ERCICEK, Fatma; MARCHIVIE, Mathieu; NIMOD, Lea; CERCEL, Hugo; BRANDEL, Clement; ZIRI, Isabelle; CARTIGNY, Yohann; MONNIER, Olivier; MARRE, Samuel; SUBRA-PATERNAULT, Pascale; HARSCOAT-SCHIAVO, Christelle

doi:10.1021/acs.cgd.4c00279

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ERCICEK, Fatma
Chimie et Biologie des Membranes et des Nanoobjets [CBMN]

MARCHIVIE, Mathieu

NIMOD, Lea
SANOFI Recherche

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Article de revue

Ce document a été publié dans

Crystal Growth & Design. 2024-05-13, vol. 24, n° 11, p. 4271-4874

Résumé en anglais

In this work, racemic proxyphylline ((±)-PXL, a chiral drug) was cocrystallized for the first time with 4-hydroxybenzoic acid (4-HBA) from three solvents (acetone, ethyl acetate, and isobutanol) and using CO2 as an antisolvent. The obtained solid forms were compared to those produced by liquid-assisted grinding (LAG). It is shown that though both methods produce a racemic compound (±)-PXL1:4-HBA1 cocrystal, LAG promotes the crystallization of an orthorhombic Pna21 form (Phase I), whereas CO2-assisted crystallization gives rise to an original monoclinic C2/c form with partial inclusion of CO2 and water molecules (Phase II). The structure of Phase II originates from this inclusion since this phase is never obtained in the absence of CO2. Concomitant cocrystallization of Phase I and Phase II occurs during CO2-assisted crystallization in proportions that vary with solvents and temperature. Our study shows that Phase II transforms progressively into Phase I upon storage or heating.< Réduire

Mots clés en anglais

Crystal structure

Crystallization

Granular materials

Ketones

Solvents

URI

https://oskar-bordeaux.fr/handle/20.500.12278/206622

DOI

http://dx.doi.org/10.1021/acs.cgd.4c00279

Project ANR

Apport du CO2 dans le contrôle de phase cristalline - ANR-18-CE07-0047

Unités de recherche

CBMN : Chimie & de Biologie des Membranes & des Nano-objets - UMR 5248