Synthesis and pharmacological profile of non-peptide vasopressin antagonists

European Journal of Pharmaceutical Sciences

Volumn 24, Issue 5, 2005, Pages 421-431

  Galanski, Maria E ^a   Erker, Thomas ^a   Studenik, Christian R ^a   Kamyar, Majidreza ^a   Rawnduzi, Pakiza ^a   Pabstova, Martina ^a   Lemmens Gruber, Rosa ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Guinea pig; Papillary muscle; Smooth muscle; Thienothiazepines; Thienothiazines; Vasopressin antagonism

Indexed keywords

3,4 DIHYDRO 2H THIENO[3,2 B][1,4]THIAZIN 4 YL(4 NITROPHENYL)METHANONE; N 4 (3,4 DIHYDRO 2H THIENO[3,2 B][1,4]THIAZIN 4 YLCARBONYL)PHENYLACETAMIDE; N [4 (2 BENZYL 4,5,6,7 TETRAHYDROTHIENO[2,3 B][1,4]THIAZEPIN 4 YLCARBONYL)PHENYL] 2 METHOXYBENZAMIDE; N [4 (2 BENZYL 4,5,6,7 TETRAHYDROTHIENO[2,3 B][1,4]THIAZEPIN 4 YLCARBONYL)PHENYL] 2 METHYLBENZAMIDE; N [4 (3,4 DIHYDRO 2H THIENO[3,2 B][1,4]THIAZIN 4 YLCARBONYL)PHENYL] 2 METHYLBENZAMIDE; N [4 (3,4 DIHYDRO 2H THIENO[3,2 B][1,4]THIAZIN 4 YLCARBONYL)PHENYL] 2,6 DICHLOROBENZAMIDE; N [4 (3,4 DIHYDRO 2H THIENO[3,2 B][1,4]THIAZIN 4 YLCARBONYL)PHENYL] 4 FLUOROBENZAMIDE; N [4 (6 BENZYL 2,3 DIHYDRO 1H THIENO[2,3 B][1,4]THIAZIN 1 YLCARBONYL)PHENYL] 2,4 DIMETHYLBENZAMIDE; N [4 (6 BENZYL 2,3 DIHYDRO 1H THIENO[2,3 B][1,4]THIAZIN 1 YLCARBONYL)PHENYL] 2,6 DICHLOROBENZAMIDE; N [4 (6 ETHYL 2,3 DIHYDRO 1H THIENO[2,3 B][1,4]THIAZIN 1 YLCARBONYL)PHENYL] 2,4 DIMETHYLBENZAMIDE; N [4 (6 ETHYL 2,3 DIHYDRO 1H THIENO[2,3 B][1,4]THIAZIN 1 YLCARBONYL)PHENYL] 2,6 DICHLOROBENZAMIDE; POTASSIUM CHLORIDE; POTASSIUM ION; RECEPTOR SUBTYPE; THIAZEPINE DERIVATIVE; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG; VASOPRESSIN ANTAGONIST; VASOPRESSIN V1 RECEPTOR; VASOPRESSIN V1A RECEPTOR;

AGONIST; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ELECTROSTIMULATION; GUINEA PIG; HEART BEAT; HEART PAPILLARY MUSCLE; HEART RIGHT ATRIUM; ILEUM; MUSCLE EXCITATION; MUSCLE ISOMETRIC CONTRACTION; MYOMETRIUM; NONHUMAN; PRIORITY JOURNAL; PULMONARY ARTERY; SMOOTH MUSCLE; SMOOTH MUSCLE CONTRACTION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; VASCULAR RING;

EID: 15244357512     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2004.12.008     Document Type: Article

References (46)

