Teprenone and application of derivative of teprenone in preparing drug for treating drug addiction and preventing drug addiction recurrence

A technology of teprenone and derivatives, applied in the field of medicine

A technology of teprenone and derivatives, applied in the field of medicine

CN110893180APending Publication Date: 2020-03-20厦门信力康生物技术有限公司
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  • Teprenone and application of derivative of teprenone in preparing drug for treating drug addiction and preventing drug addiction recurrence
  • Teprenone and application of derivative of teprenone in preparing drug for treating drug addiction and preventing drug addiction recurrence
  • Teprenone and application of derivative of teprenone in preparing drug for treating drug addiction and preventing drug addiction recurrence

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the preparation of all-trans and mono-cis teprenone

[0050] Mix the commercially available teprenone mixture (all-trans isomer: monocis isomer = 3:2) on a silica gel column with n-hexane / ethyl acetate or petroleum ether / ethyl acetate in an appropriate ratio Solvent elution, each component was concentrated on a rotary evaporator to remove the solvent to obtain all-trans teprenone and monocis-teprenone, LCMS: MS (m / z): 333 (MH+); 353 (M+Na). By H-NMR (CDCl 3 ) to determine whether it is an all-trans or a single-cis isomer.

Embodiment 2

[0051] Embodiment 2: the synthesis of all-trans teprenone (reaction formula one)

[0052] All-trans-teprenone can also be synthesized by the method reported in the literature [Bull.Korean Chem.Soc., 2009, 30(9):215-217]. The One-Pot synthesis method reported in this document is shown in the following reaction formula 1. In a round bottom flask was charged geranyllinalool (r-1) (0.30 mL, 0.91 mmol), compound r-2 (0.39 g, 2.28 mmol), p-xylene (4.63 mL) and aluminum isopropoxide (0.019g,

[0053] Reaction formula one,

[0054]

[0055] 0.09 mmol). The reaction flask was placed in an oil bath at 160° C., stirred and heated for 6 hours. The reaction was then cooled to room temperature and the solvent was spun off. A saturated aqueous sodium carbonate solution was added to the residue, followed by extraction with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, concentrated by filtration, and subjected to silica gel column chromatography, and t...

Embodiment 3

[0056] Embodiment 3: Preparation of all-trans and monocis-teprenone mixtures in various weight ratios

[0057] Mix the above-mentioned all-trans teprenone and commercially available teprenone in different proportions to prepare a mixture of teprenone isomers in the required weight ratio, such as all-trans / monocis The ratio of isomers is 7:3, 8:2, 9:1, 9.5:0.5, 9.8:0.2, 9.9:0.1 and so on. Among the four teprenone samples tested, the ratios of all-trans / mono-cis isomers were 10:0, 8:2, 6:4, and 0:10, respectively.

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Abstract

The invention relates to all-trans-teprenone and mono-cis-teprenone and application of a derivative (described as a formula I) of the all-trans-teprenone and mono-cis-teprenone in preparing a drug fortreating drug addiction and preventing drug addiction recurrence. The effects of the all-trans-teprenone (5E-GGA) is superior to the mono-cis-teprenone (5Z-GGA) and also a mixture of an all-trans-teprenone isomer and a mono-cis-teprenone isomer. In a mixture of cis-teprenone and trans-teprenone, the greater the weight ratio of the all-trans-teprenone is, the better the curative effect is.

Description

technical field [0001] The invention relates to the application of teprenone and its derivatives, especially the application of preparing drugs for treating drug addiction and preventing relapse, and belongs to the technical field of medicine. Background technique [0002] Drug addiction is a serious social problem in today's world, with great harm. Common drugs include opioids and amphetamines. Common opioids include morphine, heroin, and opium. Common amphetamine drugs include amphetamine, methamphetamine, ephedrine, methylenedioxymethamphetamine, etc. Drug addiction refers to the formation of mental and physical dependence after drug use, and severe withdrawal symptoms after drug withdrawal. It is a chronic recurrent brain disease. The detoxification usually referred to is composed of three closely related links: detoxification, relapse prevention and social return. Detoxification and relapse prevention are the keys to detoxification. At present, commonly used detoxi...

Claims

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Application Information

Patent Timeline
20 Mar 2020
Publication
CN110893180A
IPC
A61K31/121; A61K31/232; A61K31/22; A61K31/045; A61K31/16; A61K31/10; A61K31/27; A61P25/30; A61P25/36
CPC
A61K31/121; A61K31/232; A61K31/22; A61K31/045; A61K31/16; A61K31/10; A61K31/27; A61P25/30
Inventors
朱锡桢