CN1121690A - 噻唑烷二酮在治疗动脉粥样硬化和摄食性疾病方面的用途 - Google Patents
噻唑烷二酮在治疗动脉粥样硬化和摄食性疾病方面的用途 Download PDFInfo
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Abstract
本发明提供式(I)化合物或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物在制造用于治疗和/或预防动脉粥样硬化和/或调节食欲和摄食的药物方面的用途,式(I)中A1、A2、R1、R2、R3和n的定义见说明书。
Description
本发明涉及某些取代的噻唑烷二酮衍生物和含这样的化合物的药用组合物的新用途。
一些欧洲专利中请(公开号0008203、0139421、0155845、0177353、0193256、0207581和0208420)涉及了据称具有降血糖和降血脂活性的噻唑烷二酮衍生物。Chem.Pharm.Bull 30(10)3580-3600也涉及了一些具有降血糖和降血脂活性的噻唑烷二酮衍生物。
公开号为0306228的欧洲专利申请公开了一些式(A)取代的噻唑烷二酮衍生物:或其互变异构体和/或其药学上可接受的盐,和/或其药学上可接受的溶剂化物,式中:A1a代表取代的或未取代的芳杂环基;R1a代表氢原子、烷基、酰基、芳烷基,其中芳基部分可以是被取代的或未被取代的,或者代表取代的或未取代的芳基;R2a和R3a各自代表氢,或R2a和R3a一起代表一个键;A2a代表具有至多5个取代基的苯环;n’代表2至6范围内的一个整数。这样的化合物据称尤其可用于治疗和/或预防心血管疾病和某些摄食性疾病。
现已惊异地发现,这些化合物在治疗和/或预防动脉粥样硬化方面具有特殊的用途。此外,这些化合物特别可用于调节与摄食不足相关的疾病如神经性厌食症和与摄食过度相关的疾病如肥胖症和贪食症的患者的食欲和摄食。
因此,本发明提供式(I)化合物或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物在制造用于治疗和/或预防动脉粥样硬化和/或调节与摄食不足相关的疾病如神经性厌食症和与摄食过度相关的疾病如肥胖症和贪食症的患者的食欲和摄食的药物方面的用途:式中:A1代表取代的或未取代的芳杂环基;R1代表氢原子、烷基、酰基、芳烷基,其中芳基部分可以是被取代的或未被取代的,或者代表取代的或未取代的芳基;R2和R3各自代表氢,或R2和R3一起代表一个键;A2代表具有至多5个取代基的苯环;n代表2至6范围内的一个整数。
适宜的芳杂环基包括取代的或未取代的单环或稠合环芳杂环基,它们在各环中含有至多4个选自氧、硫或氮的杂原子。
优选的芳杂环基包括具有4至7、优选5或6个环原子的取代的或未取代的单环芳杂环基。
特别是,所述芳杂环基包含1、2或3个、尤其是1或2个选自氧、硫或氮的杂原子。
当A1代表五元芳杂环基时,适宜的A1包括噻唑基和噁唑基,尤其是噁唑基。
当A1代表六元芳杂环基时,适宜的A1包括吡啶基或嘧啶基。
R2和R3宜各自代表氢。
A1最好代表式(a)、(b)或(c)基团:
式中:R4和R5各自独立地代表氢原子、烷基或取代的或未取代的芳基,或者当R4和R5各自与相邻的碳原子相连时,R4和R5同与.之相连的碳原子一起形成苯环,其中由R4和R5一起代表的各碳原子可以是被取代的或未被取代的;在式(a)基团中,X代表氧或硫。
A1宜代表上述的式(a)基团。
A1宜代表上述的式(b)基团。
A1宜代表上述的式(c)基团。
式中R6和R7各自独立地代表氢、卤素、取代的或未取代的烷基或烷氧基。
R6和R7宜各自独立地代表氢、卤素、烷基或烷氧基。
R6优选代表氢。R7优选代表氢。
最好是,R6和R7均代表氢。
更为优选的是,R4和R5各自独立地代表氢、烷基或取代的或未取代的苯基,更优选R4和R5各自独立地代表氢、烷基或苯基。
对于式(a)基团,R4和R5最好一起代表式(d)基团。
对于式(b)或(c)基团,R4和R5最好均代表氢。
应当知道的是,A2的5个取代基包括3个可任选的取代基。A2基团的适宜的可任选的取代基包括卤素、取代的或未取代的烷基或烷氧基。
式中R8和R9各自独立地代表氢、卤素、取代的或未取代的烷基或烷氧基。
R8和R9宜各自独立地代表氢、卤素、烷基或烷氧基。最好是R8和R9各自代表氢。
X优选代表氧。X优选代表硫。
式中A1、R1、R2、R3和n与式(I)中的定义相同,R8和R9与式(e)中的定义目同。
n宜代表整数2、3或4,特别是2或3,尤其是2。
R1宜代表氢、烷基、酰基,尤其是乙酰基或苄基。
当R1代表烷基时,所述烷基的实例包括甲基和异丙基。R1最好代表甲基。
如上所示,式(I)化合物可以以几种互变异构体之一存在,所有这些互变异构体均包括在本发明范围内。应当懂得,本发明包括式(I)化合物及其药学上可接受的盐的所有的异构体,包括其任何立体异构体,而不管它是单一的异构体还是异构体的混合物。
任何杂环基团的适宜的取代基包括至多4个选自下列一组基团的取代基:烷基、烷氧基、芳基和卤素,或者任何两个在相邻碳原子上的取代基同与之相连的碳原子一起可以形成芳基,最好是苯环,其中由所述的两个取代基代表的芳基的碳原子本身可以是被取代的或未被取代的。
本文所用的术语“芳基”包括被至多5个、优选至多3个选自下列的基团任选地取代的苯基和萘基:卤素、烷基、苯基、烷氧基、卤代烷基、羟基、氨基、硝基、羧基、烷氧基羰基、烷氧基羰基烷基、烷基羰基氧基或烷基羰基。
本文所用的术语“卤素”指氟、氯、溴和碘,优选氯。
本文所用的术语“烷基”和“烷氧基”涉及含有至多12个碳原子的具有直碳链或支碳链的基团。
本文所用的术语“酰基”包括烷基羰基。
适宜的烷基是C1-12烷基,尤其是C1-6烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基。
任何烷基的适宜的取代基均包括上面在术语“芳基”中所述的那些取代基。
