CN102050756A - New crystal form of agomelatine and preparation method thereof - Google Patents
New crystal form of agomelatine and preparation method thereof Download PDFInfo
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- CN102050756A CN102050756A CN2009103094298A CN200910309429A CN102050756A CN 102050756 A CN102050756 A CN 102050756A CN 2009103094298 A CN2009103094298 A CN 2009103094298A CN 200910309429 A CN200910309429 A CN 200910309429A CN 102050756 A CN102050756 A CN 102050756A
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Abstract
The invention discloses a new crystal form of agomelatine and a preparation method thereof. The new crystal form is characterized in that: an X-ray powder diffraction pattern of a crystal has characteristic absorption peaks when angles of reflection 2theta are about 11.7 degrees, 17.4 degrees, 18.2 degrees, 19.4 degrees, 20.4 degrees, 21.6 degrees and 25.2 degrees.
Description
Technical field
The present invention relates to Agomelatine new crystal and preparation method thereof.
Background technology
Agomelatine (Agomelatine), chemical name: N-[2-(7-methoxyl group-1-naphthyl) ethyl] ethanamide, chemical structural formula is as follows:
Agomelatine has the pharmacological property of two aspects, and on the one hand, it is the agonist of melatonin energy system acceptor, and on the other hand, it is a kind of 5-HT
2CThe antagonist of acceptor.Therefore, Agomelatine possesses activity in central nervous system, and especially has activity in the treatment of insomnia that severe depression, seasonal affective disorder, somnopathy, cardiovascular disorder, digestive system, jet lag cause and fatigue, appetite disorder and obesity.
Agomelatine, its preparation and therepic use thereof have been described in European patent specification EP0447285.Servier Lab has described different crystal habit II, III, IV, V, the VI of Agomelatine respectively in patent CN200510071611.6, CN200610108396.7, CN200610108394.8, CN200610108395.2, CN200810174918.2, and by X-ray powder diffraction it is characterized.
The inventor has found the new crystal that another is stable, called after VII type in further investigation crystalline process.
Summary of the invention
Purpose of the present invention provides a kind of new crystal of Agomelatine, and this crystal formation is named the type into VII, and its X-ray powder diffraction pattern is about 11.7,17.4 at reflection angle 2 θ, and 18.2,19.4,20.4,21.6, there is charateristic avsorption band at 25.2 places.
Among the present invention, the mensuration of 2 θ values is used CuK α light source, is precision? .2 °, therefore, should " pact " in above-mentioned " X-ray powder diffraction pattern charateristic avsorption band reflection angle 2 θ are about " be defined as 2 θ? .2 °, represent above-mentioned 2 θ values of getting to allow certain reasonably limit of error, is its limit of error? .2 °.
Another object of the present invention is the preparation method who discloses Agomelatine new crystal VII.
Agomelatine new crystal VII of the present invention can be by conventional method preparation.For example, by small amount of ethanol, methyl alcohol, Virahol or its mixed solvent heating for dissolving, drip while hot and add water to muddiness, cooling crystallization; By small amount of acetone, butanone or its mixed solvent heating for dissolving, drip while hot and add water to muddiness, cooling crystallization; By amount of ethyl acetate, methyl acetate, ethyl formate, isopropyl acetate or its mixed solvent heating for dissolving, drip sherwood oil or normal hexane while hot to muddy, cooling crystallization.
Embodiment
Can further describe the present invention by the following examples, yet invention of the present invention is not limited to the following examples, the scope that these embodiment do not limit the present invention in any way.Some change that those skilled in the art has done within the scope of the claims and adjust also should be thought and belongs to scope of the present invention.
The preparation of embodiment 1 crystal form V II
Agomelatine 1g is with 10ml dehydrated alcohol heating for dissolving, drips while hot to add water to muddiness, cooling crystallization, suction filtration, 50 ℃ of vacuum-dryings.
The preparation of embodiment 2 crystal form V II
Agomelatine 1g is with 10ml methyl alcohol heating for dissolving, drips while hot to add water to muddiness, cooling crystallization, suction filtration, 50 ℃ of vacuum-dryings.
The preparation of embodiment 3 crystal form V II
Agomelatine 1g drips normal hexane to muddy, cooling crystallization, suction filtration, 50 ℃ of vacuum-dryings while hot with 10ml ethyl acetate heating for dissolving.
The preparation of embodiment 4 crystal form V II
Agomelatine 1g drips sherwood oil to muddy, cooling crystallization, suction filtration, 50 ℃ of vacuum-dryings while hot with 10ml ethyl acetate heating for dissolving.
The preparation of embodiment 5 crystal form V II
Agomelatine 1g is with 10ml acetone heating for dissolving, drips while hot to add water to muddiness, cooling crystallization, suction filtration, 50 ℃ of vacuum-dryings.
The mensuration of embodiment 6 Agomelatine new crystal physical propertys
Place on the powder diffractometer by the Agomelatine powder of X-ray diffraction method new crystal, with 8 degree/minute scanning speed scan between the 2 θ angles at 2.6～40 degree, use Cu-Ka 40Kv～100mAX x radiation x.
The X-ray powder diffraction of accompanying drawing 1 crystal form V II.
