Albuterol: A Pharmaceutical Chemistry Review of R-, S-, and RS-Albuterol

Clinical Reviews in Allergy and Immunology

Volumn 14, Issue 1, 1996, Pages 7-35

  Bakale, Roger P ^a   Wald, Stephen A ^a   Butler, Hal T ^a   Gao, Yun ^a   Hong, Yaping ^a   Nie, Xiaoyi ^a   Zepp, Charles M ^a  

^a SUNOVION PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SALBUTAMOL;

ANIMAL; CHEMISTRY; DRUG SCREENING; HUMAN; PHYSICAL CHEMISTRY; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALBUTEROL; ANIMALS; CHEMISTRY, PHYSICAL; DRUG EVALUATION; DRUG EVALUATION, PRECLINICAL; HUMANS; STEREOISOMERISM;

EID: 0030090718     PISSN: 10800549     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02772200     Document Type: Review

References (81)

1. Nelson, H. S., Alstair, J. J., and Wood, M. D., eds. (1995), N. Engl. J. Med. 333, 499-506.
2. Price, A. H. and Clissold, S. P. (1989), Drugs 38, 77-122.
3. Kelly, H. W. and Murphy, S. (1992), Annu. Pharmacother. 26, 81-91.
4. Siegel, D., Sheppard, D., Gelb, H., and Weinberg, P. F. (1985) Am. Rev. Respir. Dis. 132, 283-286.
5. Godfrey, S. and Konig, P. (1976), Thorax 31, 137-143.
6. Hopkins, S. J. (1979), Drugs Future 4, 629-633.
7. Silverman, R. B. (1992), The Organic Chemistry of Drug Design and Drug Action, Academic, San Diego, CA.
8. Hochhaus, G. and Mollmann, H. (1992), Int. J. Clin. Pharm. Therap. Tox. 30, 342-362.
9. Thiringer, G. and Svedmyr, N. (1977), Scand. J. Respir. Dis. Suppl. 101, 95,96.
10. Byron, R. R. (1990), Respiratory Drug Delivery, CRC Press, Boca Raton, FL.
11. Aboul-Enein, H. Y. and Serignese, V. (1995), Chirality 7, 158-162.
12. Spitzer, N. O., Suissa, S., Ernst, P., Horwitz, R. I., Habbick, B., Cockcroft, D., Boivin, J. F., McNutt, M., Buist, A. S., and Rebuck, A. S. (1992), N. Engl. J. Med. 326, 501-506.
13. Sears, M. R., Taylor, D. R., Print, C. G., Lake, D. C., Li, Q. Q., Flannery, E. M., Yates, D. M., Lucas, M. K., and Herbison, G. P. (1990), Lancet 336, 1391-1396.
14. Aboul-Enien, H. Y., Al-Badr, A. A., and Ibrahim, S. E. (1981), in Analytical Profiles of Drug Substances, vol. 10, Florey, K., ed., Academic, New York, pp. 665-689.
15. Kucharczyk, N. and Segelman, F. H. (1985), J. Chromatogr. 340, 243-271.
16. Wu, Y. Q., Shi, R., Williams, R. L., and Lin, E. T. (1991), J. Liquid Chromatogr. 14, 253-256.
17. McCarthy, P. T., Atwal, S., Sykes, A. P., and Ayres, M. (1993), Biomed. Chromatogr. 7, 25-28.
18. Sagar, K. A., Kelley, M. T., and Smyth, M. R. (1993), Biomed. Chromatogr. 7, 29-33.
19. He, L. and Stewart, J. T. (1992), Biomed. Chromatogr. 6, 291-299.
20. Adams, A. G. and Stewart, J. T. (1993), J. Liquid Chromatogr. 16, 3863-3875.
21. Malkki-Lanine, L., Purra, K., Kahkonen, K., and Tanmilehto, S. (1995), Int. J. Pharmacol. 117, 189-195.
22. Collins, D. T., Hartley, D., Jack, D., Lunts, L. H. C., Press, J. C., Richie, A. C., and Toon, P. (1970), J. Med. Chem. 13, 674-680.
23. Hartley, D., Jack, D., Lunts, L. H. C., and Ritchie, A. C. (1968), Nature 219, 861,862.
24. Kawamatsu, Y., Asagawa, H., Ingmiya, E., and Hivano, H. (1974), Japanese Patent, #74-70939.
25. Lednicer, D. and Mitscher, L. A. (1980), The Organic Chemistry of Drug Synthesis, vol. 2, Wiley, New York, p. 43.
