References
Nelson, H. S., Alstair, J. J., and Wood, M. D., eds. (1995),N. Engl. J. Med. 333, 499–506.
Price, A. H. and Clissold, S. P. (1989),Drugs 38, 77–122.
Kelly, H. W. and Murphy, S. (1992),Annu. Pharmacother. 26, 81–91.
Siegel, D., Sheppard, D., Gelb, H., and Weinberg, P. F. (1985).Am. Rev. Respir. Dis. 132, 283–286.
Godfrey, S. and Konig, P. (1976),Thorax 31, 137–143.
Hopkins, S. J. (1979),Drugs Future 4, 629–633.
Silverman, R. B. (1992),The Organic Chemistry of Drug Design and Drug Action, Academic, San Diego, CA.
Hochhaus, G. and Mollmann, H. (1992),Int. J. Clin. Pharm. Therap. Tox. 30, 342–362.
Thiringer, G. and Svedmyr, N. (1977),Scand. J. Respir. Dis. Suppl. 101, 95,96.
Byron, R. R. (1990),Respiratory Drug Delivery, CRC Press, Boca Raton, FL.
Aboul-Enein, H. Y. and Serignese, V. (1995),Chirality 7, 158–162.
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.
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.
Aboul-Enien, H. Y., Al-Badr, A. A., and Ibrahim, S. E. (1981), inAnalytical Profiles of Drug Substances, vol. 10, Florey, K., ed., Academic, New York, pp. 665–689.
Kucharczyk, N. and Segelman, F. H. (1985),J. Chromatogr. 340, 243–271.
Wu, Y. Q., Shi, R., Williams, R. L., and Lin, E. T. (1991),J. Liquid Chromatogr. 14, 253–256.
McCarthy, P. T., Atwal, S., Sykes, A. P., and Ayres, M. (1993),Biomed. Chromatogr. 7, 25–28.
Sagar, K. A., Kelley, M. T., and Smyth, M. R. (1993),Biomed. Chromatogr. 7, 29–33.
He, L. and Stewart, J. T. (1992),Biomed. Chromatogr. 6, 291–299.
Adams, A. G. and Stewart, J. T. (1993),J. Liquid Chromatogr.,16, 3863–3875.
Malkki-Lanine, L., Purra, K., Kahkonen, K., and Tanmilehto, S. (1995),Int. J. Pharmacol. 117, 189–195.
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.
Hartley, D., Jack, D., Lunts, L. H. C., and Ritchie, A. C. (1968),Nature 219, 861,862.
Kawamatsu, Y., Asagawa, H., Ingmiya, E., and Hivano, H. (1974), Japanese Patent, #74-70939.
Lednicer, D. and Mitscher, L. A. (1980),The Organic Chemistry of Drug Synthesis, vol. 2, Wiley, New York, p. 43.
Grummitt, O., Buck, A., and Horning, E. C., eds. (1955),1-Chloromethylnaphthalene: Organic Synth Col, vol. 3, Wiley, New York, pp. 195–197.
Leclerc, G. and Bizec, J. C. (1980),J. Med. Chem. 23, 738–744.
Roth, H. J. and Kleemann, H. (1988),Phenylalkylamines: Pharmaceutical Chemistry Volume 1: Drug Synthesis, Ellis Harwood and Wiley, New York, pp. 56,57.
Collins, D. T. (1972),Process for the Preparation of Tertiary Butylaminomethyl-4-Hydroxy m-Xylene Diol. US Patent #3,642,896, Feb. 2.
Skachilova, S. Y., Zueyava, E. F., and Muravskaya, I. D. (1991),Khimiko-Farmatsevtcheskii Zhurnal 25, 59–65.
Lunts, L. H. C. and Toon, P. (1971),Gyloxals and Production Thereof. British Patent #1,247,370, Sept. 22.
Floyd, M. B., Du, M. T., Fabio, P. F., Jacob, L. A., and Johnson, B. D. (1985),J. Org. Chem. 50, 5022–5027.
Desmond, R., Mills, S., Volante, P. P., and Shinkai, I. (1989),Synthetic Comm. 19, 379–385.
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.
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.
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.
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.
Alcaide, B., Escobar, G., Ossorio, R. P., Plumet, J., and Sanz, D. (1984),J. Chem. Res. 5, 144,145.
Gunn, V. E. and Anseline, J. P. (1977),J. Org. Chem. 42, 754.
Riley, H. A., Gray, A. R., and Blatt, A. H., eds. (1943), inOrganic Synth Col, vol. 2, Wiley, New York, pp. 509–511.
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.
Lunts, L. H. C., Toon, P., and Collin, D. T. (1967),Phenylaminoethanol Derivatives. British Patent #1,200,886, Sept. 15.
