Novel vasopressin V2 receptor-selective antagonists, pyrrolo[2,1-a]quinoxaline and pyrrolo[2,1-c][1,4]benzodiazepine derivatives

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 6, 1999, Pages 1247-1254

  Ohtake, Yasuhiro ^a   Naito, Akira ^a   Hasegawa, Hisashi ^a   Kawano, Katsuhiro ^a   Morizono, Daisuke ^a   Taniguchi, Makoto ^a   Tanaka, Yoko ^a   Matsukawa, Hidehiko ^a   Naito, Kenji ^a   Oguma, Touru ^a   Ezure, Yohji ^a   Tsuriya, Yoshihiro ^a  

^a Wakamoto Pharmaceutical Co Ltd   (Japan)

Author keywords

Antagonists; Benzodiazepines; Hormones; Receptors

Indexed keywords

BENZODIAZEPINE DERIVATIVE; VASOPRESSIN; VASOPRESSIN ANTAGONIST; VASOPRESSIN V2 RECEPTOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DIURESIS; DIURETIC ACTIVITY; DRUG EFFICACY; DRUG SYNTHESIS; HEART FAILURE; HYPERTENSION; HYPONATREMIA; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; ORAL DRUG ADMINISTRATION; RAT; SCHWARTZ BARTTER SYNDROME;

ANIMALS; BENZODIAZEPINES; DIURESIS; DIURETICS; PYRROLES; QUINOXALINES; RATS; RECEPTORS, VASOPRESSIN; STRUCTURE-ACTIVITY RELATIONSHIP; VASOPRESSINS;

EID: 0033008252     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00049-8     Document Type: Article

References (31)

