Article Dans Une Revue Crystal Growth & Design Année : 2024

Unraveling a unique metastable phase of a proxyphylline cocrystal exclusively produced by compressed carbon dioxide

Léa Nimod
  • Fonction : Auteur
Isabelle Ziri
  • Fonction : Auteur

Résumé

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.

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Dates et versions

hal-04594447 , version 1 (30-05-2024)

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Fatma Ercicek, Mathieu Marchivie, Léa Nimod, Hugo Cercel, Clément Brandel, et al.. Unraveling a unique metastable phase of a proxyphylline cocrystal exclusively produced by compressed carbon dioxide. Crystal Growth & Design, 2024, 24 (11), pp.2024-073. ⟨10.1021/acs.cgd.4c00279⟩. ⟨hal-04594447⟩
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