CN1328260C - 新的β结晶形式的哌林多普利叔丁基胺盐、其制备方法和包含它的药物组合物 - Google Patents
新的β结晶形式的哌林多普利叔丁基胺盐、其制备方法和包含它的药物组合物 Download PDFInfo
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Abstract
本发明涉及β结晶形式的式(I)化合物，其特征在于其粉末X射线衍射图案。本发明可用于制备药物。
Description
本发明涉及新的β结晶形式的式(I)哌林多普利叔丁基胺盐：
其制备方法以及包含它的药物组合物。
哌林多普利及其可药用盐，更具体地说是其叔丁基胺盐，具有有价值的药理学性能。
它们的主要性能是抑制血管紧张素I转化酶(或激肽酶II)，后者一方面防止十肽血管紧张素I向八肽血管紧张素II(血管收缩药)转化且另一方面防止缓激肽(血管舒张药)降解成无活性肽。
这两个作用有助于哌林多普利在心血管疾病，更尤其是动脉高血压和心力衰竭中的有益效果。
哌林多普利、其制备及其在治疗剂中的用途已经描述于欧洲专利说明书EP0049658中。
鉴于该化合物的药物价值，最重要的是以优异纯度得到它。也重要的是能够通过可容易地转化成工业规模的方法，尤其以允许快速过滤和干燥的形式合成它。最后，该形式必须完全可再现、易于配制且足够稳定以允许其长期储存而对温度、光、湿度或氧含量没有特别要求。
专利说明书EP0308341描述了一种用于哌林多普利的工业合成方法。然而，该文献并没有说明以可再现地显示这些特征的形式得到哌林多普利的条件。
本申请的申请人现已发现哌林多普利的特定盐-叔丁基胺盐-可以良好限定的、完全可再现的结晶形式得到，其对配制尤其显示出有价值的特性。
更具体地说，本发明涉及β结晶形式的式(I)化合物，其特征在于其具有使用Siemens D5005衍射仪(铜对阴极)测量并以晶面间距d、布拉格角2θ、强度和相对强度(以最强射线的百分数表达)表达的以下粉末X射线衍射图：
| 2θ角(°) | 晶面间距d(_) | 强度 | 相对强度(％) |
| 5.169 | 17.08 | 523 | 16.5 |
| 8.379 | 10.54 | 1001 | 31.5 |
| 9.350 | 9.45 | 3175 | 100 |
| 14.746 | 6.00 | 236 | 7.4 |
| 15.411 | 5.74 | 753 | 23.7 |
| 15.931 | 5.56 | 279 | 8.8 |
| 16.711 | 5.30 | 113 | 3.6 |
| 18.161 | 4.88 | 122 | 3.8 |
| 20.564 | 4.32 | 1198 | 37.7 |
| 21.285 | 4.17 | 330 | 10.4 |
| 21.781 | 4.08 | 317 | 10 |
| 22.632 | 3.93 | 190 | 6 |
| 23.308 | 3.81 | 133 | 4.2 |
| 23.797 | 3.74 | 427 | 13.4 |
| 24.276 | 3.66 | 118 | 3.7 |
| 25.190 | 3.53 | 92 | 2.9 |
| 25.924 | 3.43 | 251 | 7.9 |
| 26.646 | 3.34 | 250 | 7.9 |
| 27.620 | 3.23 | 96 | 3 |
| 28.306 | 3.15 | 133 | 4.2 |
本发明还涉及一种制备β结晶形式的式(I)化合物的方法，该方法的特征在于：
-根据第一实施方案，在回流下加热哌林多普利叔丁基胺盐在二氯甲烷中的溶液，然后将溶液快速冷却至0℃并通过过滤收集所得固体；
-或根据第二实施方案，在回流下加热哌林多普利叔丁基胺盐在乙酸乙酯中的溶液，然后将溶液快速冷却至5℃并通过过滤收集所得固体。
·在根据本发明的结晶方法中，可以使用由任何方法得到的式(I)化合物。有利的是使用由专利说明书EP0308341中所述的制备方法得到的式(I)化合物。
·在本发明方法的第一实施方案中，式(I)化合物在二氯甲烷中的浓度优选为100-200g/l。
·在本发明方法的第二实施方案中，式(I)化合物在乙酸乙酯中的浓度优选为70-90g/l。
本发明还涉及药物组合物，其包含β结晶形式的式(I)化合物作为活性成分以及一种或多种合适的惰性、无毒赋形剂。在本发明的药物组合物中，可以更具体提及适于口服、胃肠外(静脉内或皮下)或经鼻给药的那些、片剂或糖锭剂、舌下片剂、明胶胶囊、锭剂、栓剂、霜剂、软膏、皮肤凝胶、可注射制剂、可饮用悬浮液等。
有用的剂量可以根据疾病的性质和严重程度、给药途径以及患者的年龄和体重而变化。它在1-500mg/天内变化，以一次或多次给药。
本发明的药物组合物也可包含利尿药如吲满胺。
下列实施例说明本发明但决不限制本发明。
在下列实验条件下测量粉末X射线衍射光谱：
-Siemens D5005衍射仪，闪烁探测器，
-铜对阴极(λ＝1.5405_)，电压40kV，强度40mA，
-安装θ-θ，
-测量角：5-30°，
-在各次测量之间的增量：0.02°，
-每步的测量时间：2秒，
-可变狭缝：v6，
-滤光器Kβ(Ni)，
-无内标，
-使用Siemens狭缝的调零程序，
-使用EVA软件(5.0版)处理实验数据。
实施例1：β结晶形式的哌林多普利叔丁基胺盐
将135g根据专利说明书EP0308341所述的方法得到的哌林多普利叔丁基胺盐溶于1100ml在回流下加热的二氯甲烷中。
然后将该溶液冷却至0℃并通过过滤收集所得固体。
粉末X射线衍射图：
β形式的哌林多普利叔丁基胺盐的粉末X射线衍射图案(衍射角)由在下表中分类的有效射线以及强度和相对强度(以最强射线的百分数表达)给出：
| 2θ角(°) | 晶面间距d(_) | 强度 | 相对强度(％) |
| 5.169 | 17.08 | 523 | 16.5 |
| 8.379 | 10.54 | 1001 | 31.5 |
| 9.350 | 9.45 | 3175 | 100 |
| 14.746 | 6.00 | 236 | 7.4 |
| 15.411 | 5.74 | 753 | 23.7 |
| 15.931 | 5.56 | 279 | 8.8 |
| 16.711 | 5.30 | 113 | 3.6 |
| 18.161 | 4.88 | 122 | 3.8 |
| 20.564 | 4.32 | 1198 | 37.7 |
| 21.285 | 4.17 | 330 | 10.4 |
| 21.781 | 4.08 | 317 | 10 |
| 22.632 | 3.93 | 190 | 6 |
| 23.308 | 3.81 | 133 | 4.2 |
| 23.797 | 3.74 | 427 | 13.4 |
| 24.276 | 3.66 | 118 | 3.7 |
| 25.190 | 3.53 | 92 | 2.9 |
| 25.924 | 3.43 | 251 | 7.9 |
| 26.646 | 3.34 | 250 | 7.9 |
| 27.620 | 3.23 | 96 | 3 |
| 28.306 | 3.15 | 133 | 4.2 |
