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【结 构 式】 
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【药物名称】Efletirizine, Ucb-28754 【化学名称】2-[2-[4-[Bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid 【CA登记号】150756-35-7, 225367-66-8 (diHCl) 【 分 子 式 】C21H24F2N2O3 【 分 子 量 】390.43383 |
【开发单位】UCB (Originator) 【药理作用】Drugs for Allergic Rhinitis, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Histamine H1 Antagonists |
合成路线1
Efletirizine can be obtained by two similar ways: 1) The condensation of 1-[bis(4-fluorophenyl)methyl]piperazine (I) with 2-(2-chloroethoxy)acetamide (II) by means of Na2CO3 in hot xylene gives 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetamide (III), which is then hydrolyzed with 4N NaOH in refluxing ethanol. 2) The condensation of 1-[bis(4-fluorophenyl)methyl]piperazine (I) with 2-(2-chloroethoxy)acetic acid methyl ester (IV) by means of Na2CO3 in hot xylene gives 2-[2-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]acetic acid methyl ester amide (V), which is then hydrolyzed with 1N KOH in refluxing ethanol.
| 【1】 Graul, A.; Leeson, P.; Castañer, R.M.; Efletirizine. Drugs Fut 1997, 22, 6, 626. |
| 【2】 Baltes, E.; De Lannoy, J.; Rodriguez, L. (UCB SA); Novel 2-[4-(diphenylmethyl)-1-piperazinyl]acetic acids and their amides, process for their preparation and pharmaceutical compsns. Containing them. EP 0058146; US 4525358 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16838 | 1-Bis(4-fluorophenyl)methyl piperazine; 1-[bis(4-fluorophenyl)methyl]piperazine | 27469-60-9 | C17H18F2N2 | 详情 | 详情 |
| (II) | 16839 | 2-(2-chloroethoxy)acetamide | C4H8ClNO2 | 详情 | 详情 | |
| (III) | 16840 | 2-(2-[4-[bis(4-fluorophenyl)methyl]piperazino]ethoxy)acetamide | C21H25F2N3O2 | 详情 | 详情 | |
| (IV) | 16841 | methyl 2-(2-chloroethoxy)acetate | C5H9ClO3 | 详情 | 详情 | |
| (V) | 16842 | methyl 2-(2-[4-[bis(4-fluorophenyl)methyl]piperazino]ethoxy)acetate | C22H26F2N2O3 | 详情 | 详情 |