Deramciclane fumarate, EGIS-3886, EGYT-3886, -Drug Synthesis Database

【结构式】

【药物名称】Deramciclane fumarate, EGIS-3886, EGYT-3886

【化学名称】(1R,2S,4R)-(-)-N,N-Dimethyl-2-[(1,7,7-trimethyl-2-phenylbicyclo[2.2.1]hept-2-yl)oxy]ethanamine 2(E)-butenedioate (1:1)
　　　　　　(1R,2S,4R)-(-)-2-(Dimethylaminoethoxy)-2-phenyl-1,7,7-trimethylbicyclo[2.2.1]heptane 2(E)-butenedioate (1:1)
　　　　　　N,N-Dimethyl-2-[[(1R,2S,4R)-2-phenyl-2-bornyl]oxy]ethylamine monofumarate

【CA登记号】120444-74-8, 80178-61-6 (exo-phenyl isomer), 120444-71-5 (free base)

【分子式】C₂₄H₃₅NO₅

【分子量】417.55025

【开发单位】Egis (Originator), Orion Corp. (Licensee), Pfizer (Codevelopment)

【药理作用】Anxiolytics, Generalized Anxiety Disorder (GAD), Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT2A Antagonists, 5-HT2C (5-HT1C) Antagonists, GABA Reuptake Inhibitors

合成路线1

Grignard addition of phenylmagnesium bromide to (+)-camphor (I) yielded the endo-alcohol (II), which was reacted with 1-dimethylamino-2-chloroethane (III) to give the base corresponding to EGYT-3886. EGYT-3886 is the 2-(E)-butenedioate salt (1:1).

参考文献中间体

【1】 Budai, Z.; Magdanyi, L.; Lay, A.; Mezei, T.; Grasser, K.; Petocz, L.; Kosoczky, I. (Egis Pharmaceuticals Ltd.); Basic ethers and pharmaceutical compsns. containing the same. US 4342762 .
【2】 Berényi, E.; Baskó, G.; Fekete, M.; Nógrádi, M.; EGYT-3886. Drugs Fut 1990, 15, 12, 1174.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	17616	bromo(phenyl)magnesium; Phenyl Magnesium Bromide	100-58-3	C₆H₅BrMg	详情	详情
(I)	28296	1-[4-(difluoromethoxy)phenyl]-2-phenyl-1-ethanone		C₁₅H₁₂F₂O₂	详情	详情
(II)	31225	1,7,7-trimethyl-2-phenylbicyclo[2.2.1]heptan-2-ol		C₁₆H₂₂O	详情	详情
(III)	11907	Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine	107-99-3	C₄H₁₀ClN	详情	详情

Extended Information