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Preparation method of pimobendan

A technology of pimobendan and methoxybenzaldehyde, which is applied in the field of drug synthesis, can solve the problems of lengthy steps and achieve the best safety effect

Inactive Publication Date: 2017-11-14
蒿莱医药技术(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Comprehensive report At present, all routes basically require more than 10 steps of reaction, the steps are lengthy, and involve dangerous reactions such as nitrification

Method used

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  • Preparation method of pimobendan
  • Preparation method of pimobendan
  • Preparation method of pimobendan

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preparation example Construction

[0038] The invention provides a preparation method of pimobendan, comprising the following steps:

[0039] Step S1: prepare the first intermediate with 2-chloropropionyl chloride, diammonium phthalate and aluminum trichloride, including step S1a: add dropwise 2-chloropropionyl chloride to diammonium phthalate and trichloride In the mixed solution of aluminum, the obtained mixture was refluxed for one hour, and then cooled to 30 degrees to obtain the first mixture; step S1b: adding alcohol and water dropwise to the first mixture, then adding dichloromethane for extraction, washing with water, anhydrous sodium sulfate Dry, filter, spin dry, add petroleum ether, filter to obtain the first intermediate, in this step, prepare the first intermediate with 2-chloropropionyl chloride, diammonium phthalate under the action of Lewis acid and aluminum trichloride Body, which is not limited to the use of aluminum trichloride, aluminum trichloride, iron trichloride, zinc chloride, methanesu...

Embodiment 1

[0049] Step S1: prepare the first intermediate with 2-chloropropionyl chloride, diammonium phthalate and aluminum trichloride, specifically 2-chloropropionyl chloride (9.9g) is added dropwise to the starting material (13 grams) and three In the mixed solution of aluminum chloride (11 grams), the resulting mixture was refluxed for one hour, then cooled to 30 degrees, alcohol and water were slowly added dropwise to the mixed solution, then dichloromethane was added for extraction, washed with water, anhydrous sodium sulfate Dried, filtered, spin-dried, added petroleum ether, and filtered to obtain 8 grams of the first intermediate, which was marked as 1 during the preparation process.

[0050] Step S2: Prepare the second intermediate from the first intermediate, base, N,N-dimethylformamide and malonic acid substituted ester, specifically, in a three-necked flask, add 120 mg of base and N,N-dimethylformamide 6.5 g (half an hour) of malonate substituted ester was slowly added drop...

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Abstract

The present invention relates to the preparation method of pimobendan, comprising the following steps: prepare the first intermediate with 2-chloropropionyl chloride, diammonium phthalate and aluminum trichloride; prepare the first intermediate with the first intermediate, alkali, N,N ‑Dimethylformamide and malonic acid substituted ester prepare the second intermediate; prepare the third intermediate with the second intermediate and a catalytic hydrogenation catalyst; prepare the fourth intermediate with the third intermediate, alcohol and hydrazine hydrate; The fourth intermediate, N,N-dimethylformamide and 4-methoxybenzaldehyde are prepared to obtain pimobendan, and the method of the present invention only needs 5 steps to obtain pimobendan, shortening the current steps more than half, and the starting materials are simple and easy to obtain.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of pimobendan. Background technique [0002] Cardiotonic drug Pimobendna (Pimobendna) was developed by German Boeehringerlngelhem company and was first listed in Japan in 1994. The mechanism of action of this drug is different from that of traditional cardiotonic drugs. Its positive inotropic effect is mainly attributed to the enhancement of the sensitivity of cardiac contractile proteins to calcium ions and the inhibition of phosphodiesterase. Sensitizer drugs. It is clinically used to treat chronic and acute heart failure. In Europe and the United States, the drug is currently mainly used for the treatment of heart failure in pets. The chemical name of this product is: 4,5-dihydro-6-[2-(4-methoxyphenyl-1H-benzoimidazo-5-yl]-5-methyl-3(2H)da Azinonone, its structure is as follows. [0003] The currently reported synthetic routes are as follows: [0004] ...

Claims

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Application Information

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IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 李胜斌
Owner 蒿莱医药技术(上海)有限公司
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