Claims (4)
1. the new crystal VII of an Agomelatine is characterized in that this crystalline X-ray powder diffraction pattern is about 11.7,17.4 at reflection angle 2 θ, 18.2,19.4,20.4,21.6, and there is charateristic avsorption band at 25.2 places.
2. the described crystal form V II of claim 1, its preparation method is: by small amount of ethanol, methyl alcohol, Virahol or its mixed solvent heating for dissolving, drip while hot and add water to muddiness, cooling crystallization.
3. the described crystal form V II of claim 1, its preparation method is: by small amount of acetone, butanone or its mixed solvent heating for dissolving, drip while hot and add water to muddiness, cooling crystallization.
4. the described crystal form V II of claim 1, its preparation method is: by amount of ethyl acetate, methyl acetate, ethyl formate, isopropyl acetate or its mixed solvent heating for dissolving, drip sherwood oil or normal hexane while hot to muddy, cooling crystallization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2009103094298A CN102050756A (en) | 2009-11-09 | 2009-11-09 | New crystal form of agomelatine and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2009103094298A CN102050756A (en) | 2009-11-09 | 2009-11-09 | New crystal form of agomelatine and preparation method thereof |
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| CN102050756A true CN102050756A (en) | 2011-05-11 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102557979A (en) * | 2010-12-16 | 2012-07-11 | 北大方正集团有限公司 | Agomelatine crystal form, as well as preparation method, application and medicinal composition thereof |
| EP2556824A1 (en) | 2011-08-10 | 2013-02-13 | Les Laboratoires Servier | Solid pharmaceutical composition for buccal administration of agomelatine |
| CN103130673A (en) * | 2011-11-28 | 2013-06-05 | 重庆医药工业研究院有限责任公司 | Preparation method of agomelatine crystal type I |
| WO2014122405A1 (en) | 2013-02-08 | 2014-08-14 | Les Laboratoires Servier | Solid pharmaceutical composition for oral delivery of agomelatine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1680284A (en) * | 2004-02-13 | 2005-10-12 | 瑟维尔实验室 | New process for the synthesis and new crystalline form of agomelatine and pharmaceutical compositions containing it |
| CN101585779A (en) * | 2009-03-10 | 2009-11-25 | 上海医药工业研究院 | New crystal form of Agomelatine, preparation method and use thereof |
| CN101955440A (en) * | 2009-07-17 | 2011-01-26 | 北京德众万全药物技术开发有限公司 | Novel crystal form of agomelatine and preparation method thereof |
| CN102050755A (en) * | 2009-10-29 | 2011-05-11 | 重庆医药工业研究院有限责任公司 | Novel agomelatine crystal forms and preparation methods of agomelatine crystal forms |
-
2009
- 2009-11-09 CN CN2009103094298A patent/CN102050756A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1680284A (en) * | 2004-02-13 | 2005-10-12 | 瑟维尔实验室 | New process for the synthesis and new crystalline form of agomelatine and pharmaceutical compositions containing it |
| CN101585779A (en) * | 2009-03-10 | 2009-11-25 | 上海医药工业研究院 | New crystal form of Agomelatine, preparation method and use thereof |
| CN101955440A (en) * | 2009-07-17 | 2011-01-26 | 北京德众万全药物技术开发有限公司 | Novel crystal form of agomelatine and preparation method thereof |
| CN102050755A (en) * | 2009-10-29 | 2011-05-11 | 重庆医药工业研究院有限责任公司 | Novel agomelatine crystal forms and preparation methods of agomelatine crystal forms |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102557979A (en) * | 2010-12-16 | 2012-07-11 | 北大方正集团有限公司 | Agomelatine crystal form, as well as preparation method, application and medicinal composition thereof |
| CN102557979B (en) * | 2010-12-16 | 2014-11-26 | 北大方正集团有限公司 | Agomelatine crystal form, as well as preparation method, application and medicinal composition thereof |
| EP2556824A1 (en) | 2011-08-10 | 2013-02-13 | Les Laboratoires Servier | Solid pharmaceutical composition for buccal administration of agomelatine |
| WO2013021139A1 (en) | 2011-08-10 | 2013-02-14 | Les Laboratoires Servier | Solid pharmaceutical composition for orally delivering agomelatine |
| CN103130673A (en) * | 2011-11-28 | 2013-06-05 | 重庆医药工业研究院有限责任公司 | Preparation method of agomelatine crystal type I |
| CN103130673B (en) * | 2011-11-28 | 2017-05-03 | 重庆医药工业研究院有限责任公司 | Preparation method of agomelatine crystal type I |
| WO2014122405A1 (en) | 2013-02-08 | 2014-08-14 | Les Laboratoires Servier | Solid pharmaceutical composition for oral delivery of agomelatine |
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Address after: 100070 Beijing City, Fengtai District Fengtai Science Park No. 4 Fung Fu Road Federation building A block 16 layer 16A02 Applicant after: Beijing Lelijian Biotechnology Co., Ltd. Address before: 100070 Beijing City, Fengtai District Fengtai Science Park No. 4 Fung Fu Road Federation building A block 16 layer 16A02 Applicant before: Beijing Lilesheng Pharmaceutical Technology Co., Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: BEIJING LILESHENG PHARMACEUTICAL TECHNOLOGY CO., LTD. TO: BEIJING LELIJIAN BIOTECHNOLOGY CO., LTD. |
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Application publication date: 20110511 |