Enantioseparation of amfepramone (rac-diethylpropion): Preparative separation of the enantiomers and enantioselective analysis

Chirality

Volumn 11, Issue 10, 1999, Pages 772-780

  Boris, Mey ^a   Paulus, Hanns ^a   Lamparter, Erich ^b   Blaschke, Gottfried ^c  

^a Central Institute   (Germany)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

^c UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Chiralcel OD; Chiralpak AD; CZE analysis; Di O 4 toluoyltartaric acid; Di O benzoyltartaric acid; Diastereoisomers; HPLC analysis; Mobile phase composition

Indexed keywords

AMFEPRAMONE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; CRYSTALLIZATION; DRUG DETERMINATION; DRUG STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0345073149     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:10<772::AID-CHIR6>3.0.CO;2-E     Document Type: Article

References (34)

1. Diethylpropion hydrochloride. In: Reynolds JEF, editor. Martindale. The extra pharmacopeia. London: Pharmaceutical Press; 1996. p 1549-1550.
2. Reist M, Christiansen LH, Christoffersen P, Carrupt PA, Testa B. Low configurational stability of amfepramone and cathinone: mechanism and kinetics of chiral inversion. Chirality 1995;7:469-473.
3. Mosher GL. Diethylpropion hydrochloride. In: Connors KA, Amidon GL, Stella VJ, editors. Chemical stability of pharmaceuticals. New York: John Wiley & Sons; 1986. p 421-425.
4. Mey B, Paulus H, Lamparter E, Blaschke G. Kinetics of racemization of (+)- and (-)-diethylpropion: studies in aqueous solution with and without addition of cyclodextrins, in organic solvents and in human plasma. Chirality 1998;10:307-315.
5. The United States Pharmacopeia 23. Rockville, MD: U.S. Pharmacopeial Convention; 1995. p 1774-1777.
6. Grieb SJ, Matlin SA, Belenguer AM, Ritchie HJ. Chiral high-performance liquid chromatography with cellulose carbamate-coated phases. Influence of support surface chemistry on enantioselectivity. J Chromatogr A 1995;697:271-278.
7. Heuermann M, Blaschke G. Chiral separation of basic drugs using cyclodextrins as chiral pseudo-stationary phases in capillary electrophoresis. J Chromatogr 1993;648:267-274.
8. Guttmann A, Paulus A, Cohen AS, Grinberg N, Karger BL. Use of complexing agents for selective separation in high-performance capillary electrophoresis. Chiral resolution via cyclodextrins incorporated within polyacrylamide gel columns. J Chromatogr 1988;448:41-53.
9. The United States Pharmacopeia 23. Rockville, MD: U.S. Pharmacopeial Convention; 1995. p 1982-1984.
10. Jacques J, Fouquey C, Viterbo R. Enantiomeric cyclic binaphthyl phosphoric acids as resolving agents. Tetrahedron Lett 1971;48:4617-4620.
11. Collet A. Optical resolution by crystallization methods. In: Krstulovic AM, editor. Chiral separations by HPLC. Chichester, UK: Ellis Horwood; 1989. p 81-104.
12. Guideline on "Impurities in new drug substances" (EG-Dok. CPMP/ 142/95 Final). In: Feiden K, editor. Arzneimittelprüfrichtlinien. Stuttgart: Wiss. Verlagsges; 1996.
13. Krstulovic AM, Lee CR. Defining drug purity through chromatographic and related methods: current status and perspectives. J Chromatogr B 1997;689:137-153.
14. Ducharme J, Fernandez C, Gimenez F, Farinotti R. Critical issues in chiral drug analysis in biological fluids by high-performance liquid chromatography. J Chromatogr B 1996;686:65-75.
15. Meyer, VR. Accuracy in the chromatographic determination of extreme enantiomeric ratios: a critical reflection. Chirality 1995;7:567-571.
16. Okamoto Y, Kaida Y. Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases. J Chromatogr A 1994;666:403-419.
