Inhalation by design: Novel ultra-long-acting β2- adrenoreceptor agonists for inhaled once-daily treatment of asthma and chronic obstructive pulmonary disease that utilize a sulfonamide agonist headgroup

Journal of Medicinal Chemistry

Volumn 53, Issue 18, 2010, Pages 6640-6652

  Glossop, Paul A ^a   Lane, Charlotte A L ^a   Price, David A ^a   Bunnage, Mark E ^a   Lewthwaite, Russell A ^a   James, Kim ^a   Brown, Alan D ^a   Yeadon, Michael ^a   Perros Huguet, Christelle ^a   Trevethick, Michael A ^a   Clarke, Nicholas P ^a   Webster, Robert ^a   Jones, Rhys M ^a   Burrows, Jane L ^a   Feeder, Neil ^a   Taylor, Stefan C J ^a   Spence, Fiona J ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINE; BETA 2 ADRENERGIC RECEPTOR STIMULATING AGENT; CYCLIC AMP; FORMOTEROL; PF 610355; SALMETEROL; SULFONAMIDE; ZINTEROL; BENZENEACETAMIDE DERIVATIVE; BETA ADRENERGIC RECEPTOR STIMULATING AGENT; N-((4'-HYDROXYBIPHENYL-3-YL)METHYL)-2-(3-(2-((-2-HYDROXY-2-(4-HYDROXY-3-((METHYLSULFONYL)AMINO)PHENYL)ETHYL)AMINO)-2-METHYLPROPYL)PHENYL)ACETAMIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ASTHMA; CHO CELL; CHRONIC OBSTRUCTIVE LUNG DISEASE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DOG; DRUG CLEARANCE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; FEMALE; GUINEA PIG; NONHUMAN; REACTION ANALYSIS; SMOOTH MUSCLE RELAXATION; ANIMAL; BRONCHOCONSTRICTION; CHEMICAL STRUCTURE; CHO CELL LINE; CRICETULUS; DRUG EFFECTS; HAMSTER; HUMAN; IN VITRO STUDY; INHALATIONAL DRUG ADMINISTRATION; LIVER; LIVER CELL; LIVER MICROSOME; MALE; METABOLISM; PATHOPHYSIOLOGY; PULMONARY DISEASE, CHRONIC OBSTRUCTIVE; RAT; SMOOTH MUSCLE; STEREOISOMERISM; SYNTHESIS; TRACHEA; X RAY CRYSTALLOGRAPHY;

ADMINISTRATION, INHALATION; ADRENERGIC BETA-AGONISTS; ANIMALS; ASTHMA; BENZENEACETAMIDES; BRONCHOCONSTRICTION; CHO CELLS; CRICETINAE; CRICETULUS; CRYSTALLOGRAPHY, X-RAY; DOGS; FEMALE; GUINEA PIGS; HEPATOCYTES; HUMANS; LIVER; MALE; MICROSOMES, LIVER; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUSCLE, SMOOTH; PULMONARY DISEASE, CHRONIC OBSTRUCTIVE; RATS; RECEPTORS, ADRENERGIC, BETA-2; STEREOISOMERISM; SULFONAMIDES; TRACHEA; ADRENERGIC BETA-2 RECEPTOR AGONISTS; IN VITRO TECHNIQUES;

EID: 77956766674     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1005989     Document Type: Article

References (38)

