Adrenoceptor Antagonists

  • Alan F. Casy
  • George H. Dewar


This chapter is devoted to ligands which block adrenoceptors. Although some agents of this kind have already been mentioned in the preceding chapter as a result of the often quite close structural resemblances between agonists and antagonists, the amount of published material on antagonists warrants their separate discussion. Adrenoceptor antagonists fall into two classes, namely α- and β-blocking agents, a fact which in itself adds credence to the overall division of adrenoceptors into these two principal subtypes.


ADRENOCEPTOR Antagonist Levo Bunolol Crotyl Alcohol Antipodal Pair Stereospecific Synthesis 
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  1. 1.
    P. B. M. W. M. Timmermans, A. T. Chiu, and M. J. M. C. Thoolen, in: Comprehensive Medicinal Chemistry, Vol. 3, Membranes and Receptors, (J. C. Emett, ed.), Chap. 12.1, p. 133, Pergamon Press, New York (1990).Google Scholar
  2. 2.
    E. Forneau, D. Bovet, and P. Maderni, J. Pharm. Chim. 18, 185 (1933);Google Scholar
  3. 2a.
    E. Forneau and D. Bovet, C. R. Seances Soc. Biol. SesFil. 113, 388 (1933).Google Scholar
  4. 3.
    L. H. Werner and W. E. Barrett, in: Antihypertensive Agents (E. Schütter, ed.), pp. 331–392, Academic Press, New York (1967).Google Scholar
  5. 4.
    W. L. Nelson, J. E. Wennerstrom, D. C. Dyer, and M. Engel, J. Med. Chem. 20, 880 (1977).PubMedCrossRefGoogle Scholar
  6. 5.
    R. R. Ruffolo Jr., J. W. Fowble, D. D. Miller, and P. N. Patil, Proc. Natl. Acad. Sci. USA 73, 3730 (1976).CrossRefGoogle Scholar
  7. 6.
    W. L. Nelson, M. L. Powell, and D. C. Dyer, J. Med. Chem. 22, 1125 (1979).PubMedCrossRefGoogle Scholar
  8. 7.
    D. R. Mottran and H. Kapur, J. Pharm. Pharmacol. 27, 295 (1975);CrossRefGoogle Scholar
  9. 7a.
    H. Kapur, D. R. Mottram, and P. N. Green, J. Pharm. Pharmacol. 30, 259 (1978);PubMedCrossRefGoogle Scholar
  10. 7b.
    H. Kapur and D. R. Mottram, Biochem. Pharmacol. 27, 1879 (1978).PubMedCrossRefGoogle Scholar
  11. 8.
    C. Melchiorre, L. Brasili, D. Giardinà, M. Pigini, and G. Strappaghetti, J. Med. Chem. 27, 1535 (1984).PubMedCrossRefGoogle Scholar
  12. 9.
    A. Cassinelli, W. Quaglia, D. Giardinà, U. Gulini, and C. Melchiorre, Eur. J. Med. Chem. 22, 23 (1987).CrossRefGoogle Scholar
  13. 10.
    W. Quaglia, M. Pigini, M. Gianella, and C. Melchiorre, J. Med. Chem. 33, 2946 (1990).PubMedCrossRefGoogle Scholar
  14. 11.
    C.B. Chapleo, P. L. Myers, R. C. M. Butler, J. C. Doxey, A. G. Roach, and C. F. C. Smith, J. Med. Chem. 26, 823 (1983).PubMedCrossRefGoogle Scholar
  15. 12.
    H. Dabiré, P. Mouille, and H. Schmitt, Eur. J. Pharmacol. 86, 83 (1983).CrossRefGoogle Scholar
  16. 13.
    A. P. Welbourn, C.B. Chapleo, A.C. Lane, P. L. Myers, A. G. Roach, and C. F. C. Smith, J. Med. Chem. 29, 2000 (1986).PubMedCrossRefGoogle Scholar
  17. 14.
    B. Wilffert, M. J. Mathyl, H. D. Batink, A. De Jong, M. J. M. C. Thoolen, G. Prop, E. Graf, P. B. M. W. M. Timmermans, and P. A. Van Zwieten, Arch. Int. Pharmacol. 273, 18 (1985).Google Scholar
  18. 15.
