Structure-Activity Relationships of Arylimidazopyridine Cardiotonics: Discovery and Inotropic Activity of 2-[2-Methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4, 5-c]pyridine

Journal of Medicinal Chemistry

Volumn 28, Issue 6, 1985, Pages 717-727

  Robertson, David W ^a   Beedle, E E ^a   Krushinski, Joseoh H ^a   Pollock, G Don ^a   Wilson, H ^a   Wyss, Virginia L ^a   Hayes, J Scott ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLIMIDAZO[4,5 B]PYRIDINE DERIVATIVE; 2 PHENYLIMIDAZO[4,5 C]PYRIDINE DERIVATIVE; 8 PHENYLPURINE DERIVATIVE; AMRINONE; CARDIOTONIC AGENT; ISOMAZOLE; NEW DRUG; PENTOBARBITAL; SULMAZOLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BIOLOGICAL MODEL; BLOOD PRESSURE; CARDIOVASCULAR SYSTEM; CAT; DOG; DOSE RESPONSE; DRUG ANALYSIS; DRUG COMPARISON; DRUG IDENTIFICATION; DRUG RESPONSE; DRUG SCREENING; DRUG SYNTHESIS; HEART; HEART RATE; INOTROPISM; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; CARDIOTONIC AGENTS; CATS; DOGS; FEMALE; IMIDAZOLES; MALE; MYOCARDIAL CONTRACTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0021816086     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00383a006     Document Type: Article

References (42)

