Chiral Resolution of RS-Oxiracetam upon Cocrystallization with Pharmaceutically Acceptable Inorganic Salts

Oleksii Shemchuk; Lixing Song; Nikolay Tumanov; Johan Wouters; Dario Braga; Fabrizia Grepioni; Tom Leyssens

doi:10.1021/acs.cgd.9b01725

Chiral Resolution of RS-Oxiracetam upon Cocrystallization with Pharmaceutically Acceptable Inorganic Salts

Oleksii Shemchuk, Lixing Song, Nikolay Tumanov, Johan Wouters, Dario Braga, Fabrizia Grepioni, Tom Leyssens

Research output: Contribution to journal › Article › peer-review

Abstract

Ionic cocrystals (ICCs) of racemic RS-oxiracetam and of its active S-enantiomer of pharmaceutical interest with the pharmaceutically acceptable salts calcium and magnesium chloride were synthesized and structurally characterized. The cocrystallization of RS-oxiracetam with MgCl₂ resulted in chiral resolution with formation of an S-OXI·MgCl₂·5H₂O/R-OXI·MgCl₂·5H₂O conglomerate. Ternary phase diagrams of RS-oxiracetam/inorganic salt/solvent were constructed to determine the overall compositions for which the ICCs are the only stable phases in suspension. In addition, single crystals of S-oxiracetam were grown, and its structure was determined.

Original language	English
Pages (from-to)	2602-2607
Number of pages	6
Journal	Crystal Growth and Design
Volume	20
Issue number	4
DOIs	https://doi.org/10.1021/acs.cgd.9b01725
Publication status	Published - 1 Apr 2020

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10.1021/acs.cgd.9b01725

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title = "Chiral Resolution of RS-Oxiracetam upon Cocrystallization with Pharmaceutically Acceptable Inorganic Salts",

abstract = "Ionic cocrystals (ICCs) of racemic RS-oxiracetam and of its active S-enantiomer of pharmaceutical interest with the pharmaceutically acceptable salts calcium and magnesium chloride were synthesized and structurally characterized. The cocrystallization of RS-oxiracetam with MgCl2 resulted in chiral resolution with formation of an S-OXI·MgCl2·5H2O/R-OXI·MgCl2·5H2O conglomerate. Ternary phase diagrams of RS-oxiracetam/inorganic salt/solvent were constructed to determine the overall compositions for which the ICCs are the only stable phases in suspension. In addition, single crystals of S-oxiracetam were grown, and its structure was determined.",

author = "Oleksii Shemchuk and Lixing Song and Nikolay Tumanov and Johan Wouters and Dario Braga and Fabrizia Grepioni and Tom Leyssens",

note = "Funding Information: This material is based on the work of L.S., supported by the China Scholarship Council and FNRS (PDR T.0149.19). The Universities of Bologna (O.S., D.B., and F.G.–RFO scheme) and Namur (N.T. and J.W.), and the Universit{\'e} Catholique de Louvain (T.L.), are also acknowledged. Funding Information: This material is based on the work of L.S., supported by the China Scholarship Council and FNRS (PDR T.0149.19). The Universities of Bologna (O.S., D.B., and F.G.?RFO scheme) and Namur (N.T. and J.W.), and the Universit? Catholique de Louvain (T.L.) are also acknowledged. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.cgd.9b01725",

language = "English",

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T1 - Chiral Resolution of RS-Oxiracetam upon Cocrystallization with Pharmaceutically Acceptable Inorganic Salts

AU - Shemchuk, Oleksii

AU - Song, Lixing

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Braga, Dario

AU - Grepioni, Fabrizia

AU - Leyssens, Tom

N1 - Funding Information: This material is based on the work of L.S., supported by the China Scholarship Council and FNRS (PDR T.0149.19). The Universities of Bologna (O.S., D.B., and F.G.–RFO scheme) and Namur (N.T. and J.W.), and the Université Catholique de Louvain (T.L.), are also acknowledged. Funding Information: This material is based on the work of L.S., supported by the China Scholarship Council and FNRS (PDR T.0149.19). The Universities of Bologna (O.S., D.B., and F.G.?RFO scheme) and Namur (N.T. and J.W.), and the Universit? Catholique de Louvain (T.L.) are also acknowledged. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/4/1

Y1 - 2020/4/1

N2 - Ionic cocrystals (ICCs) of racemic RS-oxiracetam and of its active S-enantiomer of pharmaceutical interest with the pharmaceutically acceptable salts calcium and magnesium chloride were synthesized and structurally characterized. The cocrystallization of RS-oxiracetam with MgCl2 resulted in chiral resolution with formation of an S-OXI·MgCl2·5H2O/R-OXI·MgCl2·5H2O conglomerate. Ternary phase diagrams of RS-oxiracetam/inorganic salt/solvent were constructed to determine the overall compositions for which the ICCs are the only stable phases in suspension. In addition, single crystals of S-oxiracetam were grown, and its structure was determined.

AB - Ionic cocrystals (ICCs) of racemic RS-oxiracetam and of its active S-enantiomer of pharmaceutical interest with the pharmaceutically acceptable salts calcium and magnesium chloride were synthesized and structurally characterized. The cocrystallization of RS-oxiracetam with MgCl2 resulted in chiral resolution with formation of an S-OXI·MgCl2·5H2O/R-OXI·MgCl2·5H2O conglomerate. Ternary phase diagrams of RS-oxiracetam/inorganic salt/solvent were constructed to determine the overall compositions for which the ICCs are the only stable phases in suspension. In addition, single crystals of S-oxiracetam were grown, and its structure was determined.

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Chiral Resolution of RS-Oxiracetam upon Cocrystallization with Pharmaceutically Acceptable Inorganic Salts

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Chiral Resolution of RS-Oxiracetam upon Cocrystallization with Pharmaceutically Acceptable Inorganic Salts

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