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Preparation method and applications of vortioxetine hydrobromide degradation product

A technology of vortioxetine hydrobromide and a determination method, applied in the field of medicine, can solve problems such as complicated operation, inability to meet quality research, long reaction steps and the like

Active Publication Date: 2017-12-05
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The disadvantage of this route is: (1) the reaction steps are long, and column chromatography is used for many times to separate, which is cumbersome to operate; (2) the purity of the obtained formula I compound is only about 96%, which cannot meet the needs of quality research
[0013] Since there are no relevant toxicity research reports on the compound of formula I in the literature at home and abroad, in the absence of toxicity research data to support its harmlessness to the human body, in order to ensure the safety of medication, the inventors have found a synthetic method for the compound of formula I. And the method for using the compound of formula I in the quantitative detection of vortioxetine hydrobromide impurity

Method used

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  • Preparation method and applications of vortioxetine hydrobromide degradation product
  • Preparation method and applications of vortioxetine hydrobromide degradation product
  • Preparation method and applications of vortioxetine hydrobromide degradation product

Examples

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Embodiment 1

[0065] This example is used to illustrate the preparation of the compound of formula I of the present invention.

[0066] Add the compound of formula II (15g, 0.05mol) and 180ml of formic acid into a 500ml four-necked reaction flask, stir to dissolve, add hydrogen peroxide (17.1g, 0.15mol), react at 20-30°C for 6 hours, add 300ml of ammonia water dropwise, and stir for 1 After 1 hour, the crude product was obtained by filtration, and the crude product was refined with 100 ml of ethyl acetate to obtain 13.3 g of a white solid with a yield of 84.2% and an HPLC content of 99.5%.

Embodiment 2

[0068] This example is used to illustrate the preparation of the compound of formula I of the present invention.

[0069] Add the compound of formula II (15g, 0.05mol) and 180ml of acetic acid into a 500ml four-necked reaction flask, stir to dissolve, add hydrogen peroxide (11.4g, 0.1mol), react at 20-30°C for 9 hours, add 300ml of ammonia water dropwise, and stir for 1 hours, the crude product was obtained by filtration, and the crude product was purified with 100 ml of ethyl acetate to obtain 12.8 g of a white solid with a yield of 81% and an HPLC content of 99.8%.

Embodiment 3

[0071] This example is used to illustrate the preparation of the compound of formula I of the present invention.

[0072] Add the compound of formula II (15g, 0.05mol) and 180ml of trifluoroacetic acid into a 500ml four-necked reaction flask, stir to dissolve, add hydrogen peroxide (34g, 0.3mol), react at 20-30°C for 4 hours, add 300ml of ammonia water dropwise, and stir After 1 hour, the crude product was obtained by filtration, and the crude product was purified with 100 ml of ethyl acetate to obtain 13 g of a white solid with a yield of 82.3% and an HPLC content of 99.7%.

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Abstract

The present invention provides a preparation method of a compound represented by a formula I, and applications of the compound in detection of the related substance content in vortioxetine hydrobromide. The preparation method comprises: dissolving a compound represented by a formula II in an organic acid, adding hydrogen peroxide, carrying out a reaction for 2-20 h, and treating to obtain the compound represented by the formula I. According to the present invention, the research results of the compound show that the compound can provide the reference substance for the qualitative and quantitative analysis of the vortioxetine hydrobromide impurity so as to effectively improve the quality control standard of vortioxetine hydrobromide, and ensure the safe medication. The formulas I and II are defined in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, relates to a preparation method of a compound and its application, in particular to a preparation method of a degradation product of vortioxetine hydrobromide, and the quantitative determination of related substances of vortioxetine hydrobromide by the compound in the application. Background technique [0002] Vortioxetine hydrobromide was jointly developed by Takeda Pharmaceutical Co., Ltd. of Japan and Lundbeck Pharmaceutical Co., Ltd. of Denmark. It was launched in Europe in October 2013 for the treatment of severe depression in adults. [0003] Vortioxetine hydrobromide is thought to act through a combination of dual mechanisms of action: modulation of receptor activity and inhibition of reuptake. In vitro studies have shown that vortioxetine can inhibit 5-HT reuptake, with 5-HT 1A Agonists, 5-HT 1B Receptor partial agonists, 5-HT 3 , 5-HT 1D , 5-HT 7 Function of receptor antagonists, ...

Claims

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Application Information

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IPC IPC(8): C07D295/096G01N30/88
CPCC07D295/096G01N30/88G01N2030/884
Inventor 方思萌康江鹏苏慕君潘毅陈蔚
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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