Aminomethylpiperazines as selective urotensin antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 16, 2008, Pages 4470-4473

  Hilfiker, Mark A ^a   Zhang, Daohua ^a   Dowdell, Sarah E ^a   Goodman, Krista B ^a   McAtee, John J ^a   Dodson, Jason W ^a   Viet, Andrew Q ^a   Wang, Gren Z ^a   Sehon, Clark A ^a   Behm, David J ^a   Wu, Zining ^b   Carballo, Luz H ^b   Douglas, Stephen A ^a   Neeb, Michael J ^a  

^a GLAXOSMITHKLINE   (United States)

^b Mathematical and Information Science Directorate Army Research Office   (United States)

Author keywords

7 TM; Hypertension; Kappa; Opioid; Piperazine; Urotensin

Indexed keywords

4 [(3,4 DICHLOROPHENYL)ACETYL] 3 (1 PYRROLIDINYLMETHYL) 1 PIPERAZINECARBOXYLIC ACID METHYL ESTER; AMINOMETHYLPIPERAZINE; BRL 52537; KAPPA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR AGONIST; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG; UROTENSIN;

ARTICLE; BINDING AFFINITY; HYPERTENSION; NONHUMAN; RAT; VASCULAR RING; VASOCONSTRICTION;

ANIMALS; AORTA; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; HYPERTENSION; MODELS, CHEMICAL; PIPERAZINES; RATS; RECEPTORS, OPIOID, KAPPA; STRUCTURE-ACTIVITY RELATIONSHIP; TAURINE; UROTENSINS;

RATTUS;

EID: 48649096711     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.07.067     Document Type: Article

References (55)

