• Title/Summary/Keyword: (S)-Naproxen

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Performance of HPLC Chiral Stationary Phases with Two Chiral Units and the Effect of the Stereochemistry of the Second Chiral Unit on the Chiral Recognition

  • 현명호;황승렬;한상철
    • Bulletin of the Korean Chemical Society
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    • v.20 no.11
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    • pp.1309-1312
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    • 1999
  • Two chiral stationary phases (CSPs) derived from two diastereomers consisting of (R)- or(S)-α-naphthylethylamine and (S)-naproxen were found to show different chromatographic behaviors in resolving N-(3,5-dinitrobenzoyl)-α-arylalkylamines and N-(3,5-dinitrobenzoyl)-α- or β-amino amides and esters. From the different chromatographic resolution behaviors on the two CSPs, the chiral recognition is proposed to be controlled mainly by the (R)- or (S)-α-naphthylethylamine part of the CSP. In contrast, the (S)-naproxen part of the two CSPs is proposed to exert some subordinate effects on the chiral recognition.

A Kinetic Consideration on the Selective Adsorption and Molecular Recognition by Molecularly Imprinted Polymer

  • Li, Wuke;Li, Songjun;Luo, Gang;Ding, Kerong
    • Bulletin of the Korean Chemical Society
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    • v.28 no.8
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    • pp.1346-1352
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    • 2007
  • This article presents an original work on kinetically studying the selective adsorption and recognition by molecularly imprinted polymer (MIP). With S-naproxen as template, the imprinted polymer was prepared. The result indicates that the prepared polymer shows a more complicated sorption toward S-naproxen than toward its enantiomer R-naproxen. The rate constant in the case of template appears to be a variable. There are also significant deviations from the idealized Langmuir model. Related information indicates that these, in logic, can be a result of biomimic structural and functional complements between imprint and the template, which makes the polymer capable of selectively recognizing the imprint species.

Indirect chiral separation of $\alpha$-arylmethylpropionic acids by liquid chromatography

  • Min, Chung-Sik;Jang, Seung-Jae;Choi, Bo-Kyung;Kim, Young-Lim;Jung, Hae-Yun;Bak, Kyung-Min;Lee, Kyung-Hee;Jo, Keang-In;Gu, You-Ni
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.215.1-215.1
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    • 2003
  • A various ${\alpha}$-arylmethylpropionic acids(profen) have been widely used as non-steroidal anti-inflammatory drugs for the relief of acute and chronic rheumatoid arthritis and osteoarthritis, as well as for other connective tissue disorders and pains. Example is fenoprofen, ibuprofen, ketoprofen, and naproxen. All are chiral and, except for naproxen and ibuprofen, are marketed in racemic form. Enantioseparations of profens have been of considerable interest becaus their anti-inflammatory and analgesic effects have been attirbuted almost exclusively to their (S)-enantiomer. (omitted)

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Determination of Optical Purity of a-Arylmethylpropionic acds by Normal Phase Liquid Chromatography

  • Min-Chungsik;Jae, Jang-Seung;Lee, Song-Deuk;Park, Seung-Hee;Yun, Jang-Jung;Yun, Jung-Hae;Lee, Keang-Hee;Hae, Jo-Seung;In, Jo-Keang
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.241.2-241.2
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    • 2002
  • A various 2-arylmethylpropionic acds(profen) have been widely used as non-steroidal anti-inllammatory drugs for the relief of acute and chronic rheumatoid arthritis and osteoarthritis. as well as for other connective tissue disorders and pains. Example is fenoprofen. ibuprofen, ketoprolen, and naproxen. All are chiral and, except for naproxen. are marketed in racemic form. Enantioseparations of profens have been of considerable interest because their anti-inflammatory and analgesic effects have been attributed almost exclusively to their (S)-enantiomer. (omitted)

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Solid Bases as Racemization Catalyst for Lipase-catalyzed Dynamic Kinetic Resolution of Naproxen 2,2,2-Trifluoroethyl Thioester (리파아제에 의한 나프록센 2,2,2-트리플로로에틸 씨오에스터의 Dynamic Kinetic Resolution을 위한 라세미화 촉매로서의 고체 염기)

  • 김상범;원기훈;문상진;김광제;박홍우
    • KSBB Journal
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    • v.19 no.3
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    • pp.215-220
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    • 2004
  • A variety of solid bases such as inorganic bases, basic anion exchange resins, and resin-bound bases were tested as a catalyst for racemization of (S)-naproxen 2,2,2-trifluoroethyl thioester in isooctane at 45$^{\circ}C$. Among the various bases, DIAIOM WA30, which is a weakly basic anion exchange resin with a tertiary amine based on a highly porous type styrene-divinylbenzene copolymer, showed the highest catalytic activity. The second-order interconversion constant of DIAION WA30 was 8.6${\times}$10$\^$-4/ mM$\^$-1/h$\^$-1/ and about 3 times higher than that of trioctylamine under the same conditions. The rate of DIAION WA30-catalyzed racemization decreased with increasing an amount of water added to the reaction medium. Lipase-catalyzed kinetic resolution of racemic naproxen 2,2,2-trifluoroethyl thioester was successfully carried out under in situ racemization of substrate with DIAION WA30 in isooctane at 45$^{\circ}C$. More than 60% conversion and 99% enantiomeric excess for the desired (S)-naproxen product were obtained. Furthermore, such a solid base catalyst could be easily separated and reused in contrast to trioctylamine.

