Discovery of new chemotype dipeptidyl peptidase IV inhibitors having (R)-3-amino-3-methyl piperidine as a pharmacophore

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 24, 2010, Pages 7246-7249

  Nishio, Yukihiro ^a   Kimura, Hidenori ^a   Tosaki, Shinya ^a   Sugaru, Eiji ^a   Sakai, Mutsuko ^a   Horiguchi, Masakuni ^a   Masui, Yumi ^a   Ono, Michiko ^a   Nakagawa, Tsutomu ^a   Nakahira, Hiroyuki ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

(R) 3 Amino 3 methyl piperidine; 3 Amino piperidine; Dipeptidyl peptidase 4; Dipeptidyl peptidase 4 inhibitors; DPP 4; DPP 4 inhibitors

Indexed keywords

DIPEPTIDYL PEPTIDASE IV INHIBITOR;

ANIMAL EXPERIMENT; ARTICLE; BIOAVAILABILITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; NONHUMAN; PHARMACOPHORE; RAT;

ANIMALS; DIPEPTIDYL PEPTIDASE 4; DIPEPTIDYL-PEPTIDASE IV INHIBITORS; DRUG EVALUATION, PRECLINICAL; HUMANS; MICROSOMES, LIVER; PIPERIDINES; PYRIMIDINONES; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 78449276647     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.10.101     Document Type: Article

References (21)

1. For recent reviews see S.H. Havale, and M. Pal Bioorg. Med. Chem. 17 2009 1783
2. H.-J. Mest, and R. Mentlein Diabetlogia 48 2005 616
3. A.E. Weber J. Med. Chem. 47 2004 4135
4. K. Augustyns, P. Van der Veken, K. Senten, and A. Haemers Expert Opin. Ther. Patents 13 2003 499
5. For recent references see J.J. Holst Curr. Opin. Endocrin. Diabetes 48 2005 616
6. L.B. Knudsen J. Med. Chem. 47 2004 4128
7. L. Farilla, H. Hui, C. Bertolotto, E. Kang, A. Bulotta, U. Di Mario, and R. Perfetti Endocrinology 143 2002 4397
8. D. Kim, L. Wamg, M. Beconi, G.J. Eiermann, M.H. Fisher, H. He, G.J. Hickey, J.E. Kowalchick, B. Leiting, K. Lyons, F. Marsilio, M.E. McCann, R.A. Patel, A. Petrowv, G. Scapin, S.B. Patel, R. SinhaRoy, J.K. Wu, M.J. Wyvratt, B.B. Zhang, L. Zhu, N.A. Thornberry, and A.E. Weber J. Med. Chem. 48 2005 141
9. E.B. Villhauer, J.A. Brinkman, G.B. Naderi, B.F. Burkey, B.E. Dunning, K. Prasad, B.L. Mangold, M.E. Russell, and T.E. Hughes J. Med. Chem. 46 2003 2774
10. Gwaltney, S. L.; Aertgeerts, K.; Feng, J.; Kaldor, S. W.; Kassel, D. B.; Manuel, M.; Navre, M.; Prasad, G. S.; Shi, L.; Skene, R. J.; Stafford, J. A.; Wallace, M.; Wu, R.; Ye, S.; Zhang, Z. Abstracts of Papers, 231st, Meeting of the American Chemical Society, Atlanta, GA, 2006; American Chemical Society: Washington, DC, 2006; MEDI-018.
11. J. Feng, Z. Zhang, M.B. Wallace, J.A. Sttaford, S.W. Kaldor, D.B. Kassel, M. Navre, L. Shi, R.J. Skene, T. Asakawa, K. Takeuchi, R. Xu, D.R. Webb, and S.L. Gwaltney J. Med. Chem. 50 2007 2297
12. M. Eckhardt, E. Langkopf, M. Mark, M. Tadayyon, L. Thomas, H. Nar, W. Pfrengle, B. Guth, R. Lotz, P. Sieger, H. Fuchs, and F. Himmerlsbach J. Med. Chem. 50 2007 6450
13. Nakahira, H.; Kimura, H.; Hochigai, H. WO2006068163, 2006.
14. Castro Pineiro, J. L.; Rubo, P. A.; Swain, C. J. WO 2002057250, 2002.
15. T.D. Nelson, J.D. Rosen, J.H. Smitrovich, J. Payack, B. Craig, L. Matty, M.A. Huffman, and J. Mcnamara Org. Lett. 7 2005 55
16. C.A. Abbot, D.M. Yu, E. Woollatt, G.R. Sutherland, G.W. McCaughen, and M.D. Gorrell Eur. J. Biochem. 267 2000 6140
17. C. Olsen, and N. Wagtmann Gene 299 2002 185
18. G.R. Lankas, B. Leiting, R. Sinha Roy, G.J. Eiermann, M.G. Beconi, T. Biftu, C.-C. Chan, S. Edmondson, W.P. Feeney, H. He, D.E. Ippolito, D. Kim, K.A. Lyons, H.O. Ok, R.A. Patel, A.N. Petrov, K.A. Pryor, X. Qian, L. Reigle, A. Woods, J.K. Wu, D. Zaller, X. Zhang, L. Zhu, A.E. Weber, and N.A. Thronberry Diabetes 54 2005 2988
19. B.F. Burkey, P.K. Hoffmann, U. Hassiepen, J. Trappe, M. Juedes, and J.E. Foley Diabetes Obes. Metab. 10 2008 1057
20. J.-J. Wu, H.-K. Tang, T.-K. Yeh, C.-M. Chen, H.-C. Shy, Y.-R. Chu, C.-H. Chien, T.-Y. Tsai, Y.-C. Huang, Y.-L. Huang, C.-H. Huang, H.-Y. Tseng, W.-T. Jiaang, Y.-S. Chao, and X. Chen Biochem. Pharmacol. 78 2009 203
21. 2O: C, 55.40; H, 6.76; N, 14.68. Found: C, 55.53; H, 6.59; N, 14.59.