• 제목/요약/키워드: Chiral drugs

검색결과 39건 처리시간 0.027초

Development and Application of Crown Ether-based HPLC Chiral Stationary Phases

  • Hyun, Myung-Ho
    • Bulletin of the Korean Chemical Society
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    • 제26권8호
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    • pp.1153-1163
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    • 2005
  • Crown ether-based HPLC chiral stationary phases (CSPs) have been successfully utilized in the resolution of various racemic compounds containing a primary amino group. Especially, CSPs based on chiral crown ethers incorporating chiral binaphthyl unit or tartaric acid unit and based on phenolic pseudo chiral crown ethers have shown high chiral recognition efficiency. In this account paper, a review on the development of crown etherbased HPLC CSPs, their structural characteristics and applications to the resolution of racemic compounds including chiral drugs containing a primary or secondary amino group with the variation of the type and the content of mobile phase components and with the variation of the column temperature is presented.

Chiral Separation of Non-Steroidal Inflarnrnatory Drugs and Metabolites by Achiral Gas Chromatography as O- Trifluoroacetylated (- )-Menthyl Esters

  • Lee, Yoon-Suk;Paik, Man-Jeong;Kim, Kyoung-Rae
    • 대한약학회:학술대회논문집
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    • 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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    • pp.396.3-397
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    • 2002
  • Because of the differences in biological and pharmacological properties between enantiomers of chiral acidic non-steroidal antiinflammatory drugs (NSAIDs) in human body. accurate determinations of their optical purities have been in great need. Racemic ibuprofen. tiaprofen. suprofen. flubiprofen and napoxen were reacted with (1R. 28. 5R)-(-)-menthol to convert them to corresponding diastereomeric (1R. 2S. 5R)-(- )-menthyl esters. (omitted)

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Simultaneous Chiral Discrimination of Nine Non-Steroidal Antiinflammatory Drugs by Cyclodextrin-Modified Capillary Electrophoresis in Normal and Reversed Polarity Modes

  • Kim, Ji-Yung;La, Sook-Ie;Kim, Jung-Han;Kim, Kyoung-Rae
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.276.2-276.2
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    • 2003
  • Simultaneous enantioseparation of nine racemic non-steroidal antiinflammatory drugs (NSAIDs) for their accurate chiral discrimination was achieved by cyclodextrin (CO) modified capillary electrophoresis in the normal polarity (NP) mode and in the reversed polarity (RP) mode. The NP mode employed neutral tri-O-methyl-${\beta}$-cyclodextrin (TM${\beta}$CD) as a selector dissolved in MES buffer (PH 6.0). (omitted)

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Enantiomeric Profiling Analysis of NSAIDs by Capillary Electrophoresis Using TM $\beta$-Cyclodextrin as the Chiral Selector

  • Kim, Ji-Young;La, Sookie;Kim, Jung-Han;Kim, Kyoung-Rae
    • 대한약학회:학술대회논문집
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    • 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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    • pp.400.1-400.1
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    • 2002
  • Because of the differences in pharmacological properties between enantiomers of chiral acidic non-steroidal antiinflammatory drugs (NSAIDs) in human body. accurate determinations of their optical purities have been in great need. An efficient capillary electrophoretic (CE) profiling method was developed for the enantioseparation of NSAIDs. Capillary electrophoretic conditions were optimized using TM$\beta$-cyclodextrin as the chiral selectors under MES buffer. (omitted)

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Liquid chromatographic enantioseparation of several amino acids as nitrobenzoxadiazole derivatives on polysaccharide trisphenylcarbamate derived chiral stationary phases

