Rigidified 2-aminopyrimidines as histamine H4 receptor antagonists: Effects of substitution about the rigidifying ring

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 6, 2010, Pages 1900-1904

  Koenig, John R ^a   Liu, Huaqing ^a   Drizin, Irene ^a   Witte, David G ^a   Carr, Tracy L ^a   Manelli, Arlene M ^a   Milicic, Ivan ^a   Strakhova, Marina I ^a   Miller, Thomas R ^a   Esbenshade, Timothy A ^a   Brioni, Jorge D ^a   Cowart, Marlon ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Histamine; Histamine H4 receptor

Indexed keywords

AMINOPYRIMIDINE DERIVATIVE; HISTAMINE H4 RECEPTOR; HISTAMINE H4 RECEPTOR ANTAGONIST; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PROTEIN MOTIF; PRURITUS; RECEPTOR BINDING; SCRATCHING;

AMINOPYRIDINES; ANIMALS; HISTAMINE ANTAGONISTS; HUMANS; MICE; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, HISTAMINE;

EID: 77549085138     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.131     Document Type: Article

References (23)

1. Engelhardt H., Smits R.A., Leurs R., Haaksma E., and de Esch I.J.P. Curr. Opin. Drug Discovery Dev. 12 (2009) 628
2. Akdis C.A., Estelle F., and Simons R. Eur. J. Pharmacol. 533 (2006) 69
3. de Esch I.J.P., Thurmond R.L., Jongejan A., and Leurs R. Trends Pharmacol. Sci. 26 (2005) 462
4. Damaj B.B., Becerra C.B., Esber H.J., Wen Y., and Maghazachi A.A. J. Immunol. 179 (2007) 7907
5. Zhang M., Thurmond R.L., and Dunford P.J. Pharmacol. Ther. 113 (2007) 594
6. Ling P., Ngo K., Nguyen S., Thurmond R.L., Edwards J.P., Karlsson L., and Fung-Leung W.P. Br. J. Pharmacol. 142 (2004) 161
7. Buckland K.F., Williams T.J., and Conroy D.M. Br. J. Pharmacol. 140 (2003) 1117
8. O' Reilly M., Alpert R., Jenkinson S., Gladue R.P., Foo S., Trim S., Peter B., Trevethick M., and Fidock M. J. Recept. Signal Trans. 22 1-4 (2002) 431
9. Dunford P.J., Williams K.N., Desai P.J., McQueen D., Karlsson L., and Thurmond R. J. Allergy Clin. Immunol. 119 (2007) 176
10. Rees J., and Murray C.S. Clin. Exp. Dermatol. 30 (2005) 471
11. Thurmond R.L., Gelfand E.W., and Dunford P.J. Nat. Rev. Drug Disc. 7 (2008) 41
12. Bell J.K., McQueen D.S., and Rees J.L. Br. J. Pharmacol 142 (2004) 374
13. Dunford P.J., O'Donnell N., Riley J.P., Williams K.N., Karlsson L., and Thurmond R.L. J. Immun. 176 (2006) 7062
14. Altenbach R.J., Adair R.M., Bettencourt B.M., Black L.A., Fix-Stenzel S.R., Gopalakrishnan S.M., Hsieh G.C., Liu H., Marsh K.C., McPherson M.J., Milicic I., Miller T.R., Vortherms T.A., Warrior U., Wetter J.M., Wishart N., Witte D.G., Honore P., Esbenshade T.A., Hancock A.A., Brioni J.D., and Cowart M.C. J. Med. Chem. 51 (2008) 6571
15. Cowart M.C., Altenbach R.J., Liu H., Hsieh G.C., Drizin I., Milicic I., Miller T.R., Witte D.G., Wishart N., Fix-Stenzel S.R., McPherson M.J., Adair R.M., Wetter J.M., Bettencourt B.M., Marsh K.C., Sullivan J.P., Honore P., Esbenshade T.A., and Brioni J.D. J. Med. Chem. 51 (2008) 6547
16. Liu H., Altenbach R.J., Carr T.L., Chandran P., Hsieh G.C., Lewis L.R., Manelli A.M., Milicic I., Marsh K.C., Miller T.R., Strakhova M.I., Vortherms T.A., Wakefield B.D., Wetter J.M., Witte D.G., Honore P., Esbenshade T.A., Brioni J.D., and Cowart M.D. J. Med. Chem. 51 (2008) 7094
17. Coruzzi G., Adami M., Guaita E., de Esch I.J.P., and Leurs R. Eur. J. Pharmacol. 563 (2007) 240
18. Thurmond R.L., Desai P.J., Dunford P.J., Fung-Leung W.P., Hofstra C.L., Jiang W., Nguyen S., Riley J.P., Sun S., Williams K.N., Edwards J.P., and Karlsson L. J. Pharmacol. Exp. Ther. 309 (2004) 404
19. Bartelt R.J., Weisleder D., and Momany F.A. Synthesis (2003) 117
20. Liu C., Wilson S.J., Kuei C., and Lovenberg T.W. J. Pharmacol. Exp. Ther. 299 (2001) 121
21. For example, comparison of log D values measured at pH 7.4-1: 1.73 versus 28: 2.20; 8:2.05 versus 30: 1.60.
22. Esbenshade T.A., Krueger K.M., Miller T.R., Kang C.H., Denny L.I., Witte D.G., Yao B.B., Fox G.B., Faghih R., Bennani Y.L., Williams M., and Hancock A.A. J. Pharmacol. Exp. Ther. 305 (2003) 887
23. Alguacil L.F., and Perez-Garcia C. Curr. Drug Targets CNS Neurol. Disord. 2 (2003) 303