Antagonists, Dualists, and Kappa Agonists

  • Alan F. Casy
  • Robert T. Parfitt

Abstract

The aim of this chapter is to bring together data on opioid ligands that (1) antagonize the actions of morphine and its surrogates, (2) possess both agonist and antagonist properties, and (3) possess the unique pharmacological profile of the so-called kappa (κ) agonists. The majority of these compounds fall within the morphine, morphinan, or benzomorphan groups of opioid ligands (Chapters 2, 3, and 4). The topic of narcotic antagonists and dualists has been extensively reviewed up to 1976(1) and only a resumé of the earlier work is presented here.

Keywords

Antinociceptive Action Potent Antagonist Antagonist Property Narcotic Antagonist Kappa Agonist 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    S. Archer and L. S. Harris, Prog. Med. Chem. 8, 262 (1965).Google Scholar
  2. S. Archer and W. F. Michne, Prog. Med. Chem. 20, 45 (1976).Google Scholar
  3. 2.
    L. A. Woods, Pharmacol. Rev. 8, 175 (1956).PubMedGoogle Scholar
  4. K. Unna, J. Pharmacol. Exp. Ther. 79, 27 (1943).Google Scholar
  5. 3.
    J. Weijlad and A. E. Erickson, J. Am. Chem. Soc. 64, 869 (1942).Google Scholar
  6. J. Weijlad and A. E. Erickson, K. Unna, J. Pharmacol Exp. Ther. 79, 27 (1943).Google Scholar
  7. 4.
    H. Schapiro and J. M. Beal, Surgery 34, 870 (1953).PubMedGoogle Scholar
  8. 5.
    Martindale: The Extra Pharmacopoeia, 28th ed., pp. 1002, 1031, The Pharmaceutical Press, London (1982).Google Scholar
  9. 6.
    A. S. Keats and J. C. Mithoefer, Fed. Proc. 14, 356 (1955).Google Scholar
  10. 7.
    L. Lasagna and H. K. Beecher, J. Pharmacol. Exp. Ther. 112, 356 (1954).PubMedGoogle Scholar
  11. 8.
    A. S. Keats and J. Telford, J. Pharmacol. Exp. Ther. 117, 190 (1956).PubMedGoogle Scholar
  12. 9.
    W. R. Martin and C. W. Gorodetzky, J. Pharmacol. Exp. Ther. 150, 437 (1965).PubMedGoogle Scholar
  13. 10.
    A. H. Beckett and A. F. Casy, Prog. Med. Chem. 4, 171 (1965).PubMedGoogle Scholar
  14. 11.
    B. M. Cox and M. Weinstock, Br. J. Pharmacol. 22, 289 (1964).Google Scholar
  15. 12.
    L. Grumback and H. I. Chernov, J. Pharmacol. Exp. Ther. 149, 385 (1965).Google Scholar
  16. 13.
    J. Pearl and L. S. Harris, J. Pharmacol. Exp. Ther. 154, 319 (1960).Google Scholar
  17. J. Pearl, M. D. Aceto, and L. S. Harris, J. Pharmacol. Exp. Ther. 160, 217 (1968).PubMedGoogle Scholar
  18. J. Pearl, H. Stander, and D. B. McKean, J. Pharmacol. Exp. Ther. 167, 9 (1969).PubMedGoogle Scholar
  19. H. Blumberg, P. S. Wolf and H. B. Dayton, Proc. Soc. Exp. Biol Med. 118, 763 (1965).PubMedGoogle Scholar
  20. R. I. Taber, D. D. Greenhouse and S. Irwin, Nature, 204, 189 (1964).PubMedGoogle Scholar
  21. H. O. C. Collier, L. C. Dinneen, C. A. Johnson and C. Schneider, Br. J. Pharmacol. 32, 295 (1968).Google Scholar
  22. 14.
    H. I. Chernov, D. E. Wilson, F. Fowler, and A. J. Plummer, Arch. Int. Pharmacodyn. Ther. 167, 171 (1967).PubMedGoogle Scholar
  23. 15.
    W. L. Dewey and L. S. Harris, J. Pharmacol. Exp. Ther. 179, 652 (1971).Google Scholar
  24. 16.