1. Thibonnier, M.; Auzan, C.; Madhun, Z.; Wilkins, P.; Berti-Mattera, L.; Clauser, E. J. Biol. Chem., 1994, 269, 3304-3310.
2. Sugimoto, T.; Saito, M.; Mochizuki, S.; Watanabe, Y.; Hashimoto, S.; Kawashima, H. ibid., 1994, 269, 27088-27092.
3. Birnbaumer, M.; Seibold, A.; Gilbert, S.; Ishido, M.; Barberis, C.; Antaramian, A.; Bradet, P.; Rosenthal, W. Nature, 1992, 357, 333-335.
4. Serradeil-Le-Gal, C.; Herbert, J. M.; Delisee, C.; Schaeffer, P.; Raufaste, D.; Garcia, C.; Dol, F.; Marty, E.; Maffrand, J. P.; Le Fur, G. Am. J. Physiol., 1995, 268, H404-H410.
5. Howl, J.; Ismail, T.; Strain, A. J.; Kirk, C. J.; Anderson, D.; Wheatley, M. Biochem., 1991, 276, 189-195.
6. Manning, M.; Sawyer, W. H. J. Recept. Res., 1993, 13, 195-214.
7. Jard, S.; Gaillard, R. C.; Guillon, G.; Marie, J.; Schoenenberg, P.; Muller, A. F.; Manning, M.; Sawyer, W. H. Mol. Pharmacol., 1986, 30, 171-177.
8. Michell, R. H.; Kirk, C. J.; Billah, M. M. Biochem. Soc. Trans., 1979, 7, 861-865.
9. Butlen, D.; Guillon, G.; Rajerison, R. M.; Jard, S.; Sawyer, W. H.; Manning, M. ibid., 1978, 14, 1006-1017.
10. Manning, M.; Sawyer, W. H. J. Recept. Res., 1993, 13, 195-214.
11. Kinter, L. B.; Huffman, W. F.; Stassen, F. L. Am. J. Phisiol., 1988, 254, F165-F177.
12. Laszlo, F. A.; Laszlo Jr, F.; De Wied, D. Pharmacol. Rev., 1991, 43, 73-108.
13. Manning, M.; Sawyer, W. H. J. Lab. Clin. Med., 1989, 114, 617-632.
14. Manning, M.; Chan. W. Y. Regul. Pept., 1993, 45, 279-283.
15. Mah, S. C.; Hofbauer, K. G. J. Pharmacol. Exp. Ther., 1988, 245, 1028-1032.
16. Huffman, W. F.; Albrightson-Winslow, C.; Brickson, B.; Bryan, H. G.; Caldwell, N.; Dytko, G.; Eggleston, D. S.; Kinter, L. B.; Moore, M. L.; Newlander, K. A.; Schmidt, D. B.; Silvestri, J. S.; Stassen, F. L.; Yim, N. C. F. J. Med. Chem., 1989, 32, 880-884.
17. (a) Yamamura, Y.; Ogawa, H.; Chihara, T.; Kondo, K.; Onogawa, T.; Nakamura, S.; Mori, T.; Tominaga, M.; Yabuuchi, Y. Science, 1991, 252, 572-574.
18. (b) Ogawa, H.; Yamamura, Y.; Yamamoto, H.; Kondo, K.; Yamashita, H.; Nakaya, K.; Chihara, T.; Mori, T.; Tominaga, M.; Yabuuchi, Y. J. Med. Chem., 1993, 36, 2011-2017.
19. Ogawa, H.; Yamashita, H.; Kondo, K.; Yamamura, Y.; Miyamoto, H.; Kan, K.; Kitano, K.; Tanaka, M.; Nakaya, K.; Nakamura, S.; Mori, T.; Tominaga, M.; Yabuuchi, Y. J. Med. Chem., 1996, 39, 3547-3555.
20. Tahara, A.; Tamura, Y.; Wada, K.; Kusayama, T.; Tsukada, J.; Takanashi, M.; Yatsu, T.; Uchida, W.; Tanaka, A. J. Pharmacol. Exp. Ther., 1997, 282, 301-308.
21. Matsuhisa, A.; Tanaka, A.; Kikuchi, K.; Shimada, Y.; Yatsu, T.; Yanagisawa, I. Chem. Pharm. Bull., 1997, 45, 1870-1874.
22. Bock, M. G.; DiPardo, R. M.; Evans, B. E.; Rittle, K. E.; Whitter, W. L.; Veber, D. F.; Anderson, P. S.; Freidinger, R. M. J. Med. Chem., 1989, 32, 13-16.
23. Desai, M. C.; Lefkowitz, S. L.; Thadeio, P. F.; Longo, K. P.; Snider, R. M. J. Med. Chem., 1992, 35, 4911-4913.
24. Hamann, L. G.; Farmer, L. J.; Johnson, M. G.; Bender, S. L.; Mais, D. E.; Wang, M. W.; Crombie, D.; Goldman, M. E.; Jones, T. K. J. Med. Chem., 1996, 39, 1778-1789.
25. Anderson, N. G.; Lust, D. A.; Colapret, K. A.; Simpson, J. H.; Malley, M. F.; Gougoutas, J. Z. J. Org. Chem., 1996, 61, 7955-7958.
26. Fryer, R. I.; Zhang, P.; Lin, Kuei-Ying; Upasani, R. B.; Wong, G.; Skolnick, P. Med. Chem. Res., 1993, 3, 183-191.
27. Edwin, V.; Namkyu, L. J. Am. Chem. Soc., 1995, 117, 891-900.
28. Umino, N.; Iwamura, T.; Itoh, N. Tetrahedron Letters, 1976, 763-766.
29. Kamal, A.; Rao, N. V. Chem. Commun., 1996, 385-386.
30. Jay, D. A.; Aranapakam, M. V.; John, P. D.; Fun-Wah Sum. US Patent, 5700796. Chem. Abstr. 1997, 128, 88934.
31. Thibonnier, M; Bayer, A. L.; Simonson, M. S.; Kester, M. Endocrinology, 1991, 129, 2845-2856.