CN1440386A - 新的γ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γ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 PDF

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CN1440386A
CN1440386A CN01812353A CN01812353A CN1440386A CN 1440386 A CN1440386 A CN 1440386A CN 01812353 A CN01812353 A CN 01812353A CN 01812353 A CN01812353 A CN 01812353A CN 1440386 A CN1440386 A CN 1440386A
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B·普法伊费尔
Y－M·吉诺
G·科克雷尔
S·贝耶
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Abstract

本发明涉及γ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。

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新的γ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
本发明涉及新的γ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EP 0 049 658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EP 0 308 341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γ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(％)
    6.298     14.02     630     39.8
    7.480     11.81     380     24
    8.700     10.16     1584     100
    9.276     9.53     318     20.1
    10.564     8.37     526     33.2
    11.801     7.49     54     3.4
    12.699     6.96     86     5.4
    13.661     6.48     178     11.2
    14.095     6.28     163     10.3
    14.332     6.17     290     18.3
    14.961     5.92     161     10.2
    15.793     5.61     128     8.1
    16.212     5.46     179     11.3
    16.945     5.23     80     5.1
    17.291     5.12     92     5.8
    17.825     4.97     420     26.5
    18.100     4.90     159     10
    18.715     4.74     89     5.6
    19.017     4.66     118     7.4
    19.362     4.58     134     8.5
    19.837     4.47     133     8.4
    20.609     4.31     95     6
    21.232     4.18     257     16.2
    21.499     4.13     229     14.5
    21.840     4.07     127     8
    22.129     4.01     191     12.1
    22.639     3.92     137     8.6
    23.000     3.86     88     5.6
    23.798     3.74     147     9.3
    24.170     3.68     70     4.4
    25.066     3.55     167     10.5
    25.394     3.50     165     10.4
    26.034     3.42     84     5.3
    26.586     3.35     75     4.7
    27.541     3.24     74     4.7
    28.330     3.15     85     5.4
    29.589     3.02     96     6.1
本发明还涉及一种制备γ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氯仿中的溶液，然后将溶液快速冷却至0℃并在搅拌后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0-5℃，通过过滤收集由此得到的固体。将该固体悬浮于氯仿中，将悬浮液在室温下搅拌5-10天，然后通过过滤收集固体。
·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EP 0 308 341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)化合物在氯仿中的浓度优选为150-300g/升。
·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/升。所得固体在氯仿中的浓度优选为100-150g/升。
本发明还涉及药物组合物，其包含γ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：γ结晶形式的哌林多普利叔丁基胺盐
将100g根据专利说明书EP 0 308 341所述的方法得到的哌林多普利叔丁基胺盐溶于500ml在回流下加热的氯仿中。
然后将该溶液冷却至0℃并在该温度下搅拌过夜。通过过滤收集所得固体。粉末X射线衍射图：
γ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(％)
    6.298     14.02     630     39.8
    7.480     11.81     380     24
    8.700     10.16     1584     100
    9.276     9.53     318     20.1
    10.564     8.37     526     33.2
    11.801     7.49     54     3.4
    12.699     6.96     86     5.4
    13.661     6.48     178     11.2
    14.095     6.28     163     10.3
    14.332     6.17     290     18.3
    14.961     5.92     161     10.2
    15.793     5.61     128     8.1
    16.212     5.46     179     11.3
    16.945     5.23     80     5.1
    17.291     5.12     92     5.8
    17.825     4.97     420     26.5
    18.100     4.90     159     10
    18.715     4.74     89     5.6
    19.017     4.66     118     7.4
    19.362     4.58     134     8.5
    19.837     4.47     133     8.4
    20.609     4.31     95     6
    21.232     4.18     257     16.2
    21.499     4.13     229     14.5
    21.840     4.07     127     8
    22.129     4.01     191     12.1
    22.639     3.92     137     8.6
    23.000     3.86     88     5.6
    23.798     3.74     147     9.3
    24.170     3.68     70     4.4
    25.066     3.55     167     10.5
    25.394     3.50     165     10.4
    26.034     3.42     84     5.3
    26.586     3.35     75     4.7
    27.541     3.24     74     4.7
    28.330     3.15     85     5.4
    29.589     3.02     96     6.1
实施例2：γ结晶形式的哌林多普利叔丁基胺盐
将125g根据专利说明书EP 0 308 341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。
然后使该溶液的温度快速达到0-5℃。
然后通过过滤收集所得固体并悬浮于750g氯仿中。将悬浮液在室温下搅拌5-10天，然后通过过滤收集固体。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 (11)

1.γ结晶形式的式(I)化合物：
Figure A0181235300021
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：     2θ角(°)   晶面间距d()    强度   相对强度(％)     6.298     14.02     630     39.8     7.480     11.81     380     24     8.700     10.16     1584     100     9.276     9.53     318     20.1     10.564     8.37     526     33.2     11.801     7.49     54     3.4     12.699     6.96     86     5.4     13.661     6.48     178     11.2     14.095     6.28     163     10.3     14.332     6.17     290     18.3     14.961     5.92     161     10.2     15.793     5.61     128     8.1     16.212     5.46     179     11.3     16.945     5.23     80     5.1     17.291     5.12     92     5.8     17.825     4.97     420     26.5     18.100     4.90     159     10     18.715     4.74     89     5.6     19.017     4.66     11 8     7.4     19.362     4.58     134     8.5     19.837     4.47     133     8.4     20.609     4.31     95     6
    21.232     4.18     257     16.2     21.499     4.13     229     14.5     21.840     4.07     127     8     22.129     4.01     191     12.1     22.639     3.92     137     8.6     23.000     3.86     88     5.6     23.798     3.74     147     9.3     24.170     3.68     70     4.4     25.066     3.55     167     10.5     25.394     3.50     165     10.4     26.034     3.42     84     5.3     26.586     3.35     75     4.7     27.541     3.24     74     4.7     28.330     3.15     85     5.4     29.589     3.02     96     6.1
2.制备根据权利要求1的γ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氯仿中的溶液，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γ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，通过过滤收集由此得到的固体，将其悬浮于氯仿中，将悬浮液在室温下搅拌5-10天，然后通过过滤收集固体。
4.根据权利要求2或3的方法，其特征在于使用通过专利说明书EP 0308 341中所述的制备方法得到的式(I)化合物。
5.根据权利要求2的方法，其特征在于式(I)化合物在氯仿中的浓度为150-300g/升。
6.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/升。
7.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。
8.根据权利要求7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。
9.根据权利要求8的药物组合物，用于制造用于治疗心血管疾病的药物。
10.根据权利要求7-9中任一项的药物组合物，其特征在于它还包含利尿药。
11.根据权利要求10所述的药物组合物，其特征在于利尿药为吲满胺。
CNB018123538A 2000-07-06 2001-07-06 新的γ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 Expired - Fee Related CN1328258C (zh)

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FR00/08791 2000-07-06

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