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Volumn 19, Issue 8, 2007, Pages 647-653

Direct high-performance liquid chromatographic separation of the enantiomers of an aromatic amine and four aminoalcohols using polysaccharide chiral stationary phases and acidic additive

Author keywords

aminoalcohols; Enantiomers separation; Mobile phase composition; Pharmaceuticals; Polysaccharide chiral stationary phases

Indexed keywords

2 (DIPHENYLHYDROXYMETHYL)PYRROLIDINE; 2 PROPANOL; 3,5 DIMETHYLPHENYLCARBAMATE; ACID; AMINOALCOHOL; AMYLOSE; AROMATIC AMINE; BENZYLAMINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; HEXANE; ISOPRENALINE; N BENZYL ALPHA METHYLBENZYLAMINE; PHENYLALANINOL; POLYSACCHARIDE; PYRROLIDINE DERIVATIVE; TRYPTOPHANOL; UNCLASSIFIED DRUG;

EID: 34447569372     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20438     Document Type: Conference Paper
Times cited : (17)

References (27)
  • 1
    • 0035847272 scopus 로고    scopus 로고
    • Separation of enantiomers: Needs, challenges, perspectives
    • Maier NM, Franco P, Lindner W. Separation of enantiomers: needs, challenges, perspectives. J Chromatogr A 2001;906:3-33.
    • (2001) J Chromatogr A , vol.906 , pp. 3-33
    • Maier, N.M.1    Franco, P.2    Lindner, W.3
  • 2
    • 0026713228 scopus 로고
    • The relevance of chirality to the study of biological activity
    • Crossley R. The relevance of chirality to the study of biological activity. Tetrahedron 1992;48:8155-8178.
    • (1992) Tetrahedron , vol.48 , pp. 8155-8178
    • Crossley, R.1
  • 3
    • 0035847205 scopus 로고    scopus 로고
    • Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers
    • Francotte ER. Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers. J Chromatogr A 2001;906:379-397.
    • (2001) J Chromatogr A , vol.906 , pp. 379-397
    • Francotte, E.R.1
  • 4
    • 0030022677 scopus 로고    scopus 로고
    • Importance of stereospecific bioanalytical monitoring in drug development
    • Caldwell J. Importance of stereospecific bioanalytical monitoring in drug development. J Chromatogr A 1996;719:3-13.
    • (1996) J Chromatogr A , vol.719 , pp. 3-13
    • Caldwell, J.1
  • 5
    • 84889479105 scopus 로고    scopus 로고
    • Preparative chiral chromatography. A powerful and efficient tool in drug discovery
    • Subramanian G, editor, 3rd ed. Weinheim: Wiley-VCH;
    • Andersson S. Preparative chiral chromatography. A powerful and efficient tool in drug discovery. In: Subramanian G, editor. Chiral separation techniques, 3rd ed. Weinheim: Wiley-VCH; 2007. p 585-599.
    • (2007) Chiral separation techniques , pp. 585-599
    • Andersson, S.1
  • 6
    • 0034731684 scopus 로고    scopus 로고
    • Q6A Specifications: Test procedure and acceptance criteria for new drug substances and new drug products: chemical substances
    • Food and Drug Administration
    • Food and Drug Administration. Q6A Specifications: test procedure and acceptance criteria for new drug substances and new drug products: chemical substances. Federal Register 2000;65:83041-83063.
    • (2000) Federal Register , vol.65 , pp. 83041-83063
  • 7
    • 34447525824 scopus 로고    scopus 로고
    • European Agency for the Evaluation of Medicinal Products. Note for guidance on the investigation of bioavailability and bioequivalence. London. 2001.
    • European Agency for the Evaluation of Medicinal Products. Note for guidance on the investigation of bioavailability and bioequivalence. London. 2001.
  • 8
    • 0032482102 scopus 로고    scopus 로고
    • Polysaccharide derivatives for chromatographic separation of enantiomers
    • Okamoto Y, Yashima E. Polysaccharide derivatives for chromatographic separation of enantiomers. Angew Chem Int Ed 1998;37:1020-1043.
    • (1998) Angew Chem Int Ed , vol.37 , pp. 1020-1043
    • Okamoto, Y.1    Yashima, E.2
  • 9
    • 84889442369 scopus 로고    scopus 로고
    • Role of polysaccharides in chiral separations by liquid chromatography and capillary electrophoresis
    • Subramanian G, editor, 3rd ed. Weinheim: Wiley-VCH;