    S. I. Ankier, R. D. E. Sewell, and P. S. J. Spencer, Eur. J. Pharmacol. 27, 1 (1974).PubMedGoogle Scholar
  25. S. I. Ankier, R. D. E. Sewell, and P. S. J. Spencer, Prog. Med. Chem. 14, 249 (1977).Google Scholar
  26. 17.
    T. D. Perrine, L. Atwell, I. B. Tice, A. E. Jacobson, and E. L. May, J. Pharm. Sci. 61, 86 (1972).PubMedGoogle Scholar
  27. 18.
    H. W. Kosterliz and A. J. Watt, Br. J. Pharmacol. 33, 266 (1968).Google Scholar
  28. H. W. Kosterlitz and A. A. Waterfield, Ann. Rev. Pharmacol. 15, 29 (1975).PubMedGoogle Scholar
  29. 19.
    J. Hughes, H. W. Kosterlitz, and F. M. Leslie, Br. J. Pharmacol. 51, 139 (1974).Google Scholar
  30. 20.
    G. W. Pasternak and S. R. Childers, in: Recent Advances in Clinical Pharmacology (P. Turner and D. G. Shand, eds.), p. 257, Churchill Livingstone, Edinburgh (1983).Google Scholar
  31. 21.
    M. A. Iorio and A. F. Casy, J. Med. Chem. 21, 812 (1978) and refs. cited.PubMedGoogle Scholar
  32. 22.
    I. Monkovic, H. Wong, A. W. Pircio, Y. G. Perron, I. J. Pachter, and B. Belleau, Can. J. Chem. 53, 3094 (1975).Google Scholar
  33. 23.
    S. K. Sharma, M. Nirenberg, and W. A. Klee, Proc. Natl. Acad. Sci. USA 72, 590 (1975).PubMedGoogle Scholar
  34. 24.
    C. A. Winter, P. D. Orahovats, and E. G. Lehman, Arch. Int. Pharmacodyn. Therap. 110, 186 (1957).Google Scholar
  35. R. L. Clark, A. A. Pessolano, J. Weijland, K. Pfister 3rd, J. Am. Chem. Soc. 75, 4963 (1953).Google Scholar
  36. 25.
    G. F. Blane, A. L. A. Boura, A. E. Fitzgerald, and R. E. Lister, Br. J. Pharmacol. 30, 11 (1967).Google Scholar
  37. 26.
    J. W. Lewis, in: Narcotic Antagonists, p. 123 (M. C. Brande, L. S. Harris, E. L. May, J. P. Smith, and J. E. Villareal, eds.), Raven Press, New York (1974).Google Scholar
  38. 27.
    G. F. Blane, A. L. A. Boura, E. C. Leach, W. D. Gray, and A. C. Osterberg, J. Pharm. Pharmacol. 20, 798 (1968).Google Scholar
  39. 28.
    W. F. Michne, R. L. Salsbury, and S. J. Michalec, J. Med. Chem. 20, 682 (1977).PubMedGoogle Scholar
  40. 29.
    A. Cowan, in: Narcotic Antagonists, p. 427 (1974) (see ref. 26).Google Scholar
  41. A. Cowan, J. W. Lewis, and I. R. Macfarlane, Br. J. Pharmacol. 60, 537 (1977).PubMedGoogle Scholar
  42. A. Cowan, J. C. Doxey, and E. J. R. Harry, Br. J. Pharmacol. 60, 547 (1977).PubMedGoogle Scholar
  43. 30.
    J. M. Habrook and M. J. Rance, in: Opiates and Endogenous Opioid Peptides (H. W. Kosterlitz, ed.), p. 295, Elsevier, North-Holland, Amsterdam (1976).Google Scholar
  44. 31.
    S. C. Clarke, D. R. Jasinski, J. S. Pevnick, and J. D. Griffith, Clin. Pharmacol. Ther. 19, 295 (1976).Google Scholar
  45. 32.
    M. P. Kotick, D. L. Leland, J. O. Polazzi, and R. N. Schut, J. Med. Chem. 23, 166 (1980).PubMedGoogle Scholar
  46. 33.
    D. L. Leland and M. P. Kotick, J. Med. Chem. 24, 717 (1981).PubMedGoogle Scholar
  47. 34.
    J. Quick, P. Herihly, R. K. Razdan, and J. F. Howes, J. Med. Chem. 25, 983 (1982).PubMedGoogle Scholar
  48. 35.
    U. Weiss, J. Am. Chem. Soc. 77, 5891 (1955).Google Scholar
  49. 36.