1. 2 adrenergic receptor agonists incorporating arylsulfonamide groups J. Med. Chem. 2009, 52, 2280-2288
2. 2-adrenoceptor agonists as inhaled long-acting bronchodilators Bioorg. Med. Chem. Lett. 2010, 20, 5302-5307
3. 2-adrenoceptor agonist J. Med. Chem. 2010, 53, 3675-3684
4. Cazzola, M.; Segreti, A.; Matera, M. G. Novel bronchodilators in asthma Curr. Opin. Pulm. Med. 2010, 16, 6-12
5. 2 adrenergic receptor agonists incorporating metabolic inactivation: an antedrug approach J. Med. Chem. 2010, 53, 4522-4530
6. 2-adrenoceptor agonist with a 24h bronchodilatory efficacy Bioorg. Med. Chem. Lett. 2010, 20, 1410-1414
7. 2- adrenoceptor agonists for the treatment of asthma and COPD Bioorg. Med. Chem. Lett. 2007, 17, 6188-6191
8. 2- adrenoreceptor agonists Bioorg. Med. Chem. Lett. 2007, 17, 4012-4015
9. 2-adrenoreceptor agonists Bioorg. Med. Chem. Lett. 2008, 18, 1280-1283
10. 2-Adrenoceptor Agonists for Asthma and COPD. Presented at the ACS ProSpectives Conference: Discovery and Selection of Successful Drug Candidates, San Francisco, CA, May 4-7, 2008.
11. Hett, R.; Fang, Q. K.; Gao, Y.; Wald, S. A.; Senanayake, C. H. Large-scale synthesis of enantio-and diastereomerically pure (R, R)-formoterol Org. Process Res. Dev. 1998, 2, 96-99
12. Ritter, J. J.; Kalish, J. New reaction of nitriles. II. Synthesis of t-carbinamines J. Am. Chem. Soc. 1948, 70, 4048-4050
13. Jirgensons, A.; Kauss, V.; Kalvinsh, I.; Gold, M. R. A practical synthesis of tert-alkylamines via the ritter reaction with chloroacetonitrile Synthesis 2000, 12, 1709-1712
14. Brown, A. D.; Bunnage, M. E.; Glossop, P. A.; James, K.; Lane, C. A. L.; Lewthwaite, R. A.; Moses, I. B.; Price, D. A.; Thomson, N. M. A Preparation of Sulfonamide Derivatives of (Aminoethyl)phenols, Useful for the Treatment of Allergic and Respiratory Diseases. U.S. Pat. Appl. Publ. US 2005182091, 2005.
15. Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates J. Med. Chem. 2002, 45, 2615-2623
16. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25
17. Trofast, J.; Österberg, K.; Källström, B.-L.; Waldeck, B. Steric aspects of agonism and antagonism at β-adrenoreceptors: synthesis and pharmacological experiments with the enantiomers of formoterol and their diastereomers Chirality 1991, 3, 443-450
18. 2- adrenoceptor agonist, salmeterol Br. J. Pharmacol. 1993, 108, 507-515
19. Fisher, M. B.; Paine, M. F.; Strelevitz, T. J.; Wrighton, S. A. The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism Drug Metab. Rev. 2001, 33, 273-297
20. 2-adrenergic receptor and its binding site for agonists and antagonists Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 2736-2741 (Pubitemid 38327680)
21. Manchee, G. R.; Barrow, A.; Kulkarni, S.; Palmer, E.; Oxford, J.; Colthup, P. V.; Maconopchie, J. G.; Tarbit, M. H. Disposition of salmeterol xinafoate in laboratory animals and humans Drug Metab. Dispos. 1993, 21, 1022-1028 (Pubitemid 23348338)
22. 2-adrenoceptor agonist with a long duration of action. Eur. Respir. J. 2009, 34 (S53), Abstract P2067.
23. 2-adrenoceptor agonist bronchodilator Life Sci. 1993, 52, 2145-2160
24. Anderson, G. P.; Linden, A.; Rabe, K. F. Why are long-acting beta-adrenoceptor agonists long-acting? Eur. Respir. J. 1994, 7, 569-578
25. Johnson, M.; Butchers, P. R.; Coleman, R. A.; Nials, A. T.; Strong, P.; Summer, M. J.; Vardey, C. J.; Whelan, C. J. The pharmacology of salmeterol Life Sci. 1993, 52, 2131-2143
26. 2-adrenoceptor agonists TIPS 1996, 17, 324-330
27. 2-adrenoceptor agonist, in anaesthetised animals. Eur. Respir. J. 2009, 34 (S53), Abstract P2020.
28. 2-adrenoceptor agonist with superior potency and duration of action (DoA) to salmeterol in the conscious dog model of bronchoconstriction. Eur. Respir. J. 2009, 34 (S53), Abstract P2060.
29. Artursson, P.; Palm, K.; Luthman, K. Caco-2 monolayers in experimental and theoretical predictions of drug transport Adv. Drug Delivery Rev. 1996, 22, 67-84
30. Taburet, A. M.; Schmit, B. Pharmacokinetic optimization of asthma treatment Clin. Pharmacokinet. 1994, 26, 396-418
31. Kilford, P. J.; Stringer, R.; Sohal, B.; Houston, J. B.; Galetin, A. Prediction of drug clearance by glucuronidation from in vitro data: use of combined cytochrome P450 and UDP-glucuronosyltransferase cofactors in alamethicin-activated human liver microsomes Drug Metab. Dispos. 2009, 37, 82-89
32. Bennett, J. A.; Harrison, T. W.; Tattersfield, A. E. The contribution of the swallowed fraction of an inhaled dose of salmeterol to it systemic effects Eur. Respir. J. 1999, 13, 445-448
33. Assessment Report for Onbrez Breezhaler; EMA/659981/2009; European Medicines Agency: London, Dec 17, 2009.
34. 2-adrenoreceptor agonist, PF-00610355. Eur. Respir. J. 2009, 34 (S53), Abstract P2017.
35. 2-adrenoreceptor agonist. Eur. Respir. J. 2009, 34 (S53), Abstract E4354.
36. 2- adrenoreceptor agonist. Eur. Respir. J. 2009, 34 (S53), Abstract P2018.
37. 2-adrenoreceptor agonist, PF-00610355, in asthmatic patients. Eur. Respir. J. 2009, 34 (S53), Abstract E4355.
38. Ribbing, J.; Li, G. L.; Van Schaick, E.; Harnisch, L. Assessing the therapeutic benefit of a new inhaled QD LABA through population PK-safety and efficacy modelling. Eur. Respir. J. 2009, 34 (S53), Abstract P2021.