    M. R. Stillings, C.B. Chapleo, R. C. M. Butler, J. A. Davis, C.D. England, M. Myers, P. L. Myers, N. Tweddle, A. P. Welbourn, J. C. Doxey, and C. F. C. Smith, J. Med. Chem. 28, 1054 (1985).PubMedCrossRefGoogle Scholar
  19. 16.
    M. R. Goldberg and D. Robertson, Pharmacol. Rev. 35, 143 (1983).PubMedGoogle Scholar
  20. 17.
    R. D. Clark, A. D. Michel, and R. L. Whiting, Prog. Med. Chem. 23, 1 (1986).PubMedCrossRefGoogle Scholar
  21. 18.
    K. Stark, E. Borowski, and T. Endo, Eur. J. Pharmacol. 34, 385 (1975).CrossRefGoogle Scholar
  22. 19.
    N. Ferry, M. Goodhardt, J. Hanoune, and T. Sevenet, Br. J. Pharmacol. 78, 359 (1983).PubMedCrossRefGoogle Scholar
  23. 20.
    J. J. Baldwin, J. R. Huff, W. C. Randall, J. P. Vacca, and M. M. Zrada, Eur. J. Med. Chem. 20, 67 (1985).Google Scholar
  24. 21.
    P. B. M. W. M. Timmermans, A. M. C. Schoop, H. Y. Kwa, and P.A. Van Zwieten, Eur. J. Pharmacol. 70, 7 (1981).PubMedCrossRefGoogle Scholar
  25. 22.
    R. Weitzeil, T. Tanaka, and K. Starke, NS Arch. Pharmacol. 308, 127 (1979).CrossRefGoogle Scholar
  26. 23.
    K. Starke, Rev. Physiol. Biochem. Pharmacol. 88, 199 (1981).PubMedCrossRefGoogle Scholar
  27. 24.
    J. E. Saxton, in: The Alkaloids, Vol. VIII, p. 37, Academic Press, New York (1960).Google Scholar
  28. 25.
    E. E. Van Tamelen and W. C. Proost. J. Am. Chem. Soc. 76, 3632 (1954);CrossRefGoogle Scholar
  29. 25a.
    E. E. Van Tamelen, M. Shamma, and P. Aldrich, J. Am. Chem. Soc. 78, 4628 (1956).CrossRefGoogle Scholar
  30. 26.
    G. Stork and R. K. Hill, J. Am. Chem. Soc. 76, 949 (1954); 79, 495 (1957).CrossRefGoogle Scholar
  31. 27.
    M.-M. Janot, R. Goutarel, A. Le Hir, M. Amin, and V. Prelog, Bull. Soc. Chim. France 1085 (1952).Google Scholar
  32. 28.
    A. Le Hir, M.-M. Janot, and R. Goutarel, Bull. Soc. Chim. France 1027 (1952).Google Scholar
  33. 29.
    A. Chatterjee and S. C. Pakrashi, Naturwiss 41, 215 (1954).CrossRefGoogle Scholar
  34. 30.
    Y. Ban and O. Yonemitsu, Tetrahedron 20, 2877 (1964).PubMedCrossRefGoogle Scholar
  35. 31.
    G. Ambady and G. Kartha, J. Crystallogr. Mol. Struct. 3, 37 (1973).CrossRefGoogle Scholar
  36. 32.
    E. S. Visi, L. G. Harsing, J. Gaal, J. Kapocsi, S. Bernath, and G. T. Somogyi, J. Pharmacol. Exp. Ther. 238, 701 (1986);Google Scholar
  37. 32a.
    E. S. Vizi, I. Toth, G. T. Somogyi, L. Szabo, L. G. Harsing, and C. Szantay, J. Med. Chem. 30, 1355 (1987).PubMedCrossRefGoogle Scholar
  38. 33.
    J. R. Huff, P. S. Anderson, J. J. Baldwin, B. V. Clineschmidt, J. P. Guare, V. J. Lotti, D. J. Pettibone, W. C. Randall, and J. P. Vacca, J. Med. Chem. 28, 1759 (1985).CrossRefGoogle Scholar
  39. 34.
    D. J. Pettibone, B. V. Clineschmidt, V. J. Lotti, G. E. Martin, J. R. Huff, W. C. Randall, J. Vacca, and J. J. Baldwin, NS Arch. Pharmacol. 333, 110 (1986).CrossRefGoogle Scholar
  40. 35.