    M. J. Lewenstein, Br. Pat. 955, 493; Chem. Abstr. 61, 4410c (1964).Google Scholar
  50. 37.
    I. Iijima, J. Minamikawa, A. E. Jacobson, A. Brossi, and K. C. Rice, J. Med. Chem. 21, 398 (1978).PubMedGoogle Scholar
  51. 38.
    A. E. Takermori, H. J. Kupferberg, and J. W. Miller, J. Pharmacol. Exp. Ther. 169, 39 (1969).Google Scholar
  52. 39.
    R. J. Kobylecki, R. W. Carling, J. A. H. Lord, C. F. C. Smith, and A. C. Lane, J. Med. Chem. 25, 116 (1982).PubMedGoogle Scholar
  53. 40.
    F. F. Foldes, Med. Clin. N Amer. 48, 421 (1964).PubMedGoogle Scholar
  54. 41.
    F. F. Foldes, M. Schapira, T. A. G. Torda, D. Duncalf, and H. P. Shiftman, Anesthesiology, 26, 320 (1965).PubMedGoogle Scholar
  55. 42.
    L. Lasagna, Proc. Roy. Soc. Med. 58, 978 (1965).PubMedGoogle Scholar
  56. D. R. Jasinksi, W. R. Martin, and C. A. Haertzen, J. Pharmacol. Exp. Ther. 157, 420 (1967).Google Scholar
  57. 43.
    J. Fishman, M. L. Cotter, and B. I. Norton, J. Med. Chem. 16, 556 (1973).PubMedGoogle Scholar
  58. 44.
    H. Blumberg, I. J. Pachter, and Z. Matossian, US Patent 3,332,950 (1967).Google Scholar
  59. 45.
    J. B. Jiang, R. H. Hanson, P. S. Portoghese, and A. E. Takemori, J. Med. Chem. 20, 1100 (1977).PubMedGoogle Scholar
  60. 46.
    J. K. Errick and R. C. Heel, Drugs 26, 191 (1983).PubMedGoogle Scholar
  61. R. R. Miller, Am J. Hosp. Pharm. 37, 942 (1980).PubMedGoogle Scholar
  62. 47.
    E. F. Hahn, J. Fishman, and R. D. Heilman, J. Med. Chem. 18, 259 (1975).PubMedGoogle Scholar
  63. 48.
    N. Chatterjie, C. E. Inturris, H. B. Dayton, and H. Blumberg, J. Med. Chem. 18, 490 (1975).PubMedGoogle Scholar
  64. 49.
    J. M. Fujimoto, J. Pharmacol. Exp. Ther. 168, 180 (1969).PubMedGoogle Scholar
  65. J. M. Fujimoto, Proc. Soc. Exp. Med. Biol 133, 317 (1970).Google Scholar
  66. 50.
    E. J. Cone, C. W. Gorodetsky, and S. Y. Yeh, J. Pharm. Sci. 64, 618 (1975).PubMedGoogle Scholar
  67. 51.
    R. J. Sime, M. Dobler, and R. L. Sime, Acta Crystallog. B32, 809 (1976).Google Scholar
  68. 52.
    G. W. Pasternak and E. F. Hahn, J. Med. Chem. 23, 674 (1980).PubMedGoogle Scholar
  69. G. W. Pasternak, S. R. Childers, and S. H. Snyder, J. Pharmacol. Exp. Ther. 214, 455 (1980).PubMedGoogle Scholar
  70. G. S. F. Ling, K. Spiegel, S. L. Nishimura, and G. W. Pasternak, Eur. J. Pharmacol. 86, 487 (1983).PubMedGoogle Scholar
  71. 53.
    E. F. Hahn, M. Carroll-Buatti, and G. W. Pasternak, J. Neuroscience 2, 572 (1982).Google Scholar
  72. E. F. Hahn and G. Pasternak, Life Sci. 31, 1385 (1982).PubMedGoogle Scholar
  73. 54.
    K. Fromherz and B. Pellmount, Experientia 8, 394 (1952).PubMedGoogle Scholar
  74. J. Hellerbach, A. Griissner, and O. Schneider, Helv. Chim. Acta 39, 429 (1956).Google Scholar
  75. 55.
    A. S. Keats, private communication.Google Scholar
  76. 56.
