Optimization of sulfonamide derivatives as highly selective EP1 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 23, 2006, Pages 7774-7789

  Naganawa, Atsushi ^a   Matsui, Toshiaki ^a   Ima, Masaki ^a   Yoshida, Koji ^a   Tsuruta, Hiroshi ^a   Yamamoto, Shingo ^a   Yamamoto, Hiroshi ^a   Okada, Hiroki ^a   Maruyama, Takayuki ^a   Nakai, Hisao ^a   Kondo, Kigen ^a   Toda, Masaaki ^a  

^a ONO PHARMACEUTICAL CO   (Japan)

Author keywords

Antagonist; EP1 receptor; Prostaglandin; Sulfonamide

Indexed keywords

2 CHLORO 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 5 (TRIFLUOROMETHYL)PHENOXY]METHYL]BENZOIC ACID; 3 CHLORO 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 5 (TRIFLUOROMETHYL)PHENOXY]METHYL]BENZOIC ACID; 4 [[2 [ISOBUTYL(1,3 THIAZOL 2 YLSULFONYL)AMINO] 4,5 DIMETHYLPHENOXY]METHYL] 3 METHYLBENZOIC ACID; 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 4,5 DIMETHYLPHENOXY] METHYL] 3 METHYLBENZOIC ACID; 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 4,5 DIMETHYLPHENOXY] METHYL]BENZOIC ACID; 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 5 (TRIFLUOROMETHYL) PHENOXY]METHYL] 3 METHYLBENZOIC ACID; 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 5 (TRIFLUOROMETHYL) PHENOXY]METHYL] 3,5 DIMETHYLBENZOIC ACID; 4 [[2 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 5 METHYLPHENOXY]METHYL] BENZOIC ACID; 4 [[[3 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 2 NAPHTHYL)OXY]METHYL] BENZOIC ACID; 4 [[[3 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 5,6,7,8 TETRAHYDRONAPHTHALEN 2 YL]OXY]METHYL]BENZOIC; 4 [[[6 [ISOBUTY[(5 METHYL 2 FURYL)SULFONYL]AMINO] 2,3-DIHYDRO 1H INDEN 5 YL]OXY]METHYL] 3 METHYLBENZOIC ACID; 4 [[[6 [ISOBUTYL(1,3 THIAZOL 2 YLSULFONYL)AMINO] 2,3 DIHYDRO 1H INDEN 5 YL]OXY]METHYL] 3 METHYLBENZOIC; 4 [[[6 [ISOBUTYL(1,3 THIAZOL 2 YLSULFONYL)AMINO] 2,3 DIHYDRO 1H INDEN 5 YL]OXY]METHYL]BENZOIC ACID; 4 [[[6 [ISOBUTYL[(5 METHYL 2 FURYL)SULFONYL]AMINO] 2,3 DIHYDRO 1H INDEN 5 YL]OXY]METHYL]BENZOIC ACID; CYTOCHROME P450 ISOENZYME; DICLOFENAC; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; SULFONAMIDE; SULPROSTONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; BLADDER PRESSURE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; ENZYME INHIBITION; FEMALE; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

BENZOIC ACIDS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; LIVER; PROTEIN BINDING; RECEPTORS, PROSTAGLANDIN E; RECEPTORS, PROSTAGLANDIN E, EP1 SUBTYPE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 33750051977     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.08.001     Document Type: Article

References (33)

