Discovery of Ipragliflozin (ASP1941): A novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 10, 2012, Pages 3263-3279

  Imamura, Masakazu ^a   Nakanishi, Keita ^a   Suzuki, Takayuki ^a   Ikegai, Kazuhiro ^a   Shiraki, Ryota ^a   Ogiyama, Takashi ^a   Murakami, Takeshi ^a   Kurosaki, Eiji ^a   Noda, Atsushi ^b   Kobayashi, Yoshinori ^b   Yokota, Masayuki ^b   Koide, Tomokazu ^b   Kosakai, Kazuhiro ^b   Ohkura, Yasufumi ^b   Takeuchi, Makoto ^a   Tomiyama, Hiroshi ^b   Ohta, Mitsuaki ^a  

^a ASTELLAS PHARMA INC   (Japan)

^b Kotobuki Pharmaceutical Co Ltd   (Japan)

Author keywords

Benzothiophene; Diabetes; Ipragliflozin; SGLT2 inhibitor

Indexed keywords

GLUCOSE; IPRAGLIFLOZIN; SODIUM GLUCOSE COTRANSPORTER 2;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIDIABETIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG HALF LIFE; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; FEMALE; GLUCOSE BLOOD LEVEL; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; RAT; SINGLE DRUG DOSE;

ANIMALS; BLOOD GLUCOSE; CHO CELLS; CRICETINAE; DIABETES MELLITUS, TYPE 2; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; GLUCOSIDES; HUMANS; HYPOGLYCEMIC AGENTS; INHIBITORY CONCENTRATION 50; MALE; MICE; MOLECULAR STRUCTURE; RATS; RATS, SPRAGUE-DAWLEY; SODIUM-GLUCOSE TRANSPORTER 2; THIOPHENES;

MUS; RATTUS;

EID: 84860492610     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.03.051     Document Type: Article

References (32)

1. L.L. Lipscombe, and J.E. Hux Lancet 369 2007 750
2. N.J. Wareham, and N.G. Forouhi Diabetologia 48 2005 1454
3. S. Wild, G. Roglic, A. Green, R. Sicree, and H. King Diabetes Care 27 2004 1047
4. R. Klein Diabetes Care 18 1995 258
5. A. Libel, M. Mata, and E. Eschwege Diabetologia 45 2002 S23
6. S.H. Saydah, J. Fradkin, and C.C. Cowie J. Am. Med. Assoc. 291 2004 335
7. I. Idris, and R. Donnelly Diabetes Obes. Metab. 11 2009 79
8. E.M. Wright, B. Hirayama, A. Hazama, and D.D. Loo Soc. Gen. Physiol. Ser. 48 1993 229
9. E.M. Wright, E. Turk, K. Hager, L. Lescale-Matys, B. Hirayama, S. Supplisson, and D.D. Loo Acta Physiol. Scand., Suppl. 146 1992 201
10. B. Mackenzie, D.D. Loo, M. Panayotova-Heiermann, and E.M. Wright J. Biol. Chem. 271 1996 32678
11. Y. Kanai, W.S. Lee, G. You, D. Brown, and M.A. Hediger J. Clin. Invest. 93 1994 297
12. M. Kasahara, M. Maeda, S. Hayashi, Y. Mori, and T. Abe Biochim. Biophys. Acta 1536 2001 141
13. E. Turk, B. Zabel, S. Mundlos, J. Dyer, and E.M. Wright Nature 350 1991 354
14. L.P. van den Heuvel, K. Assink, E.M. Willemsen, and L. Monnens Hum. Genet. 111 2002 544
15. R. Santer, M. Kinner, R. Schneppenheim, G. Hillebrand, M. Kemper, J. Ehrich, P. Swift, F. Skovby, and J. Schaub J. Inherit. Metab. Dis. 23 2000 178
16. T. Asano, T. Ogihara, H. Katagiri, H. Sakoda, H. Ono, M. Fujishiro, M. Anai, H. Kurihara, and Y. Uchijima Curr. Med. Chem. 11 2004 2717
17. J.J. Neumiller, J.R. White Jr., and R.K. Campbell Drugs 70 2010 377
18. A. Oku, K. Ueta, K. Arakawa, T. Ishihara, M. Nawano, T. Asano, Y. Kanai, and H. Endou Diabetes 48 1999 1794
19. S.A. Doggrell, and J. Castanel Drugs Fut. 26 2001 750
20. K. Arakawa, T. Ishihara, A. Oku, M. Nawano, K. Ueta, K. Kitamura, M. Matsumoto, and A. Saito Br. J. Pharmacol. 132 2001 578
21. A. Oku, K. Ueta, K. Arakawa, T. Kano-Ishihara, M. Matsumoto, T. Adachi, K. Yasuda, K. Tsuda, and A. Saito Biol. Pharm. Bull. 23 2000 1434
22. T. Adachi, K. Yasuda, Y. Okamoto, N. Shihara, A. Oku, K. Ueta, K. Kitamura, A. Saito, I. Iwakura, Y. Yamada, H. Yano, Y. Seino, and K. Tsuda Metabolism 49 2000 990
23. Tsujihara, M. Hongu, K. Saito, H. Kawanishi, K. Kuriyama, M. Matsumoto, A. Oku, K. Ueta, M. Tsuda, and A. Saito J. Med. Chem. 42 1999 5311
24. A. Oku, K. Ueta, M. Nawano, K. Arakawa, T. Kano-Ishihara, M. Matsumoto, and A. Saito Eur. J. Pharmacol. 391 2000 183
25. M. Nawano, A. Oku, K. Ueta, I. Umebayashi, T. Ishihara, K. Arakawa, A. Saito, M. Anai, M. Kikuchi, and T. Asano Am. J. Physiol. Endocrinol. Metab. 278 2000 E535
26. Tomiyama, H.; Kobayashi, Y.; Noda, A.; Tomiyama, T. Jpn. Kokai Tokkyo Koho 2001, JP2001288178; Chem. Abstr. 2001, 135, 304104.
27. Ellsworth, B.; Washburn, W. N.; Sher, P. M.; Wu, G.; Meng, W. U.S. patent 6,414,126, 2002; Chem. Abstr. 2002, 137, 247879.
28. Ellsworth, B.; Washburn, W. N.; Sher, P. M.; Wu, G.; Meng, W. PCT Int. Appl. WO 01/27128, 2001; Chem. Abstr. 2001, 134, 281069.
29. Tahara, A.; Kurosaki, E.; Yokono, M.; Yamajuku, D.; Kihara, R.; Hayashizaki, Y.; Takasu, T.; Imamura, M.; Qun, L.; Tomiyama, H.; Kobayashi, Y.; Noda, A.; Sasamata, M.; Shibasaki, M. Naunyn Schmiedebergs Arch Pharmacol. 2011 Dec 3. [Epub ahead of print].
30. M.D. Lewis, J.K. Cha, and Y. Kishi J. Am. Chem. Soc. 104 1982 4976
31. M.D. Burkart, Z. Zhang, S.C. Hung, and C.H. Wong J. Am. Chem. Soc. 119 1997 11743
32. F. Castaneda, and R.K.-H. Kinne Mol. Cell. Biochem. 280 2005 91