Synthesis of Repaglinide Congeners

被引:3
|
作者
Sundaram, Dhanraj T. S. S. [1 ,2 ]
Mitra, Jayati [1 ]
Rajesh, C. [1 ]
Islam, Aminul [1 ]
Prabahar, Koilpillai Joseph [1 ]
Rao, Battula Venkateswara [2 ]
Douglas, Sanasi Paul [2 ]
机构
[1] Aurobindo Pharma Ltd, APL Res Ctr 2, Chem Res & Dev, Indrakaran V 502329, Andhra Pradesh, India
[2] Andhra Univ, Coll Engn A, Dept Chem Engn, Visakhapatnam, Andhra Pradesh, India
关键词
Benzyl repaglinide; hypoglycemic agent; impurity; N-acetyl-L-glutamic acid; repaglinide isomer; ACID;
D O I
10.1080/00397911.2015.1064139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This report describes a synthesis of two potent impurities of repaglinide, benzyl repaglinide 1 and repaglinide isomer 2, from commercially available raw materials: 2-fluoro benzonitrile, (S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butylamine (5), and 3-ethoxy-[4-(ethoxycarbonyl)phenyl]acetic acid (7). These impurities are the crucial components in determining the quality of the drug substance, repaglinide, during its manufacturing.
引用
收藏
页码:2092 / 2098
页数:7
相关论文
共 50 条
  • [41] Synthesis and Characterization of Mesoporous Silica Nanoparticles Loaded with Repaglinide for Dissolution Enhancement
    Patil, M. P.
    More, M. K.
    Chhajed, S. S.
    Bhambere, D. S.
    Kshirsagar, S. J.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2020, 82 (04) : 686 - 691
  • [42] Synthesis and evaluation of hexitol nucleoside congeners as ambiguous nucleosides
    Lambertucci, Catia
    Schepers, Guy
    Cristalli, Gloria
    Herdewijn, Piet
    Van Aerschot, Arthur
    TETRAHEDRON LETTERS, 2007, 48 (12) : 2143 - 2145
  • [43] Synthesis and biological activity of optimized belactosin C congeners
    Korotkov, Vadim S.
    Ludwig, Antje
    Larionov, Oleg V.
    Lygin, Alexander V.
    Groll, Michael
    de Meijere, Armin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) : 7791 - 7798
  • [44] Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
    Aly, Mohamed Ramadan El Sayed
    Saad, Hosam Ali
    Abdel-Hafez, Shams Hashim
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1922 - 1932
  • [45] SYNTHESIS OF WEBERINE AND NORWEBERINE AND THEIR 1-METHYL CONGENERS
    TAKAHASHI, K
    BROSSI, A
    HETEROCYCLES, 1982, 19 (04) : 691 - 695
  • [46] Total Synthesis of Reported Structure of Baulamycin A and Its Congeners
    Guchhait, Sandip
    Chatterjee, Shamba
    Ampapathi, Ravi Sankar
    Goswami, Rajib Kumar
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05): : 2414 - 2435
  • [47] A STEREOSPECIFIC ROUTE TO AZIRIDINOMITOSANES - THE SYNTHESIS OF NOVEL MITOMYCIN CONGENERS
    DANISHEFSKY, S
    BERMAN, EM
    CIUFOLINI, M
    ETHEREDGE, SJ
    SEGMULLER, BE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3891 - 3898
  • [48] Synthesis and in-vitro anticancer evaluation of bistacrine congeners
    Hu, MK
    JOURNAL OF PHARMACY AND PHARMACOLOGY, 2001, 53 (01) : 83 - 88
  • [49] SYNTHESIS OF FLUORESCENT MURAMYL DIPEPTIDE CONGENERS .2.
    HIEBERT, CK
    KOPP, WC
    RICHERSON, HB
    BARFKNECHT, CF
    JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) : 2022 - 2024
  • [50] Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners
    Ken Mukai
    Danilo Pereira de Sant'Ana
    Yasuo Hirooka
    Eduardo V. Mercado-Marin
    David E. Stephens
    Kevin G. M. Kou
    Sven C. Richter
    Naomi Kelley
    Richmond Sarpong
    Nature Chemistry, 2018, 10 (1) : 38 - 44