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Preparation method of vilazodone hydrochloride type IV crystal

The technology of vilazodone hydrochloride and vilazodone is applied in the field of preparation of type IV crystal of vilazodone hydrochloride, which can solve the problems of increased production cost, large amount of isopropanol, and poor refining effect , to avoid the effect of oxidative degradation of impurities

Active Publication Date: 2020-09-18
BEIJING JIMEITANG MEDICINE RES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] (1) The amount of isopropanol is extremely large (1g of crude vilazodone requires 77mL of isopropanol);
[0012] (2) The impurities present in the crude product of vilazodone are poorly refined under this condition;
[0013] (3) This preparation method introduces new impurities (oxidized impurities), which requires multiple refinements to obtain APIs with an impurity content of less than 0.1%, resulting in increased production costs

Method used

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  • Preparation method of vilazodone hydrochloride type IV crystal
  • Preparation method of vilazodone hydrochloride type IV crystal
  • Preparation method of vilazodone hydrochloride type IV crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Put the crude vilazodone (10.00g) and sodium metabisulfite (0.05g) in isopropanol (40mL) and DMSO (10ml), stir and heat to 80°C~85°C to dissolve it. After dissolving, add activated carbon (0.5g) and stir at 80°C to 85°C for 30 minutes. After stirring, filter out the activated carbon while it is hot, and rinse the filter cake with isopropanol ketone (10mL). After the filtrate was heated again to 40~50°C, add isopropanol hydrochloride (according to the 1.1eq calculation of the crude product of vilazodone), after the addition was completed, the temperature was raised to 80°C~85°C, and stirred at 80°C~85°C for 3 hours, then lower the temperature to 20°C~30°C, and stir at 20°C~30°C for 1 hour. After suction filtration, the filter cake was rinsed with isopropanol (10 mL), and dried at 70-80°C for 6 hours to obtain 10.32 g of off-white powder crystals (type IV crystals), with a yield of 95.3%.

Embodiment 2

[0026] Put the crude vilazodone (3.50g) and sodium metabisulfite (0.02g) in n-butanol (30mL) and DMSO (5mL), stir and heat to 100°C~110°C to dissolve. After dissolving, slowly lower the temperature to 80°C~90°C, add isopropanol hydrochloride (calculated according to 1.1eq of crude vilazodone), and stir for 2 hours at the same temperature. After suction filtration, the filter cake was rinsed with n-butanol (10 mL), and dried at 70°C to 40°C for 4 hours to obtain 3.56 g of off-white powder crystals (type IV crystals), with a yield of 94.1%.

Embodiment 3

[0028] Put the crude vilazodone (10.00g) and sodium bisulfite (0.05g) in anisole (70mL) and DMF (10mL), stir and heat to 100°C~110°C to dissolve. After dissolving, add isopropanol hydrochloride at 80~90°C. After the addition was complete, the mixture was stirred at the same temperature for 4 hours. After suction filtration, the filter cake was rinsed with anisole (10 mL), and dried at 70-80°C for 6 hours to obtain 10.27 g of off-white powder crystals (type IV crystals), with a yield of 93.2%.

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Abstract

The invention relates to the field of pharmaceutical chemistry and provides a novel preparation method for a vilazodone hydrochloride IV type crystal. The method for preparing the vilazodone hydrochloride IV type crystal is characterized by comprising the following steps: adding a vilazodone crude product and sodium metabisulfite into a crystallization solvent; heating until materials are dissolved; adding isopropanol hydrochloride and carrying out heat insulation and stirring for 0 to 24h under the same temperature; then slowly cooling to certain temperature and carrying out devitrification for 0 to 24h; filtering and washing a filter cake by utilizing an organic solvent; and drying to obtain the vilazodone hydrochloride IV type crystal. Compared with an existing preparation method for the vilazodone hydrochloride IV type crystal, the preparation method provided by the invention can be used for more conveniently obtaining the high-purity vilazodone hydrochloride IV type crystal in a high-yield manner.

Description

technical field [0001] The invention provides a new preparation method of type IV crystal of Vilazodone hydrochloride. In this method, the crude product of vilazodone (vilazodone free base) is dissolved in an organic solvent, and isopropanol hydrochloride is added at a certain temperature, so that vilazodone hydrochloride with high crystal purity can be obtained in high yield Salt type IV crystals. Background technique [0002] On January 21, 2011, the FDA approved Vilazodone hydrochloride (Vilazodone hydrochloride) as a drug for the treatment of major depression in adults, with the trade name Viibryd ® , the specifications are 10mg, 20mg and 40mg. The chemical name of vilazodone hydrochloride is 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofuran Amide hydrochloride, its chemical structural formula is: [0003] [0004] US5532241 belongs to the compound patent of vilazodone, which discloses the preparation method of vilazodone hydrochloride. Usually, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12
CPCC07B2200/13C07D405/12
Inventor 何杰张翔王辉甄志彬刘昆高世静陶新华
Owner BEIJING JIMEITANG MEDICINE RES CO LTD
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