HPLC enantiomer separation of a chiral 1,4-dihydropyridine monocarboxylic acid

Lämmerhofer, Michael; Gyllenhaal, Olle; Lindner, Wolfgang

doi:10.1016/s0731-7085(03)00644-7

Cited by 34 publications

(20 citation statements)

References 11 publications

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“…The optimization gave a baseline separation of all four stereoisomers of 44 and 45 in a single run [88]. Several pharmacologically active acids have also been successfully separated, including nonsteroidal anti-inflammatory profens such as naproxen 46, ibuprofen 47, flurbiprofen 48 [58,66], planar chiral acid 49 [89], quinazolone derivatives 50 [90], and monomethyl ester of 4-(2 0 ,3 0 -dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 51 -an active metabolite of the short-acting calcium antagonist clevidipine [91].…”

Section: Applicationsmentioning

confidence: 99%

Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives

Kacprzak

Gawroński

2009

Cinchona Alkaloids in Synthesis and Catalysis

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Section: Applicationsmentioning

confidence: 99%

Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives

Kacprzak

Gawroński

2009

Cinchona Alkaloids in Synthesis and Catalysis

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“…7) because of the slow mass transfer in the CSP, well known for enantioselective chromatography systems with its heterogeneous adsorption sites. 26 In the present case, an improvement of the plate counts by a factor of about 1.5 could be achieved for 5-MATIDA by reducing the eluent flow rate from 1.0 to 0.25 ml/min. For 4-CPHE enantiomers the efficiency gain was even more noteworthy, namely a factor of about 2.…”

Section: Flow Ratementioning

confidence: 56%

“…19,26 Over the pH-range investigated presently (5.0-7.0), the quinuclidine ring is protonated throughout and thus the WAX-type CSP has a reasonable anion-exchange capacity. Moreover, in this pH range also the carboxylic acid functionalities of the analytes (pK a -values of COOH groups < 4.6; pI values of the acidic amino acids range between 4.6 and 5.6) are ionized thus enabling attractive electrostatically driven selector-solute interactions.…”

Section: Effect Of Eluent Phmentioning

confidence: 99%

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Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase

et al. 2008

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A tert-butylcarbamoylquinine-based chiral stationary phase (Chiralpak QN-AX) has been employed for the enantiomer separation of underivatized chiral acidic amino acids, viz. 4-carboxyphenylalanine (4-CPHE), 1-aminoindan-1,5-dicarboxylic acid (AIDA), 2-(5-carboxy-3-methyl-2-thienyl)glycine (3-MATIDA), 2-(4-carboxy-5-methyl-2-thienyl)glycine (5-MATIDA), and 2-(2'-carboxy-3'-phenylcyclopropyl)glycine (PCCG). Some of the acidic amino acids have potential activity on the central nervous system and are thus of great interest. A stereoselective HPLC method that allows the baseline resolution of all the five test solutes has been developed. For that purpose the mobile phase composition (pH, organic modifier, and type) and flow rate were optimized. The final method makes use of mild elution conditions, namely methanol - 0.8 M ammonium acetate buffer (97.5:2.5; v/v) pH 5.5 which are also compatible with mass spectrometric detection.

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“…13 Recently, much work has been reported describing the use of chiral stationary phases, in conjugation with HPLC, as a way to separate and thereby individually quantitative the enantiomers of an enantiomeric pair. [14][15][16] The chiral nature of the drug has made the importance to develop the chiral HPLC method for the enantiomeric purity and quantitative determination of undesired isomer.…”

Section: Repaglinide (Figure 1) Single Enantiomer Is Chemically (S)-(mentioning

confidence: 99%

A validated chiral LC method for the enantiomeric separation of repaglinide on immobilized amylose based stationary phase

Patil¹,

Rane²,

Yeole³

et al. 2012

J. Braz. Chem. Soc.

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Um método de HPLC quiral em fase normal, simples, rápido, isocrático, foi desenvolvido e validado para a separação enantiomérica de repaglinida, ácido (S)-(+)-2-etóxi-4-N [1-(2-piperidinofenil)-3-metil-1-butil] aminocarbonilmetil] benzóico, uma substância antidiabética. Os enantiômeros de repaglinida foram resolvidos em uma coluna Chiralpak IA (fase estacionária a base de amilose imobilisada) usando uma fase móvel consistindo de n-hexano:etanol:ácido trifluoroacético (80:20:20, v/v/v) a uma vazão de 1,0 mL min -1 . A resolução encontrada entre os enantiômeros foi maior do que 2 no método otimizado. O método desenvolvido foi extensivamente validado e mostrou-se robusto, enantiosseletivo, exato, preciso e adequado para determinação quantitativa de (R)-enantiômero na substância a granel e no produto formulado.A simple, rapid, isocratic, normal phase chiral HPLC method was developed and validated for the enantiomeric separation of repaglinide, (S)-(+)-2-ethoxy-4-N [1-(2-piperidinophenyl)-3-methyl-1-butyl] aminocarbonylmethyl] benzoic acid, an antidiabetic drug substance. The enantiomers of repaglinide were resolved on a Chiralpak IA (immobilized amylose based stationary phase) column using a mobile phase consisting of n-hexane:ethanol:trifluoroacetic acid (80:20:0.2, v/v/v) at a flow rate of 1.0 mL min -1 . The resolution between both enantiomers was greater than 2 in the optimized method. The developed method was extensively validated and proved to be robust, enantioselective, accurate, precise, and suitable for quantitative determination of (R)-enantiomer in bulk drug substance and product.

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HPLC enantiomer separation of a chiral 1,4-dihydropyridine monocarboxylic acid

Cited by 34 publications

References 11 publications

Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives

Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives

Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase

A validated chiral LC method for the enantiomeric separation of repaglinide on immobilized amylose based stationary phase

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