    J. L. Archibald, D. R. Beardsley, T. J. Ward, J. F. Waterfall, and J. F. White, J. Med. Chem. 26, 416 (1983).PubMedCrossRefGoogle Scholar
  41. 36.
    R. P. McAdams and K. F. Rhodes, Br. J. Pharmacol. 79, 308P (1983).Google Scholar
  42. 37.
    Y.-D. Cheung, S. R. Nahorski, K. F. Rhodes, and J. F. Waterfall, Biochem. Pharmacol. 33, 1566 (1984).PubMedCrossRefGoogle Scholar
  43. 38.
    T. A. Crabb, R. F. Nelson, and D. Jackson, Chem. Rev. 71, 109 (1971).CrossRefGoogle Scholar
  44. 39.
    R. D. Clark, D. B. Repke, A. T. Kilpatrick, C. M. Brown, A. C. MacKinnon, R. U. Clague, and M. Spedding, J. Med. Chem. 32, 2034 (1989).PubMedCrossRefGoogle Scholar
  45. 40.
    H. O. Kalkman, E. M. Van Gelderen, P. B. M. W. M. Timmermans, and P. A. Van Zwieten, Eur. J. Pharmacol. 90, 221 (1983).PubMedCrossRefGoogle Scholar
  46. 41.
    V. J. Nickolson and J. H. Wieringa, J. Pharm. Pharmacol. 33, 760 (1981).PubMedCrossRefGoogle Scholar
  47. 42.
    M. Raiteri, G. Maura, A. Gemignani, and A. Pittaluga, NS Arch. Pharmacol. 332, 180 (1983).CrossRefGoogle Scholar
  48. 43.
    J. C. Doxey and A. G. Roach, J. Autonom. Pharmacol. 1, 73 (1980).CrossRefGoogle Scholar
  49. 44.
    P. S. Portoghese, T. N. Riley, and J. W. Miller, J. Med. Chem. 14, 562 (1971).Google Scholar
  50. 45.
    B. Belleau and D. J. Triggle, J. Med. Pharm. Chem. 5, 636 (1962).CrossRefGoogle Scholar
  51. 46.
    R. Howe and B. S. Rao, J. Med. Chem. 11, 1118 (1968).PubMedCrossRefGoogle Scholar
  52. 47.
    C. K. Buckner and P. N. Patil, J. Pharmacol. Exp. Ther. 176, 634 (1971).PubMedGoogle Scholar
  53. 48.
    D. C. Kvam, D. A. Riggilo, and P. M. Lish, J. Pharmacol. Exp. Ther. 149, 183 (1965); P. M. Lish, J. H. Weikel, and K. W. Durgan, J. Pharmacol. Exp. Ther. 161 (1965).PubMedGoogle Scholar
  54. 49.
    L. Almirante and W. Murmann, J. Med. Chem. 9, 650 (1966);PubMedCrossRefGoogle Scholar
  55. 49a.
    G. Fassina, J. Pharm. Pharmacol. 18, 399 (1966).PubMedCrossRefGoogle Scholar
  56. 50.
    V. Erspamer, Nature 169, 375 (1952);PubMedCrossRefGoogle Scholar
  57. 50a.
    T. Kappe and M. D. Armstrong, J. Med. Chem. 7, 569 (1964).PubMedCrossRefGoogle Scholar
  58. 51.
    J. W. Black and J. S. Stephenson, Lancet 11, 311 (1962).CrossRefGoogle Scholar
  59. 52.
    H. Corrodi, H. Persson, A. Carlsson, and J. Roberts, J. Med. Chem. 6, 751 (1963).PubMedCrossRefGoogle Scholar
  60. 53.
    H. H. Harms, Life Sci, 19, 1441 (1976);CrossRefGoogle Scholar
  61. 53a.
    H. H. Harms, J. Zaagsma, and J. De Vente, Life Sci, 21, 123 (1977).PubMedCrossRefGoogle Scholar
  62. 54.
    P. N. Patil, J. Pharmacol. Exp. Ther. 160, 308 (1968).PubMedGoogle Scholar
  63. 55.
    M. Dukes and L. H. Smith, J. Med. Chem. 14, 326 (1971).PubMedCrossRefGoogle Scholar
  64. 56.
