Crystalline forms of 2,2,2-trifluoro-N-[(1R,2S)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(3-methoxyphenyl)-2-propanyl]acetamide (AZD-5423)

Bibliography

• Buckbinder L, Robinson RP. The glucocorticoid receptor: molecular mechanism and new therapeutic opportunities. Curr Drug Targets Inflamm Allergy 2002;1(2):127-36
   PubMedGoogle Scholar
• Chung KF, Caramori G, Adcock IM. Inhaled corticosteroids as combination therapy with beta-adrenergic agonists in airways disease: present and future. Eur J Clin Pharmacol 2009;65(9):853-71
   PubMed Web of Science ®Google Scholar
• Barnes PJ. Glucocorticosteroids: current and future directions. Br J Pharmacol 2011;163(1):29-43
   PubMed Web of Science ®Google Scholar
• Adcock IM, Caramori G, Ito K. New insights into the molecular mechanisms of corticosteroids actions. Curr Drug Targets 2006;7(6):649-60
   PubMedGoogle Scholar
• De Bosscher K, Haegeman G, Elewaut D. Targeting inflammation using selective glucocorticoid receptor modulators. Curr Opin Pharmacol 2010;10(4):497-504
   PubMed Web of Science ®Google Scholar
• Biggadike K, Bledsoe RK, Hassell AM, et al. X-ray crystal structure of the novel enhanced-affinity glucocorticoid agonist fluticasone furoate in the glucocorticoid receptor-ligand binding domain. J Med Chem 2008;51(12):3349-52
   PubMed Web of Science ®Google Scholar
• Biggadike K, Bledsoe RK, Coe DM, et al. Design and x-ray crystal structures of high-potency nonsteroidal glucocorticoid agonists exploiting a novel binding site on the receptor. Proc Natl Acad Sci USA 2009;106(43):18114-19
   PubMedGoogle Scholar
• Diallo H, Angell DC, Barnett HA, et al. Discovery of a potent series of non-steroidal non alpha-trifluoromethyl carbinol glucocorticoid receptor agonists with reduced lipophilicity. Bioorg Med Chem Lett 2011;21(4):1126-33
   PubMedGoogle Scholar
• Kuzmich D, Kirrane T, Proudfoot J, et al. Identification of dissociated non-steroidal glucocorticoid receptor agonists. Bioorg Med Chem Lett 2007;17(18):5025-31
   PubMed Web of Science ®Google Scholar
• Norman P. Boehringer Ingleheim's selective glucocorticoid receptor agonist development candidate: evaluation of WO2010141331, WO2010141332 and WO2010141333. Expert Opin Ther Pat 2011;21(7):1137-42
   PubMed Web of Science ®Google Scholar
• Jaroch S, Berger M, Huwe C, et al. Discovery of quinolines as selective glucocorticoid receptor agonists. Bioorg Med Chem Lett 2010;20(19):5835-8
   PubMedGoogle Scholar
• Schäcke H, Zollner TM, Döcke WD, et al. Characterization of ZK 245186, a novel, selective glucocorticoid receptor agonist for the topical treatment of inflammatory skin diseases. Br J Pharmacol 2009;158(4):1088-103
   PubMed Web of Science ®Google Scholar
• Vollmer TR, Stockhausen A, Zhang JZ. Anti-inflammatory effects of mapracorat, a novel selective glucocorticoid receptor agonist, is partially mediated by MAP kinase phosphatase-1 (MKP-1). J Biol Chem 2012;287(42):35212-21
   PubMedGoogle Scholar
• Weinstein DS, Gong H, Doweyko AM, et al. Azaxanthene based selective glucocorticoid receptor modulators: design, synthesis, and pharmacological evaluation of (S)-4-(5-(1-((1,3,4-thiadiazol-2-yl)amino)-2-methyl-1-oxopropan-2-yl)-5H-chromeno[2,3-b]pyridin-2-yl)-2-fluoro-N,N-dimethylbenzamide (BMS-776532) and its methylene homologue (BMS-791826). J Med Chem 2011;54(20):7318-33
   PubMedGoogle Scholar
• van Lierop MJ, Alkema W, Laskewitz AJ, et al. Org 214007-0: a novel non-steroidal selective glucocorticoid receptor modulator with full anti-inflammatory properties and improved therapeutic index. PLoS One 2012;7(11):e48385
   PubMed Web of Science ®Google Scholar
• Stock T, Fleishaker D, Mukherjee A, et al. Evaluation of Safety, Pharmacokinetics and Pharmacodynamics of a Selective Glucocorticoid Receptor Modulator (SGRM) in Healthy Volunteers [abstract]. Arthritis Rheum 2009;60(Suppl 10):420
   Google Scholar
• Pfizer Products, Inc. Tricyclic compounds and their use as glucocorticoid receptor modulators. WO2008093227; 2008
   Google Scholar
• Schering AG. Nonsteroidal antiinflammatories. WO0032584; 2000
   Google Scholar
• AstraZeneca AB. Novel sulphonamide derivatives as glucocorticoid receptor modulators for the treatment of inflammatory diseases. WO2006046916; 2006
   Google Scholar
• Drahl C. AZD5423, for chronic obstructive pulmonary disease. Chem Eng News 2013;91(16):14-15
   Google Scholar
• Astra Zeneca AB, Bayer Schering Pharma AG. Indazolyl ester and amide derivatives for the treatment of glucocorticoid receptor mediated disorders. WO2008076048; 2008
   Google Scholar
• Giembycz MA, Kaur M, Leigh R, Newton R. A Holy Grail of asthma management: toward understanding how long-acting beta(2)-adrenoceptor agonists enhance the clinical efficacy of inhaled corticosteroids. Br J Pharmacol 2008;153(6):1090-104
   PubMed Web of Science ®Google Scholar
• AstraZeneca AB, Bayer Schering Pharma AG. Combination of (a) glucocorticoid receptor modulator and (b) a b2-agonist. WO2009142568; 2009
   Google Scholar
• AstraZeneca AB. A combination of (a) glucocorticoid receptor modulator and (b) a muscarinic antagonist. WO2010008341; 2010
   Google Scholar
• AstraZeneca AB, Bayer Pharma AG. Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases. WO2011061527; 2011
   Google Scholar
• AstraZeneca AB. Crystalline form of indazolyl amide derivatives for the treatment glucocorticoid receptor mediated disorders. WO2013001294; 2013
   Google Scholar
• Hannson T, Berger M, Dahmen J, et al. Discovery of AZD5423, a potent and selective non-steroidal glucocorticoid receptor modulator for the inhaled treatment of respiratory diseases. 245th ACS Meeting; 2013. MEDI278
   Google Scholar
• O’Byrne PM, Gauvreau GM, Boulet LP, et al. Effect Of An Inhaled Selective Glucocorticoid Receptor Modulator (AZD5423) On Allergen-Induced Airway Responses And Airway Inflammation. Am J Respir Crit Care Med 2013;187:A2614
   Google Scholar
• Available from: http://clinicaltrials.gov/ct2/results?term=bi54903&Search=Search
   Google Scholar
• Norman P. New Combinations for asthma and COPD, in inhalation delivery. Scrip Business Insights 2013; In press
   Google Scholar
• Norman P. New dual acting bronchodilator treatments for COPD, muscarinic antagonists and beta 2 agonists in combination or combined into a single molecule. Exp Opin Investig Drugs, submitted
   Google Scholar
• AstraZeneca plc. AstraZeneca to acquire Pearl Therapeutics to strengthen respiratory portfolio, Press Release, 10 June 2013
   Google Scholar