SK&F-89976A, -Drug Synthesis Database

【结构式】

【药物名称】SK&F-89976A

【化学名称】N-(4,4-Diphenyl-3-butenyl)nipecotic acid hydrochloride
　　　　　　4-(3-Carboxypiperidine)-1,1-diphenyl-1-butene hydrochloride
　　　　　　1-(4,4-Diphenyl-3-butenyl)-3-piperidinecarboxylic acid hydrochloride

【CA登记号】85375-15-1, 85375-85-5 (free base)

【分子式】C₂₂H₂₆ClNO₂

【分子量】371.91102

【开发单位】GlaxoSmithKline (Originator)

【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS, GABA Reuptake Inhibitors

合成路线1

The ethyl ester of 3-piperidinecarboxylic acid (nipecotic acid) (II) is N-alkylated with 4,4-diphenyl-3-butenyl bromide (I). The ethyl ester of N-(4,4-diphenyl-3-butenyl)nipecotic acid thus obtained is then hydrolyzed with HCl to yield the hydrochloride of the free acid.

参考文献中间体

【1】 Fe, A.; et al.; Orally active and potent inhibitors of gamma-aminobutyric acid uptake. J Med Chem 1985, 28, 5, 653.
【2】 Loscher, W.; SK&F-89976-A. Drugs Fut 1986, 11, 1, 36.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	24116	1-(4-bromo-1-phenyl-1-butenyl)benzene	C₁₆H₁₅Br	详情	详情
(II)	12453	ethyl (3R)hexahydro-3-pyridinecarboxylate	C₈H₁₅NO₂	详情	详情
(III)	24121	ethyl 1-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylate	C₂₄H₂₉NO₂	详情	详情

Extended Information