The isoxazolidine-3,5-dione hypoglycemic agent JTT-501 and other nonthiazolidinedione insulin sensitizers

Drugs of the Future

Volumn 24, Issue 8, 1999, Pages 893-898

  Shinkai, Hisashi ^a  

^a JT Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 [4 [2 (5 METHYL 2 PHENYL 4 OXAZOLYL)ETHOXY]PHENYL] 2 PROPYLAMINOPROPIONIC ACID; ANTIDIABETIC AGENT; BRL 48482; CIGLITAZONE; ISOXAZOLIDINE 3,5 DIONE; JTP 20993; PIOGLITAZONE; ROSIGLITAZONE; SB 213068; TROGLITAZONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; DRUG CONFORMATION; DRUG EFFECT; GLUCOSE METABOLISM; HYPERGLYCEMIA; HYPERINSULINEMIA; HYPERTRIGLYCERIDEMIA; INSULIN SENSITIVITY; LIPID METABOLISM; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0032878208     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1999.024.08.545999     Document Type: Review

References (38)

1. Porte, D. Jr., Schwartz, M.W. Diabetes complications: Why is glucose potentially toxic? Science 1996, 272: 699-700.
2. U.K. Prospective Diabetes Study (UKPDS) Group. Intensive blood-glucose control with sulphonylureas or insulin compared with conventional treatment and risk of complications in patients with type 2 diabetes (UKPDS 33). Lancet 1998, 352: 837-53.
3. Taylor, S.I., Accili, D., Imai, Y. Insulin resistance or insulin deficiency. Which is the primary cause of NIDDM? Diabetes 1994, 43: 735-40.
4. Sohda, T., Mizuno, K., Imamiya, E., Sugiyama, Y., Fujita, T., Kawamatsu, Y. Studies on antidiabetic agents. II. Synthesis of 5-[4-(1-methylcyclohexylmethoxy)-benzyl]thiazolidine-2,4-dione (ADD-3878) and its derivatives. Chem Pharm Bull 1982, 30: 3580-600.
5. Fujita, T., Sugiyama, Y., Taketomi, S. et al. Reduction of insulin resistance in obese and diabetic animals by 5-[4-(1-methylcyclohexyl-methoxy)-benzyl]thiazolidine-2,4-dione (ADD-3878, U-63,237, ciglitazone), a new antidiabetic agent. Diabetes 1983, 32: 804-10.
6. Hulin, B., McCarthy, P.A., Gibbs, E.M. The glitazone family of antidiabetic agents. Curr Pharm Des 1996, 2: 85-102.
7. Chang, A.Y., Wyse, B.M., Gilchrist, B.J., Peterson, T., Diani, A. R. Ciglitazone, a new hypoglycemic agent I. Studies in ob/ob mice, diabetic Chinese hamsters, and normal and streptozotocin-diabetic rats. Diabetes 1983, 32: 830-8.
8. Sohda, T., Momose, Y., Meguro, K., Kawamatsu, Y, Sugiyama, Y., Ikeda, H. Studies on antidiabetic agents. Synthesis and hypoglycemic activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidine-diones. Arzneim-Forsch/Drug Res 1990, 40: 37-42.
9. Sugiyama, Y., Taketomi, S., Shimura, Y., Ikeda, H., Fujita, T. Effects of pioglitazone on glucose and lipid metabolism in Wistar fatty rats. Arzneim-Forsch/Drug Res 1990, 40: 263-7.
10. Stevenson, R.W. Actions of novel antidiabetic agent englitazone in hyperglycemic hyperinsulinemic ob/ob mice. Diabetes 1990, 39: 1218-27.
11. Yamasaki, Y., Kawamori, R., Wasada, T. et al. Pioglitazone (AD-4833) ameliorates insulin resistance in patients with NIDDM. Tohoku J Exp Med 1997, 183: 173-83.
12. Oakes, N.D., Kennedy, C.J., Jenkins, A.B., Laybutt, D.R., Chisholm, D.J., Kraegen, E.W. A new antidiabetic agent, BRL 49653, reduces lipid availability and improves insulin action and glucoregulation in the rat. Diabetes 1994, 43: 1203-10.
13. Suter, S.L., Nolan, J.J., Wallace, P., Gumbiner, B., Olefsky, J.M. Metabolic effects of new oral hypoglycemic agent CS-045 in NIDDM subjects. Diabetes Care 1992, 15: 193-203.
14. Oginara, T., Rakugi, H., Ikegami, H., Mikami, H., Masuo, K., Enhancement of insulin sensitivity by troglitazone lowers blood pressure in diabetic hypertensives. Am J Hypertens 1995, 8: 316-20.
15. Iwamoto, Y., Kosaka, K., Kuzuya, T., Akanuma, Y., Shigeta, Y., Kaneko, T. Effects of troglitazone: A new hypoglycemic agent in patients with NIDDM poorly controlled by diet therapy. Diabetes Care 1996, 19: 151-6.
16. Iwamoto, Y., Kuzuya, T., Matsuda, A. et al. Effect of new oral antidiabetic agent CS-045 on glucose tolerance and insulin secretion in patients with NIDDM. Diabetes Care 1991, 14: 1083-6.