1. Portions of this work have been previously presented: Robertson, D. W.; Beedle, E. E.; Krushinski, J. H.; Pollock, G. D.; Wilson, H.; Hayes, J. S. “Abstracts of Papers”, 188th National Meeting of the American Chemical Society, Philadelphia, PA, Aug 1984; American Chemical Society:Washington, DC, 1984; MEDI 10. Hayes, J. S.; Pollock, G. D.; Wilson, H.; Bowling, N.; Robertson, D. W. Fall Meeting of the American Society for Pharmacology and Experimental Therapeutics, Indianapolis, IN, August 19–23, 1984; Abstr 207.
2. Franciosa, J. A.; Wilen, M.; Ziesche, S. Am. J. Cardiol. 1983, 51, 831.
3. Cohn, J. N. In “Congestive Heart Failure: Current Research and Clinical Applications”; Braunwald, E., Mock, M. B., Watson, J. T., Eds.; Grieve and Stratton: New York, 1982; pp 11–13.
4. Beller, G. A.; Smith, T. W.; Abelmann, W. H.; Haber, E.; Hood, W. B., Jr. N. Engl. J. Med. 1971, 284, 989.
5. Mason, D. T.; Zelis, R.; Lee, G.; Hughes, J.; Spann, J.; Amsterdam, A. E. Am. J. Cardiol. 1971, 27, 546.
6. Lee, D.C.-S.; Johnson, R. A.; Bingham, J. B.; Leahy, M.; Dinsmore, R. E.; Goroll, A. H.; Newell, J. B.; Strauss, H. W.; Haber, E. N. Engl. J. Med. 1982, 306, 699.
7. Ford, A. R.; Aronson, J. K.; Grahame-Smith, D. G.; Carver, J. G. Br. J. Clin. Pharmacol. 1979, 8, 135.
8. Doherty, J. E.; Kane, J. J. Ann. Rev. Med. 1975, 26, 159.
9. Goldberg, L. I. Am. J. Cardiol. 1968, 22, 177.
10. Su, Y.-F.; Harden, T. K.; Perkins, J. P. J. Biol. Chem. 1980, 255, 7410.
11. Mukherjee, C.; Caron, M. G.; Lefkowitz, R. J. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 1945.
12. Bristow, M. R.; Ginsburg, R.; Minobe, W.; Cubicciotti, R. S.; Sageman, W. S.; Lurie, K.; Billingham, M. E.; Harrison, D. C.; Stinson, E. B. N. Engl. J. Med. 1982, 307, 205.
13. Colucci, W. S.; Alexander, R. W.; Williams, G. H.; Rude, R. E.; Holman, B. L.; Konstam, M. A.; Wynne, J.; Mudge, G. H., Jr.; Braunwald, E. N. Engl. J. Med. 1981, 305, 185.
14. Harden, T. K. Pharmacol. Rev. 1983, 35, 5. (15) For a comprehensive review, see: Ward, A.; Brogden, R. N.; Heel, R. C.; Speight, T. M.; Avery, G. S. Drugs 1983, 26, 468.
15. Alousi, A. A.; Edelson, J. “Pharmacological and Biochemical Properties of Drug Substances”; Goldberg, M. E., Ed.; American Pharmaceutical Association: Washington, DC, 1981; p 120.
16. Schnettler, R. A.; Dage, R. C.; Grisar, J. M. J. Med. Chem. 1982, 25, 1477.
17. Crawford, M. H.; Richards, K. L.; Sodums, M. T.; Kennedy, G. T. Am. J. Cardiol. 1984, 53, 1051.
18. Diederen, W.; Kadatz, R. Arzneim.-Forsch. 1981, 31, 141 and all subsequent papers in this issue.
19. Kariya, T.; Wille, L. J.; Dage, R. C. J. Cardiovasc. Pharmacol. 1982, 4, 509.
20. Endoh, M.; Yamashita, S.; Taira, N. J. Pharmacol. Exp. Ther. 1982, 221, 775.
21. Jentzer, J. H.; LeJemtel, T. H.; Sonnenblick, E. H.; Kirk, E. S. Am. J. Cardiol. 1981, 48, 75.
22. Dage, R. C.; Roebel, L. E.; Hsieh, C. P.; Weiner, D. L.; Woodward, J. K. J. Cardiovasc. Pharmacol. 1982, 4, 500.
23. Diederen, W.; Kadatz, R. Arzneim.-Forsch. 1981, 31, 146. (25) Weber, K. T.; Andrews, V.; Janicki, J. S.; Likoff, M.; Reichek, N. Circulation 1982, 66, 1262.
24. Miller, R. R.; Palomo, A. R.; Brandon, T. A.; Hartley, C. J.; Quinones, M. A. Am. Heart J. 1981, 102, 500.
25. Pouleur, H.; Rousseau, M. F.; Mechelen, H. V.; Petein, M.; Ries, A.; Charlier, A. A. J. Cardiovasc. Pharmacol. 1982, 4, 409.
26. Benotti, J. R.; Grossman, W.; Braunwald, E.; Carabello, B. A. Circulation 1980, 62, 28.
27. Robertson, D. W.; Hayes, J. S. European Patent Application 93 593, November 9, 1983.
28. Middleton, R. W.; Wibberley, D. G. J. Heterocycl. Chem. 1980, 17, 1757.
29. Kutter, E.; Austel, V.; Diederen, W. U.S. Patent 3985891, October 12, 1976.
30. Zipp, H.; Roth, W.; Zimmer, A. Arzneim.-Forsch. 1981, 31, 200.
31. Kutter, E.; Austel, V. Arzneim.-Forsch. 1981, 31, 135.
32. Austel, V.; Kutter, E.; Heider, J.; Diederen, W. U.S. Patent 4 299 834, November 10, 1981.
33. Robertson, D. W.; Beedle, E. E.; Jones, N. D.; Swartzendruber, J. K.; Hayes, J. S., unpublished observations.
34. Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207.
35. Fennell, W. H.; Taylor, A. A.; Young, J. B.; Brandon, T. A.; Ginos, J. Z.; Goldberg, L. I.; Mitchell, J. R. Circulation 1983, 67, 829.
36. LeJemtel, T. H.; Keung, E.; Sonnenblick, E. H.; Ribner, H. S.; Matsumoto, M.; Davis, R.; Schwartz, W.; Alousi, A. A.; Darolos, D. D. Circulation 1979, 59, 1098.
37. Siegel, L. A.; Keung, E.; Siskind, S. J.; Forman, R.; Feinberg, H.; Strom, J.; Efstathakis, D.; Sonnenblick, E. H.; LeJemtel, T. H. Circulation 1981, 63, 838.
38. Wilmshurst, P. T.; Webb-Peploe, M. M. Br. Heart J. 1983, 49, 447.
39. Wilmshurst, P. T.; Thompson, D. S.; Jenkins, B. S.; Coltart, D. J.; Webb-Peploe, M. M. Br. Heart J. 1983, 49, 77.
40. Hermiller, J. B.; Leithe, M. E.; Magorien, R. D.; Unverferth, D. V.; Leier, C. V. J. Pharmacol. Exp. Therap. 1984, 228, 319.
41. Wilmshurst, P. T.; Walker, J. M.; Fry, C. Hh.; Mounsey, J. P.; Twort, C. H. C.; Williams, B. T.; Davies, M. J.; Webb-Peploe, M. M. Cardiovas. Res. 1984, 18, 302.
42. Roth, V. W.; Prox, A.; Reuter, A.; Schmid, J.; Zimmer, A.; Zipp, H. Arzneim.-Forsch. 1981, 31, 232.