    W. Leimgruber, E. Mohacsi, H. Baruth, and L. O. Randall, in: Narcotic Antagonists, p. 48 (1974) (see réf. 26).Google Scholar
  77. L. Lasagna, Proc. Roy. Soc. Med. 58, 978 (1965).PubMedGoogle Scholar
  78. 57.
    W. W. White, R. Megirian, and P. S. Marcus, Proc. Soc. Exp. Biol. Med. 92, 512 (1956).PubMedGoogle Scholar
  79. 58.
    J. O. Polazzi, R. M. Schut, M. P. Kotick, J. F. Howes, P. F. Osgood, R. K. Razdan, and J. E. Villareal, J. Med. Chem. 23, 174 (1980).PubMedGoogle Scholar
  80. D. L. Leland and M. P. Kotick, J. Med. Chem. 23, 1427 (1980).PubMedGoogle Scholar
  81. 59.
    M. Gates and W. G. Webb, J. Am. Chem. Soc. 80, 1186 (1958).Google Scholar
  82. 60.
    M. Gates and T. A. Montzka, J. Med. Chem. 7, 127 (1964).PubMedGoogle Scholar
  83. 61.
    B. Belleau, in: Chemical Regulation of Biological Mechanisms (A. M. Creighton and S. Turner, eds.), p. 200, Royal Society of Chemistry, London (1982).Google Scholar
  84. Y. Lambert, J.-P. Daris, I. Monkovic and A. W. Pircio, J. Med. Chem. 21, 423 (1978).PubMedGoogle Scholar
  85. 62.
    I. Monkovic, T. T. Conway, H. Wong, Y. G. Perron, I. J. Pachter, and B. Belleau, J. Am. Chem. Soc. 95, 7910 (1973).PubMedGoogle Scholar
  86. I. Monkovic, H. Wong, B. Belleau, I. J. Pachter, and Y. G. Perron, Can. J. Chem. 53, 2515 (1975).Google Scholar
  87. 63.
    I. Monkovic, H. Wong, A. W. Pircio, Y. G. Perron, I. J. Pachter, and B. Belleau, Can. J. Chem. 53, 3094 (1975).Google Scholar
  88. 64.
    F. S. Caruso, A. W. Pircio, H. Madissoo, R. D. Smythe, and I. J. Pachter, in: Pharmacological and Biochemical Properties of Drug Substances (M. E. Goldberg, ed.), Vol 2, p. 19, American Pharmaceutical Association, Washington, D. C. (1979).Google Scholar
  89. 65.
    M. Gordon, J. J. Lafferty, D. H. Tesdeschi, N. B. Eddy, and E. L. May, Nature 192, 1089 (1961).PubMedGoogle Scholar
  90. 66.
    S. Archer, N. F. Albertson, L. S. Harris, A. K. Pierson, J. G. Bird, A. S. Keats, J. Telford, and C. Papadopoulos, Science 137, 541 (1962).PubMedGoogle Scholar
  91. 67.
    G. W. Pasternak, M. Carroll-Bua Hi, and K. Spiegel, J. Pharmacol. Exp. Ther. 219,192 (1981).Google Scholar
  92. 68.
    Anon, Drugs, Basel 5 (1973).Google Scholar
  93. 69.
    N. F. Albertson, in: Narcotic Antagonists, p. 76 (1974), (see ref. 26).Google Scholar
  94. 70.
    N. F. Albertson, J. Med. Chem. 18, 619 (1975).PubMedGoogle Scholar
  95. 71.
    M. Saucier, J.-P. Daris, Y. Lambert, I. Monkovic, and A. W. Pircio, J. Med. Chem. 20, 676 (1977).PubMedGoogle Scholar
  96. 72.
    W. F. Michne and N. F. Albertson, J. Med. Chem. 15, 1278 (1972).PubMedGoogle Scholar
  97. 73.
    J. J. Fanley and J. B. Lapidus, J. Med. Chem. 16, 181 (1973).Google Scholar
  98. 74.
    F. H. Clarke, R. T. Hill, J. K. Saelens, and N. Yokoyama, in: Narcotic Antagonists, p. 81 (1974), (see ref. 26).Google Scholar
  99. 75.
    S. Archer, N. F. Albertson, L. S. Harris, A. K. Pierson, and J. G. Bird, J. Med. Chem. 7, 123 (1964).PubMedGoogle Scholar
  100. 76.
