Atiprimod hydrochloride, SK&F-106615-I2(dimaleate), SK&F-106615-A2
阿替莫德Chemical Name: 2-[3-(Diethylamino)propyl]-8,8-dipropyl-2-azaspiro[4.5]decane dihydrochloride; N,N-Diethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine dihydrochloride
CAS No. 130065-61-1, 183063-72-1 (dimaleate), 123018-47-3 (free base)
项目整合开发状态: Phase II
项目研究机构: Callisto Pharmaceuticals (Orphan Drug), AnorMED (Originator), GlaxoSmithKline (Originator), Callisto Pharmaceuticals (Licensee)
合成路线:Piperidine-catalyzed condensation of ethyl cyanoacetate with (I) (1) afforded cyanoester (II).Michael addition of KCN to (II) gave dinitrile (III),which was hydrolyzed under basic conditions to afford diacid (IV).Condensation of (IV) with N,N-diethylaminopropylamine afforded the desired imide (V).Reduction of (V) with lithium aluminum hydride gave the required diamine which was treated with aqueous HCl/n-propanol to yield the diamine as the dihydrochloride salt,SK&F 106615-A2 (VI).
📌 参考资料/链接：
参考文献标题:Immunomodulatory azaspiranes
文献作者:Badger,A.M.; Dimartino,M.J.; Mirabelli,C.K.; Cheeseman,E.N.; Dorman,J.W.; Picker,D.H.; Schwartz,D.A.(SmithKline Beecham plc)
参考来源:AU 8825333; EP 0310321; JP 1991500290; US 4963557; WO 8902889
📄 详细内容
合成路线:Piperidine-catalyzed condensation of ethyl cyanoacetate with (I) (1) afforded cyanoester (II).Michael addition of KCN to (II) gave dinitrile (III),which was hydrolyzed under basic conditions to afford diacid (IV).Condensation of (IV) with N,N-diethylaminopropylamine afforded the desired imide (V).Reduction of (V) with lithium aluminum hydride gave the required diamine which was treated with aqueous HCl/n-propanol to yield the diamine as the dihydrochloride salt,SK&F 106615-A2 (VI).
参考文献标题:SK&F-106615
文献作者:Wright,C.S.; Bagder,A.
参考来源:Drugs Fut 1995,20(9),893