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A kind of flupenthixol derivative and preparation method thereof

A technology of flupenthixol and synthetic method, applied in the field of drug synthesis

Active Publication Date: 2020-01-31
西安康远晟生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, there are antidepressant and anti-anxiety effects

Method used

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  • A kind of flupenthixol derivative and preparation method thereof
  • A kind of flupenthixol derivative and preparation method thereof
  • A kind of flupenthixol derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Preparation of compound 9-(1-hydroxy-3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)-2-(trifluoromethyl)-9H-sulfanthene fumarate

[0031] Weigh 217.08mg (0.5mmol) of flupenthixol into a round bottom flask, dissolve it with 30mL of acetone, add 1.27mg (0.005mmol) of osmium tetroxide and 10.43mg (0.045mmol) of silver oxide, and stir thoroughly at 5°C After 3 hours of reaction, the catalyst was removed from the reaction solution with mercapto silica gel to obtain intermediate 1, which weighed 156.44 mg (about 0.336 mmol, and the yield was 67.12%; As for the malic acid in the reactor, add 20 mL of ethanol, stir at room temperature for 0.5 h, evaporate the ethanol under reduced pressure, add 30 mL of acetone to the residue, heat to dissolve, decolorize with activated carbon for 0.5 h, filter, add 20 mL of ether to the filtrate, Stir vigorously under ice-water cooling for 3 hours, crystals precipitate out, filter, wash with a mixed solution (acetone: ether = 3:2), and dry in vacu...

Embodiment 2

[0033] Preparation of compound 9-(1-hydroxy-3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)-2-(trifluoromethyl)-9H-sulfanthene fumarate

[0034] Weigh 217.08mg (0.5mmol) of flupenthixol into a round bottom flask, dissolve it with 30mL of DMSO, add 1.27mg (0.005mmol) of osmium tetroxide and 10.43mg (0.045mmol) of silver oxide, and fully stir the reaction at 0°C After 4 h, the catalyst was removed from the reaction solution with mercapto silica gel to obtain intermediate 1, which weighed 140.20 mg (about 0.300 mmol, and the yield was 60.15%; the reaction intermediate 1 and 69.61 mg (about 0.600 mmol) As for the malic acid in the reactor, add 20 mL of ethanol, stir at room temperature for 0.5 h, evaporate the ethanol under reduced pressure, add 30 mL of acetone to the residue, heat to dissolve, decolorize with activated carbon for 0.5 h, filter, add 20 mL of ether to the filtrate, Stir vigorously under ice-water cooling for 3 hours, crystals precipitate out, filter, wash with a mixed...

Embodiment 3

[0036] Preparation of compound 9-(1-hydroxy-3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)-2-(trifluoromethyl)-9H-sulfanthene fumarate

[0037] Weigh 217.08mg (0.5mmol) of flupenthixol into a round bottom flask, dissolve it with 30mL of acetone, add 1.91mg (0.0075mmol) of osmium tetroxide and 11.59mg (0.05mmol) of silver oxide, and stir thoroughly at 5°C After 3 hours of reaction, the catalyst was removed from the reaction solution with mercapto silica gel to obtain intermediate 1, which weighed 147.30 mg (about 0.316 mmol, and the yield was 63.12%; As for the malic acid in the reactor, add 20 mL of ethanol, stir at room temperature for 0.5 h, evaporate the ethanol under reduced pressure, add 30 mL of acetone to the residue, heat to dissolve, decolorize with activated carbon for 0.5 h, filter, add 20 mL of ether to the filtrate, Stir vigorously under ice-water cooling for 3 hours, crystals precipitate out, filter, wash with a mixed solution (acetone: ether = 3:2), and dry in vacu...

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Abstract

The invention discloses a flupentixol derivative and a preparation method thereof. The preparation method is characterized in that flupentixol serves as a raw material, is subjected to catalytic oxidation by osmium tetroxide and silver oxide in an organic solvent and is subjected to salifying with fumaric acid so as to form the flupentixol derivative which is novel in structure. The flupentixol derivative can be used as a flupentixol prodrug and has various biological activities for treating schizophrenia, resisting depression, resisting anxiety and the like. The method has the advantages thatthe reaction steps are few, the operation is simple and feasible, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a flupenthixol derivative and a preparation method thereof, belonging to the technical field of drug synthesis. Background technique [0002] Flupenthixol has a strong antipsychotic effect. As an atypical antipsychotic drug, its hydrochloride salt form is commonly used clinically, which is a thioxanthene derivative and has a powerful blocking effect on dopamine receptors. In addition to blocking D1 and D2 receptors, it can also inhibit D2 autoreceptors and increase the concentration of DA in the synapse. The antipsychotic effect is 4 to 8 times stronger than Telden and the sedative effect is weaker. In addition, there are antidepressant and anti-anxiety effects. Clinically, it can be used for acute and chronic schizophrenia, depression and depressive neurosis. It is suitable for negative symptoms of schizophrenia such as apathy and withdrawal. It also has a certain effect on anxiety and lack of motivation. Its capric acid est...

Claims

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Application Information

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IPC IPC(8): C07D495/10C07C51/41C07C57/15A61P25/18A61P25/22A61P25/24
CPCA61P25/18A61P25/22A61P25/24C07D495/10
Inventor 梁承远鞠星可田蕾夏娟周军辉李菡丁顺军贾敏一
Owner 西安康远晟生物医药科技有限公司
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