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Aminocomprolizine derivatives and their applications

A technology of amino and drugs, which is applied in the synthesis of anticancer drug compounds, aminocompritine derivatives and their synthesis, and preparation fields, which can solve the problems of reduced human tolerance, increased toxicity, and unsuitable clinical use.

Active Publication Date: 2022-08-02
YIWUHUAYAO PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have shown that after the amino acid modification of amino acid CA-4, the toxicity of the molecule will be greatly increased, and the tolerance of the human body will be reduced, so it is not suitable for clinical use.

Method used

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  • Aminocomprolizine derivatives and their applications
  • Aminocomprolizine derivatives and their applications
  • Aminocomprolizine derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (Z)-1-(3,4,5-trimethoxyphenyl)-2-(3-(bis(2-n-propyl)amino)propionamide)-4-ethoxyphenyl)ethene synthesis

[0052]

[0053] Step 1: Synthesis of trimethoxybenzyltriphenylphosphine bromide

[0054] Dissolve 320 g of 3,4,5-trimethoxybenzyl alcohol in 2L of toluene, stir to dissolve, and then cool down to -5 to 0 °C, add 100 ml of phosphorus bromide dropwise to a constant pressure dropping funnel, and keep the reaction temperature at -5 to 0 °C. After the dropwise addition was completed, the reaction was continued at low temperature for 2 hours, and then returned to room temperature, and the reaction was performed overnight.

[0055] Add 1.4 L of purified water to quench the reaction, stir for 30 min, and let stand for separation. The upper organic phase was washed with saturated sodium bicarbonate solution to pH 7.5-8, dried over anhydrous magnesium sulfate and filtered to obtain a toluene solution of trimethoxybenzyl bromide.

[0056] Add 0.56kg of triphenylphosphoru...

Embodiment 2

[0066] (Z)-1-(3,4,5-Trimethoxyphenyl)-2-((3-(bis(2-n-propyl)amino)propionamide)-4-ethoxyphenyl)ethene Preparation of hydrochloride

[0067]1 g of (Z)-1-(3,4,5-trimethoxyphenyl)-2-((3-(bis(2-n-propyl)amino)propionamide)-4-ethoxyphenyl ) Ethylene was dissolved in 10 ml of methanol, 0.2 ml of hydrochloric acid was added, heated to 35 °C and stirred for 1 h. After cooling, it was concentrated to dryness, 10 ml of water was added, stirred for 10 min, and then allowed to stand overnight. Suction filtration, the obtained white filter cake is (Z)-1-(3,4,5-trimethoxyphenyl)-2-((3-(bis(2-n-propyl)amino)propane) after freeze-drying amide)-4-ethoxyphenyl)ethylene hydrochloride.

Embodiment 3

[0069] (Z)-1-(3,4,5-Trimethoxyphenyl)-2-((3-(bis(2-n-propyl)amino)propionamide)-4-methoxyphenyl)ethene preparation

[0070]

[0071] Step 1: Synthesis of trimethoxybenzyltriphenylphosphine bromide

[0072] Dissolve 320 g of 3,4,5-trimethoxybenzyl alcohol in 2L of toluene, stir to dissolve, and then cool down to -5 to 0 °C, add 100 ml of phosphorus bromide dropwise to a constant pressure dropping funnel, and keep the reaction temperature at -5 to 0 °C. After the dropwise addition was completed, the reaction was continued at low temperature for 2 hours, and then returned to room temperature, and the reaction was performed overnight.

[0073] Add 1.4 L of purified water to quench the reaction, stir for 30 min, and let stand for separation. The upper organic phase was washed with saturated sodium bicarbonate solution to pH 7.5-8, dried over anhydrous magnesium sulfate and filtered to obtain a toluene solution of trimethoxybenzyl bromide.

[0074] Add 0.56kg of triphenylphosp...

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Abstract

The present invention discloses aminocompridin derivatives, specifically compounds represented by general formula (I), and pharmaceutically acceptable salts thereof, as well as hydrates thereof or hydrates of pharmaceutically acceptable salts thereof, and Its solvate or the solvate of its pharmaceutically acceptable salt, and its isomer, the general formula (I) structural formula is as follows: wherein, R 1 is selected from C1-C3 alkyl or C1-C3 haloalkyl; R 2 , R 3 are independently selected from C1-C6 alkyl, C1-C6 haloalkyl, or C1-C6 alcohol. The present invention also relates to the use of these compounds in the preparation of medicaments for treating diseases caused by abnormal neovascularization and tubulin aggregation inhibitors.

Description

technical field [0001] The invention belongs to the field of synthesis and preparation of pharmaceutical compounds, in particular to the synthesis and preparation of anti-cancer pharmaceutical compounds, and more particularly to aminocompridine derivatives and a synthesis method and application thereof. Background technique [0002] Combretastatins series compounds were originally extracted and isolated from the trunk of Combretumcaffrum in South Africa, and the series of compounds have a cis-1,2-stilbene structure. Among them CombretastatinA-4, namely CA-4 (cis-1-(3,4,5-trimethoxy)phenyl-2-(3'-hydroxy-4'-methoxy)phenylethylene) has the most Strong inhibition of microtubule polymerization. In 1997, T.Hatanaka et al. of Ajinomoto Co., Ltd. of Japan discovered that the anticancer activity was greatly improved by transforming the hydroxyl group at the 3' position of CA-4 into an amino group. However, the water solubility of Combretastatins series compounds is very poor, espec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/08A61P35/00A61P35/02A61K31/167C07C231/12C07C231/02C07C233/25C07C213/02C07C217/84C07C201/12C07C205/37C07C41/22C07C43/225C07F9/54
CPCC07C237/08A61P35/00A61P35/02C07C231/12C07C231/02C07C233/25C07C213/02C07C217/84C07C201/12C07C205/37C07C41/22C07C43/225C07F9/5456C07B2200/09C07C237/04A61K31/167
Inventor 王建平
Owner YIWUHUAYAO PHARM TECH CO LTD
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