17. Witte DT, Bruggeman FJ, Franke JP, Copinga S, Jansen JM, De Zeeuw RA. Comparison between cellulose and amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases for enantiomeric separation of 17 amidotetralines. Chirality 1993;5:545-553.
18. Kunath A, Theil F, Jähnisch K. Influence of the kind of the alcoholic modifier on chiral separation on a Chiralpak AD column. J Chromatogr A 1996;728:249-257.
19. Nawrocki J. The silanol group and its role in liquid chromatography. J Chromatogr A 1997;779:29-71.
20. Tang Y. Significance of mobile phase composition in enantioseparation of chiral drugs by HPLC on a cellulose-based chiral stationary phase. Chirality 1996;8:136-142.
21. Ishikawa A, Shibata T. Cellulosic chiral stationary phase under reversed-phase condition. J Liq Chromatogr 1993;16:859-878.
22. Aboulenein HY, Abou-Basha LI, Bakr SA. Direct enantioselective separation of some propranolol analogs by HPLC on normal and reversed cellulose chiral stationary phases. Chirality 1996;8:153-156.
23. Hampe TRE, Schlüter J, Brandt KH, Nagel J, Lamparter E, Blaschke G. Rapid and complete chiral chromatographic separation of racemic quaternary tropane alkaloids. Complementary use of a cellulose-based chiral stationary phase in reversed-phase and normal-phase modes - a mechanistic study. J Chromatogr 1993;634:205-214.
24. Wainer IW, Alembik MC. Resolution of enantiomeric amides on a cellulose tribenzoate chiral stationary phase. Mobile phase modifier effects on retention and stereoselectivity. J Chromatogr 1987;388:65-74.
25. Kirkland KM. Optimization of chiral selectivity on cellulose-based high-performance liquid chromatographic columns using aprotic mobile-phase modifiers. J Chromatogr A 1995;718:9-26.
26. Nicholson LW, Pfeiffer CD, Goralski CT, Singaram B. High-performance liquid chromatographic separation of b-amino alcohols. II. Separation of trans-2-(dialkylamino)cyclohexanols on an amylose-based chiral stationary phase. J Chromatogr A 1996;719:315-320.
27. Okamoto Y, Kawashima M, Hatada K. Chromatographic resolution. XI. Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel. J Chromatogr 1986;363:173-186.
28. Hopf H, Grahn W, Barret DG, Gerdes A, Hilmer J, Hucker J, Okamoto Y, Kaida Y. Optical resolution of [2.2]paracyclophanes by high-performance liquid chromatography on Tris(3,5-dimethylphenylcarbamates) of cellulose and amylose. Chem Ber 1990;123:841-845.
29. Cass QB, Bassi AL, Calafatti SA, Matlin SA, Tiritan ME, Moreira de Campos LM. Carbohydrate carbamate coated onto microporous silica: application to chiral analysis of commercial pharmaceutical drugs. Chirality 1996;8:143-146.
30. Booth TD, Wainer IW. Mechanistic investigation into the enantioselective separation of mexiletine and related compounds, chromatographed on an amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. J Chromatogr A 1996;741:205-211.
31. Cladrowa-Runge S, Hirz R, Kenndler E, Rizzi A. Enantiomeric separation of amphetamine related drugs by capillary zone electrophoresis using native and derivatized β-cyclodextrin as chiral additives. J Chromatogr A 1995;710:339-345.
32. Branch SK, Holzgrabe U, Jefferies TM, Mallwitz H, Oxley FJR. Effect of β-cyclodextrin acetylation on the resolution of phenethylamines with capillary electrophoresis and nuclear magnetic resonance spectroscopy. J Chromatogr A 1997;758:277-292.
33. Gahm KH, Stalcup AM. Sulfated cyclodextrins for the chiral separations of catecholamines and related compounds in the reversed electrophoretic polarity mode. Chirality 1996;8:316-324.
34. Varesio E, Veuthey J-L. Chiral separation of amphetamines by high-performance capillary electrophoresis. J Chromatogr A 1995;717:219-228.