Catalytic enantioselective synthesis of the dopamine D1 antagonist ecopipam

Tetrahedron Asymmetry

Volumn 23, Issue 2, 2012, Pages 151-156

  Hajra, Saumen ^a   Bar, Sukanta ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARALKYLAMINE; AZIRIDINE; ECOPIPAM; STYRENE;

ARTICLE; AZIRIDINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUZUKI REACTION; THIN LAYER CHROMATOGRAPHY; WITTIG REACTION;

EID: 84858282248     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.01.017     Document Type: Article

References (26)

1. J.W. Kebabian, and D.B. Calne Nature (London U.K.) 277 1979 93 96
2. L.I. Goldberg, P.H. Volkman, J.D. Kohli, and A.N. Kotake Adv. Biochem. Psychopharmacol. 16 1977 251 256
3. J. Hyttel Eur. J. Pharmacol. 91 1983 153 154
4. L.C. Iorio, A. Barnett, F.M. Leitz, V.P. Houser, and C.A. Korduba J. Pharmacol. Exp. Ther. 226 1983 462 468
5. J.G. Berger, W.K. Chang, J.W. Clader, D. Hou, R.E. Chipkin, and A.T. McPhail J. Med. Chem. 32 1989 1913 1921
6. G. Sedvall, L. Farde, S. Stone-Elander, and C. Halldin G.R. Breese, I. Creese, Neurobiology of Central D-1 Dopamine receptors 1991 Plenum Press New York 1
7. A. Labelle, R. de Beaurepaire, L.J. Boulay, D. Naber, B.D. Jones, and T.R. Barnes J. Psychiatr. Neurosci. 23 1998 93 94
8. Coffin, V.; Glue, P. W. WO 9921540-A2, 1999.
9. M.K. Romach, P. Glue, K. Kampman, H.L. Kaplan, G.R. Somer, S. Poole, L. Clarke, V. Coffin, J. Cornish, C.P. O'Brien, and E.M. Sellers Arch. Gen. Psychiatry 56 1999 1101 1106
10. E. Nann-Vernotica, E.C. Donny, G.E. Bigelow, and S.L. Walsh Psychopharmacology (Berlin Ger.) 155 2001 338 347
11. M. Haney, A.S. Ward, R.W. Foltin, and M.W. Fischman Psychopharmacology (Berlin Ger.) 155 2001 330 337
12. P. Karlsson, L. Smith, L. Farde, C. Haernryd, G. Sedvall, and F.A. Wiesel Psychopharmacology (Berlin Ger.) 121 1995 309 316
13. V.L. Coffin, D. McHuch, R.E. Chipkin, and A. Barnett Neurochem. Int. 20 1992 141S 145S
14. R.E. Chipkin, L.C. Iorio, V.L. Coffin, R.D. Mcquade, J.G. Berger, and A. Barnett J. Pharmacol. Exp. Ther. 247 1988 1093 1102
15. A. Astrup, F.L. Greenway, W. Ling, L. Pedicone, J. Lachowicz, C.D. Strader, and R. Kwan Ecopipam Obesity Study Group Obesity 15 2007 1717 1731
16. See the link: http://www.psyadonrx.com/ongoingclinicaltrials.html.
17. See the link: http://clinicaltrials.gov/ct2/show/study/NCT01244633.
18. Berger, J. G.; Chang, W. K.; Gold, E. H.; Clader, J. W. European Patent Application 230270, 1987.
19. G. Wu, Y. Wong, M. Steinman, W. Tormos, D.P. Schumacher, G.M. Love, and B. Shutts Org. Process Res. Dev. 1 1997 359 364
20. R.W. Draper, D. Hou, R. Iyer, G.M. Lee, J.T. Liang, J.L. Mas, W. Tormos, E.J. Vater, F. Günter, I. Mergelsberg, and D. Scherer Org. Process Res. Dev. 2 1998 175 185
21. R.W. Draper, D. Hou, R. Iyer, G.M. Lee, J.T. Liang, J.L. Mas, and E.J. Vater Org. Process Res. Dev. 2 1998 186 193
22. R.J. Perner, C.-H. Lee, M. Jiang, Y.-G. Gu, S. DiDomenico, E.K. Bayburt, K.M. Alexander, K.L. Kohlhaas, M.F. Jarvis, E.L. Kowaluk, and S.S. Bhagwat Bioorg. Med. Chem. Lett. 15 2005 2803 2807
23. S. Hajra, B. Maji, D. Sinha, and S. Bar Tetrahedron Lett. 49 2008 4057 4059
24. S. Hajra, B. Maji, and D. Mal Adv. Synth. Catal. 351 2009 859 864 Corrigendum: Hajra, S.; Maji, B.; Mal, D. Adv. Synth. Catal. 2010, 352, 3112
25. S. Hajra, and D. Sinha J. Org. Chem. 76 2011 7334 7340
26. D.A. Evans, M.M. Fad, and M.T. Bilodeau J. Am. Chem. Soc. 116 1994 2742 2753