Isolation and stereospecific determination of the enantiomers of oxindazac by direct liquid chromatographic resolution on triacetylcellulose

Francotte, Eric; Stierlin, H; Faigle, J. W.

doi:10.1016/s0021-9673(00)90518-1

Cited by 19 publications

(3 citation statements)

References 17 publications

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“…The same strategy was applied to determine the enantioselectivity of the pharmacokinetics of the enantiomers of the drug oxindanac in humans. [17] This was one of the very first applications of direct chromatographic separation of enantiomers and the first using a polysaccharide-based CSP for pharmacological studies. In this case, the chiral lability of the acid (drug) derivatizing group in the chiral discrimination process with CTA I, even though this group is relatively remote from the chiral center.…”

Section: Oligo-and Polysaccharides In Enantioselective Separationsmentioning

confidence: 99%

Polysaccharide Derivatives as Unique Chiral Selectors for Enantioselective Chromatography

Francotte

2017

Chimia

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From the beginning of the 1980s, the life science industry increasingly recognized the importance of chirality in biological interaction processes, but the methods for preparing optically pure drugs were still limited. Most of the syntheses of chiral compounds were performed starting from optically active building blocks (chiral pool), mainly from natural sources, or by resolution of the enantiomers via formation of diastereomers. In this context, there was a growing interest for enantioselective processes, such as synthetic methodologies and separation techniques for accessing optically pure substances in an effective manner. Among the separation approaches, enantioselective chromatography looked very promising and a project aiming to explore this option was started in the Central Research Laboratories of former Ciba-Geigy. This article reviews the story of this development which culminated in the discovery of highly efficient polysaccharide-based chiral stationary phases which have now become the gold standard in the world of enantioselective chromatography. It shows also how the technique of enantioselective chromatography has evolved from an analytical tool to a practical preparative technology, up to production scale.

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Section: Oligo-and Polysaccharides In Enantioselective Separationsmentioning

confidence: 99%

Polysaccharide Derivatives as Unique Chiral Selectors for Enantioselective Chromatography

Francotte

2017

Chimia

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“…3). [12] The preparative potential of the technique to produce optically pure chiral drugs in large amounts was simultaneously exploited and led, as early as 1985, to the construction of the largest chiral column ever packed with cellulose triacetate (Fig. 4).…”

Section: The Development and Application Of Chiral Stationary Phasesmentioning

confidence: 99%

Enantioselective Chromatography: From its Emergence to its Successful Implementation in the Pharmaceutical Environment

Francotte¹

2009

Chimia

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The author describes the emergence and development of enantioselective chromatography as a powerful tool for the separation of stereoisomers, on analytical, preparative, and production scale. He summarizes his early contribution to the advance and propagation of this particular technology at the interface between chemistry, separation sciences, and physics, going back to his growing interest in chirality which was stimulated by a postdoctoral stay at the University of Geneva.

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“…Several chiral drugs were first obtained in enantiomerically pure form using this technique, such as the diuretics chlorthalidone [11] and benzothiadiazines [12], the benzodiazepinone oxazepam [13], the muscle relaxant chlormezanone [14], hypnotic and anticonvulsant methaqualone [15], the anti-inflammatory drug oxindanac [16], and the antiaromatase fadrozole [17]. Several chiral drugs were first obtained in enantiomerically pure form using this technique, such as the diuretics chlorthalidone [11] and benzothiadiazines [12], the benzodiazepinone oxazepam [13], the muscle relaxant chlormezanone [14], hypnotic and anticonvulsant methaqualone [15], the anti-inflammatory drug oxindanac [16], and the antiaromatase fadrozole [17].…”

Section: Brief Overview Of Enantioseparation Techniques 21 Preparatimentioning

confidence: 99%

Enantioseparation of chiral drugs and current status of electromigration techniques in this field

Chankvetadze

2001

J. Sep. Science

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Isolation and stereospecific determination of the enantiomers of oxindazac by direct liquid chromatographic resolution on triacetylcellulose

Cited by 19 publications

References 17 publications

Polysaccharide Derivatives as Unique Chiral Selectors for Enantioselective Chromatography

Polysaccharide Derivatives as Unique Chiral Selectors for Enantioselective Chromatography

Enantioselective Chromatography: From its Emergence to its Successful Implementation in the Pharmaceutical Environment

Enantioseparation of chiral drugs and current status of electromigration techniques in this field

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