Rational drug design and the discovery of the Δ2-1,2,3-triazolines, a unique class of anticonvulsant and antiischemic agents

Current Medicinal Chemistry

Volumn 10, Issue 20, 2003, Pages 2081-2108

  Kadaba, Pankaja K ^a  

^a K and K Biosciences Inc   (United States)

Author keywords

1 2 3 Triazolines; Antiischemic agents; Epilepsy; Excitatory amino acid; Glutamate; Stroke

Indexed keywords

1 (4 CHLOROPHENYL) 4,5 DIHYDRO 5 (4 PYRIDYL) 1H 1,2,3 TRIAZOLE; ADD 61060; ADD 95032; AMINOALCOHOL; ANTICONVULSIVE AGENT; AZIRIDINE DERIVATIVE; CALCIUM ION; CHLORIDE CHANNEL; CHLORIDE ION; DIZOCILPINE; DRUG METABOLITE; ETHOSUXIMIDE; EXCITATORY AMINO ACID; GLUTAMIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; NEW DRUG; PHENOBARBITAL; PHENYTOIN; POTASSIUM ION; PRODRUG; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; VALPROIC ACID;

ANTICONVULSANT ACTIVITY; AREA UNDER THE CURVE; ATAXIA; BINDING SITE; BRAIN ISCHEMIA; CEREBROVASCULAR ACCIDENT; CHANNEL GATING; CHEMICAL REACTION; COMPLEX PARTIAL SEIZURE; DOSE RESPONSE; DRUG BINDING; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DESIGN; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG HYDROXYLATION; DRUG MECHANISM; DRUG METABOLISM; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; EXPERIMENTAL MODEL; GAIT DISORDER; IN VITRO STUDY; IN VIVO STUDY; INHIBITION KINETICS; KIDNEY DISEASE; LIVER DISEASE; MUSCLE DISEASE; NERVE CELL NECROSIS; NEUROLOGIC DISEASE; NEUROTRANSMISSION; NONHUMAN; POSTSYNAPTIC INHIBITION; PRESYNAPTIC INHIBITION; PROTEIN SECRETION; REVIEW; SPLEEN DISEASE; STOMACH DISEASE; URINALYSIS;

ANIMALS; ANTICONVULSANTS; BRAIN ISCHEMIA; CEREBROVASCULAR ACCIDENT; DRUG DESIGN; EPILEPSY; HUMANS; PHARMACOKINETICS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 0141426709     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033456765     Document Type: Review

References (113)

