Method for preparing memantine hydrochloride

A technology of memantine hydrochloride and dimethyladamantane, which is applied in the field of senile dementia treatment drugs, can solve the problems of easy to cause combustion and explosion accidents, high ventilation performance requirements, easy environmental pollution, etc. The effect of recycling, low cost and convenient operation

Inactive Publication Date: 2004-04-14
JIANGSU INST OF NUCLEAR MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The first step in the above-mentioned method adopts bromination, because hydrogen bromide gas is produced in the reaction process, it is easy to cause harm to the human body, and it is easy to cause pollution to the environment, so the reaction process has high requirements on the ventilation performance of the equipment, and the redundant bromine reduction; Chinese patent CN1335299, CN1400205 also use 1-bromo-3,5-dimethyladamantane as raw material to prepare this product, and there is also a technical problem of bromination; Acetonitrile and concentrated sulfuric acid have strong heat and reddish-brown s

Method used

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  • Method for preparing memantine hydrochloride
  • Method for preparing memantine hydrochloride
  • Method for preparing memantine hydrochloride

Examples

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Embodiment 1

[0024] Synthesis of 1-chloro-3,5-dimethyladamantane:

Embodiment 2

[0027] Synthesis of 1-Acetylamino-3,5-Dimethyladamantane:

[0028] Add 147.3g of 1-chloro-3,5-dimethyladamantane and 380.5g of acetamide obtained in the previous step (Example 1) into a 1000ml round-bottomed flask. The heating temperature is controlled at 20~120℃, and the reaction is refluxed under stirring. After 3 hours, pour into 1000ml of water, stand still overnight, precipitate a solid, filter with suction, wash with water, and dry to obtain 151.3g of crude product, which is recrystallized with petroleum ether to obtain 145.9g of white needle-like crystals. The two-step yield totaled 89.0%. The melting point is 113.5-114.5°C.

Embodiment 3

[0030] Synthesis of 1-amino-3,5-dimethylamantadine hydrochloride:

[0031] Add 12.2g sodium hydroxide and 350ml glycerol to a 1000ml round bottom flask, heat to 100~110℃, stir and reflux until the sodium hydroxide is completely dissolved, the solution gradually turns black, add 145.9g after the sodium hydroxide is dissolved 1- Acetylamino-3,5-dimethyladamantane is heated to 150-160°C under stirring and reflux, and the reaction is continued at this temperature for 6 hours. After the reaction was cooled to room temperature, it was poured into ice water, extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, filtered with suction, and concentrated to obtain a yellow oil as 1-amino-3,5- Crude dimethylamantadine. Dry hydrogen chloride gas was passed through under stirring, and solid was precipitated. The solid was filtered by suction. The obtained solid was recrystallized with ethanol-ethyl acetate (3:5v / v) mixed solve...

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Abstract

The invention is a manufacturing method of diamante amine hydrochlorate. The invention adopts 1, 3-dimethyl adamantine to reacts with tert-butylchlorine and gets 1-chlorine-3, 5-dimethyl adamantine; then reacts with acetamide directly, the educt from water reacts with sodium hydroxide in ethanediol or glycerine solvent, extracts by acetic ester, condenses, and blow in dry hydrochloride gas and gets the coarse product. There gets the pure product through alcohol-acetic ester recrystallization.

Description

Technical field [0001] The invention relates to a preparation method of a drug for treating Alzheimer's disease (AD) and an N-methyl-D-aspartic acid (NMDA) receptor antagonist memantine hydrochloride. Background technique [0002] Memantine hydrochloride, its chemical name: 1-amino-3,5-dimethyladamantane hydrochloride, structural formula: [0003] [0004] Because its structure contains amino groups, it is usually called memantine hydrochloride. It is the first NMDA antagonist developed by Merz to have a significant effect on AD. It acts on the glutamine system in the brain and is a non-competitive NMDA antagonist with medium affinity. Clinical studies have shown that memantine hydrochloride is well tolerated in AD patients, and it also has a significant effect on severe AD. Acetylcholinease inhibitors can only be used for moderate AD, and there are no reports of drugs that have been proven to treat severe AD. At present, there are about 5 million AD patients in China, so it ca...

Claims

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Application Information

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IPC IPC(8): A61P25/28C07C209/58C07C211/38
Inventor 周杏琴项景德曹国宪胡名扬杨敏钦晓锋
Owner JIANGSU INST OF NUCLEAR MEDICINE
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