Tetrahydroquinoline derivatives as CRTH2 antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 24, 2009, Pages 6840-6844

  Liu, Jiwen ^a   Wang, Yingcai ^a   Sun, Ying ^a   Marshall, Derek ^a   Miao, Shichang ^a   Tonn, George ^a   Anders, Penny ^a   Tocker, Joel ^a   Tang, H Lucy ^a   Medina, Julio ^a  

^a AMGEN INC   (United States)

Author keywords

Allergic diseases; Antagonists; CRTH2; GPCR; Lead optimization; PGD2; SAR; Tetrahydroquinoline

Indexed keywords

CHEMOATTRACTANT RECEPTOR HOMOLOGOUS MOLECULE EXPRESSED ON TH2 CELLS; G PROTEIN COUPLED RECEPTOR; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG BIOAVAILABILITY; DRUG POTENCY; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; MALE; NONHUMAN; RAT;

ANTI-ALLERGIC AGENTS; CELL LINE; CELL SHAPE; DRUG DISCOVERY; EOSINOPHILS; HUMANS; QUINOLINES; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PROSTAGLANDIN;

EID: 71849102580     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.094     Document Type: Article

References (29)

1. Lewis R.A., Soter N.A., Diamond P.T., Austen K.F., Oates J.A., and Roberts L.J. J. Immunol. 129 (1982) 1627
2. Holgate S.T., Burns G.B., Robinson C., and Church M.K. J. Immunol. 133 (1984) 2138
3. Gundel R.H., Kinkade P., Torcellini C.A., Clarke C.C., Watrous J., Desai S., Homon C.A., Farina P.R., and Wegner C.D. Am. Rev. Respir. Dis. 144 (1991) 76
4. Nagata K., Hirai H., Tanaka K., Ogawa K., Aso T., Sugamura K., Nakamura M., and Takano S. FEBS Lett. 459 (1999) 195
5. Nagata K., Tanaka K., Ogawa K., Kemmotsu K., Imai T., Yoshie O., Abe H., Tada K., Nakamura M., Sugamura K., and Takano S. J. Immunol. 162 (1999) 1278
6. Cosmi L., Annunziato F., Galli M.I.G., Maggi R.M.E., Nagata K., and Romagnani S. Eur. J. Immunol. 30 (2000) 2972
7. Miadonna A., Tedeschi A., Brasca C., Folco G., Sala A., and Murphy A. J. Allergy Clin. Immunol. 85 (1990) 906
8. Turner N.C., Fuller R.W., and Jackson D.M. J. Lipid. Mediators Cell Signalling 11 (1995) 93
9. Hirai H., Tanaka K., Yoshie O., Ogawa K., Kenmotsu K., Takamori Y., Ichimasa M., Sugamura K., Nakamura M., Takano S., and Nagata K. J. Exp. Med. 193 (2001) 255
10. Sugimoto H., Shichijo M., Iino T., Manabe Y., Watanabe A., Shimazaki M., Gantner F., and Bacon K.B. J. Pharmacol. Exp. Ther. 305 (2003) 347
11. Monneret G., Gravel S., Diamond M., Rokach J., and Powell W.S. Blood 98 (2001) 1942
12. Gosset P., Bureau F., Angeli V., Pichavant M., Faveeuw C., Tonnel A.B., and Trottein F. J. Immunol. 170 (2003) 4943
13. Liu J., Fu Z., Wang Y., Schmitt M., Huang A., Marshall D., Tonn G., Seitz L., Sullivan T., Tang H.L., Collins T., and Medina J. Bioorg. Med. Chem. Lett. (2009) 10.1016/j.bmcl.2009.09.052
14. Ghosh, S.; Elder, A. M.; Carson, K. G.; Sprott, K.; Harrison, S. WO Patent 032848, 2004.
15. Ghosh, S.; Elder, A. M.; Carson, K. G.; Sprott, K.; Harrison, S. J.; Hicks, F. A.; Renou, C. C.; Reynolds, D. WO Patent 100321, 2005.
16. Kuhn, C.; Feru, F.; Bazin, M.; Awad, M.; Goldstein, S. W. EP Patent 1413306, 2004.
17. Kotera, O.; Oshima, E.; Ueno, K.; Ikemura, T.; Manabe, H.; Sawada, M.; Mimura, H.; Miyaji, H.; Nonaka, H. WO Patent 052863, 2004.
18. Inman, W.; Liu, J.; Medina, J. C.; Miao, S. WO Patent 007094, 2005.
19. Mimura H., Ikemura T., Kotera O., Sawada M., Tashiro S., Fuse E., Ueno K., Manabe H., Ohshima E., Karasawa A., and Miyaji H. J. Pharmacol. Exp. Ther. 314 (2005) 244
20. 50) was determined. The binding buffer contains either 0.5% BSA (buffer binding) or 50% human plasma (plasma binding).
21. 50 of the compounds determined.
22. Forrest T.P., Dauphinee G.A., and Miles W.F. Can. J. Chem. 52 (1974) 884
23. Funabashi M., Iwakawa M., and Yoshimura J. Bull. Chem. Soc. Jpn. 42 (1969) 2885
24. Ma D., and Xia C. Org. Lett. 3 (2001) 2583
25. Ma D., Xia C., Jiang J., Zhang J., and Tang W. J. Org. Chem. 68 (2003) 442
26. Chiral HPLC conditions: column: ChiralPak AD-H, 20 × 250 mm; solvents: 40% isopropanol/hexanes; flow rate: 20 mL/min.
27. Zhi L., Tegley C.M., Marschke K.B., and Jones T.K. Bioorg. Med. Chem. Lett. 9 (1999) 1009
28. 50 in the two experiments was 0.20 nM.
29. 50) was determined. The binding buffer contains either 0.5% BSA (buffer binding).