Rare Case of Polymorphism in the Binary System of Enantiomers of a Praziquantel Derivative - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Process Research and Development Année : 2024

Rare Case of Polymorphism in the Binary System of Enantiomers of a Praziquantel Derivative

Clément Pinètre
Loïc Ritou
  • Fonction : Auteur
Charline Gerard
Hugo Cercel
  • Fonction : Auteur
Michel Leeman
  • Fonction : Auteur
Richard Kellogg
Paul Tinnemans
  • Fonction : Auteur
Morgane Sanselme
  • Fonction : Auteur
Clément Brandel
Valérie Dupray
Joop ter Horst

Résumé

A rare caseof a polymorphicracemiccompoundhas beendiscoveredin the binarysystemof enantiomersof thepraziquantelderivative2-(cyclopropanecarbonyl)dodecahydro-4H-pyrazino[2,1-a]isoquinolin-4-one.Solid-statecharacterizationofthe threepolymorphshas beenperformed,includingthe resolutionof theircrystalstructuresand the constructionof a binaryphasediagrambetweenthe enantiomers.Althoughthe threepolymorphsdemonstratehighkineticstabilityat roomtemperature,athoroughexaminationof the binaryphasediagramthroughthermodynamicconsiderationrevealsa complexsituationin whichthethreeracemicformsare foundto be enantiotropicallyrelated.As a resultof majorstructuraldifferencesbetweenthe polymorphs,nosolid−solidpolymorphictransitionwas observed,and the conversionfromone formto the othersystematicallyrequiredmeltingandrecrystallization.Suchenantiotropicbehavioris rarelyobservedand highlightsthe diversityof crystallizationbehaviorsthat can resultfromslightchemicalmodification.
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Dates et versions

hal-04533952 , version 1 (05-04-2024)

Identifiants

Citer

Clément Pinètre, Loïc Ritou, Charline Gerard, Hugo Cercel, Michel Leeman, et al.. Rare Case of Polymorphism in the Binary System of Enantiomers of a Praziquantel Derivative. Organic Process Research and Development, 2024, ⟨10.1021/acs.oprd.4c00035⟩. ⟨hal-04533952⟩
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