Dihydropyridazinone Cardiotonics: Synthesis and Inotropic Activity of 5′-(l,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)spiro[cycloalkane-l,3′-[3H]indol]-2′(1′T)-ones

Journal of Medicinal Chemistry

Volumn 30, Issue 5, 1987, Pages 824-829

  Robertson, David W ^a   Krushinski, Joseph H ^a   Pollock, G Don ^a   Wilson, Harve ^a   Kauffman, Raymond F ^a   Hayes, J Scott ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PRIORITY JOURNAL;

3',5'-CYCLIC-NUCLEOTIDE PHOSPHODIESTERASE; ANIMALS; CHEMISTRY; DOGS; FEMALE; INDOLES; ISOENZYMES; MALE; MYOCARDIAL CONTRACTION; MYOCARDIUM; PYRIDAZINES; SARCOPLASMIC RETICULUM; SPIRO COMPOUNDS; STIMULATION, CHEMICAL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0023215233     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00388a014     Document Type: Article

References (30)

1. Bairn, D. S.; Colucci, W. S.; Monrad, E. S.; Smith, H. S.; Wright, R. F.; Lanoue, A.; Gauthier, D. F.; Ransil, B. J.; Grossman, W.; Braunwald, E. J. Am. Coll. Cardiol. 1986, 7, 661.
2. Sonnenblick, E. H.; Grose, R.; Strain, J.; Zelcer, A.; LeJemtel, T. H. Circulation, Suppl. Ill 1986, 73, 162.
3. Arbogast, R.; Brandt, C. M.; Fincker, J. L.; Schnechter, P. J. J. Cardiovasc. Pharmacol. 1986, 8, 82,
4. Robertson, D. W.; Beedle, E. E.; Krushinski, J. H.; Pollock, G. D.; Wilson, H.; Wyss, V. L.; Hayes, J. S. J. Med. Chem. 1985, 28, 717.
5. Hayes, J. S.; Bowling, N.; Pollock, G. D.; Robertson, D. W. J. Pharmacol. Exp. Ther. 1986, 237, 18.
6. Hayes, J. S.; Pollock, G. D.; Wilson, H.; Bowling, N.; Robertson, D. W. J. Pharmacol. Exp. Ther. 1905, 233, 318.
7. For a recent review, see: Colucci, W. S.; Wright, D. F.; Braunwald, E. N. Engl. J. Med. 1986, 314, 349.
8. Weishaar, R. E.; Cain, M. H.; Bristol, J. A. J. Med. Chem. 1985, 28, 537.
9. Endoh, M.; Yanagisawa, T.; Monta, T.; Taira, N. J. Pharmacol Exp. Ther. 1985, 234, 267.
10. Packer, M. Circulation 1985, 72, 681.
11. Goldstein, R. A.; Geraci, S. A.; Gray, E. L.; Rmkenberger, R. L.; Dougherty, A. H.; Naccarelli, G. V. Am. J. Cardiol. 1986, 57, 624.
12. Naccarelli, G. V.; Gray, E. L.; Dougherty, A. H.; Hanna, J. E.; Goldstein, R. A. Am. J. Cardiol. 1984, 54, 600.
13. Muller, J. E.; Turi, Z. G.; Stone, P. H.; Rude, R. E.; Raabe, D. S.; Jaffe, A. S.; Gold, H. K.; Gustafson, N.; Poole, W. K.; Passamani, E.; Smith, T. W.; Braunwald, E. N. Engl. J. Med. 1986, 314, 265.
14. Yusuf, S.; Wittes, J.; Bailey, K.; Furberg, C. Circulation 1986, 75, 14.
15. Robertson, D. W.; Krushinski, J. H.; Beedle, E. E.; Wyss, V.; Pollock, G. D.; Wilson, H.; Kauffman, R. F.; Hayes, J. S. J. Med. Chem. 1986, 29, 1832.
16. Hayes, J. S.; Pollock, G. D.; Wilson, H.; Bowling, N.; Robertson, D. W. J. Cardiovasc. Pharmacol., in press.
17. For a review of indoles with C-3 as a spiro atom, see: Joehi, K. C.; Jain, R.; Chand, P. Heterocycles 1985, 23, 957.
18. Thyes, M.; Lehmann, H. D.; Gries, J.; Konig, H.; Kretzschmar, R.; Kunze, J.; Lebkucher, R.; Lenke, D. J. Med. Chem. 1983, 26, 800
19. Sircar, I.; Duell, B. L.; Bobowski, G.; Bristol, J. A.; Evans, D. Bo. J. Med. Chem. 1985, 28,1405.
20. Bristol, J. A.; Sircar, I.; Moos, W. H.; Evans, D. B.; Weishaar, P. E. J. Med. Chem. 1984, 27, 1099.
21. Thompson, W. J.; Terasaki, W. L. ; Epstein, P. M.; Strada, S. J. Adv. Cycl. Nucl. Res. 1979, 9, 69.
22. Kauffman, R. F.; Crowe, V. G.; Robertson, D. W. Fed. Proc., Fed. Am. Soc. Exp. Biol. 1986, 45. 1049.
23. Kauffman, R. F.; Crowe, V. G.; Utterback, B. G.; Robertson, Dq. W. Mol. Pharmacol. 1986, 30, 609.
24. Moore, R. Fqg.; Plant, S. G. P. J. Chem. Soc., 1951, 3475,
25. Wenkert, E.; Bindra, J. S.; Chang, C. J. ; Cochran, D. W.; Rearick, D. E. J. Org. Chem. 1974, 39, 1662.
26. Jonesxbpys, L. R.; Besoh, H. R., Jr.; Fleming, J. W.; McConftaughey, M. M.; Watanabe, A. M. J. Biol. Chem. 1979, 254, 530.
27. Jonsxbpyes, L. R.; Cala, S. E. J. Biol. Chem. 1981, 256, 11809.
28. Seiler, S.; Wegener, A. D.; Whang, D. D.; Hathaway, D. R.; Jones, L. R. J. Biol. Chem. 1984, 259, 8550
29. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. J. Biol. Chem. 1951,193, 265.
30. Tallarida, R. J.; Murray, R. B. Manual of Pharmacological Calculations; Springer-Verlag: New York, 1981.