Synthesis and structure-activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 22, 2003, Pages 4729-4742

  Noguchi, Toshiya ^a   Hasegawa, Masahiro ^a   Tomisawa, Kazuyuki ^a   Mitsukuchi, Morihiro ^a  

^a TAISHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(5 PHENYLTHIOPHEN 3 YL)ACETIC ACID; 5 (4 BROMOPHENYL)THIOPHENE 3 CARBOXYLIC ACID; 5 (4 CYCLOHEXYLPHENYL)THIOPHENE 3 CARBOXYLIC ACID; 5 (4 ETHYLPHENYL)THIOPHENE 3 CARBOXYLIC ACID; 5 (4 ISOPROPYLPHENYL)THIOPHENE 3 CARBOXYLIC ACID; 5 (4 METHOXYPHENYL)THIOPHENE 3 CARBOXYLIC ACID; 5 (4 METHYLPHENYL)THIOPHENE 3 CARBOXYLIC ACID; 5 (PHENYLTHIOPHENE) 3 CARBOXYLIC ACID; ANTIRHEUMATIC AGENT; BENZYL 5 (4 BROMOPHENYL)THIOPHENE 3 CARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; ESONARIMOD; ETHYL 5 (4 BROMOPHENYL)THIOPHENE 3 CARBOXYLATE; ETHYL 5 (4 METHYLPHENYL)THIOPHENE 3 CARBOXYLATE; ETHYL 5 PHENYLTHIOPHENE 3 CARBOXYLATE; ISOPROPYL 5 (4 BROMOPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 (4 CHLOROPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 (4 CYCLOHEXYLPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 (4 ETHYLPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 (4 ISOPROPYLPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 (4 METHOXYPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 (4 METHYLPHENYL)THIOPHENE 3 CARBOXYLATE; METHYL 5 PHENYLTHIOPHENE 3 CARBOXYLATE; METHYL[5 (4 BROMOPHENYL)THIOPHEN 3 YL]ACETATE; METHYL[5 (4 CHLOROPHENYL)THIOPHEN 3 YL]ACETATE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [5 (4 BROMOPHENYL)THIOPHEN 3 YL]ACETIC ACID; [5 (4 CHLOROPHENYL)THIOPHEN 3 YL]ACETIC ACID; [5 (4 METHYLPHENYL)THIOPHEN 3 YL]ACETIC ACID;

ADJUVANT ARTHRITIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ANTAGONISM; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0141888582     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.08.009     Document Type: Article

References (25)

1. Takeshita K., Fukazawa I., Futaki N., Kameo K., Tomisawa K., Otomo S., Aihara H. Arzneim.-Forsch./Drug Res. 38:1988;537.
2. Kameo K., Ogawa K., Takeshita K., Nakaike S., Tomisawa K., Sota K. Chem. Pharm. Bull. 36:1988;2050.
3. Takahashi S., Inoue T., Higaki M., Mizushima Y. Drugs Exp. Clin. Res. 24:1998;67.
4. Yasuda Y., Inoue T., Takeshita K. Drugs Exp. Clin. Res. 22:1996;1.
5. Hashimoto M., Kobayashi K., Yamagata N., Katsura T., Sugihara S., Iwabuchi H., Kasama T., Kasahara K., Takahashi T., Takeshita K., Otomo S. Agents Actions. 37:1992;99.
6. Noguchi T., Onodera A., Tomisawa K., Yokomori S. Heterocycles. 57:2002;1907.
7. Clemence F., Le Martret O., Fournex R., Dagnaux G.P.M. Eur. J. Med. Chem. Ther. 9:1974;390.
8. Lautenschläger, H. H.; Parnham, M. J.; Leyck, S.; Winkelmann J.; Brekle, A. Japanese Patent, 202,877, 1985; Chem. Abstr. 1986, 104, 148724.
9. Heller, H. G.; Oliver, S. N.; Whittal, J.; Johncock, W.; Darcy, P. J.; Trundle C. European Patent, 140,540, 1985; Chem. Abstr. 1986, 104, 70288.
10. Ito, K.; Spears, G. W.; Takahashi, F.; Yamada, A.; Tomishima, M.; Miyake, H. World Patent, 125,229, 2001; Chem. Abstr. 2001, 134, 280863.
11. Gallagher, P. T.; Hicks, T. A. European Patent, 259,972, 1988; Chem. Abstr. 1988, 109, 92763.
12. Rooney C.S., Randall W.C., Streeter K.B., Ziegler C., Cragoe E.J. Jr., Schwam H., Michelson S.R., Williams H.W.R., Eichler E., Duggan D.E., Ulm E.H., Noll R.M. J. Med. Chem. 26:1983;700.
13. Fincke H., Bohr H., Staeger S. German Patent, 1,919,381, 1969. Chem. Abstr. 72:1970;31599.
14. Beaton C.M., Chapman N.B., Clarke K. J. Chem. Soc., Perkin Trans. 1. 22:1976;2355.
15. Tomisawa K., Kameo K., Hatada Y., Takahashi Y., Hatayama K. Japanese Patent, 193,990, 1990. Chem. Abstr. 113:1990;231203.
16. Campaigne E., White R.L.J. Jr. Heterocyclic Chem. 25:1988;367.
17. Weston A.W., Michaels R.J. Jr. Org. Synth. 4:1962;915.
18. Tomisawa K., Hasegawa M., Mitsukuchi M., Hatayama K. World Patent, 9,602,529, 1996. Chem. Abstr. 125:1996;33493.
19. Surrey A.R., Hammer H.F., Suter C.M. J. Am. Chem. Soc. 66:1944;1933.
20. Tomisawa K., Hasegawa M., Mitsukuchi M., Hatayama K. Japanese Patent, 194,476, 1997. Chem. Abstr. 127:1997;190640.
21. Moffett R.B. Org. Synthesis. 4:1962;291.
22. Krapcho A.P., Lovey A.J. Tetrahedron Lett. 14:1973;957.
23. Oppenheim J.J., Shneyour A., Kook A.I. J. Immunol. 116:1976;1466.
24. Oppenheim J.J., Kovacs E.J., Matsushima K., Durum S.K. Immunol. Today. 7:1986;45.
25. Mohr W., Wild A. Arzneim.-Forsch./Drug Res. 26:1976;1860.