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Synthesis method of tranilast

A synthetic method, the technology of special methyl ester, which is applied in the field of chemical synthesis and can solve the problems of high cost and low yield

Inactive Publication Date: 2015-06-10
药大制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problems of low yield and high cost in the preparation process of tranilast in the prior art, the invention provides a synthetic method of tranilast

Method used

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  • Synthesis method of tranilast
  • Synthesis method of tranilast
  • Synthesis method of tranilast

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Tranilast production method of the present invention is as follows:

[0033] raw material:

[0034]

[0035] resolve resolution:

[0036] 1. Preparation of 3,4-dimethoxycinnamic acid: Weigh 117g of malonic acid and dissolve it in 200ml of dry pyridine. After stirring evenly, add 125g of 3,4-dimethoxybenzaldehyde and heat up to 90°C , react for 2 to 3 hours, after the reaction, cool slightly, pour the reaction liquid into 500ml of ice water, adjust the pH to 2 to 3 with concentrated hydrochloric acid, a large amount of solid precipitates, let stand, filter with suction, wash the filter cake with ice water until the filtrate The pH was 5-6 and dried to obtain 146 g of solid.

[0037] 2. Preparation of tranilast methyl ester: Weigh 146g of 3,4-dimethoxycinnamic acid and dissolve it in 700ml of dichloromethane, add 158g of DCC under stirring, cool the reaction solution to 0-5°C, and add in batches 105g of methyl anthranilate, stirred and reacted for 1h, reacted at roo...

Embodiment 2

[0040] raw material:

[0041]

[0042] Synthetic method is identical with example 1.

[0043] 1. Preparation of 3,4-dimethoxycinnamic acid: Weigh 234g of malonic acid and dissolve it in 470ml of dry pyridine. After stirring evenly, add 250g of 3,4-dimethoxybenzaldehyde and heat up to 90°C , react for 2 to 3 hours, after the reaction, cool slightly, pour the reaction solution into 800ml ice water, adjust the pH to 2 to 3 with concentrated hydrochloric acid, a large amount of solid precipitates, let stand, filter with suction, wash the filter cake with ice water until the filtrate The pH was 5-6 and dried to obtain 280 g of solid.

[0044] 2. Preparation of tranilast methyl ester: Weigh 280g of 3,4-dimethoxycinnamic acid and dissolve it in 1.4L of dichloromethane, add 305g of DCC under stirring, cool the reaction solution to 0-5°C, batch Add 205g of methyl anthranilate, stir and react for 1h, react at room temperature for 5-6h, filter to remove DCU, remove dichloromethane f...

Embodiment 3

[0047] raw material:

[0048]

[0049] In the synthetic method, the solvent in step 1 is changed to toluene, and the others are the same as in Example 1.

[0050] 1. Preparation of 3,4-dimethoxycinnamic acid: Weigh 150g of malonic acid and 780ml of pyridine and dissolve them in 800ml of dry toluene. After stirring evenly, add 160g of 3,4-dimethoxybenzaldehyde and heat up to 90°C, react for 7-8 hours, after the reaction, cool slightly, pour the reaction solution into 1.5L of ice water, adjust the pH to 2-3 with concentrated hydrochloric acid, a large amount of solid precipitates, let stand, filter with ice, and filter the cake with ice Wash with water until the pH of the filtrate is 5-6, and dry to obtain 150 g of solid.

[0051] 2. Preparation of tranilast methyl ester: Weigh 150g of 3,4-dimethoxycinnamic acid and dissolve in 720ml of dichloromethane, add 163g of DCC under stirring, cool the reaction solution to 0-5°C, and add in batches 109g of methyl anthranilate, stirr...

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Abstract

The invention provides a method for preparing tranilast. The method is that 3, 4-dimethyl benzaldehyde is used as a starting material subjected to condensation reaction with malonic acid by pyridine catalyzing to synthesize 3, 4-dimethoxycinnamic acid; the 3, 4-dimethoxycinnamic acid is condensed with methyl anthranilate to generate tranilast methyl ester; the tranilast methyl ester is hydrolyzed through sodium hydroxide to obtain tranilast. The total yield of tranilast is up to 67%. The method is short in process line, simple to operate, high in yield, low in production cost, stable, reliable, and simple to operate; the high-purity tranilast raw medicine can be obtained with high yield; the production cost can be completely reduced; the emission of pollutants can be decreased.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of tranilast. Background technique [0002] Tranilast (I), the chemical name is N-(3,4-dimethoxycinnamoyl) anthranilic acid, the appearance is light yellow crystalline powder, odorless, sweet and sour taste. Insoluble in water, easily soluble in hot ethanol, with a melting point of 212-213°C. Molecular formula: C 18 h 17 NO 5 Molecular weight: 327.34, its molecular structure is: [0003] [0004] Tranilast is an allergic mediator blocker, which can inhibit the degranulation of mast cells and the release of allergic mediators caused by allergens and other stimuli. It has the function of stabilizing the cell membrane of mast cells and basophils, preventing their degranulation. Thereby inhibiting the release of histamine and 5-hydroxytryptamine allergic reaction substances, and has a significant inhibitory effect on rat skin allergic reactions ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/38C07C231/12
Inventor 王卉李永韧华峰倪滨斌叶文江陈飞超
Owner 药大制药有限公司
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