    A. de Meijere, Angew. Chem. Int. Ed. Engl. 18, 809 (1979).Google Scholar
  101. 77.
    B. C. Joshi, C. F. Chignell, and E. L. May, J. Med. Chem. 8, 694 (1965).Google Scholar
  102. K. C. Rice, W. A. Klee, M. D. Aceto, H. H. Swain, and A. E. Jacobson, J. Pharm. Sci. 66, 193 (1977).PubMedGoogle Scholar
  103. 78.
    M. Gordon, J. J. Lafferty, D. H. Tedeschi, B. M. Sutton, N. B. Eddy, and E. L. May, J. Med. Pharm. Chem. 5, 633 (1962).PubMedGoogle Scholar
  104. 79.
    H. Merz, A. Langbein, K. Stockhaus, G. Walter, and H. Wick, in: Narcotic Antagonists, p. 91 (1974), (see ref. 26).Google Scholar
  105. 80.
    H. Merz, K. Stockhaus, and H. Wick, J. Med. Chem. 18, 996 (1975).PubMedGoogle Scholar
  106. H.
    Merz, K. Stockhaus, and H. Wick, 20, 844 (1977).Google Scholar
  107. 81.
    E. L. May and N. B. Eddy, J. Med. Chem. 9, 851 (1966).PubMedGoogle Scholar
  108. 82.
    J. H. Ager, A. E. Jacobson, and E. L. May, J. Med. Chem. 12, 288 (1969).PubMedGoogle Scholar
  109. E. L. May and M. Takeda, J. Med. Chem. 13, 805 (1970).PubMedGoogle Scholar
  110. 83.
    W. F. Michne, J. Med. Chem. 21, 1323 (1978).Google Scholar
  111. 84.
    W. F. Michne, R. T. Lewis, S. J. Michalec, A. K. Pierson, and F. J. Rosenberg, J. Med. Chem. 22, 1158 (1979).PubMedGoogle Scholar
  112. 85.
    P. Osei-Gyimah, S. Archer, M. G. C. Gillan, and H. W. Kosterlitz, J. Med. Chem. 24, 212 (1981).PubMedGoogle Scholar
  113. 86.
    H. Schmidhammer, A. E. Jacobson, L. Atwell, and A. Brossi, Heterocycles 16, 1859 (1981); A. E. Jacobson, private communication.Google Scholar
  114. 87.
    D. L. Lattin, B. Caviness, R. G. Hudson, D. L. Greene, P. K. Raible, and J. B. Richardson, J. Med. Chem. 24, 903 (1981).PubMedGoogle Scholar
  115. 88.
    A. F. Casy, A. B. Simmonds, and D. Staniforth, J. Pharm. Pharmacol, 20, 768 (1968); D. Staniforth and A. F. Casy, unpublished results.PubMedGoogle Scholar
  116. 89.
    T. Oh-Ishi and E. L. May, J. Med. Chem. 16, 1376 (1973).Google Scholar
  117. 90.
    H. W. Kosterlitz, F. M. Leslie, and A. A. Waterfield, J. Pharm. Pharmacol. 27, 73 (1975).PubMedGoogle Scholar
  118. 91.
    A. Langbein, H. Merz, K. Stockhaus, and H. Wick, in: Narcotic Antagonists, p. 157 (1974) (see ref. 26).Google Scholar
  119. 92.
    H. H. Ong, T. Oh-Ishi, and E. L. May, J. Med. Chem. 17, 133 (1974).PubMedGoogle Scholar
  120. 93.
    H. Tecle and G. Hite, Proc. 38th Ann. Sci. Meet. Committee on Problems of Drug Dependence, p. 464 (1976).Google Scholar
  121. 94.
    D. M. Zimmerman, R. Nickander, J. S. Horng, and D. T. Wong, Nature, 275, 332 (1978).PubMedGoogle Scholar
  122. 95.
    M. A. Iorio and A. F. Casy, J. Pharm. Pharmacol. 27, 140 (1975).PubMedGoogle Scholar
  123. M. A. Iorio and A. F. Casy, J. Med. Chem. 21, 812 (1978).PubMedGoogle Scholar
  124. 96.
    F. R. Ahmed, M. A. Iorio, and A. F. Casy, J. Pharm. Pharmacol. 35, 765 (1983).Google Scholar
  125. 97.
