From libraries to candidate: The discovery of new ultra long-acting dibasic β 2-adrenoceptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 1, 2012, Pages 689-695

  Alcaraz, Lilian ^a   Bailey, Andrew ^a   Cadogan, Elaine ^a   Connolly, Stephen ^a   Jewell, Robert ^a   Jordan, Stephen ^a   Kindon, Nicholas ^a   Lister, Andrew ^a   Lawson, Mandy ^a   Mullen, Alexander ^a   Dainty, Ian ^a   Nicholls, David ^a   Paine, Stuart ^a   Pairaudeau, Garry ^a   Stocks, Michael J ^a   Thorne, Phillip ^a   Young, Alan ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

2 Agonist; Adrenoceptor agonist; Asthma; COPD; Duration; Inhaled; LABA

Indexed keywords

BETA 2 ADRENERGIC RECEPTOR STIMULATING AGENT; FORMOTEROL; INDACATEROL; METHACHOLINE; SALMETEROL; SIBENADET;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DESIGN; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG HALF LIFE; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG TARGETING; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MAXIMUM PLASMA CONCENTRATION; MOLECULAR LIBRARY; MOLECULE; NONHUMAN; PHARMACODYNAMICS; PHARMACOLOGICAL PARAMETERS; PHYSICAL CHEMISTRY; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION;

ADRENERGIC BETA-AGONISTS; ANIMALS; ASTHMA; BRONCHODILATOR AGENTS; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; CYCLIC AMP; DRUG DESIGN; GUINEA PIGS; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; PROTEIN BINDING; PULMONARY DISEASE, CHRONIC OBSTRUCTIVE; THIAZOLES; TIME FACTORS;

EID: 84655167811     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.10.049     Document Type: Article

References (41)

