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Method for preparing naftifine hydrochloride

A technology of naftifine hydrochloride and naphthalene methylamine hydrochloride, which is applied in the field of medicine, can solve problems such as poor product quality and difficult purification, and achieve the effects of low cost, simplified operation process, and industrialization

Active Publication Date: 2008-05-28
TIANJIN WEIJIE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The main disadvantage of this method is that the product quality is poor and the purification is difficult.

Method used

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  • Method for preparing naftifine hydrochloride
  • Method for preparing naftifine hydrochloride
  • Method for preparing naftifine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 1.2L methyl tert-butyl ether to a 2L four-necked bottle equipped with a thermometer and mechanical stirring, and add 74.2g (0.36mol) of N-methyl-1-naphthylamine hydrochloride, 123.7g (0.90 mol) anhydrous potassium carbonate and 60g (0.1mol) PEG-600, heat the liquid temperature to reflux, stir and react for 1h, then start to add 60g (0.39mol) of cinnamyl chloride dropwise, the dropwise addition is completed within 4-6h, continue The reaction was stirred under reflux for 8 hours, followed by TLC until N-methyl-1-naphthylmethylamine disappeared, and the reaction was completed. This step can effectively control the generation of impurities in the reaction. Cool down to liquid temperature less than 20°C, filter, wash the filter cake with 50ml of methyl tert-butyl ether, combine the filtrate, add 200ml of hydrogen chloride saturated ethyl acetate solution (mass content is about 8%) dropwise under stirring, stir for a while , until a white solid was precipitated, and the d...

Embodiment 2

[0038] According to the method of embodiment 1, with diethyl ether as reaction solvent, carry out synthesis, obtain naftifine hydrochloride product 97.9g after recrystallization, yield: 84.1%, content ≥ 98% (HPLC normalization method).

[0039] The two comparative examples given below are to use the reaction solvent reported in the literature, adopt the preparation method provided by the invention to produce naftifine hydrochloride, the purpose is to prove the difference and the advantage of the preparation method provided by the invention and the preparation method reported in the literature before.

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Abstract

The invention discloses a preparation method of naftifine hydrochloride, which uses N-methyl-1-naphthyl methylamine hydrochloride as raw material, to directly participate reaction without alkalization free purification, uses organic ether solvent as reaction solvent, in the presence of alkali metal carbonate and catalyst, at suitable temperature, to generate crude naftifine hydrochloride via condensation reaction, and feeds acetic ester saturated solution of hydrochloride to generate hydrochlorate, and obtains high-purity naftifine hydrochloride product via recrystallization. The invention completes alkalization free purification, and condensation reaction in one device, with simple operation, high yield, low foreign material content, low cost, and industrialization support, which is better than previous synthesis method.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to a preparation method of naftifine hydrochloride. Background technique [0002] Naftifine hydrochloride (common name in English: Naftifine Hydrochloride; chemical name: (E)-N-Cinnamyl-N-methyl(1-naphthylmethyl)amine hydrochloride) is a kind of allylamine external antifungal drug, which is effective against hair Sensitive skin fungi such as ringworm, microsporum and epidermophyton are bactericidal, while candida and yeast are bacteriostatic. The mechanism of action of the drug may be to interfere with the biosynthesis of fungal sterols by inhibiting squalene monooxygenase, resulting in a decrease in the number of sterols in cells and accumulation of squalene (enzyme substrate), resulting in the lipids of fungi Metabolic disturbances play a role. Its chemical structural formula is shown in the figure below: [0003] [0004] Four kinds of preparation methods of naftifine hydrochloride ...

Claims

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Application Information

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IPC IPC(8): C07C211/30C07C209/60
Inventor 宋洪海邹阳裴江
Owner TIANJIN WEIJIE PHARMA
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