A novel synthesis of the antipsychotic agent ziprasidone

Synthetic Communications

Volumn 26, Issue 8, 1996, Pages 1629-1638

  Urban, Frank J ^a   Breitenbach, Ralph ^a   Gonyaw, Dianne ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NEUROLEPTIC AGENT; ZIPRASIDONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029965192     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003533     Document Type: Article

References (11)

1. Howard, H. R.; Prakash, C.; Seeger, T. F. Drugs of the Future, 1994, 19, 560.
2. Howard, H. R.; Shenk, K. D.; Smolarek, T. A.; Marx, M. H.; Windels, J. H.; Roth, R. W. J. Labelled Compds. Radiopharm., 1994, 34, 117.
3. Quallich, G. J.; Morrissey, P. M. Synthesis, 1993, 51.
4. Abdulla, R. F.; Brinkmeyer, R. S. Tetrahedron, 1979, 35, 1675.
5. Haefliger, W.; Knecht, H. Tet. Lett., 1983, 25, 285.
6. Yevich, J. P.; New, J. S.; Smith, D. W.; Lobeck, W. G.; Catt, J. D.; Minielli, J. L.; Eison, M. S.; Taylor, D. P.; Riblet, L. A.; Temple, D. L. Jr. J. Med. Chem., 1986, 29, 359.
7. Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Tet. Left., 1990, 31, 5595.
8. This unusual product was seen also with other piperazinylethyl substrates in the malonate displacements as well as with the corresponding phenethyl alcohol where hydroxide would be the leaving group.
9. Krapcho, A. P. Synthesis, 1982, 805.
10. Since 12 contained a basic 1-(1,2-benzisotbiazol-3-yl)-piperazine group this would indicate some zwitterionic form at pH 8. This has not been confirmed and the proton nmr in deuteriochloroform showed the α-proton at δ 5.68.
11. Cohen, J. B.; Dakin, H. D., J. Chem. Soc., 1901, 79, 1130.