Discovery of AM-1638: A Potent and Orally Bioavailable GPR40/FFA1 Full Agonist

被引:85
作者
Brown, Sean P. [1 ]
Dransfield, Paul J.
Vimolratana, Marc
Jiao, XianYun
Zhu, Liusheng
Pattaropong, Vatee
Sun, Ying
Liu, Jinqian
Luo, Jian
Zhang, Jane
Wong, Simon
Zhuang, Run
Guo, Qi
Li, Frank
Medina, Julio C.
Swaminath, Gayathri
Lin, Daniel C. -H.
Houze, Jonathan B.
机构
[1] Amgen Inc, Dept Therapeut Discovery Metab Disorders Pharmace, San Francisco, CA 94080 USA
来源
ACS MEDICINAL CHEMISTRY LETTERS | 2012年 / 3卷 / 09期
关键词
GPR40; full agonist; AM-1638; AMG; 837; insulin secretagogue; FFA1; TYPE-2; DIABETES-MELLITUS; RECEPTOR AGONIST; MODULATORS; ACIDS;
D O I
10.1021/ml300133f
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
GPR40 (FFA1) is a G-protein-coupled receptor, primarily expressed in pancreatic islets, the activation of which elicits increased insulin secretion only in the presence of elevated glucose levels. A potent, orally bioavailable small molecule GPR40 agonist is hypothesized to be an effective antidiabetic posing little or no risk of hypoglycemia. We recently reported the discovery of AMG 837 (1), a potent partial agonist of GPR40. Herein, we present the optimization from the GPR40 partial agonist 1 to the structurally and pharmacologically distinct GPR40 full agonist AM-1638 (21). Moreover, we demonstrate the improved in vivo efficacy that GPR40 full agonist 21 exhibits in BDF/DIO mice as compared to partial agonist 1.
引用
收藏
页码:726 / 730
页数:5
相关论文
共 14 条
[1]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[2]   Progress in the discovery and development of small-molecule modulators of G-protein-coupled receptor 40 (GPR40/FFA1/FFAR1): an emerging target for type 2 diabetes [J].
Bharate, Sandip B. ;
Nemmani, Kumar V. S. ;
Vishwakarma, Ram A. .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2009, 19 (02) :237-264
[3]   Structure-Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469 [J].
Christiansen, Elisabeth ;
Due-Hansen, Maria E. ;
Urban, Christian ;
Merten, Nicole ;
Pfleiderer, Michael ;
Karlsen, Kasper K. ;
Rasmussen, Sanne S. ;
Steensgaard, Mette ;
Hamacher, Alexandra ;
Schmidt, Johannes ;
Drewke, Christel ;
Petersen, Rasmus Koefoed ;
Kristiansen, Karsten ;
Ullrich, Susanne ;
Kostenis, Evi ;
Kassack, Matthias U. ;
Ulven, Trond .
ACS MEDICINAL CHEMISTRY LETTERS, 2010, 1 (07) :345-349
[4]   From the Triumvirate to the Ominous Octet: A New Paradigm for the Treatment of Type 2 Diabetes Mellitus [J].
DeFronzo, Ralph A. .
DIABETES, 2009, 58 (04) :773-795
[5]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[6]   AMG 837: A potent, orally bioavailable GPR40 agonist [J].
Houze, Jonathan B. ;
Zhu, Liusheng ;
Sun, Ying ;
Akerman, Michelle ;
Qiu, Wei ;
Zhang, Alex J. ;
Sharma, Rajiv ;
Schmitt, Michael ;
Wang, Yingcai ;
Liu, Jiwen ;
Liu, Jingian ;
Medina, Julio C. ;
Reagan, Jeff D. ;
Luo, Jian ;
Tonn, George ;
Zhang, Jane ;
Lu, Jenny Ying-Lin ;
Chen, Michael ;
Lopez, Edwin ;
Nguyen, Kathy ;
Yang, Li ;
Tang, Liang ;
Tian, Hui ;
Shuttleworth, Steven J. ;
Lin, Daniel C. -H. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) :1267-1270
[7]   Free fatty acids regulate insulin secretion from pancreatic β cells through GPR40 [J].
Itoh, Y ;
Kawamata, Y ;
Harada, M ;
Kobayashi, M ;
Fujii, R ;
Fukusumi, S ;
Ogi, K ;
Hosoya, M ;
Tanaka, Y ;
Uejima, H ;
Tanaka, H ;
Maruyama, M ;
Satoh, R ;
Okubo, S ;
Kizawa, H ;
Komatsu, H ;
Matsumura, F ;
Noguchi, Y ;
Shinobara, T ;
Hinuma, S ;
Fujisawa, Y ;
Fujino, M .
NATURE, 2003, 422 (6928) :173-176
[8]   A novel model of type 2 diabetes mellitus based on obesity induced by high-fat diet in BDF1 mice [J].
Karasawa, Hiroshi ;
Nagata-Goto, Seiko ;
Takaishi, Kiyosumi ;
Kumagae, Yoshihiro .
METABOLISM-CLINICAL AND EXPERIMENTAL, 2009, 58 (03) :296-303
[9]   AMG 837: A Novel GPR40/FFA1 Agonist that Enhances Insulin Secretion and Lowers Glucose Levels in Rodents [J].
Lin, Daniel C. -H. ;
Zhang, Jane ;
Zhuang, Run ;
Li, Frank ;
Kathy Nguyen ;
Chen, Michael ;
Thanhvien Tran ;
Lopez, Edwin ;
Lu, Jenny Ying Lin ;
Li, Xiaoyan Nina ;
Tang, Liang ;
Tonn, George R. ;
Swaminath, Gayathri ;
Reagan, Jeff D. ;
Chen, Jin-Long ;
Tian, Hui ;
Lin, Yi-Jyun ;
Houze, Jonathan B. ;
Luo, Jian .
PLOS ONE, 2011, 6 (11)
[10]   GPR40 (FFAR1) Modulators [J].
Medina, Julio C. ;
Houze, Jonathan B. .
ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 43, 2008, 43 :75-+