26. Grummitt, O., Buck, A., and Horning, E. C., eds. (1955), 1-Chloromethylnaphthalene: Organic Synth Col, vol. 3, Wiley, New York, pp. 195-197.
27. Leclerc, G. and Bizec, J. C. (1980), J. Med. Chem. 23, 738-744.
28. Roth, H. J. and Kleemann, H. (1988), Phenylalkylamines: Pharmaceutical Chemistry Volume 1: Drug Synthesis, Ellis Harwood and Wiley, New York, pp. 56,57.
29. Collins, D. T. (1972), Process for the Preparation of Tertiary Butylaminomethyl-4-Hydroxy m-Xylene Dial. US Patent #3,642,896, Feb. 2.
30. Skachilova, S. Y., Zueyava, E. F., and Muravskaya, I. D. (1991), Khimiko-Farmatsevtcheskii Zhurnal 25, 59-65.
31. Lunts, L. H. C. and Toon, P. (1971), Gyloxals and Production Thereof. British Patent #1,247,370, Sept. 22.
32. Floyd, M. B., Du, M. T., Fabio, P. F., Jacob, L. A., and Johnson, B. D. (1985), J. Org. Chem. 50, 5022-5027.
33. Desmond, R., Mills, S., Volante, P. P., and Shinkai, I. (1989), Synthetic Comm. 19, 379-385.
34. Tann, C. H., Thiruvengedam, T. K., Green, M., McCallister, T. L., and Lee, J. (1990), Process for Preparing Albuterol, Acetal, Hemi-Acetal, and Hydrates of Arylgyloxal Intermediates Thereof. US Patent #91/66248, Sept. 11.
35. Tann, C. H., Thiruvengedam, T. K., Green, M., McCallister, T. L., and Lee, J. (1991), Process for Preparing Albuterol, Acetal, Hemi-Acetal, and Hydrates of Arylgyloxal Intermediates Thereof. International Patent #PTC/US91/06248, Sept. 6.
36. Tann, C. H., Thiruvengedam, T. K., Green, M., McCallister, T. L., and Lee, J. (1992), Process for Preparing Albuterol, Acetal, Hemi-Acetal, and Hydrates of Arylgyloxal Intermediates Thereof. Canadian Patent #WO/92/04314, March 19.
37. Tann, C. H., Thiruvengedam, T. K., Green, M., McCallister, T. L., and Lee, J. (1994), Process for Preparing Albuterol, Acetal, Hemi-Acetal, and Hydrates of Arylgyloxal Intermediates Thereof. US Patent #5,283,359, Feb. 1.
38. Alcaide, B., Escobar, G., Ossorio, R. P., Plumet, J., and Sanz, D. (1984), J. Chem. Res. 5, 144,145.
39. Gunn, V. E. and Anseline, J. P. (1977), J. Org. Chem. 42, 754.
40. Riley, H. A., Gray, A. R., and Blatt, A. H., eds. (1943), in Organic Synth Col. vol. 2, Wiley, New York, pp. 509-511.
41. Babad, E., Carruthers, N., and Steinman, M. (1991), Method for the Preparation of (1,1-Dimethylethyl)Amino-Methyl-4-Hydroxy-1,3-Benzenedimethanol. US Patent #5,011,993, Apr. 30.
42. Lunts, L. H. C., Toon, P., and Collin, D. T. (1967), Phenylaminoethynol Derivatives. British Patent #1,200,886, Sept. 15.
43. Lunts, L. H. C. (1993), in Medicinal Chemistry, 2nd ed., Ganellin, C. R. and Roberts, S., eds., Academic, New York, pp. 209-226.
44. Hartley, D. and Middlemiss, D. (1971), J. Med. Chem. 14, 895-899.
45. Hoshiko, K. I. and Morley, I. (1993), Jpn. J. Pharmacol. 63, 159-163.
46. Hoshiko, K. I., Kristersson, A., and Morley, J. (1993), J. Allergy Clin. Immunol. 91, 909-916.
47. Chapman, I. D., Buchheit, K. H., Manley, P., and Morley, J. (1992), Trends Pharmacol. Sci. 13, 231,232.
48. Morley, J., Chapman, I. D., Foster, A., Hoshilo, K., and Mazzoni, L. (1991), Br. J. Pharmacol. 104, 295P.
