CN102229558B - 西洛多辛的晶型δ、它的制备方法和包含它的药物组合物 - Google Patents
西洛多辛的晶型δ、它的制备方法和包含它的药物组合物 Download PDFInfo
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- 229960004953 silodosin Drugs 0.000 title claims abstract description 32
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
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Abstract
本发明提供了西洛多辛的一种新晶型δ、它的制备方法和包含它的药物组合物。该晶型以其粉末X射线衍射图表征。
Description
技术领域
本发明涉及西洛多辛或式(I)2，3-二氢-1-(3-羟丙基)-5-[(2R)-2-[2-[2-(2，2，2-三氟乙氧基)苯氧基]乙胺基]丙基]-1H-吲哚-7-甲酰胺的新晶型δ、它的制备方法和包含它的药物组合物。
背景技术
西洛多辛(silodosin)，2，3-二氢-1-(3-羟丙基)-5-[(2R)-2-[2-[2-(2，2，2-三氟乙氧基)苯氧基]乙胺基]丙基]-1H-吲哚-7-甲酰胺，是一种取代的吲哚啉类化合物，其分子结构式如下：
西洛多辛是一种α1-肾上腺素受体拮抗剂，对尿道平滑肌收缩具有选择性的抑制作用，并且是很有用的用于治疗由尿道组织堵塞有关、排尿控制神经紊乱有关、尿道功能性堵塞有关和由前列腺肥大、尿道狭窄、尿道结石、前列腺癌、神经性膀胱、下尿道疾病所致排尿困难的药物化合物，它不会导致强烈的降血压作用或直位性的血压过低。
西洛多辛和其在治疗与良性前列腺增生有关的排尿困难的用途在美国专利US 5387603中已有描述。中国专利200580037040.2中公开了西洛多辛的制备方法。中国专利03824796.8首次描述了西洛多辛α、β、γ三种晶型及其制备方法。
通常，无定型化合物虽然能显示较好的溶解性，但是因其稳定性差，它的比体积是变化的，且容易附着溶剂或吸湿，一般不适用于口服固体药物。而晶体化合物虽然溶解性较低，但其较稳定，和赋形剂比较相容，或者不会随时间变化，另外由于它通常不易吸湿，其比体积大概是恒定的，容易控制活性成分的量，因此固体口服药物使用晶体活性成分较好。
此外，很多化合物具有多晶型现象，各晶型显示了不同的溶解性或稳定性，所述差异会影响吸湿性或药效。因此，当用于药物的活性成分存在多晶型现象时，有必要确认药物所用多晶型物的特性。
鉴于西洛多辛的药学价值，获得纯度优良、具有很确定晶型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。
发明内容
本发明的目的是提供一种新的西洛多辛的晶型，即晶型δ。
更具体的而言，本发明涉及式(I)化合物的晶型δ，其以下列的粉末X射线衍射图表征，使用衍射计进行测定，以晶面间距d、2θ角、强度表示：
本发明还涉及式(I)化合物的晶型δ的制备方法，该方法的特征在于在110～120℃下加热或在惰性气体的保护下在110～120℃下加热西洛多辛直至完全熔化，然后缓慢冷却直至结晶。
获得这种晶型的优点是纯度优良、具有很确定晶型且重现性极好，并能够制备具有一致且可重现组成的药物制剂。
该种方法还具有经济实用、稳定性好、操作简便、环保等特点。
本发明还涉及包含作为活性成分的西洛多辛的晶型δ以及一种或多种适宜的辅料或载体的药物组合物。本发明的药物组合物中，可以更特别提及的是适于口服的剂型，优选的是片剂和胶囊剂。
附图说明
图1是西洛多辛晶型δ的X射线衍射图，所述纵坐标显示X射线的强度，以Kcps表示，横坐标显示为2θ(°)。
具体实施方式
下述实施方式更好的说明本发明的内容，但本发明不限于下述实例。
实施例1：西洛多辛的晶型δ
于110℃加热下使1g西洛多辛(2，3-二氢-1-(3-羟丙基)-5-[(2R)-2-[2-[2-(2，2，2-三氟乙氧基)苯氧基]乙胺基]丙基]-1H-吲哚-7-甲酰胺)完全熔化，然后缓慢冷却直至结晶，得到0.9g淡黄色固体，纯度99.0％，熔点99～101℃。
所得晶体以下列的粉末X射线衍射图表征，使用衍射计(铜对阴极)进行 测定，以晶面间距d、2θ角、强度表示：
实施例2：西洛多辛的晶型δ
在氮气保护下，于120℃加热下使1g西洛多辛(2，3-二氢-1-(3-羟丙基)-5-[(2R)-2-[2-[2-(2，2，2-三氟乙氧基)苯氧基]乙胺基]丙基]-1H-吲哚-7-甲酰胺)完全熔化，90℃保温30分钟后，放置室温缓慢冷却直至结晶，得到0.93g淡黄色固体，纯度99.5％，熔点99～101℃。
所得晶体以下列的粉末X射线衍射图表征，使用衍射计进行测定，以晶面间距d、2θ角、强度表示：
实施例3：胶囊1
配方：
西洛多辛的晶型δ 2.0g
甘露醇 66.5g
预胶化淀粉 30.0g
硬脂酸镁 1.0g
十二烷基硫酸钠 0.5g
根据以上配方，通过常规方法配制胶囊中包含2.0mg西洛多辛的晶型δ1000个胶囊。
实施例4：胶囊2
配方：
西洛多辛的晶型δ 2.0g