    • Ali I, Aboul-Enein HY. Role of polysaccharides in chiral separations by liquid chromatography and capillary electrophoresis. In Subramanian G, editor. Chiral separation techniques, 3rd ed. Weinheim: Wiley-VCH; 2007. p 29-97.
    • (2007) Chiral separation techniques , pp. 29-97
    • Ali, I.1    Aboul-Enein, H.Y.2
  • 10
    • 0032555628 scopus 로고    scopus 로고
    • Resolution of the enantiomers of tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via an imine-enamine tautomerism
    • Caccamese S, Principato G. Resolution of the enantiomers of tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via an imine-enamine tautomerism. Tetrahedron Asymm 1998;9:2939-2945.
    • (1998) Tetrahedron Asymm , vol.9 , pp. 2939-2945
    • Caccamese, S.1    Principato, G.2
  • 11
    • 0029051463 scopus 로고
    • Direct high-performance liquid chromatographic separation of the enantiomers of methoxy and hydroxy derivatives of 3, 4-dihydro-3-(dipropylamino)-2H-1- benzopyrans with dopaminergic activity
    • Caccamese S, Principato G, Viaud MC, Guillaumet G. Direct high-performance liquid chromatographic separation of the enantiomers of methoxy and hydroxy derivatives of 3, 4-dihydro-3-(dipropylamino)-2H-1- benzopyrans with dopaminergic activity. J Chromatogr A 1995;704:83-87.
    • (1995) J Chromatogr A , vol.704 , pp. 83-87
    • Caccamese, S.1    Principato, G.2    Viaud, M.C.3    Guillaumet, G.4
  • 12
    • 28444467340 scopus 로고    scopus 로고
    • Enhanced chromatographic resolution of amine enantiomers as carbobenzyloxy derivatives in high-performance liquid chromatography and supercritical fluid chromatography
    • Kraml CM, Zhou D, Byrne N, McConnell O. Enhanced chromatographic resolution of amine enantiomers as carbobenzyloxy derivatives in high-performance liquid chromatography and supercritical fluid chromatography. J Chromatogr A 2005;1100:108-115.
    • (2005) J Chromatogr A , vol.1100 , pp. 108-115
    • Kraml, C.M.1    Zhou, D.2    Byrne, N.3    McConnell, O.4
  • 13
    • 0033556622 scopus 로고    scopus 로고
    • Enantiomeric impurities in chiral catalysts, auxiliaries, syntons and resolving agents. Part 2
    • Armstrong DW, He L, Yu T, Lee JT, Liu Y. Enantiomeric impurities in chiral catalysts, auxiliaries, syntons and resolving agents. Part 2. Tetrahedron Asymm 1999;10:37-60.
    • (1999) Tetrahedron Asymm , vol.10 , pp. 37-60
    • Armstrong, D.W.1    He, L.2    Yu, T.3    Lee, J.T.4    Liu, Y.5
  • 14
    • 2942565915 scopus 로고    scopus 로고
    • Effect of amine mobile phase additives on chiral subcritical fluid chromatography using polysaccharide stationary phases
    • Ye YK, Lynam G, Stringham RW. Effect of amine mobile phase additives on chiral subcritical fluid chromatography using polysaccharide stationary phases. J Chromatogr A 2004;1041:211-217.
    • (2004) J Chromatogr A , vol.1041 , pp. 211-217
    • Ye, Y.K.1    Lynam, G.2    Stringham, R.W.3
  • 15
    • 13444280266 scopus 로고    scopus 로고
    • Hyun MH, Cho YJ. Preparation and application of a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid without extra free aminopropyl groups on silica surface. J Sep Sci 2005;28:31-38.
    • Hyun MH, Cho YJ. Preparation and application of a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid without extra free aminopropyl groups on silica surface. J Sep Sci 2005;28:31-38.
  • 16
    • 22244448384 scopus 로고    scopus 로고
    • Biogenetically inspired enantioselective approach to indolo[2, 3-a]-and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin
    • Bassas O, Llor N, Santos MM, Griera M, Molins E, Amat M, Bosch J. Biogenetically inspired enantioselective approach to indolo[2, 3-a]-and benzo[a]quinolizidine alkaloids from a synthetic equivalent of secologanin. Org Lett 2005;7:2817-2820.
    • (2005) Org Lett , vol.7 , pp. 2817-2820
    • Bassas, O.1    Llor, N.2    Santos, M.M.3    Griera, M.4    Molins, E.5    Amat, M.6    Bosch, J.7
  • 17
    • 34447499313 scopus 로고    scopus 로고
    • Pyrrolidine derivatives, and preparation thereof, for treating diseases with abnormal dopaminergic neurotrasmission and treating cocain addition and overdose. PCT Int
    • Pat Appl; WO 97,240,030
