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  • Title: [On the chemistry of etofenamate, a novel anti-inflammatory agent from the series of N-arylanthranilic acid derivatives (author's transl)].
    Author: Boltze KH, Kreisfeld H.
    Journal: Arzneimittelforschung; 1977; 27(6B):1300-12. PubMed ID: 579118.
    Abstract:
    Etofenamate is 2-(2-hydroxyethoxy)ethyl-N-(a,a,a,-trifluorom-tolyl)anthranilate and has been selected as an antiphlogistic agent for percutaneous therapy. Its characteristic alcohol-ether-ester structure brings about an increase in lipophilia and in its ability to penetrate through the intact skin. Furthermore, its oily consistency renders it ideal for pharmaceutical formulation in gels. The physico-chemical material constants, partition coefficients (RM values) as a measure for lipophilia, spectra and molecular models of etofenamate are described. Various methods of synthesis of etofenamate and of its intermediates are described. Structural identification is made of by-products simultaneously obtained in the reaction. Pure etofenamate is obtained through repeated molecular distillation. The synthesis is carried out uniformly with protected reaction components and, after splitting off the protective groups, extremely pure etofenamate is obtained.
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