    C. Kaiser, T. Jen, E. Garvey, W. D. Bowen, D. F. Coletta, and J. R. Wardell, J. Med. Chem. 20, 687 (1977).PubMedCrossRefGoogle Scholar
  65. 57.
    K. H. Rahn, A. Hawlina, F. Kersting, and G. Planz, NS Arch. Pharmacol. 286, 319 (1974).CrossRefGoogle Scholar
  66. 58.
    K. Stoschitzky et al, NS Arch. Pharmacol. 339, 474 (1989).CrossRefGoogle Scholar
  67. 59.
    K. H. Rahn, Eur. Heart J. 4 (Suppl. D), 27 (1983).PubMedCrossRefGoogle Scholar
  68. 60.
    T. Walle, J. G. Webb, E. E. Bagwell, U. K. Walle, H. B. Daniell, and T. E. Gaffney, Biochem. Pharmacol. 37, 115 (1988).PubMedCrossRefGoogle Scholar
  69. 61.
    D. J. Coltart and D. G. Shand, Br. Med. J. 3, 731 (1970).PubMedCrossRefGoogle Scholar
  70. 62.
    T. Walle, E. C. Conradi, U. K. Walle, T. C. Fagan, and T. E. Gaffney, Clin. Pharmacol. Ther. 27, 22 (1980).PubMedCrossRefGoogle Scholar
  71. 63.
    C. F. George, T. Fenyvesi, M. E. Conolly, and C. T. Dollery, Eur. J. Clin. Pharmacol. 4, 74 (1972).PubMedCrossRefGoogle Scholar
  72. 64.
    S. Ward, R. A. Branch, T. Walle, and U. K. Walle, Pharmacologist 28, 137 (1986).Google Scholar
  73. 65.
    M. S. Lennard, G. T. Tucker, J. H. Silas, S. Freestone, L. E. Ramsay, and H. F. Woods, Clin. Pharmacol. Ther. 34, 732 (1983).PubMedCrossRefGoogle Scholar
  74. 66.
    E. Mutschler, Y. Gietl, D. Krauss, E. Martin, G. Pflugmann, H. Weber, and H. Spahn, in: Chirality and Biological Activity, (B. Holmstedt, H. Frank, and B. Testa, ed.), p. 199, Alan R. Liss, New York (1990).Google Scholar
  75. 67.
    P. Drayer, T. Leemann, A. Kupfer, T. Kronbach, and U.A. Meyer, Eur. J. Pharmacol. 31, 313 (1986).CrossRefGoogle Scholar
  76. 68.
    R. J. Francis, P. B. East, and J. Larman, Eur. J. Clin. Pharmacol. 23, 529 (1982).PubMedCrossRefGoogle Scholar
  77. 69.
    H. P. Ochs, P. Hajdú, and D. J. Greenblatt, Klin. Wochenschr. 64, 636 (1986).PubMedCrossRefGoogle Scholar
  78. 70.
    S. Honma, T. Ito, and A. Kambegawa, Chem. Pharm. Bull. 33, 760 (1985).PubMedCrossRefGoogle Scholar
  79. 71.
    M. Fujimaki, Y. Muraboshi, and H. Hakusui, J. Pharm. Sci. 79, 568 (1990).PubMedCrossRefGoogle Scholar
  80. 72.
    K. O. Borg, E. Carlsson, K. J. Hoffmann, T. E. Johnsson, and H. Thorin, Acta Pharmacol. Toxicol. 36, Suppl. V, 125 (1986).CrossRefGoogle Scholar
  81. 73.
    U. A. Meier, J. Gut, T. Kronbach, C. Skoda, U. T. Meier, and T. Catin, Xenobiotica 16, 449 (1986).PubMedCrossRefGoogle Scholar
  82. 74.
    J. Gut, C. Catin, P. Drayer, T. Kronbach, U. Zanger, and U. A. Meyer, J. Biol. Chem. 261, 1734 (1986).Google Scholar
  83. 75.
    M. S. Lennard, Pharmacol. Ther. 41, 461 (1989).PubMedCrossRefGoogle Scholar
  84. 76.
    U. K. Walle, T. Walle, S. A. Bai, and L. S. Olanoff, Clin. Pharmacol. Ther. 34, 718 (1983).PubMedCrossRefGoogle Scholar
  85. 77.
    L. A. Greene and A. S. Tischler, in: Advances in Cellular Neurobiology (S. Fedoroff and L. Hertz, eds.), p. 373, Academic Press, New York (1982).Google Scholar
  86. 78.