    R. L. Clarke, A. J. Gambino, A. K. Pierson, and S. J. Daum, J. Med. Chem. 21, 1235 (1978).PubMedGoogle Scholar
  126. 98.
    R. E. Bowman, H. O. J. Collier, I. M. Lockhart, C. Schneider, N. E. Webb, and M. Wright, J. Med. Chem. 16, 1177 (1973).PubMedGoogle Scholar
  127. 99.
    M. Takeda, H. Inoue, K. Noguchi, Y. Honma, M. Kawamori, G. Tsukamoto, Y. Yamawaki, S. Saito, K. Aoe, T. Date, S. Nurimoto, and G. Hayashi, J. Med. Chem. 20, 221 (1977).PubMedGoogle Scholar
  128. 100.
    J. L. Malis, M. E. Rosenthale, and M. I. Gluckman, J. Pharmacol Exp. Ther. 194, 488 (1975).PubMedGoogle Scholar
  129. 101.
    J. P. Yardley, H. Fletcher, and P. B. Russell, Experientia 34, 1124 (1978).PubMedGoogle Scholar
  130. 102.
    D. della Bella, V. Ferrari, V. Frigeni, and P. Lualdi, Nature New Biol 241, 282 (1973).PubMedGoogle Scholar
  131. 103.
    C. B. Pert, D. L. Bowie, A. Pert, J. L. Morell, and E. Gross, Nature 269, 73 (1977).PubMedGoogle Scholar
  132. 104.
    E. F. Hahn, J. Fishman, Y. Shiwaku, F. F. Foldes, H. Nagashima, and D. Duncalf, Res. Comm. Chem. Path. Pharmacol. 18, 1 (1977).Google Scholar
  133. 105.
    P. Belton, R. Cotton, M. B. Giles, J. J. Gormley, L. Miller, J. S. Shaw, D. Timms, and A. Wilkinson, Life Sci. 33, Sup. J, 443 (1983).PubMedGoogle Scholar
  134. 106.
    P. E. Gilbert and W. R. Martin, J. Pharmacol. Exp. Ther. 198, 66 (1976).PubMedGoogle Scholar
  135. 107.
    D. Romer, H. Buscher, R. C. Hill, R. Maurer, T. J. Petcher, H. B. A. Welle, H. C. C. K. Bakel, and A. M. A. Kerman, Life Sci. 27, 971 (1980).PubMedGoogle Scholar
  136. 108.
    H. H. Swain and M. H. Seevers in Addendum to the 1974 Proc. Comm. Problems of Drug Dependence, p. 1168, National Academy of Science, Washington, D. C. (1974).Google Scholar
  137. 109.
    J. H. Woods, C. B. Smith, F. Medzihradsky, and H. H. Swain, in: Mechanisms of Pain and Analgesic Compounds (R. F. Beers and E. G. Bassett, eds.), p. 4, Raven Press, New York (1979).Google Scholar
  138. 110.
    D. Romer, R. Maurer, and R. C. Hill, paper presented to a symposium on Kappa receptors and their ligands, Faculty of Pharmacy, Toulouse, April 1982.Google Scholar
  139. 111.
    T. Oka, K. Negishi, S. Mitsuaki, T. Matsumiya, T. Inazu, and M. Ueki, Eur. J. Pharmacol. 73, 235 (1981).PubMedGoogle Scholar
  140. 112.
    H. Merz, A. Langbein, K. Stockhaus, and H. Wick, Adv. Biochem. Psychopharmacol. 8, 91 (1974).Google Scholar
  141. 113.
    J. A. H. Lord, A. A. Waterfield, J. Hughes, and H. W. Kosterlitz, Nature 267, 495 (1977).PubMedGoogle Scholar
  142. 114.
    H. W. Kosterlitz, S. J. Paterson, and L. E. Robson, Br. J. Pharmacol. 73, 939 (1981).PubMedGoogle Scholar
  143. 115.
    H. B. A. Welle, private communication; Dutch Patent Application 7804509.Google Scholar
  144. 116.
    H. Merz and K. Stockhaus, J. Med. Chem. 22, 1475 (1979).PubMedGoogle Scholar
  145. 117.
    H. Merz, paper presented at Toulouse symposium (1982), (see ref. 110).Google Scholar
  146. 118.
