Electrically controlled separation of maleic acid and fumaric acid through a poly(vinyl alcohol)/poly(acrylic acid) composite membrane

Kokufuta, Etsuo; Yamauchi, Takeshi; Osada, Yoshihito

doi:10.1016/0966-7822(94)00010-7

Cited by 12 publications

(1 citation statement)

References 9 publications

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“…Here, four structurally similar and pharmaceutically acceptable C4-dicarboxylic acids, maleic acid (MAL, Scheme b), fumaric acid (FUM, Scheme c), succinic acid (SUC, Scheme d), and l -tartaric acid (TAR, Scheme e), were selected to form cocrystals or organic salts with BAR. The acidic p K a data − of these guest molecules are given in Scheme . If a crystalline complex can be formed, we can only predict that SUC tends to form cocrystals with BAR according to the p K a rule (Δp K a < 0), and ionization states of other crystalline complexes are unpredictable (0 < Δp K a < 3) .…”

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Similarity and Diversity: Cocrystallization of Baricitinib with Four C4-Dicarboxylic Acids

Wang

Xie

Gao

et al. 2022

Crystal Growth & Design

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The structural resemblance strategy is an often-employed principle to guide the discovery of novel pharmaceutical cocrystals and salts. Here, baricitinib (BAR) was selected as a model compound due to the existence of abundant heterocyclic nitrogen sites (proton acceptor sites) to form crystalline complexes with four structurally similar and pharmaceutically acceptable C4-dicarboxylic acids, maleic acid (MAL), fumaric acid (FUM), succinic acid (SUC), and l-tartaric acid (TAR). Crystal structures, intermolecular interactions, and physicochemical properties of each resulting form were analyzed to demonstrate the similarity and diversity. BAR–MAL and BAR–TAR are two salts with stoichiometric ratios of 2:2 and 2:1, respectively. BAR–FUM and BAR–SUC are isostructural cocrystals with a stoichiometric ratio of 1:0.5. All of these new solid-state forms demonstrated excellent phase stability against hydration, reduced hygroscopicity, and slight solubility improvements, supporting their usage as alternative forms of BAR for generic drug development.

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confidence: 99%