1. Bern H.A., and Lederis K. J. Endocrinol. 45 (1969) xi
2. Bern H.A., Pearson D., Larson B.A., and Nishioka R.S. Recent Prog. Horm. Res. 41 (1985) 533
3. Ichikawa T., McMaster D., Lederis K., and Koyabashi H. Peptides 3 (1982) 859
4. Loretz C.A., Howard M.E., and Siegel A.J. J. Physiol. 249 (1985) G284
5. For a recent review, see:. Dhanak D., Neeb M.J., and Douglas S.A. Annu. Rep. Med. Chem. 38 (2003) 99
6. Ames R.S., Sarau H.M., Chambers J.K., Willette R.N., Aiyar N.V., Romanic A.M., Louden C.S., Foley J.J., Sauermelch C.F., Coatney R.W., Ao Z., Disa J., Holmes S.D., Stadel J.M., Martin J.D., Liu W.S., Glover G.I., Wilson S., McNulty D.E., Ellis C.E., Elshourbagy N.A., Shabon U., Trill J.J., Hay D.W., Ohlstein E.H., Bergsma D.J., and Douglas S.A. Nature 401 (1999) 282
7. Behm D.J., Doe C.P., Johns D.G., Maniscalco K., Stankus G.P., Wibberley A., Willette R.N., and Douglas S.A. Naunyn Schmiedebergs Arch. Pharmacol. 369 (2004) 274
8. Böhm F., and Pernow J. Br. J. Pharmacol. 135 (2002) 25
9. Kemp W., Roberts S., Komesaroff P., Zomer E., and Krum H. Scand. J. Gastroenterol. 43 (2008) 103
10. Russell F.D., Meyers D., Galbraith A.J., Bett N., Toth I., Kearns P., and Molenaar P. Am. J. Physiol. 285 (2003) H1576
11. Song W., Ashton N., and Balment R.J. J. Physiol. 552P (2003) P107
12. Douglas S.A., Dhanak D., and Johns D.G. Trends Pharmacol. Sci. 25 (2004) 76
13. Matsushita M., Shichiri M., Imai T., Iwashina M., Tanaka H., Takasu N., and Hirata Y. J. Hypertens. 19 (2001) 2185
14. Cheung B.M., Leung R., Man Y.B., and Wong L.Y. J. Hypertens. 22 (2004) 1341
15. Sondermeijer B., Kompa A., Komesaroff P., and Krum H. Am. J. Hypertens. 18 (2005) 1195
16. Douglas S.A., Tayara L., Ohlstein E.H., Halawa N., and Giaid A. Lancet 359 (2002) 1990
17. Ng L.L., Loke I., O'Brien R.J., Squire I.B., and Davies J.E. Circulation 106 (2002) 2877
18. Richards A.M., Nicholls M.G., Lainchbury J.G., Fisher S., and Yandle T.G. Lancet 360 (2002) 545
19. Lapp H., Boerrigter G., Costello-Boerrigter L.C., Jaekel K., Scheffold T., Krakau I., Schramm M., Guelker H., and Stasch J.P. Int. J. Cardiol. 94 (2004) 93
20. Lim M., Honisett S., Sparkes C., Komesaroff P., Kompa A., and Krum H. Circulation 109 (2004) 1212
21. Bousette N., Patel L., Douglas S.A., Ohlstein E.H., and Giaid A. Atherosclerosis 176 (2004) 117
22. Maguire J.J., Kuc R.E., Wiley K.E., Kleinz M.J., and Davenport A.P. Peptides 25 (2004) 1767
23. Totsune K., Takahashi K., Arihara Z., Sone M., Satoh F., Ito S., Kimura Y., Sasano H., and Murakami O. Lancet 358 (2001) 810
24. Shenouda A., Douglas S.A., Ohlstein E.H., and Giaid A. J. Histochem. Cytochem. 50 (2002) 885
25. Langham R.G., Gow R., Thomson N.M., Dowling J.K., and Gilbert R.E. Am. J. Kidney Dis. 44 (2004) 826
26. Totsune K., Takahashi K., Arihara Z., Sone M., Satoh F., Ito S., and Murakami O. Clin. Sci. 104 (2003) 1
27. Wenyi Z., Suzuki S., Hirai M., Hinokio Y., Tanizawa Y., Matsutani A., Satoh J., and Oka Y. Diabetologia 46 (2003) 972
28. Flohr S., Kurz M., Kostenis E., Brkovich A., Fournier A., and Klabunde T. J. Med. Chem. 45 (2002) 1799
29. Croston G.E., Olsson R., Currier E.A., Burstein E.S., Weiner D., Nash N., Severance D., Allenmark S.G., Thunberg L., Ma J., Mohell N., O'Dowd B., Brann M.R., and Hacksell U. J. Med. Chem. 45 (2002) 4950
30. Clozel M., Binkert C., Birker-Robaczewska M., Boukhadra C., Ding S., Fischli W., Hess P., Mathys B., Morrison K., Mueller C., Mueller C., Nayler O., Qiu C., Rey M., Scherz M., Velker J., Weller T., Xi J., and Ziltener P. J. Pharmacol. Exp. Ther. 311 (2004) 204
