The application of preparative batch HPLC, supercritical fluid chromatography, steady-state recycling, and simulated moving bed for the resolution of a racemic pharmaceutical intermediate

Chirality

Volumn 20, Issue 2, 2008, Pages 139-146

  Yan, Tony Q ^a   Orihuela, Carlos ^a   Swanson, David ^b  

^a AMGEN INC   (United States)

^b Johnson Matthey Pharmaceutical Materials Inc   (United States)

Author keywords

Chiral separation; Pharmaceutical intermediate; Preparative chromatography

Indexed keywords

CYCLOALKANE DERIVATIVE;

ARTICLE; DRUG DETERMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PRODUCTIVITY; RACEMIC MIXTURE; SIMULATED MOVING BED; SIMULATION; STEADY STATE; STEADY STATE RECYCLING; SUPERCRITICAL FLUID CHROMATOGRAPHY;

AMINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, SUPERCRITICAL FLUID; PHARMACEUTICAL PREPARATIONS; SOLVENTS; STEREOISOMERISM;

EID: 38549154616     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20512     Document Type: Article

References (21)

1. Miller L, Grill CM, Yan TQ, Dapremont O, Huthmann E, Juza M. Batch and simulated moving bed chromatographic resolution of a pharmaceutical racemate. J Chromatogr A 2003;1006:267.
2. Terfloth GJ. Enantioseparations in super- and subcritical fluid chromatography. J. Chromatogr A 2001;906:301.
3. Zhao Y, Pritts WA. Chiral separation of selected proline derivatives using a polysaccharide type stationary phase by high-performance liquid chromatography. J Chromatogr A 2007;1156:228.
4. Yan TQ, Orihuela C. Rapid and high throughput separation technologies - Steady state recycling and supercritical fluid chromatography for chiral resolution of pharmaceutical intermediates. J Chromatogr A 2007;1156:220.
5. Schramm H, Kaspereit M, Kienle A, Seidel-Mogenstern A. Improved operation of simulated moving bed processes through cyclic modulation of feed flow and feed concentration. Chem Eng Sci 2003;58:5217.
6. Francotte E, Leutert T, La Vecchia L, Ossola F, Richert P, Schmidt A. Preparative resolution of the enantiomers of tert-leucine derivatives by simulated moving bed chromatography. Chirality 2002;14:313.
7. Zhang Z, Mazzotti M, Morbidelli M. Power feed operation of simulated moving bed units: changing flow-rates during the switching interval. J Chromatogr A 2003;1006:87.
8. Strube J, Jupke A, Epping A, Schmidt-Traub H, Sculte M, Devant R. Design, optimization, and operation of SMB chromatography in the production of enantiomerically pure pharmaceuticals. Chirality 1999;11:440.
9. Grill CM. Closed-loop recycling with periodic intra-profile injection: a new binary preparative chromatographic technique. J Chromatogr A 1998;796:101.
10. Grill CM, Miller L. Separation of a racemic pharmaceutical intermediate using closed-loop steady state recycling. J Chromatogr A 1998;827:359.
11. Kennedy JH, Bevo MD, Sharp VS, Williams JD. Comparison of separation efficiency of early phase active pharmaceutical intermediates by steady state recycle and batch chromatographic techniques. J Chromatogr A 2004;1026:101.
12. Grill CM, Miller L, Yan TQ. Resolution of a racemic pharmaceutical intermediate: a comparison of preparative HPLC, steady state recycling, and simulated moving bed. J Chromatogr A 2004;1046:55.
13. Villeneuve MS, Anderegg RJ. Analytical supercritical fluid chromatography using fully automated column and modifier selection valves for the rapid development of chiral separations. J Chromatogr A 1998;826:217.
14. Karanam BV, Welch CJ, Reddy VG, Chllenski J, Biba M, Vincert S. Species differential stereoselective oxidation of a methylsulfide metabolite of Mk-0767, a peroxisome proliferator-activated receptor dual agonist. Drug Metab Dispos 2004;22:1061.
15. Liu Y, Berthod A, Mitchell CR, Xiao TL, Zhang B, Armstrong DW. Super/subcritical fluid chromatography chiral separations with macrocyclic glycopeptide stationary phases. J Chromatogr A 2002;978:185.
16. Jusforgues P. Instrument design and separation in large scale industrial supercritical fluid chromatography. J High Res Chromatogr 1995;4:153.
17. Blehaut J, Nicoud RM. Recent aspects in simulated moving bed. Analusis 1998;26:M60.
18. Johannsen M, Peper S, Depta A. Simulated moving bed chromatography with supercritical fluids for the resolution of bi-naphthol enantiomers and phytol isomers. J Biochem Biophys Methods 2002;54:85.
19. Zhang Y, McConnell O. Simulated moving columns technique for chiral liquid chromatography. J Chromatogr A 2004;1028:227.
20. Zhang Y, Dai J, Wang-Iverson DB, Tymiak AA. Simulated moving columns technique for enantioselective supercritical fluid chromatography. Chirality 2007;9:683.
21. Welch CJ, Biba M, Gouker JR, Kath G, Augustine P, Hosek P. Solving multicomponent chiral separation challenges using a new SFC tandem column screening tool. Chirality 2007;3:184.