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Novel method for refining dronedarone hydrochloride

A technology of dronedarone hydrochloride and dronedarone, which is applied in the direction of organic chemistry, can solve the problems of large solvent usage, high economic cost and environmental pressure, troublesome operation, etc., achieve mild reaction conditions and avoid debutylation Degradation of impurities and high refining efficiency

Inactive Publication Date: 2018-04-06
BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the operation is cumbersome, and the amount of solvent used is large, the economic cost and environmental pressure are high

Method used

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  • Novel method for refining dronedarone hydrochloride

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Comparison scheme
Effect test

Embodiment 1

[0014] The crude dronedarone hydrochloride (10.00 g) was added to ethyl acetate (50.0 mL), and 1% NaOH aqueous solution (70.0 mL) was slowly added, and stirred until it was completely dissolved. After standing for liquid separation, the organic phase was extracted with ethyl acetate (10.0 mL), and then the organic phases were combined and washed with 10% brine (60.0 mL) once. Add anhydrous sodium sulfate (2.00g) for drying treatment and suction filtration. Under the condition of -10~0℃, slowly add 20% hydrogen chloride ether solution (3.5mL) dropwise to the ethyl acetate solution. After a large amount of solids gradually precipitate in the system, continue to heat and stir for 2 hours. After suction filtration, the filter cake was rinsed with ethyl acetate (10.0 mL) and dried under vacuum at 50°C to obtain a refined dronedarone hydrochloride product (8.61 g) with a yield of 86%. The product liquid phase purity and main impurity content are shown in Table 1.

Embodiment 2

[0016] The crude dronedarone hydrochloride (10.00g) was added to 2-methyltetrahydrofuran (50.0mL), and 1% NaOH aqueous solution (70.0mL) was slowly added, and stirred until the dissolution was complete. After standing for liquid separation, the organic phase was extracted with 2-methyltetrahydrofuran (10.0 mL), and then the organic phases were combined and washed with 10% brine (60.0 mL) once. Add anhydrous sodium sulfate (2.00g) for drying treatment and suction filtration. Under the condition of 0~10℃, slowly add a 20% hydrogen chloride isopropanol solution (3.5mL) dropwise to the 2-methyltetrahydrofuran solution. After a large amount of solids gradually precipitate in the system, continue to heat and stir for 2 hours. After suction filtration, the filter cake was rinsed with 2-methyltetrahydrofuran (10.0 mL) and dried under vacuum at 50°C to obtain a refined dronedarone hydrochloride product (9.00 g) with a yield of 90%. The product liquid phase purity and main impurity cont...

Embodiment 3

[0018] The crude dronedarone hydrochloride (10.00 g) was added to ethyl acetate (50.0 mL), 1% KOH aqueous solution (100.0 mL) was slowly added, and the solution was stirred until it was completely dissolved. After standing for liquid separation, the organic phase was extracted with ethyl acetate (10.0 mL), and then the organic phases were combined and washed with 10% brine (60.0 mL) once. Add anhydrous sodium sulfate (2.00g) for drying treatment and suction filtration. Under the condition of 20~30℃, slowly dropwise add 20% hydrogen chloride ethyl acetate solution (3.5mL) to the ethyl acetate solution. After a large amount of solids gradually precipitate in the system, continue to keep the temperature and stir for 2 hours. After suction filtration, the filter cake was rinsed with ethyl acetate (10.0 mL) and dried under vacuum at 50°C to obtain a refined dronedarone hydrochloride product (8.10 g) with a yield of 81%. The product liquid phase purity and main impurity content are ...

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Abstract

The invention provides a novel method for refining dronedarone hydrochloride. According to the method, by virtue of a salt removing and forming manner, impurities can be effectively removed. Moreover,de-butyl degradation impurities are not produced, and the refined dronedarone hydrochloride with high purity is obtained.

Description

Technical field [0001] The invention provides a new method for refining dronedarone hydrochloride. The method adopts the method of dissolving salt into salt, first dissolving salt under alkaline conditions to form a free alkali solution, then dripping hydrogen chloride solution to form salt, cooling and crystallization to obtain pure dronedarone hydrochloride, which can effectively remove impurities. And will not generate de-butyl degradation impurities. Background technique [0002] Dronedarone hydrochloride, chemical name is N-[2-butyl-3-[4-(3-dibutylaminopropoxy)benzoyl]-5-benzofuranyl]methan Sulfonamide hydrochloride, its chemical structure is (StructureI): [0003] . [0004] Dronedarone hydrochloride is a new type of drug for the treatment of atrial fibrillation. Its chemical structure is similar to that of the standard drug amiodarone for the treatment of atrial fibrillation, and the mechanism of action is the same. Both are potassium channel blockers. Developed by the Fr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80
CPCC07D307/80
Inventor 张翔桂星星刘昆高世静陶新华
Owner BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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