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Synlett 2001; 2001(2): 0299-0301
DOI: 10.1055/s-2001-10786
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Improved Synthesis of a New Nonpeptidic Inhibitor of Human Neutrophil Elastase

Kazuyuki Ohmoto* , Tetsuya Yamamoto, Toshihide Horiuchi, Tsutomu Kojima, Katsutoshi Hachiya, Shinsuke Hashimoto, Masanori Kawamura, Hisao Nakai, Masaaki Toda
  • *Minase Research Institute, Ono Pharmaceutical Co., Ltd., Shimamoto, Mishima, Osaka 618-8585, Japan; Tel. +81-75-961-1151; Fax +81-75-962-9314; E-mail: hi.nakai§ono.co.jp
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Publication Date:
31 December 2001 (online)

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A practical method for the synthesis of ONO-6818 {2-(5-Amino-6-oxo-2-phenylhydropyrimidinyl)-N-[2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(methylethyl)-2-oxoethyl]acetamide} (1), the first clinical candidate for a nonpeptidic orally active inhibitor of human neutrophil elastase (HNE), was developed. This method includes a Lossen rearrangement instead of an explosive Curtius rearrangement and the improved preparation of the α-aminoketone.

enzyme inhibitor - aminopyrimidinone - ketooxadiazole - Lossen rearrangement - anionic addition reaction

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