Discovery of an orally bioavailable alkyl oxadiazole β3 adrenergic receptor agonist

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 13, 2000, Pages 1427-1429

  Feng, Danqing D ^a   Biftu, Tesfaye ^a   Candelore, Mari R ^a   Cascieri, Margaret A ^a   Colwell, Lawrence F ^a   Deng, Liping ^a   Feeney, William P ^a   Forrest, Michael J ^a   Hom, Gary J ^a   MacIntyre, D Euan ^a   Miller, Randall R ^a   Stearns, Ralph A ^a   Strader, Catherine D ^a   Tota, Laurie ^a   Wyvratt, Matthew J ^a   Fisher, Michael H ^a   Weber, Ann E ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONAMIDE DERIVATIVE; BETA 3 ADRENERGIC RECEPTOR BLOCKING AGENT; OXADIAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL MODIFICATION; DOG; DRUG BIOAVAILABILITY; DRUG SYNTHESIS; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ADRENERGIC BETA-AGONISTS; ANIMALS; BIOLOGICAL AVAILABILITY; CHO CELLS; CRICETINAE; DOGS; DRUG DESIGN; HUMANS; MOLECULAR STRUCTURE; OXADIAZOLES; RATS; RECEPTORS, ADRENERGIC, BETA-3; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; CANIS FAMILIARIS;

EID: 0034601223     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00267-5     Document Type: Article

References (19)

1. For recent reviews see: (a) Weber, A. E. Annu. Rep. Med. Chem. 1998, 33, 193; Lowell, B. B.; Flier, J. S. Annu. Rev. Med. 1997, 48, 307.
2. For recent reviews see: (a) Weber, A. E. Annu. Rep. Med. Chem. 1998, 33, 193; Lowell, B. B.; Flier, J. S. Annu. Rev. Med. 1997, 48, 307.
3. (b) Arch, J. R. S.; Wilson, S. Int. J. Obesity 1996, 20, 191.
4. (c) Himms-Hagen, J.; Danforth, E. Curr. Opin. Endocrin. Diabetes 1996, 3, 59.
5. (d) Claus, T. H.; Bloom, J. D. Annu. Rep. Med. Chem. 1995, 30, 189.
6. (e) Howe, R. Drugs Fut. 1993, 18, 529.
7. (f) Arch, J. R. S.; Kaumann, A. J. Med. Res. Rev. 1993, 13, 663.
8. (a) Weber, A. E.; Mathvink, R. J.; Perkins, L.; Hutchins, J. E.; Candelore, M. R.; Tota, L; Strader, C. D.; Wyvratt, M. J.; Fisher, M. H. Bioorg. Med. Chem. Lett. 1998, 8, 1101.
9. (b) Parmee, E. R.; Naylor, E. M.; Perkins, L.; Colandrea, V. J.; Ok, H. O.; Candelore, M. R.; Cascieri, M. A.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Miller, R. R.; Stearns, R. A.; Tota, L; Strader, C. D.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Bioorg. Med. Chem. Lett. 1999, 9, 749.
10. (c) Naylor, E. M.; Colandrea, V. J.; Candelore, M. R.; Cascieri, M. A.; Colwell, L. F.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Strader, C. D.; Tota, L; Wang, P.-R.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Bioorg. Med. Chem. Lett. 1998, 8, 3087.
11. (d) Shih, T. L.; Candelore, M. R.; Cascieri, M. A.; Chiu, S. L.; Colwell, L. F.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Miller, R. R.; Stearns, R. A.; Strader, C. D.; Tota, L.; Wyvratt, M. J.; Fisher, M. H.; Weber, A. E. Bioorg. Med. Chem. Lett. 1999, 9, 1251.
12. (e) Mathvink, R. J.; Barritta, A. M.; Deng, L.; Candelore, M. R.; Tota, L; Strader, C. D.; Wyvratt, M. J.; Fisher, M. H. Bioorg. Med. Chem. Lett. 1999, 9, 1869.
13. Presented in part at the 217th National Meeting of the American Chemical Society, Anaheim, CA, March 1999; Abstract MEDI 138.
14. All final compounds were characterized by NMR, mass spectrometry, and HPLC. For experimental details see: Fisher, M. H.; Naylor, E. M; Ok, D.; Weber, A. E.; Shih, T.; Ok, H. U.S. Patent 5 561 142, 1996; Chem. Abstr. 1996, 125, 275666.
15. All final compounds were characterized by NMR, mass spectrometry, and HPLC. For experimental details see: Fisher, M. H.; Naylor, E. M; Ok, D.; Weber, A. E.; Shih, T.; Ok, H. U.S. Patent 5 561 142, 1996; Chem. Abstr. 1996, 125, 275666.
16. Liang G., Feng D.D. Tetrahedron Lett. 37:1996;6627.
17. Granneman J.G., Lahners K.N., Rao D.D. Mol. Pharmacol. 42:1992;964.
18. Fisher M.H., Amend A.M., Bach T.J., Barker J.M., Brady E.J., Candelore M.R., Carroll D., Cascieri M.A., Chiu S.-H.L., Deng L., Forrest M.J., Hegarty-Friscino B., Guan X.-M., Hom G.J., Hutchins J.E., Kelly L.J., Mathvink R.J., Metzger J.M., Miller R.R., Ok H.O., Parmee E.R., Saperstein R., Strader C.D., Stearns R.A., Thompson G.M., Tota L., Vicario P.P., Weber A.E., Woods J.W., Wyvratt M.J., Zafian P.T., MacIntyre D.E. J. Clin. Invest. 101:1998;2387.
19. For experimental details see ref 7.