17. Nolan, J.J., Ludvik, B., Beerdsen, P., Joyce, M., Olefsky, J. Improvement in glucose tolerance and insulin resistance in obese subjects treated with troglitazone. N Engl J Med 1994, 331: 1188-93.
18. Antonucci, T., Whitcomb, R., McLain, R., Lockwood, D. Impaired glucose tolerance is normalized by treatment with the thiazolidinedione troglitazone. Diabetes Care 1997, 20: 188-93.
19. Ghazzi, M.N., Perez, J.E., Antonucci, T.K., Driscoll, J.H., Huang, S.M., Faja, B.W. Cardiac and glycemic benefits of troglitazone treatment in NIDDM. Diabetes 1997, 46: 433-9.
20. Johnson, M.D., Campbell, L.K., Campbell, R.K. Troglitazone: Review and assessment of its role in the treatment of patients with impaired glucose tolerance and diabetes mellitus. Ann Pharmacother 1998, 32: 337-48.
21. Yoshioka, T., Fujita, T., Kanai, T. et al. Studies on hindered phenols and analogues. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation. J Med Chem 1989, 32: 421-8.
22. Sohda, T., Mizuno, K., Tawada, H., Sugiyama, Y., Fujita, T., Kawamatsu, Y. Studies on antidiabetic agents. I. Synthesis of 5-[4-(2-methyl-2-phenylpropoxy)-benzyl]thiazolidine-2,4-dione (AL-321) and related compounds. Chem Pharm Bull 1982, 30: 3563-73.
23. Dow, R.L., Bechle, B.M., Chou, T.T., Clark, D.A., Hulin, B., Stevenson, R.W. Benzyloxyazolidine-2,4-diones as potent hypoglycemic agents. J Med Chem 1991, 34: 1538-44.
24. Goldstein, S.W., McDermott, R.E., Gibbs, E.M., Stevenson, R.W. Hydroxyurea derivatives as hypoglycemic agents. J Med Chem 1993, 36: 2238-40.
25. Sohda, T., Mizuno, K., Momose, Y., Ikeda, H., Fujita, T., Meguro, K. Studies on antidiabetic agents. 11. Novel thiazolidinedione derivatives as potent hypoglycemic and hypolipidemic agents. J Med Chem 1992, 35: 2617-26.
26. Hulin, B., Newton, L.S., Lewis, D.M., Generux, P.E., Gibbs, E.M., Clark, D.A. Hypoglycemic activity of a series of alpha-alkylthio and α-alkoxy carboxylic acids related to ciglitazone. J Med Chem 1996, 39: 3897-907.
27. Buckle, D.R., Cantello, B.C.C., Cawthorne, M.A. et al. Non thiazolidinedione antihyperglycemic agents. 1: α-Heteroatom substituted β-phenylpropanoic acids. Bioorg Med Chem Lett 1996, 6: 2121-6.
28. Ishikawa, Y., Watanabe, K., Takeno, H., Tani, T. Effects of the novel oral antidiabetic agent HQL-975 on glucose and lipid metabolism in diabetic db/db mice. Arzneim-Forsch/Drug Res 1998, 48: 245.
29. Willson, T.M. et al. Substituted 4-hydroxyphenylalcanoic acid derivatives with agonist activity to PPAR-γ. WO 9731907.
30. Shinkai, H., Onogi, S., Tanaka, M. et al. Isoxazolidine-3,5-dione and noncyclic 1,3-dicarbonyl compounds as hypoglycemic agents. J Med Chem 1998, 41: 1927-33.
31. Zask, A., Jirkovsky, I., Nowicki, J.W., McCaleb, M.L. Synthesis and antihyperglycemic activity of novel 5-(naphthalenylsulfonyl)-2,4-thiazolidinediones. J Med Chem 1990, 33: 1418-23.
32. Zvilichovsky, G. Disic acids. A study of a new series of strong organic acids and their condensation products with aldehydes. Tetrahedron 1975, 31: 1861-7.
33. Kletzien, R.F., Clarke, S.D., Ulrich, R.G. Enhancement of adipocyte differentiation by an insulin-sensitizing agent. Mol Pharmacol 1991, 41: 393-8.
34. Shibata, T., Matsui, K., Nagao, K., Shinkai, H., Yonemori, F., Wakitani, K. Pharmacological profiles of a novel antidiabetic agent, JTT-501, an isoxazolidinedione derivative. Eur J Pharmacol 1999, 364: 211-9.
35. Iwatsuka, H., Shino, A., Suzuoki, Z. General survey of diabetic features of yellow KK mice. Endocrinol Jpn 1970, 17: 23-35.
36. Lehmann, J.M., Moore, L.B., Smith-Oliver, T.A., Wilkison, W.O., Willson, T.M., Kliewer, S.A. An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor γ (PPAR γ). J Biol Chem 1995, 270: 12953-6.
37. Willson, T.M., Cobb, J.E., Cowan, D.J. et al. The structure-activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem 1996, 39: 665-8.
38. Miles, P.D.G., Higo, K., Romeo, O.M., Lee, M-K., Rafaat, K., Olefsky, J.M. Troglitazone prevents hyperglycemia-induced but not glucosamine-induced insulin resistance. Diabetes 1998, 47: 395-400.