    J. G. Webb, E. E. Bagwell, T. Walle, and T. E. Gaffney, Circulation 74, 11–375 (1986).Google Scholar
  87. 79.
    H. Takahashi, H. Ogata, S. Kanno, and H. Takeuchi, J. Pharmacol. Exp. Ther. 252, 272 (1990).PubMedGoogle Scholar
  88. 80.
    H. Takahashi, S. Kanno, H. Ogata, K. Kashiwada, M. Ohira, and K. Someya, J. Pharm. Sci. 77, 993 (1988).PubMedCrossRefGoogle Scholar
  89. 81.
    T. Walle, Drug Metab. Dispos. 13, 279 (1985).PubMedGoogle Scholar
  90. 82.
    U. K. Walle, H. Thibodeaux, P. J. Privitera, and T. Walle, Chirality, 1, 192 (1989).PubMedCrossRefGoogle Scholar
  91. 83.
    T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc. 102, 5974 (1980).CrossRefGoogle Scholar
  92. 84.
    K. Ko and K. B. Sharpless, J. Org. Chem. 51, 3710 (1986).CrossRefGoogle Scholar
  93. 85.
    J. J. Baldwin, A. W. Raab, K. Mensler, B. H. Arison, and D. E. McClure, J. Org. Chem. 43, 4876 (1978).CrossRefGoogle Scholar
  94. 86.
    D. E. McClure, B. H. Arison, and J. J. Baldwin, J. Am. Chem. Soc. 101, 3666 (1979).CrossRefGoogle Scholar
  95. 87.
    E. C. Baer, Biochem. Prep. 2, 31 (1952).Google Scholar
  96. 88.
    J. C. Danilewicz and J. E. G. Kemp, J. Med. Chem. 16, 168 (1973).PubMedCrossRefGoogle Scholar
  97. 89.
    L. M. Weinstock, D. M. Mulvey, and R. Tull, J. Org. Chem. 41, 3121 (1978).CrossRefGoogle Scholar
  98. 90.
    A.-B. Jeppsson, U. Johansson, and B. Waldeck, Acta Pharmacol. Toxicol. 54, 285 (1984).CrossRefGoogle Scholar
  99. 91.
    B.J. Clark, K. Menninger, and A. Berthilet, Br. J. Clin. Pharmacol. 13, 149 S (1982).CrossRefGoogle Scholar
  100. 92.
    B. G. Main and H. Tucker, Prog. Med. Chem. 22, 122 (1985).Google Scholar
  101. 93.
    T. H. Morris and A. J. Kaumann, NS Arch. Pharmacol. 327, 176 (1984).CrossRefGoogle Scholar
  102. 94.
    J. J. Baldwin and W. B. Abrams, in: Drug Stereochemistry. Analytical Methods and Pharmacology (I. W. Wainer and D. E. Drayer, eds.), p. 311, Dekker, New York (1988).Google Scholar
  103. 95.
    E. Yo, K. Nakagawa, and Y. Hoshino, Chem. Pharm. Bull. 29, 2157 (1981).PubMedCrossRefGoogle Scholar
  104. 96.
    P. J. Machin, D. N. Hurst, and J. M. Osbond, J. Med. Chem. 28, 1648 (1985).PubMedCrossRefGoogle Scholar
  105. 97.
    H. R. Kaplan and M. A. Commarato, J. Pharmacol. Exp. Ther. 185, 395 (1973).PubMedGoogle Scholar
  106. 98.
    B. Waldeck and E. Widmark, Acta Pharmacol. Toxicol. 56, 221 (1985).CrossRefGoogle Scholar
  107. 99.
    A. J. Nichols, A. C. Sulpizio, D. J. Ashton, J. P. Hieble, and R. R. Ruffolo Jr., Chirality 1, 265 (1989).PubMedCrossRefGoogle Scholar
  108. 100.
    J. J. Baldwin, D. E. McClure, D. M. Gross, and M. Williams, J. Med. Chem. 25, 931 (1982).PubMedCrossRefGoogle Scholar
  109. 101.
    M. Bouzoubaa, G. Leclerc, S. Rakhit, and G. Andermann, J. Med. Chem. 28, 896 (1985).PubMedCrossRefGoogle Scholar
  110. 102.
