Diastereomeric salt precipitation based resolution of ibuprofen by gas antisolvent method

Lőrincz, László; Bánsághi, György; Zsemberi, Máté; Brezmes, Sandra de Simón; Szilágyi, Imre Miklós; Madarász, János; Sohajda, Tamás; Székely, Edit

doi:10.1016/j.supflu.2016.07.021

Cited by 18 publications

(19 citation statements)

References 18 publications

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“…However, the effect is typically highly non-linear [36], as we also found in our current investigation (Figure 4.). During each measurement, the apparent salt concentration was constant (3.5 mg/ml) and the amount of methanol was varied.…”

Section: Carbon Dioxide-methanol Molar Ratiosupporting

confidence: 86%

“…Compared to the published optimised optical resolution of ibuprofen resulting in 0.43 [50], 0.42 [15], 0.44 [36], the novel method afforded selectivities as high as 0.55.…”

Section: Discussionmentioning

confidence: 94%

“…A description of the capillary electrophoresis, powder X-ray diffraction (XRD) and scanning electron microscopy (SEM) methods were published in our previous work [36].…”

Section: Discussionmentioning

confidence: 99%

“…A detailed description of the reactors can be found in our earlier paper [36]. After pipetting in the liquid solution of ibuprofen and the resolving agent, the reactor was sealed, then stirred at 750 rpm while pressurized with carbon dioxide to the desired pressure, typically within 10-15 minutes.…”

Section: Gas Antisolvent Fractionation Proceduresmentioning

confidence: 99%

“…2. ), CO 2 denotes the molar amount (mol) of carbon dioxide in the reactor that was calculated from the volume change of the syringe pump during pressurization of the reactor [36], while MeOH denotes the molar amount (mol) of methanol.…”

Section: Calculationsmentioning

confidence: 99%

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Gas antisolvent fractionation based optical resolution of ibuprofen with enantiopure phenylglycinol

Lőrincz

Tóth

Kondor

et al. 2018

Journal of CO2 Utilization

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Section: Carbon Dioxide-methanol Molar Ratiosupporting

confidence: 86%

“…Compared to the published optimised optical resolution of ibuprofen resulting in 0.43 [50], 0.42 [15], 0.44 [36], the novel method afforded selectivities as high as 0.55.…”

Section: Discussionmentioning

confidence: 94%

“…A description of the capillary electrophoresis, powder X-ray diffraction (XRD) and scanning electron microscopy (SEM) methods were published in our previous work [36].…”

Section: Discussionmentioning

confidence: 99%

Section: Gas Antisolvent Fractionation Proceduresmentioning

confidence: 99%

Section: Calculationsmentioning

confidence: 99%

See 3 more Smart Citations

Gas antisolvent fractionation based optical resolution of ibuprofen with enantiopure phenylglycinol

Lőrincz

Tóth

Kondor

et al. 2018

Journal of CO2 Utilization

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Towards Diastereomeric Pure Salts with Antisolvent Methods

et al. 2018

Self Cite

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Chiral molecules, especially enantiomers and diastereomers of purity > 99 %, present a significant market share within the chemical, pharmaceutical, and flavor industries. Antisolvent precipitations, both batch and semicontinuous operations to serve the current trends in flow chemistry were demonstrated to be environmentally benign and efficient tools in achieving high optical purities. Although salts are known to be insoluble in supercritical CO 2 , instabilities of the nascent salts were detected and applied for increasing efficiency. Diastereomeric excess values of the crystalline products exceeded 99 % in maximum of three consecutive steps both by repeated resolution with half molar equivalent of the amine to the acid and by direct recrystallization of the salts.

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Enantioselective separation and determination of ibuprofen: Stereoselective pharmacokinetics, pharmacodynamics and analytical methods

Vashistha,

Kumar,

Yadav

et al. 2024

Chirality

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Ibuprofen (IBP), the 29th most prescribed drug in the United States in 2019, is a widely used nonsteroidal anti‐inflammatory drug (NSAID) comprising two enantiomers, (R)‐IBP and (S)‐IBP, collectively known as (RS)‐IBP. This critical review examines analytical techniques for the enantioselective separation and determination of IBP enantiomers, crucial for pharmaceutical and clinical applications. The review focuses on state‐of‐the‐art methods, including chromatographic techniques including high‐performance liquid chromatography, gas chromatography, liquid chromatography–tandem mass spectrometry, and some other techniques. This review addresses pharmacokinetics, pharmacology, and side effects of each enantiomer, ensuring safe drug usage. By consolidating diverse analytical methods and their applicability in different matrices, this review serves as a valuable resource for researchers, analysts, and practitioners in pharmaceutical analysis, pharmacology, and clinical studies.

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Diastereomeric salt precipitation based resolution of ibuprofen by gas antisolvent method

Cited by 18 publications

References 18 publications

Gas antisolvent fractionation based optical resolution of ibuprofen with enantiopure phenylglycinol

Gas antisolvent fractionation based optical resolution of ibuprofen with enantiopure phenylglycinol

Towards Diastereomeric Pure Salts with Antisolvent Methods

Enantioselective separation and determination of ibuprofen: Stereoselective pharmacokinetics, pharmacodynamics and analytical methods

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