Optimization of the reduction of a 5-benzylidenethiazolidine-2,4-dione derivative supported by the reaction response surface analysis: Synthesis of pioglitazone hydrochloride

Organic Process Research and Development

Volumn 8, Issue 2, 2004, Pages 157-162

  Leś, Andrzej ^a,b   Pucko, Wiesław ^a   Szelejewski, Wiesław ^a  

^a INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE DERIVATIVE; KETONE DERIVATIVE; PIOGLITAZONE; REAGENT;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; PURIFICATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SURFACE PROPERTY; TEMPERATURE DEPENDENCE;

EID: 1842454309     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0300286     Document Type: Article

References (27)

1. Tanis, S. P.; Parker, T. T.; Cocla, J. R.; Fisher, R. M.; Kletzein, R. F. J. Med. Chem. 1996, 39, 5053.
2. Sohda, T.; Momose, Y.; Meguro, K.; Sugiyama, Y.; Ikeda, H. Arzeim.-Forsch. 1990, 40, 37.
3. Sohda, T.; Ikeda, H.; Megura, K. Chem. Pharm. Bull. 1995, 43, 2168.
4. Gillies, P. S.; Dunn, Ch. J. Drugs 2000, 60, 333.
5. Yoshioka, T.; Fujita, T.; Kanai, T.; Aizawa, Y.; Kutumada, T.; Hasegawa, K.; Horikoshi, H. J. Med. Chem. 1989, 32, 421.
6. Hulin, B.; Clark, D. A.; Goldstein, S. W.; McDermott, R. E.; Dambek, P. J.; Kappeler, W. H.; Lamphere, C. H.; Lewis, D. M.; Rizzi, J. P. J. Med. Chem. 1992, 35, 1853.
7. Cantello, B. C. C.; Cawthorne, M. A.; Cottam, G. P.; Duff, P. T.; Haigh, D.; Hindley, R. M.; Lister, C. A.; Smith, S. A.; Thurlby, P. L. J. Med. Chem. 1994, 37, 3977.
8. Young, P. W.; Buckle, D. R.; Cantello, B. C. C.; Chapman, H.; Clapham, J. C.; Coyle, P. J.; Haigh, D.; Hindley, R. M.; Holder, J. C.; Kallender, H.; Latter, A. J.; Lawrie, K. W. M.; Mossakowska, D.; Murphy, G. J.; Roxbee Cox, L. ; Smith, S. A. J. Pharmacol. Exp. Ther. 1998, 284, 751.
9. Cantello, B C. C.; Eggleston, D. S.; Haigh, D.; Haltiwanger, R. C.; Heath, C. M.; Hindley, R. M.; Jennings, K. R.; Sime, J. T.; Woroniecki, S. R. J. Chem. Soc., Perkin Trans. 1 1994, 3319.
10. Huber, J. E. U.S. Patent 811,103, 1991; Chem. Abstr. 1993, 119, 249944.
11. Ohnota, M.; Orita, K.; Aizawa, Y.; Yoskida, N.; Sakamaki, T. Japan Patent 178,135, 2000; Chem. Abstr. 2001, 136, 37597.
12. Gilies, R. G.; Lewis, N. J.; Quick, J. K.; Sasse, M. J.; Urquhart, M. W. J.; Youssef, L. Tetrahedron 2000, 56, 4531.
13. Gilies, R. G.; Lewis, N. J.; Moore, S.; Pool, C. R.; Quick, J. K.; Urquhart, M. GB Patent 3310, 1997; Chem. Abstr. 1998, 129, 202936.
14. Meguro, K.; Fujita, T. Hatanaka, C.; Oi, S. Japan Patent 174,278, 1986; Chem. Abstr. 1988, 109, 6504.
15. Saito, Y.; Mizufune, H.; Yamashita, M. Japan Patent 167,862, 1996; Chem. Abstr. 1998, 128, 127942.
16. Qu, J.; Ichikawa, S.; Iwane, H. Japan Patent 146,437; Chem. Abstr. 1999, 134, 29413.
17. Ueno, H.; Oe, T.; Suehiro, I.; Sekiya, A. Japan Patent 302,720, 1996; Chem. Abstr. 1998, 129, 54363.
18. Morita, H.; Mori, H. Japan Patent 103,220, 1995; Chem. Abstr. 1997, 126, 47216.
19. Mori, H.; Morita, H.; Furubuyashi, Y. Japan Patent 279,874, 1996; Chem. Abstr. 1998, 128, 294780.
20. Hikage, N.; Fujimoto, K.; Takebayashi, T. Japan Patent 213,107, 1997; Chem. Abstr. 1999, 130, 209702.
21. Wolff; H. P.; Witte, E. C.; Kuehnle, H. F. German Patent 19,711,616, 1997; Chem. Abstr. 1998, 129, 260452.
22. Clark, D. A. U.S. Patent 127,831, 1987; Chem. Abstr. 1989, 111, 23503.
23. Heath, C. M.; Imrie, R. C.; Rees, M. J.; Robins, K. G.; Verrall, M. S. Journal of Chemical Technology & Biotechnology 1997, 68, 324.
24. Szelejewski, W.; Fra̧czek, K.; Kotowski, W.; Kołt, J.; Burczyk, R. Przemysł Chemiczny 1974, 53, 605 (Pol.); Chem. Abstr. 1975, 82, 31091c.
25. Szelejewski, W.; Fra̧czek, K.; Kotowski, W.; Kołt, J.; Burczyk, R. Przemysł Chemiczny 1974, 53, 605 (Pol.); Chem. Abstr. 1975, 82, 31091c.
26. Modde 6.0; Umetrics AB: Umea, Sweden (www.umetrics.com).
27. SAS Institute Inc.: Cary, NC, U.S.A. (www.sas.com).