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Bioorg Med Chem. 2011 Nov 1;19(21):6430-46. doi: 10.1016/j.bmc.2011.08.070. Epub 2011 Sep 5.

Design, structure-activity relationship, and highly efficient asymmetric synthesis of 3-phenyl-4-benzylaminopiperidine derivatives as novel neurokinin-1 receptor antagonists.

Author information

1
Pharmaceutical Research Division, Takeda Pharmaceutical Co. Ltd, 2-17-85, Jusohonmachi, Yodogawa-ku, Osaka 532-8686, Japan. Shirai_Junya@takeda.co.jp

Erratum in

  • Bioorg Med Chem. 2014 Apr 1;22(7):2379.

Abstract

We synthesized a series of novel 3-phenyl-4-benzylaminopiperidine derivatives that were identified as potent tachykinin NK(1) receptor antagonists by structural modification of the 3-benzhydrylpiperidone derivative through high-throughput screening. N-{2-[(3R,4S)-4-({2-Methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl}amino)-3-phenyl-1-piperidinyl]-2-oxoethyl}acetamide ((+)-39) was found to be one of the most potent tachykinin NK(1) receptor antagonists with high metabolic stability. Highly efficient asymmetric synthesis of (+)-39 was achieved via dynamic kinetic resolution.

PMID:
21944973
DOI:
10.1016/j.bmc.2011.08.070
[Indexed for MEDLINE]

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