TWI389873B - 阿戈美拉汀（ａｇｏｍｅｌａｔｉｎｅ）之新晶形iii，其製備方法及包含其之醫藥組合物 - Google Patents
阿戈美拉汀（ａｇｏｍｅｌａｔｉｎｅ）之新晶形iii，其製備方法及包含其之醫藥組合物 Download PDFInfo
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Description
本發明係關於一種式(I)之阿戈美拉汀或N－[2－(7－甲氧基－1－萘基)乙基]乙醯胺之新晶形III：
其製備方法及包含其之醫藥組合物。
阿戈美拉汀或N－[2－(7－甲氧基－1－萘基)乙基]乙醯胺具有重要之藥理性質。
其確實具有雙重特徵，一方面為褪黑激素能系統受體之激動劑，及另一方面為5－HT2 C
受體之拮抗劑。此等性質在中樞神經系統中及尤其在嚴重抑鬱症、季節性情感障礙、睡眠障礙、心血管病變、消化系統病變、失眠症及由時差產生之疲勞、食慾障礙及肥胖之治療中賦與活性。
阿戈美拉汀，其製備及其治療用途在歐洲專利說明書EP 0 447 285中已有所描述。
鑒於此化合物之醫藥價值，能夠獲得具有極高純度、具有適當界定、較佳可再現之晶形之該化合物是很重要的，其因此用調配物來展示重要特徵且充分穩定以允許其長期存儲而對溫度、光、濕度或氧含量無特別要求。
專利說明書EP 0 447 285從7－甲氧基－1－四氫萘酮開始，以八個步驟描述阿戈美拉汀之製備。然而，彼文獻並未以可再現方式規定用於獲得以展示彼等特徵之形式之阿戈美拉汀的條件。
申請者現已開發一種新的合成方法，其允許獲得以適當界定、較佳可再現、尤其對於調配物展現重要特徵之晶形之阿戈美拉汀。
更特定言之，本發明係關於式(I)之化合物之晶形III，該化合物之晶形III由以下粉末X射線繞射圖表表徵、用Siemens D5005繞射計(銅對陰極)量測及以內部平面距離d、布拉格(Bragg's)角度2θ、強度及相對強度(表示成最大強度射線之百分比)來表示：
本發明亦係關於一種製備式(I)之化合物之晶形III的方法，其方法之特徵在於將阿戈美拉汀於110℃加熱直到完全熔化，及接著慢慢冷卻直至結晶。
獲得彼晶形之優勢在於其允許製備具有一致及可再現之組合物之醫藥調配物，其特別有利於當該等調配物用於口服投藥時。
對如此獲得之形態III之藥理研究已表明其關於中樞神經系統及關於微循環具有實質活性，使得其得以證實阿戈美拉汀之晶形III在治療精神緊張、睡眠障礙、焦慮症、嚴重抑鬱症、季節性情感障礙、心血管病變、消化系統病變、失眠症及由於時差所引起之疲勞、精神分裂症、恐慌發作、憂鬱症、食慾障礙、肥胖、失眠症、疼痛、精神性失常、癲癇症、糖尿病、帕金森氏症、老年癡呆症、與正常或病理性衰老相關之各種失調症、偏頭痛、記憶力喪失、阿茲海默氏病症及大腦循環失調症中有效。在另一活性方面中，表明阿戈美拉汀之晶形III可用於治療性功能障礙、其具有抑制排卵及免疫調節之性質、及其適合用於治療癌症。阿戈美拉汀之晶形III較佳用於治療嚴重抑鬱症、季節性情感障礙、睡眠障礙、心血管病變、失眠症及由時差引起之疲勞、食慾障礙及肥胖。
本發明亦係關於醫藥組合物，其包括作為活性成份之阿戈美拉汀之晶形III連同一或多種合適的惰性、無毒的賦形劑。根據本發明之醫藥組合物中，提到尤其適於口服、非經腸(靜脈內或皮下)或鼻腔投藥之醫藥組合物、錠劑或糖衣藥丸、顆粒、舌下錠、明膠膠囊、口含劑、栓劑、乳劑、軟膏劑、皮凝膠、注射製劑、飲用懸浮液及可崩解糊劑。
可根據失調症之性質及嚴重性、投藥路徑及患者之年齡及體重調整有效劑量。在一或多次投藥過程中，劑量以每天自0.1 mg至1 g變化。
以下實例說明但不以任何方式限制本發明。
將100 gN－[2－(7－甲氧基－1－萘基)乙基]乙醯胺於通風恆溫箱內，在110℃加熱直到完全熔化，及接著慢慢冷卻直至結晶。所獲得之晶形III由以下粉末X射線繞射圖表表徵、用Siemens D5005繞射計(銅對陰極)量測及以內部平面距離d、Bragg's角度2θ、強度及相對強度(表示成最大強度射線之百分比)來表示。
製備1000粒錠劑之調配物，每粒錠劑含有之劑量為25 mg。
實例1之化合物.........25 g乳糖單水合物.........62 g硬脂酸鎂.........1.3 g玉米澱粉.........26 g麥芽糊精.........9 g無水膠狀二氧化矽.........0.3 gA型羥基乙酸澱粉鈉.........4 g硬脂酸.........2.6 g
製備1000粒錠劑之調配物，每粒錠劑含有之劑量為25 mg。
實例1之化合物.........25 g乳糖單水合物.........62 g硬脂酸鎂.........1.3 g聚乙烯吡咯酮.........9 g無水膠狀二氧化矽.........0.3 g纖維素羥乙酸鈉.........30 g硬脂酸.........2.6 g
Claims (5)
- 一種式(I)之阿戈美拉汀之晶形III，
- 一種製備如請求項1之式(I)之化合物之晶形III的方法，其特徵在於將阿戈美拉汀於110℃加熱直到完全熔化，且接著慢慢冷卻直至結晶。
- 一種醫藥組合物，其包含作為活性成份之如請求項1之阿戈美拉汀之晶形III，與一或多種醫藥上可接受之惰性、無毒載劑組合。
- 如請求項3之醫藥組合物，其用於製造治療褪黑素能失調症之藥劑。
- 如請求項3之醫藥組合物，其用於製造治療睡眠障礙、精神緊張、焦慮症、季節性情感障礙或嚴重抑鬱症、心血管病變、消化系統病變、失眠症及由於時差所引起的疲勞、精神分裂症、恐慌發作、憂鬱症、食慾障礙、肥胖、失眠症、精神性失常、癲癇症、糖尿病、帕金森氏症、老年癡呆症、與正常或病理性衰老相關之各種失調症、偏頭痛、記憶力喪失、阿茲海默氏病症、大腦循環失調症，及治療性功能障礙、作為排卵抑制劑、免疫調節劑及癌症之藥劑。
