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4-terpineol fatty ester derivate as well as application and preparation method thereof

A technology of fatty acid ester and terpineol, which is applied in the fields of 4-terpineol fatty acid ester derivatives and their application and preparation, can solve the problems of poor reproducibility, unstable content and the like, and achieves easy preservation, enhanced permeability and the like. Ability, the effect of broad application prospects

Inactive Publication Date: 2017-01-04
NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because it is volatile, it will cause unstable content in the formulation and lead to poor reproducibility between batches

Method used

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  • 4-terpineol fatty ester derivate as well as application and preparation method thereof
  • 4-terpineol fatty ester derivate as well as application and preparation method thereof
  • 4-terpineol fatty ester derivate as well as application and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Take 14.8g (0.2mol) of propionic acid, add 17.85g (0.15mol) of thionyl chloride, mix well and react at 60°C for 3 hours, add 20ml of 4-terpineol tetrahydrofuran solution containing 15.4g (0.1mol), The reaction was continued for 3 hours, the reaction solution was adjusted to pH 6-7 with NaOH solution, the organic layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with saturated brine, and anhydrous Na 2 SO 4 Dry overnight, evaporate the solvent, perform column chromatography (silica gel is 200-300 mesh), use ethyl petroleum ether and ethyl acetate (15:1 volume ratio) as the eluent, evaporate the eluent, and obtain 18.64 g of a colorless liquid , Yield: 94%. product of 1 HNMR and MS data are as follows: ESI-MS m / z: 211.3 [M+1]+; 1 H NMR(CDCl3),: 0.90(3H, s), 1.01(3H, s), 1.0(3H, s), 1.25(3H, s), 1.30~1.35(2H, m), 1.40(1H, m) , 1.58~1.60(2H, m), 1.87(1H, m), 2.04(2H, m), 4.78(1H, d, J=11.2 Hz).

Embodiment 2

[0040] Take 17.6g (0.2mol) of butyric acid, add 17.85g (0.15mol) of thionyl chloride, mix and react at 60°C for 3 hours, add 20ml of tetrahydrofuran solution containing 15.4g (0.1mol) of 4-terpineol, The reaction was continued for 3 hours, the reaction solution was adjusted to pH 6-7 with NaOH solution, the organic layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with saturated brine, and anhydrous Na 2 SO 4 Dry overnight, evaporate the solvent, perform column chromatography (silica gel is 200-300 mesh), use petroleum ether and ethyl acetate (15:1 volume ratio) as the eluent, evaporate the eluent, and obtain 20.91 g of a colorless liquid , rate: 92.4%. product of 1 HNMR and MS data are as follows: ESI-MS m / z: 225.3 [M+1] + ; 1 H NMR(CDCl3): 0.90(3H, s), 1.01(3H, s), 0.99(3H, s), 1.25(3H, s), 1.30~1.35(4H, m), 1.41(1H, m), 1.58~1.60(2H, m), 1.88(1H, m), 2.03(2H, m), 4.78(1H, d, J=11.2 Hz).

Embodiment 3

[0042] Take 23.2g (0.2mol) of hexanoic acid, add 17.85g (0.15mol) of thionyl chloride, mix well and react at 60°C for 3 hours, add 20ml of tetrahydrofuran solution containing 15.4g (0.1mol) of 4-terpineol, The reaction was continued for 3 hours, the reaction solution was adjusted to pH 6-7 with NaOH solution, the organic layer was separated, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with saturated brine, and anhydrous Na 2 SO 4 Dry overnight, evaporate the solvent, perform column chromatography (silica gel is 200-300 mesh), use ethyl petroleum ether and ethyl acetate (15:1 volume ratio) as the eluent, evaporate the eluent, and obtain 23.94 g of a colorless liquid , Yield: 93.4%. product of 1 HNMR and MS data are as follows: ESI-MS m / z: 253.4 [M+1] + ; 1 H NMR(CDCl3): 0.90(3H, s), 1.00(3H, s), 1.01(3H, s), 1.24 (3H, s), 1.30~1.35(8H, m), 1.40(1H, m), 1.58~1.60(2H, m), 1.89(1H, m), 2.04 (2H, m), 4.78(1H, d, J=11.2 Hz).

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PUM

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Abstract

The invention belongs to the technical field of medicines and relates to a 4-terpineol fatty ester derivate as well as application and a preparation method thereof. The 4-terpineol fatty ester derivate is obtained by virtue of esterification reaction of 4-terpineol and straight-chain fatty acids. The method comprises the following steps of: reacting fatty acids with sulfoxide chloride to prepare acyl chloride; and then reacting acyl chloride with 4-terpineol to prepare 4-terpineol fatty ester. The 4-terpineol fatty ester serving as a penetration enhancer can be used in a patch, a Cataplasm, an ointment, a gel, and an externally-applied spraying preparation so as to improve the percutaneous absorbed dose of medicines, is a favorable percutaneous-absorption penetration enhancer and has extensive application prospect.

Description

technical field [0001] The invention relates to a derivative and its application and preparation method, especially a 4-terpineol fatty acid ester derivative and its application and preparation method. Background technique [0002] Transdermal drug delivery systems (TDDS) are a new class of preparations in which drugs are absorbed through the skin and enter the systemic circulation to produce curative effects. Once TDDS appeared, it attracted the attention of the medical community due to its long-lasting, constant and controllable blood drug concentration, avoiding the hepatic first-pass effect, convenient administration, and high patient compliance. The skin is a natural barrier that prevents the entry of foreign substances into the body and the loss of body water. The skin is composed of epidermis, dermis and subcutaneous tissue. The epidermis can be divided into stratum corneum and active epidermis. The stratum corneum is the main barrier for drug transdermal absorption....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/14A61K9/70A61K9/00A61K31/137A61K31/167A61K31/192A61K31/216A61K31/405A61K31/138A61K31/34A61K31/196C07C69/145C07C69/24C07C69/58C07C67/14
CPCA61K47/14A61K9/0014A61K9/7023A61K31/137A61K31/138A61K31/167A61K31/192A61K31/196A61K31/216A61K31/34A61K31/405C07C51/60C07C67/14C07C53/40C07C53/42C07C57/66C07C69/145C07C69/24C07C69/58
Inventor 赵利刚李燕王春艳庄鹏宇郑丽娜王慧丽
Owner NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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