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4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt, its preparation method and application

A technology of benzamidophenoxy and methylcarbamoyl, applied in the field of chemical medicine, can solve the problems of low solubility, hinder the timely absorption of drugs, and low absolute bioavailability of oral administration, and achieve high solubility and bioavailability. high effect

Inactive Publication Date: 2011-09-28
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine has antitumor activity, but its solubility is extremely small, which hinders the timely absorption of the drug, Oral absolute bioavailability is low
There are no related reports about 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridinium salt

Method used

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  • 4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt, its preparation method and application
  • 4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt, its preparation method and application
  • 4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt, its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Example 1 Preparation of 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine hydrochloride

[0046] 1. Dissolve 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine in ethanol, add hydrochloric acid solution, and adjust pH=2.

[0047] 2. Filter and recrystallize the residue from ethyl acetate and water.

Embodiment 2

[0048] Example 2 Preparation of 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine 4-methylbenzenesulfonate

[0049] Suspend N-methyl-4-(4-(3-trifluoromethyl)benzamido)phenoxy)pyridinecarboyl in ethyl acetate and heat to 70°C to dissolve. Within 3 minutes, a mixture of p-toluenesulfonic acid, ethyl acetate and water was added dropwise, and the reaction was heated. Cooled and filtered, rinsed the resulting solid with ethyl acetate, dried under reduced pressure to obtain 66.1g (90% yield) 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-( Methylcarbamoyl)pyridine 4-methylbenzenesulfonate crude product.

[0050] The crude 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine 4-methylbenzenesulfonate was recrystallized from ethyl acetate and water to obtain Refined products, the identification data of refined products are as follows:

[0051] 1 H-NMR (DMSO-d 6 )δ: 2.29 (3H, s), 2.81 (3H, d, J = 4.8Hz), 6.15 (1H, s), 7.12 (2H, d, J = 8.0Hz), 7.23 ...

Embodiment 3

[0057] Example 3 Preparation of 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine 4-methylbenzenesulfonic acid crystal form B

[0058] 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridine 4-methylbenzenesulfonate was added to a clean 2L three-necked flask, and then Add ethyl acetate into the three-necked flask. Install the condenser and thermometer. Turn on stirring and heating. When the temperature rose to 70°C, deionized water was added dropwise into the three-necked flask. After about 3 minutes, the reaction system was completely dissolved. Filtrate hot, add 200ml ethyl acetate, air cool down naturally, stir and crystallize. After 2 hours, the reaction system was filtered to obtain a white solid. The solid was rinsed with ethyl acetate and sucked dry. Drying under reduced pressure gave 59.1 g of solid product (yield 89.6%).

[0059] Melting point: 200.0-203.0°C; product purity measured by HPLC: 99.4765%; crystal drying weight loss...

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Abstract

The invention relates to 4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt, its preparation method and an application, which belongs to the chemical medicine field. The structure of 4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt is shown as a formula I, X can be one of hydrochloric acid, acetic acid, benzoic acid, benzene sulfonic acid, citric acid, fumaric acid, glucurnic acid, malic acid, maleate, C1-C8 alkyl substituted sulfonic acid, naphthoic acid, nitric acid, oleic acid, oxalic acid, phosphoric acid, succinic acid, tartrate, sulfuric acid, C1-C8 alkyl substituted benzene sulfonic acid, ethanolamine, trifluoroacetic acid, lactic acid, dinaphthyl salicylic acid or asccharin. 4-(4-(3-trifluoro methyl) benzamido phenoxyl)-2-(methyl carbamyl) pyridine salt of the present invention has the advantages of high solubility and high bioavailability, which can be used for preparing medicines to treat cancer.

Description

technical field [0001] The invention relates to 4-(4-(3-trifluoromethyl)benzamidophenoxy)-2-(methylcarbamoyl)pyridinium salt and its preparation method and application, belonging to the field of chemical medicine. Background technique [0002] Malignant tumors have become the second leading cause of human death, seriously threatening human health. In my country, according to the latest statistics, tumors have become the number one cause of death for our people. According to the latest epidemiological survey data, there are more than 3 million cancer patients in my country, and about 1.3 million patients die of malignant tumors every year. Every year, there are 1.6 to 2 million new cases of malignant tumors, and they are increasing at a rate of 3%, which poses a huge threat to the life and health of our people and brings huge pressure to society and families. To a certain extent, it restricts the sustainable economic development of our country. Traditional tumor treatment met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81C07C309/30C07C303/32A61K31/4412A61P35/00
Inventor 余洛汀赵瀛兰宋相容杨胜勇魏于全
Owner SICHUAN UNIV
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