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Preparation method of agomelatine I crystal form

A technology of crystal form and crystal plane spacing, which is applied in the field of medicine, can solve the problems of poor reproducibility and unsuitability for industrial production, and achieve the effect of simple operation and good reproducibility

Active Publication Date: 2010-12-22
NHWA PHARMA CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a preparation method of agomelatine I crystal form in order to overcome the problems of poor reproducibility and unsuitability for industrial production of the existing methods for preparing agomelatine I crystal form

Method used

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  • Preparation method of agomelatine I crystal form
  • Preparation method of agomelatine I crystal form
  • Preparation method of agomelatine I crystal form

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Form I of N-(2-(7-methoxy-1-naphthyl)ethyl)-acetamide

[0038]2 grams of agomelatine sample was added to the flask, followed by a mixed solvent of 2ml N,N-dimethylformamide (DMF) and 3ml water, heated to dissolve, filtered to remove insoluble matter, and the filtrate was cooled to 0 in an ice bath. °C, a solid precipitated out. Suction filtration after 0.5 hours, the filter cake was washed twice with water, dried by suction, and dried in vacuum at 30°C for 12 hours to obtain 1.8 g of agomelatine I crystal form sample with a yield of 90% and a purity of 99.2%. Its DSC spectrum is shown in figure 1 , X-ray powder diffraction pattern see figure 2 .

Embodiment 2

[0039] Example 2: Form I of N-(2-(7-methoxy-1-naphthyl)ethyl)-acetamide

[0040] Add 2 grams of agomelatine sample into the flask, then add 3ml of N,N-dimethylacetamide and 2ml of water to form a mixed solvent, heat to dissolve, filter out insoluble matter, and slowly cool the filtrate to 10 °C, a solid precipitated out. Suction filtration after 3 hours, the filter cake was washed twice with water, dried by suction, and dried under vacuum at 50°C for 12 hours to obtain 1.85 g of agomelatine I crystal form sample with a yield of 92.5% and a purity of 99.7%. Its DSC spectrum is shown in figure 1 , X-ray powder diffraction pattern see figure 2 .

Embodiment 3

[0041] Example 3: Form I of N-(2-(7-methoxy-1-naphthyl)ethyl)-acetamide

[0042] Add 2 grams of agomelatine sample into the flask, then add 3mL of N,N-dimethylformamide and 3mL of water as a mixed solvent, heat to dissolve, then filter with suction to remove insoluble matter, and cool the filtrate in an ice bath At 5°C, a solid precipitated out. Suction filtration after 2 hours, the filter cake was washed twice with water, dried by suction, and dried under vacuum at 40°C for 12 hours to obtain 1.78 g of agomelatine I crystal form sample with a yield of 89% and a purity of 99.5%. Its DSC spectrum is shown in figure 1 , X-ray powder diffraction pattern see figure 2 .

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Abstract

The invention discloses a preparation method of an agomelatine I crystal form, which comprises the steps of: adding agomelatine into a mixed solvent of amide and water, heating for dissolving, then reducing the temperature and separating out crystals, and drying to obtain a solid. The agomelatine is dissolved in the heated mixed solvent of the amide and water, and separated out slowly in a cooled mixed solvent of the amide and water, and the high-purity I crystal form can be stably obtained. The method has the advantages of high purity of reaching above 99 percent of the single crystal form, simple operation and good repeatability, and the like and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of agomelatine crystal form. Background technique [0002] The chemical name of agomelatine is N-(2-(7-methoxy-1-naphthyl)ethyl)-acetamide, and its chemical structure is shown in (1) below. The trade name is valdoxan. [0003] [0004] Agomelatine (agomelatine) was first developed by the French company Servier and was launched in Germany and the UK in 2009 for the treatment of depression. It has a dual mechanism of action, on the one hand it is a melatonin 12 (MT1MT2) receptor agonist and on the other hand it is a serotonin 2c (5HT2c) receptor antagonist. These properties render it central nervous system active, particularly active in the treatment of major depression, seasonal affective disorder, sleep disorders, cardiovascular conditions, digestive conditions, insomnia and fatigue due to jet lag, appetite disorders and obesity. Patent EP0447285 dis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/18C07C231/24
Inventor 陈道鹏马彦琴徐增波李春明彭卫娟张桂森
Owner NHWA PHARMA CORPORATION
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