1. A. Atke, H. Vilhardt, L. Hauzerova, T. Barth, and L.F. Andersen Effects of the non-peptide inhibitor OPC-21268 and vasopressin stimulation of rat and human myometrium Eur. J. Pharmacol. 281 1995 63 68
2. M. Birnbaumer, A. Seibold, S. Gilbert, M. Ishido, C. Barberis, A. Antaramian, P. Brabet, and W. Rosenthal Molecular cloning of the receptor for human antidiuretic hormone Nature 357 1992 333 335
3. 2 vasopressin receptor antagonist in normal subjects Eur. J. Clin. Pharmacol. 55 1999 633 637
4. 3 pituitary vasopressin receptor FEBS Lett. 356 1994 215 220
5. M. Endoh, M. Takanashi, and I. Norota Effects of vasopressin on phosphoinositide hydrolysis and myocardial contractility Eur. J. Pharmacol. 218 1992 355 358
6. T. Erker Chemistry of thieno-annelated O,N- and S,N-containing heterocyclic compounds. Part 14. Syntheses of thieno[2,3-b][1,4]thiazepine derivatives with calcium antagonistic activity Sci. Pharm. 64 1996 345 352
7. S. Fujisawa, and T. Iijima On the inotropic actions of arginine vasopressin in ventricular muscle of the guinea pig heart Jpn. J. Pharmacol. 81 1999 309 312
8. 2 (OPC-31260) antagonists on the negative inotropic response to vasopressin in isolated dog heart preparations J. Pharmacol. Exp. Ther. 263 1992 627 631
9. 1b vasopressin receptor in rat adrenal medulla Endocrinology 137 1996 3906 3914
10. G. Guillon, D. Butlen, B. Cantau, T. Barth, and S. Jard Kinetic and pharmacological characterization of vasopressin membrane receptors from human kidney medulla: relation to adenylate cyclase activation Eur. J. Pharmacol. 85 1982 291 304
11. J. Howl, T. Ismail, A.J. Strain, C.J. Kirk, D. Anderson, and M. Wheatley Characterization of the human liver vasopressin receptor Biochem. J. 276 1991 189 195
12. J. Howl, X. Wang, C.J. Kirk, and M. Wheatley Fluorescent and biotinylated linear peptides as selective bifunctional ligands for the V1a vasopressin receptor Eur. J. Biochem. 213 1993 711 719
13. 2-receptor is highly laterally mobile in membranes of LLC-PK1 renal epithelial cells at physiological temperature EMBO J. 8 1989 2481 2488
14. S. Jard, R.C. Gaillard, G. Guillon, J. Marie, P. Schoenenberg, A.F. Muller, M. Manning, and W.H. Sawyer Vasopressin antagonists allow demonstration of a novel type of vasopressin receptor in the rat adenohypophysis Mol. Pharmacol. 30 1986 171 177
15. H. Karaki, H. Ozaki, H. Hori, M. Mitsui-Saito, K. Harada, S. Miyamoto, H. Nakazawa, K.J. Won, and K. Sato Calcium movements, distribution, and functions in smooth muscle Pharmacol. Rev. 49 1997 157 230
16. M. Kawamata, M. Mitsui-Saito, T. Kimura, Y. Takayanagi, T. Yanagisawa, and K. Nishimori Vasopressin-induced contraction of uterus is mediated solely by the oxytocin receptor in mice, but not in humans Eur. J. Pharmacol. 472 2003 229 234
17. 2+ sensitisation of smooth muscle contraction through myosin light chain phosphorylation J. Biol. Chem. 266 1991 1708 1715
18. 2+ current in guinea pig ventricular myocytes Pharmacology 59 1999 21 33
19. H. Kuriyama, K. Kitamura, and H. Nabata Pharmacological and physiological significance of ion channels and factors that modulate them in vascular tissues Pharmacol. Rev. 47 1995 387 573