实施例2：β结晶形式的哌林多普利叔丁基胺盐
将125g根据专利说明书EP0308341所述的方法得到的哌林多普利叔丁基胺盐溶于1.5升在回流下加热的乙酸乙酯中。
然后将该溶液快速冷却至5℃并通过过滤收集所得固体。
实施例3：药物组合物
制备1000片各含4mg活性成分的片剂的配方：
实施例1的化合物…………………………………………4g
羟丙基纤维素………………………………………………2g
小麦淀粉……………………………………………………10g
乳糖…………………………………………………………100g
硬脂酸镁……………………………………………………3g
滑石…………………………………………………………3g
Claims (8)
1.β结晶形式的式(I)化合物：
其特征在于其具有使用衍射仪(铜对阴极)测量并以晶面间距d、布拉格角2θ、强度和相对强度(以相对于最强射线的百分数表达)表达的以下粉末X射线衍射图：
2.制备根据权利要求1的β结晶形式的式(I)化合物的方法，其特征在于在回流下加热哌林多普利叔丁基胺盐在二氯甲烷中的溶液，然后将溶液冷却至0℃并通过过滤收集所得固体。
3.制备根据权利要求1的β结晶形式的式(I)化合物的方法，其特征在于在回流下加热哌林多普利叔丁基胺盐在乙酸乙酯中的溶液，然后将溶液快速冷却至5℃并通过过滤收集所得固体。
4.根据权利要求2的方法，其特征在于式(I)化合物在二氯甲烷中的浓度为100-200g/l。
5.根据权利要求3的方法，其特征在于式(I)化合物在乙酸乙酯中的浓度为70-90g/l。
6.药物组合物，包含根据权利要求1的化合物作为活性成分以及一种或多种可药用的惰性、无毒载体。
7.根据权利要求6的药物组合物，用于制造用作血管紧张素I转化酶的抑制剂的药物。
8.根据权利要求7的药物组合物，用于制造用于治疗心血管疾病的药物。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0008792A FR2811319B1 (fr) | 2000-07-06 | 2000-07-06 | Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR00/08792 | 2000-07-06 |
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| Publication Number | Publication Date |
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| CN1440388A CN1440388A (zh) | 2003-09-03 |
| CN1328260C true CN1328260C (zh) | 2007-07-25 |
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| FR (1) | FR2811319B1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2811320B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline alpha du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811318B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| GB2395195A (en) | 2002-11-18 | 2004-05-19 | Cipla Ltd | Preparation of perindopril from carboxy-protected precursor, & perindopril monohydrates for use as angiotensin converting enzyme (ACE) inhibitors |
| PL1636185T3 (pl) | 2003-06-24 | 2012-12-31 | Servier Lab | Nowe formy krystaliczne peryndoprylu erbuminy |
| WO2005037788A1 (en) | 2003-10-21 | 2005-04-28 | Lupin Ltd. | Novel method for preparation of crystalline perindopril erbumine |
| SI21703A (en) | 2004-01-14 | 2005-08-31 | Lek Farmacevtska Druzba Dd | Inclusion complexes of perindopril, procedure of their preparation, pharmaceutical compositions containing these complexes and their application in treatment of hypertensia |
| ES2603856T3 (es) * | 2004-03-29 | 2017-03-01 | Les Laboratoires Servier | Procedimiento para preparar una composición farmacéutica sólida |
| SI21800A (sl) | 2004-05-14 | 2005-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek sinteze perindoprila |
| SI21881A (sl) | 2004-10-15 | 2006-04-30 | Diagen, Smartno Pri Ljubljani, D.O.O. | Nove kristalne oblike perindopril erbumin hidratov, postopek za njihovo pripravo in farmacevtske oblike, ki vsebujejo te spojine |
| SG125976A1 (en) * | 2005-03-11 | 2006-10-30 | Servier Lab | New gama crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it |
| SG125975A1 (en) * | 2005-03-11 | 2006-10-30 | Servier Lab | New alpha crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it |
| JP2006290825A (ja) * | 2005-04-13 | 2006-10-26 | Shiono Chemical Co Ltd | アルファ型ペリンドプリルエルブミンの製造法 |
