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CN103626710A - 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸的共晶及其制备方法 - Google Patents

2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸的共晶及其制备方法 Download PDF

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CN103626710A
CN103626710A CN201310706091.6A CN201310706091A CN103626710A CN 103626710 A CN103626710 A CN 103626710A CN 201310706091 A CN201310706091 A CN 201310706091A CN 103626710 A CN103626710 A CN 103626710A
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acetic acid
triazole
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base sulfenyl
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陈敏华
张炎锋
杨朝惠
张晓宇
王鹏
李丕旭
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SUZHOU PENGXU PHARMATECH Co Ltd
Crystal Pharmatech Co Ltd
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Crystal Pharmatech Co Ltd
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Priority to CN201310706091.6A priority Critical patent/CN103626710A/zh
Publication of CN103626710A publication Critical patent/CN103626710A/zh
Priority to CN201710052927.3A priority patent/CN106866559B/zh
Priority to CN201410783346.3A priority patent/CN104529919B/zh
Priority to US15/106,361 priority patent/US9969701B2/en
Priority to PCT/US2014/071501 priority patent/WO2015095703A1/en
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract

本发明涉及化合物2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸的两种共晶型，分别涉及2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A和2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B。

Description

2-(5-溴-4-(4-环丙基萘-1-基)-4H-1,2,4-三唑-3-基硫基)乙酸的共晶及其制备方法
所属技术领域
本发明涉及化学医药领域，特别是涉及2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸的共晶及其制备方法。 
背景技术
2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸（Lesinurad）是一种促尿酸排泄口服药，通过抑制肾近曲小管的尿酸转运子URAT1而治疗有高尿酸血症的痛风患者。该药物的结构如下所示： 
Figure BDA0000442385520000011
WO2012092395A2公开了2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸的结晶多晶型形式1和形式2。多晶型形式1的特征在于，其X射线衍射图在10.32、18.84及20.75°2θ±0.1°2θ处存在峰。多晶型形式2的特征在于，其X-射线衍射图在10.46、18.76及19.83°2θ±0.1°2θ处存在峰。 
WO2011085009A2公开了2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸钠的结晶多晶型及固体中间相型。包括2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸钠多晶型A，多晶型B，多晶型B′，多晶型 C，多晶型D，多晶型E以及2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸钠固体中间相1，固体中间相2，固体中间相3。 
发明内容
本发明公开了2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型和2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型。 
一方面，本发明公开了一种2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型，本发明中命名为共晶型A。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A，其特征在于，其X射线衍射图中在2theta值为21.9°±0.2°、18.1°±0.2°和20.2°±0.2°处具有特征峰。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A，其特征还在于，其X射线衍射图中在2theta值为12.6°±0.2°、13.1°±0.2°、14.8°±0.2°、18.9°±0.2°、19.8°±0.2°、20.5°±0.2°、24.8°±0.2°处具有特征峰，如图1所示。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A，其特征在于，其差示扫描量热分析(DSC)在58.1℃、66.2℃、附近分别出现吸热峰,在起始温度152.6℃附近开始出现另一个吸热峰，如图2所示。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A，其特征在于，其加热至接近85.0℃时失重约 2.8%，其热重分析图如图3所示。 
本发明提供一种2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸共晶的制备方法，其特征在于，其制备方法包括如下步骤：将2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸（Lesinurad）粉末溶解于有机溶剂中，将摩尔比2:1（脯氨酸/Lesinurad）的脯氨酸加入该溶液中，室温条件下搅拌，离心得到的固体即为该共晶型。 
另一方面，本发明公开了一种2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型，本发明中命名为共晶型B。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B，其特征在于，其X射线衍射图中在2theta值为21.3°±0.2°、20.9°±0.2°和17.9°±0.2°处具有特征峰。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B，其特征还在于，其X射线衍射图中在2theta值为10.9°±0.2°、11.4°±0.2°、13.0°±0.2°、17.4°±0.2°、24.3°±0.2°、25.4°±0.2°、27.3°±0.2°处具有特征峰，如图4所示。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B，其特征在于，其差示扫描量热分析(DSC)在52.8℃、111.3℃附近分别开始出现吸热峰，如图5所示。 
更进一步的，本发明提供的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B，其特征在于，其加热至接近135.0℃时失重约10.0%，其热重分析图如图6所示。 
本发明提供一种2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基) 乙酸-乙醇酸的共晶型的制备方法，其特征在于，其制备方法包括如下步骤：将2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸（Lesinurad）粉末溶解于有机溶剂或有机溶剂和水的混合溶剂中，将摩尔比1:1（乙醇酸/Lesinurad）的乙醇酸加入该溶液中，室温条件下缓慢挥发即得到该共晶型。 
附图说明
图1为2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和脯氨酸的共晶型A的XRPD图。 
图2为2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和脯氨酸的共晶型A的DSC图。 
图3为2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和脯氨酸的共晶型A的TGA图。 
图4为2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和乙醇酸的共晶型B的XRPD图。 
图5为2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和乙醇酸的共晶型B的DSC图。 
图6为2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和乙醇酸的共晶型B的TGA图。 
具体实施方式
以下将通过具体实施例进一步阐述本发明，但并不用于限制本发明的保护 范围。本领域技术人员可在权利要求范围内对制备方法和使用仪器作出改进，这些改进也应视为本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。 
下述实施例中，除非另有说明，所述的试验方法通常按照常规条件或制造厂商建议的条件实施；所示的原料、试剂均可通过市售购买的方式获得。 
本发明所述的X射线粉末衍射图在Panalytical Empyrean X射线粉末衍射仪上采集。本发明所述的X射线粉末衍射的方法参数如下： 
X射线反射参数：CuKa 
Kα1
Figure BDA0000442385520000051
：1.540598；Kα2
Figure BDA0000442385520000052
：1.544426 
Kα2/Kα1强度比例：0.50 
电压：45仟伏特（kV) 
电流：40毫安培（mA) 
发散狭缝：自动 
扫描模式：连续 
扫瞄范围：自3.0至40.0度 
取样步长：0.013度 
每步测量时间：78.795秒/步 
本发明所述的差示扫描量热分析图在TAQ2000差示扫描量热仪上采集。本发明所述的差示扫描量热分析的方法参数如下： 
温度范围/℃:室温-300℃ 
扫描速率/℃/分钟:10℃/分钟 
保护气体：氮气50毫升/分钟 
本发明所述的热重分析图在TAQ500热重分析仪上采集。本发明所述的热重分析的方法参数如下： 
温度范围/℃:室温-320℃ 
扫描速率/℃/分钟:10℃/分钟 
保护气体：氮气60毫升/分钟 
实施例1： 
2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A的制备： 
将151.2mg2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸(Lesinurad)粉末溶解于1.0mL乙酸乙酯溶剂中，将84.8mg脯氨酸加入该溶液中，室温条件下搅拌24小时，离心得到的固体即为该晶型。 
所述的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-脯氨酸的共晶型A，其X射线粉末衍射图（XRPD）如图4所示，其特征在于，在2theta值为21.9°、18.1°、20.2°、12.6°、13.1°、14.8°、18.9°、19.8°、20.5°、24.8°处具有特征峰。 
实施例2： 
2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B的制备： 
将10mg2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸(Lesinurad)粉末溶解于0.3mL甲醇中，再将1.9mg乙醇酸加入该溶液中，得到澄清溶液，在室温条件下缓慢挥发至溶剂挥干，即可得到乙醇酸的共晶型。 
所述的2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸-乙醇酸的共晶型B，其X射线粉末衍射图（XRPD）如图4所示，其特征在于，在2theta值为21.3°、20.9°、17.9°、10.9°、11.4°、13.0°、17.4°、24.3°、25.4°、27.3°处具有特征峰。 