    J. J. Baldwin, W. C. Lumma, G. F. Lundell, G. S. Ponticello, A. W. Raab, E. L. Engelhardt, and R. Hirschmann, J. Med. Chem. 22, 1284 (1979).PubMedCrossRefGoogle Scholar
  111. 103.
    J. Kaiser, Arzneim. Forsch. 30, 427 (1980).Google Scholar
  112. 104.
    U. Johansson, and B. Waldeck, J. Pharm. Pharmacol. 32, 659 (1980).;PubMedCrossRefGoogle Scholar
  113. 104a.
    A. Hedberg, H. Mattisson, and E. Carlsson, J. Pharm. Pharmacol. 32, 660 (1980).PubMedCrossRefGoogle Scholar
  114. 105.
    R. J. Eden, D. A. A. Owen, and E. M. Taylor, Br. J. Pharmacol 78, 34P (1983).Google Scholar
  115. 106.
    J. A. Edwards, B. Berkoz, G. S. Lewis, O. Halpern, J. H. Fried, A. M. Strosberg, L. M. Miller, S. Urich, F. Liu, and A. P. Roszkowski, J. Med. Chem. 17, 200 (1974).PubMedCrossRefGoogle Scholar
  116. 107.
    S. Karhuvaara and T. Kaila, J. Pharm. Pharmacol. 41, 649 (1989).PubMedCrossRefGoogle Scholar
  117. 108.
    J. J. Baldwin, R. Hirschmann, P. K. Lumma, W. C. Lumma, G. S. Ponticello, C. S. Sweet, and A. Scriabine, J. Med. Chem. 20, 1024 (1977).PubMedCrossRefGoogle Scholar
  118. 109.
    W. Wächter, U. Munch, H. Lemoine, and A. J. Kaumann, NS Arch. Pharmacol. 313, 1 (1980).CrossRefGoogle Scholar
  119. 110.
    Anon., Pharm. J., p. 45, July 8, 1989.Google Scholar
  120. 111.
    C. J. Schmitt, D. M. Gross, and N. N. Share, Graefe’s Arch. Clin. Exp. Opthalmol 221, 167 (1984).CrossRefGoogle Scholar
  121. 112.
    W. H. Frishman and R. Silverman, in: Clinical Pharmacology of the Beta-Adrenoceptor Blocking Drugs (W. H. Frishman, ed.), p. 15, Appleton-Century-Crofts, New York (1980).Google Scholar
  122. 113.
    F. T. Fraunfelder and A. F. Barker, New Eng. J. Med. 311, 1441 (1984).PubMedGoogle Scholar
  123. 114.
    A.J. Hutt, Pharm. J. 242, 119 (1989).Google Scholar
  124. 115.
    N. N. Share, V. J. Loti, and P. Gautheron, Graefe’s Arch. Clin. Exp. Ophthalmol. III, 234 (1984).Google Scholar
  125. 116.
    N. Bodor and L. Prokai, Pharm. Res. 7, 723 (1990).PubMedCrossRefGoogle Scholar
  126. 117.
    N. El Tayar, B. Testa, H. Van De Waterbeemd, P.-A. Carrupt, and A.J. Kaumann, J. Pharm. Pharmacol. 40, 609 (1988).PubMedCrossRefGoogle Scholar
  127. 118.
    L. H. Smith, J. Appl. Chem. Biotechnol. 28, 201 (1978).Google Scholar
  128. 119.
    P.J. Machin, D.N. Hurst, R. M. Bradshaw, L. C. Blaber, D. T. Burden, and R. A. Melarange, J. Med. Chem. 11, 503 (1984).CrossRefGoogle Scholar
  129. 120.
    P. B. Woods and M. L. Robinson, J. Pharm. Pharmacol. 33, 172 (1981).PubMedCrossRefGoogle Scholar
  130. 121.
    D. E. McClure, J. J. Baldwin, W. C. Randall, T. F. Lyon, K. Mensler, G. F. Lundell, A. W. Raab, D. Gross, E. A. Risley, C. S. Sweet, and M. Williams, J. Med. Chem. 26, 649 (1983).PubMedCrossRefGoogle Scholar
  131. 122.
    K. Leftheris and M. Goodman, J. Med. Chem. 33, 216 (1990).PubMedCrossRefGoogle Scholar
  132. 123.
