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Polysaccharide acylate and preparation method thereof

A technology for acylate and polysaccharides, applied in the field of polysaccharide acylate and its preparation, can solve the problems of unfixed target structure, uncertain position of acylation, unstable activity, etc.

Active Publication Date: 2013-04-24
ANHUI FENGYUAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although WO2005 / 089365A2 has reports about the use of heparin acylate for the inhibition of tumor proliferation, the acylation reaction synthesis method is to acylate the hydroxyl group on the polysaccharide under the action of the small molecule catalyst dimethylaminopyridine, and the acylation The position is uncertain, the structure of the obtained target is not fixed, the process controllability is poor, and the activity is unstable
There is also no report that heparin acylate is used as an injection in clinical practice.

Method used

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  • Polysaccharide acylate and preparation method thereof
  • Polysaccharide acylate and preparation method thereof
  • Polysaccharide acylate and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Dissolve 200mg of low-molecular-weight heparin sodium (Jiangsu Wanbang Biochemical Pharmaceutical Co., Ltd., molecular weight less than 8000Da) in 1-20ml of water, pass through an ion exchange column, collect the heparin aqueous solution, add 0.1-5.0ml of tributylamine, and freeze at -80°C for 1 hour , concentrated under reduced pressure to remove water to obtain 203 mg of solid. Then dissolve it in 2-50ml of dichloromethane solvent, add 1-100mg of DCC and stir to dissolve, add 1.1-2.0ml of butyric anhydride while stirring at 0°C, react for 1h, then stir at room temperature for 1-72h. Then add 1-50ml of 5% sodium hydroxide aqueous solution to the reaction solution, stir for 2-72h, filter to remove the solid, add dilute hydrochloric acid to adjust the pH value to 7, extract with ether to remove impurities, concentrate under reduced pressure and pass through a gel column to collect the target The product was dried under reduced pressure to obtain 150 mg of the light yello...

Embodiment 2

[0043] Dissolve 200 mg of low-molecular-weight heparin (Hebei Changshan Biochemical Pharmaceutical Co., Ltd., molecular weight less than 12,000 Da) in 1-20 ml of water, pass through an ion exchange column, collect the heparin aqueous solution, add 0.1-5 ml of tributylamine, and store at -80 ° C Freeze for 1 h, and concentrate under reduced pressure to remove water to obtain 203 mg of white solid. Then dissolve it in 2-50ml of dichloromethane solvent, add 1-100mg of DCC, stir to dissolve, add 0.1-1.0ml of butyric anhydride while stirring at 0°C, react for 1h, then stir at room temperature for 1-72h. Then add 1-50ml of 5% sodium hydroxide aqueous solution to the reaction solution, stir for 2-72h, filter to remove the solid, add dilute hydrochloric acid to adjust the pH value to 7, extract with ether to remove impurities, concentrate under reduced pressure and pass through a gel column to collect the target The product was dried under reduced pressure to obtain 160 mg of the ligh...

Embodiment 3

[0045] Dissolve 200mg of low-molecular-weight heparin sodium (self-degradation, molecular weight less than 4000Da) in 1-20ml of water, pass through an ion exchange column, collect the heparin aqueous solution, add 0.1-5ml of tributylamine, freeze at -80°C for 1 hour, and concentrate under reduced pressure to remove water 203mg of white solid was obtained. Then dissolve it in 2-50ml of dichloromethane solvent, add 1-100mg of DCC, stir to dissolve, add 2.1-5.0ml of acetic anhydride while stirring at 0°C, react for 1h, then stir at room temperature for 1-72h. Then add 1-50ml of 5% aqueous sodium hydroxide solution to the reaction solution, stir for 2-72h, add dilute hydrochloric acid to adjust the pH value to 7, dialyze for 2-72h, filter to remove impurities, freeze-dry to obtain 120mg of the light yellow target substance, (product rate 60%). 1 See HNMR image 3 .

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Abstract

The invention relates to a polysaccharide acylate and a preparation method thereof. The polysaccharide acylate is represented by a general formula (I), wherein R1 is COCH3 or SO3<->, R2 is H or SO3<->, R3 is COR, R4 is COR or SO3<->, n is an integer in a range of 2 to 16, and R is an alkyl group. The polysaccharide acylate provided by the invention has strong antineoplastic and anti-inflammatory activity and a clear and definite structure, and the preparation method for the polysaccharide acylate is controllable.

Description

technical field [0001] The invention relates to the preparation of polysaccharides, in particular to a polysaccharide acylate and a preparation method thereof. Background technique [0002] The applications of glycosaminoglycans from mammalian viscera are mostly antiplatelet drugs, anticoagulant drugs, and thrombolytic drugs. In recent years, with the advancement of chemical synthesis and analysis technology, its application fields have been continuously expanded. In 2000, Japanese Patent Patent Publication No. 2000-344674 disclosed the patents of vascular endothelial factor inhibitors and angiogenesis inhibitors. By desulfating heparin, the obtained heparinoids can be used for inflammatory diseases, diabetic retinopathy, joint inflammation, psoriasis, tumor proliferation, myocardial infarction and ovarian stimulation syndrome. In 2005, Japanese Patent Publication No. 2005-506326 disclosed a heparanase inhibitor-partially desulfated glycosaminoglycan inducer with antiangio...

Claims

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Application Information

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IPC IPC(8): C08B37/10C07H13/06C07H1/00A61P35/00A61P35/02A61P29/00A61P9/10A61P9/00A61P7/02A61P13/12A61P9/12A61P11/00A61P11/06A61P25/00A61P19/02A61P37/02A61P37/06A61P3/10A61P1/00A61P1/04
Inventor 梁颖蒋志文刘浩蒋琛琛吴成柱张亚李立标
Owner ANHUI FENGYUAN PHARM CO LTD
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