    J. Szmuszkovicz and P. F. Von Voigtlander, J. Med. Chem. 25, 1125 (1982).PubMedGoogle Scholar
  147. P. F. Von Voigtlander, R. A. Lahti, and J. H. Ludeus, J. Pharmacol. Exp. Ther. 224, 7 (1983).Google Scholar
  148. 119.
    N. J. Harper, G. B. A. Veitch, and D. G. Wibberley, J. Med. Chem. 17, 1118 (1974).Google Scholar
  149. 120.
    D. Romer, H. H. Buscher, R. C. Hill, R. Maurer, T. J. Petcher, H. Zengner, W. Benson, E. Finner, W. Milkowski, and P. W. Thies, Nature 298, 759 (1982).PubMedGoogle Scholar
  150. D. Romer, H. H. Buscher, R. C. Hill, R. Maurer, T. J. Petcher, H. Zengner, W. Benson, E. Finner, W. Milkowski, and P. W. Thies, Life Sci. 31, 1217 (1982).PubMedGoogle Scholar
  151. 121.
    C. Chavkin, I. F. James, and A. Goldstein, Science 215, 413 (1982).PubMedGoogle Scholar
  152. 122.
    A. D. Corbett, S. J. Paterson, A. T. McKnight, J. Magnan, and H. W. Kosterlitz, Nature 299, 79 (1982).PubMedGoogle Scholar
  153. 123.
    S. J. Ward, A. K. Pierson, and W. F. Michne, Life Sci. 33, Suppl. 303 (1983).PubMedGoogle Scholar
  154. W. F. Michne, R. T. Lewis, S. J. Michalec, A. K. Pierson, and F. J. Rosenberg, J. Med. Chem. 22, 1158 (1979).PubMedGoogle Scholar
  155. 124.
    M. Erez, A. E. Takemori, and P. S. Portoghese, J. Med. Chem. 25, 847 (1982).PubMedGoogle Scholar
  156. 125.
    M. S. Gold, C. A. Dackis, A. L. C. Pottash, H. H. Sternbach, and W. J. Anitto, Med. Res. Revs. 2, 211 (1982).Google Scholar
  157. 126.
    A. E. Takemori, in: Narcotic Antagonists, p. 335 (1974), (see ref. 26).Google Scholar
  158. 127.
    A. E. Jacobson, B. S. Bajwa, R. A. Streaty, W. A. Klee, and K. C. Rice, Life Sci. 33, Suppl. 1,159 (1983).Google Scholar
  159. 128.
    P. R. Crabbendam, H. C. Beyerman, T. S. Lie, and L. Maat, Recl. Trav. Chim. Pays-Bas, 102, 135 (1985).Google Scholar
  160. 129.
    G. Toth, M. Kramer, F. Sirokman, A. Borsodi, and A. Ronai, J. Label, Comp. Radiopharm. 19, 1021 (1982).Google Scholar
  161. 130.
    S. Galetta, G. S. F. Ling, L. Wölfin, and G. W. Pasternak, Life Sci. 31, 1389 (1982).PubMedGoogle Scholar
  162. 131.
    V. M. Kolb and J. R. Gober, Life Sci. 33, Suppl. 1, 419 (1983).PubMedGoogle Scholar
  163. 132.
    J. Telford, C. N. Papadopoulos, and A. S. Keats, J. Pharmacol Exp. Ther. 133, 106 (1961).PubMedGoogle Scholar
  164. 133.
    E. Waldmann and P. A. L. Horsfall, Br. Med. J. 1, 642 (1977).PubMedGoogle Scholar
  165. 134.
    P. Y. Law, D. S. Horn, and H. H. Loh, Molec. Pharmacol 23, 26 (1983).Google Scholar
  166. 135.
    E. L. Eliel, S. Morris-Natschke, and V. M. Kolb, Org. Magn. Resort. 22, 258 (1984).Google Scholar
  167. 136.
    E. Hazum, J. J. Sabatka, K.-I. Chang, D. A. Brent, and J. W. Findlay, Science 213, 1010 (1981).PubMedGoogle Scholar
  168. C. Zioudron, R. A. Streaty, and W. A. Klee, J. Biol Chem. 254, 2556 (1979).Google Scholar
  169. 137.
    J. H. Boublik, M. J. Quinn, J. A. Clements, A. C. Herington, K. N. Wynne, and J. W. Funder, Nature 301, 246 (1983).PubMedGoogle Scholar
  170. 138.
