CN100445264C - 阿戈美拉汀的新晶形ⅳ、它的制备方法和包含它的药物组合物 - Google Patents
阿戈美拉汀的新晶形ⅳ、它的制备方法和包含它的药物组合物 Download PDFInfo
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Abstract
式(I)化合物的晶形IV以及含有它的药物,该晶形以其粉末X射线衍射图表征。
Description
技术领域
本发明涉及阿戈美拉汀或式(I)的N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺的新晶形IV:
它的制备方法以及包含它的药物组合物。
背景技术
阿戈美拉汀,或N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺,具有有价值的药理性质。
它确实具有双重的特征,一方面,它是褪黑激素能系统受体的激动剂,另一方面,它是5-HT2C受体的拮抗剂。这些性质使得它在中枢神经系统中具有活性,更特别是在严重抑郁症(severe depression)、季节性情感障碍、睡眠紊乱、心血管疾病、消化系统疾病、由时差导致的失眠和疲劳、食欲紊乱和肥胖症的治疗中有活性。
阿戈美拉汀、它的制备和它的治疗用途在欧洲专利说明书EP 0447285中已有描述。
鉴于该化合物的药学价值,获得纯度优良、具有很确定晶形且重现性极好的该化合物是重要的,其结果是在制剂方面呈现出有价值的特性,并且足够稳定以使得它可长时间储存而没有对温度、光、湿度或氧气水平的特定要求。
专利说明书EP 0447285描述了阿戈美拉汀从7-甲氧基-1-四氢萘酮起始的八步制备。但是,该文件中没有具体说明以可重现方式获得呈现这些特性的阿戈美拉汀的条件。
发明内容
本申请人现已开发了新的合成方法,该方法可以以很确定的、重现性极好的晶形获得阿戈美拉汀,所述晶形在制剂方面尤其显示出有价值的特性。
更具体而言,本发明涉及式(I)化合物的晶形IV,其以下列的粉末X射线衍射图表征,使用西门子D5005衍射计(铜对阴极)进行测定,以晶面间距d、布拉格2θ角、强度和相对强度(以最强射线的百分数表示)表示:
本发明还涉及式(I)化合物的晶形IV的制备方法,该方法的特征在于,于110℃加热阿戈美拉汀直至完全熔化,然后在50和70℃之间迅速冷却,并在70℃维持约5小时直至结晶。
获得这种晶形的优点是其允许制备具有一致且可重现组成的药物制剂,当制剂用于口服施用时这是特别有益的。
对如此获得的晶形IV的药理研究已经证实它在中枢神经系统和微循环中具有重要活性,这使得阿戈美拉汀的晶形IV被确立可用于治疗下列病症:紧张、睡眠紊乱、焦虑、严重抑郁症、季节性情感障碍、心血管疾病、消化系统疾病、由时差导致的失眠和疲劳、精神分裂症、恐慌发作、忧郁症、食欲紊乱、肥胖症、失眠、疼痛、精神紊乱、癫痫、糖尿病、帕金森病、老年性痴呆、与正常或病理性老化有关的各种紊乱、偏头痛、记忆丧失、阿尔茨海默病以及脑循环紊乱。在另一个活性领域,表明阿戈美拉汀的晶形IV可用于治疗性功能障碍,具有排卵抑制和免疫调节的性质,并且可用于治疗癌症。
阿戈美拉汀的晶形IV优选用于治疗严重抑郁症、季节性情感障碍、睡眠紊乱、心血管疾病、由时差导致的失眠和疲劳、食欲紊乱和肥胖症。
本发明还涉及包含作为活性成分的阿戈美拉汀的晶形IV以及一种或多种适宜的惰性无毒赋形剂的药物组合物。在本发明的药物组合物中,可以提及的更特别是适于口服、胃肠道外(静脉内或皮下)或经鼻施用的那些,例如片剂或糖衣丸、颗粒剂、舌下片、明胶胶囊、锭剂、栓剂、乳膏剂、软膏剂、皮肤凝胶、可注射制剂、可饮用混悬剂和可崩解糊剂。
根据紊乱的性质和严重性、施用途径以及患者的年龄及体重调节有用剂量。剂量在每天0.1mg至1g之间变化,一次或多次施用。
具体实施方式
下列的实施例说明本发明,但不以任何方式限制本发明。
实施例1:N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺的晶形IV
于110℃加热100g N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺直至完全熔化,然后在50和70℃之间迅速冷却,并在70℃维持5小时直至结晶。所得晶形IV以下列的粉末X射线衍射图表征,使用西门子D5005衍射计(铜对阴极)进行测定,以晶面间距d、布拉格2θ角、强度和相对强度(以最强射线的百分数表示)表示:
实施例2:药物组合物
制备1000片片剂的处方,每片含有25mg剂量:
实施例1的化合物..............................................25g
乳糖一水合物.................................................62g
硬脂酸镁.....................................................1.3g
玉米淀粉.....................................................26g
麦芽糖糊精合剂...............................................9g
无水胶体二氧化硅.............................................0.3g
A型淀粉羟乙酸钠..............................................4g
硬脂酸.......................................................2.6g
实施例3:药物组合物
制备1000片片剂的处方,每片含有25mg剂量:
实施例1的化合物..............................................25g
乳糖一水合物.................................................62g
硬脂酸镁.....................................................1.3g
聚维酮............................................................9g
无水胶体二氧化硅..................................................0.3g
羧甲基纤维素钠....................................................30g
硬脂酸............................................................2.6g
Claims (5)
2.权利要求1的式(I)化合物的晶形IV的制备方法,其特征在于,在110℃加热阿戈美拉汀直至完全熔化,然后在50和70℃之间迅速冷却,并在70℃维持约5小时直至结晶。
