Design and syntheses of colon-specific pro-antedrugs for oral treatment of ulcerative colitis

Yukiko Fujiwara, Yasuyuki Matsuda, Katsito Unna, Toshio Suzuki, Yuji Kurosaki, Taiji Nakayama, Toshikiro Kimura

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Abstract

Design and syntlieses of colon-specific pro-ante-drugs for oral treatment of ulcerative colitis Both hydrophilic steroid derivatives, methyl 20-α-glucopyranosyloxy predniso louâtes (9 and 10) and methyl prednisolonate 20-sodium sulfates(11 and 12) were synthesised from prednisolone via methyl 20(S/R)-dihydroprednisolonates(l and 2) based on a new colon-specific drug-delivery system. Optimal conditions for the syntheses of each isomers (1) and (2) were found by the extensive studies on the reaction rates from prednisolone under various concentrations of cupric acetate in dry methanol. Their configurations at C20 in (1) and (2) were determined by their formation mechanism and 1HNMR spectroscopic studies of the corresponding acetates (3) and (4).

Original languageEnglish
Pages (from-to)365-374
Number of pages10
JournalDrug Delivery System
Volume6
Issue number5
DOIs
Publication statusPublished - 1991

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Keywords

  • 20-α-glucopyranosyloxy prednisolonate
  • methyl prednisolonate 20-sodium sulfate
  • metyl 20-dihydroprednisolonate
  • pro-antedrug
  • ulcerative colitis

ASJC Scopus subject areas

  • Pharmaceutical Science

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