Potent and orally bioavailable CCR4 antagonists: Synthesis and structure-activity relationship study of 2-aminoquinazolines

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 1, 2009, Pages 64-73

  Yokoyama, Kazuhiro ^a   Ishikawa, Noriko ^a   Igarashi, Susumu ^a   Kawano, Noriyuki ^a   Masuda, Naoyuki ^a   Hamaguchi, Wataru ^a   Yamasaki, Shingo ^a   Koganemaru, Yohei ^a   Hattori, Kazuyuki ^a   Miyazaki, Takahiro ^a   Ogino, Shin ichi ^a   Matsumoto, Yuzo ^a   Takeuchi, Makoto ^a   Ohta, Mitsuaki ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

2 Aminoquinazolines; Chemokine receptor 4 (CCR4) antagonists; Inflammatory disease

Indexed keywords

2 AMINOQUINAZOLINE DERIVATIVE; [1' [4 [(4 CHLOROPHENYL)AMINO] 6,7 DIMETHOXYQUINAZOLIN 2 YL] 1,4' BIPIPERIDIN 3 YL]METHANOL; CHEMOKINE RECEPTOR CCR5 ANTAGONIST; CHEMOTAXIS INHIBITOR; N (4 CHLOROPHENYL) 6,7 DIMETHOXY 2 (4 PYRROLIDIN 1 YLPIPERIDIN 1 YL)QUINAZOLIN 4 AMINE; OXAZOLONE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMOTAXIS; CONTACT ALLERGY; CONTROLLED STUDY; DERMATITIS; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; AMINES; ANIMALS; ANTI-INFLAMMATORY AGENTS; CHEMOTAXIS; DERMATITIS; DISEASE MODELS, ANIMAL; HUMANS; MICE; PIPERIDINES; QUINAZOLINES; RECEPTORS, CCR4; STRUCTURE-ACTIVITY RELATIONSHIP;

MURINAE;

EID: 57649229431     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.020     Document Type: Article

References (32)

1. Rossi D., and Zlotnik A. Annu. Rev. Immunol. 18 (2000) 217
2. Owen C. Pulm. Pharmacol. Ther. 12 (2001) 121
3. Murphy M.P., Baggiolini M., Charo F.I., Hebert A.C., Horuk R., Matsushima K., Miller H.L., Oppenheim J.J., and Power A.C. Pharmacol. Rev. 52 (2000) 145
4. Zlotnik A., and Yoshie O. Immunity 12 (2000) 121
5. Hoogewerf J.A., Black D., Proudfoot I.E.A., Wells C.N.T., and Power A.C. Biochem. Biophys. Res. Comm. 218 (1996) 337
6. Sallusto F., Lenig D., Mackay R.C., and Lanzavecchia A. J. Exp. Med. 187 (1998) 875
7. Andrew P.D., Ruffing N., Kim H.C., Miao W., Heath H., Li Y., Murphy K., Campbell J.J., Butcher C.E., and Wu L. J. Immunol. 166 (2001) 103
8. Kim H.C., Rott L., Kunkel J.E., Genovese C.M., Andrew P.D., Lijun Y., and Butcher C.E. J. Clin. Invest. 108 (2001) 1331
9. Katschke Jr. J.K., Rottman B.J., Ruth H.J., Qin S., Wu L., LaRosa G., Ponath P., Park C.C., Pope M.R., and Koch E.A. Arthritis Rheum. 44 (2001) 1022
10. Campbell J.J., Haraldsen G., Pan J., Rottman J., Qin S., Panath P., Andrew P.D., Warnke R., Ruffig N., Kassam N., Wu L., and Butcher C.E. Nature 400 (1999) 776
11. Imai T., Baba M., Nishimura M., Kakizaki M., Takagi S., and Yoshie O. J. Biol. Chem. 272 (1997) 15036
12. Imai T., Yoshida T., Baba M., Nishimura M., Kakizaki M., and Yoshie O. J. Biol. Chem. 271 (1996) 21514
13. Godiska R., Chantry D., Raport J.C., Sozzani S., Allavena P., Leviten D., Mantovani A., and Gray W.P. J. Exp. Med. 185 (1997) 1595
14. Mantrovani A. Immunol. Today 20 (1999) 254
15. Papina-Bordignon P., Papi A., Mariani M., Lucia D.P., Casoni G., Bellettato C., Buonsanti C., Miotto D., Mapp C., Villa A., Arrigoni G., Fabbri M.L., and Sinigaglia F. J. Clin. Invest. 107 (2001) 1357
16. Vestergaard C., Bang K., Gesser B., Yoneyama H., Matsushima K., and Larsen G.C. J. Invest. Dermat. 115 (2000) 640
17. Rottman B.J., Smith L.T., Ganley G.K., Kikuchi T., and Krueger G.J. Lab. Invest. 81 (2001) 335
18. Ruth H.J., Rottman B.J., Katschke Jr. J.K., Qin S., Wu L., LaRosa G., Panath P., Pope M.R., and Koch E.A. Arthritis Rheum. 44 (2001) 2750
19. Jo Y., Matsumoto T., Yada S., Fujisawa K., Esaki M., Onai N., Matsushima K., and Iida M. Clin. Exp. Immunol 132 (2003) 332
20. Gonzalo J.A., Pan Y., Lloyd C.M., Jia G.Q., Yu G., Dussault B., Powers C.A., Proudfoot A.E., Coyle A.J., Gearing D., and Gutierrzez-Ramos J.C. J. Immunol. 163 (1999) 403
21. Kawasaki S., Takizawa H., Yoneyama H., Nakayama T., Fujisawa R., Izumizaki M., Imai T., Yoshie O., Momma I., Yamamoto K., and Matsushima K. J. Immunol. 166 (2001) 2055
22. Yokoyama K., Ishikawa N., Igarashi S., Kawano N., Hattori K., Miyazaki T., Ogino S., Matsumoto Y., Takeuchi M., and Ohta M. Bioorg. Med. Chem. 16 (2008) 7021
23. Yokoyama K., Ishikawa N., Igarashi S., Kawano N., Masuda N., Hattori K., Miyazaki T., Ogino S., Orita M., Matsumoto Y., Takeuchi M., and Ohta M. Bioorg. Med. Chem. 16 (2008) 7968
24. Miyashita A., Matsuda H., Iijima C., and Higashino T. Chem. Pharm. Bull. 38 (1990) 1147
25. Obach R.S. Drug Metab. Dispos. 27 (1999) 1350
26. Tarayre P.J., Barbara M., Aliga M., and Tisne-Versailles J. Drug Res. 40 (1990) 1125
27. Ottosen R.E., Sørensen D.M., Björkling F., Skak-Nielseen T., Fjording S.M., Aaes H., and Binderup L. J. Med. Chem. 46 (2003) 5651 Prednisolone was administered subcutaneously to mice previously sensitized to oxazolone in accordance with our method described above (see Section 6.2.4). A 50% inhibition in ear swelling was observed at the 10 mg/kg dose.
28. Allegretti M., Berdini V., Cesta C.M., Curti R., Nicolini L., and Topai A. Tetrahedron Lett. 42 (2001) 4257
29. Barkenbus C., and Wuellner A.J. J. Am. Chem. Soc. 77 (1955) 3866
30. Mizuhara S., and Nagata S. Nucleic Acids Res. 18 (1990) 11
31. Imai T., Chantry D., Raport CJ., Wood CL., Nishimura M., Godiska R., Yoshie O., and Gray PW. J. Biol. Chem. 273 (1998) 1764
32. Boyden S. J. Exp. Med. 115 (1962) 453