3.药物组合物,包含作为活性成分的权利要求1的阿戈美拉汀的晶形IV以及一种或多种可药用的惰性无毒载体。
4.权利要求1的式(I)化合物的晶形IV在制造治疗褪黑激素能紊乱的药物中的用途。
5.权利要求1的式(I)化合物的晶形IV在制造治疗下列病症的药物中的用途:睡眠紊乱、紧张、焦虑、季节性情感障碍或严重抑郁症、心血管疾病、消化系统疾病、由时差导致的失眠和疲劳、精神分裂症、恐慌发作、忧郁症、食欲紊乱、肥胖症、失眠、精神紊乱、癫痫、糖尿病、帕金森病、老年性痴呆、与正常或病理性老化有关的各种紊乱、偏头痛、记忆丧失、阿尔茨海默病、脑循环紊乱,性功能障碍,用作排卵抑制剂和免疫调节剂,以及癌症。
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Application Number | Priority Date | Filing Date | Title |
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FR0508277A FR2889522B1 (fr) | 2005-08-03 | 2005-08-03 | Nouvelle forme cristalline iv de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
FR0508277 | 2005-08-03 |
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CN1907957A CN1907957A (zh) | 2007-02-07 |
CN100445264C true CN100445264C (zh) | 2008-12-24 |
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EP (2) | EP1752444A1 (zh) |
JP (1) | JP4580371B2 (zh) |
CN (1) | CN100445264C (zh) |
AR (1) | AR057714A1 (zh) |
AU (1) | AU2006203340B2 (zh) |
BR (1) | BRPI0603043A (zh) |
CA (1) | CA2555119A1 (zh) |
CO (1) | CO5780132A1 (zh) |
EA (1) | EA010867B1 (zh) |
FR (1) | FR2889522B1 (zh) |
GE (1) | GEP20094577B (zh) |
GT (1) | GT200600345A (zh) |
HK (1) | HK1098129A1 (zh) |
MA (1) | MA28450B1 (zh) |
MX (1) | MXPA06008693A (zh) |
MY (1) | MY141306A (zh) |
NO (1) | NO20063518L (zh) |
NZ (1) | NZ548863A (zh) |
PE (1) | PE20070242A1 (zh) |
SA (1) | SA06270254B1 (zh) |
SG (1) | SG130111A1 (zh) |
TW (1) | TWI327564B (zh) |
UA (1) | UA83718C2 (zh) |
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Cited By (1)
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WO2010102554A1 (zh) * | 2009-03-10 | 2010-09-16 | 上海医药工业研究院 | 阿戈美拉汀的新晶型ⅵ及其制备方法和应用 |
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FR2923482B1 (fr) * | 2007-11-09 | 2010-01-29 | Servier Lab | Nouvelle forme cristalline vi de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
FR2934856B1 (fr) * | 2008-08-05 | 2010-08-13 | Servier Lab | Nouveau procede d'obtention de la forme cristalline v de l'agomelatine |
WO2011006387A1 (zh) * | 2009-07-11 | 2011-01-20 | 浙江华海药业股份有限公司 | 阿戈美拉汀的制备方法、阿戈美拉汀晶形及其制备方法 |
CN102001959B (zh) * | 2009-09-01 | 2014-07-02 | 北京本草天源药物研究院 | 一种药物晶体及其制备方法和用途 |
CN102050755B (zh) * | 2009-10-29 | 2014-11-05 | 重庆医药工业研究院有限责任公司 | 阿戈美拉汀的晶型及其制备方法 |
CN101781226B (zh) | 2009-12-23 | 2012-03-28 | 天津泰普药品科技发展有限公司 | 阿戈美拉汀及其药物组合物 |
CN101870662B (zh) * | 2010-05-21 | 2013-03-20 | 中山大学 | 结晶型阿戈美拉汀溶剂化物及其制备方法 |
CL2011001405A1 (es) | 2010-06-10 | 2012-03-30 | Gador S A Conicet | Procedimiento para la preparacion de n-[2-(7-metoxi-1-naftil)etil]acetamida, agometalina. |
CN102690210A (zh) | 2011-03-23 | 2012-09-26 | 上海医药工业研究院 | 阿戈美拉汀的新晶型ⅶ、其制备方法、应用和包含其的药物组合物 |
CN102690209A (zh) * | 2011-03-23 | 2012-09-26 | 上海医药工业研究院 | 阿戈美拉汀的混晶(形式-ⅷ)、其制备方法、应用和包含其的药物组合物 |
FR2978916B1 (fr) | 2011-08-10 | 2013-07-26 | Servier Lab | Composition pharmaceutique solide pour administration buccale d'agomelatine |
CN102503886B (zh) * | 2011-10-11 | 2013-09-11 | 中山大学 | 阿戈美拉汀-异烟碱共晶及其组合物和制备方法 |