31. Luci D., Ghosh S., Smith C., Qi J., Wang Y., Haertlein B., Parry T., Li J., Almond H., Minor L., Damiano B., Kinney W., Maryanoff B., and Lawson E. Bioorg. Med. Chem. Lett. 17 (2007) 6489
32. For patents, see Ref. 3.
33. Binding affinity data were measured using a [125I]hU-II radioligand binding assay with HEK293 cell membranes stably expressing human recombinant UT receptors. For detailed assay conditions, see: Dhanak, D.; Knight, S. D.; Jin, J.; Keenan, R. M. WO Patent 2001045711-A1, 2001; Chem. Abstr. 2001, 135, 76785.
34. Dhanak, D.; Knight, S. D.; Warren, G. L.; Jin, J.; Widdowson, K. L.; Keenan, R. M. WO Patent 2001045710-A1, 2001; Chem. Abstr. 2001, 135, 71313.
35. Jin J., Wang Y., Wang F., Shi D., Erhard K.F., Wu Z., Guida B.F., Lawrence S.K., Behm D.J., Disa J., Vaidya K.S., Evans C., McMillan L.J., Rivero R.A., Neeb M.J., and Douglas S.A. Bioorg. Med. Chem. Lett. 18 (2008) 2860
36. 35S]GTPgammaS binding assay measured by LEADseeker SPA (384 well) using membranes from Bacmam transducted CHO-K1 cells expressing the human κ-opioid receptor. For detailed assay conditions, see:. Lamonte N., Echo J.A., Ackerman T.F., Christian G., and Bodnar R.J. Brain Res. 929 (2002) 96
37. Minami M., and Masamichi S. Neurosci. Res. 23 (1995) 121
38. Millan M.J. Trends Pharmacol. Sci. 11 (1990) 70
39. Cowan A., and Gmerek D.E. Trends Pharmacol. Sci. 7 (1986) 69
40. Colle R., Clarke G.D., Dondio G., Giardina G., Petrone G., Sbacchi M., and Vecchietti V. Chirality 4 (1992) 8
41. Scopes D.I.C., Hayes N.F., Bays D.E., Belton D., Brain J., Brown D.S., Judd D.B., McElroy A.B., Meerholz C.A., et al. J. Med. Chem. 35 (1992) 490
42. Subramanian G., Paterlini M.G., Larson D.L., Portoghese P.S., and Ferguson D.M. J. Med. Chem. 41 (1998) 4777
43. Vecchietti V., Giordani A., Giardina G., Colle R., and Clarke G.D. J. Med. Chem. 34 (1991) 397
44. Scopes D.I.C., Hayes N.F., Bays D.E., Belton D., Brain J., Brown D.S., Judd D.B., McElroy A.B., Meerholz C.A., Naylor A., Hayes A.G., Sheehan M.J., Birch P.J., and Tyers M.B. J. Med. Chem. 35 (1992) 490
45. Okada, T.; Takahashi, Y.; Chiba, R.; Takahashi, K.; Nagao, Y.; Iwase, N.; Koumoto, T. WO Patent 2004074277 A1, 2004; Chem. Abstr. 2004, 141, 225540.
46. Kumar, V.; Guo, D.; Marella, M. A.; Maycock, A. L. US Patent 2003/0144272 A1, 2003; Chem. Abstr. 2003, 139, 149650.
47. Ravert H.T., Scheffel U., Mathews W.B., Musachio J.L., and Dannals R.F. Nucl. Med. Biol. 29 (2002) 47
48. Zhang, W. Y.; Maycock, A. L.; Marella, M. A.; Kumar, V.; Gaul, F.; Chang, A.-C.; Guo, D. US Patent 6,303,611 B1, 2001; Chem. Abstr. 2001, 135, 318517.
49. Hayes A.G., Birch P.J., Hayward N.J., Sheehan M.J., Rogers H., Tyers M.B., Judd D.B., Scopes D.I.C., and Naylor A. J. Pharmacol. Exp. Ther. 101 (1990) 944
50. Naylor A., Judd D.B., Lloyd J.E., Scopes D.I.C., Hayes A.G., and Birch P.J. J. Med. Chem. 36 (1993) 2075
51. Birch P.J., Rogers H., Hayes A.G., Hayward N.J., Tyers M.B., Scopes D.I.C., Naylor A., and Judd D.B. Br. J. Pharmacol. 103 (1991) 1819
52. Chan D.M.T., Manaco K.L., Wang R., and Winters M.P. Tetrahedron Lett. 39 (1998) 2933
53. Evans D.A., Katz J.L., and West T.R. Tetrahedron Lett. 39 (1998) 2937
54. Cundy D.J., and Forsyth S.A. Tetrahedron Lett. 39 (1998) 7979
55. Douglas S.A., Behm D.J., Aiyar N.V., Naselsky D., Disa J., Brooks D.P., Ohlstein E.H., Gleason J.G., Sarau H.M., Foley J.J., Buckley P.T., Schmidt D.B., Wixted W.E., Widdowson K., Riley G., Jin J., Gallagher T.F., Schmidt S.J., Ridgers L., Christmann L.T., Keenan R.M., Knight S.D., and Dhanak D. Br. J. Pharmacol. 145 (2005) 620