|
【结 构 式】 
|
【药物名称】Eclanamine maleate, U-48753E 【化学名称】trans-N-(3,4-Dichlorophenyl)-N-[2-(dimethylamino)cyclopentyl]propanamide (Z)-2-butenedioate (1:1) 【CA登记号】71027-14-0, 71027-13-9 (free base), 67450-44-6 (free base;no stereoch.), 83094-52-4 (fumarate (1:1);no stereoch.), 67450-45-7 (u 【 分 子 式 】C20H26Cl2N2O5 【 分 子 量 】445.34662 |
【开发单位】Pfizer (Originator) 【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
The reaction of cyclopentene oxide (I) with dimethylamine (II) gives 2-(dimethylamino)cyclopentanol (III), which is treated with methanesulfonyl chloride and NaH in THF to afford the corresponding methasulfonyl ester (IV). The condensation of (IV) with 3,4-dichloroaniline (V) in THF yields N,N-dimethyl-N'-(3,4-dichlorophenyl)cyclopentane-1,2-diamine (VI), which is acylated with propionic anhydride (A) and treated finally with maleic acid (B).
| 【1】 Szmuszkovicz, J.; N-(2-Aminocyclopentyl)acylanilides and treating depression. BE 0861351; BE 0861355; US 4156015 . |
| 【2】 Szmuszkovicz, J.; Composes alcanoylanilides et leur preparation. BE 0875461 . |
| 【3】 Szmuszkovicz, J.; N-(2-aminocyclopentyl)amides. BE 0867554; DE 2817112; FR 2416882; GB 1581914; JP 54106451; NL 7803442 . |
| 【4】 Szmuszkovicz, J.; Anilide derivatives as antidepressants. US 4128663; US 4148913 . |
| 【5】 Szmuszkovicz, J.; N-(2-Aminocyclopentyl)acylanilides and treating depression. US 4156733; US 4157398 . |
| 【6】 Szmuszkovicz, J.; Kane, M.P.; von Voigtlander, P.F.; A new non-tricyclic antidepressant agent. Synthesis and activity of N-[trans-2-(dimethyamino)cyclopentyl]-N-(3,4-dichlorophenyl)propanamide and related compounds. J Med Chem 1981, 24, 10, 1230-36. |
| 【7】 Owen, R.T.; Serradell, M.N.; Castaner, J.; U-48753 E. Drugs Fut 1984, 9, 11, 846. |
| 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) | 20095 | propionic anhydride | 123-62-6 | C6H10O3 | 详情 | 详情 |
| (B) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |
| (I) | 34274 | (1R,5S)-6-oxabicyclo[3.1.0]hexane | C5H8O | 详情 | 详情 | |
| (II) | 19443 | N-methylmethanamine; N,N-dimethylamine | 124-40-3 | C2H7N | 详情 | 详情 |
| (III) | 34275 | (1S,2S)-2-(dimethylamino)cyclopentanol | C7H15NO | 详情 | 详情 | |
| (IV) | 34276 | N,N-dimethyl-N-((1S,2S)-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclopentyl)amine; (1S,2S)-N,N-dimethyl-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]cyclopentanamine | C10H21NOS | 详情 | 详情 | |
| (V) | 23629 | 3,4-dichloroaniline | 95-76-1 | C6H5Cl2N | 详情 | 详情 |
| (VI) | 34277 | N-[(1S,2S)-2-(3,4-dichloroanilino)cyclopentyl]-N,N-dimethylamine; (1S,2S)-N(1)-(3,4-dichlorophenyl)-N(2),N(2)-dimethyl-1,2-cyclopentanediamine | C13H18Cl2N2 | 详情 | 详情 |