5-Fluoro-2-methyl-N-[4-(5H-pyrrolo[2,1-c]-[1,4]benzodiazepin-10(11H)- ylcarbonyl)-3-chlorophenyl]benzamide (VPA-985): An orally active arginine vasopressin antagonist with selectivity for V2 receptors [2]

Journal of Medicinal Chemistry

Volumn 41, Issue 14, 1998, Pages 2442-2444

  Albright, J Donald ^a   Reich, Marvin F ^a   Delos Santos, Efren G ^a   Dusza, John P ^a   Sum, Fuk Wah ^a   Venkatesan, Aranapakam M ^a   Coupet, Joseph ^a   Chan, Peter S ^a   Ru, Xun ^a   Mazandarani, Hossein ^a   Bailey, Trina ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 FLUORO 2 METHYL N [5H PYRROLO [2,1 C] [1,4] BENZODIAZEPIN 10(11H) YLCARBONYL 3 CHLOROPHENYL]BENZAMIDE; AQUAPORIN; ARGIPRESSIN RECEPTOR; MOZAVAPTAN; N [2 (1 MERCAPTOCYCLOHEXYL)ACETYL] DEXTRO O ETHYLTYROSYLPHENYLALANYLVALYLASPARAGINYLCYSTEINYLPROLYLARGININAMIDE DISULFIDE; UNCLASSIFIED DRUG;

BINDING AFFINITY; BLOOD VOLUME; DECHLORINATION; LETTER; ORAL DRUG ADMINISTRATION; OSMOLALITY; OSMORECEPTOR; PERMEABILITY; PRESSORECEPTOR; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; ARGININE VASOPRESSIN; AZEPINES; BENZAMIDES; BLOOD PLATELETS; BODY WATER; CELL LINE; CELL MEMBRANE; DOGS; FIBROBLASTS; HUMANS; KIDNEY; LIVER; OSMOLAR CONCENTRATION; RATS; RECEPTORS, VASOPRESSIN; SODIUM; STRUCTURE-ACTIVITY RELATIONSHIP; URINE;

EID: 14444285742     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980179c     Document Type: Letter

References (33)

