Hydrobromide of vortioxetine

A compound, crystallization technology, used in the treatment of depression, especially adult major depression drugs, inhibitors of serotonin transporter, crystallization of the drug, 1-[2-phenyl]piperazine hydrobromide in the field of drugs, able to solve problems such as SSRI blockage

Active Publication Date: 2014-10-29
BEIJING LABWORLD BIO MEDICINE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, therapeutic use of SSRIs is hampered by the large number of non-responders, ie patients who do not respond or respond to SSRI therapy to a limited extent

Method used

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  • Hydrobromide of vortioxetine
  • Hydrobromide of vortioxetine
  • Hydrobromide of vortioxetine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0239] Embodiment 1: Preparation of the crystallization (B crystal form) of the compound of formula I

[0240] (1) Dissolve 8 g of vortioxetine free base in toluene, add 1 equivalent of hydrobromic acid (48% hydrobromic acid aqueous solution), stir and crystallize, and filter the precipitate to obtain vortioxetine hydrobromic acid Salt (93%);

[0241] (2) Put 10 g of the product obtained in step (1) into a three-necked flask, add 100 g of toluene and 10 g of water, heat to 85 ° C and stir to dissolve, cool and crystallize, and dry the filtered crystals at 60-70 ° C to obtain hydrogen Vortioxetine bromate (90%);

[0242] (3) Put 1 g of the product obtained in step (2) into a three-necked flask, add 12 g of acetone, stir at 55-60° C. for 30 minutes to form a slurry, then stir at room temperature for 1.5 hours, filter, and vacuum-dry the obtained crystals to obtain It is a crystal of the B crystal form.

[0243] The powder X-ray diffraction figure of above-mentioned step (3)...

Embodiment 2

[0244] Embodiment 2: Preparation of the crystallization (B crystal form) of the compound of formula I

[0245] (1) Dissolve 8 g of vortioxetine free base in toluene, add 1.05 equivalents of hydrobromic acid (47% hydrobromic acid aqueous solution), stir and crystallize, and filter the precipitate to obtain vortioxetine hydrobromic acid Salt (91%);

[0246] (2) Put 10 g of the product obtained in step (1) into a three-necked flask, add 80 g of toluene and 8 g of water, heat to 85 ° C and stir to dissolve, cool and crystallize, and dry the filtered crystals at a temperature of 60-70 ° C to obtain hydrogen Vortioxetine bromate (92%);

[0247] (3) Put 1 g of the product obtained in step (2) into a three-necked flask, add 10 g of acetone, stir at 55-60 ° C for 20 min to form a slurry, then stir at room temperature for 1 hour, filter, and vacuum-dry the obtained crystals to obtain It is a crystal of the B crystal form.

[0248] The powder X-ray diffraction figure of above-mentione...

Embodiment 3

[0249] Embodiment 3: Preparation of the crystallization (B crystal form) of the compound of formula I

[0250] (1) Dissolve 8 g of vortioxetine free base in toluene, add 0.95 equivalent of hydrobromic acid (47% hydrobromic acid aqueous solution), stir and crystallize, and filter the precipitate to obtain vortioxetine hydrobromic acid Salt (92%);

[0251] (2) Put 10 g of the product obtained in step (1) into a three-necked flask, add 120 g of toluene and 12 g of water, heat to 85 ° C and stir to dissolve, cool and crystallize, and dry the filtered crystals at a temperature of 60-70 ° C to obtain hydrogen Vortioxetine bromate (91%);

[0252] (3) Put 1 g of the product obtained in step (2) into a three-necked flask, add 15 g of acetone, stir at 55-60 ° C for 40 min to form a slurry, then stir at room temperature for 2 hours, filter, and vacuum-dry the obtained crystals to obtain It is a crystal of the B crystal form.

[0253] The powder X-ray diffraction figure of above-ment...

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PUM

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Abstract

The invention relates to a hydrobromide of vortioxetine and in particular relates to a crystal of a compound shown in a formula I in the specification. The crystal uses Cu-K alpha radiation. In a powder X-ray diffraction pattern shown by a 2theta angle, diffraction peaks exist at about 6.89 degrees, 9.73 degrees, 13.78 degrees and 14.62 degrees. The invention also relates to a preparation method of the crystal and a drug composition containing the compound. The compound shows the serotonin reabsorption inhibitory activity, has activities towards a serotonin receptor 1A (5-HT1A) and a serotonin receptor 3 (5-HT3), can be used for treating the CNS (central nervous system)-related diseases, and in particular can be used for treating depressive disorder, especially major depressive disorder of adults.

Description

technical field [0001] The present invention relates to a compound which exhibits serotonin reuptake inhibitory activity, and which exhibits serotonin receptor 1A (5-HT 1A ) and serotonin receptor 3 (5-HT 3 ) has activity, and the compound can be used to treat CNS-related diseases. More specifically, the present invention relates to an inhibitor of 5-hydroxytryptamine transporter, which is a drug that can be used to treat depression, especially major depression in adults, and especially relates to a chemical name that can be called 1-[2 -(2,4-Dimethylphenylsulfanyl)phenyl]piperazine hydrobromide, more particularly to the crystallization of said drug. Background technique [0002] Selective serotonin reuptake inhibitors (SSRIs) have been the first-choice therapy for many years for the treatment of certain CNS-related disorders, notably depression, anxiety, and social phobia, due to differences from previously used compounds (ie , traditional tricyclic compounds), these inh...

Claims

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Application Information

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IPC IPC(8): C07D295/096A61K31/495A61K47/26A61P25/00A61P25/24A61P25/28A61P25/18A61P35/00A61P25/16A61P25/22A61P29/00A61P25/30
CPCC07D295/096
Inventor 温光辉解卓峰付冀峰宛六一
Owner BEIJING LABWORLD BIO MEDICINE TECH
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