Direct and indirect separations of five isomers of Brivanib Alaninate using chiral high-performance liquid chromatography

被引：17

作者：

He, Brian Lingfeng ^{[1
]}

Shi, Yueer ^{[1
]}

Kleintop, Brent ^{[1
]}

Raglione, Thomas ^{[1
]}

机构：

[1] Bristol Myers Squibb Res & Dev, New Brunswick, NJ 08903 USA

来源：

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES | 2008年 / 875卷 / 01期

关键词：

Brivanib Alaninate; Chiral separation; Derivatization; Polysaccharide chiral stationary phases; HPLC;

D O I：

10.1016/j.jchromb.2008.08.022

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Brivanib Alaninate is a novel chiral prodrug possessing two stereogenic centers. Simultaneous HPLC separation of five isomers of Brivanib Alaninate was systematically investigated on a wide variety of polysaccharide-based chiral stationary phases (CSPs) using underivatization and pre-column derivatization methods. The influence of derivatizing groups and mobile phase composition on the enantioseparation and retention behavior of Brivanib Alaninate compounds was studied. To better understand the chiral recognition mechanism, the temperature effect was also evaluated. The results of these studies led to the first complete HPLC resolution of all five isomers of Brivanib Alaninate as carbobenzyloxy (CBZ) derivatives on a cellulose benzoate CSP (OJ-H). (c) 2008 Elsevier B.V. All rights reserved.

引用

页码：122 / 135

页数：14

共 33 条

[1] High-performance liquid chromatographic enantioseparation of drags containing multiple chiral centers on polysaccharide-type chiral stationary phases [J].

Aboul-Enein, HY .

JOURNAL OF CHROMATOGRAPHY A, 2001, 906 (1-2) :185-193

[2] QUANTITATIVE-DETERMINATION OF PHENYL ISOTHIOCYANATE-DERIVATIZED AMINO-SUGARS AND AMINO SUGAR ALCOHOLS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

ANUMULA, KR ;

TAYLOR, PB .

ANALYTICAL BIOCHEMISTRY, 1991, 197 (01) :113-120

[3] Temperature and enantioseparation by macrocyclic glycopeptide chiral stationary phases [J].

Berthod, A ;

He, BLF ;

Beesley, TE .

JOURNAL OF CHROMATOGRAPHY A, 2004, 1060 (1-2) :205-214

[4] Discovery of brivanib alaninate ((S)-((R)-1-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yloxy)propan-2-yl)2-aminopropanoate), a novel prodrug of dual vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1 kinase inhibitor (BMS-540215) [J].

Cai, Zhen-Wei ;

Zhang, Yongzheng ;

Borzilleri, Robert M. ;

Qian, Ligang ;

Barbosa, Stephanie ;

Wei, Donna ;

Zheng, Xiaoping ;

Wu, Lawrence ;

Fan, Junying ;

Shi, Zhongping ;

Wautlet, Barri S. ;

Mortillo, Steve ;

Jeyaseelan, Robert, Sr. ;

Kukral, Daniel W. ;

Kamath, Amrita ;

Marathe, Punit ;

D'Arienzo, Celia ;

Derbin, George ;

Barrish, Joel C. ;

Robl, Jeffrey A. ;

Hunt, John T. ;

Lombardo, Louis J. ;

Fargnoli, Joseph ;

Bhide, Rajeev S. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) :1976-1980

[5] 3-fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatographic enantioseparation [J].

Chankvetadze, B ;

Chankvetadze, L ;

Sidamonidze, S ;

Kasashima, E ;

Yashima, E ;

Okamoto, Y .

JOURNAL OF CHROMATOGRAPHY A, 1997, 787 (1-2) :67-77

[6] CHLOROMETHYLPHENYLCARBAMATE DERIVATIVES OF CELLULOSE AS CHIRAL STATIONARY PHASES FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

CHANKVETADZE, B ;

YASHIMA, E ;

OKAMOTO, Y .

JOURNAL OF CHROMATOGRAPHY A, 1994, 670 (1-2) :39-49

[7] Enantioseparation of selected chiral sulfoxides using polysaccharide-type chiral stationary phases and polar organic, polar aqueous-organic and normal-phase eluents [J].

Chankvetadze, B ;

Yamamoto, C ;

Okamoto, Y .

JOURNAL OF CHROMATOGRAPHY A, 2001, 922 (1-2) :127-137

[8] Comparative enantioseparation of selected chiral drugs on four different polysaccharide-type chiral stationary phases using polar organic mobile phases [J].

Chankvetadze, B ;

Kartozia, I ;

Yamamoto, C ;

Okamoto, Y .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2002, 27 (3-4) :467-478

[9] HPLC ENANTIOSEPARATION OF DIPEPTIDE AND TRIPEPTIDE ON CYCLODEXTRIN-BONDED STATIONARY PHASES AFTER DERIVATIZATION WITH 6-AMINOQUINOLYL-N-HYDROXYSUCCINIMIDYL CARBAMATE (AQC) [J].

CHEN, SS ;

PAWLOWSKA, M ;

ARMSTRONG, DW .

JOURNAL OF LIQUID CHROMATOGRAPHY, 1994, 17 (03) :483-497

[10] SYNTHESIS OF A FLUORESCENT DERIVATIZING REAGENT, 6-AMINOQUINOLYL-N-HYDROXYSUCCINIMIDYL CARBAMATE, AND ITS APPLICATION FOR THE ANALYSIS OF HYDROLYSATE AMINO-ACIDS VIA HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

COHEN, SA ;

MICHAUD, DP .

ANALYTICAL BIOCHEMISTRY, 1993, 211 (02) :279-287

← 1 2 3 4 →