Steroidal C-21 mercapto derivatives as dissociated steroids: Discovery of an inhaled dissociated steroid

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 21, 2011, Pages 6343-6347

  Biju, Purakkattle ^a   McCormick, Kevin ^a   Aslanian, Robert ^a   Berlin, Michael ^a   Solomon, Daniel ^a   Chapman, Richard ^a   McLeod, Robbie ^a   Prelusky, Daniel ^a   Eckel, Stephen ^a   Kelly, George ^a   Natiello, Michelle ^a   House, Aileen ^a   Fernandez, Xiomara ^a   Bitar, Rema ^a   Phillips, Jonathan ^a   Anthes, John ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

C 21 mercapto derivatives; Dissociated steroid; Hydrocortisone; Inhaled asthma; Transactivation and transrepression

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; HYDROCORTISONE; THIOL DERIVATIVE;

ANIMAL CELL; ARTICLE; ASSAY; CONTROLLED STUDY; DISSOCIATION; DRUG DETERMINATION; DRUG EFFICACY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; LUNG FUNCTION; NONHUMAN; PNEUMONIA; RAT; SYSTEMATIC REVIEW; TRANSACTIVATION ASSAY; TRANSREPRESSION ASSAY;

RATTUS NORVEGICUS;

EID: 80054789440     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.08.108     Document Type: Article

References (38)

