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Chitin derivative and its preparation and its uses in preparation of medicines

A technology of polysaccharides and drugs, applied in the field of application in the preparation of drugs

Inactive Publication Date: 2006-08-16
南京亚东启天药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amphiphilic chitosan derivatives include 2-hydroxy-3-(p-nonylphenoxy) propyl-carboxymethyl chitosan (Sui Weiping, Chen Guohua, Gao Xianchi, etc. Chemical Journal of Chinese Universities, 2001, 22(1 ), 133-135), etc., but not used as a pharmaceutical carrier

Method used

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  • Chitin derivative and its preparation and its uses in preparation of medicines
  • Chitin derivative and its preparation and its uses in preparation of medicines
  • Chitin derivative and its preparation and its uses in preparation of medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] 1, the preparation of N-octyl chitosan (referring to literature: Baba Y, Hirakawa H.Chem Lett 1992,10,1905-1908)

[0079] Chitosan (1.0g) was suspended in 50ml of methanol and stirred at room temperature. Octanal (1.02g) was added. After continuing the reaction for 24 hours, 5ml of aqueous solution of KBH4 (0.5g) was added, and stirring was continued overnight. The reaction solution was washed with 2N hydrochloric acid solution. Neutralize, precipitate with methanol, filter, wash the filter residue three times with methanol and water, and dry at 60° C. in a vacuum oven overnight to obtain 1.0 g of light yellow powder N-octyl chitosan.

[0080] 2. Preparation of N-octyl-O-sulfonic acid chitosan (see literature: Hirano S, Tanaka Y, Hasegawa M, et al.Carbohy dr.Res.1985, 137, 205-215)

[0081] N-octyl chitosan (1.5g) was suspended in DMF (40ml) with mechanical stirring overnight, chlorosulfonic acid (20ml), at 0°C, N 2Under protection and stirring, it was slowly added dro...

Embodiment 2

[0087] 1. Preparation of N-decyl chitosan

[0088] Using decanal and chitosan to react, the preparation method is the same as that of N-octyl chitosan.

[0089] 2. Preparation of N-decyl-O-sulfonic chitosan

[0090] It is prepared by reacting N-decyl chitosan and chlorosulfonic acid, and the method is the same as that of N-octyl-O-sulfonic acid chitosan.

[0091] FT-IR: 2950, ​​2860, 1462, 1385, 800 cm-1 (long chain alkyl), 1260, 1221 1002 cm-1 (O=S=O).

[0092] 1H-NMR(D2O): δ(ppm): 3.0~3.3(m, 2H)(-NH-CH2-(CH2)8-CH3); 1.0~2.5(m, 8H)(-NH-CH2-(CH2 )8-CH3), 0.81(tri,3H)(-NH-CH2-(CH2)8-CH3).

[0093] 13C-NMR(D2O)δ(ppm): 13.5~13.7(-NH-CH2-(CH2)8-CH3); 22.3~34.2(-NH-CH 2 -(CH 2 ) 8 -CH 3 ); 48.0 (-NH-CH 2 -(CH 2 ) 8 -CH 3 );55.3(C 2 ), 62.1 (C 6 ), 65.9 (C 3 ), 75.7 (C 5 ), 77.1 (C 4 ), 97.5 (C 1 ).

[0094] Elemental analysis records that the degree of deacetylation is 91.5%, the degree of substitution of N-decyl group is 50%, and the degree of substitution of sul...

Embodiment 3

[0096] 1. Preparation of N-dodecyl-chitosan

[0097] React with lauryl aldehyde and chitosan, and the preparation method is the same as that of N-octyl chitosan.

[0098] 2. Preparation of N-dodecyl-O-sulfonic chitosan

[0099] It is prepared by reacting N-dodecyl chitosan with chlorosulfonic acid, and the method is the same as that of N-octyl-O-sulfonic acid chitosan.

[0100] FT-IR: 2952, 2865, 1462, 1385, 810cm -1 (long chain alkyl), 1265, 12211005cm -1 (O=S=O)

[0101] 1 H-NMR (D 2 O): δ (ppm): 2.6.0 ~ 3.4 (m, 2H) (-NH-CH 2 -(CH 2 ) 10 -CH 3 ); 0.8~3.3(m, 6H)(-NH-CH 2 -(CH 2 ) 10 -CH 3 ), 0.83(tri,3H)(-NH-CH 2 -(CH 2 ) 10 -CH 3 ).

[0102] 13 C-NMR (D 2 O)δ(ppm): 13.5~13.9(-NH-CH 2 -(CH 2 ) 10 -CH 3 ); 22.1~33.5(-NH-CH 2 -(CH 2 ) 10 -CH 3 ); 48.7(-NH-CH 2 -(CH 2 ) 10 -CH 3 );55(C 2 ), 61.8 (C 6 ), 67(C 3 ), 75.4 (C 5 ), 76.9 (C 4 ) and 97(C 1 ).

[0103] Elemental analysis records that the degree of deacetylation is 91.5%, the degree ...

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Abstract

A natural and biodegradable N-long chain alkyl-O-sulfochitosan, its preparing process, and its application as nano carrier which features low toxin, no hemolytic reaction and solubilization action to the medicine difficult to dissolve are disclosed. It can be used to prepare intravenous injection, such as the micellar medicine containing the component difficult to dissolve: taxol (or cyclosporin A) polymer.

Description

technical field [0001] The invention belongs to natural and biodegradable chitosan derivatives and a preparation method thereof, and its application as a drug carrier in the preparation of medicines; specifically, amphiphilic chitosan derivatives and a preparation method thereof, and As a drug nanocarrier, it is used to prepare polymer micelles that can solubilize insoluble drugs. Background technique [0002] Both nanotechnology and biodegradable materials are currently hot research areas for the development of drug delivery systems. The research on polymer micelles combines the advantages of both, which can be biodegradable and form drug nanocarriers. Compared with liposomes, microspheres or microcapsules, polymer micelles are composed of hydrophilic shells and hydrophobic cores, which not only have the medicinal properties of forming hydrophilic colloids, but also are suitable for the augmentation of hydrophobic drugs. Melt and wrap. Moreover, the particle size of the ...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K31/722
Inventor 平其能张灿张宏娟丁娅程耀
Owner 南京亚东启天药业有限公司
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