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Vortioxetine hydrobromide crystalline form C and preparation method thereof

A technology of vortioxetine hydrobromide and crystal form, applied in the field of medicinal chemistry, can solve the problems of crystal form stability, unsatisfactory preparation method and the like

Inactive Publication Date: 2018-04-24
BEIJING LUNARSUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] In summary, there are many crystal forms of vortioxetine reported in the literature, but they are not satisfactory in terms of crystal stability, preparation methods, etc.

Method used

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  • Vortioxetine hydrobromide crystalline form C and preparation method thereof
  • Vortioxetine hydrobromide crystalline form C and preparation method thereof
  • Vortioxetine hydrobromide crystalline form C and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Put 5.0 g of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine and 50 ml of DMF in a reaction flask, heat and stir to dissolve the solid completely, remove the heating bath, cool to room temperature and wait use;

[0058] Dissolve 625g of ammonium bromide in 1500ml of deionized water with stirring at room temperature, filter out mechanical impurities, add the filtrate to a 3L three-necked flask, cool it down to an internal temperature of 20-25°C while stirring, and add the above solution dropwise (the dropwise addition is completed in 5 minutes) , stirred at 20-25°C for 1.5 hours, filtered with suction, stirred and washed the solid with 150ml of 0°C water, filtered with suction, and washed with 20ml of 0°C water for 4 times to obtain a white solid. Drying under pressure for 5 hours gave 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine hydrobromide hemihydrate crystal form C.

[0059] The prepared crystal form C was subjected to powder diffraction analysis, different...

Embodiment 2

[0063] Put 5.0 g of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine and 50 ml of DMF in a reaction flask, heat and stir to dissolve the solid completely, remove the heating bath, cool to room temperature and wait use;

[0064] Dissolve 625g of ammonium bromide in 1500ml of deionized water with stirring at room temperature, filter out mechanical impurities, add the filtrate into a 3L three-necked flask, cool it to the inner temperature of 0-5°C under stirring, and add the above solution dropwise (the dropwise addition is completed in 5 minutes) , stirred at 0-5°C for 15 hours, filtered with suction, stirred and washed the solid with 150ml of water at 0°C, filtered with suction, and washed with 20ml of water at 0°C for 4 times to obtain a white solid, which was air-dried at room temperature for 20 hours, then reduced to 40°C. Dry under pressure for 5 hours 1-[2-(2,4-Dimethylphenylsulfanyl)phenyl]piperazine hydrobromide hemihydrate crystal form C.

[0065] After testing and v...

Embodiment 3

[0067] Dissolve 625g of ammonium bromide in 1500ml of deionized water with stirring at room temperature, filter out mechanical impurities, add the filtrate to a 3L three-necked flask, cool it to an internal temperature of 5-10°C while stirring, and add solid powder 1-[2-(2, 5.0g of 4-dimethylphenylsulfanyl)phenyl]piperazine, stirred at 5-10°C for 48 hours, filtered with suction, stirred and washed the solid with 150ml of water at 0°C, filtered with suction, and then washed with 20ml of water at 0°C×4 After washing twice, a white solid was obtained, which was air-dried at room temperature for 20 hours, and then dried under reduced pressure at 40°C for 5 hours. 1-[2-(2,4-Dimethylphenylsulfanyl)phenyl]piperazine hydrobromide Compound Form C.

[0068] After testing, its X-ray powder diffraction pattern is as follows: figure 1 The position fluctuations of all characteristic peaks are within the error range, and its DSC spectrum and TGA spectrum are also consistent with figure 2 ...

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Abstract

The invention discloses a novel crystalline form C of vortioxetine hydrobromide hemihydrate, and discloses a preparation method and a pharmaceutical composition of the crystal form C. The powder diffraction pattern of the novel crystalline form C of the vortioxetine hydrobromide hemihydrate contains characteristic peaks at diffraction angles, expressed by 2[theta] + / - 0.20 degrees, of 4.50, 6.10,7.74, 11.10, 12.20, 19.08, 25.20 and 27.62. The novel crystalline form provided by the invention has good solubility, and stable physical and chemical properties, and is suitable for various forms ofpreparations; and the preparation process of the crystalline form is simple, convenient for transformation of industrial scales, and suitable for industrialized production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to vortioxetine hydrobromide crystal form C, a preparation method thereof, a pharmaceutical composition containing a therapeutically effective amount of the compound and a pharmaceutical use thereof. Background technique [0002] Vortioxetine Hydrobromide (Brintellix), chemical name 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine hydrobromide, CAS: 960203- 27-4, the structural formula is as described in formula (I): [0003] (Ι). [0004] Vortioxetine hydrobromide is an inhibitor of serotonin transporter and regulates the activity of its receptors, jointly developed by Lundbeck and Takeda. In September 2013, it was approved by the US Food and Drug Administration (FDA) for the treatment of adult patients with severe depression, and in December of the same year, it was approved by the European Medicines Agency (EMA). Compared with existing antidepressants, vortioxetine has f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/096A61K31/495A61P25/24
CPCC07B2200/13C07D295/096
Inventor 张小波崔东冬张玉良方拥军
Owner BEIJING LUNARSUN PHARMA
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