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Hydroxypropyl- sulfobutyl-beta- cyclodextrin and its preparation method, analytical method and pharmaceutical uses

一种分析方法、环糊精的技术，应用在药物载体,羟丙基-磺丁基-β-环糊精领域，能够解决赋形剂配比高、影响环糊精作用功能等问题

Active Publication Date: 2006-07-12
BIKA BIOTECH GUANGZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cyclodextrin and its derivatives usually have a much larger molecular weight than the drug, and it is often necessary to use more cyclodextrin than the mass ratio of the drug in practical applications. It has been proved that the cyclodextrin derivatives with too large molecular weight make the excipient If the proportion of the agent is too high, it will affect the function of cyclodextrin and become an important factor restricting its application.

Method used

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  • Hydroxypropyl- sulfobutyl-beta- cyclodextrin and its preparation method, analytical method and pharmaceutical uses
  • Hydroxypropyl- sulfobutyl-beta- cyclodextrin and its preparation method, analytical method and pharmaceutical uses
  • Hydroxypropyl- sulfobutyl-beta- cyclodextrin and its preparation method, analytical method and pharmaceutical uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156] Example 1, respectively add 0.02molβ-cyclodextrin, 0.11molNaOH, 45mlH 2 O, Stir to dissolve and heat to 75°C ~ 80°C, then add 0.08mol 1,4-butyl sultone dropwise in a heat-retaining manner, finish adding in about 3 hours, continue to stir for 2 hours, then cool to room temperature 20°C, slowly drop while stirring Add 0.08mol 1,2-propylene oxide, add about 3 hours, continue stirring for 5 hours, adjust pH to neutral with hydrochloric acid, filter, and dialyze the filtrate to remove residual β-cyclodextrin and 1,2-propanediol and Sodium gamma-hydroxybutanesulfonate. After dialysis for 8-10 times, it was concentrated and dried under reduced pressure to obtain 25.7 g of off-white solid with a weight yield of 111.7%. 1 HNMR spectrum (attached Figure 12 ) values ​​are analyzed in the following table:

[0157]

ppm

proton attribution

peak characteristics

Peak area

proton group

Degree of substitution DS

1.05...

Embodiment 2

[0163] Example 2, respectively add 0.02mol of β-cyclodextrin, 0.04mol of NaOH, 90mlH 2 O, stir to dissolve, slowly add 0.03mol of 1,2-epoxypropylene dropwise under stirring at 20°C, and finish adding in about 2 hours. Add 0.3 mol of 1,4-butyl sultone dropwise, finish adding in about 3 hours, continue to stir for 5 hours, then cool to room temperature, adjust the pH to neutral with hydrochloric acid, filter, and dialyze the filtrate to remove residual β-cyclodextrin and 1,2-propanediol and sodium γ-hydroxybutanesulfonate produced by the reaction. After dialysis for 8-10 times, concentrated and dried under reduced pressure to obtain 25 g of off-white solid with a yield of 108.7%. 1 HNMR verification shows that the average substitution number of hydroxypropyl is 1.2, and the average substitution degree of sulfobutyl is 8.9, abbreviated as HP 1 -SBE 9 -β-CD.

Embodiment 3

[0164] Embodiment 3, is substantially the same as embodiment 1, but adds 70mlH 2 O, where adding NaOH, 1,4-butyl sultone, and 1,2-propylene oxide are charged at 0.20, 0.16, and 0.10 mol. Finally, the product yield is 105.5%. 1 HNMR (with Figure 15) verified that the average substitution number of hydroxypropyl is 5.6, and the average substitution degree of sulfobutyl is 2.6, abbreviated as HP 3 -SBE 6 -β-CD.

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PUM

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Abstract

The invention relates to a hydroxypropyl -sulfo butyl -ª‰-cyclodextrin and its preparing method, analysis method and the applying in medicine, wherein the hydroxypropyl -sulfo butyl -ª‰-cyclodextrin is the cyclodextrin derivation displaced by hydroxypropyl and sulfo butyl. The n-(2, 3, 6-O-2-hydroxypropyl )-m-(2, 3, 6-O-sulfo butyl)-ª‰-cyclodextrin, each mole cyclodextrin displaced group number is n hydroxypropyl and m sulfo butyl, wherein n is the average displaced degree of the hydroxypropyl displaced group; m is the average displaced degree of the sulfo butyl displaced group; n+mú¢Z is the total average displaced degree; nú¢any of the 1,2,3,4,5,6, 7,8,9; m=any of the 1,2,3,4,5,6, 7,8,9; z=any of the 1,2,3,4,5,6, 7,8,9,10.

Description

technical field [0001] The invention relates to a drug carrier: hydroxypropyl-sulfobutyl-β-cyclodextrin, in particular to a cyclodextrin derivative hydroxypropyl-sulfobutyl-β-cyclodextrin mixed with hydroxypropyl and sulfobutyl Dextrin, the preparation method and analysis method of this hydroxypropyl-sulfobutyl-β-cyclodextrin, and its pharmaceutical application as a drug carrier. Background technique [0002] Cyclodextrin (cyclodextrin, CD) is a cyclic oligosaccharide natural product obtained by enzymatic hydrolysis and cyclization of starch by cyclodextrin dextran translocase. The common ones are α-, β- and γ-CD, which contain 6, 7, and 8 glucose molecules respectively, and are in the shape of a truncated cone with a hollow hydrophobic inner cavity. The hydroxyl groups of the glucose units are distributed on the periphery of the cavity. Hydrophilic. The special molecular structure of "hydrophobic on the inside and hydrophilic on the outside" enables CD to form a supramole...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16A61K31/724A61K9/08A61P3/00
CPCA61K9/0019C08B37/0015A61K31/724C08L5/16C08B37/0012A61K47/40B82Y5/00A61K47/48969G01N2030/884A61K47/6951Y10T436/143333A61P29/00A61P3/00A61P43/00
Inventor 任勇马学琴余书勤孙晓东
Owner BIKA BIOTECH GUANGZHOU CO LTD
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