Nonpeptide arginine vasopressin antagonists for both V(1A) and V2 receptors: Synthesis and pharmacological properties of 2-phenyl-4'-(2,3,4,5- tetrahydro-1H-1,5-benzodiazepine-1-carbonyl)benzanilide derivatives

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 10, 1998, Pages 1566-1579

  Matsuhisa, Akira ^a   Koshio, Hiroyuki ^a   Sakamoto, Kenichiro ^a   Taniguchi, Nobuaki ^a   Yatsu, Takeyuki ^a   Tanaka, Akihiro ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

Antidiuretic hormone; Arginine vasopressin antagonist; Benzanilide; Benzodiazepine; Congestive heart failure

Indexed keywords

1 [1 [4 (3 ACETAMIDOPROPOXY)BENZOYL] 4 PIPERIDYL] 1,2,3,4 TETRAHYDRO 2 QUINOLINONE; 2 PHENYL 4' (2,3,4,5 TETRAHYDRO 1H 1,5 BENZODIAZEPINE 1 CARBONYL)BENZANILIDE; ARGIPRESSIN RECEPTOR; MOZAVAPTAN; N TERT BUTYL 4 [5' ETHOXY 4 (2 MORPHOLINOETHOXY) 2' OXOSPIRO[CYCLOHEXANE 1,3' INDOLE] 1' SULFONYL] 3 METHOXYBENZAMIDE; RELCOVAPTAN; UNCLASSIFIED DRUG; VASOPRESSIN; VASOPRESSIN ANTAGONIST;

ARTICLE; BINDING AFFINITY; CONGESTIVE HEART FAILURE; DRUG BIOAVAILABILITY; DRUG SYNTHESIS; ENZYME ACTIVITY; HYDROPHILICITY; PROGNOSIS; PROTON NUCLEAR MAGNETIC RESONANCE; WATER ABSORPTION;

EID: 0031792771     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1566     Document Type: Article

References (18)

1. Michel R. H., Kirk C. J., Billah M. M., Biochem. Soc. Trans., 7, 861-865 (1979).
2. Jard S., Kidney Int., Supp., 26, 38-42 (1988).
3. Ogawa H., Yamamura Y., Miyamoto H., Kondo K., Yamashita H., Nakaya K., Chihara T., Mori T., Tominaga M., Yabuuchi Y., J. Med. Chem., 36, 2011-2017 (1993).
4. 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., 39, 3547-3555 (1996).
5. Serradeil-Le Gal C., Wagnon J., Garcia C., Lacour C., Guiraudou P., Christophe B., Villanova G., Nisato D., Maffrand J. P., Le Fur G., Guillon G., Cantau B., Barberis C., Trueba M., Ala Y., Jard S., J. Clin. Invest., 92, 224-231 (1993).
6. Serradeil-Le Gal C., Lacour C., Valette G., Garcia G., Foulon L., Galindo G., Bankir L., Pouzet B., Guillon G., Barberis C., Chicot D., Jard S., Vilain P., Garcia C., Marty E., Raufaste D., Brossard G., Nisato D., Maffrand J. P., Le Fur G., J. Clin. Invest., 98, 2729-2738 (1996).
7. Manning M., Sawyer W. H., J. Lab. Clin. Med., 114, 617-632 (1989).
8. Creager M. A., Facon D. P., Cutler S. S., Kohlmann O., Ryan T. J., Gavras H., J. Am. Coll. Cardiol., 7, 758-765 (1986).
9. Lee W. H., Packer M., Circuration, 73, 257-267 (1986).
10. Matsuhisa A., Tanaka A., Kikuchi K., Shimada Y., Yatsu T., Yanagisawa I., Chem. Pharm. Bull., 45, 1870-1874 (1997).
11. Carabateas P. M., Harris L.S., J. Med. Chem., 9, 6-10 (1966).
12. Gatta F., Vittory R. L., Tomassetti M., Barrios G. N., Chim. Ther., 7, 480-483 (1972).
13. Ichii T., Yakugaku Zassi, 82, 992-998 (1962).
14. Korshak V. V., Rusanov A. L., Batirov I., Kalontarov I. Ya., Niyazi F. F., Plieva L. Kh., Dokl. Akad. Nauk Tadzh. SSR, 20, 37-39 (1977) (Chem. Abstr., 88, 152537k (1978)).
15. Korshak V. V., Rusanov A. L., Batirov I., Kalontarov I. Ya., Niyazi F. F., Plieva L. Kh., Dokl. Akad. Nauk Tadzh. SSR, 20, 37-39 (1977) (Chem. Abstr., 88, 152537k (1978)).
16. Bauer A., Weber K. H., Unruh M., Arch. Pharmaz., 305, 557-570 (1972).
17. clogP values were calculated with CLOGP (Tripos, Inc).
18. Tahara A., Tomura Y., Wada K., Kusayama T., Tsukada J., Takanashi M., Yatsu T., Uchida W., Tanaka A., J. Pharmacol. Exp. Ther., 282, 301-308 (1997).