1. Kadaba, P.K. Drugs of the Future, 1990, 15, 1013-1024
2. Kadaba, P.K. U.S. Patent Applcn. Filed Nov. 2, 2001.
3. Porter, R.J.; Cereghino, J.J.; Gladding, G.D.; Hessie, B.J.; Kupferberg, H.J.; Scoville, B.; White, B.G. Cleve. Clin. Q., 1984, 51, 293-305.
4. Porter, R.J.; Pitlick, W.H. In Basic and Clinical Pharmacology; Fourth Edn.; B.G. Katzung, Ed.; Appleton and Lange: C.A., 1989; pp.287-303..
5. Rogawski, M.A.; Porter, R.J. Pharmacol Rev., 1990, 42, 223-286. Gumnit, R.J. Ed.; The Epilepsy Handbook: The Practical management of Seizures, 2nd Ed.; Rowen Press: New York, 1995.
6. Dichter, M.A. Epilepsia, 1989, 30, S3-S12.
7. McCulloch, J.; Bullock, R.; Teasdale, G.M. In Frontiers in Pharmacology and Therapeutics: Excitatory Amino Acid Antagonists; B.S. Meldrum, Ed.; Blackwell Scientific Publishers: Oxford, U.K., 1991; pp. 287-326.
8. Choi, D.W.; Rothman, S.M. Ann. Rev. Neurosci., 1991, 13, 171-182.
9. Takagi, K.; Ginsberg, M.D.; Globus, M.Y.T.; Dietrich, W.D.; Martinez, E.; Kraydich, S.; Busto, R. J. Cereb. Blood Flow Metab., 1993, 13, 575-585.
10. Graham, S.H.; Chen, J.; Sharp, F.R.; Simon, R.P. J. Cereb. Blood Flow Metab., 1993, 13, 88-97.
11. Muir, K.W.; Lees, K.R. Stroke, 1995, 26, 503-513.
12. Kadaba, P.K.; Stanovnik, B.; Tisler, M. Adv. Heterocycl. Chem., 1984, 37, 217-349.
13. Kadaba, P.K.; U.S. Patent 4 511 572, 1985.
14. Kadaba, P.K. U.S. Patent 4 618 681, 1986.
15. Kadaba, P.K. U.S. Patent 4 689 334, 1987.
16. Kadaba, P.K. U.S. Patent 4 820 721, 1989.
17. Kadaba, P.K. J. Pharm. Sci., 1984, 73, 850-852.
18. Kadaba, P.K. J. Med Chem., 1988, 31, 196-203.
19. Kadaba, P.K. Biomed & Pharmacother., 1996, 50, 163-169.
20. Kupferberg, H.J. Epilepsia, 1989, 30, S51-56.
21. Kadaba, P.K. J. Pharm. Sci., 1970, 59, 1190-1191.
22. Kadaba, P.K. Pestic. Sci., 1974, 5, 255-258.
23. Kadaba, P.K.; Slevin, J.T. Epilepsia, 1988, 29, 330-337.
24. Scheiner, P. In Selective Organic Transformations, Vol I; B.S. Thyagarajan, Ed.; Wiley Interscience: New York, 1970; pp. 328-362.
25. Chow, A.H.L.; Chiu, F.C.K.; Damani, L.A.; Kadaba, P.K. Pharmacent. Res., 1996, 13, 179-182.
26. Dermer, O.C.; Ham, G.E. (Eds); Ethylenimine and other Aziridines, Academic Press: New York, 1969.
27. Testa, B.; Jenner, P. (Eds); Drug Metabolism: Chemical and Biochemical Aspects, Marcel Dekker: New York, 1976.
28. Gilchrist, T.L.; Gymer, G.E. Adv. Heterocycl. Chem., 1974, 16, 33.
29. Cotman, C.W.; Bridges, R.J.; Taube, J.S.; Clark, A.S.; Geddes, J.W.; Monaghan, D.T. J. NIH Res., 1989, 1, 65-75.
30. Enna, S.J. Annu. Rep. Med. Chem., 1979, 14, 41-50.
31. Fagg, G.E.; Foster, A.C. Neuroscience, 1983, 9, 701-19.
32. Kogure, K. In Neurotransmitters, Focus on Excitatory Amino Acids; I. Kanazawa, Ed.; Excerpta. Medica: Japan, 1988; pp. 95-116.
33. Johnson, G. Annu. Rep. Med. Chem., 1989, 24, 41-50.
34. Fisher, R.S.; Coyle, J.T. (Eds); Neurotransmitters and Epilepsy; Wiley-Liss: New York, 1991.
35. Fonnum, F. Ed., Amino Acids as Chemical Transmitters; Plenum Press: New York, 1978.
36. Meldrum, B.S.; Chapman, A.G. In Glutamine, Glutamate and GABA in the Central Nervous System; L: Hertz, et al. Eds; Alan R. Liss, Inc: New York, 1983, pp. 625-641.
37. Van Gelder, N.M.; Courtois, A. Brain Res., 1972, 43, 477-484.
