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Method for preparing sulfobutyl ether-beta-cyclodextrin

A technology of sulfobutyl ether and cyclodextrin, which is applied in the field of organic synthetic drug excipients, can solve the problems of unfriendly environment, low yield, long reaction time, etc., and achieve shortened reaction time, simple process operation and high yield rate effect

Inactive Publication Date: 2017-04-19
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantage of this method is that water is used as a solvent without pollution, and the disadvantage is that the yield is not too high and the reaction time is long
Patent CN103694373 increases the solubility of 1,4-sulfobutyrolactone and improves the synthesis yield by introducing an appropriate amount of organic solvent into the alkaline aqueous solution, but the use of organic solvents is not environmentally friendly

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 1.135 g (1 mmol) of β-cyclodextrin to 30 mL of distilled water with stirring, and add 2.59 g (10 mmol) of Bu 4 N + Oh - , heated to 50°C to completely dissolve the β-cyclodextrin, raised the temperature to 60-70°C, slowly added 1.05g (8.6 mmol) of 1,4-sulfobutyrolactone, and controlled the temperature at 70-75°C for 9 hours. The reaction solution uses 6mol.L -1 Adjust the pH to 5.0-6.5 with HCl, filter, and the filtrate is separated by ultrafiltration membrane osmosis (1000 MWCO fiber ester membrane) 4 N + Cl - and sulfobutyl ether-β-cyclodextrin, to the Cl of the permeate - 3 solution testing). The reaction solution after dialysis was used with 6mol.L -1 NaOH solution into sodium salt, decolorized by activated carbon until the product detection UV absorption value <0.5AU, filtered, then passed the filtrate through a 0.65-0.2μm precision filter, and concentrated under reduced pressure until the content of sulfobutyl ether-β-cyclodextrin accounted for the solu...

Embodiment 2

[0018] With 2.59g (10 mmol) of BnMe 3 N + Oh - Replace the Bu of 2.59g (10 mmol) in embodiment 1 4 N + Oh - , other operations are the same as in Example 1, and 0.92g of white sulfobutyl ether-β-cyclodextrin powder is obtained, the yield is 82%, the average degree of substitution is 7.1, BnMe 3 N + The recovery rate of OH is 96%.

Embodiment 3

[0020] With 0.55g (4.5 mmol) of 1,4-sulfobutyrolactone instead of 1.05g (8.6 mmol) of 1,4-sulfobutyrolactone in Example 1, other operations are the same as in Example 1 to obtain white sulfobutyl Ether-β-cyclodextrin powder 0.83g, yield 78%, average degree of substitution 4.1, Bu 4 N + Oh - The recovery rate is 95%.

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PUM

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Abstract

The invention discloses a method for preparing sulfobutyl ether-beta-cyclodextrin. By using water as a solvent, beta-cyclodextrin and 1,4-sulfobutyrolactone, which are used as raw materials, undergo a substitution reaction in the presence of a catalyst quaternary ammonium base with double functions of strong basicity and phase-transfer catalysis; and then operations such as ultrafiltration, decolouring with active carbon, freeze-drying, etc. are successively carried out to finally obtain sulfobutyl ether-beta-cyclodextrin with high yield and high quality. The quaternary ammonium base used in the method can be recovered and recycled after a simple treatment. The preparation method of sulfobutyl ether-beta-cyclodextrin is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of organic synthetic pharmaceutical auxiliary materials, in particular to a method for preparing sulfobutyl ether-β-cyclodextrin. Background technique [0002] Sulfobutyl ether-β-cyclodextrin is an anionic, highly water-soluble derivative of β-cyclodextrin developed by Cydex Corporation of the United States in the 1990s. It has been listed in the United States and Sweden. The United States has used it to develop an advanced drug delivery technology, CAPTISOL, to improve the delivery of insoluble and unstable active pharmaceutical ingredients. And it has the incomparable advantages of other cyclodextrin derivatives, it can be well included with drug molecules to form non-covalent complexes, improve the stability, water solubility and safety of drugs, and can effectively improve drug biological activity of the molecule. It has low nephrotoxicity, can ease the hemolysis of drugs, and control the release rate of drugs. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
CPCC08B37/0012
Inventor 史兰香张冀男张宝华刘斯婕陈东
Owner SHIJIAZHUANG UNIVERSITY
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