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| FR0508276A FR2889521B1 (fr) | 2005-08-03 | 2005-08-03 | Nouvelle forme cristalline iii de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2934856B1 (fr) * | 2008-08-05 | 2010-08-13 | Servier Lab | Nouveau procede d'obtention de la forme cristalline v de l'agomelatine |
| CN101585779B (zh) * | 2009-03-10 | 2014-04-02 | 上海医药工业研究院 | 阿戈美拉汀的晶型vi及其制备方法和应用 |
| 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 |
| CN101709036B (zh) * | 2009-12-17 | 2012-07-04 | 天津药物研究院 | 阿戈美拉汀中间体2-(7-甲氧基-1-萘基)乙胺的制备 |
| 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 |
| CN101774937B (zh) * | 2010-02-05 | 2014-01-08 | 天津市汉康医药生物技术有限公司 | N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺及其组合物 |
| WO2011154140A2 (en) | 2010-06-10 | 2011-12-15 | Gador S.A. | New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide and new crystalline form |
| CZ303787B6 (cs) * | 2011-01-21 | 2013-05-02 | Zentiva, K.S. | Metastabilní krystalové formy agomelatinu a jejich farmaceutické kompozice |
| 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 |
| EP2771312B1 (en) | 2011-11-30 | 2017-05-31 | ratiopharm GmbH | Agomelatine-urea complex and crystalline forms thereof |
| CZ2012108A3 (en) | 2012-02-15 | 2013-02-27 | Zentiva Ks | A method for the manufacture of a polymorphously stable pharmaceutical composition containing agomelatine |
| EP2934502A1 (en) | 2012-12-21 | 2015-10-28 | 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 |
| 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 |
| ES2645223T3 (es) | 2013-06-06 | 2017-12-04 | Zentiva, K.S. | Formulaciones de agomelatina que comprenden agomelatina en forma de co-cristales |
| CZ2013621A3 (cs) | 2013-08-13 | 2015-02-25 | Zentiva, K.S. | Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci |
| WO2015124496A1 (en) | 2014-02-19 | 2015-08-27 | Synthon B.V. | Pharmaceutical composition comprising amorphous agomelatine |
| PL3075724T3 (pl) | 2015-03-31 | 2023-12-27 | F.I.S.- Fabbrica Italiana Sintetici S.P.A. | Stała postać agomelatyny |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2866336B1 (fr) * | 2004-02-13 | 2006-03-24 | Servier Lab | Nouveau procede de synthese du (7-methoxy-3,4-dihydro-1-naphtalenyl) acetonitrile et application a la synthese de l'agomelatine |
| FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
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