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A kind of method for preparing flupirtine hydrochloride

A technology for flupirtine hydrochloride and fluorobenzylaminopyridine, which is applied in the field of chemical drug preparation, can solve the problems of Raney nickel being inflammable, undisclosed reaction conditions, and high risk, so as to avoid deterioration, reduce production costs, and reduce injuries Effect

Active Publication Date: 2022-03-29
SICHUAN QINGMU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The literature only provides a route for the synthesis of intermediate 2-amino-3-nitro-6-p-fluorobenzylaminopyridine derivatives, and does not disclose specific reaction conditions
In addition, the high-risk material Raney nickel is used in the catalytic hydrogenation reaction. Raney nickel is flammable and highly dangerous.

Method used

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  • A kind of method for preparing flupirtine hydrochloride
  • A kind of method for preparing flupirtine hydrochloride
  • A kind of method for preparing flupirtine hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Add 2,6-dichloro-3-nitropyridine (50g, 259.1mmol) into a reaction kettle containing 200ml of methanol, add 25% ammonia water (145.3g, 1.036mol) at room temperature, and control the internal temperature to 30-35 ℃, heat preservation reaction for about 7 hours, TLC monitors that the reaction of the raw materials is complete and stops the reaction, adds p-fluorobenzylamine (38.9g, 310.8mmol), raises the temperature to 75~80℃ and reacts for about 4 hours, TLC monitors that the reaction of the raw materials is complete, then stops the reaction, and cools down to Crystallize at 5-10°C for 1-2 hours and then filter. The obtained wet product was added to 940ml of n-propanol and heated to reflux to dissolve, cooled to room temperature for crystallization for 2 hours, filtered, and the wet product was kept in the reaction kettle. Add 750ml of n-propanol, 1.0g of 5% Pd / C and ethyl chloroformate (30g, 276.5mmol) into the reaction kettle, feed hydrogen gas to keep the pressure at 1....

Embodiment 2

[0038] Add 2,6-dichloro-3-nitropyridine (50g, 259.1mmol) into a reaction kettle containing 250ml of ethanol, add 25% ammonia water (109.0g, 777.5mmol) at room temperature, and control the internal temperature at 35-40 ℃, heat preservation reaction for about 6 hours, TLC monitors that the reaction of the raw materials is complete and stops the reaction, adds p-fluorobenzylamine (38.9g, 310.8mmol), raises the temperature to 55~60℃ and reacts for about 7 hours, TLC monitors that the reaction of the raw materials is complete and then stops the reaction, and cools down to Crystallize at 5-10°C for 1-2 hours and then filter. The obtained wet product was added to 630ml of methanol and heated to reflux to dissolve, cooled to room temperature for crystallization for 2 hours, filtered, and the wet product was kept in the reaction kettle. Add 800ml of isopropanol, 2g of 5% Pd / C and ethyl chloroformate (30g, 276.5mmol) into the reaction kettle, feed hydrogen gas to keep the pressure at 1....

Embodiment 3

[0040] 2,6-Dichloro-3-nitropyridine (50g, 259.1mmol) was added to a reaction kettle equipped with 300ml of n-propanol, 25% ammonia water (76.3g, 544.1mmol) was added at room temperature, and the internal temperature was controlled at 30 ~35°C, keep warm for about 6 hours, TLC monitors that the reaction of the raw materials is complete, then stop the reaction, add p-fluorobenzylamine (38.9g, 310.8mmol), raise the temperature to 60~65°C and react for about 6h, TLC monitors that the reaction of the raw materials is complete, then stop the reaction, Cool down to 5-10°C and crystallize for 1-2 hours, then filter. The obtained wet product was added to 760ml of ethanol and heated to reflux to dissolve, cooled to room temperature for crystallization for 2 hours, filtered, and the wet product was kept in the reaction kettle. Add 800ml of n-propanol, 5g of 5% Pd / C and ethyl chloroformate (30g, 276.5mmol) into the reaction kettle, feed hydrogen gas to keep the pressure at 1.8-2.0MPa, and...

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Abstract

The invention discloses a method for preparing flupirtine hydrochloride, which specifically adopts 2,6-dichloro-3-nitropyridine as a starting material, undergoes ammonolysis, replaces p-fluorobenzylamine, purifies, and simultaneously hydrogenates, Acylation reaction, filtration, crystallization, and drying under reduced pressure to obtain flupirtine hydrochloride. The method of the invention is simple to operate, and the hydrogenation and acylation reactions are carried out at the same time, so that the deterioration of the polyaminopyridine derivatives can be avoided as far as possible, and the ethyl chloroformate is added dropwise without opening the lid of the kettle, thereby reducing the harm to the human body.

Description

technical field [0001] The application belongs to the technical field of chemical drug preparation, and in particular relates to a method for synthesizing flupirtine hydrochloride. Background technique [0002] Flupirtine maleate, chemical name: 2-amino-3-acylethoxyamino-6-p-fluorobenzylpyridine maleate, molecular formula: C 19 h 21 FN 4 o 6 ; Molecular weight: 420.21; Its structural formula is as follows: [0003] [0004] Flupirtine maleate is a central non-opioid analgesic developed by German AWD company. It is a triaminopyridine compound. Its mechanism of action is: flupirtine maleate is a selective central potassium ion Channel opener, which also has indirect aspartate (NMDA) receptor antagonist properties, can activate G-protein coupled receptors to stimulate potassium ion channels in nerve cells, resulting in hyperpolarization of nerve cell membranes and neuronal excitation The sex is reduced, which stabilizes the resting nerve cell membrane to achieve the pur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/89
CPCC07D213/89
Inventor 邵波卢铁刚李晓迅胡同军任良王颖
Owner SICHUAN QINGMU PHARMA CO LTD
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