Resolution of albuterol acetonide

Tetrahedron Asymmetry

Volumn 10, Issue 11, 1999, Pages 2175-2189

  Caira, Mino R ^a   Hunter, Roger ^a   Nassimbeni, Luigi R ^a   Stevens, Anne T ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; SALBUTAMOL; TARTARIC ACID DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DECOMPOSITION; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; STRUCTURE ANALYSIS;

EID: 0033522733     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00209-8     Document Type: Article

References (38)

1. Bakale, R. P. Speciality Chem. Prod., Market Applic. 1995, 15, 249.
2. 2-Stimulant Bronchodilator; Roberts, S. M.; Price, B. J., Eds.; Medicinal Chemistry: The Role of Organic Chemistry in Drug Research; Academic Press: London, 1985; pp. 49-91.
3. Hartley, D.; Middlemiss, D. J. Med. Chem. 1971, 14, 895.
4. Boulton, D. W.; Fawcett, J. P. Clin. Rev. Allerg. Immunol. 1996, 14, 115.
5. Perrin-Fayolle, M.; Blum, P. S.; Morley, J.; Grosclaude, M.; Chambe, M. T. Clin. Rev. Allerg. Immunol. 1996, 14, 139.
6. Templeton, A. G.; Chapman, I. D.; Chilvers, E. R.; Moreley, J.; Handley, D. A. Pulm. Pharmacol. Ther. 1998, 11, 1.
7. Nelson, H. S.; Bensch, G.; Pleskow, W. W.; Disantostefano, R.; DeGraw, S.; Reasner, D. S.; Rollins, T. E.; Rubin, P. D. J. Allergy Clin. Immunol. 1998, 102, 943.
8. FDA approval no: NDA 20-837; http://www.fda.gov./cder/approval/main2.htm.
9. Bakale, R. P.; Wald, S. A.; Butler, H. T.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. Clin. Rev. Allerg. Immunol. 1996, 14, 7.
10. Gao, Y.; Hong, Y.; Zepp, C. M. U.S. Patent # 5,442,118, 1995, 15 August.
11. Hawkins, C. J.; Klease, G. T. J. Med. Chem. 1973, 16, 856.
12. Gao, Y.; Zepp, C. M. U.S. Patent # 5,545,745, 1996, 13 August.
13. ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508.
14. Pihlaja, K.; Kleinpeter, E. Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH: New York, 1994; p. 175.
15. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; John Wiley: New York, 1981; pp. 217-250.
16. Wilen, S. H.; Collet, A.; Jacques, J. Tetrahedron 1977, 33, 2725.
17. Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 2349.
18. Collet, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3239.
19. Nemák, K.; Ács, M.; Jászay, Z. M.; Kozma, D.; Fogassy, E. Tetrahedron 1996, 52, 1637.
20. Mravik, A.; Lepp, Z.; Fogassy, E. Tetrahedron: Asymmetry 1996, 7, 2387.
21. Parker, D.; Taylor, R. J. Tetrahedron 1987, 43, 5451.
22. Adams, A. G.; Stewart, J. T. J. Liquid Chromatog. 1993, 16, 3863.
23. Effenberger, F.; Jäger, J. J. Org. Chem. 1997, 62, 3867.
24. Cambridge Structural Database and Cambridge Structural Database System Version 5.11 (April 1998), Cambridge Crystallographic Data Centre, University Chemical Laboratory, Cambridge, England.
25. Flack, H. D. Acta Cryst. 1983, A39, 876.
26. Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 107, 4342.
27. Halterman, R. L.; Vollhardt, K. P. C.; Welker, M. E. J. Am. Chem. Soc. 1987, 109, 8105.
28. Dehmlow, E. V.; Westerheide, R. Synthesis 1992, 947.
29. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
30. Ward, D. E.; Rhee, C. K. Tetrahedron Lett. 1991, 32, 7165.
31. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
32. Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 504 and references cited therein.
33. Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1996, 61, 8569.
34. Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929.
35. Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894.
36. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
37. Sheldrick, G. M. SHELXL-93. Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1993.
38. Otwinowski, Z.; Minor, W. Processing of X-Ray Diffraction Data in Oscillation Mode; Carter, C. W.; Sweet, R. M., Eds.; Methods in Enzymology; Academic Press: New York, 1996; Vol. 276, pp. 307-326.