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Carboxymethyl-hydroxypropyl-β-cyclodextrin and its preparation method

A carboxymethyl and cyclodextrin technology, which is applied in the field of carboxymethyl-hydroxypropyl-β-cyclodextrin and its preparation, can solve the problems of high dosage of prescription auxiliary materials, limited practicability, influence on cyclodextrin, and the like, Achieve good solubility, appropriate drug inclusion ability, and small hemolysis effect

Inactive Publication Date: 2017-01-11
NANJING NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a drug carrier, too large a molecular weight will make the dosage of prescription excipients too high, which will affect the actual function of cyclodextrin products and become an important reason for limiting its practicability

Method used

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  • Carboxymethyl-hydroxypropyl-β-cyclodextrin and its preparation method
  • Carboxymethyl-hydroxypropyl-β-cyclodextrin and its preparation method
  • Carboxymethyl-hydroxypropyl-β-cyclodextrin and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The three-necked round-bottomed flask is equipped with a constant pressure funnel, a reflux condenser, and a thermometer. Add 50ml of pure water into it, start stirring, and then slowly add 0.02mol β-cyclodextrin (22.7g) and 0.3mol solid NaOH (12.0g) under successive stirring. ), the system was dissolved and then heated slowly to keep at 80°C, then slowly added 0.08mol ethyl chloroacetate (9.8g) dropwise for about 4 hours, continued to stir and reflux for 2 hours and then cooled to room temperature. Control the temperature of the water bath to <20°C, slowly add 0.14mol of 1,2-propylene oxide (8.1g) dropwise to the system under stirring, and complete the addition in about 3 hours, continue to stir and react for 5 hours under the condition of the water bath temperature pH to neutral, filter, pour the filtrate into a dialysis bag, and dialyze to remove residual β-cyclodextrin and 1,2-propanediol and glycolic acid (sodium) produced by the reaction. After changing water and ...

Embodiment 2

[0079] Add 50ml of pure water to a three-necked round-bottom flask equipped with a constant pressure funnel, reflux condenser, and thermometer, start stirring, and then slowly add 0.02mol β-cyclodextrin (22.7g) and 0.14mol solid NaOH (12.0g) in sequence After the system is dissolved, control the temperature of the water bath to 1 HNMR verifies that the average degree of substitution of carboxymethyl is 2.1, and the average degree of substitution of hydroxypropyl is 5.8. The product is abbreviated as CM 2 -HP 6 -β-CD.

Embodiment 3

[0081] It is basically the same as Example 1, but the feeding amounts of NaOH, ethyl chloroacetate, and 1,2-propylene oxide are respectively 0.22, 0.04, and 0.05 mol. Finally, the product yield is 98.5%. 1 HNMR verifies that the average substitution degree of carboxymethyl group is 1.2, and the average substitution degree of hydroxypropyl group is 1.8. The product is abbreviated as CM 1 -HP 2 -β-CD.

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Abstract

Disclosed are a carboxymethyl-hydroxypropyl-β-cyclodextrin and preparation method thereof, the carboxymethyl-hydroxypropyl-β-cyclodextrin being a β-cyclodextrin derivative mixedly substituted by carboxymethyl and hydroxypropyl, the derivative being: n-(2, 3, 6-O-carboxymethyl)-m-(2, 3, 6-O-2-hydroxypropyl)-β-cyclodextrin. The substituted groups of each mole of cyclodextrin contain n carboxymethyl and m hydroxypropyl, m being the number of connections to hydroxypropyl in each mole of cyclodextrin derivative, that is, the average degree of substitution of hydroxypropyl, and n being the number of connections to carboxymethyl in each mole of cyclodextrin derivative, that is, the average degree of substitution of carboxymethyl, where m is a number selected from 1 to 6 and n is a number selected from 1 to 6. The present invention acts as a medical excipient, and has the features of low hemolytic property, low toxicity, and strong solubility.

Description

technical field [0001] The invention relates to a beta-cyclodextrin derivative carboxymethyl-hydroxypropyl-beta-cyclodextrin which is mixed and substituted by carboxymethyl and hydroxypropyl and is used as a pharmaceutical excipient and a preparation method thereof. Background technique [0002] β-cyclodextrin (β-cyclodextrin, β-CD) is a cyclic oligosaccharide natural product obtained by enzymatic hydrolysis and cyclization of starch by cyclodextrin dextran translocase. β-CD molecules are connected by glycosidic bonds to form a truncated conical body with a hollow cavity, and 21 hydroxyl groups are distributed around the cavity of the cone. Its characteristics of hydrophobic inside the cavity and hydrophilic outside the cavity enable β-CD to form supramolecules (inclusion complexes) with weak interactions between host and guest molecules with small organic molecules. The physical and chemical properties of organic small molecules are improved due to the formation of supramo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K47/40
CPCA61K47/40C08B37/0012
Inventor 任勇孙海松余书勤张列峰
Owner NANJING NORMAL UNIVERSITY
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