适宜的药学上可接受的盐包括噻唑烷二酮部分的盐,适当时也包括羧基部分的盐。
噻唑烷二酮部分的适宜的药学上可接受的盐包括金属盐,尤其是碱金属盐例如锂盐、钠盐和钾盐。
羧基部分的适宜的药学上可接受的盐包括金属盐,例如铝盐;碱金属盐,例如钠或钾盐;碱土金属盐,例如钙或镁盐;以及铵盐或取代的铵盐,例如与低级烷基胺如三乙胺、羟基烷基胺如2-羟基乙胺、二(2-羟基乙基)胺或三(2-羟基乙基)胺、环烷基胺如二环己基胺形成的盐,或与普鲁卡因、二苄基哌啶、N-苄基-b-苯乙基胺、脱氢枞胺、N,N’-双脱氢枞胺、葡糖胺、N-甲基葡糖胺或吡啶类型的碱如吡啶、可力丁或喹啉形成的盐。
适宜的药学上可接受的溶剂化物包括水合物。
式(I)化合物的盐和/或溶剂化物可以按照常规程序来制备并分离,例如钠盐可以通过在甲醇中使用甲醇钠来制备。
噻唑烷二酮部分的适宜的药学上可接受的盐包括金属盐,尤其是碱金属盐如锂盐、钠盐和钾盐。
优选的式(I)化合物是5-[4-[2-(N-甲基-N-(2-吡啶基)氨基)乙氧基]苄基]噻唑烷-2,4-二酮或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物。
式(I)化合物、或其互变异构体、和/或其药学上可接受的盐、和/或其药学上可接受的溶剂化物可用EP0306228中所述的方法来制备。EP0306228的内容被参考结合入本文中。
如上所述,本发明化合物具有有效的治疗特性。
式(I)化合物、或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物可以直接使用,或者最好是以还包括药学上可接受的载体的药用组合物形式使用。
本文中所用的术语“药学上可接受的”包括人和兽均能使用的化合物、组合物和成分,例如术语“药学上可接受的盐”包括兽医学上可接受的盐。
若需要,所述组合物可以是带有使用说明书的包装形式。
本发明的药用组合物通常适于口服,当然也可以设想通过其它途径如注射和经皮吸收使用的组合物。
特别适宜的口服用组合物是单位剂型如片剂和胶囊剂,其它固定的单位剂型例如装在小袋中的粉剂也可以使用。
按照常规的制药方法,载体可经包括稀释剂、填充剂、崩解剂、润湿剂、润滑剂、着色剂、矫味剂或其它常规助剂。
典型的载体包括例如微晶纤维素、淀粉、淀粉羟基乙酸钠、聚乙烯吡咯烷酮、聚乙烯基聚吡咯烷酮、硬脂酸镁、十二烷基硫酸钠或蔗糖。
最宜将所述组合物配制成单位剂型。这样的单位剂量中活性成分的含量一般应在0.1-1000mg、更常用的是0.1-500mg、尤其是0.1-250mg范围内。
本发明还提供治疗人或其它哺乳动物动脉粥样硬化的方法,它包括给需要治疗的人或其它哺乳动物使用有效且无毒量的式(I)化合物,或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物。
本发明还提供调节人或其它哺乳动物中与摄食不足相关的疾病如神经性厌食症和与摄食过度有关的疾病如肥胖症和贪食症的患者的食欲和摄食的方法,它包括给需要此调节的人或其它哺乳动物使用有效且无毒量的式(I)化合物,或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物。
方便的是,所述活性成分可以上文所定义的药用组合物形式来使用,这构成本发明的一个特别方面。
在上述的治疗中,通式(I)化合物或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物可以一定的剂量例如上面所述的那些剂量摄入,每天使用1至6次以使得体重为70Kg的成人的总日剂量应一般在0.1-6000mg范围内,更常用的是在约1-1500mg范围内。
在对除人以外的哺乳动物尤其是狗进行治疗和/或预防时,所述活性成分可以经口服,通常每天一次或两次,用量在约0.025mg/kg-25mg/kg例如0.1mg/kg-20mg/kg范围内。
式(I)化合物、其互变异构体、其药学上可接受的盐或其药学上可接受的溶剂化物的治疗活性可以用常规实验方法予以证实,例如抗动脉粥样硬化活性可以用Journal of Clinical Investigations 1992,第89卷,第706-711页中公开的方法予以证实。
Claims (13)
2.按照权利要求1的用途,其中在式(I)化合物中,A1代表在环上含有至多4个选自氧、硫或氮的杂原子的取代或未取代的单环或稠合环芳杂环基团。
4.按照权利要求3的用途,其中R4和R5各自独立地代表氢、烷基或取代的或未取代的苯基。
6.按照权利要求5的用途,其中在式(d)基团中,R6和R7均代表氢。
8.按照权利要求7的用途,其中在式(e)基团中,R8和R9各自代表氢。
10.按照权利要求1至9之任一项的用途,其中在式(I)化合物中,n代表整数2或3。
11.按照权利要求1至3之任一项的用途,其中在式(I)化合物中,R1代表甲基。
12.按照权利要求1至3之任一项的用途,其中式(I)化合物选自下列一组化合物或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物:
5-(4-[2-(N-甲基-N-(2-苯并噻唑基)氨基)乙氧基]苄基-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-苯并噻唑基)氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-苯并噁唑基)氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-苯并噁唑基)氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-嘧啶基)氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-嘧啶基)氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4,5-二甲基噻唑基)]氨基)乙氧基)苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4,5-二甲基噻唑基)]氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-噻唑基)氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-噻唑基)氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-[4-(2-(N-甲基-N-(2-(4-苯基噻唑基))氨基)乙氧基)苄基]-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-(4-苯基噻唑基))氨基)乙氧基)亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4-苯基-5-甲基噻唑基)]氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4-苯基-5-甲基噻唑基)]氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4-甲基-5-苯基噻唑基)]氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4-甲基-5-苯基噻唑基)]氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-[4-(2-(N-甲基-N-[2-(4-甲基噻唑基)]氨基)乙氧基)苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4-甲基噻唑基)]氨基)乙氧基)亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(5-苯基恶唑基)]氨基)乙氧基)苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(5-苯基噁唑基)]氨基)乙氧基)亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4,5-二甲基噁唑基)]氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-[2-(4,5-二甲基噁唑基)]氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮;
5-[4-(2-(2-嘧啶基氨基)乙氧基)苄基)-2,4-噻唑烷二酮
5-[4-(2-(2-嘧啶基氨基)乙氧基)亚苄基)-2,4-噻唑烷二酮
5-(4-[2-(N-乙酰基-N-(2-嘧啶基)氨基)乙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-(2-(N-(2-苯并噻唑基)-N-苄基氨基)乙氧基)亚苄基)-2,4-噻唑烷二酮;
5-(4-(2-(N-(2-苯并噻唑基)-N-苄基氨基)乙氧基)苄基)-2,4-噻唑烷二酮;
5-(4-(3-(N-甲基-N-(2-苯并噁唑基)氨基)丙氧基]苄基)-2,4-噻唑烷二酮;
5-(4-[3-(N-甲基-N-(2-苯并噁唑基)氨基)丙氧基]亚苄基)-2,4-噻唑烷二酮;
5-(4-[2-(N-甲基-N-(2-吡啶基)氨基)乙氧基]苄基)-2,4-噻唑烷二酮;和
5-(4-[2-(N-甲基-N-(2-比啶基)氨基)乙氧基]亚苄基)-2,4-噻唑烷二酮。
13.按照权利要求1的用途,其中式(I)化合物是5-(4-[2-(N-甲基-N-(2-吡啶基)氨基)乙氧基]苄基)-2,4-噻唑烷二酮;或其互变异构体和/或其药学上可接受的盐和/或其药学上可接受的溶剂化物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GB939308487A GB9308487D0 (en) | 1993-04-23 | 1993-04-23 | Novel compounds |
GB9308487.9 | 1993-04-23 |
Publications (1)
Publication Number | Publication Date |
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CN1121690A true CN1121690A (zh) | 1996-05-01 |
Family
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CN94191887A Pending CN1121690A (zh) | 1993-04-23 | 1994-04-25 | 噻唑烷二酮在治疗动脉粥样硬化和摄食性疾病方面的用途 |
Country Status (14)
Country | Link |
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EP (2) | EP1306086A3 (zh) |
JP (1) | JPH08509486A (zh) |
CN (1) | CN1121690A (zh) |
AT (1) | ATE245418T1 (zh) |
AU (1) | AU6574394A (zh) |
CA (1) | CA2161116A1 (zh) |
DE (1) | DE69432973T2 (zh) |
DK (1) | DK0695183T3 (zh) |
ES (1) | ES2202322T3 (zh) |
GB (1) | GB9308487D0 (zh) |