1. B. Waldeck Eur. J. Pharmacol. 445 2002 1
2. N.M. Siafakas, P. Vermeire, and N.B. Price Eur. Respir. J. 8 1995 1398
3. P.M. Calverley, R. Pauwels, J. Vestbo, P. Jones, N. Pride, A. Gulsvik, J. Anderson, and C. Maden Lancet 361 2003 449
4. W. Szafranski, A. Cukier, A. Ramirez, G. Menga, R. Sansores, S. Nahabedian, S. Peterson, and H. Olsson Eur. Resp. J. 21 2003 74
5. W. MacNee, R. ZuWallack, and J. Keenan Clinical Management of Chronic Obstructive Pulmonary Disease 2nd ed. 2007 Professional Communications New York
6. M. Cazzola, A. Segreti, and M.G. Matera Curr. Opin. Pulm. Med. 16 2010 6
7. R. Dahl, L.A. Greefhorst, D. Nowak, V. Nonikov, A.M. Byrne, M.H. Thomson, D. Till, and G. Della Cioppa Am. J. Respir. Crit. Care Med. 164 2001 778
8. H. Matthys Respiration 68 2001 432
9. S.I. Rennard, W. Anderson, R. ZuWallack, J. Broughton, W. Bailey, M. Friedman, M. Wisniewski, and K. Rickard Am. J. Respir. Crit. Care Med. 163 2001 1087
10. D.A. Mahler, J.F. Donohue, R.A. Barbee, M. Goldman, N.J. Gross, M.E. Wisniewski, S.W. Yancey, B.A. Zakes, K.A. Rickard, and W.H. Anderson Chest 115 1999 957
11. M.G. Matera, M. Cazzola, A. Vinciguerra, F. Di Perna, F. Calderaro, M. Caputi, and F. Rossi Pulm. Pharmacol. 8 1995 267
12. For recent reviews see: T.T. Hansel, and P.J. Barnes Prog. Resp. Res. 39 2010 3
13. P.A. Glossop, and D.A. Price Annu. Rep. Med. Chem. 41 2006 237
14. For a recent review see: B.C. Moulton, and A.D. Fryer Br. J. Pharmacol. 163 2011 44
15. M. Cazzola, L. Calzetta, and M.G. Matera Br. J. Pharmacol. 163 2011 4
16. C.K. Hui, and K.F. Chung Exp. Rev. Respir. Med. 5 2011 9
17. R. Dahl, K.F. Chung, R. Buhl, H. Magnussen, V. Nonikov, D. Jack, P. Bleasdale, R. Owen, M. Higgins, and B. Kramer Thorax 65 2010 473
18. J.F. Donohue, C. Fogarty, J. Lötvall, D.A. Mahler, H. Worth, A. Yorgancioglu, A. Iqbal, J. Swales, R. Owen, M. Higgins, and B. Kramer Am. J. Respir. Crit. Care Med. 182 2010 155 162
19. F. Baur, D. Beattie, D. Beer, D. Bentley, M. Bradley, I. Bruce, S.J. Charlton, B. Cuenoud, R. Ernst, R.A. Fairhurst, B. Faller, D. Farr, T. Keller, J.R. Fozard, J. Fullerton, S. Garman, J. Hatto, C. Hayden, H. He, C. Howes, D. Janus, Z. Jiang, C. Lewis, F. Loeuillet-Ritzler, H. Moser, J. Reilly, A. Steward, D. Sykes, L. Tedaldi, A. Trifilieff, M. Tweed, S. Watson, E. Wissler, and D. Wyss J. Med. Chem. 53 2010 3675
20. For some recent examples see: D. Pérez, M. Crespo, L. Solé, M. Prat, C. Carcasona, E. Calama, R. Otal, A. Gavaldá, M. Gómez-Angelats, M. Miralpeix, and C. Puig Bioorg. Med. Chem. Lett. 21 2011 1545
21. D. Beattie, M. Bradley, A. Brearley, S.J. Charlton, B.M. Cuenoud, R.A. Fairhurst, P. Gedeck, M. Gosling, D. Janus, D. Jones, C. Lewis, C. McCarthy, H. Oakman, R. Stringer, R.J. Taylor, and A. Tuffnell Bioorg. Med. Chem. Lett. 20 2010 5302
22. P.A. Glossop, C.A. Lane, D.A. Price, M.E. Bunnage, R.A. Lewthwaite, K. James, A.D. Brown, M. Yeadon, C. Perros-Huguet, M.A. Trevethick, N.P. Clarke, R. Webster, R.M. Jones, J.L. Burrows, N. Feeder, S.C. Taylor, and F.J. Spence J. Med. Chem. 53 2010 6640
23. T. Bouyssou, C. Hoenke, R. Christoph, Klaus, P. Lustenberger, S. Pestel, P. Sieger, R. Lotz, C. Heine, F.H. Buettner, A. Schnapp, and I. Konetzki Bioorg. Med. Chem. Lett. 20 2010 1410
24. C. Hoenke, T. Bouyssou, C.S. Tautermann, K. Rudolf, A. Schnapp, and I. Konetzki Bioorg. Med. Chem. Lett. 19 2009 6640
25. T. Bouyssou, K. Rudolf, C. Hoenke, P. Lustenberger, A. Schnapp, and I. Konetzki Bioorg. Med. Chem. Lett. 19 2009 5237
26. P.A. Procopiou, V.J. Barrett, N.J. Bevan, K. Biggadike, P.R. Butchers, D.M. Coe, R. Conroy, D.D. Edney, R.N. Field, A.J. Ford, S.B. Guntrip, B.E. Looker, I.M. McLay, M.J. Monteith, V.S. Morrison, P.J. Mutch, S.A. Richards, R. Sasse, and C.E. Smith J. Med. Chem. 52 2009 2280
27. A.D. Brown, M.E. Bunnage, P.A. Glossop, K. James, R. Jones, C.A.L. Lane, R.A. Lewthwaite, S. Mantell, C. Perros-Huguet, D.A. Price, M. Trevethick, and R. Webster Bioorg. Med. Chem. Lett. 18 2008 1280
28. A.D. Brown, M.E. Bunnage, P.A. Glossop, M. Holbrook, R.D. Jones, C.A.L. Lane, R.A. Lewthwaite, S. Mantell, C. Perros-Huguet, D.A. Price, and R. Webster Bioorg. Med. Chem. Lett. 17 2007 6188
29. A.D. Brown, M.E. Bunnage, P.A. Glossop, K. James, R. Jones, C.A.L. Lane, R.A. Lewthwaite, S. Mantell, C. Perros-Huguet, D.A. Price, M. Trevethick, and R. Webster Bioorg. Med. Chem. Lett. 17 2007 4012
30. Alcaraz, L.; Lister, A.; Pairaudeau, G. WO2007106016, 2007.
31. M.J. Stocks, L. Alcaraz, A. Bailey, R. Bonnert, E. Cadogan, J. Christie, S. Connolly, A.R. Cook, A.J. Fisher, A. Flaherty, S. Hill, A. Humphries, A.H. Ingall, S. Jordan, M. Lawson, A. Mullen, D. Nicholls, S. Paine, G. Pairaudeau, S. St-Gallay, and A. Young Bioorg. Med. Chem. Lett. 21 2011 4027
32. S. Connolly, L. Alcaraz, A. Bailey, E. Cadogan, J. Christie, A.R. Cook, A.J. Fisher, S. Hill, A. Humphries, A.H. Ingall, Z. Kane, S. Paine, G. Pairaudeau, M.J. Stocks, and A. Young Bioorg. Med. Chem. Lett. 21 2011 4612
33. R.P. Austin, P. Barton, R.V. Bonnert, R.C. Brown, P.A. Cage, D.R. Cheshire, A.M. Davis, I.G. Dougall, F. Ince, G. Pairaudeau, and A. Young J. Med. Chem. 46 2003 3210
34. Z.R. Tayab, and G. Hochhaus Expert Opin. Drug Deliv. 2 2005 519
35. Another series of compound based on a hydroxyl benzothiazolone head group was also recently disclosed in the literature: see Ref. 12b.
36. M.C. Wenlock, P. Barton, T. Potter, and R.P. Austin J. Biomol. Screen. 16 2011 348
37. A. Walland, R. Palluk, S. Burkard, and R. Hammer Eur.J. Pharmacol. 330 1997 213
38. Alcaraz, L.; Cadogan, E. B.; Connolly, S.; Nicholls, D. J.; Young, A. WO2009037503, 2009.
39. H.B. Hass, and M.L. Bender J. Am. Chem. Soc. 71 1949 1767
40. F. Gigante, M. Kaiser, R. Brun, and I.H. Gilbert Bioorg. Med. Chem. 18 2010 7291
41. R.A. Fernandes, and P. Kumar Tetrahedron Lett. 44 2003 1275