after the material is completely dissolved, add diisopropyl azodicarboxylate (DIAD, 177.94g, 0.88mol) dropwise at a temperature of 0-5°C. React at 30-35°C for 8 hours, detect the completion of the reaction, end the reaction, filter, add methanol / purified water (V:V=2:1, 2000mL) to the filtrate to crystallize, filter after the crystallization, the filter cake is 35-40 After vacuum drying at °C, ethyl sugammadex gluconate (intermediate I) was obtained with a yield of 96% and a purity of 98.52%.

Embodiment 2

[0078] Synthesis of Ethyl Sugammadex Gluconate (Intermediate I)

[0079] Under argon protection and light-shielding conditions, dry γ-cyclodextrin (64.86g, 0.05mol), ethyl 3-mercaptopropionate (64.41g, 0.48mol), triphenylphosphine (230.82g, 0.88mol) Add it into anhydrous dimethyl sulfoxide (1000mL), after the material is completely dissolved, add diethyl azodicarboxylate (DEAD, 153.14g, 0.88mol) dropwise under temperature control at 0-5°C, after the addition is complete, control the temperature React at 30-35°C for 8 hours, detect the completion of the reaction, end the reaction, filter, add methanol / purified water (V:V=2:1, 2000mL) to the filtrate to crystallize, filter after the crystallization, filter cake 35-40°C After vacuum drying, ethyl sugammadex gluconate (intermediate I) was obtained with a yield of 91% and a purity of 96.34%.

Embodiment 3

[0081] Synthesis of Ethyl Sugammadex Gluconate (Intermediate I)

[0082] Under argon protection and light-shielding 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 the material is completely dissolved, add diethyl azodicarboxylate (DEAD, 153.12g, 0.88mol) dropwise at a temperature of 0-5°C, after the addition is complete, React at 30-35°C for 8 hours, detect the completion of the reaction, end the reaction, filter, add methanol / purified water (V:V=2:1, 2000mL) to the filtrate to crystallize, filter after the crystallization, filter cake 35-40°C Sugammadex ethyl gluconate (intermediate I) was obtained after vacuum drying 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 comprises the following steps: taking gamma-cyclodextrin as a raw material, reacting gamma-cyclodextrin with 3-mercaptopropionic acid substituted ester under the action of a phosphine reagent and an azo reagent to generate sugammadex ester; and hydrolyzing the sugammadex ester and an alkaline reagent in a solvent at a certain temperature to obtain the target product sugammadex sodium. The preparation method of sugammadex sodium is mild in reaction, a gamma-cyclodextrin perhalogenation reaction process is omitted, theoperation is simple, convenient and time-saving, the yield of the obtained target product is high, and the method 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, the chemical name is octa-6-perdeoxy-6-full(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 routinely used neuromuscular blocking drugs rocuronium or vecuronium. Reverse the effect of rocuronium bromide used by adults, routinely reverse the effect of rocuronium bromide used by children and adolescents (2-17 years old). Sugammadex sodium is the first and only selective relaxant binding agent (selective relaxant binding agent, SRBA), which is the first major drug development in the field of anesthetics in...

Claims

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Application Information

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