20. F.A. Laszlo, F. Laszlo Jr., and D. De Wied Pharmacology and clinical perspectives of vasopressin antagonists Pharmacol. Rev. 43 1991 73 108
21. C.R. Lee, M.L. Watkins, J.H. Patterson, W. Gattis, C.M. O'Connor, M. Gheorghiade, and K.F. Adams Jr. Vasopressin: a new target for the treatment of heart failure Am. Heart J. 146 1995 9 18
22. 2 receptor and possible link to nephrogenic diabetes insipidus Nature 357 1992 336 339
23. S.C. Mah, and K.G. Hofbauer Antagonists of arginine-vasopressin: experimental and clinical applications Drugs Future 12 1987 1055 1070
24. 2 receptors: synthesis and pharmacological properties of 4-(1,4,5,6-tetrahydroimidazol[4′,5-d][1]benzoazepine-6-carbonyl) benzanailide derivatives and 4′-(5,6-dihydro-4H-thiazolo[5,4-d][1] benzoazepine-6-carbonyl)benzanilide derivatives Chem. Pharm. Bull. 48 2000 21 31
25. 1a arginine vasopressin receptor Nature 356 1992 523 526
26. M. Naitoh, H. Suzuki, M. Murakami, A. Matsumoto, K. Arakawa, A. Ichihara, H. Nakamoto, K. Oka, Y. Yamamura, and T. Saruta Effects of oral AVP receptor antagonists OPC-21268 and OPC-31260 on congestive heart failure in conscious dogs Am. J. Physiol. 267 1994 H2245 H2254
27. C. Paulmier, and F. Outurquin Thienyl- and selenienylthiocyanates and selenocyanates. 4. Synthesis of thieno[2,3-d]thiazoles, thieno[2,3-e]thiazines and several selenophene analogs J. Heterocycl. Chem. 20 1983 113 119
28. 2 selective ligands Endocrinology 126 1990 1478 1484
29. 1a receptors J. Clin. Invest. 92 1993 224 231
30. 1a antagonist, on human vascular smooth muscle cells Am. J. Physiol. 268 1995 404 410
31. C. Serradeil-Le Gal An overview of SR121463, a selective non-peptide vasopressin (2) receptor antagonist Cardiovasc. Drug Rev. 19 2001 H201 H214
32. I.E. Schoemaker, A.L. Meulemans, L.J. Andries, and D.L. Brutsaert Role of endocardial endothelium in positive inotropic action of vasopressin Am. J. Physiol. 259 1990 H1148 H1151
33. M. Steinwall, T. Bossmar, C. Gaud, and M. Akerlund Inhibitory effects of SR 49059 on oxytocin- and vasopressin-induced uterine contractions in non-pregnant women Acta Obstet. Gynecol. Scand. 83 2004 12 18
34. 1b vasopressin receptor J. Biol. Chem. 269 1994 27088 27092
35. 2 receptor antagonist, in vitro and in vivo J. Pharmacol. Exp. Ther. 282 1997 301 308
36. M. Thibonnier, P. Coles, A. Thibonnier, and M. Shoham Molecular pharmacology and modelling of vasopressin receptors Prog. Brain Res. 139 2002 179 196
37. M. Thibonnier Vasopressin receptor antagonists in heart failure Curr. Opin. Pharmacol. 3 2003 683 687
38. M. Thibonnier, and J.M. Roberts Characterization of human platelet vasopressin receptors J. Clin. Invest. 76 1985 1857 1864
39. 1a vasopressin receptor J. Biol. Chem. 269 1994 3304 3310
40. 2 receptor antagonist Eur. J. Pharmacol. 446 2002 129 138
41. 2-vasopressinergic receptors Am. J. Phys. 255 1988 H261 H265
42. 1 subtype receptors Circ. Res. 69 1991 239 245
43. i in guinea pig papillary muscles Jpn. J. Pharmacol. 68 1995 217 221
44. 1 receptor antagonist Science 252 1991 572 574
45. 2 receptor antagonist Br. J. Pharmacol. 105 1992 787 791
46. 2 receptor antagonist, in dogs with pacing-induced congestive heart failure Eur. J. Pharmacol. 376 1999 239 246