微晶纤维素 56.5g
乳糖 40.0g
硬脂酸镁 0.5g
十二烷基硫酸钠 1.0g
根据以上配方，通过常规方法配制胶囊中包含2.0mg西洛多辛晶型δ的1000个胶囊。
实施例5：胶囊3
配方：
西洛多辛的晶型δ 4.0g
乳糖 63.5g
预胶化淀粉 30.0g
滑石粉 0.5g
十二烷基硫酸钠 2.0g
根据以上配方，通过常规方法配制胶囊中包含4.0mg西洛多辛晶型δ的1000个胶囊。
实施例6：片剂1
配方：
西洛多辛的晶型δ 2.0g
甘露醇 59.0g
预胶化淀粉 30.0g
低取代羟丙基纤维素 5.0g
羟丙甲基纤维素E50 2.0g
硬脂酸镁 1.0g
十二烷基硫酸钠 1.0g
根据以上配方，通过常规方法配制片剂中包含2.0mg西洛多辛晶型δ的1000个胶囊。
实施例7：片剂2
配方：
西洛多辛的晶型δ 4.0g
甘露醇 56.0g
预胶化淀粉 30.0g
低取代羟丙基纤维素 5.0g
聚维酮K30 2.0g
滑石粉 1.0g
十二烷基硫酸钠 2.0g
根据以上配方，通过常规方法配制片剂中包含4.0mg西洛多辛晶型δ的1000个胶囊。
Claims (1)
1.西洛多辛晶型δ的制备方法，其特征是该方法包括如下步骤：
1)于110℃加热下使1g西洛多辛(2，3-二氢-1-(3-羟丙基)-5-[(2R)-2-[2-[2-(2，2，2-三氟乙氧基)苯氧基]乙胺基]丙基]-1H-吲哚-7-甲酰胺)完全熔化，缓慢冷却直至结晶，得到0.9g淡黄色固体，纯度99.0％，熔点99～101℃；
2)所得晶体以使用铜对阴极衍射计进行测定，其X射线衍射图如说明书图1所示。
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| WO2012077138A1 (en) * | 2010-12-09 | 2012-06-14 | Panacea Biotec Limited | Methods of crystallizing (r) -1- (3 -hydroxypropyl) -5- [2- [2- [2- ( 2, 2, 2 - trifluoroethoxy) phenoxy] ethylamino] propyl] indoline-7 -carboxamide |
| CN103360298A (zh) * | 2012-04-06 | 2013-10-23 | 昆明积大制药股份有限公司 | 一种β型西洛多辛晶体的制备方法 |
| CN109824569B (zh) * | 2019-04-04 | 2022-09-20 | 重庆医药高等专科学校 | 一种西罗多辛晶型i及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1694867A (zh) * | 2002-09-06 | 2005-11-09 | 橘生药品工业株式会社 | 口服固体药用晶体及治疗排尿困难的包含它的口服固体药 |
| CN101048376A (zh) * | 2004-10-27 | 2007-10-03 | 橘生药品工业株式会社 | 二氢吲哚化合物及其生产方法 |
| CN101412690A (zh) * | 2008-12-01 | 2009-04-22 | 巢杰 | 西洛多辛的药用酸加成盐及其制备方法和药物应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1694867A (zh) * | 2002-09-06 | 2005-11-09 | 橘生药品工业株式会社 | 口服固体药用晶体及治疗排尿困难的包含它的口服固体药 |
| CN101048376A (zh) * | 2004-10-27 | 2007-10-03 | 橘生药品工业株式会社 | 二氢吲哚化合物及其生产方法 |
| CN101412690A (zh) * | 2008-12-01 | 2009-04-22 | 巢杰 | 西洛多辛的药用酸加成盐及其制备方法和药物应用 |
Non-Patent Citations (2)
| Title |
|---|
| "Urodynamic Effects of Silodosin, a New a1A-Adrenoceptor Selective Antagonist, for the Treatment of Benign Prostatic Hyperplasia";Tomonori Yamanishi et al.;《Neurourology and Urodynamics》;20100515;第29卷;第558-562页 * |
| Tomonori Yamanishi et al.."Urodynamic Effects of Silodosin, a New a1A-Adrenoceptor Selective Antagonist, for the Treatment of Benign Prostatic Hyperplasia".《Neurourology and Urodynamics》.2010,第29卷第558-562页. |
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