Preparation of a New Chiral Stationary Phase Bearing Both $\pi$-Acidic and -Basic Sites from (S)-Naproxen for the Liquid Chromatographic Resolution of Enantiomers

  • Hyun Myung Ho;Jin Jong Sung;Ryoo Jae-Jeong;Jyung Kyung Kyu
    • Bulletin of the Korean Chemical Society
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    • v.15 no.6
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    • pp.497-502
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    • 1994
  • A new chiral stationary phase (CSP) for the liquid chromatographic resolution of enantiomers was prepared from (S)-naproxen and 3,5-dinitroaniline. The 6-alkoxy-2-naphthyl group of the CSP was presumed to act as a ${\pi}$-basic interaction site for resolving ${\pi}$-acidic racemates while the 3,5-dinitroanilide group of the CSP was presumed to play a role as a ${\pi}$-acidic interaction site for resolving ${\pi}$-basic racemates. From the chromatographic resolution trends of N-alkylamide derivatives of ${\alpha}$-arylalkylamines on the CSP prepared, the chiral recognition mode involving the intercalation of the amide alkyl chain of the less retained enantiomers between the connecting tethers of the CSP was proposed.

APPLICATION OF STABLE EMULSIONS TO LIPASE IMMOBILISED MEMBRANE REACTORS FOR KINETIC RESOLUTION OF RACEMIC ESTERS

  • Giorno, Lidietta;Na, Li;Drioli, Enrico
    • Proceedings of the Membrane Society of Korea Conference
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    • 2003.07a
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    • pp.65-68
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    • 2003
  • The paper discusses the use of stable emulsion, prepared by membrane emulsification technology, to improve the enantiocatalytic performance of immobilised lipase in multiphasic membrane reactors. The production of optical pure (S)-naproxen from racemic naproxen methyl ester has been used as model reaction system. The enzyme was immobilised in the sponge layer (shell side) of capillary polyamide membrane with 50 kDa cut-off, The O/W emulsion, containing the substrate in the organic dispersed phase, was fed to the enzyme membrane reactor from shell-to-lumen. The results evidenced that lipase maintained stable activity during all the operation time (more than 250 hours), showing an enantiomeric excess (96 $\pm$2%) comparable to the free enzyme (98 $\pm$ 1%) and much higher compared to similar lipase-loaded membrane reactors used in two-separate phase systems (90%). The study showed that immobilised enzymes can achieve high stability as well as high catalytic activity and enantioselectivity.

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A Methocarbamol Combination to Prevent Toxicity of Non-steroidal Anti Inflammatory Drugs (비스테로이드성 항염증제의 약물독성 예방을 위한 Methocarbamol의 약물조합)

  • Yeom, Seung-Min;Kim, Min-Seok;Lingenfelter, Eric;Broadwell, Jonathan
    • Korean Journal of Clinical Laboratory Science
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    • v.49 no.2
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    • pp.88-98
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    • 2017
  • To prevent toxicity from both robax platinum (methocarbamol, ibuprofen) and robaxacet (methocarbomol, acetaminophen), separately, we used stretches and naproxen as a non-steroidal anti-inflammatory drug (NSAID) to compare each effectiveness. This study used the United States Forces Korea Prescription form (Annex A-Over-The-Counter Prescription) and Alice Rich's Pain scale with robax platinum, robaxacet including narproxen. The IBM SPSS statics version 24 was used to calculate the data. The combined methocarbamol 500 mg, acetaminophen 325 mg tablet, and ibuprofen 200 mg (or naproxen) tablet can work as well as the combined methocarbamol 500 mg tablet with acetaminophen 325 mg tablet with stretches. Both methods were successful in managing pain. The drug combination of methocarbamol 500 mg, acetaminophen 325 mg and ibuprofen 200 mg tablets yielded similar benefits as the methocarbamol 500 mg and acetaminophen 325 mg tablets paired with physical stretching exercises regarding managing overall pain.

Measurement of optical purity for commercial naproxen by chiral HPLC (키랄 크로마토그래피에 의한 시판되는 나프록센의 광학순도 측정)

  • Yu, Jeong-Jae;Lee, Won-Doo;Ryoo, Jae-Jeong
    • Analytical Science and Technology
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    • v.24 no.5
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    • pp.360-367
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    • 2011
  • Optical purities of 10 commercialized naproxens prepared from eight Korean drug companies were examined by an optimized chiral HPLC condition. The Chiralcel OD-H column and ChiralHyun-LE(S)-1 column were used as chiral stationary phases and the mixed eluent of hexane/isopropanol/acetic acid as 100:2.85:0.1 was used as a mobile phase for effective enantioseparation. Optical purity values of most samples were higher than 97 percents, only one of them was about 95 percents. The average relative standard deviation of them appeared very small (0.034%).