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Synthesis method of nalmefene hydrochloride

A synthetic method, the technology of nalmefene, which is applied in the field of organic chemical synthesis, can solve the problems of long synthesis time, cumbersome methods, and poor safety

Inactive Publication Date: 2021-09-07
WUXI JIMIN KEXIN SHANHE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] CN102584840A-A method for preparing nalmefene compound, which takes a long time for synthesis
[0006] CN103012416A-a method for purifying nalmefene in a preparation method of high-purity nalmefene hydrochloride, the method is relatively cumbersome
[0007] CN104513251A-a preparation method of nalmefene hydrochloride and a purification method of nalmefene, the method is cumbersome and uses toxic reagents in the synthesis process, which has poor safety

Method used

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  • Synthesis method of nalmefene hydrochloride
  • Synthesis method of nalmefene hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1, nalmefene hydrochloride (this case is a preferred case)

[0045] Dry the four-necked flask, add 300ml of tetrahydrofuran, add 26g of potassium tert-butoxide and 64g of methyl triphenylphosphine bromide successively under stirring, stir at room temperature for 3.5 hours, then add 13.6g of naltrexone hydrochloride, protect with nitrogen, and heat The temperature was 35°C and refluxed for 5 hours; the reaction was quenched with saturated ammonium chloride and diluted with 200ml of purified water. Separation, the aqueous phase was extracted twice with 300ml ethyl acetate, the organic phases were combined, and concentrated under reduced pressure to a viscous liquid; add 100ml of chloroform to dilute, then add concentrated hydrochloric acid 36% and stir to form a salt, filter to obtain white or light yellow sodium hydrochloride Meifen solid powder.

[0046] Take 13 g of nalmefene hydrochloride solid powder, add 4 ml of purified water and 40 ml of ether, stir we...

Embodiment 2

[0047] Embodiment 2, nalmefene hydrochloride

[0048] Dry the four-necked flask, add 300m tetrahydrofuran, add 26g potassium tert-butoxide and 64g methyl triphenylphosphine bromide successively under stirring, stir at room temperature for 3.5 hours, then add 13.6g naltrexone hydrochloride, nitrogen protection, heat The temperature was 35°C, and the mixture was refluxed for 5 hours; the reaction was quenched by saturated ammonium chloride, and diluted with purified water. Separate the liquid, extract the aqueous phase twice with ethyl acetate, combine the organic phases, and concentrate under reduced pressure to a viscous liquid; add chloroform to dilute, then add concentrated hydrochloric acid to stir to form a salt, and filter to obtain a light yellow solid powder of nalmefene hydrochloride.

[0049] Take 12g of nalmefene hydrochloride solid powder, add 12g of purified water, heat to dissolve at 85°C, filter, cool down to room temperature naturally, then continue to cool down...

Embodiment 3

[0050] Embodiment 3, nalmefene hydrochloride

[0051] Dry the four-necked flask, add 300m tetrahydrofuran, add 26g potassium tert-butoxide and 64g methyl triphenylphosphine bromide successively under stirring, stir at room temperature for 3.5 hours, then add 13.6g naltrexone hydrochloride, nitrogen protection, heat The temperature was 35°C, and the mixture was refluxed for 5 hours; the reaction was quenched by saturated ammonium chloride, and diluted with purified water. Separate the liquid, extract the aqueous phase twice with ethyl acetate, combine the organic phases, and concentrate under reduced pressure to a viscous liquid; add chloroform to dilute, then add concentrated hydrochloric acid to stir to form a salt, and filter to obtain a light yellow solid powder of nalmefene hydrochloride.

[0052] The solid powder of nalmefene hydrochloride was taken and treated with 25ml of chloroform×3 to prepare a yellow crystalline solid with a yield of 89%.

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Abstract

The invention relates to a synthesis method of nalmefene hydrochloride, wherein the synthesis method comprises the following steps: (1) taking an organic solvent, sequentially adding potassium tert-butoxide and methyl triphenyl phosphorus bromide while stirring, stirring for 3.5 h at a room temperature, adding naltrexone hydrochloride, and carrying out a reaction under nitrogen protection; and (2) quenching the reaction mixture with ammonium chloride, and diluting with water; and standing, separating a water phase and an organic phase, extracting the water phase by using ethyl acetate, combining an ethyl acetate extracting solution and the organic phase, and concentrating under reduced pressure to obtain a viscous liquid; (3) adding chloroform into the viscous liquid to dilute, then adding concentrated hydrochloric acid, stirring to form salt, and filtering to obtain white or faint yellow nalmefene hydrochloride crude product powder; and (4) taking the nalmefene hydrochloride crude product, adding purified water and an organic solvent, fully stirring, filtering, and carrying out forced air drying to obtain a white crystalline solid.

Description

technical field [0001] The invention relates to an organic chemical synthesis method, in particular to a method for synthesizing nalmefene hydrochloride with naltrexone hydrochloride. [0002] technical background [0003] Nalmefene hydrochloride preparations are mainly used clinically for anti-shock and neuroprotection, treatment of hepatic encephalopathy, acute alcoholism, acute toxic coma, chronic respiratory failure, treatment of acute poisoning of morphine drugs, and prevention of relapse in drug addicts. Awakening from anesthesia rescues respiratory depression and other central nervous system depression symptoms, and can quickly recover the comatose; it can also be used for heart failure, spinal cord injury, brain protection, etc. Nalmefene is another pure opioid receptor antagonist synthesized after naloxone and naltrexone. Its unique chemical structure makes it show stronger physiological activity and easier to penetrate biomembrane. It is a new generation of opioid ...

Claims

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Application Information

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IPC IPC(8): C07D489/08
CPCC07D489/08
Inventor 王晓霞於江华朱音过晓磊毛菊红
Owner WUXI JIMIN KEXIN SHANHE PHARMA
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