PT (1) | PT695183E (zh) |
SG (1) | SG47127A1 (zh) |
WO (1) | WO1994025026A1 (zh) |
ZA (1) | ZA942774B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1620453B (zh) * | 2000-09-29 | 2010-12-08 | 史密斯克莱·比奇曼公司 | 噻唑烷二酮衍生物及其作为抗糖尿病药的用途 |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5902726A (en) * | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
US5925656A (en) * | 1995-04-10 | 1999-07-20 | Dr. Reddy's Research Foundation | Compounds having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
JPH09323930A (ja) * | 1996-04-04 | 1997-12-16 | Takeda Chem Ind Ltd | 悪液質の予防・治療剤 |
US5919782A (en) * | 1996-05-06 | 1999-07-06 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
US5889032A (en) * | 1996-05-06 | 1999-03-30 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
US5801173A (en) * | 1996-05-06 | 1998-09-01 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
US5889025A (en) * | 1996-05-06 | 1999-03-30 | Reddy's Research Foundation | Antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
US6372750B2 (en) | 1996-07-01 | 2002-04-16 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compounds containing them and their use in the treatment of diabetes and related diseases |
USRE39266E1 (en) * | 1996-07-01 | 2006-09-05 | Dr. Reddy's Laboratories, Limited | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
US6114526A (en) | 1996-07-01 | 2000-09-05 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
US5885997A (en) * | 1996-07-01 | 1999-03-23 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
CZ298812B6 (cs) | 1996-07-01 | 2008-02-13 | Dr. Reddy's Laboratories Limited | Azolidindionové deriváty, způsob jejich přípravy, farmaceutické kompozice s jejich obsahem a jejich použití v léčbě diabetu a příbuzných nemocí |
JP2008094852A (ja) * | 1996-07-15 | 2008-04-24 | Daiichi Sankyo Co Ltd | 医薬 |
AU2995497A (en) * | 1996-07-26 | 1997-11-19 | Dr. Reddy's Research Foundation | Thiazolidinedione compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions thereof |
US6011036A (en) * | 1997-04-15 | 2000-01-04 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic hypolipidemic antihypertensive properties process for their preparation and pharmaceutical compositions containing them |
US6011031A (en) * | 1997-05-30 | 2000-01-04 | Dr. Reddy's Research Foundation | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them |
HU225919B1 (en) * | 1999-12-18 | 2007-12-28 | Richter Gedeon Nyrt | Thiazolidine-derivatives, process for their preparation pharmaceutical and intermediates |
