Carveol ester derivative and percutaneous absorption preparation containing same

A kind of technology of carvitol and derivatives, applied in the field of a class of carvitol ester derivatives and percutaneous absorption preparations containing the derivatives, can solve problems such as not yet seen, achieve easy preservation, enhance permeability Effect

Inactive Publication Date: 2014-01-22
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has not been any research report on the synthesis of new accelerators using carveol as a parent at home and abroad.

Method used

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  • Carveol ester derivative and percutaneous absorption preparation containing same
  • Carveol ester derivative and percutaneous absorption preparation containing same
  • Carveol ester derivative and percutaneous absorption preparation containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take 15.6g (0.12mol) of heptanoic acid and 15.2g (0.1mol) of carveol, add an appropriate amount of p-toluenesulfonic acid and cyclohexane, heat and reflux for 30 minutes, wash the reaction solution three times with water, wash three times with saturated saline, and anhydrous MgSO 4 Dry for 2 hours, evaporate the solvent, and perform column chromatography (silica gel is 200-300 mesh), using petroleum ether and ethyl acetate (100:1) as eluent, to obtain 16.6 g of colorless liquid, yield: 58% . product of 1 HNMR and MS data are as follows: 1 HNMR (CDCl 3 ), δ: 0.893(t, 3H), 1.204~1.387(br, 7H), 1.563~2.339(m, 14H), 4.717~4.754(m, 2H), 5.271~5.749(m, 2H); GC-MS m / z: 264.3[M + ]

Embodiment 2

[0030] Take 17.3g (0.12mol) of octanoic acid and 15.2g (0.1mol) of carveol, add appropriate amount of p-toluenesulfonic acid and cyclohexane, heat and reflux for 30 minutes, wash the reaction solution three times with water, wash three times with saturated saline, and wash with anhydrous MgSO 4 Dry for 2 hours, evaporate the solvent, and perform column chromatography (silica gel is 200-300 mesh), using petroleum ether and ethyl acetate (100:1) as eluent, to obtain 18.3 g of colorless liquid, yield: 62% . product of 1 HNMR and MS data are as follows: 1 HNMR (CDCl 3 ), δ: 0.861(t, 3H), 1.212~1.365(br, 9H), 1.621~2.357(m, 14H), 4.716~4.751(m, 2H), 5.272~5.753(m, 2H); GC-MS m / z: 278.3[M + ]

Embodiment 3

[0032]Take 20.6g (0.12mol) of decanoic acid, 15.2g (0.1mol) of carveol, add appropriate amount of p-toluenesulfonic acid and cyclohexane, heat and reflux for 30 minutes, wash the reaction solution three times with water, wash three times with saturated saline, anhydrous MgSO 4 Dry for 2 hours, evaporate the solvent, and perform column chromatography (silica gel is 200-300 mesh), using petroleum ether and ethyl acetate (100:1) as eluent, to obtain 17.8 g of colorless liquid, yield: 55% . product of 1 HNMR and MS data are as follows: 1 HNMR (CDCl 3 ), δ: 0.889(t, 3H), 1.198~1.387(br, 13H), 1.596~2.353(m, 14H), 4.721~4.754(m, 2H), 5.276~5.754(m, 2H); GC-MS m / z: 306.3[M + ]

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PUM

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Abstract

The invention belongs to the technical field of medicines, discloses a carveol ester derivative and a percutaneous administration preparation containing the derivative, and the structure formula thereof is shown in the specification. The derivative comprises saturated and unsaturated fatty acid carveol ester, wherein fatty acid reacts with carveol ester under the catalytic action of p-toluenesulfonic acid to directly form ester, and anhydrous cyclohexane is taken as a solvent. The carveol ester derivative can be taken as a transdermal enhancer for external preparations such as patch, poultice, ointment, gel and the like, thus improving the percutaneous absorptive amount of medicines, and having higher safety, lower irritation and better medicinal penetration capacity.

Description

technical field [0001] The invention belongs to the technical field of medicine, relates to a class of carverol ester derivatives and transdermal absorption preparations containing the derivatives, in particular to 8 carverol ester derivatives, including saturated and unsaturated fatty acid carverol esters : heptanoic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid carveyl ester and oleic acid carveyl ester, its preparation method and in transdermal preparation (patch, Babu formulations, ointments, gels, creams, etc.). Background technique [0002] Most of the terpenoid accelerators are derived from natural products (volatile oils). They have the advantages of strong penetration-promoting activity, low toxicity, low irritation, and penetration-promoting effects on both hydrophilic and lipophilic drugs. They have become domestic and foreign percutaneous absorption accelerators. One of the hotspots of research. However, the volatilit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/58C07C69/24C07C67/08A61K31/196A61K31/132A61K31/192A61K31/405A61K9/70A61K9/06A61K9/00A61K9/12A61K47/14
Inventor 方亮王曼丽许永男
Owner SHENYANG PHARMA UNIVERSITY
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