Stibene derivative organic amine salt, its preparation method, use and medicinal composition

A technology of organic amine salts and organic amines, which is applied in the field of stilbene derivative organic amine salts and their preparation, use and pharmaceutical composition, and can solve the problems of low water solubility of stilbene derivatives, pharmacological action intensity and range limitations, etc. problems, to achieve good curative effect, wide range of pharmacological effects, and definite curative effect

Inactive Publication Date: 2005-04-20
CHONGQING HUAPONT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, due to the extremely low water solubility of stilbene derivatives, the strength and range of their pharmacological effects are limited.

Method used

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  • Stibene derivative organic amine salt, its preparation method, use and medicinal composition
  • Stibene derivative organic amine salt, its preparation method, use and medicinal composition
  • Stibene derivative organic amine salt, its preparation method, use and medicinal composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～7

[0048] The preparation of formula I compound in embodiment 1~7

[0049] The compound of formula I is prepared from the compound of formula II and the compound of formula III through neutralization reaction.

[0050] The compound of formula II used is 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzoic acid, which The structural formula is:

[0051]

[0052] Formula II

[0053] The compound of formula III used is shown in the following table

[0054] Compound of formula III

[0055]

Embodiment 1

[0056] Example 1 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzoic acid 2-hydroxymethyl yl-2-amino-1,3-propanediol salt

[0057] Add 3.5g (10mmol) 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propene in a 250ml three-necked flask Base] benzoic acid, 130ml methanol, 20ml chloroform, heat up and reflux, add 1.21g (10mmol) trimethylolmethylamine after dissolution is complete, insoluble matter is precipitated, heat up and reflux for 2 hours, freeze for 30 minutes after cooling, suction filter, freeze Washed with methanol, recrystallized and dried to obtain 4.4 g of the title compound as a white solid. The yield is 93.8%, and the melting point is 190.5-192.6°C.

[0058] 13 CNMR(DMSO):170.196、144.335、143.774、140.561、139.975、137.826、129.262、128.525、126.464、126.364、123.723、123.414、60.955、60.054、34.942、34.747、34.104、33.865、31.785、31.697、17.504。

[0059] C(％)

Embodiment 2

[0060] Example 2 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzoic acid meglumine salt

[0061] Dissolve 2g of 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]benzoic acid in 110ml of chloroform Dissolve, add 1.15 g of meglumine in 20 ml of DMF dropwise under reflux, and reflux for 1.5 hours after addition, evaporate the oily substance of the solvent to dryness under reduced pressure, add 10 ml of absolute ethanol, dissolve it, and precipitate the solid in the freezer.

[0062] The title compound was obtained as a white solid by suction filtration, and dried to obtain 2.6 g, melting point 212-214°C, yield 85.8%.

[0063] 13 CNMR(DMSO):170.817、144.418、143.836、140.665、138.749、137.765、135.826、129.336、128.545、126.572、126.510、123.802、123.497、71.638、70.954、70.615、69.010、63.713、51.769、35.003、74.810、34.194、33.962 , 33.476, 31.865, 31.786.17.598.

[0064] C(％)

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PUM

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Abstract

The invention relates to an organic amine salt of a stilbene derivative, a preparation method, an application and a pharmaceutical composition thereof. The present invention provides various organic amine salts of stilbene derivatives. Its preparation method is to react stilbene derivatives with ammonia or organic amine compounds to generate corresponding organic amine salts. The compound of the present invention can be used to prepare medicines for preventing and treating tumors and precancerous lesions, and medicines for treating connective tissue diseases or skin diseases; it can be prepared into various oral, injection and external preparations. The water solubility of the compound of the present invention is greatly increased compared with its parent compound stilbene derivative, so the dosage is small and the curative effect is good.

Description

Technical field: [0001] The present invention relates to various organic amine salts of stilbene derivatives, a preparation method thereof and an application for preparing drugs for preventing and treating tumors and precancerous lesions, and preparing drugs for treating connective tissue diseases or skin diseases. The present invention also relates to a pharmaceutical composition containing an organic amine salt of a stilbene derivative. Background technique: [0002] Stilbene derivatives are known antineoplastic drugs. Regarding stilbene derivatives and their preparation methods, GB2010836 first reported (December 21, 1978), and US4326055 on April 20, 1982 further reported their preparation methods and their clinical application prospects. The stilbene derivatives can prevent and treat benign and malignant tumors and precancerous lesions when used locally or systemically, and have significant antitumor effects. This kind of compound can be made into various types of prep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/205A61K31/445A61K31/7008A61P17/00A61P17/06A61P19/02A61P29/00A61P35/00C07C51/41C07C63/08C07C229/26C07D211/06C07H5/06
Inventor 郝光富王永军魏向阳张颖
Owner CHONGQING HUAPONT PHARMA
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