    D. E. Nichols, C. F. Barfknecht, D. B. Rusterholz, F. Benington, and R. D. Morin, J. Med. Chem. 16, 480 (1973).PubMedCrossRefGoogle Scholar
  133. 124.
    J. E. Clifton, I. Collins, P. Hallett, D. Hartley, L. H. C. Lunts, and P. D. Wicks, J. Med. Chem. 25, 670 (1982).PubMedCrossRefGoogle Scholar
  134. 125.
    J. A. Dale, D. L. Dull, and H. S. Mosher, J. Org. Chem. 34, 2543 (1969).CrossRefGoogle Scholar
  135. 126.
    G. Brooker, P. Greengard, and G. A. Robinson, Adv. Cyclic Nucleotide Res. 10, 4 (1979).Google Scholar
  136. 127.
    S. M. Celuch, M. L. Dubocovich, and S. Z. Langer, Br. J. Pharmacol. 63, 97 (1978).PubMedCrossRefGoogle Scholar
  137. 128.
    M. Heimburgerm, M. J. Montero, V. Fougères, F. Beslot, M. Davy, M. Midol-Monnet and Y. Cohen, Br. J. Pharmacol. 98, 211 (1989).CrossRefGoogle Scholar
  138. 129.
    H. Tucker, J. Med. Chem. 24, 1364 (1981).PubMedCrossRefGoogle Scholar
  139. 130.
    H. Tucker, J. Med. Chem. 44, 2943 (1979).Google Scholar
  140. 131.
    G. Shtacher, R. Rubinstein, and P. Somani, J. Med. Chem. 21, 678 (1978).PubMedCrossRefGoogle Scholar
  141. 132.
    A.J. Bilski, S. E. Halliday, J. D. Fitzgerald, and J. L. Wale, J. Cardiovasc. Pharmacol. 5, 430 (1983).PubMedCrossRefGoogle Scholar
  142. 133.
    T. L. Lemke, M. B. Cramer, S. W. Adamski, C. A. Pedone, and G. Brooker, J. Med. Chem. 24, 1211 (1981).PubMedCrossRefGoogle Scholar
  143. 134.
    D. J. Dooley, H. Bittiger, and N. C. Reymann, Eur. J. Pharmacol. 130, 137 (1986).PubMedCrossRefGoogle Scholar
  144. 135.
    M. Beer, A. Richardson, J. Poat, L. L. Iversen, and S. M. Stahl, Biochem. Pharmacol. 37, 1145 (1988).PubMedCrossRefGoogle Scholar
  145. 136.
    T. Jen and C. Kaiser, J. Med. Chem. 20, 693 (1977).PubMedCrossRefGoogle Scholar
  146. 137.
    Y. Barrans, M. Cotrait, and J. Dangonmau, Acta Crystallogr. Sect., B 29, 1264 (1973).CrossRefGoogle Scholar
  147. 138.
    R. Howe, B. S. Rao, and M. S. Chodnekar, J. Med. Chem. 13, 169 (1970).PubMedCrossRefGoogle Scholar
  148. 139.
    W. Buchinger et al (7 co-authors), Acta Med. Aust. Suppl. 1, 62 (1988).Google Scholar
  149. 140.
    O. Eber et al., Clin. Endocrinol. 32, 363 (1990).CrossRefGoogle Scholar
  150. 141.
    W. Buchinger, O. Eber, G. Uray, P. Lind, and W. Lindner, Chirality 3, 145 (1991).CrossRefGoogle Scholar
  151. 142.
    L. G. Harsing, Jr. and E. S. Visi, J. Pharmacol. Exp. Ther. 256, 44 (1991).PubMedGoogle Scholar
  152. 143.
    S. A. Weerawarna, S. M. Geisshüsler, S. S. Murthy, and W. L. Nelson, J. Med. Chem. 34, 3091 (1991).PubMedCrossRefGoogle Scholar
  153. 144.
    V. Andrisano, G. Marucci, C. Melchiorre, and V. Tumiatti, Chirality 4, 16 (1992).PubMedCrossRefGoogle Scholar
  154. 145.
    A. M. Vermeulen, F. M. Belpaire, E. Moerman, F. De Smet, and M. G. Bogaert, Chirality 4, 73 (1992).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1993

Authors and Affiliations

  • Alan F. Casy
    • 1
  • George H. Dewar
    • 1
  1. 1.University of BathBathUK

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