1. Laszlo, F. A.; Laszlo, F., Jr.; De Wied, D. Pharmacology and Clinical Perspectives of Vasopressin Antagonists. Pharmacol. Rev. 1991, 43, 73-108.
2. 1- Vascular Vasopressin Receptors. Regulatory Pept. 1992, 38, 1-11.
3. Laszlo, F. A.; Laszlo, F., Jr. Clinical Perspectives for Vasopressin Antagonists. Drug News Perspect. 1993, 6, 591-599.
4. Nielsen, S.; Knepper, M. A. Vasopressin Activates Collecting Duct Urea Transporters and Water Channels by Distinct Physical Processes. Am. J. Physiol. 1993, 265, F204-F213.
5. Knepper, M. A.; Nielsen, S. Kinetic Model of Water and Urea Permeability Regulation by Vasopressin in Collecting Duct. Am. J. Physiol. 1993, 265, F214-F224.
6. Nielsen, S.; Muller, J.; Knepper, M. A. Vasopressin and cAMP-induced Changes in Ultrastructure of Isolated Perfused Inner Medullary Collecting Ducts. Am. J. Physiol. 1993, 265, F225-338.
7. 2 Receptor in Terminal Inner Medullary Collecting Ducts. J. Clin. Invest. 1995, 96, 1768-1778.
8. Knepper, M. A.; Nielson, S.; Chou, C.-L.; DiGiovanni, S. R. Mechanism of Vasopressin Action in the Renal Collecting Duct. Semin. Nephrol. 1994, 14, 302-321.
9. Knepper, M. A. The Aquaporin Family of Molecular Water Channels. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6255-6258.
10. 2 Receptor. J. Clin. Invest. 1996, 97, 2763-2771.
11. 2 Receptor in Rat Kidney. J. Clin. Invest. 1994, 94, 1778-1783.
12. 1 Receptor Antagonist. Science 1991, 252, 572-574.
13. 1 Antagonists. A Novel Series of 1-(1-Substituted 4-piperidyl)-3,4-dihydro-2(1H)-quinolinone. J. Med. Chem. 1993, 36, 2011-2017.
14. 1a Antagonists: 1-(1-Multi-substituted Benzoyl 4-Piperidyl)-3,4-dihydro -2(1H)-quinolinones. Chem. Pharm. Bull. 1996, 44, 725-733.
15. 2 Receptor Antagonist. Br. J. Pharmacol. 1992, 105, 787-791.
16. Ohnishi, A.; Orita, Y.; Okahara, R.; Fujihara, H.; Inoue, T.; Yamamura, Y.; Yabuuchi, Y.; Tanaka, T. Potent Aquaretic Agent. J. Clin. Invest. 1993, 92, 2653-2659.
17. 2 Antagonist in Men. J. Pharmacol. Exp. Ther. 1995, 272, 546-551.
18. 2 Receptor Antagonists: a Novel Series of 1-[(4-Benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine and Related Compounds. J. Med. Chem. 1996, 39, 3547-3555.
19. Ogawa, H.; Miyamoto, H.; Kondo, K.; Yamashita, H.; Nakaya, K.; Komatsu, H.; Tanaka, M.; Kora, S.; Tominaga, M.; Yabuuchi, Y. Benzoheterocyclic Compounds. U.S. Patent 5,559,230, Sept 24, 1996.
20. Artico, M.; de Martine, G.; Filacchioni, G.; Giuliano, R. Ricerche su Sostanze ad Attivita Antiblastica, Parte I.; Sintesi Delia 10,-11-Diidro-5H-pirrolo[2,1-c][1,4]benzodiazepine. Farmaco, Ed. Sci. 1969, 24, 276-284.
21. Wright, W. B., Jr.; Greenblatt, E. M.; Day, I. P.; Quinones, N. Q.; Hardy, R. A. Derivatives of 11-(1-Piperazinyl)-5H-pyrrolo-[2,1-c][1,4]benzodiazepine as Central Nervous System Agents. J. Med. Chem. 1980, 23, 462-465.
22. Adger, B. M.; Young, R. G. Selective Reduction of Nitroaryl-alkylnitriles with Hydrazine and a Metal Catalyst. Tetrahedron Lett. 1984, 25, 5219-5222.
23. Bellamy, F. D., Ou, K. Selective Reduction of Aromatic Nitro Compounds with Stannous Chloride in Nonacidic and Nonaqueous Medium. Tetrahedron Lett. 1984, 25, 839-842. Errata. Tetrahedron Lett. 1985, 26, 1362.
24. Albright, J. D.; Reich, M. F.; Sum, F. W.; Delos Santos, E. G. Tricyclic Diazepine Vasopressin Antagonists and Oxytocin Antagonists. U.S. Patent 5,516,774, May 14, 1996.
25. Birnbaumer, M.; Seibold, A.; Gilbert, S.; Ishido, M.; Barberis, C.; Antaramian, A.; Brobet, P.; Rosenthal, W. Molecular Cloning of the Receptor for Human Antidiuretic Hormone. Nature 1992, 357, 333-335.
26. Seibold, A.; Rosenthal, W.; Barberis, C.; Birnbaumer, M. Cloning of the Human Type-2 Vasopressin Receptor Gene. Ann. N.Y. Acad. Sci. 1993, 689, 570-573.
27. Kruszyki, M.; Lammek, B.; Manning, M. [1-(β-Mercapto-β,β-cyclopentamethlenepropionic acid), 2-(O-Methyl)tyrosine]arginine-vasopresain and [1-(β-Mercapto-β,β-cyclopentamethylenepropionic acid)]-arginine-vasopressin, Two Highly Potent Antagonists of the Vasopressor Response to Arginine-vasopressin. J. Med. Chem. 1980, 23, 364-368.
28. 1 Receptor of Rat, Rhesus, and Human Tissues. Life Sci. 1992, 50, 1953-1958.
29. 1a, Receptors. J. Clin. Invest. 1993, 92, 224-231.
30. 1a Antagonist, to Rat and Human Liver Membranes. Biochem. Biophys. Res. Commun. 1994, 199, 353-360.
31. Kinter, L. B.; Caltabiano, S.; Huffman, W. F. Anomalous Antidiuretic Activity of Antidiuretic Hormone Antagonists. Biochem. Pharm. 1993, 45, 1731-1737.
32. 2 Receptor Vasopressin Antagonist in Patients with Chronic Heart Failure. J. Am. Coll. Cardiol. 1997, 29 (2 Suppl. A): 169A.
33. 2 Receptor Antagonists. Curr. Pharm. Des. 1997, 3, 615-632.