Quaterisation chitosan derivatives, preparation method and medicinal preparation containing the derivatives

A technology of quaternized chitosan and derivatives, applied in the field of polymer chemistry, can solve the problem of severe allergic reactions in patients, achieve good solubilization effect, improve treatment effect, and reduce phagocytosis effect

Active Publication Date: 2006-04-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the nature of these surfactants, such injections containing la

Method used

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  • Quaterisation chitosan derivatives, preparation method and medicinal preparation containing the derivatives
  • Quaterisation chitosan derivatives, preparation method and medicinal preparation containing the derivatives
  • Quaterisation chitosan derivatives, preparation method and medicinal preparation containing the derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1. Preparation of N-octyl chitosan (OCS)

[0034] Add 12g chitosan and 34.0ml n-octylaldehyde into 250ml methanol, stir at 30°C for 5h, then add KBH in batches 4(a total of 6g / 60ml), after stirring overnight, filtered, washed the filter cake repeatedly with water and hot methanol, and vacuum-dried at 50°C to obtain 11.3g of light yellow powder OCS (octyl substitution degree was 10%).

[0035] 2. Preparation of N-alkyl-N-quaternized chitosan (OTMCS1)

[0036] 0.96g N-octyl chitosan was placed in a 100ml three-neck flask, and 15ml N-methylpyrrolidone, 2.4g KI, 5ml 15% NaOH aqueous solution and 5.2ml CH 3 I, under full stirring, heat up to 60°C for 1h, cool to room temperature, centrifuge for 30min (1000rpm), collect the lower layer solid (I) and dissolve it in distilled water, dialyze for 5d, filter the insoluble matter and freeze-dry the filtrate to obtain light yellow N - 0.34 g of octyl-N-quaternized chitosan (OTMCS1) (substitution degree of quaternary amine is 53%)....

Embodiment 2

[0050] 1. Preparation of N-decyl chitosan (DCS)

[0051] With decanal and chitosan reaction, preparation method is the same as the preparation method of N-octyl chitosan among the embodiment 1.

[0052] 2. Preparation of N-decyl-N-quaternized chitosan (DTMCS1,)

[0053] It is prepared by reacting N-decyl chitosan and methyl iodide, and the preparation method is the same as that of OTMCS1 in Example 1.

[0054] FT-IR: 2953, 2872, 1080, 1035, 810cm -1

[0055] 1 H NMR (500MHz, D 2 O): 5.4 (H 1 ), 4.3~3.4(H 3 , H 4 , H 5 , H 6 ), 3.0~3.3(N(CH 3 ) 3 ,-NH-CH 2 -(CH 2 ) 8 -CH 3 , H 2 ), 2.6(N(CH 3 ) 2 , 1.3~2.3(-NH-CH 2 -(CH 2 ) 8 -CH 3 ), 0.82 (-NH-CH 2 -(CH 2 ) 8 -CH 3 ).

[0056] 13 C NMR (500MHz, D 2 O): 99.6 (C 1 ), 77.5 (C 4 ), 77(C 5 ), 68.4 (C 3 ), 61.1 (C 6 ), 58.6 (C 2 ), 52.9(N(CH 3 ) 3 ), 45.0 (-NH-CH 2 -(CH 2 ) 8 -CH 3 ), 40.9 (N (CH 3 ) 2 ), 34.3 (-NH-CH 2 -(CH 2 )8 -CH 3 ), 20.1~23.9 (-NH-CH 2 -(CH 2 ) 8 -CH 3 ).

[0...

Embodiment 3

[0065] 1. Preparation of N-dodecyl-chitosan (LCS)

[0066] With lauric aldehyde and chitosan reaction, preparation method is the same as the N-octyl chitosan of embodiment 1.

[0067] 2. Preparation of N-decyl-N-quaternized chitosan (LTMCS1)

[0068] It is prepared by reacting N-dodecyl chitosan and methyl iodide, and the method is the same as that of OTMCS1 in Example 1.

[0069] FT-IR: 2950, ​​2850, 2950, ​​2860, 1462, 1385, 800em -1 .

[0070] 1 H NMR (500MHz, D 2 O): 5.42 (H 1 ), 4.3~3.4(H 3 , H 4 , H 5 , H 6 ), 3.0~3.3 (-NH-CH 2 -(CH 2 ) 8 -CH 3 , N(CH 3 ) 3 , H 2 ), 2.5(N(CH 3 ) 2 ), 1.0~2.5(-NH-CH 2 -(CH 2 ) 8 -CH 3 NOCOCH 3 ), 0.8(-NH-CH 2 -(CH 2 ) 8 -CH 3 ).

[0071] 13 C NMR (500MHz, D 2 O): 97.5 (C 1 ), 77.1 (C 4 ), 75.7 (C 5 ), 65.9 (C 3 ), 62.1 (C 6 ), 55.3 (C 2 ), 53.7(N(CH 3 ) 3 ), 48.0 (-NH-CH 2 -(CH 2 ) 8 -CH 3 ), 41.1 (N (CH 3 ) 2 ), 22.3~34.2; (-NH-CH 2 -(CH 2 ) 8 -CH 3 ), 13.5~13.7(-NH-CH 2 -(CH 2 ) 8 -CH ...

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Abstract

A quaternary ammonium chitosan derivative able to be used as solubilizer of the medicines difficult to dissolve, its preparing process and its composite medicine are disclosed.

Description

technical field [0001] The invention relates to the field of polymer chemistry and the field of pharmaceutical auxiliary materials. It specifically relates to a class of quaternized chitosan derivatives, especially a quaternized chitosan derivative capable of forming amphiphilic polymer molecules and a preparation method thereof, and also relates to its function as a solubilizer for insoluble drugs and the its pharmaceutical composition. Background technique [0002] Surfactant micellar solubilization is a commonly used means to improve the solubility of insoluble drugs in pharmaceutical preparations. For example, paclitaxel and docetaxel are insoluble antitumor drugs. Polyoxyethylene castor oil and Tween-80 are used in clinical practice respectively. Solubilized and diluted for intravenous injection just before use. However, due to the properties of these surfactants, such injections containing large amounts of surfactants can cause severe allergic reactions in some patie...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K31/722
Inventor 平其能张灿丁娅朱贤
Owner CHINA PHARM UNIV
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