Claims (8)

1.一种2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸（Lesinurad）和脯氨酸的共晶型A，其特征在于，其X射线衍射图中在2theta值为21.9°±0.2°、18.1°±0.2°和20.2°±0.2°处具有特征峰。
2.根据权利要求1所述的共晶型A，其特征还在于，其X射线衍射图中在2theta值为12.6°±0.2°、13.1°±0.2°、14.8°±0.2°、18.9°±0.2°、19.8°±0.2°、20.5°±0.2°、24.8°±0.2°处具有特征峰。
3.根据权利要求1所述的共晶型A，其特征在于，其X-射线衍射（XRPD）图基本上与图1一致。
4.根据权利要求1所述的共晶型A，其特征在于，其制备方法是将2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸（Lesinurad）粉末溶解于有机溶剂中，将摩尔比2:1（脯氨酸/Lesinurad）的脯氨酸加入该溶液中，室温条件下搅拌，离心得到的固体即为该共晶型。
5.一种2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸和乙醇酸的共晶型B，其特征在于，其X射线衍射图中在2theta值为21.3°±0.2°、20.9°±0.2°和17.9°±0.2°处具有特征峰。
6.根据权利要求5所述的共晶型B，其特征还在于，其X射线衍射图中在2theta值为10.9°±0.2°、11.4°±0.2°、13.0°±0.2°、17.4°±0.2°、24.3°±0.2°、25.4°±0.2°、27.3°±0.2°处具有特征峰。
7.根据权利要求5所述的共晶型B，其特征在于，其X-射线衍射（XRPD）图基本上与图4一致。
8.根据权利要求5所述的共晶型B，其特征在于，其制备方法是将2-(5-溴-4-(4-环丙基萘-1-基)-4H-1，2，4-三唑-3-基硫基)乙酸（Lesinurad）粉末溶解于有机溶剂或有机溶剂和水的混合溶剂中，将摩尔比1:1（乙醇酸/Lesinurad）的乙醇酸加入该溶液中，在室温条件下缓慢挥发即得到该共晶型。
CN201310706091.6A 2013-12-20 2013-12-20 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸的共晶及其制备方法 Pending CN103626710A (zh)

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