1. Coleman R.A., Smith W.L., and Narumiya S. Pharmacol. Rev. 46 (1994) 205
2. Ruel R., Lacombe P., Abramovitz M., Godbout C., Lamontagne S., Rochette C., Sawyer N., Stocco R., Tremblay N.M., Metters K.M., and Labelle M. Bioorg. Med. Chem. Lett. 9 (1999) 2699
3. Hallinan E.A., Tsymbalov H.S., Stapelfeld A., and Savage M.A. Bioorg. Med. Chem. 9 (2001) 1
4. Ducharme Y.D., Blouin M., Carrière M.-C., Chateauneuf A., Côté B., Denis D., Frenette R., Greig G., Kargman S., Lamontagne S., Martins E., Nantel F., O'Neill G., Sawyer N., Matters K.M., and Friesen R.W. Bioorg. Med. Chem. Lett. 15 (2005) 1155
5. Hall A., Bit R.A., Brown S.H., Chaignot H.M., Chessell I.P., Coleman T., Giblin G.M.P., Hurst D.N., Kilford I.R., Lewell X.Q., Michel A.D., Mohamed S., Naylor A., Novelli R., Skinner L., Spalding D.J., Tang S.P., and Wilson R.J. Bioorg. Med. Chem. Lett. 16 (2006) 2666
6. Tani K., Naganawa A., Ishida A., Egashira H., Sagawa K., Harada H., Ogawa M., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. Lett. 11 (2001) 2025
7. Tani K., Naganawa A., Ishida A., Sagawa K., Harada H., Ogawa M., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 1093
8. Tani K., Naganawa A., Ishida A., Egashira H., Sagawa K., Harada H., Ogawa M., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 1107
9. Tani K., Naganawa A., Ishida A., Egashira H., Odagaki Y., Miyazaki T., Hasegawa T., Kawanaka Y., Sagawa K., Harada H., Ogawa M., Maruyama T., Nakai H., Ohuchida S., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 1883
10. Maruyama T., Asada M., Shiraishi T., Ishida A., Egashira H., Yoshida H., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. Lett. 11 (2001) 2029
11. Maruyama T., Asada M., Shiraishi T., Sakata K., Seki A., Yoshida H., Shinagawa Y., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. Lett. 11 (2001) 2033
12. Maruyama T., Asada M., Shiraishi T., Egashira H., Yoshida H., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 975
13. Maruyama T., Asada M., Ishida A., Yoshida H., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 989
14. Maruyama T., Asada M., Shiraishi T., Yoshida H., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 1743
15. Maruyama T., Kuwabe SI., Kawanaka Y., Shiraishi T., Shinagawa Y., Sakata K., Seki A., Kishida Y., Yoshida H., Maruyama T., Ohuchida S., Nakai H., Hashimoto S., Kawamura M., Kondo K., and Toda M. Bioorg. Med. Chem. 10 (2002) 2103
16. Tsuri T., Honma T., Hiramatsu Y., Okada T., Hashizume H., Mitsumori S., Inagaki M., Arimura A., Yasui K., Asanuma F., Kishino J., and Ohtani M. J. Med. Chem. 40 (1997) 3504
17. Mitsumori S., Tsuri T., Honma T., Hiramatsu Y., Okada T., Hashizume H., Inagaki M., Arimura A., Yasui K., Asanuma F., Kishino J., and Ohtani M. J. Med. Chem. 46 (2003) 2436
18. Torisu K., Kobayashi K., Iwahashi M., Egashira H., Nakai Y., Okada Y., Nanbu F., Ohuchida S., Nakai H., and Toda M. Bioorg. Med. Chem. Lett. 14 (2004) 4557
19. Torisu K., Kobayashi K., Iwahashi M., Nakai Y., Onoda T., Nagase T., Sugimoto I., Okada Y., Matsumoto R., Nanbu F., Ohuchida S., Nakai H., and Toda M. Bioorg. Med. Chem. Lett. 14 (2004) 4891
20. Torisu K., Kobayashi K., Iwahashi M., Nakai Y., Onoda T., Nagase T., Sugimoto I., Okada Y., Matsumoto R., Nanbu F., Ohuchida S., Nakai H., and Toda M. Bioorg. Med. Chem. 12 (2004) 4685
21. Torisu K., Kobayashi K., Iwahashi M., Nakai Y., Onoda T., Nagase T., Sugimoto I., Okada Y., Matsumoto R., Nanbu F., Ohuchida S., Nakai H., and Toda M. Bioorg. Med. Chem. 12 (2004) 5361
22. Torisu K., Kobayashi K., Iwahashi M., Egashira H., Nakai Y., Okada Y., Nanbu F., Ohuchida S., Nakai H., and Toda M. Eur. J. Med. Chem. 40 (2005) 505
23. Sturino C.F., Lachance N., Boyd M., Berthelette C., Labelle M., Li L., Roy B., Scheigetz J., Tsou N., Brideau C., Cauchon E., Carriere M.-C., Denis D., Greig G., Kargman S., Lamontagne S., Mathieu M.-C., Sawyer N., Slipetz D., O'Neill G., Wang Z., Zamboni R., Metters K.M., and Young R.N. Bioorg. Med. Chem. Lett. 16 (2006) 3043
24. Naganawa A., Saito T., Nagao Y., Egashira H., Iwahashi M., Kambe T., Koketsu M., Yamamoto H., Kobayashi M., Maruyama T., Ohuchida S., Nakai H., Kondo K., and Toda M. Bioorg. Med. Chem. 14 (2006) 5562
25. Naganawa, A.; Matsui, T.; Saito, T.; Ima, M.; Tatsumi, T.; Yamamoto, S.; Murota, M.; Yamamoto, H.; Maruyama, T.; Ohuchida, S.; Nakai, H.; Kondo, K.; Toda, M. Bioorg. Med. Chem., in press.
26. Naganawa, A.; Matsui, T.; Ima, M.; Saito, T.; Murota, M.; Aratani, Y.; Kijima, H.; Yamamoto, H.; Maruyama,T.; Ohuchida,S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. in press.
27. Gaude D., Goaller L., and Pierre J.L. Synth. Commun. 16 (1986) 63
28. Fischer A., and Mathivanan N. Tetrahedron Lett. 29 (1988) 1869
29. Kajino M., Shibouta Y., Nishikawa K., and Meguro K. Chem. Pharm. Bull. 39 (1991) 2896
30. Linderberg M., Hellberg S., Björk S., Gotthammar B., Högberg T., Persson K., Schwarcz R., Luthman J., and Johansson R. Eur. J. Med. Chem. 34 (1999) 729
31. 7 introduction of hydrophilic properties into molecules sometimes improves their functional activities.
32. Inhibitory activity against cytochrome P450 was evaluated by the method reported by Crespi et al.:. Crespi C.L., Miller V.P., Penman B.W. Anal. Biochem. 248 (1997) 188
33. Dresser G.K., Spence J.D., and Bailey D.G. Clin. Pharmacokinet. 38 (2000) 41-57