38. Bradford, H.F.; Dodd, P.R. Biochem. Pharmacol., 1977, 26, 253-254.
39. Dodd, P.R.; Bradford, H.F.; Abdul-Ghani, A.S.; Cox, D.W.G.; Coutinho-Netto, J. Brain Res., 1980, 193, 505-517.
40. Watkins, J.C.; Evans, R.H. Annu. Rev. Pharmacol. Toxicol, 1981, 21, 165-204.
41. Coutinho-Netto, J.C.; Abdul-Ghani, A.S.; Collins, J.F.; Bradford, H.F. Epilepsia, 1981, 22, 289-296.
42. Cruczwar, S.J.; Meldrum, B.S. Eur. J. Pharmacol., 1982, 83, 335-338.
43. Croucher, M.J.; Collins, J.F.; Meldrum, B.S. Science, 1982, 216, 899-901.
44. Peterson, D.W.; Collins, J.F.; Bradford, H.F. In Glutamine, Glutamate and GABA in the Central Nervous System; L. Hertz, et al. Eds; Alan R. Liss, Inc.: New York, 1983, pp. 643-652.
45. Schwarcz, R.; Ben-Ari, Y., (Eds); Excitatory Amino Acids and Epilepsy; Plenum Press: New York 1986.
46. Kadaba, P.K. Tetrahedron, 1969, 25, 3053-3066.
47. Kadaba, P.K. Synthesis, 1973, 71-84.
48. Kadaba, P.K. Tetrahedron, 1966, 22, 2453-2460.
49. Kadaba, P.K. J. Heterocycl. Chem., 1975, 12, 143-146.
50. Kadaba, P.K.; Fannin, N.F. J. Heterocycl. Chem., 1967, 4, 301-304.
51. Huisgen, R. Angew. Chem. (Intnl Ed), 1963, 2, 565; 1963, 2, 633.
52. Kadaba, P.K.; Edwards, J.O. J. Org. Chem., 1961, 26, 2331-2335.
53. Elderfield, R.C. Ed. Heterocyclic Chemistry, vol. 5, Wiley: New York, 1957.
54. Zollinger, H. Azo and Diazo Chemistry, Interscience: New York, 1961.
55. Wolff, L. Liebigs Ann., 1912, 394, 23-68.
56. Wolff, L. Liebigs Ann., 1913, 399, 274.
57. Alder, K.; Stein, G. Liebigs Ann., 1931, 485, 211.
58. Alder, K.: Stein, G. Liebigs Ann., 1933, 501, 1.
59. Kadaba, P.K.; Stevenson, P.J.; Nnane I.P.; Damani, L.A. Bioorg. Med. Chem., 1996, 4, 165-178.
60. Swinyard, E.A.; Sofia, R.D.; Kupferberg, H.J. Epilepsia, 1986, 27, 27-34.
61. Nicholls, D.; Attwell, D. Trends Pharmacol. Sci., 1990, 11, 462-468.
62. Choi, D.W. Cerebrovas. Brain Metab. Revs., 1990, 2, 105.
63. Potashner, S.J. J. Neurochem., 1979, 32, 103-109.
64. Kadaba, P.K.; Slevin, J.T. Pharmaceut. Res., 1989, 6, S-42.
65. McNamara, J.O.; Bonhaus, D.W.; Shin, C.; Crain, B.J.; Gellman, R.L.; Giacchino, J.L. CRC Crit. Rev. Neurobiol., 1985, 1, 341-391.
66. Wada, J.A. (Ed.); Kindling III, Raven Press: New York, 1986.
67. Loscher, W.; Schmidt, D. Epilepsy Res., 1988, 2, 145-181.
68. Penry, J.K.; Daly, D.D. Adv. Neurol., 11, Raven Press: New York, 1975.
69. McNamara, J.O.; Russell, R.D.; Rigsbee, L.; Bonhaus, D.W. Neuropharmacol., 1988, 27, 563-568.
70. McNamara, J.O. Epilepsia, 1989, 30, S13-18.
71. McNamara, J.O.; Rigsbee, L.C.; Butler, L.S.; Shin, C. Ann. Neurol., 1989, 26, 675-678.
72. Tita, T.; Kadaba, P.K.; Crooks, P.A. J. Biopharm. Sci., 1990, 1, 171-180.
73. Tita, T.; Kadaba, P.K.; Slevin, J.T.; Deshmukh, T.R. Pharmaceut. Res., 1991, 5, S269.
74. Stevenson, P.J.; Hamelijnck, M.A.F.; Kadaba, P.K.; Damani, L.A. J. Chromatogr. Biomed. Appl., 1991, 563, 419.
75. Hamelijnck, M.A.F.; Stevenson, P.J.; Kadaba, P.K.; Damani, L.A. J. Pharm. Sci., 1992, 81, 392.
76. Stevenson, P.J.; Hauksdottir, R.; Kadaba, P.K.; Damani, L.A. J. Chromatogr. Biomed. Appl., 1990, 533, 248-254.
77. Kiese, M. Methemoglobinemia, CRC Press: Cleveland, 1974.
78. Cavalheiro, E.A.; Lehmann, J.; Turski, L. (Eds); Frontiers in Excitatory Amino Acid Research, A.R. Liss: New York, 1988.
