TER-930180
Chemical Name: 3-[4-[1-(4-Chlorophenylsulfonamidomethyl)-4-(3-pyridyl)butyl]phenyl]propionic acid
CAS No. 172283-12-4
项目整合开发状态: Preclinical
项目研究机构: Terumo (Originator)
合成路线:As shown in Scheme 22341901a,TER-930180 was prepared from 3-(3-pyridyl)acrolein (I) and methyl 4-(cyanomethyl)cinnamate (II).The condensation of (I) and (II) with sodium methoxide yielded a mixture of diene isomers (III),which was then hydrogenated over Pd/C in dioxane,and then over Raney Nickel at 10 approx.15 atm of H2 in ammoniac/methanol.The amine thus obtained (IV) was treated with 4-chlorobenzenesulfonyl chloride,followed by hydrolyzation with sodium hydroxide solution,yielding TER-930180.The starting materials (I) and (II) were obtained as follows: Reduction of methyl 3-(3-pyridyl)acrylate with DIBAL,and oxidation with manganese dioxide to yield 3-(3-pyridyl)acrolein (I).Bromination of methyl 4-methylcinnamate with NBS,and cyanization with potassium cyanide in the presence of PTC produced methyl 4-cyanomethylcinnamate (II).
📌 参考资料/链接：
参考文献标题:N-(3-Pyridylalkyl)sulfonamide deriv.and pharmaceutical preparation containing thereof
文献作者:Ohnishi,H.; Miyakoshi,M.; Isozaki,M.; Fujitake,M.; Mikami,N.; Yanoshita,R.; Akasofu,H.; Sugizaki,K.; Nakata,N.(Terumo Corp.)
参考来源:EP 0501876; JP 1992270265; JP 1993043546; JP 1993043547; US 5374641
📄 详细内容
合成路线:As shown in Scheme 22341901a,TER-930180 was prepared from 3-(3-pyridyl)acrolein (I) and methyl 4-(cyanomethyl)cinnamate (II).The condensation of (I) and (II) with sodium methoxide yielded a mixture of diene isomers (III),which was then hydrogenated over Pd/C in dioxane,and then over Raney Nickel at 10 approx.15 atm of H2 in ammoniac/methanol.The amine thus obtained (IV) was treated with 4-chlorobenzenesulfonyl chloride,followed by hydrolyzation with sodium hydroxide solution,yielding TER-930180.The starting materials (I) and (II) were obtained as follows: Reduction of methyl 3-(3-pyridyl)acrylate with DIBAL,and oxidation with manganese dioxide to yield 3-(3-pyridyl)acrolein (I).Bromination of methyl 4-methylcinnamate with NBS,and cyanization with potassium cyanide in the presence of PTC produced methyl 4-cyanomethylcinnamate (II).
参考文献标题:TER-930180
文献作者:Kasukawa,H.; Ohnishi,H.
参考来源:Drugs Fut 1996,21(1),33