YM-193489
Chemical Name: N-(1,3-Benzodioxol-5-yl)-3-[3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl)piperidin-1-yl]propionamide
CAS No. 312738-02-6 ((R)-isomer, anhydrous D-tartrate), 312738-08-2 ((S)-isomer, fumarate salt (1:1)), 312738-48-0 ((S)-isomer, fumarate salt (1:1)), 312737-98-7 (hydrochloride)
项目整合开发状态: Preclinical
项目研究机构: Yamanouchi (Originator)
合成路线:Acylation of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (I) with N-Boc-nipecotic acid (II) by means of EDC/HOBt gives amide (III).Subsequent acidic cleavage of the Boc protecting group yields amine (IV).3,4-Methylenedioxyaniline (V) is acylated by acryloyl chloride in the presence of Et3N to produce the acrylanilide (VI).Then,Michael addition of piperidine (IV) to the acrylanilide (VI) in boiling toluene provides the title compound.
📌 参考资料/链接：
参考文献标题:Novel isoquinoline derivs.or salts thereof
文献作者:Okazaki,T.; Watanabe,T.; Wada,K.; Kakefuda,A.; Masuda,N.(Yamanouchi Pharmaceutical Co.,Ltd.)
参考来源:EP 1186601; WO 0075133
📄 详细内容
合成路线:Acylation of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (I) with N-Boc-nipecotic acid (II) by means of EDC/HOBt gives amide (III).Subsequent acidic cleavage of the Boc protecting group yields amine (IV).3,4-Methylenedioxyaniline (V) is acylated by acryloyl chloride in the presence of Et3N to produce the acrylanilide (VI).Then,Michael addition of piperidine (IV) to the acrylanilide (VI) in boiling toluene provides the title compound.
参考文献标题:Structure-activity relationships of novel 1,2,3,4-tetrahydroisoquinolin derivatives as bradycardic agents
文献作者:Kakefuda,A.; Okazaki,T.; Watanabe,T.; et al.
参考来源:Drugs Fut 2002,27(Suppl.A),