GB0023971D0 (en) * | 2000-09-29 | 2000-11-15 | Smithkline Beecham Plc | Novel pharmaceutical |
WO2009026172A2 (en) | 2007-08-17 | 2009-02-26 | The Regents Of The University Of California | New approach for designing diabetes drugs |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0306228B1 (en) * | 1987-09-04 | 1999-11-17 | Beecham Group Plc | Substituted thiazolidinedione derivatives |
GB8919417D0 (en) * | 1989-08-25 | 1989-10-11 | Beecham Group Plc | Novel compounds |
GB8919434D0 (en) * | 1989-08-25 | 1989-10-11 | Beecham Group Plc | Novel compounds |
TW222626B (zh) * | 1991-07-22 | 1994-04-21 | Pfizer | |
GB9218830D0 (en) * | 1992-09-05 | 1992-10-21 | Smithkline Beecham Plc | Novel compounds |
-
1993
- 1993-04-23 GB GB939308487A patent/GB9308487D0/en active Pending
-
1994
- 1994-04-21 ZA ZA942774A patent/ZA942774B/xx unknown
- 1994-04-25 DE DE69432973T patent/DE69432973T2/de not_active Expired - Fee Related
- 1994-04-25 CN CN94191887A patent/CN1121690A/zh active Pending
- 1994-04-25 EP EP03075243A patent/EP1306086A3/en not_active Withdrawn
- 1994-04-25 ES ES94913693T patent/ES2202322T3/es not_active Expired - Lifetime
- 1994-04-25 SG SG1996009433A patent/SG47127A1/en unknown
- 1994-04-25 PT PT94913693T patent/PT695183E/pt unknown
- 1994-04-25 EP EP94913693A patent/EP0695183B1/en not_active Expired - Lifetime
- 1994-04-25 AT AT94913693T patent/ATE245418T1/de not_active IP Right Cessation
- 1994-04-25 AU AU65743/94A patent/AU6574394A/en not_active Abandoned
- 1994-04-25 CA CA002161116A patent/CA2161116A1/en not_active Abandoned
- 1994-04-25 DK DK94913693T patent/DK0695183T3/da active
- 1994-04-25 JP JP6524013A patent/JPH08509486A/ja not_active Ceased
- 1994-04-25 WO PCT/GB1994/000879 patent/WO1994025026A1/en active IP Right Grant
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1620453B (zh) * | 2000-09-29 | 2010-12-08 | 史密斯克莱·比奇曼公司 | 噻唑烷二酮衍生物及其作为抗糖尿病药的用途 |
Also Published As
Publication number | Publication date |
---|---|
ZA942774B (en) | 1995-04-12 |
JPH08509486A (ja) | 1996-10-08 |
DK0695183T3 (da) | 2003-11-10 |
SG47127A1 (en) | 1998-03-20 |
PT695183E (pt) | 2003-12-31 |
CA2161116A1 (en) | 1994-11-10 |
DE69432973D1 (de) | 2003-08-28 |
EP0695183A1 (en) | 1996-02-07 |
WO1994025026A1 (en) | 1994-11-10 |
DE69432973T2 (de) | 2004-05-06 |
ATE245418T1 (de) | 2003-08-15 |
ES2202322T3 (es) | 2004-04-01 |
EP1306086A2 (en) | 2003-05-02 |
AU6574394A (en) | 1994-11-21 |
EP0695183B1 (en) | 2003-07-23 |
EP1306086A3 (en) | 2003-08-27 |
GB9308487D0 (en) | 1993-06-09 |
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