The mechanism of the formation of enantiotropic polymorphs of carisbamate in solution crystallization

Wu, Wen-Rong; Mehrman, Stephen J.; Zhou, Yong; Pu, Lian; Fermier, Adam; Karki, Shyam

doi:10.1016/j.jcrysgro.2009.03.051

Cited by 4 publications

(1 citation statement)

References 34 publications

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“…The measurement principle of the Raman spectroscopic probe is to send into the suspension a monochromatic beam and to analyse the scattered wave. This analytical technique is sensitive to compounds both in dry and wet states, and can hence be used to identify the crystals in suspension [10][11][12][13]. Figure 4 shows the Raman spectra of dry morph I crystals (black line) and dry morph II crystals (grey line), both obtained through a 120 seconds exposition time at 785 nm.…”

Section: Application To the Etiracetam Compoundmentioning

confidence: 99%

Towards an accurate and precise determination of the solid–solid transition temperature of enantiotropic systems

Herman

Leyssens

Vermylen

et al. 2011

The Journal of Chemical Thermodynamics

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Section: Application To the Etiracetam Compoundmentioning

confidence: 99%

Towards an accurate and precise determination of the solid–solid transition temperature of enantiotropic systems

Herman

Leyssens

Vermylen

et al. 2011

The Journal of Chemical Thermodynamics

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Rational polymorph screening based on slow cooling crystallization of poorly soluble mebendazole

Karashima

Kimoto

Kojima

et al. 2014

Journal of Crystal Growth

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Use of in Situ Raman, FBRM, and ATR-FTIR Probes for the Understanding of the Solvent-Mediated Polymorphic Transformation of II–I Etiracetam in Methanol

Herman

Haut

Douieb

et al. 2011

Org. Process Res. Dev.

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The objective of the present paper is to show the utility of combining distinct online and in situ probes, tracking both the solid and the liquid phases, to come to a full understanding of the mechanism underlying polymorphic transformations. The study focuses on the batch crystallization process of etiracetam (racemic intermediate to the synthesis of levetiracetam [Keppra, UCB Pharma], presenting two enantiotropically related crystallographic forms) in methanol, as this process relies on a polymorphic transformation in solution prior to the isolation of the final compound. The polymorphic transformation is shown to follow a solvent-mediated polymorphic transformation mechanism, which is characterized by three successive phases. Identification and understanding of each of these phases requires the knowledge on the nature of the crystallographic form (Raman probe), the variations in particle size distributions (FBRM probe) as well as the solute concentration in solution (ATR-FTIR probe), showing the necessity of combining these different online analyzers.

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The mechanism of the formation of enantiotropic polymorphs of carisbamate in solution crystallization

Cited by 4 publications

References 34 publications

Towards an accurate and precise determination of the solid–solid transition temperature of enantiotropic systems

Towards an accurate and precise determination of the solid–solid transition temperature of enantiotropic systems

Rational polymorph screening based on slow cooling crystallization of poorly soluble mebendazole

Use of in Situ Raman, FBRM, and ATR-FTIR Probes for the Understanding of the Solvent-Mediated Polymorphic Transformation of II–I Etiracetam in Methanol

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