Synthesis and activities of oxidative metabolites of the anti-arthritic drug candidate S-2474

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 11, 2003, Pages 2415-2419

  Inagaki, Masanao ^a   Jyoyama, Hirokuni ^a   Ono, Takashi ^a   Yamada, Katsutoshi ^a   Kobayashi, Mika ^a   Baba, Takahiko ^a   Touchi, Akira ^a   Iwatani, Kouji ^a   Ohkawa, Tomoyuki ^a   Matsumoto, Saichi ^a   Tsuri, Tatsuo ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYL 5 (3,5 DI TERT BUTYL 4 HYDROXYBENZYLIDENE) 1,2 ISOTHIAZOLIDINE 1,1 DIOXIDE; 5 (3,5 DI TERT BUTYL 4 HYDROXYBENZYLIDENE) 1,2 ISOTHIAZOLIDINE 1,1 DIOXIDE; 5 (7 TERT BUTYL 3,3 DIMETHYL 2,3 DIHYDROBENZOFURAN 5 YLMETHYLENE) 2 ETHYL 1,2 ISOTHIAZOLIDINE 1,1 DIOXIDE; ANTIRHEUMATIC AGENT; DIHYDROBENZOFURAN DERIVATIVE; DRUG METABOLITE; INTERLEUKIN 1; PROSTAGLANDIN E2; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG ACTIVITY; DRUG METABOLISM; DRUG OXIDATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PROSTAGLANDIN SYNTHESIS;

EID: 12444251018     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00141-X     Document Type: Article

References (13)

1. Inagaki M., Tsuri T., Jyoyama H., Ono T., Yamada K., Kobayashi M., Hori Y., Arimura A., Yasui K., Ohno K., Kakudo S., Koizumi K., Suzuki R., Kato M., Kawai S., Matsumoto S. J. Med. Chem. 43:2000;2040.
2. Miller J.A., Matthews R.S. J. Org. Chem. 57:1992;2514. and references cited therein.
3. Ikuta, H.; Yamagishi, Y.; Akasaka, M.; Yamatsu, I.; Kobayashi, S.; Yoda, H.: Katayama, K. JP Patent 115,860, 1988.
4. Inagaki M., Matsumoto S., Tsuri T. J. Org. Chem. 68:2003;1128.
5. Nahm S., Weinreb S.M. Tetrahedron Lett. 22:1982;3815.
6. 1 a methine proton of the benzhydryl protecting group was deprotonated at -78°C and the reaction did not proceed cleanly.
7. Poss M.A., Reid J.A. Tetrahedron Lett. 33:1992;7291.
8. (a) Gut V., Rudinger J., Walter R., Herling P.A., Schwartz I.L. Tetrahedron. 24:1968;6351.
9. (b) Brkic Z., Herak J.J., Mandic Z., Lukic I., Tomic M., Kovacevic M. Tetrahedron. 49:1993;9801.
10. Swingle, K. F.; Bell, R. L.; Moore, G. G. Antiinflammatory Activity of Antioxidants. Antiinflammatory and Anti-Rheumatic Drugs; Rainsford, K. D. Ed.; CRC: Boca Raton, FL, 1985; Vol. III, p. 105.
11. (a) Janusz J.M., Young P.A., Ridgeway J.M., Scherz M.W., Enzweiler K., Wu L.I., Gan L., Darolia R., Matthews R.S., Hennes D., Kellstein D.E., Green S.A., Tulich J.L., Rosario-Jansen T., Magrisso I.J., Wehmeyer K.R., Kuhlenbeck D.L., Eichhold T.H., Dobson R.L.M., Sirko S.P., Farmer R.W. J. Med. Chem. 41:1998;1112.
12. (b) Janusz J.M., Young P.A., Ridgeway J.M., Scherz M.W., Enzweiler K., Wu L.I., Gan L., Pikul S., McDow-Dunham K.L., Johnson C.R., Senanayake C.B., Kellstein D.E., Green S.A., Tulich J.L., Rosario-Jansen T., Magrisso I.J., Wehmeyer K.R., Kuhlenbeck D.L., Eichhold T.H., Dobson R.L.M. J. Med. Chem. 41:1998;1124.
13. (c) Janusz J.M., Young P.A., Ridgeway J.M., Scherz M.W., Enzweiler K., Wu L.I., Gan L., Chen J., Kellstein D.E., Green S.A., Tulich J.L., Rosario-Jansen T., Magrisso I.J., Wehmeyer K.R., Kuhlenbeck D.L., Eichhold T.H., Dobson R.L.M. J. Med. Chem. 41:1998;3515.