Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Regular Articles
Optically Active Antifungal Azoles. XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone
Takashi ICHIKAWA, Tomoyuki KITAZAKI, Yoshihiro MATSUSHITA, Masami YAMADA, Ryogo HAYASHI, Masashi YAMAGUCHI, Yutaka KIYOTA, Kenji OKONOGI, Katsumi ITOH
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Keywords: water-soluble prodrug, triazolium salt, antifungal azole, TAK-457, TAK-456, 1,2,3-trisubstituted-2-butanol
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2001 Volume 49 Issue 9 Pages 1102-1109

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Abstract

1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazolium salts 2 were designed as water-soluble prodrugs. Among the prodrugs prepared, 4-acetoxymethyl-1-[(2R, 3R)-2-(2, 4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1-terazolyl)phenyl]-1-imidazolidinyl]butyl]-1H-1, 2, 4-triazolium chloride (2a: TAK-457) was selected as an injectable candidate for clinical trials based on the results of evaluations on solubility, stability, hemolytic effect and in vivo antifungal activities.

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© 2001 The Pharmaceutical Society of Japan
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