| WO2007017894A2 (en) * | 2005-05-05 | 2007-02-15 | Arch Pharmalabs Limited | PREPARATION OF NOVEL CRYSTALLINE η(ETA) FORM OF PERINDOPRIL ERBUMINE |
| WO2007020009A1 (en) * | 2005-08-12 | 2007-02-22 | Sandoz Ag | New crystalline form of perindopril erbumine |
| MX2008002064A (es) * | 2005-08-12 | 2008-04-17 | Lek Pharmaceuticals | Un proceso para la preparacion de perindopril-erbumina. |
| EP1815857A1 (en) | 2006-02-02 | 2007-08-08 | LEK Pharmaceuticals D.D. | A pharmaceutical composition comprising perindopril |
| WO2007092758A2 (en) * | 2006-02-03 | 2007-08-16 | Dr. Reddy's Laboratories Ltd. | Crystalline forms of perindopril erbumine |
| FR2897865B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline beta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2897866B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| WO2008050185A2 (en) * | 2006-10-26 | 2008-05-02 | Glenmark Pharmaceuticals Limited | Novel polymorphs of perindopril erbumine |
| WO2008120241A2 (en) * | 2007-03-29 | 2008-10-09 | Ipca Laboratories Limited | Novel alcohol solvates of perindopril erbumine |
| SI22543A (sl) | 2007-06-27 | 2008-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove soli perindoprila |
| DK2318365T3 (en) * | 2008-06-24 | 2015-11-23 | Mylan Lab Ltd | NOVEL polymorphic forms of perindopril (L) -arginine AND PROCESS FOR PREPARATION THEREOF |
| SI23149A (sl) | 2009-09-21 | 2011-03-31 | Silverstone Pharma | Nove benzatinske soli ACE inhibitorjev, postopek za njihovo pripravo in njihova uporaba za zdravljenje kardiovaskularnih bolezni |
| PT105315B (pt) | 2010-09-29 | 2013-01-16 | Inst Superior Tecnico | Uma nova forma cristalina hidratada de erbumina de perindopril, métodos para a sua preparação e sua utilização em preparações farmacêuticas |
| CN106432042A (zh) * | 2015-08-13 | 2017-02-22 | 南京华威医药科技开发有限公司 | 尼达尼布乙磺酸水合物的药物新晶型 |
| EP3842035A1 (en) | 2019-12-23 | 2021-06-30 | KRKA, d.d., Novo mesto | Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308341A1 (fr) * | 1987-09-17 | 1989-03-22 | Adir Et Compagnie | Procédé de synthèse industrielle du périndopril et de ses principaux intermédiaires de synthèse |
| FR2771010A1 (fr) * | 1997-11-19 | 1999-05-21 | Adir | Utilisation d'une combinaison d'un inhibiteur de l'enzyme de conversion de l'angiotensine et d'un diuretique pour le traitement des desordres microcirculatoires |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2811320B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline alpha du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811318B1 (fr) | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308341A1 (fr) * | 1987-09-17 | 1989-03-22 | Adir Et Compagnie | Procédé de synthèse industrielle du périndopril et de ses principaux intermédiaires de synthèse |
| US4914214A (en) * | 1987-09-17 | 1990-04-03 | Adir Et Cie | Process for the industrial synthesis of perindopril |
| FR2771010A1 (fr) * | 1997-11-19 | 1999-05-21 | Adir | Utilisation d'une combinaison d'un inhibiteur de l'enzyme de conversion de l'angiotensine et d'un diuretique pour le traitement des desordres microcirculatoires |
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