2018
DOI: 10.1002/ceat.201700427
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Abstract: Numerous pharmaceutical ingredients are chiral and generally only one isomer shows the desired therapeutic activity. Therefore, enantioseparation, e.g., by crystallization, is a key step in the pharmaceutical industry. In this work, ternary phase diagrams of the diastereomeric salt formation of ibuprofen lysine in aqueous ethanol are generated. The solubilities of the formed diastereomeric salts are measured in a defined temperature range. Investigation of the X‐ray powder diffraction patterns confirmed ibupro… Show more

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Cited by 11 publications
(10 citation statements)
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“…Characteristic differences in the solubilities of the S ‐ibuprofen‐ S ‐lysine and R ‐ibuprofen‐ S ‐lysine (these will be referred to as the p ‐salt and n ‐salt, respectively, in this article) have been previously studied in a 94 wt % aqueous ethanol system, where the eutectic composition is ~66% p ‐salt . In the present work, the ternary phase diagram (TPD) is used to resolve pure diastereomeric salts of ibuprofen lysine by batch crystallization via both sequential batch and sequential coupled batch crystallization; the performance of these two approaches are analyzed and compared.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Characteristic differences in the solubilities of the S ‐ibuprofen‐ S ‐lysine and R ‐ibuprofen‐ S ‐lysine (these will be referred to as the p ‐salt and n ‐salt, respectively, in this article) have been previously studied in a 94 wt % aqueous ethanol system, where the eutectic composition is ~66% p ‐salt . In the present work, the ternary phase diagram (TPD) is used to resolve pure diastereomeric salts of ibuprofen lysine by batch crystallization via both sequential batch and sequential coupled batch crystallization; the performance of these two approaches are analyzed and compared.…”
Section: Introductionmentioning
confidence: 99%
“…Within the three‐phase region, crystallization of both salts can occur. The solubility and metastable zone width of both the pure salts were previously established by Simon et al …”
Section: Introductionmentioning
confidence: 99%
“…Ketoprofen [36] 5-ethyl-5-methylhydantoin [39] Threonine [42] Aspartic acid and glutamic acid [43] Propranolol [44] N-methylamphetamine [45] Threonine [46] Mandelic acid [47] Chiral microspheres based on poly(N-vinyl a-L-phenylalanine) [48] Benzo-(c)phenanthrene, 3,4-dehydroproline anhydride, and 2,6-dimethylglycoluril [49] 2-(2-oxopyrrolidin-1-yl)butanamide [50] Allenyl-bis-phosphine oxides [51] Leucine [52] Ibuprofen lysine [53] Racemic crystals, in turn, require suitable resolving agents, which are optically active compounds that aid in their non-spontaneous separation. Resolving agents convert the enantiomeric pair into two different diastereomers (geometric isomers, see Table 1) with different Physico-chemical properties, as they are different compounds, such as solubility, thus, facilitating their separation [44,54].…”
Section: Enantiomersmentioning
confidence: 99%
“…The introduction of continuous processing has been a paradigm shift in safety and productivity in the synthesis and isolation of active pharmaceutical ingredients (APIs) in both industry and academic research (Mascia et al, 2013 andLee et al, 2015 and references contained therein). A major focus of our current research is developing design and optimization strategies to deliver robust, scalable and tunable continuous processes for API manufacturing, which can deliver specific API characteristics (Power et al, 2015;Zhao et al, 2015;O'Mahony et al, 2017;Simon et al, 2018). As part of this work we have been examining the continuous crystallization of 2-chloro-N-(p-tolyl)propanamide, 1, a key intermediate of -thio--chloroacrylamides, a class of compound that has shown importance in the literature as synthetically viable APIs (Murphy et al, 2007;Foley et al, 2011;) that can undergo transformations; such as Diels-Alder cycloadditions (Kissane et al, 2010a), 1,3-dipolar cycloadditions (Kissane et al, 2010b), sulfide group (Kissane et al, 2010c,d) and nucleophilic substitution .…”
Section: Chemical Contextmentioning
confidence: 99%