Practical synthesis of a neuropeptide Y antagonist via stereoselective addition to a ketene

…, T Itoh, T Mase, SA Weissman, D Tschaen…

Index: Iida, Takehiko; Satoh, Hiroki; Maeda, Kenji; Yamamoto, Yuhei; Asakawa, Ken-Ichi; Sawada, Naotaka; Wada, Toshihiro; Kadowaki, Chie; Itoh, Takahiro; Mase, Toshiaki; Weissman, Steven A.; Tschaen, Dave; Krska, Shane; Volante Journal of Organic Chemistry, 2005 , vol. 70, # 23 p. 9222 - 9229

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Citation Number: 16

Abstract

The synthesis of neuropeptide Y antagonist 1, currently under clinical investigation for the treatment of obesity, is described. The convergent synthesis from trans-spirolactone carboxylic acid intermediate 2a and aminopyrazole 3 is predicated on a stereoselective route to the former. The coupling reaction of ethyl 4-oxocyclohexanecarboxylate (10a) with lithiated isonicotinamide 11 was investigated in detail, but even optimized conditions only ...

Discovery of trans-N-[1-(2-fluorophenyl)-3-pyrazolyl]-3-oxos...

[Haga, Yuji; Sakamoto, Toshihiro; Shibata, Takunobu; Nonoshita, Katsumasa; Ishikawa, Makoto; Suga, Takuya; Takahashi, Hirobumi; Takahashi, Toshiyuki; Takahashi, Hidekazu; Ando, Makoto; Murai, Takashi; Gomori, Akira; Oda, Zenjun; Kitazawa, Hidefumi; Mitobe, Yuko; Kanesaka, Maki; Ohe, Tomoyuki; Iwaasa, Hisashi; Ishii, Yasuyuki; Ishihara, Akane; Kanatani, Akio; Fukami, Takehiro Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 19 p. 6971 - 6982]