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Amphiphilic chitosan derivative, its preparation method and its application in medicinal preparation

A technology for chitosan derivatives and drugs, which can be used in pharmaceutical formulations, medical preparations containing active ingredients, and liquid delivery, etc., can solve problems such as insolubility in organic solvents, achieve low toxicity, improve therapeutic effects, and high yields Effect

Inactive Publication Date: 2012-07-18
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invented amphiphilic chitosan derivatives can only be dissolved in water and cannot be dissolved in organic solvents

Method used

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  • Amphiphilic chitosan derivative, its preparation method and its application in medicinal preparation
  • Amphiphilic chitosan derivative, its preparation method and its application in medicinal preparation
  • Amphiphilic chitosan derivative, its preparation method and its application in medicinal preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] 1, the preparation of N-octyl chitosan (referring to CN 03112981.1)

[0048] Chitosan (1.0g) was suspended in 50mL of methanol and stirred at room temperature, octanal (1.02g) was added, and after 24 hours of reaction, KBH was added 4 (0.5g) in 5mL aqueous solution, continue to stir overnight, the reaction solution is neutralized with 2N hydrochloric acid solution, precipitated with methanol, filtered, and the filter residue is repeatedly washed with methanol and water for 3 times, and dried overnight at 60°C in a vacuum oven to obtain shallow Yellow powder N-octyl chitosan 1.0g.

[0049] N-alkylated chitosan such as N-decyl chitosan, N-lauryl chitosan, N-octadecyl, N-cholesteryl chitosan can be prepared by the same method.

[0050] 2. Preparation of N-octyl-N'-phthaloyl chitosan

[0051] N-octyl chitosan (1.5g) was suspended in DMF (40mL) and mechanically stirred overnight, N 2 Under protection and stirring, 1.9 g of phthalic anhydride was slowly added, the temperat...

Embodiment 2

[0060] 1. Preparation of N-decyl chitosan

[0061] Using decanal and chitosan to react, the preparation method is the same as that of N-octyl chitosan.

[0062] 2, Preparation of N-decyl-N'-phthaloyl chitosan

[0063] It is prepared by reacting N-decyl chitosan with phthalic anhydride, and the method is the same as that of N-octyl-N'-phthaloyl chitosan. The same method can prepare N-decyl-N'-maleyl chitosan, N-decyl-N'-(3-formyl propionic acid) chitosan, N-decyl-N'- (4-formylbutyric acid) chitosan and other acid anhydride chitosan.

[0064] 3, Preparation of N-decyl-N'-phthaloyl-O-hydroxypropylated chitosan

[0065] React with N-decyl-N'-phthaloyl chitosan and polyphosphoric acid, and the preparation method is the same as OPHPC.

[0066] FT IR: 2860, 1386, 1287, 908, 718cm -1 (long chain alkyl), 1121cm -1 (hydroxypropyl), 1718cm -1 (phthaloyl).

[0067] 'H-NMR (D 2 O): δ (ppm): 0.6-1.8 (m, 15H) (-NH-CH 2 -(C H 2 ) 6 -C H 3 ); 2.5-2.8(m, 2H)(-NH-C H 2 -(CH 2 )...

Embodiment 3

[0072] 1, Preparation of N-octadecyl chitosan

[0073] The reaction between octadecanal and chitosan is the same as that of N-octyl chitosan.

[0074] 2, Preparation of N-octadecyl-N'-phthaloyl chitosan

[0075] It is prepared by reacting N-octadecyl chitosan with phthalic anhydride, and the method is the same as that of N-octyl-N'-phthaloyl chitosan. The same method can prepare N-octadecyl-N'-maleyl chitosan, N-octadecyl-N'-(3-formyl propionic acid) chitosan, N-octadecyl Anhydrous chitosan such as alkyl-N'-(4-formylbutyric acid) chitosan.

[0076] 3, Preparation of N-octadecyl-N'-phthaloyl-O-hydroxypropylated chitosan

[0077] React with N-octadecyl-N'-phthaloyl chitosan and polyphosphoric acid, and the preparation method is the same as OPHPC.

[0078] FT IR: 2860, 1386, 1287, 908, 718cm -1 (long chain alkyl), 1121cm -1 (hydroxypropyl), 1718cm -1 (phthaloyl).

[0079] 'H-NMR (D 2 O): δ (ppm): 0.6-1.8 (m, 15H) (-NH-CH 2 -(C H 2 ) 6 -C H 3 ); 2.5-2.8(m, 2H)(-NH-C...

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Abstract

The invention relates to the medical auxiliary material chitosan derivative field, and more specifically relates to an amphiphilic chitosan derivative (I), its preparation method and its application in a medicinal preparation. The chitosan derivative of the present invention is a polymer capable of carrying out biodegradation in vivo possessing amphiphilic polymer molecules, which is characterized in that one end contains hydrophilic group, the other end contains hydrophobic group, and is suitable for medicines, matching with medicines or being as a medicine carrier, and especially can be the medicine carrier with small toxicity and no hemolytic reaction capable of intravenous injection administration.

Description

technical field [0001] The invention relates to an amphiphilic derivatized product using natural and biodegradable chitosan as a raw material and a preparation method thereof, as well as its application as a drug carrier in the preparation of medicines. Background technique [0002] Both nanotechnology and biodegradable materials are hot research areas in the development of current drug delivery systems. The research on polymer micelles combines the advantages of both, which can be biodegradable and form drug nanocarriers. Polymer micelles are composed of a hydrophilic shell and a hydrophobic core, which not only have the medicinal properties of forming a hydrophilic colloid, but also are suitable for the solubilization and encapsulation of hydrophobic drugs. The polymer micelle is composed of a hydrophilic shell and a hydrophobic core, so that it can achieve the purpose of long circulation in the body and reduce the phagocytosis of reticuloendothelial cells. [0003] Chit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K47/36A61K9/10A61K45/00
Inventor 张灿瞿鼎林海娇曲国威李文婷张楠
Owner CHINA PHARM UNIV
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