  • Suraj Adhikari;Alisha Bhandari;Wonjae Lee
    • 분석과학
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    • 제36권4호
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    • pp.143-151
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    • 2023
  • Considering the greater role of α-amino acids in our daily lives, the enantiomer resolution of seven α-amino acids derivatized with fluorogenic reagent (4-fluoro-7-nitro-2,1,3-benzoxadiazole, NBD-F) by chiral HPLC on amylose or cellulose trisphenylcarbamate derived chiral stationary phases (CSPs) under simultaneous ultraviolet (UV) and fluorescence (FL) detection was performed. The degree of enantioseparation and resolution was affected by nature and selector backbones of the CSPs as well as the kind of amino acids. Baseline enantiomer separation and resolutions were observed for the enantiomers of all analytes as NBD derivatives especially on coated type amylose tris(3,5-dimethylphenylcarbamate) derived CSPs (Chiralpak AD-H and Lux Amylose-1). The other CSPs also showed good enantioselectivity except for the CSPs (Chiralpak IB, Chiralcel OD-H and Lux Cellulose-1) having cellulose tris(3,5-dimethylphenylcarbamate) as chiral selectors. The developed analytical chiral method was applied to determine the enantiomeric purity of seven commercially available L-α-amino acids and the impurities as D-forms were found to be in the range 0.08-0.87 %, respectively. The intra- and interday accuracy and precision assays showed high accuracy and precision of the developed analytical method. This chiral HPLC method for the enantiomer resolution of amino acids using fluorescent derivatization could be useful for the determination of enantiomeric purity of pharmaceuticals and biological study for amino acid type compounds among chiral drugs.

Production of Chiral Epoxides: Epoxide Hydrolase-catalyzed Enantioselective Hydrolysis

  • Choi, Won-Jae;Choi, Cha-Yong
    • Biotechnology and Bioprocess Engineering:BBE
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    • 제10권3호
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    • pp.167-179
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    • 2005
  • Chiral epoxides are highly valuable intermediates, used for the synthesis of pharmaceutical drugs and agrochemicals. They have broad scope of market demand because of their applications. A major challenge in modern organic chemistry is to generate such compounds in high yields, with high stereo- and regio-selectivities. Epoxide hydrolases (EH) are promising biocatalysts for the preparation of chiral epoxides and vicinal diols. They exhibit high enantioselectivity for their substrates, and can be effectively used in the resolution of racemic epoxides through enantioselective hydrolysis. The selective hydrolysis of a racemic epoxide can produce both the corresponding diols and the unreacted epoxides with high enantiomeric excess (ee) value. The potential of microbial EH to produce chiral epoxides and vicinal diol has prompted researchers to explore their use in the synthesis of epoxides and diols with high ee values.

Chiral Separation of Non-Steroidal Inflammatory Drugs as Dual Diastereomeric Derivatives with (R)-and (S)-Phenylethylamines

  • Lee, Yoon-Suk;Paik, Man-Jeong;Kim, Kyoung-Rae
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.282.2-283
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    • 2003
  • The carboxylated acidic non-steroidal antiinflammatory drugs (NSAIDs) constitute the principal class of agents for controlling the pain and inflammation of the rheumatic diseases. It is mostly administered as a racemic mixture like most other drugs with asymmetric carbon atoms. However enantiomers of many racemic drug substances have been shown to posses different pharmacological toxicological properties. (omitted)

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Recent Developments in Analytical and Preparative Scale Enantioseparations

  • Chankvetadze, Bezhan
    • 대한약학회:학술대회논문집
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    • 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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    • pp.161-162
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    • 2002
  • Field of enantioseparations represents one of the actual topics of chemistry. Significant, in some cases dramatic differences in a desired activity as well as in toxic properties of enantiomers of chiral drugs, food additives, agrochemicals, cosmetic products, etc. represents a driving force in this field. The enantiomers of all chiral bioactive compounds have to be isolated and to be tested. Besides the ethical or environmental reasons for developing single enantiomers, it may be a real therapeutic benefit and in some cases, it has been used as a strategy for extending patent life. (omitted)

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Novel Asymmetric Synthesis of Unsaturated 1,2-Amino Alcohols

  • Kim, Ji-Duck;Jung, Young-Hoon
    • 대한약학회:학술대회논문집
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    • 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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    • pp.231.2-232
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    • 2002
  • The synthesis of chiral 1,2-amino alcohols has been an area of intense study in the synthetic and industrial fields, because of their important roles in organic synthesis as fundamental building blocks and their occurrence in a number of natural products. drugs. and chiral auxiliaries or ligands. General methods for the synthesis of these compounds can be divided into two large categories: functional group transformations and the C-C or the C-N bond formations. (omitted)

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