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Sugammadex sodium impurity and preparing method thereof

A technology of sugammadex sodium and impurities, applied in the field of drug synthesis, can solve the problem of not clearly obtaining sugammadex sodium oxide impurities, etc., and achieve the effects of high purity, high yield and convenient operation.

Inactive Publication Date: 2019-08-09
CHANGZHOU YABANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, at present, it is not clear what kind of compound the sugammadex sodium oxide impurity is, so it is urgent to research and develop the specific structure of the sugammadex sodium oxide impurity, which is the sugammadex sodium oxide impurity. Quality Control Provides Qualified Controls

Method used

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  • Sugammadex sodium impurity and preparing method thereof
  • Sugammadex sodium impurity and preparing method thereof
  • Sugammadex sodium impurity and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Reaction formula:

[0037]

[0038] Take sugammadex sodium 2.0g, add it to 5ml water, stir to dissolve and clarify, then add 20mg 30% H 2 o 2 , after stirring at 50° C. for 3 h, cooled to room temperature, and then added 10 ml of methanol, precipitated solid, filtered, and dried to obtain 2.1 g of solid, compound II: 16.1%, compound III: 20.4%. Then, the crude oxide was prepared and separated to obtain 70 mg of compound II with a purity of 92%, and 62 mg of compound III with a purity of 96%.

[0039] Compound I:

[0040] MS(m / z):1006.5[M-8Na+6H] - / 2.

[0041] 1 H-NMR (400MHz,D 2 O): δ2.63~2.66(m,16H), 2.78~2.90(m,24H), 3.10~3.20(m,8H), 3.44~3.60(m,16H), 3.80~3.91(m,16H), 5.07~5.16(m,8H).

[0042] Compound II:

[0043] MS(m / z):1006.9[M-8Na+6H] - / 2.

[0044] 1 H-NMR (400MHz,D 2 O): δ2.63~2.66(m,16H), 2.79~2.91(m,24H), 3.13~3.22(m,8H), 3.44~3.59(m,16H), 3.80~3.98(m,16H), 5.05~5.17(m,8H).

Embodiment 2

[0046] Reaction formula:

[0047]

[0048] Take 3.0g of sugammadex sodium, add it to 6ml of water, stir to dissolve and clarify, then add 30mg of 30% H 2 o 2 , after stirring at 50° C. for 3 h, cooled to room temperature, and then added 15 ml of methanol, precipitated solid, filtered, and dried to obtain 3.2 g of solid, compound II: 13.1%, compound III: 18.4%. Then, the crude oxide was prepared and separated to obtain 100 mg of compound II with a purity of 93%, and 70 mg of compound III with a purity of 94%.

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Abstract

The invention relates to the technical field of drug synthesis, in particular to a sugammadex sodium impurity and a preparing method thereof. A chemical structural formula of the impurity is shown ina formula I. The preparing method comprises the following steps that 1, sugammadex sodium is put in an aqueous solution, and after a reaction is carried out for a period of time at a certain temperature in the presence of an oxidizing agent, oxidation is conducted to generate a compound with the formula I, wherein the compound is a mixture of a compound II and a compound III; 2, the obtained mixture of the compound II and the compound III is subjected to preparative separation to obtain the single compound II and the single compound III. The preparing method has the advantages that operation is convenient, the reaction condition is mild and controllable, the stability of a reaction is high, and a reaction product is high in yield and purity; moreover, the compound with the formula I can provide an impurity reference substance which meets the requirement for quality control over the sugammadex sodium.

Description

Technical field [0001] The invention relates to the technical field of pharmaceutical synthesis, in particular to a kind of sugammadex sodium impurity and its preparation method. Background technique [0002] Sugammadex sodium (sugammadex sodium), chemical name is octa-6-perdeoxy-6-per(2-carboxyethyl)thio-γ-cyclodextrin sodium salt, trade name is Bridion, CAS: 343306- 71-8, the structural formula is as follows: [0003] [0004] Sugammadex sodium is a selective relaxing binding agent used to reverse the effects of the muscle relaxants rocuronium or vecuronium. It was first discovered by the Dutch company Organon Biosciences. On July 25, 2008, the European Medicines Agency approved sugammadex sodium for marketing in Europe. On October 20, 2010, sugammadex sodium was approved for marketing in Japan. In November 2015, the FDA approved the drug for marketing in the United States. . Currently, on April 26, 2017, the CFDA has approved the marketing of sugammadex sodium in Ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 陶锋马绍明陈松夏正君
Owner CHANGZHOU YABANG PHARMA
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