Preparation method of Sugammadex sodium and intermediate thereof

A technology of sugammadex sodium and its intermediates, which is applied in the field of preparation of sugammadex sodium and its intermediates, can solve the troublesome and dangerous problems of bromine reaction post-processing, and achieve high yield, easy operation, and high production efficiency. The effect of high rate and purity

Inactive Publication Date: 2019-07-09
北京晨光同创医药研究院有限公司
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Problems solved by technology

However, both the reaction and post-treatment of bromine are very cumbersome

Method used

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  • Preparation method of Sugammadex sodium and intermediate thereof
  • Preparation method of Sugammadex sodium and intermediate thereof
  • Preparation method of Sugammadex sodium and intermediate thereof

Examples

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Embodiment 1

[0044] Preparation of 6-perdeoxy-6-per(2-carboxyethyl)sulfanyl-γ-cyclodextrin (Sugammadex Sodium)

[0045]

[0046] Step 1: Preparation of Perbrominated γ-cyclodextrin (Compound II)

[0047] Add dry N,N-dimethylformamide (10L) into a 50L dry reaction kettle, replace the air with nitrogen, cool with ice water, and add triphenylphosphine (6.48Kg) while stirring. Dissolve pyridinium tribromide (7.89kg) in dry N,N-dimethylformamide (10L), and then add this solution dropwise to the N,N- in dimethylformamide solution. After the drop, the temperature was raised to 20-25°C and stirred for 2 hours, then a suspension of γ-cyclodextrin (2kg) in N,N-dimethylformamide (5L) was added dropwise, and the temperature was controlled at 20-25°C. After dropping, raise the temperature of the reaction solution to 65-70°C, continue the reaction for 16 hours, then cool the reaction solution to 5-10°C, and add 30wt% sodium methoxide methanol solution at this temperature to adjust the pH value to 8...

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Abstract

The present invention provides a preparation method of Sugammadex sodium and an intermediate thereof. The method comprises a bromination reaction of a compound of a formula (I) with a brominating reagent, wherein the brominating agent is selected from pyridinium tribromide. The method has the advantages of simple process, high yield, high purity and low pollution, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of sugammadex sodium and an intermediate thereof. Background technique [0002] Sugammadex sodium is the world's first selective antagonist of aminosteroid muscle relaxants developed by Merck & Co. First launched in Sweden in 2008, it is used to reverse muscle relaxation symptoms caused by rocuronium bromide or vecuronium bromide. On December 15, 2015, it was approved by the US FDA for marketing, and the trade name was Bridion (Bridion). [0003] Sugammadex sodium is a synthetic γ-cyclodextrin derivative, molecular formula: C 72 h 104 o 48 S 8 Na 8 , relative molecular mass: 2178.006. Its chemical structure is that 8 glucose molecules are connected end-to-end in the D-(+)-glucopyranose chair conformation to form a ring through α-1,4-glycosidic bonds, and the natural γ-ring is replaced by carboxyethyl sulfide group The hydroxyl group on the 6th carbon of each glucose molecule in dextrin deepens the i...

Claims

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Application Information

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IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 黄少林郭长彬马良
Owner 北京晨光同创医药研究院有限公司
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