发明名称 3-PIPERIDONE COMPOUNDS AND THEIR USE AS NEUROKININ-1 (NK1) RECEPTOR ANTAGONISTS
摘要 The invention relates to 3-piperidone compounds, and in particular, to (2S)-phenyl-3-piperidone and its synthesis method. Use of the thus-synthesized 3-piperidone compounds as potent neurokinin-1 (NK1) receptor antagonists is also provided.
申请公布号 US2016031817(A1) 申请公布日期 2016.02.04
申请号 US201414777392 申请日期 2014.03.17
申请人 NANYANG TECHNOLOGICAL UNIVERSITY 发明人 Loh Teck Peng;Wang Peng;Huang Jingmei;Koh Peng Fei Jackson
分类号 C07D211/96;C07D211/02 主分类号 C07D211/96
代理机构 代理人
主权项 1. Method for synthesizing a compound of Formula (II)wherein R1 is a nitrogen-protecting group derivable from an amino group selected from the group consisting of tosylamide (Ts), t-butyl carbamate (Boc), benzyl carbamate (Cbz), 9-fluorenylmethyl carbamate (Fmoc), acetamide (Ac), trifluoroacetamide (TFA), benzylideneamine, triphenylmethylamine (Tritylamine), benzylamine (Bn), and phthalimide; R2 is selected from the group consisting of halogen, —C(O)—R, —NRR′, —OR, —SR, —COOR, —CN, —NO2, —C(O)—NRR′, —NR′—C(O)—R, —SO2—R, —(SO2)—OR, linear or branched, substituted or unsubstituted C1-C10 alkyl; linear or branched, substituted or unsubstituted C2-C10 alkenyl; linear or branched, substituted or unsubstituted C2-C10 alkynyl; linear or branched, substituted or unsubstituted C1-C10 alkoxy; substituted or unsubstituted C3-C10 cycloalkyl; substituted or unsubstituted C3-C10 cycloalkenyl; substituted or unsubstituted C6-C10 aryl; substituted or unsubstituted C3-C10 heteroaryl; R and R′ are independently selected from the group consisting of H and linear or branched, substituted or unsubstituted C1-C10 alkyl;the method comprising: reacting a compound of Formula (I) with NH2R1 to form a compound of Formula (IV) reacting the compound of Formula (IV) with a precursor of R2 in the presence of a rhodium catalyst to form an enantiomer of a compound of Formula (V) reacting the compound of Formula (V) with an oxidizing agent to form a compound of Formula (VI) reacting the compound of Formula (VI) with a reducing agent to form a compound of Formula (VII) hydrogenating the compound of Formula (VII) to form the compound of Formula (II).
地址 Singapore SG