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Preparation method of dexmedetomidine hydrochloride for sedation and analgesia in ICU

A technology for dexmedetomidine hydrochloride and sedation, which is applied in the field of preparation of dexmedetomidine hydrochloride, can solve the problems of unsatisfactory splitting yield of a racemate intermediate, and achieves easy industrial production, high yield, high yield, and the like. Step condition mild effect

Inactive Publication Date: 2017-05-31
禚修洁 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a kind of preparation method of the dexmedetomidine hydrochloride that is used for ICU sedation and analgesia, this method can overcome the existing dexmedetomidine hydrochloride synthetic mesobody intermediate split yield is not good ideal question

Method used

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  • Preparation method of dexmedetomidine hydrochloride for sedation and analgesia in ICU
  • Preparation method of dexmedetomidine hydrochloride for sedation and analgesia in ICU

Examples

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Embodiment 1

[0028] Preparation of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole;

[0029] Add 20 g (100 mmol) of racemic 4-[1-(2,3-dimethylphenyl) ethyl]-1H-imidazole and 3 g of sodium sulfate into 100 ml of 1,4-dioxane, and then slowly Raise the temperature to 90°C, add 5.1ml (120mmol) of sulfur trioxide dropwise under stirring, continue the reaction for 1-2 hours, monitor the end of the reaction, concentrate the reaction solution under reduced pressure, wash the concentrate with cold ethanol (0-5°C) 27.6 g of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole was obtained with a yield of 98.4%.

Embodiment 2

[0031] Preparation of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole;

[0032] Add 20 g (100 mmol) of racemic 4-[1-(2,3-dimethylphenyl) ethyl]-1H-imidazole and 3 g of sodium sulfate into 100 ml of 1,4-dioxane, and then slowly Raise the temperature to 90°C, add 5.5ml (130mmol) of sulfur trioxide dropwise under stirring, continue the reaction for 1-2 hours, monitor the end of the reaction, concentrate the reaction solution under reduced pressure, wash the concentrate with cold ethanol (0-5°C) 27.8 g of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole was obtained with a yield of 99.1%.

Embodiment 3

[0034] Preparation of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole;

[0035] Add 200 g (1 mol) of racemic 4-[1-(2,3-dimethylphenyl) ethyl]-1H-imidazole and 2 g of sodium sulfate into 950 ml of 1,4-dioxane, then slowly Slowly raise the temperature to 80°C, add 63ml (1.5mol) of sulfur trioxide dropwise under stirring, continue the reaction for 1-2 hours, monitor the end of the reaction, concentrate the reaction solution under reduced pressure, and use cold ethanol (0-5°C) for the concentrate After washing, 276.7 g of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole was obtained, with a yield of 98.7%.

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Abstract

The invention discloses a preparation method of dexmedetomidine hydrochloride for sedation and analgesia in an ICU. The preparation method comprises the following steps: (1) reacting by virtue of racemic 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole and liquid sulfur trioxide in 1,4-dioxane, so as to obtain sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole; (2) reacting by virtue of sulfonated 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole and (S)-1-phenylethylamine or benzene ring substituted (S)-1-phenylethylamine, so as to obtain (S)-sulfonated-4-[1-(2,3-dimethylphenyl)ethyl]-1H-aminoimidazole; and (3) carrying out dichloromethane extraction in a sodium hydroxide solution, concentrating, and stirring in a hydrochloric acid solution, so as to obtain dexmedetomidine hydrochloride. The preparation method has the beneficial effects that sulfonation is carried out firstly, high-yield chiral phenylethylamine resolution is then carried out to obtain an (S)-product, conditions in each step are mild, and the preparation method is simple, feasible and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to a preparation method of dexmedetomidine hydrochloride used for ICU sedation and analgesia. Background technique [0002] Dexmedetomidine hydrochloride is an α2-adrenoceptor agonist jointly developed by Orion Pharma of Finland and Abott of the United States. It was first launched in the United States in March 2000. Dexmedetomidine hydrochloride has anti-sympathetic, sedative and analgesic effects. Compared with medetomidine, it has stronger selectivity and a shorter half-life. It can be used clinically for intubation and ventilator patients during intensive care treatment At the same time, the drug can also reduce the dosage of anesthetics, improve the stability of hemodynamics during the operation and reduce the incidence of myocardial ischemia. The chemical name of dexmedetomidine hydrochloride is (S)-4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole hydrochloride, and the spec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58
CPCC07D233/58
Inventor 吕燕华
Owner 禚修洁
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