Identification of YH-GKA, a novel benzamide glucokinase activator as therapeutic candidate for type 2 diabetes mellitus

Archives of Pharmacal Research

Volumn 35, Issue 12, 2012, Pages 2029-2033

  Park, Kaapjoo ^a  

^a Yuhan Research Institute   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; ENZYME ACTIVATOR; GLUCOSE; INSULIN; METFORMIN; UNCLASSIFIED DRUG; YH GKA;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME ASSAY; GLUCOSE BLOOD LEVEL; HYDROGEN BOND; IN VITRO STUDY; INSULIN RELEASE; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; ORAL GLUCOSE TOLERANCE TEST;

ANIMALS; BENZAMIDES; DIABETES MELLITUS, TYPE 2; ENZYME ACTIVATORS; GLUCOKINASE; HUMANS; HYPOGLYCEMIC AGENTS; PYRIDINES;

EID: 84875737974     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-012-1201-9     Document Type: Article

References (21)

1. Bebernitz, G. R.; Beaulieu, V.; Dale, B. A.; Deacon, R.; Duttaroy, A.; Gao, J.; Grondine, M. S.; Gupta, R. C.; Kakmak, M.; Kavana, M.; Kirman, L. C.; Liang, J.; Maniara, W. M.; Munshi, S.; Nadkarni, S. S.; Schuster, H. F.; Stams, T.; St Denny, I.; Taslimi, P. M.; Vash, B.; and Caplan, S. L.; Investigation of functionally liver selective glucokinase activators for the treatment of type 2 diabetes. J. Med. Chem.; 52, 6142-6152 (2009).
2. Fowler, M. J.; Microvascular and macrovascular complications of diabetes. Clin. Diabetes, 26, 77-82 (2008). (Pubitemid 351556223)
3. Fyfe, M. C. T. and Procter, M. J.; Glucokinase activators as potential antidiabetic drugs possessing superior glucoselowering efficacy. Drugs Future, 34, 641-653 (2009).
4. Grimsby, J.; Sarabu, R.; Corbett, W. L.; Hayne, N. E.; Bizzarro, F. T.; Coffey, J. W.; Guertin, K. R.; Hilliard, D. W.; Kester, R. F.; Mahaney, P. E.; Marcus, L.; Qi, L.D.; Soence, C. L.; Tengi, J.; Magnuson, M. A.; Chu, C. A.; Dvorozniak, M. T.; Matschinsky, F. M.; and Grippo, J. F.; Allosteric activators of glucokinase: potential role in diabetes therapy. Science, 301, 370-373 (2003). (Pubitemid 36877072)
5. Heredia W.; Thomson J.; Nettleton D.; and Sun S.; Glucoseinduced conformational changes in glucokinase mediate allosteric regulation: transient kinetic analysis. Biochemistry, 45, 7553-7562 (2006). (Pubitemid 43894948)
6. Iino, T.; Hashimoto, N.; Hasegawa, T.; Chiba, M.; Eiki, J.; and Nishimura, T.; Metabolic activation of N-thiazol-2-yl benzamide as glucokinase activators: Impacts of glutathione trapping on covalent binding. Bioorg. Med. Chem. Lett.; 20, 1619-1622 (2010).
7. Kahn, S. E.; Hull, R. L.; and Utzschneider, K. M.; Mechanisms linking obesity to insulin resistance and type 2 diabetes. Nature, 444, 840-846 (2006). (Pubitemid 46024990)
8. Lebovitz, H. E.; Management of hyperglycemia with oral antihyperglycemic agents in type 2 diabetes. In Joslin's Diabetes Mellitus 14th ed. Lippincott Williams & Wilkins, Philadelphia, PA, pp. 687-710, (2005).
9. Massa, M. L.; Gagliardino, J. J.; and Francini, F.; Liver Glucokinase: An overview on the regulatory mechanisms of its activity. IUBMB Life, 63, 1-6 (2011).
10. Matschinsky, F. M.; A lesson in metabolic regulation inspired by the glucokinase glucose sensor paradigm. Diabetes, 45, 223-241 (1996). (Pubitemid 26045806)
