Preparative chiral chromatography and chiroptical characterization of enantiomers of omeprazole and related benzimidazoles

Chirality

Volumn 19, Issue 9, 2007, Pages 706-715

  Andersson, Shalini ^a   Nelander, Hanna ^a   Öhlén, Kristina ^a  

^a ASTRAZENECA R AND D   (Sweden)

Author keywords

Absolute configuration; Circular dichroism; Enantiomer separation; Lansoprazole; On line polarimetric detection; Pantoprazole; Preparative chromatography; Rabeprazole; Supercritical fluid chromatography

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; LANSOPRAZOLE; OMEPRAZOLE; PANTOPRAZOLE; RABEPRAZOLE;

ARTICLE; CHIRAL CHROMATOGRAPHY; CIRCULAR DICHROISM; DRUG SCREENING; DRUG STRUCTURE; ENANTIOMER; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SUPERCRITICAL FLUID CHROMATOGRAPHY;

2-PYRIDINYLMETHYLSULFINYLBENZIMIDAZOLES; BENZIMIDAZOLES; CHROMATOGRAPHY; CHROMATOGRAPHY, SUPERCRITICAL FLUID; CIRCULAR DICHROISM; ENZYME INHIBITORS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OMEPRAZOLE; STEREOISOMERISM;

EID: 34748897421     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20375     Document Type: Article

References (23)

1. Lindberg P, Brändström A, Wallmark B, Mattsson H, Rikner L, Hoffman KJ. Omeprazole: the first proton pump inhibitor. Med Res Rev 1990;10:1-54.
2. Olbe L, Carlsson E, Lindberg P. A proton-pump inhibitor expedition: the case histories of omeprazole and esomeprazole. Nat Rev Drug Discov 2003;2:132-139.
3. Lindberg P, Keeling D, Fryklund J, Andersson T, Lundborg P, Carlsson E. Esomeprazole-enhanced bio-availability, specificity for the proton pump and inhibition of acid secretion. Aliment Pharmacol Ther 2003;17:481-488.
4. Eliel EL, Wilen SH. Stereochemistry of organic compounds. New York: Wiley; 1994. p 1267.
5. Francotte ER. Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers. J Chromatogr A 2001;906:379-397.
6. Andersson S, Allenmark SG. Preparative chiral chromatographic resolution of enantiomers in drug discovery. J Biochem Biophys Methods 2002;54:11-23.
7. Cox GB. Preparative enantioselective chromatography. Oxford: Blackwell Publishing; 2005.
8. Allenmark S, Bomgren B, Borén H, Lagerström P-O. Direct optical resolution of a series of pharmacologically active racemic sulfoxides by high-performance liquid affinity chromatography. Anal Biochem 1984;136:293-297.
9. Erlandsson P, Isaksson R, Lorentzon P, Lindberg P. Resolution of the enantiomers of omeprazole and some of its analogs by liquid chromatography on a trisphenylcarbamoylcellulose-based stationary phase. The effect of the enantiomers of omeprazole on gastric glands. J Chromatogr 1990;532:305-319.
10. Balmér K, Persson BA, Lagerström PO. Stereoselective effects in the separation of enantiomers of omeprazole and other substituted benzimidazoles on different chiral phases. J Chromatogr A 1994;660:269-273.
11. Tanaka M, Yamazaki H, Hakusui H. Direct HPLC separation of enantiomers of pantoprazole and other benzimidazole sulfoxides using cellulose-based chiral stationary phases in reversed-phase mode. Chirality 1995;7:612-615.
12. Katsuki H, Yagi H, Arimori K, Nakamura C, Nakano M, Katafuchi S, Fujioka Y, Fujiyama S. Determination of R(+)- and S(-)-lansoprazole using chiral stationary phase liquid chromatography and their enantioselective pharmacokinetics in humans. Pharm Res 1996;13:611-615.
13. Stenhoff H, Blomqvist Å, Lagerström PO. Determination of the enantiomers of omeprazole in blood plasma by normal phase liquid chromatography and detection by atmospheric pressure ionization tandem mass spectrometry. J Chromatogr B 1999;734:191-201.
14. Nelander H, Öhlén K, Andersson S. Preparative separation and characterisation of the enantiomers of omeprazole and structural analogues. In: The 12th International Symposium on Chirality, ISCD 12 - Chirality 2000, Chamonix, France, September 24-28, 2000.
15. Montanari CA, Cass QB, Tiritan ME, de Souza AL. A QSERR study on enantioselective separation of enantiomeric sulphoxides. Anal Chim Acta 2000;419:93-100.
16. Toribio L, del Nozal MJ, Bernal JL, Alonso C, Jimenez JJ. Comparative study of the enantioselective separation of several antiulcer drugs by high-performance liquid chromatography and supercritical fluid chromatography. J Chromatogr A 2005;1091:118-123.
17. von Unge S, Lager V, Sjölin L. Stereochemical assignment of the enantiomers of omeprazole from X-ray analysis of a fenchyloxymethyl derivative of (+)-R-omeprazole. Tetrahedron: Asymmetry 1997;8:1967-1970.
18. Nochi S, Kawai T, Kawakami Y, Asakawa N, Ueda N, Hayashi K, Souda S. Preparation and absolute configuration of the optical isomers of sodium 2-[[4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1H-benzimidazole (E3810). Chem Pharm Bull 1996;44:1853-1857.
19. Brändström A, Lindberg P, Bergman NK, Alminger T, Junggren UC. Chemical reactions of omeprazole and omeprazole analogues. I. A survey of the chemical transformation of omeprazole and its analogues. Acta Chem Scand 1989;43:536-548.
20. Gasteiger J, Rudolph C, Sadowski J. Automatic generation of 3D atomic coordinates for organic molecules. Tetrahedron Comput Methods 1990;3:537-547.
21. Omega: OpenEye Scientific Software. Santa Fe, NM, USA, 2006.
22. Stewart JJP. Semiempirical molecular orbital methods. In: Lipkowitz KB, Boyd DB, editors. Reviews in computational chemistry. New York: VCH; 1990. p 45-81.
23. Rodger A, Nordén B. Circular dichroism and linear dichroism. Oxford: Oxford University Press; 1997.