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Ph-responsive lipids

A responsive, lipid-based technology, applied in liposome delivery, cyanide reaction preparation, glycopeptide components, etc., can solve the problems of phospholipid usage restrictions, expensive production of synthetic phospholipids, lipid impurity and purification, etc.

Inactive Publication Date: 2019-06-04
UNIV OF KWAZULU NATAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, despite excellent biocompatibility and widespread use in drug delivery systems, the use of phospholipids is still limited because naturally occurring lipids are impure and their purification is difficult, while the production of synthetic phospholipids is very expensive.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Synthesis of tert-butyl 3-((2-hydroxyethyl)amino)propionate (compound 3):

[0121] To a solution of tert-butyl acrylate (compound 2) (1.05 mol) in methanol (500 mL) was added 2-aminoethanol (compound 1) (1.0 mol) at room temperature, followed by stirring at the same temperature for 24 hours. Methanol and excess tert-butyl acrylate were evaporated in vacuo and the resulting residue was purified by column chromatography using hexane and ethyl acetate (3:1) to give compound 3 as a thick oil (80%).

Embodiment 2

[0123] Synthesis of tert-butyl 3-((1,3-dihydroxypropan-2-yl)amino)propionate (compound 6):

[0124] Add 2-amino-1,3-propanediol (compound 5) (1.0mol) to a solution of tert-butyl acrylate (compound 2) (1.10mol) in ethanol (300mL) at room temperature, and stir 4- 5 hours. Ethanol and excess tert-butyl acrylate were evaporated in vacuo and the resulting residue was recrystallized from hexane and ethyl acetate (3:1) to afford compound 6 as a white solid (92%).

Embodiment 3

[0126] Synthesis of tert-butyl 3-((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)propionate (compound 9):

[0127] To a solution of tert-butyl acrylate (Compound 2) (1.0 mol) in ethanol (250 mL) was added Trizma (Compound 8) (0.1 mol) at 45°C and stirred at the same temperature for 30 hours. Ethanol and excess tert-butyl acrylate were evaporated in vacuo and the resulting residue was recrystallized from hexane and ethyl acetate (3:1) to afford compound 9 as a white solid (90%).

[0128] General method (esterification) of synthetic formula 1 compound

[0129] The fatty acid was added to a stirred mixture of mono-Michael adducts (compounds 3, 6 or 9), DCC and DMAP in anhydrous DCM under a nitrogen atmosphere at room temperature (RT). The resulting reaction mixture was further stirred at room temperature for 18-24 hours. The precipitated dicyclohexylurea was removed by filtration from the reaction mass. The organic layer (filtrate) was evaporated under reduced pressure ...

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Abstract

The invention provides for a synthesised ester intermediate of formula 1. Formula 1 Wherein and wherein R may be a saturated or unsaturated fatty acid (C12-C20).

Description

technical field [0001] The invention relates to a novel pH-responsive lipid and its ester intermediate, its synthesis and application. Background technique [0002] There is a growing demand for pH-responsive lipids in the pharmaceutical industry due to their application in the preparation of pH-responsive drug delivery systems (PSDDS). These drug delivery systems ensure drug delivery at specific sites according to the pathological needs of the disease being treated, thereby enhancing the therapeutic effect. Diseases that use PSDDS include bacterial infections, asthma, peptic ulcers, and cancer. pH-responsive lipids have attracted renewed interest as lipid excipients for the development of targeted drug delivery systems, such as liposomes, vesicles composed of amphiphilic lipids arranged in spherical bilayers, etc. Liposomes can be used to encapsulate various drugs by entrapping hydrophilic drugs within the aqueous interior or between bilayers, or by entrapping hydrophobic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C227/14
CPCC07C229/12A61K9/1272A61K31/675A61K38/14A61K9/127C07C227/16C07C229/16
Inventor T·戈温德M·贾达夫R·卡拉普雷C·莫克塔尔S·K·拉姆巴罗斯
Owner UNIV OF KWAZULU NATAL
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