Preparation method of sugammadex sodium

A technology of sugammadex sodium and cyclodextrin, which is applied in the preparation field of sugammadex sodium, can solve the problems of low conversion rate and many impurities, and achieves a simple refining process, simple operation and few by-products. Effect

Pending Publication Date: 2019-12-27
LUNAN PHARMA GROUP CORPORATION
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] Aiming at the problems of low conversion rate and many impurities in the current preparation process of sugammadex sodium, the present invention aims to provide a s

Method used

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  • Preparation method of sugammadex sodium
  • Preparation method of sugammadex sodium
  • Preparation method of sugammadex sodium

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Experimental program
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Effect test

Embodiment 1

[0057] The synthesis of embodiment 1 intermediate I

[0058] Add 50.00g (34.63mmol) of 6-perdeoxy-6-perchloro-γ-cyclodextrin and 43.21g (553.97mmol) of sodium sulfide into 350mL DMF, stir and react at 90°C for 18h, then pour the reaction liquid into In 3.5L of purified water, adjust the pH to 2-3 with 10% dilute hydrochloric acid while stirring, and filter the filter cake with suction, add the filter cake to 560 mL of purified water and raise the temperature to 60°C for beating for 2 hours, filter with suction to obtain a solid product, and vacuum-dry at 50°C After 12 hours, a white solid was obtained, namely 6-perdeoxy-6-permercapto-γ-cyclodextrin, with a yield of 95.60%, HPLC: 99.10%.

Embodiment 2

[0059] The synthesis of embodiment 2 intermediate I

[0060] Add 50.00g (27.78mmol) of 6-perdeoxy-6-perbromo-γ-cyclodextrin and 34.67g (444.49mmol) of sodium sulfide into 350mL DMF, stir and react at 80°C for 14h, then pour the reaction liquid into In 3.5L of purified water, adjust the pH to 2-3 with 10% dilute hydrochloric acid while stirring, and filter the filter cake with suction, add the filter cake to 600 mL of purified water and raise the temperature to 60°C for beating for 2 hours, filter with suction to obtain a solid product, and dry it in vacuum at 50°C After 12 hours, a white solid was obtained, namely 6-perdeoxy-6-permercapto-γ-cyclodextrin, with a yield of 98.56%, HPLC: 99.60%.

Embodiment 3

[0061] The synthesis of embodiment 3 intermediate I

[0062] Add 50.00g (27.78mmol) of 6-perdeoxy-6-perbromo-γ-cyclodextrin and 34.67g (444.49mmol) of sodium sulfide into 350mL of dimethyl sulfoxide, and stir and react at 80°C for 14h. Pour the reaction solution into 3.5L of purified water, adjust the pH to 2-3 with 10% dilute hydrochloric acid while stirring, and filter with suction to obtain a filter cake, add the filter cake to 600mL of purified water and raise the temperature to 60°C for beating for 2 hours, and filter with suction to obtain a solid product , dried under vacuum at 50°C for 12 hours to obtain a white solid, namely 6-perdeoxy-6-permercapto-γ-cyclodextrin, with a yield of 96.01%, HPLC: 99.20%.

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Abstract

The invention provides a preparation method of sugammadex sodium. The method comprises the following steps: performing a reaction on perhalogenated gamma-cyclodextrin with a sulfo reagent to generatean intermediate I persulfydryl gamma-cyclodextrin, performing a reaction on the persulfydryl gamma-cyclodextrin with halogenated propionate to generate an intermediate II, and finally, carrying out hydrolysis salifying reaction to obtain sugammadex sodium. Compared with the prior art, the preparation method is simple to operate, mild in reaction condition, high in product yield, high in purity, less in pollution and suitable for industrial 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] The compound involved in the present invention is sugammadex sodium, the compound CAS number: 343306-79-6, the specific structural formula is as follows: [0003] [0004] Sugammadex Sodium, a new type of muscle relaxant reversal agent developed by Organon in the Netherlands, is used to reverse the blocking effect of the routinely used neuromuscular blocking drugs rocuronium bromide or vecuronium bromide , can immediately reverse the effects of rocuronium bromide used by adults, and routinely reverse the effects of rocuronium bromide used by children and adolescents (2 to 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 the past ...

Claims

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Application Information

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IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 张贵民张乃华鲍广龙
Owner LUNAN PHARMA GROUP CORPORATION
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