    • Jackson PF. Pyrrolidine derivatives, and preparation thereof, for treating diseases with abnormal dopaminergic neurotrasmission and treating cocain addition and overdose. PCT Int Pat Appl; WO 97,240,030 (1997).
    • (1997)
    • Jackson, P.F.1
  • 18
    • 0025787814 scopus 로고
    • Chirality in α- and β- adrenoceptor agonist and antagonist
    • Ruffolo RR. Chirality in α- and β- adrenoceptor agonist and antagonist. Tetrahedron 1991;47:9953-9980.
    • (1991) Tetrahedron , vol.47 , pp. 9953-9980
    • Ruffolo, R.R.1
  • 19
    • 0028928186 scopus 로고
    • Direct enantiomer separations by high-performance liquid chromatography with chiral urea derivatives as stationary phases
    • Ôi N, Kitahara H, Aoki F. Direct enantiomer separations by high-performance liquid chromatography with chiral urea derivatives as stationary phases. J Chromatogr A 1995;694:129-134.
    • (1995) J Chromatogr A , vol.694 , pp. 129-134
    • Ôi, N.1    Kitahara, H.2    Aoki, F.3
  • 20
    • 34447520818 scopus 로고    scopus 로고
    • Advanced Separation Technologies, Whippany NJ;
    • LC Application Report. Advanced Separation Technologies, Whippany NJ; 2006.
    • (2006) LC Application Report
  • 21
    • 0000999648 scopus 로고
    • High pressure liquid chromatography on triacetylcellulose. Characterization of a sorbent for separation of enantiomers
    • Koller H, Rimbock K-E, Mannschreck A. High pressure liquid chromatography on triacetylcellulose. Characterization of a sorbent for separation of enantiomers. J Chromatogr 1983;282:89-94.
    • (1983) J Chromatogr , vol.282 , pp. 89-94
    • Koller, H.1    Rimbock, K.-E.2    Mannschreck, A.3
  • 23
    • 28944443689 scopus 로고    scopus 로고
    • Chiral separation of amines by high-performance liquid chromatography using polysaccharide stationary phases and acidic additives
    • Stringham RW, Ye YK. Chiral separation of amines by high-performance liquid chromatography using polysaccharide stationary phases and acidic additives. J Chromatogr A 2006;1101:86-93.
    • (2006) J Chromatogr A , vol.1101 , pp. 86-93
    • Stringham, R.W.1    Ye, Y.K.2
  • 24
    • 0029968174 scopus 로고    scopus 로고
    • Significance of mobile phase composition in enantioseparation of chiral drugs by HPLC on a cellulose-based chiral stationary phases
    • Tang Y. Significance of mobile phase composition in enantioseparation of chiral drugs by HPLC on a cellulose-based chiral stationary phases. Chirality 1996;8:136-142.
    • (1996) Chirality , vol.8 , pp. 136-142
    • Tang, Y.1
  • 25
    • 0032828737 scopus 로고    scopus 로고
    • Application and comparison of derivatized cellulose and amylose chiral stationary phases for the separation of enantiomers of pharmaceutical compounds by high-performance liquid chromatography
    • Wang T, Chen YW. Application and comparison of derivatized cellulose and amylose chiral stationary phases for the separation of enantiomers of pharmaceutical compounds by high-performance liquid chromatography. J Chromatogr A 1999;855:411-421.
    • (1999) J Chromatogr A , vol.855 , pp. 411-421
    • Wang, T.1    Chen, Y.W.2
  • 26
    • 0034637271 scopus 로고    scopus 로고
    • Resolution of inherently chiral calix[4]arenes with AABB and CDCD substitution patterns on the upper and lower rims, respectively
    • Caccamese S, Bottino A Cunsolo F, Parlato S, Neri P. Resolution of inherently chiral calix[4]arenes with AABB and CDCD substitution patterns on the upper and lower rims, respectively. Tetrahedron Asymm 2000;11:3103-3112.
    • (2000) Tetrahedron Asymm , vol.11 , pp. 3103-3112
    • Caccamese, S.1    Bottino, A.2    Cunsolo, F.3    Parlato, S.4    Neri, P.5
  • 27
    • 0036470744 scopus 로고    scopus 로고
    • Memory effect of mobile phase additives in chiral separations on a Chiralpak AD column
    • Ye YK, Lord B, Stringham RW. Memory effect of mobile phase additives in chiral separations on a Chiralpak AD column. J Chromatogr A 2002;945:139-146.
    • (2002) J Chromatogr A , vol.945 , pp. 139-146
    • Ye, Y.K.1    Lord, B.2    Stringham, R.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.