1. Barnes, P. J. N. Eng. J. Med. 1995, 332, 868
2. Townsend, H. B.; Saag, K. G. Clin. Exp. Rheum. 2004, 22, S77
3. Greaves, M. W.; Gatti, S. J. Dermat. Treat. 1999, 10, 83.
4. Schacke, H.; Docke, W.-D.; Asadullah, K. Pharmacol. Ther. 2002, 96, 23.
5. Brattsand, R.; Axelsson, B. I. New Drugs Asthma 1992, 2, 193
6. Axelsson, B.; Brattsand, R. Progress in Respiratory Research 2001, 31, 94 (New Drugs for Asthma, Allergy and COPD)
7. Thalen, A.; Andersson, P. H.; Andersson, P. T.; Axelsson, B.; Edsbacker, S.; Brattsand, R. Lung Biology in Health and Disease 2002, 163, 521 (Inhaled Steroids in Asthma).
8. Shapiro, E. L.; Gentles, M. J.; Tiberi, R. L.; Popper, T. L.; Berkenkopf, J.; Lutsky, B.; Watnick, A. S. J. Med. Chem. 1987, 30, 1581
9. Popper, T. L.; Gentles, M. J.; Kung, T. T.; Berkenkopf, J.; Lutsky, B. N.; Watnick, A. S.; Shapiro, E. L. J. Steroid Biochem. 1987, 27, 837.
10. Barnes, P. Clin. Sci. (London, England: 1979) 1998, 94, 557
11. Rhen, T.; Cidlowski, J. A. N. Engl. J. Med. 2005, 353, 1711
12. Ito, K.; Getting, S.; Charron, C. Scientific World J. 2006, 6, 1750.
13. Catley, M. C. The Scientific World 2007, 7 (MAR.), 421
14. Rosen, J.; Miner, J. N. Curr. Med. Chem: Immunol., Endocrine & Metabolic Agents 2002, 2, 11
15. Schacke, H.; Rehwinkel, H.; Asadullah, K. Expert Opin. Ther. Patent 2008, 18, 339;
16. Miner, J. N.; Hong, M. H.; Negro-Vilar, A. Expert Opin. Investig. Drugs 2005, 14, 1527
17. Rehwinkel, H.; Schäcke, H. Chem Med Chem 2006, 1, 803.
18. Belvisi, G.; Wicks, S. L.; Battram, C. H.; Bottoms, S. E. W.; Redford, J. E.; Woodman, P.; Brown, T. J.; Webber, S. E.; Foster, M. L. J. Immunol. 2001, 166, 1975.
19. Schaecke, H.; Asadullah, K.; Berger, M.; Rehwinkel, H. Methods and Principles in Medicinal Chemistry 2008, 39, 305 (Nuclear Receptors as Drug Targets)
20. Schacke, H.; Zollner, T. M.; Docke, W. D.; Rehwinkel, H.; Jaroch, S.; Skuballa, W.; Neuhaus, R.; May, E.; Zugel, U.; Asadullah, K. Br. J. Pharmacol. 2009, 158, 1088;
21. Schäcke, H.; Berger, M.; Rehwinkel, H.; Asadullah, K. Mol. Cell Endocrinol. 2007, 275, 109
22. Mohler, M. L.; He, Y.; Wu, Z.; Hong, S. S.; Miller, D. D. Expert Opin. Ther. Pat. 2007, 17, 37
23. Hudson, A. R.; Roach, S. L.; Higuchi, R. I.; Phillips, D. P.; Bissonnette, R. P.; Lamph, W. W.; Yen, J.; Li, Y.; Adams, M. E.; Valdez, L. J.; Vassar, A.; Cuervo, C.; Kallel, E. A.; Gharbaoui, C. J.; Mais, D. E.; Miner, J. N.; Marschke, K. B.; Rungta, D.; Negro-Vilar, A.; Zhi, L. J. Med. Chem. 2007, 50, 4699
24. Morgan, B. P.; Swick, A. G.; Hargrove, D. M.; LaFlamme, J. A.; Moynihan, M. S.; Carroll, R. S.; Martin, K. A.; Lee, E.; Decosta, D.; Bordner, J. J. Med. Chem. 2002, 45, 2417
25. Robinson, R. P.; Buckbinder, L.; Haugeto, A. I.; McNiff, P. A.; Millham, M. L.; Reese, M. R.; Schaefer, J. F.; Abramov, Y. A.; Bordner, J.; Chantigny, Y. A.; Kleinman, E. F.; Laird, E. R.; Morgan, B. P.; Murray, J. C.; Salter, E. D.; Wessel, M. D.; Yocum, S. A. J. Med. Chem. 2009, 52, 1731
26. Takahashi, H.; Bekkali, Y.; Capolino, A. J.; Gilmore, T.; Goldrick, S. E.; Nelson, R. M.; Terenzio, D.; Wang, J.; Zuvela-Jelaska, L.; Proudfoot, J.; Nabozny, G.; Thomson, D. Bioorg. Med. Chem. Lett. 2006, 16, 1549
27. Regan, J.; Lee, T. W.; Zindell, T. R. M.; Bekkali, Y.; Bentzien, J.; Gilmore, T.; Hammach, A.; Kirrane, T. M.; Kukulka, A. J.; Kuzmich, D.; Nelson, R. M.; Proudfoot, J. R.; Ralph, M.; Pelletier, J.; Souza, D.; Zuvela-Jelaska, L.; Nabozny, G.; Thomson, D. S. J. Med. Chem. 2006, 49, 7887
28. Biggadike, K.; Boudjelal, M.; Clackers, M.; Coe, D. M.; Demaine, D. A.; Hardy, G. W.; Humphreys, D.; Inglis, G. A.; Johnston, M. J.; Jones, H. T.; House, D.; Loiseau, R.; Needham, D.; Skone, P. A.; Uings, I.; Veitch, G.; Weingarten, G. G.; McLay, I. M.; Macdonald, S. J. F. J. Med. Chem. 2007, 50, 6519
29. Thompson, C. F.; Quraishi, N.; Ali, A.; Tata, J. R.; Hammond, M. L.; Balkovec, J. M.; Einstein, M.; Ge, L.; Harris, G.; Kelly, T. M.; Mazur, P.; Pandit, S.; Santoro, J.; Sitlani, A.; Wang, C.; Williamson, J.; Miller, D. K.; Yamin, T. D.; Thompson, C. M.; O'Neill, E. A.; Zaller, D.; Forrest, M. J.; Carballo-Jane, E.; Luell, S. Bioorg. Med. Chem. Lett. 2005, 15, 2163.
30. For Biological assay details, refer WO 2009085879.
31. Celly, C. S.; House, A.; Sehring, S. J.; Zhang, X. Y.; Jones, H.; Hey, J. A.; Egan, R. W.; Chapman, R. W. Eur. J. Pharmacol. 2006, 540, 147.
32. Chapman, R. W.; House, A.; Jones, H.; Richard, J.; Celly, C.; Prelusky, D.; Ting, P.; Hunter, J. C.; Lamca, J.; Phillips, J. E. Eur. J. Pharmcol. 2007, 571, 215.
33. Hoegger, P. Curr Med. Chem. Anti-Inflammatory & Anti-Allergy Agents 2003, 2, 395
34. Kelly, H. W. Ann. Allergy, Asthma Immunol. 2003, 91, 326
35. Derendorf, H.; Nave, R.; Drollmann, A.; Cerasoli, F.; Wurst, W. Eur. Respir. J. 2006, 28, 1042
36. Bodor, N.; Buchwald, P. Curr. Pharm. Des. 2006, 12, 3241
37. Johnson, M. J. Allergy Clin. Immunol. 1996, 97, 169.
38. Reichardt, H. M.; Kaestner, K. H.; Tuckermann, J.; Kretz, O.; Wessely, O.; Bock, R.; Gass, P.; Schmid, W.; Herrlich, P.; Angel, P.; Schutz, G. Cell 1998, 93, 531.