79. Meldrum, B.S.; Garthwaite, J. Trends Pharmacol. Sci., 1990, 11, 379-385.
80. Rothman, S.M.; Olney, J.W. Ann. Neurol., 1986, 19, 105-111.
81. Mayer, M.L.; Westbrook., G.L. Trends Neurosci., 1987, 10, 59; Prog. Neurobiol., 1987, 28, 197.
82. Greenamyre, J.T.; Maragos, W.F.; Albin, R.L.; Penny, J.B.; Young, A.B. Prog. Neuropsychopharmacol. & Biol. Psychiat., 1988, 12, 421.
83. Choi, D.S. Neuron, 1988, 1, 623.
84. Simpson, M.D.C.; Royston, M.C.; Deakin, J.F.W.; Cross, A.J.; Mann, D.M.A.; Slater, P. Brain Res., 1988, 462, 76.
85. Hahn, J.S.; Aizenman, E.; Lipton, S.A. Proc. Natl. Acad. Sci., 1988, 85, 6556.
86. Ogura, A.; Miyamoto, M.; Kudo, Y. Exp. Brain Res., 1988, 73, 447.
87. Kalichman, M.W. Neurosci. Biobehav. Rev., 1982, 6, 165.
88. Jorgenson, M.D.; Diemer, N.A. Acta Neurol. Scand., 1982, 66, 536-546.
89. Jorgenson, M.D.; Johnson, F.F.; Diemer, N.A. Acta. Neuropathol., 1987, 73, 189.
90. Linden, T.; Kalimo, H.; Weiloch, T. Acta Neuropathol., 1988, 74, 335.
91. Simon, R.P.; Griffiths, T.; Evans, M.C.; Swan, J.H.; Meldrum, B.S. J. Cereb. Blood Flow Metab., 1984, 4, 350-361.
92. Boast, C.A.; Gerhardt, S.C.; Pastor, G.; Lehmann, J.; Etienne, P.E.; Liebman, J.M. Brain Res., 1988, 442, 345-348.
93. Gill, R.; Foster, A.C.; Woodruff, G.N. J. Neurosci., 1987, 7, 3343-3349.
94. Benveniste, H.; Drejer, J.; Schousboe, A.; Diemer, N.A. J. Neurochem., 1984, 43, 1369.
95. Choi, D.W.; Maulucci-Gedde, M.A.; Kriegstein, A.R. J. Neurosci., 1987, 7, 357-368.
96. Rothman, S.M. J. Neurosci., 1984, 4, 188-191.
97. Ben-Ari, Y. Neurosci., 1985, 14, 375-403.
98. Meldrum, B.S.; Corsellis, J.A.N. In Greenfield's Neuropathology, 4th Ed, J.H. Adams, et al., Ed.; 1984, pp. 921-950.
99. Sloviter, R.S. Brain Res. Bull., 1983, 10, 675-697; Science, 1987, 73.
100. Griffiths, T.; Evans, M.C.; Meldrum, B.S. Neuroscience, 1983, 10, 385-395.
101. Fisher, M; Jones, S.; Sacco, R.L. Stroke, 1994, 25, 1075-1080.
102. Chandler, M.J.; DeLeo, J.; Carney, J.M. J. Pharmacol. Meth., 1985, 14, 137-146.
103. Busto, R.; Globus, M.Y.T.; Dietrich, W.D.; Martinez, E.; Valdes, I.; Ginsberg, M.D. Stroke, 1989, 20, 904-910.
104. Campos-Gonzales, R.; Kindy, M.S. J. Neurochem., 1992, 59, 1955-1958.
105. Brint, S.; Jacewicz, M.; Kiessling, M.; Tanabe, J.; Pulsinelli, W. J. Cereb. Blood Flow Metab., 1988, 8, 474-485.
106. Pettigrew, L.C.; Holtz, M.L.; Craddock, S.D.; Minger, S.L.; Hall, N.; Geddes, J.W. J. Cereb. Blood Flow Metab., 1996, 16, 1189-1202.
107. Smith-Swintosky, V.L.; Pettigrew, L.C.; Sapolsky, R.M.; Phares, C.; Craddock, S.D.; Brooke, S.M.; Mattson, M.P. J. Cereb. Blood Flow Metab., 1996, 16, 585-598.
108. Bederson, J.B.; Pitts, L.H.; Germano, S.M.; Nishimura, M.C.; Davis, R.L.; Bartkowski, H.M. Stroke, 1986, 17, 1304-1308.
109. Lin, Z.; Kadaba, P.K. Med. Res. Rev., 1997, 17, 537-572.
110. Ramsay, R.E. Neurol., 1994, 44, S23.
111. Matsuo, F.; Bergen, D.; Faught, E.; Messenheimer, J.A.; Dren, A.T.; Rudd, G.D.; Lineberry, C.G. Neurol., 1993, 43, 2284.
112. Sander, J.W.; Hart, Y.M.; Trimble, M.D.; Shorvon, S.D. Epilepsia, 1992, 32 (suppl. 1), 12.
113. Sachdeo, R.; Leroy, R.; Krauss, G.; Green, P.; Drake, M.; Leppik, I.; Shu, V.; Ringham, G.; Sommerville, K. Neurology, 1995, 45 (suppl. 4), 202.