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Hydrobromide paroxetine-sec-butyl alcohol compound and preparation method thereof

A technology of alcoholate and hydrobromic acid, applied in the direction of organic chemistry, etc., can solve the problems of high desolvation temperature, large particle size, low purity of vortioxetine hydrobromide α crystal form, etc., and achieve desolvation Low melting temperature, high crystal purity, suitable for industrial production

Active Publication Date: 2016-03-30
BEIJING BEILU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The problem to be solved by the present invention is to provide a solution for the low crystal form purity, large particle size and high desolvation temperature during preparation of the vortioxetine hydrobromide α crystal form prepared by the existing method. Vortioxetine hydrobromide-sec-butanolate and preparation method thereof, the sec-butanolate can be used to prepare vortioxetine hydrobromide α crystal form, the desolvation temperature is low during preparation, and energy is saved , and the crystal form of vortioxetine hydrobromide α has high crystal purity, suitable particle size, and is suitable for industrial production

Method used

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  • Hydrobromide paroxetine-sec-butyl alcohol compound and preparation method thereof
  • Hydrobromide paroxetine-sec-butyl alcohol compound and preparation method thereof
  • Hydrobromide paroxetine-sec-butyl alcohol compound and preparation method thereof

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Embodiment 1 1

[0044] The preparation of embodiment 1-sec-butanol compound

[0045] Add 29g of vortioxetine hydrobromide and 524ml of sec-butanol into a 1L reaction flask, heat to 100°C and reflux for 30min, then lower the temperature at a rate of 0.2°C / min until it is cooled to room temperature, filter, and dry at 30°C for 2h. 27.2 g of white solid was obtained. Its X-diffraction, TGA, DSC atlas see Figure 1~3 , and its X-ray powder diffraction data are shown in Table 2.

[0046] X-ray powder diffraction expressed in 2θ angles figure 1 There are characteristic peaks at 6.61±0.2, 13.26±0.2, 15.98±0.2, 17.47±0.2, 19.17±0.2, 19.97±0.2 and 20.64±0.2.

[0047] its TGA figure 2 The thermal weight loss is about 15.11%, which is close to one molecule of sec-butanol, so it is a sec-butanol compound.

[0048] Its DSC image 3 Among them, there are endothermic peaks at 60.2°C, 103.0°C and 226.2°C.

Embodiment 2 1

[0049] The preparation of embodiment 2-sec-butanol compound

[0050] Heat 5 g of vortioxetine hydrobromide and 100 ml of sec-butanol to 100°C and reflux for 30 minutes, then lower the temperature at a rate of 0.5°C / min until cooled to room temperature, filter, and dry at 20°C for 2 hours to obtain 4.8 g of white solid .

Embodiment 3 1

[0051] The preparation of embodiment 3-sec-butanol compound

[0052] Heat 5 g of vortioxetine hydrobromide and 100 ml of sec-butanol to 100°C and reflux for 30 minutes, then lower the temperature at a rate of 0.1°C / min until it cools to room temperature, filter, and dry at 40°C for 2 hours to obtain 4.5 g of white solid .

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Abstract

The present invention discloses a hydrobromide paroxetine-sec-butyl alcohol compound and a preparation method thereof. The present invention provides the hydrobromide paroxetine-sec-butyl alcohol compound as shown in formula I. The present invention further provides the preparation method of the hydrobromide paroxetine-sec-butyl alcohol compound. The preparation method comprises the following steps: mixing hydrobromide paroxetine and sec-butyl alcohol, dissolving, and carrying out crystallization to obtain the hydrobromide paroxetine-sec-butyl alcohol compound. The hydrobromide paroxetine-sec-butyl alcohol compound can be used for preparing Alpha crystalline of the hydrobromide paroxetine, the desolvation temperature is low and the energy resources are saved during preparation, and the Alpha crystalline of the hydrobromide paroxetine is high in purity and appropriate in granularity, and is suitable for industrial production. The formula I is as shown in the specification.

Description

technical field [0001] The invention relates to a vortioxetine hydrobromide-sec-butanol compound and a preparation method thereof. Background technique [0002] [0003] Vortioxetine hydrobromide is developed by the Danish Lundbeck company, and its chemical name is 1-[2-(2,4-dimethyl-phenylthio)-phenyl]piperazine hydrobromide. The structure is shown in the formula 1. The compound has been approved by the US FDA for the treatment of major depressive disorder. Its mechanism may be to play an antidepressant effect by regulating 5-HT, and relevant pharmacological tests have found that the compound is 5-HT 3 , 5-HT 7 , 5-HT 1D Receptor antagonist, 5-HT 1B Partial agonists of receptors, 5-HT 1A receptor agonist. [0004] Vortioxetine hydrobromide exists in various crystal forms, and WO2007144005 reports several of its crystal forms, including: α, β, γ, hydrate, and ethyl acetate solvate. Among them, the melting point of the α crystal form is ~226°C, and the solubility in...

Claims

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Application Information

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IPC IPC(8): C07D295/096
CPCC07D295/096
Inventor 刘帅隋强吴茂诚唐超董继鹏洪承杰
Owner BEIJING BEILU PHARM CO LTD
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