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An improved process for the preparation of sugammadex

一种葡萄糖、巯基丙酸的技术，应用在改进的制备舒更葡萄糖领域，能够解决不可取、难工业规模中实施和控制、难以处理等问题

Active Publication Date: 2018-11-09
FRESENIUS KABI IPSUM SRL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] The alternative method disclosed in CN104844732A2 involves specific techniques and instruments for the preparation of sugammadex, which are difficult to implement and control on an industrial scale
[0031] (iii) The use of pyrophoric reagents such as sodium hydride is also not recommended due to the difficulty in handling sugammadex on a large scale
[0032] (iv) Difficult to implement and control on an industrial scale using special techniques such as chromatographic purification and utilization of ultraviolet light
[0033] Finally, longer durations, handling of reagents, use of special techniques and lower purity of sugammadex are not advisable for the preparation of sugammadex

Method used

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  • An improved process for the preparation of sugammadex
  • An improved process for the preparation of sugammadex

Examples

Experimental program
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Embodiment

[0115] In order to illustrate and explain the benefits of the present invention, an example of prior art has been carried out and presented as a reference example.

reference example 1

[0116] Reference Example 1 (Example 4 of WO2001 / 040316A1)

[0117] Preparation of sugammadex

[0118] Under nitrogen atmosphere, 3-mercaptopropionic acid (1.95 mL, 10 equiv) was dissolved in anhydrous dimethylformamide (72 mL) at room temperature. To this solution was added sodium hydride (1.97 g, 22 equiv, 60% dispersion in mineral oil) in three portions, and the mixture was stirred for a further 30 minutes. To this mixture was then added dropwise a solution of 6-per-deoxy-6-per-iodo-γ-cyclodextrin (5 g, 2.24 mmol) in anhydrous dimethylformamide (72 mL). After the addition, the reaction mixture was heated at 70 °C for 12 hours. After cooling, water (16 mL) was added to the mixture, and the volume was concentrated in vacuo to 64 mL. Ethanol (400 mL) was added, causing precipitation. The solid precipitate was collected by filtration and dialyzed for 36 hours. The volume was then reduced to 32 mL in vacuo. Ethanol was added thereto, and the precipitate was collected by fil...

reference example 2

[0119] Reference Example 2 (Example 2 of WO2012 / 025937A1)

[0120] Preparation of sugammadex

[0121] To a mixture of sodium hydride (60% dispersion in mineral oil, 3.13 g) in dimethylformamide (19 mL, 3.8 volumes) was slowly added 3-mercaptopropionic acid (3 mL, 10 equiv) under nitrogen. Solution in dimethylformamide (6 mL, 1.2 vol), keeping the temperature below 10 °C. The resulting mixture was stirred at 20-25°C for 30 minutes. 6-per-deoxy-6-per-chloro-γ-cyclodextrin (5 g) in dimethylformamide (50 mL, 10 volumes) was then slowly added under nitrogen at 5-10 °C, and The resulting mixture was heated to 70-75°C for 12 hours. The reaction mixture was cooled to 20-25 °C and dimethylformamide was partially removed under vacuum, and the reaction mixture was diluted with ethanol (75 mL, 15 vol). The resulting precipitate was stirred at 20-25°C for 1 hour and filtered, washed with ethanol (10 mL, 2 volumes) and dried under vacuum at 60-65°C. Obtained 9.4 g of an ivory colored s...

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Abstract

The present application provides an improved process for the preparation of sugammadex by reacting a salt of 3-mercapto propionic acid with 6-per-deoxy-6- per-halo-[gamma]-cyclodextrin in a suitable organic solvent. This application also provides crystalline form of a salt of 3-mercapto propionic acid, preferably di sodium salt of 3-mercapto propionic acid and its use for the preparation of sugammadex, whereas formula (I) shows the sodium salt of sugammadex.

Description

field of invention [0001] The present application provides an improved process for the preparation of sugammadex. More specifically, the present application relates to the reaction of a salt of 3-mercaptopropionic acid with 6-per-deoxy-6-per-chloro-γ-cyclodextrin to obtain sugammadex, wherein said salt is preferably selected from the group consisting of 3 - the disodium salt of mercaptopropionic acid, the dipotassium salt of 3-mercaptopropionic acid and the dilithium salt of 3-mercaptopropionic acid. The present application also relates to the use of the dialkali metal salt of the isolated crystalline compound 3-mercaptopropionic acid for the preparation of sugammadex, which improves the overall purity and / or reaction time of sugammadex. [0002] The present application provides an improved industrially viable method that is efficient, less time consuming, reproducible and involves less toxic reagents. Background technique [0003] Sugammadex with marketed, and whose str...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012C07C319/12C07C323/52C08B37/0003
Inventor W·卡布里A·利奇J·赞侬S·拉西里G·辛格S·H·谢尔克T·比斯瓦尔N·库玛M·辛格
Owner FRESENIUS KABI IPSUM SRL
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