    N. Upton, R. D. E. Sewell, and P. S. J. Spencer, IRCS Med. Sci. 9, 614 (1981).Google Scholar
  171. 139.
    R. D. E. Sewell and N. Upton, Br. J. Pharmacol. 80, 558P (1983).Google Scholar
  172. 140.
    D. Romer, private communication.Google Scholar
  173. 141.
    H. Merz, in: X-Ray Crystallography and Drug Action (A. S. Horn and C. J. De Ranter, eds.), p. 302, Clarendon Press, Oxford (1984).Google Scholar
  174. 142.
    S. R. Childers, J. Pharmacol Exp. Ther. 230, 684 (1984).PubMedGoogle Scholar
  175. 143.
    R. Dixon, J. Hsiao, W. Taaffe, E. Hahn, and R. Tuttle, J. Pharm. Sci. 73, 1645 (1984).PubMedGoogle Scholar
  176. 144.
    J. Knoll, S. Furst, and S. Marklett, Arch. Int. Pharmacodyn. Ther. 228, 268 (1977).PubMedGoogle Scholar
  177. 145.
    L. Kerecsen and J. Knoll, Pharmacology 22, 8 (1981).PubMedGoogle Scholar
  178. 146.
    S. J. Ward, A. K. Pierson, and W. F. Michne, paper presented at INRC meeting, Cambridge, UK (July 1984).Google Scholar
  179. 147.
    P. S. Portoghese and A. E. Takemori, paper presented at INRC meeting, Cambridge UK (July 1984).Google Scholar
  180. 148.
    T.-P. Su, T. H. Clements and C. W. Gorodetzki, Life Sci. 28, 2519 (1981).PubMedGoogle Scholar
  181. 149.
    H. W. Kosterlitz, A. A. Waterfield, and V. Berthoud, in: Narcotic Antagonists, p. 319 (1974) (see ref. 26 for details).Google Scholar
  182. 150.
    A. D. Corbett, M. G. C. Gillan, H. W. Kosterlitz, A. T. McKnight, S. J. Paterson, and L. E. Robson, Br. J. Pharmacol. 83, 271 (1984).PubMedGoogle Scholar
  183. 151.
    L. E. Robson, R. W. Foote, R. Maurer, and H. W. Kosterlitz, Neurosci. 12, 621 (1984).Google Scholar
  184. 152.
    P. S. Portoghese and A. E. Takemori, in: Chemical Regulation of Biological Mechanisms (A. M. Creighton and S. Turner, eds.), p. 181, Royal Society of Chemistry, London (1982).Google Scholar
  185. 153.
    S. J. Ward and A. E. Takemori, J. Pharmacol Exp. Ther. 224, 525 (1983).PubMedGoogle Scholar
  186. 154.
    S. J. Ward, private communication.Google Scholar
  187. 155.
    R. A. Olofson, R. C. Schnur, L. Bunes, and J. P. Pepe, Tetrahedron Lett. 1567 (1977).Google Scholar
  188. 156.
    E. R. Garrett and V. R. Chandran, J. Pharm. Sci. 74, 515 (1985).PubMedGoogle Scholar
  189. 157.
    E. J. Cone, C. W. Gorodetzky, W. D. Darwin, and W. F. Buchwald, J. Pharm. Sci. 73, 243 (1984).PubMedGoogle Scholar
  190. 158.
    E. R. Garrett and A. El-Koussi, J. Pharm. Sci. 74, 50 (1985).PubMedGoogle Scholar
  191. 159.
    M. D. Aceto, E. L. May, L. S. Harris, A. E. Jacobson, and H. Awaya, J. Pharm. Sci. 73, 1864 (1984).PubMedGoogle Scholar
  192. 160.
    S. Archer, A. Seyed-Mozaffori, S. Ward, H. W. Kosterlitz, S. J. Paterson, A. T. McNight, and A. D. Corbett, J. Med. Chem. 28, 947 (1985).Google Scholar
  193. 161.
    G. W. Kirby and D. McLean, J. Chem. Soc. Perkin Trans I, 1443 (1985) and references there cited.Google Scholar

Copyright information

© Springer Science+Business Media New York 1986

Authors and Affiliations

  • Alan F. Casy
    • 1
  • Robert T. Parfitt
    • 1
    • 2
  1. 1.University of BathBathUK
  2. 2.Canberra College of Advanced EducationBelconnenAustralia

Personalised recommendations