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Polyethylene glycol vitamin E succinate-cholesterol carbonate and its preparation method and application

A technology of cholesterol carbonate and succinate, which is applied in the direction of pharmaceutical formulations, medical preparations containing non-active ingredients, medical preparations containing active ingredients, etc., to achieve high yield, targeted targeting, and large drug loading capacity Effect

Active Publication Date: 2017-10-03
SHENYANG PHARMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(Lee, S.H., Z.Zhang, and S.-S.Feng, Nanoparticles of poly(lactide)—tocopherylpolyethylene glycol succinate(PLA-TPGS)copolymers for protein drugdelivery.Biomaterials,2007.28(11):p.2041-2050) It is feasible to modify the structure of polyethylene glycol vitamin E succinate, but the choice of ligand should be cautious

Method used

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  • Polyethylene glycol vitamin E succinate-cholesterol carbonate and its preparation method and application
  • Polyethylene glycol vitamin E succinate-cholesterol carbonate and its preparation method and application
  • Polyethylene glycol vitamin E succinate-cholesterol carbonate and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: TPGS 1000 -Synthesis of CHMC

[0044] Take 1g TPGS 1000 (0.66mmol) was placed in a closed container, 41.5mg 4-lutidine (DMAP) and 142.9μL triethylamine (TEA) were added under nitrogen, and dichloride of cholesteryl chloromethyl ester (CHM, 1mmol) was slowly added dropwise 20 mL of methane (DCM) solution was stirred and mixed in an ice-water bath for 10 min, and then refluxed at 45° C. for 24 h. After the reaction was completed, the solvent was removed under reduced pressure. (Synthetic process such as figure 1 As shown), add a certain amount of distilled water to the obtained crude product, extract three times with dichloromethane, then wash three times with 100mM hydrochloric acid, saturated sodium chloride and ice water respectively, and obtain a milky white wax by ice n-hexane precipitation, continue to use n-hexane Repeated precipitation and purification of alkanes for 3 times to obtain TPGS 1000 - Pure CHMC polymer.

[0045] During the reaction, sil...

Embodiment 2

[0051] Example 2: TPGS 400 -Synthesis of CHMC

[0052] Take 0.6g TPGS 400 (0.66mmol) was placed in a closed container, 41.5mg 4-lutidine (DMAP) and 142.9μL triethylamine (TEA) were added under nitrogen, and dichloride of cholesteryl chloromethyl ester (CHM, 1mmol) was slowly added dropwise 20 mL of methane (DCM) solution was stirred and mixed in an ice-water bath for 10 min, and then refluxed at 45° C. for 24 h. After the reaction was completed, the solvent was removed under reduced pressure. (Synthetic process such as figure 1 As shown), add a certain amount of distilled water to the obtained crude product, extract three times with dichloromethane, then wash three times with 100mM hydrochloric acid, saturated sodium chloride and ice water respectively, and obtain a milky white wax by ice n-hexane precipitation, continue to use n-hexane Repeated precipitation and purification of alkanes for 3 times to obtain TPGS 400 - Pure CHMC polymer.

[0053] During the reaction, sili...

Embodiment 3

[0059] Example 3: TPGS 6000 -Synthesis of CHMC

[0060] Take 4.3g TPGS 6000 (0.66mmol) was placed in a closed container, 41.5mg 4-lutidine (DMAP) and 142.9μL triethylamine (TEA) were added under nitrogen, and dichloride of cholesteryl chloromethyl ester (CHM, 1mmol) was slowly added dropwise 20 mL of methane (DCM) solution was stirred and mixed in an ice-water bath for 10 min, and then refluxed at 45° C. for 24 h. After the reaction was completed, the solvent was removed under reduced pressure. (Synthetic process such as figure 1 As shown), add a certain amount of distilled water to the obtained crude product, extract three times with dichloromethane, then wash three times with 100mM hydrochloric acid, saturated sodium chloride and ice water respectively, and obtain a milky white wax by ice n-hexane precipitation, continue to use n-hexane Repeated precipitation and purification of alkanes for 3 times to obtain TPGS 6000 - Pure CHMC polymer.

[0061] During the reaction, s...

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Abstract

The present invention relates to polymer TPGSn-cholesterol carbonate and its preparation method and application. The polymer takes TPGSn as the basic skeleton and is obtained by linking cholesterol at the hydroxyl end through a carbonate bond. The preparation method is as follows: take TPGSn and place it in a closed container, add a basic catalyst and an acid-binding agent under nitrogen, and slowly add a dichloromethane solution containing cholesteryl chloromethyl ester dropwise. Stir and mix in an ice-water bath for 5-30 min, then place it at room temperature for reaction, and remove the solvent under reduced pressure after the reaction to obtain a crude product; add an appropriate amount of distilled water to the obtained crude product, extract three times with dichloromethane, and then successively use 100 mM hydrochloric acid , saturated sodium chloride and ice water for 3 times, and precipitated by ice n-hexane to obtain a white wax; the resulting white wax can be refined by repeated precipitation with n-hexane. The polymer has good biocompatibility and biodegradability, and also has the advantages of low critical micelle concentration, good dilution stability, strong P-glycoprotein inhibitory effect, simple synthesis process, wide application range, and low cost. .

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and in particular relates to a preparation method of polyethylene glycol vitamin E succinate-cholesterol carbonate and its application in a drug delivery system. Background technique [0002] Polyethylene glycol vitamin E succinate (d-α-tocopherol polyethyleneglycol succinate, TPGS n , where n represents the molecular weight of polyethylene glycol) is a water-soluble derivative of vitamin E, which is formed by esterifying the carboxyl group of vitamin E succinate (VES) with polyethylene glycol (PEG) , wherein the molecular weight of PEG ranges from tens to tens of thousands. With the difference of molecular weight of PEG, there are also differences in its physical and chemical properties such as hydrophilic-lipophilic balance value (HLB) and oil-water partition coefficient (P). Polyethylene glycol vitamin E succinate was first developed and marketed by Eastman Company of the United St...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/00C07J17/00A61K47/28A61K9/107A61P35/00A61K31/765A61K31/58
Inventor 邓意辉宋艳志田清菁范迪黄振君刘欣荣张婷全晶晶程晓波佘振南
Owner SHENYANG PHARMA UNIVERSITY
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