Chiral separation of potent corticotropin-releasing factor-1 receptor antagonists by supercritical fluid chromatography

Journal of Pharmaceutical and Biomedical Analysis

Volumn 54, Issue 3, 2011, Pages 602-606

  Qian Cutrone, Jingfang ^a   Hartz, Richard ^a   Ahuja, Vijay T ^a   Vrudhula, Vivekananda M ^a   Wu, Dauh Rurng ^a   Dalterio, Richard A ^a   Wang Iverson, David ^a   Bronson, Joanne J ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

CRF1 antagonist; Drug discovery; Enantiomeric separation; Pyrazinone; Supercritical fluid chromatography

Indexed keywords

ALCOHOL; ALKYL GROUP; AROMATIC COMPOUND; CORTICOTROPIN RELEASING FACTOR RECEPTOR 1; PYRAZINE DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; SUPERCRITICAL FLUID CHROMATOGRAPHY;

AMYLOSE; CHROMATOGRAPHY, SUPERCRITICAL FLUID; CORTICOTROPIN-RELEASING HORMONE; HUMANS; PHENYLCARBAMATES; PYRAZINES; RECEPTORS, CORTICOTROPIN-RELEASING HORMONE; STEREOISOMERISM;

EID: 78149500828     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.09.031     Document Type: Article

References (14)

1. De Souza E.B., Grigoriadis D.E. Corticotropin-releasing factor: physiology, pharmacology, and role in central nervous system and immune disorders. Psychopharmacology: The Fourth Generation of Progress 1995, 505-517. Raven, New York. F.E. Bloom, D.J. Kupfer (Eds.).
2. Owens M.J., Nemeroff C.B. Physiology and pharmacology of corticotrophin-releasing factor. Pharmacol. Rev. 1991, 43:425-473.
3. Holsboer F. The rationale for corticotropin-releasing hormone receptor (CRH-R) antagonists to treat depression and anxiety. J. Psychiatr. Res. 1999, 33:181-214.
4. Dzierba C.D., Hartz R.A., Bronson J.J. Recent advances in corticotropin-releasing factor receptor antagonists. Anuual Reports in Medcinal Chemistry 2008, vol. 43:1-23. Academic, San Diego.
5. A.G. Arvanitis, R.E. Olson, C.R. Arnold III, W.E. Frietze, Pyrazinones and triazinones and their derivatives thereof. World Patent Appl. WO 98/11075 A1 (1998).
6. 3-phenylpyrazinones as novel corticotropin-releasing factor-1 (CRF1) receptor antagonists. J. Med. Chem. 2009, 52:4173-4191.
7. Hartz R.A., Ahuja V.T., Mattson R.J., Denhart D.J., Deskus J.A., Ditta J.L., Vrudhula V., Pan S., Zhuo X., Shu Y., Grace J.E., Lentz K.A., Lelas S., Li Y., Molski T.F., Krishnananthan S., Wong H., Qian-Cutrone J., Schartman R., Denton R., Lodge N.J., Zaczek R., Macor J.E., Bronson J.J. A strategy to minimize reactive metabolite formation: discovery of (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-[6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino]-5-oxo-4,5-dihydropyrazine-2-carbonitrile, a potent, orally bioavailable corticotropin-releasing factor-1 (CRF) receptor antagonist. J. Med. Chem. 2009, 52:7653-7668.
8. 1 receptor antagonist. J. Med. Chem. 2009, 52:4161-4172.
9. Berger T.A. Packed Column SFC 1995, The Royal Society of Chemistry, Cambridge, UK.
10. Supercritical Fluid Chromatography with Packed Columns: Techniques and Application 1998, Marcel Dekker, Inc., New York. K. Anton, C. Berger (Eds.).
11. Taylor L.T. Supercritical fluid chromatograph. Anal. Chem. 2008, 80:4285-4294.
12. Miller L., Potter M. Preparative chromatographic resolution of racemates using HPLC and SFC in a pharmaceutical environment. J. Chromatogr. B 2008, 875:230-236.
13. Wu D., Leith L., Balasubramanian B., Palcic T., Wang-Iverson D. The impact of chiral supercritical fluid chromatography in drug discovery: from analytical to multigram scale. Am. Lab. 2006, 38:24-26.
14. Qian-Cutrone J., Dasgupta B., Kozlowski E., Dalterio R., Wang-Iverson D., Vrudhula V. Separation of maxi-K channel opening 3-substitued-4-arylquinolinone atropisomers by enantioselective supercritical fluid chromatography. J. Pharm. Biomed. Anal. 2008, 48:1120-1126.