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Agomelatine benzenesulfonic acid compound and preparation method thereof

A technology of agomelatine besylate and complex, applied in the field of agomelatine besylate compound and its preparation

Active Publication Date: 2013-08-14
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 benzenesulfonic acid compound and preparation method thereof
  • Agomelatine benzenesulfonic acid compound and preparation method thereof
  • Agomelatine benzenesulfonic acid compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Stir and dissolve 10.0g agomelatine in 50mL dichloromethane, add 6.5g benzenesulfonic acid at room temperature, slowly precipitate crystals under stirring, continue stirring and lower the temperature to 10°C to complete the crystallization; Washed twice with 10 mL of methane, dried at 80°C to obtain 15.6 g of white solid; purity 99.5%, yield: 94.5%. mp: 131.0~136.0℃. 1 H-NMR (400MHz, CD 3 OD)δ 7.84~7.87 (m, 2H), 7.78 (d, 1H), 7.69 (d, 1H), 7.49 (d, 1H), 7.44~7.47 (m, 3H), 7.33 (d, 1H), 7.27 (t, 1H), 7.15 (dd, 1H), 3.98 (s, 3H), 3.60 (t, 2H), 3.28 (t, 2H), 2.09 (s, 3H).

Embodiment 2

[0033] Stir and dissolve 10.0g agomelatine in 50mL of acetone, add 6.5g of benzenesulfonic acid at 10°C, stir overnight to complete the crystallization; filter, wash the solid with 10mL of acetone twice, and dry at 80°C to obtain a white solid 15.4 g; purity 99.6%, yield: 93.3%. mp: 133.0~135.0℃. In addition, the above experiment was repeated. After the reaction liquid was stirred evenly, the stirring was stopped, and it was allowed to stand overnight. The crystals were precipitated the next day, and the single crystals were selected to determine the structure by X-ray diffraction.

Embodiment 3

[0035] Stir and dissolve 10.0g agomelatine in 20mL of methanol, cool down to 0°C, add 6.5g of benzenesulfonic acid, stir to dissolve, add 40mL of acetone, continue stirring overnight to complete the crystallization; filter, and wash the solid twice with 10mL of acetone , dried at 80°C to obtain 15.0 g of white solid; purity: 99.8%, yield: 90.9%. mp: 133.0~135.0℃.

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Abstract

The invention relates to agomelatine benzenesulfonic acid compound of a formula I and a preparation method thereof; the agomelatine benzenesulfonic acid compound obtained by the invention is good in product stability, high in purity and is suitable for application demand when finished drug is prepared; preparation technology is also very simple; and a high-purity product can be obtained without special operation, wherein in the formula (I), R=CH3, H.

Description

technical field [0001] The invention relates to an agomelatine benzenesulfonic acid complex, a preparation method thereof, and a pharmaceutical component containing the agomelatine benzenesulfonic acid 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 antidepressant that can effectively treat depression, improve sleep parameters and maintain 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, CN2006...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/30C07C309/29C07C303/32C07C233/18C07C231/12A61K31/185A61K31/165A61P25/20A61P25/22A61P25/18A61P25/24A61P9/00A61P1/14
Inventor 王海平池骋池正明王进许关煜
Owner SHANGHAI RIGHTHAND PHARMTECH