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Agomelatine sulfuric acid composition and preparation method thereof

A technology of agomelatine and compound, applied in the field of agomelatine sulfuric acid compound and preparation thereof

Active Publication Date: 2012-10-03
SHANGHAI RIGHTHAND PHARMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Reports on the crystal form of agomelatine are disclosed in patents such as EP0447285, CN200510071611.6, CN200610108396.7, CN200610108394.8, CN200610108395.2 and CN200910047399.2. In the report of similar complexes, only in CN201010126254.x disclosed agomelatine hydrogen chloride hydrate and its preparation method; CN201010126263.9 disclosed agomelatine hydrogen bromide hydrate and its preparation method; CN201010187158.6 Agomelatine acetic acid solvate was found, and other salts were not reported

Method used

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  • Agomelatine sulfuric acid composition and preparation method thereof
  • Agomelatine sulfuric acid composition and preparation method thereof
  • Agomelatine sulfuric acid composition and preparation method thereof

Examples

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Effect test

Embodiment 1

[0034] Stir and dissolve 10.0g agomelatine in 50mL dichloromethane, add 4.1g concentrated sulfuric acid at 10°C, slowly precipitate crystals under stirring, continue to stir and lower the temperature to 0°C to complete the crystallization; Washed twice with 10 mL of methane, dried at 80°C to obtain 13.4 g of white solid; purity 99.5%, yield: 95.5%. mp: 154.0~158.0°C. KF: 0.465%.

Embodiment 2

[0036] Stir and dissolve 10.0g of agomelatine in 50mL of acetone, add 4.2g of concentrated sulfuric acid (or a pre-configured concentrated sulfuric acid in acetone solution) at 10°C, stir overnight at room temperature to complete the crystallization; filter, and wash the solid with 10mL of acetone Twice, dried at 80°C to obtain 13.6 g of white solid; purity: 99.6%, yield: 96.9%. mp: 154.5~158.0°C. 1 H-NMR (400MHz, d 6 -DMSO): δ 10.88 (s, 2H), 8.21 (s, 1H), 7.82 (d, 1H), 7.70 (d, 1H), 7.61 (s, 1H), 7.32~7.24 (m, 2H), 7.16 (d, 1H), 3.94 (s, 3H), 3.34 (b, 2H), 3.12 (t, 2H), 1.85 (s, 3H). 1 H-NMR (400MHz, d 6 -DMSO+D 2 O): δ 7.80 (d, 1H), 7.69 (d, 1H), 7.56 (s, 1H), 7.32~7.23 (m, 2H), 7.15 (dd, 1H), 3.92 (s, 3H), 3.34 ( t, 2H), 3.12 (t, 2H), 1.84 (s, 3H). KF: 0.620%. S element analysis results: (C 15 h 17 NO 2 ?H2 SO 4 ) Calculated value S% (9.39%), measured value S% (9.23%).

Embodiment 3

[0038] Stir and dissolve 10.0g agomelatine in 20mL of methanol, cool down to 0°C, add 4.1g of sulfuric acid, stir to dissolve, add 40mL of acetone, continue stirring overnight to complete the crystallization; filter, wash the solid twice with 10mL of acetone, 80 Dry at °C to obtain 12.8 g of white solid; purity: 99.8%, yield: 91.2%.

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Abstract

The invention relates to an agomelatine sulfuric acid composition shown in the formula I and a preparation method of the agomelatine sulfuric acid composition. The agomelatine sulfuric acid composition obtained by using the preparation method is good in stability and high in purity, and is suitable for application in finished-product medicinal preparations. The preparation process is also quite simple, so that the product with high purity can be obtained without special operations.

Description

technical field [0001] The invention relates to an agomelatine sulfate complex, a preparation method thereof, and a pharmaceutical component containing the agomelatine sulfate complex. Background technique [0002] Agomelatine, its English name is Agomelatine, its chemical name is N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide, CAS number: [138112-76-2], molecular formula :C 15 h 17 NO 2 , molecular weight: 243.31. Structural formula: [0003] (II) [0004] Agomelatine is a melatonin agonist developed by the French Servier company, which also has the effect of antagonizing 5HT2C receptors, and its trade name is Valdoxan. It is the first melatonin-type antidepressant that can effectively treat depression, improve sleep parameters and not affect sexual function, with fewer sexual adverse reactions. [0005] Reports on the crystal form of agomelatine are disclosed in patents such as EP0447285, CN200510071611.6, CN200610108396.7, CN200610108394.8, CN200610108395.2 and CN200...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/18C07C231/12A61K31/165A61P25/20A61P25/22A61P25/18A61P25/24A61P9/00A61P1/14
Inventor 王海平池骋池正明王进许关煜
Owner SHANGHAI RIGHTHAND PHARMTECH
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