Discovery of (E)-3-(3-((2-Cyano-4′-dimethylaminobiphenyl-4-ylmethyl)cyclohexanecarbonylamino)-5-fluorophenyl)acrylic Acid Methyl Ester, an Intestine-Specific, FXR Partial Agonist for the Treatment of Nonalcoholic Steatohepatitis

Journal of Medicinal Chemistry
2022.0

Abstract

A series of fexaramine analogs were synthesized and evaluated to develop an intestine-selective/specific FXR partial agonist. Introduction of both a CN substituent at the C-2 in the biphenyl ring and a fluorine at the C-5 in the aniline ring in fexaramine markedly increased FXR agonistic activity. <b>27c</b> showed 53 ± 3% maximum efficacy relative to GW4064 in an FXR agonist assay. A substantial amount of <b>27c</b> was absorbed in the intestine after oral administration in rats, and then it was rapidly metabolized to inactive carboxylic acid <b>44</b> by serum esterases. In CDAHFD-fed mice, oral administration of <b>27c</b> strongly induced multiple intestinal FXR target genes, FGF15, SHP, IBABP, and OST-α, but failed to activate SHP in the liver. <b>27c</b> significantly reduced the liver fibrogenesis area, hepatic fibrosis markers, and serum level of AST. Rational optimization of fexaramine has led to the identification of an intestine-specific FXR partial agonist <b>27c</b>.

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