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O-anilino benzoic acid derivatives or pharmaceutically acceptable salts thereof as well as preparation method and application thereof

A technology of o-anilino and benzoic acid, applied to o-anilino benzoic acid derivatives or their pharmaceutically acceptable salts, their preparation and their fields of use, can solve problems such as no examples, and achieve easy operation and pain suppression. , the preparation method is simple and effective

Active Publication Date: 2011-03-16
HANGZHOU MINSHENG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although in the patent, tolfenamic acid is also mentioned, but there is no specific example

Method used

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  • O-anilino benzoic acid derivatives or pharmaceutically acceptable salts thereof as well as preparation method and application thereof
  • O-anilino benzoic acid derivatives or pharmaceutically acceptable salts thereof as well as preparation method and application thereof
  • O-anilino benzoic acid derivatives or pharmaceutically acceptable salts thereof as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] [Example 1] Preparation of 2-[(2-chloro-3-methyl-4-nitrophenyl)-amino]benzoic acid (G-1)

[0059] In a 250 ml three-neck flask equipped with an electric stirrer, a thermometer, and a reflux tube, add 8.8 g (43.5 mmol) of o-bromobenzoic acid, 80 ml of n-butanol and 10.4 g of anhydrous potassium carbonate, and stir for 20 minutes; gram of copper powder, 8.8 grams (47.5 mmol) of 4-nitro-3-chloro-2-methylaniline, heating, 90 ° C insulation reaction for 24 hours; cooling to 60 ° C, adding 44 ml of cold water under strong stirring, vacuum filtration , the filtrate was poured into a 250 ml beaker, cooled to 10°C, 15% concentrated hydrochloric acid was added dropwise, and the pH value was adjusted to 3.0; a light yellow solid was precipitated, suction filtered, washed with cold water, and the filter cake was dried; the sample was added to 145 ml Ethanol, heated in a water bath to dissolve, 1.6 g of activated carbon; filtered while hot, cooled the filtrate, and dried with suctio...

Embodiment 2

[0061] [Example 2] Preparation of 2-[(2-chloro-3-methyl-4-aminophenyl)-amino]benzoic acid (G-2)

[0062]50 milliliters of there-necked flasks with electromagnetic stirring, thermometer, reflux tube, add 1.6 grams (5.2 millimoles) G-1 (the sample prepared by the method of embodiment 1), 20 milliliters of water and 0.4 gram of iron powder, stir, add dropwise concentrated Hydrochloric acid 0.4 ml, heating, 90 ° C heat preservation reaction for 24 hours; cooling to 30 ° C, adding 2.2 grams of potassium carbonate under strong stirring, vacuum filtration, pouring the filtrate into a 100 ml beaker, cooling to 10 ° C, adding 15% of Concentrated hydrochloric acid, adjust the pH value to 4.0; Precipitate pale yellow solid, filter with suction, wash with cold water, dry the filter cake; add 13 ml of ethanol, dissolve with water bath heating, 0.7 g of activated carbon; filter while hot, cool the filtrate, and dry with suction 0.8 g of white product was obtained with a yield of 55.6%. The...

Embodiment 3

[0064] [Example 3] Preparation of 4-fluoro-2-[N-(3-chloro--2 methylphenyl)amino]benzoic acid (G-3)

[0065] Add 33 grams (151 mmol) of 4-fluoro-o-bromobenzoic acid, 250 milliliters of n-butanol and 45 grams of anhydrous potassium carbonate to a 500-milliliter three-neck flask equipped with electric stirring, a thermometer, and a reflux tube, stir and heat to 60°C Insulate for 30 minutes; cool to 40°C, pass N2 protection, add 6 grams of copper powder, 40 grams (283 mmol) 3-chloro-2-methylaniline, heat, keep warm at 90°C for 24 hours; cool to 60°C Add 150 ml of cold water while stirring, vacuum filter, pour the filtrate into a 500 ml beaker, cool to 10°C, add 15% concentrated hydrochloric acid dropwise, the pH value reaches 3, a white solid precipitates, filter with suction, wash with cold water, filter cake Drying; 300 ml of ethanol was heated to dissolve, 5 g of activated carbon was hot filtered, the filtrate was cooled with ice water, and 30.3 g of white powder crystals were ...

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Abstract

The invention provides o-anilino benzoic acid derivatives or pharmaceutically acceptable salts thereof as well as a preparation method and applications thereof in preparing medicines or functional food for preventing and / or treating tumors and other abnormal proliferation diseases of organisms and in preparing medicines or functional food for preventing and / or treating inflammations, pains and other diseases of organisms.

Description

(1) Technical field [0001] The present invention relates to o-anilinobenzoic acid derivatives or pharmaceutically acceptable salts thereof, their preparation methods, and their application in the preparation of drugs or functional foods for the prevention and / or treatment of tumors and other body abnormal proliferation diseases, and their use in Application in the preparation of drugs or functional foods for preventing and / or treating diseases such as inflammation and pain in the body. (2) Background technology [0002] Malignant tumor (cancer) is a common and frequently-occurring disease that seriously threatens human health. According to the report of the World Health Organization, in 2008, about 12.4 million people were diagnosed with some type of cancer in the world, and 7.6 million people died of it. The report predicts that by 2010, the death rate of cancer will exceed that of heart disease and become the number one killer in the world; by 2030, there will be 26.4 mil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/58C07C237/30C07C237/40C07C259/10C07C237/32C07C227/08C07C227/18C07C231/02A61K31/196A61K31/245A61K31/166A61K31/167A61P35/00A61P35/02A61P29/00A23L1/29A23L33/00
Inventor 葛求富郭殿武王树龙吴耀东黄滨南张涛杨岚
Owner HANGZHOU MINSHENG PHARM CO LTD
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