First scale-up synthesis of WAY-262398, a novel, dual-acting SSRI/5HT1a antagonist

Organic Process Research and Development

Volumn 13, Issue 1, 2009, Pages 91-97

  Nikitenko, Antonia ^a   Alimardanov, Asaf ^a   Afragola, Jay ^a   Schmid, Jean ^a   Kristofova, Livia ^b   Evrard, Deborah ^c   Hatzenbuhler, Nicole T ^c   Marathias, Vasilios ^c   Stack, Gary ^c   Lenicek, Steve ^c   Potoski, John ^a  

^a WYETH RESEARCH   (United States)

^b Wyeth Research Chemical Development   (Canada)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61449136924     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op8002085     Document Type: Article

References (31)

1. Hatzenbuhler, N. T.; Baudy, R.; Evrard, D. A.; Failli, A.; Harrison, B. L.; Lenichek, S.; Mewshaw, R. E.; Sabb, A.; Shah, U.; Sze, J.; Zhang, M.; Zhou, D.; Chlenov, M.; Kagan, M.; Golembieski, J.; Hornby, G.; Lai, M.; Smith, D. L.; Sullivan, K. M.; Schechter, L. E.; Andree, T. H. J. Med. Chem. 2008, 57, 6980-7004, and references therein.
2. Hatzenbuhler, N. T.; Evrard, D. A.; Harrison, B. L.; Huryn, D.; Inghrim, J.; Kraml, C.; Mattes, J. F.; Mewshaw, R. E.; Zhou, D.; Hornby, G.; Lin, Q.; Smith, D. L.; Sullivan, K. M.; Schechter, L. E.; Beyer, C. E.; Andree, T. H. J. Med. Chem. 2006, 49, 4785-4789, and references therein.
3. Page, M. E.; Cryan, J. F.; Sullivan, A.; Dalvi, A.; Saucy, B.; Manning, D. R.; Lucki, I. J. Pharmacol. Exp. Ther. 2002, 302, 1220-1228.
4. Takeuchi, K.; Kohn, T. J.; Honigschmidt, N. A.; Rocco, V. P.; Spinazze, P. G.; Koch, D. J.; Nelson, D. L.; Wainscott, D. B.; Ahmad, L. J.; Shaw, J.; Threlkeld, P. G.; Wong, D. T. Bioorg. Med. Chem. Lett. 2003, 13, 1903-1905.
5. Atkinson, P. J.; Bromidge, S. M.; Duxon, M. S.; Gaster, L. M.; Hadley, M. S.; Hammond, B.; Johnson, C. N.; Middlemiss, D. N.; North, S. E.; Price, G. W.; Rami, H. K.; Riley, G. J.; Scott, C. M.; Shaw, T. E.; Starr, K. R.; Stemp, G.; Thewlis, K. M.; Thomas, D. R.; Thompson, M.; Vong, A. K. K.; Watson, J. M. Bioorg. Med. Chem. Lett. 2005, 15 (3), 737-741.
6. Nikitenko, A.; Evrard, D. A.; Sabb, A. L.; Vogel, R. L.; Stack, G.; Young, M.; Lin, M.; Harrison, B. L.; Potoski, J. R. Org. Process. Res. Dev. 2008, 12 (1), 76-80.
7. See Supporting Information for details.
8. Hatzenbuhler, N. T.; Evrard, D. A.; Mewshaw, R. E.; Zhou, D.; Shah, U. S.; Inghrim, J. A.; Lenicek, S. E.; Baudy, R. B.; Butera, J. A.; Sabb, A. L.; Failli, A. A.; Ramamoorthy, P. S. PCT Int. Appl. WO 2005/012291, 2005;
9. Chem. Abstr. 2005, 142, 219150.
10. Chan, A. W.-Y.; Curran, T. T.; Iera, S.; Chew, W.; Sellstedt, J. H.; Vid, G.; Feigelson, G.; Ding, Z. PCT Int. Appl. WO 2002/092602, 2002;
11. Chem. Abstr. 2002, 137, 384846.
12. Evrard, D. A.; Zhou, D.; Stack, G. P.; Venkatesan, A. M.; Failli, A. A.; Croce, S. C. U.S. Pat. Appl. Publ. US 2004142926,2004;
13. Chem Abstr. 2004~, 141, 123658.
14. Stack, G. P.; Webb, M. B.; Evrard, D. A.; Zhou, D. U.S. Pat. Appl. Publ. US2004138222, 2004;
15. Chem Abstr. 2004, 141, 123637.
16. Zhou, D.; Stack, G. P. U.S. Pat. Appl. Publ. US2004132714, 2004;
17. Chem. Abstr. 2004, 141, 89093.
18. Webb, M. B.; Stack, G. P.; Asselin, M.; Evrard, D. A. PCT Int. Appl. WO 2004/024733, 2004;
19. Chem. Abstr. 2004, 140, 287397.
20. Feenstra, R. W.; Stoit, A.; Terpstra, J.; Pras-Ravers, M. L.; McCreary, A. C.; Van Vliet, B. J.; Hesselink, M. B.; Kruse, C. G.; Van Scharrenburg, G. J. M. PCT Int. Appl. WO 2006/061376, 2006;
21. Chem. Abstr. 2006, 145, 62874.
22. Feenstra, R. W.; Stoit, A.; Terpstra, J.; Pras-Ravers, M. L.; McCreary, A. C.; Van Vliet, B. J.; Hesselink, M. B.; Kruse, C. G.; Van Scharrenburg, G. J. M. PCT Int. Appl. WO 2006/061377, 2006;
23. Chem Abstr. 2006, 145, 62923.
24. See Table 1, Salt Screening for the Chiral Resolution of Acid 6, Supporting Information.
25. Fox, M. E.; Jackson, M.; Lennon, I. C.; Klosin, J.; Abboud, Kh. A. J. Org. Chem. 2008, 73, 775-784, and references 21-23 therein.
26. (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl] ethyldi-tert-butylphosphine, Solvias SL-J009.
27. 2-Mandyphos, Solvias SL-M004. The sense of stereoinduction reported for a similar substrate using the same metal/ ligand combination provided further evidence in support of the assigned absolute stereochemistry.
28. Briner, P. H.; Fyfe, M. C. T.; Madeley, J. P.; Murray, P. J.; Procter, M. J.; Spindler, F. PCT Int. Appl. WO 2006/016178, 2006;
29. Chem Abstr. 2006, 144, 232918.
30. See Table 2, Conditions for the Chiral Reduction of Ester 14, and Table 3, Conditions for the Chiral Reduction of Acid 23, Supporting Information.
31. For an example of double resolution in a similar class of compounds, see ref 6.