ES2634243T3 (es) | 2011-11-30 | 2017-09-27 | Ratiopharm Gmbh | Complejo de agomelatina-urea y formas cristalinas del mismo |
CZ2012108A3 (en) | 2012-02-15 | 2013-02-27 | Zentiva Ks | A method for the manufacture of a polymorphously stable pharmaceutical composition containing agomelatine |
CN102643208B (zh) * | 2012-04-14 | 2013-11-06 | 中山大学 | 一种阿戈美拉汀ⅰ晶型的制备方法 |
WO2014096373A1 (en) | 2012-12-21 | 2014-06-26 | Laboratorios Lesvi, S. L. | Process for prepararing n-(2-(7-methoxy-1-naphthalenyl)ethyl) acetamide and solid forms thereof |
FR3001894A1 (fr) | 2013-02-08 | 2014-08-15 | Servier Lab | Composition pharmaceutique solide pour administration buccale d'agomelatine |
PT2810656T (pt) | 2013-06-06 | 2017-11-13 | Zentiva As | Formulações de agomelatina compreendendo agomelatina na forma de cocristais |
EP2810647A1 (en) | 2013-06-06 | 2014-12-10 | Zentiva, a.s. | Pharmaceutical formulations comprising agomelatine in the form of agomelatine co-crystal with an organic acid |
CZ2013621A3 (cs) | 2013-08-13 | 2015-02-25 | Zentiva, K.S. | Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci |
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EP3466413A1 (en) | 2017-10-09 | 2019-04-10 | KRKA, d.d., Novo mesto | Pharmaceutical composition containing agomelatine and process for the preparation thereof |
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WO2010102554A1 (zh) * | 2009-03-10 | 2010-09-16 | 上海医药工业研究院 | 阿戈美拉汀的新晶型ⅵ及其制备方法和应用 |
AU2010223720B2 (en) * | 2009-03-10 | 2012-05-03 | Les Laboratoires Servier | New crystalline form VI of Agomelatine, preparation method and application thereof |
US8614251B2 (en) | 2009-03-10 | 2013-12-24 | Les Laboratories Servier | Crystalline form VI of agomelatine, preparation method and application thereof |
EA019127B1 (ru) * | 2009-03-10 | 2014-01-30 | Ле Лаборатуар Сервье | Новая кристаллическая форма vi агомелатина, ее получение и применение |
Also Published As
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HK1098129A1 (en) | 2007-07-13 |
EA200601271A1 (ru) | 2007-02-27 |
EP2008994A1 (fr) | 2008-12-31 |
MY141306A (en) | 2010-04-16 |
MA28450B1 (fr) | 2007-03-01 |
NO20063518L (no) | 2007-02-05 |
CO5780132A1 (es) | 2007-07-31 |
WO2007015002A2 (fr) | 2007-02-08 |
WO2007015002A3 (fr) | 2007-04-12 |
TWI327564B (en) | 2010-07-21 |
GEP20094577B (en) | 2009-01-12 |
CN1907957A (zh) | 2007-02-07 |
SG130111A1 (en) | 2007-03-20 |
MXPA06008693A (es) | 2007-02-02 |
AU2006203340B2 (en) | 2012-07-19 |
FR2889522A1 (fr) | 2007-02-09 |
EP1752444A1 (fr) | 2007-02-14 |
BRPI0603043A (pt) | 2007-03-20 |
NZ548863A (en) | 2008-03-28 |
TW200736198A (en) | 2007-10-01 |
CA2555119A1 (fr) | 2007-02-03 |
ZA200606455B (en) | 2007-12-27 |
FR2889522B1 (fr) | 2007-12-28 |
UA83718C2 (ru) | 2008-08-11 |
GT200600345A (es) | 2007-03-28 |
JP4580371B2 (ja) | 2010-11-10 |
SA06270254B1 (ar) | 2010-08-02 |
JP2007051141A (ja) | 2007-03-01 |
AU2006203340A1 (en) | 2007-02-22 |
AR057714A1 (es) | 2007-12-12 |
EA010867B1 (ru) | 2008-12-30 |
PE20070242A1 (es) | 2007-05-06 |
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