Method for synthesizing memantine hydrochloride

A technology of memantine hydrochloride and dimethyladamantane, which is applied in the directions of drug combination, amino-substituted functional group preparation, nervous system diseases, etc., can solve the problems of insufficiency, severe reaction, combustion and explosion accidents, etc., to avoid production reduction, Safe and simple operation, avoid the effect of pollution

Inactive Publication Date: 2009-04-22
SUZHOU MACWELL BIOLOGICAL MEDICINE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] (1) Bromine needs to be used in large quantities in production, and at the same time, toxic hydrogen bromide is produced, which has great environmental pollution;
[0010] (2) Acetonitrile and concentrated sulfuric acid are highly toxic, and strong heat and reddish-brown smoke are released during the reaction, the reaction is more violent, and the risk is higher;
[0012] (4) The recrystallization process uses ethanol-ether mixed solvent, which is easy to cause combustion and explosion accidents
[0024] These three methods all need to go through 3-step reactions from the raw

Method used

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  • Method for synthesizing memantine hydrochloride
  • Method for synthesizing memantine hydrochloride
  • Method for synthesizing memantine hydrochloride

Examples

Experimental program
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Embodiment 1

[0047] (1) Take 3.8mL of 1,3-dimethyladamantane (0.02mol), 1.35mL of concentrated nitric acid (0.03mol), 0.334g of N-hydroxy-phthalimide (0.002mol), 5mL Acetic acid was put into a three-necked flask, and the oil bath was slowly heated to 70°C. After 10 hours of reaction, the pH was adjusted to 9 with saturated sodium carbonate solution, extracted three times with ethyl acetate (3×10 mL), and the organic phase was washed with water until neutral. Dry over anhydrous magnesium sulfate. The solvent was evaporated to obtain 3.310 g of crude 1-nitro-3,5-dimethyladamantane;

[0048] (2) Add 10mL of ethanol to the round bottom flask, then add the reactant 1-nitro-3,5-dimethyladamantane crude product and 0.3g of 10% Pd-C obtained in step (1), and remove the air , feed hydrogen, stir at room temperature for 24 hours, filter, distill off ethanol, add petroleum ether to the residue, and filter off insoluble matter;

[0049] (3) Pass dry hydrogen chloride gas into the above-mentioned fil...

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Abstract

The invention discloses a method for preparing memantine hydrochloride, which comprises the following steps: using 1, 3-dimethyl adamantane as a raw material; nitrifying and then reducing the 1, 3-dimethyl adamantane to synthesize an intermediate 1-amino-3, 5-dimethyl adamantane; and acidifying the intermediate by hydrochloric acid and recrystallizing the intermediate by ethanol-ethyl acetate to obtain the memantine hydrochloride through purification,. The method has the advantages of moderate reaction condition, simple post treatment, good safety, low cost and little environment pollution, and suitability for industrialized production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing memantine hydrochloride. Background technique [0002] Memantine hydrochloride (memantine hydrocloride), the chemical name is 3,5-dimethyltricyclic (3,3,1,13,7)-decyl-1-amine hydrochloride, which is developed by German Merz company. Therapeutic drug, noncompetitive antagonism with moderate affinity for N-methyl-D-aspartate receptors, protects nerve cells from the toxic effects of excess excitatory amino acids. Memantine hydrochloride is not only effective for mild Alzheimer's disease (AD), but also can significantly improve the clinical symptoms of severe AD. It can significantly increase the curative effect when used in combination with acetylcholinesterase inhibitors. It is a promising treatment for dementia ( Especially neuroprotective drugs for AD, which were approved by the FDA in 2003 for the treatment of moderate and severe AD. [0003] At present,...

Claims

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Application Information

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IPC IPC(8): C07C211/38C07C209/08A61P25/28
Inventor 敖桂珍黄彬石柳柳于健李静
Owner SUZHOU MACWELL BIOLOGICAL MEDICINE SCI & TECH
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