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A kind of preparation method of ambrisentan

A compound and molar ratio technology, applied in the field of drug synthesis, can solve the problems of severe reaction conditions, influence of the quality and yield of the finished product of Ambrisentan, etc.

Active Publication Date: 2021-12-21
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The final alkali hydrolysis step of this route has severe reaction conditions, which can easily affect the quality and yield of ambrisentan finished products

Method used

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  • A kind of preparation method of ambrisentan
  • A kind of preparation method of ambrisentan
  • A kind of preparation method of ambrisentan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The preparation of embodiment 1 formula Va compound

[0049]

[0050] a) preparation of formula IIIa compound

[0051]

[0052] Add 3L of N,N-dimethylformamide into a 5L three-necked flask, add 300g of the compound of formula II, stir to dissolve; add 457g of anhydrous potassium carbonate, stir for 10min, then add 188g of benzyl bromide, heat to 30-35 The reaction was carried out under temperature control at ℃ for 2 h, followed by TLC until the spots of the compound of formula II disappeared, and the reaction solution of the compound of formula IIIa was directly put into the next reaction without treatment.

[0053] b) preparation of formula Va compound

[0054]

[0055] 256 g of the compound of formula IV were added in batches to the reaction solution of the compound of formula IIIa, stirred and heated to 90-100°C for 3 hours, followed by TLC monitoring until the compound of formula IIIa was completely reacted. The reaction product was extracted and separate...

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Abstract

The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of ambrisentan. In the preparation method, ambrisentan is prepared through benzyl protection reaction, condensation reaction and benzyl protection group removal reaction. Among them, the benzyl-protected intermediate is directly put into the next step of anti-condensation reaction without post-treatment; the debenzylation reaction adopts catalytic hydrogenation, which is green and environmentally friendly, and the reaction operation and post-treatment are simple. After being treated with ether solvent and beating, it can effectively remove the residual raw materials and impurities in the solid. intermediate, obtain the ambrisentan crude product, and then adopt the steps of recrystallization from methanol / water mixed solvent to obtain high-purity ambrisentan. The overall route has few steps and high yield, short production cycle, simple operation, good reproducibility and mild conditions, and is suitable for industrial production.

Description

technical field [0001] The application belongs to the field of drug synthesis, and in particular relates to a preparation method of ambrisentan. Background technique [0002] Ambrisentan is an oral selective endothelin (ET)-A receptor antagonist for the treatment of pulmonary arterial hypertension (PAH). Endothelin is secreted by vascular endothelial cells, and it binds to and activates two types of receptors on the surface of smooth muscle cells: endothelin A and endothelin B (ET-A and ET-B) receptors. Once bound, it causes vasoconstriction and smooth muscle cell growth, proliferation, and possibly increased fibrogenesis. Endothelin receptor antagonists dilate blood vessels and stop unwanted growth and proliferation of cells, resulting in improvement. Pulmonary hypertension will lead to shortness of breath, decreased vitality and shortened life expectancy. Therapeutic effects are produced by inhibiting the action of endothelin. Highly selective endothelin A receptor antag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/34
CPCY02P20/55
Inventor 陈程孟庆义阮宏伟徐洋平
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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