11. Matschinsky, F. M.; Glaser, B.; and Magnuson, M. A.; Pancreatic beta-cell glucokinase: closing the gap between theoretical concepts and experimental realities. Diabetes, 47, 307-315 (1998). (Pubitemid 28104189)
12. Matschinsky, F.; Assessing the potential of glucokinase activatorsin diabetic therapy. Nat. Rev. Drug Discov.; 8, 399-416 (2009).
13. Meininger, G. E.; Scott, R.; Alba, R.; Shentu, Y.; Luo, E.; Amin, H.; Davies, M. J.; Kaufman, K. D.; and Goldstein, B. J.; Effects of MK-0941, a novel glucokinase activator, on glycemic control in insulin-treated patients with type 2 diabetes. Diabetes Care, 34, 2560-2566 (2011).
14. Mitsuya, M.; Kamata, K.; Bamba, M.; Watanabe, H.; Sasaki, Y.; Sasaki, K.; Ohyama, S.; Hosaka, H.; Nagata, Y.; Eiki, J.; and Nishimura, T.; Discovery of novel 3,6-disubstituted 2-pyridinecarboxamide derivatives as GK activators. Bioorg Med Chem Lett.; 19, 2718-2721 (2009).
15. Pfefferkorn, J. A.; Guzman-Perez, A.; Litchfield, J.; Aiello, R.; Treadway, J. L.; Pettersen, J.; Minich, M. L.; Filipski, K. J.; Jones, C. S.; Tu, M.; Aspnes, G.; Risley, H.; Bian, J.; Stevens, B. D.; Bourassa, P.; D'Aquila, T.; Baker, L.; Barucci, N.; Robertson, A. S.; Bourbonais, F.; Derksen, D. R.; Macdougall, M.; Cabrera, O.; Chen, J.; Lapworth, A. L.; Landro, J. A.; Zavadoski, W. J.; Atkinson, K.; Haddish-Berhane, N.; Tan, B.; Yao, L.; Kosa, R. E.; Varma, M. V.; Feng, B.; Duignan, D. B.; El-Kattan, A.; Murdande, S.; Liu, S.; Ammirati, M.; Knafels, J.; Dasilva-Jardine, P.; Sweet, L.; Liras, S.; and Rolph, T. P.; Discovery of (S)-6-(3-cyclopentyl-2-(4-(trifluoromethyl)-1H- imidazol-1-yl)propanamido) nicotinic acid as a hepatoselective glucokinase activator clinical candidate for treating type 2 diabetes mellitus. J. Med. Chem.; 55, 1318-1333 (2012).
16. Pike, K. G.; Allen, J. V.; Caulkett, P. W.; Clarke, D. S.; Donald, C. S.; Fenwick, M. L.; Johnson, K. M.; Johnstone, C.; McKerrecher, D.; Rayner, J. W.; Walker, R. P.; and Wilson, I.; Design of a potent, soluble glucokinase activator with increased pharmacokinetic half-life. Bioorg. Med. Chem. Lett.; 11, 3467-3470 (2011).
17. Sarabu, R.; Tilley, J. W.; and Grimsby, J.; The discovery of piragliatin, a glucokinase activator. RSC Drug Discovery Series, 4, 51-70 (2011).
18. Sidduri, A.; Grimsby, J. S.; Corbett, W. L.; Sarabu, R.; Grippo, J. F.; Lou, J.; Kester, R. F.; Dvorozniak, M.; Marcus, L.; Spence, C.; Racha, J. K.; and Moore, D. J.; 2,3-Disubstituted acrylamides as potent glucokinase activators. Bioorg. Med. Chem. Lett.; 20, 5673-5676 (2010).
19. Waring, M. J.; Johnstone, C.; McKerrecher, D.; Pike, K. G.; and Robb, G.; Matrix-based multiparameter optimisation of glucokinase activators: the discovery of AZD1092. Med. Chem. Commun. 2, 775-779 (2011).
20. Winzell, M. S.; Coghlan, M.; Leighton, B.; Frangioudakis, G.; Smith, D. M.; Storlien, L. H.; and Ahrén, B.; Chronic glucokinase activation reduces glycaemia and improves glucose tolerance in high-fat diet fed mice. Eur. J. Pharmacol.; 663, 80-86 (2011).
21. Yi, W-H.; Han, T-D.; Lee, K-Y.; Kim, Y-H.; Jung, E-H.; Lee, DH.; Park, Y-H.; Min, K-N.; Kim, J-K.; and Lee, B-K.; Novel glucokinase activators and processes for the preparation thereof. WO 2011/081280 A2 (2011).