Lunts, L. H. C. (1993), inMedicinal Chemistry, 2nd ed., Ganellin, C. R. and Roberts, S., eds., Academic, New York, pp. 209–226.
Hartley, D. and Middlemiss, D. (1971),J. Med. Chem. 14, 895–899.
Hoshiko, K. I. and Morley, I. (1993),Jpn. J. Pharmacol. 63, 159–163.
Hoshiko, K. I., Kristersson, A., and Morley, J. (1993),J. Allergy Clin Immunol. 91, 909–916.
Chapman, I. D., Buchheit, K. H., Manley, P., and Morley, J. (1992),Trends Pharmacol. Sci. 13, 231,232.
Morley, J., Chapman, I. D., Foster, A., Hoshilo, K., and Mazzoni, L. (1991),Br. J. Pharmacol. 104, 295P.
Walle, T., Pesola, G. R., and Walle, P. (1993),Br. J. Clin. Pharmacol. 35, 413–418.
Gallard, B. C. and Blackman, J. G. (1993),Br. J. Pharmacol. 108, 1016–1023.
Eliel, E. L., Wilen, S. H., and Mander, L. N. (1994),Sterochemistry of Organic Compounds, Wiley, New York.
Orchin, M., Kaplan, F., Macomber, R. S., Wilson, R. M., and Zimmer, H. (1980),The Vocabulary of Organic Chemistry, Wiley, New York.
Bakale, R. P. (1995),Specialty Chem. Prod., Market. Applic. 15, 249–253.
Csuk, R. and Glanzer, B. I. (1991),Chem. Rev. 91, 49–97.
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.
Wallbaum, S. and Martens, J. (1992),Tett. Asym. 3, 1475–1504.
Singh, V. K. (1992),Synthesis July, 605–620.
Deloux, L. and Srebnik, M. (1991),Chem. Rev.,91, 49–97.
Hong, Y., Gao, Y., Nie, X., and Zepp, C. M. (1994),Tett. Lett. 35, 5551–5554.
Zhu, Q. C., Hutchins, R. O., and Hutchins, M. K. (1994),Org. Prep. Proc. Int. 26, 193–236.
Hirao, A., Itsuno, S., Nakahama, S., and Yamazaki, N. (1981),J. Chem. Soc. Chem. Comun. 7, 315–317.
Itsuno, S., Hirao, A., Nakahama, S., and Yamazaki, Y. (1983),J. Chem. Perkin. Trans. 8, 1673–1676.
Itsuno, S., Sakurai, Y., Ito, K., Hirao, A., and Nakahama, S. (1987),Bull. Chem. Soc. Jpn. 60, 395,396.
Corey, E. J., Bakshi, R. K., and Shibata, S. (1987),J. Am. Chem. Soc. 109, 5551–5553.
Corey, E. J., Shibata, E., and Bakshi, R. K. (1988),J. Org. Chem. 53, 2861–2863.
Corey, E. J. and Link, J. O. (1992),Tett. Lett. 33, 3431–3434.
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.
Quallich, G. J. and Woodall, T. M. (1993),Tett. Lett. 34, 4145–4148.
Quallich, G. J. and Woodall, T. M. (1993),Synlett. Dec., 929–930.
Martens, J. and Mehler, T. (1993),Tett. Asym. 4, 1983–1986.
Martens, J. and Mehler, T. (1993),Tett. Asym. 4, 2299–2302.
Hong, Y., Gao, Y., Nie, X., and Zepp, C. M. (1994),Tett. Lett. 35, 6631–6634.
Simone, B. D., Savoia, D., Tagliauini, E., and Ronchi, A. O. (1995),Tett. Asym. 6, 301–306.
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.
Hett, R., Stare, R., and Helquist, P. (1994),Tett. Lett. 35, 9375–9378.
Corey, E. J. and Link, J. O. (1991),J. Org. Chem. 56, 442–444.
Cho, B. T. and Chun, Y. S. (1992),Tett. Asym. 3, 341,342.
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.
Cavallo, A. S., Simon-Wermeister, M. C., and Farkhami, D. (1991),Helv. Chimi. Acta. 74, 390–396.
Main, B. G. and Tucker, H. (1993), inMedicinal Chemistry, 2nd ed., Academic, New York, pp. 187–208.
Gao, Y. and Zepp, C. M. (1995),Enantioselective Preparation of Optically Pure Albuterol. US Patent #5,399,765, March 21.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bakale, R.P., Wald, S.A., Butler, H.T. et al. Albuterol. Clinic Rev Allerg Immunol 14, 7–35 (1996). https://doi.org/10.1007/BF02772200
Issue Date:
DOI: https://doi.org/10.1007/BF02772200