49. Walle, T., Pesola, G. R., and Walle, P. (1993), Br. J. Clin. Pharmacol. 35, 413-418.
50. Gallard, B. C. and Blackman, J. G. (1993), Br. J. Pharmacol. 108, 1016-1023.
51. Eliel, E. L., Wilen, S. H., and Mander, L. N. (1994), Stereochemistry of Organic Compounds, Wiley, New York.
52. Orchin, M., Kaplan, F., Macomber, R. S., Wilson, R. M., and Zimmer, H. (1980), The Vocabulary of Organic Chemistry, Wiley, New York.
53. Bakale, R. P. (1995), Specialty Chem. Prod., Market. Applic. 15, 249-253.
54. Csuk, R. and Glanzer, B. I. (1991), Chem. Rev. 91, 49-97.
55. Nakamura, K., Kawai, Y., Kitayama, T., Miyai, M., Ogawa, Y., Mikata, M., and Higaki, A. (1989), Ohno. Bull. Inst. Chem. Res. Kyoto Univ. 67, 157-168.
56. Wallbaum, S. and Martens, J. (1992), Tett. Asym. 3, 1475-1504.
57. Singh, V. K. (1992), Synthesis July, 605-620.
58. Deloux, L. and Srebnik, M. (1991), Chem. Rev. 91, 49-97.
59. Hong, Y., Gao, Y., Nie, X., and Zepp, C. M. (1994), Tett. Lett. 35, 5551-5554.
60. Zhu, Q. C., Hutchins, R. O., and Hutchins, M. K. (1994), Org. Prep. Proc. Int. 26, 193-236.
61. Hirao, A., Itsuno, S., Nakahama, S., and Yamazaki, N. (1981), J. Chem. Soc. Chem. Comun. 7, 315-317.
62. Itsuno, S., Hirao, A., Nakahama, S., and Yamazaki, Y. (1983), J. Chem. Perkin. Trans. 8, 1673-1676.
63. Itsuno, S., Sakurai, Y., Ito, K., Hirao, A., and Nakahama, S. (1987), Bull. Chem. Soc. Jpn. 60, 395,396.
64. Corey, E. J., Bakshi, R. K., and Shibata, S. (1987), J. Am. Chem. Soc. 109, 5551-5553.
65. Corey, E. J., Shibata, S., and Bakshi, R. K. (1988), J. Org. Chem. 53, 2861-2863.
66. Corey, E. J. and Link, J. O. (1992), Tett. Lett. 33, 3431-3434.
67. Mathre, D. J., Thompson, A. S., Douglas, A. W., Hoogsteen, K., Carroll, J. P., Corley, E. G., and Grabowski, E. J. J. (1993), J. Org. Chem. 58, 2880-2888.
68. Quallich, G. J. and Woodall, T. M. (1993), Tett. Lett. 34, 4145-4148.
69. Quallich, G. J. and Woodall, T. M. (1993), Synlett. Dec., 929-930.
70. Martens, J. and Mehler, T. (1993), Tett. Asym. 4, 1983-1986.
71. Martens, J. and Mehler, T. (1993), Tett. Asym. 4, 2299-2302.
72. Hong, Y., Gao, Y., Nie, X., and Zepp, C. M. (1994), Tett. Lett. 35, 6631-6634.
73. Simone, B. D., Savoia, D., Tagliauini, E., and Ronchi, A. O. (1995), Tett. Asym. 6, 301-306.
74. Gao, Y., Hong, Y., Nie, X., and Zepp, C. M. (1995), Asymmetric Synthesis of (R)- and (S)-Arylethanolamines from Iminoketones. US Patent #5,442,118, August 15.
75. Hett, R., Stare, R., and Helquist, P. (1994), Tett. Lett. 35, 9375-9378.
76. Corey, E. J. and Link, J. O. (1991), J. Org. Chem. 56, 442-444.
77. Cho, B. T. and Chun, Y. S. (1992), Tett. Asym. 3, 341,342.
78. Bhattacharya, A., Fritch, J. R., Murphy, C. D., Zeagler, L. D., and Araullo-McAdams, C. (1994), Racemization of an Enantiomerically Enriched α-Aryl Carboxylic Acid. US Patent #5,332,834, July 26.
79. Cavallo, A. S., Simon-Wermeister, M. C., and Farkhami, D. (1991), Helv. Chimi. Acta. 74, 390-396.
80. Main, B. G. and Tucker, H. (1993), in Medicinal Chemistry, 2nd ed., Academic, New York, pp. 187-208.
81. Gao, Y. and Zepp, C. M. (1995), Enantioselective Preparation of Optically Pure Albuterol. US Patent #5,399,765, March 21.