Preparation method for green and environmentally friendly sugammadex sodium

A technology of sugammadex sodium, green and environmental protection is applied in the field of preparation of sugammadex sodium, which can solve the problems of increasing the difficulty of industrial application, cumbersome processing process, etc., and achieves the effects of good application prospect, high product purity and mild reaction conditions.

Inactive Publication Date: 2018-12-04
HEFEI BOSIKC PHARMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the processing process is relatively cumbersome, and the ion resin needs to be processed, which increases the difficulty of industrial application.

Method used

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  • Preparation method for green and environmentally friendly sugammadex sodium
  • Preparation method for green and environmentally friendly sugammadex sodium
  • Preparation method for green and environmentally friendly sugammadex sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of Crude Sugammadex Sodium

[0041] Add sodium hydroxide (23.5g, 588mmol) into the reaction flask, add 150ml water to dissolve completely; add dropwise 3-mercaptopropionic acid aqueous solution (39.0g, 368mmol, dissolve in 80ml water) to the flask under stirring, add 6-deoxy- 6-Periodo-γ-cyclodextrin (40g, 18.4mmol), after adding, raise the temperature to 100°C, and react for 4h; after the reaction, cool to room temperature, add 700mL DMF to crystallize while stirring, filter, collect the solid, and dry in vacuo Obtain off-white solid 45g, purity is 94.83% (see attached Figure 3-4 ).

Embodiment 2

[0043] Purification of sugammadex sodium

[0044] Under the protection of nitrogen, take 40g of crude sugammadex sodium, dissolve it in a mixed solution of 100ml of water and 600ml of ethanol, stir and raise the temperature to 40°C, then cool down to room temperature, a white solid precipitates out, and is filtered by suction to obtain 35g of a white solid; repeat the above During the recrystallization process, 32g of white solid was obtained; the solid was detected by HPLC, except that the impurity with retention time RRT=0.87 was relatively large, and all other impurities were less than 0.1% (see attached Figure 5-6 ).

[0045] Put 30 g of sugammadex sodium after recrystallization and purification into a beaker, add 100 ml of purified water into the beaker and stir to dissolve completely. 300g of neutral alumina was added to the glass chromatography column, and the crude sugammadex sodium solution was loaded into the chromatography column. The chromatographic column was e...

Embodiment 3

[0047] Purification of sugammadex sodium

[0048]Put 35g of sugammadex sodium crude product into a beaker, add 120ml of purified water into the beaker and stir to dissolve completely; add 350g of neutral alumina to the glass chromatography column, and load the sugammadex sodium crude product solution onto the chromatography column Medium; the chromatography column was eluted with 2L of purified water, and the eluent was concentrated to dryness under reduced pressure to obtain 30 g of white solid; the solid was detected by HPLC, except for the impurity with retention time RRT=0.87 was removed, the rest of the impurities were relatively large (see attached Figure 9-10 ).

[0049] Under the protection of nitrogen, take 30 g of the above white solid, dissolve it in a mixed solution of 90 ml of water and 225 ml of DMF, stir to raise the temperature to 85 ° C, and then cool it down to room temperature, a white solid is precipitated, filtered by suction to obtain 28 g of a white so...

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Abstract

The invention belongs to the field of pharmacy, and especially relates to a preparation method for green and environmentally friendly sugammadex sodium. The preparation method obtains a crude productof sugammadex sodium through preparation for the first time by taking 3-mercaptopropionic acid, alkali and 6-deoxy-6-perhalogeno-gamma-cyclodextrin as raw materials; and high purity sugammadex sodiumcan be obtained after desolvation through recrystallization and column chromatography purification. Compared with the prior art, a reaction solvent of the preparation method can replace organic solvents like N,N-dimethylformamide used by traditional methods by only using water, so that disadvantages of hard recovery and large pollution caused by large amount of high boiling organic solvents can beimproved; and the sugammadex sodium is clean and environmentally friendly, green and efficient, has advantages of being mild in reaction condition, high in product purity, simple in post-treatment step, high in product yield, low in cost and convenient for industrialization, and has good application prospects.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to a green and environment-friendly preparation method of sugammadex sodium. Background technique [0002] The chemical name of sugammadex sodium is 6A, 6B, 6C, 6D, 6E, 7F, 6G, 6H-octa-S-(2-carboxyethyl)-6A, 6B, 6C, 6D, 6E, 7F, 6G, 6H-octathio-γ-cyclodextrin, octasodium salt, the structural formula is: [0003] [0004] Sugammadex sodium is a new type of muscle relaxant reversal agent developed by Organon in the Netherlands. It is clinically used to reverse the neuromuscular blockade of rocuronium or vecuronium. It has a good curative effect and has excellent security. Since the European Union approved its listing in July 2008, it has been listed in Japan, South Korea, the United States and other countries, and is applying for production and listing in my country. [0005] At present, there are few reports on the preparation process of sugammadex sodium at home and abroad, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 郭辉
Owner HEFEI BOSIKC PHARMTECH CO LTD
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