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Preparation method of memantine salt

A technology for amantadine salt and memantine, which is applied in the field of preparing memantine salt, can solve the problems of difficult control of process operation, product quality, difficulty, many side reactions, etc., achieves cheap raw materials, avoids danger, and simplifies reaction effect of steps

Active Publication Date: 2007-09-26
ZHUHAI UNITED LAB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This "one-pot method" carries out multi-step reactions in the same container, and there are many side reactions, and it is difficult to control the process operation and product quality. According to the technical information provided by this patent, combined with our many years of experience in pharmaceutical research and development and production, It is found that it is difficult to achieve industrial production of this process

Method used

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  • Preparation method of memantine salt
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  • Preparation method of memantine salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of 1-acetamido-3,5-dimethyladamantane:

[0033] 1,3-Dimethyladamantane (82.0g, 0.5mol), acetamide (236.0g, 4mol), Br 2 (640.0g, 4mol) after mixing evenly, stir and react at reflux temperature for 5h. After the reaction is completed, add 200ml of acidified ice water (pH=1), add sodium thiosulfate to remove bromine, and adjust the pH value with 5% NaOH aqueous solution 8 to 9, then extracted twice with ethyl acetate (200mL), combined the ethyl acetate extracts, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to remove the solvent, and the obtained solid was decomposed with ethanol solution Recrystallized and dried to obtain 94.1g white 1-acetamido-3,5-dimethyladamantane, yield: 85.2%, mp: 111-112°C, purity (GC) 99.5%, 1 HNMR (CDCl3, 400Hz) δ: 0.82 (6H, s), 1.13 (2H, m), 1.25 (4H, q, J = 12.5Hz), 1.58 (4H, m, J = 11.4Hz), 1.77 (2H, s), 1.84 (3H, s), 2.11 (1H, t), 5.19 (1H, s), MS (m / z): 221.

[0034] T...

Embodiment 2

[0037] Preparation of 1-carboxamido-3,5-dimethyladamantane:

[0038] 1,3-Dimethyladamantane (16.4g, 0.1mol), formamide (36g, 0.8mol), Br 2 (128g, 0.8mol) after mixing evenly, stir and react at reflux temperature for 12h. After the reaction is completed, add 50ml of acidified ice water (pH=1), add sodium thiosulfate to remove bromine, and adjust the pH value with 5% NaOH aqueous solution 8 to 9, then extracted with ethyl acetate 50mL×2, combined the ethyl acetate extracts, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to remove the solvent, and obtained a yellow viscous liquid without purification , used directly in the next reaction.

[0039] The preparation of memantine hydrochloride:

[0040] Take the reaction solution obtained above, add 50mL of ethanol and 20mL of 36.5% hydrochloric acid, stir and reflux for 6h, the reaction process is monitored by gas chromatography, after the reaction, adjust the pH value to 8-...

Embodiment 3

[0042] Preparation of 1-aminoamido-3,5-dimethyladamantane:

[0043] 1,3-Dimethyladamantane (16.4g, 0.1mol), urea (36g, 0.8mol), Br 2 (128g, 0.8mol) after mixing evenly, stir and react at reflux temperature for 12h. After the reaction is completed, add 50ml of acidified ice water (pH=1), add sodium thiosulfate to remove bromine, and adjust the pH value with 5% NaOH aqueous solution 8 to 9, then extracted with ethyl acetate 50mL×2, combined the ethyl acetate extracts, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to remove the solvent, and obtained a yellow viscous liquid without purification , used directly in the next reaction.

[0044] The preparation of memantine hydrochloride:

[0045] Take the reaction solution obtained above, add 50mL of ethanol and 20mL of 36.5% HCl, stir and reflux for 6h, and monitor the reaction process by gas chromatography. After the reaction, concentrate the solvent to dryness, add 50mL o...

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Abstract

The invention discloses a new making method of amantadine, which comprises the following steps: adopting 1, 3-dimethyl adamantane as raw material to do halogenation and Ritter reaction; separating and purifying the make 1-subtituted-amido-3, 5-dimethyl diamantine as intermediate; hydrolyzing the intermediate into diamantine; extracting; obtaining rough product; recrystallizing the rough product to obtain the fined product; fitting for industrial manufacturing.

Description

technical field [0001] The invention relates to the field of pharmaceutical products, in particular to a method for preparing memantine salt. technical background [0002] [0003] Memantine (Memantine hydrochloride, 1) is a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist. Memantine hydrochloride is an old drug. In 1982, Akatinol was first launched in Germany under the trade name of Merz for the treatment of dementia, and it has been launched in other countries one after another. Later, companies such as Merz, Lundbeck, and NTI used the drug in the treatment research of Alzheimer's disease (Alzheimer's disease, AD) and AIDS-related dementia. On February 20, 2002, the European Patent Medicines Committee (CPMP) approved memantine hydrochloride from Lundbeck Company (transferred from Merz Company) for the treatment of moderate and severe presenile dementia patients. In August 2002, memantine hydrochloride was launched in Germany under the trade name Axura....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/34C07C209/62
Inventor 刘毓宏韩石左斌海唐彬喜彭韪
Owner ZHUHAI UNITED LAB
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