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【结 构 式】 
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【药物名称】D-22558 【化学名称】2-[1-(4-Fluorobenzyl)indol-3-yl]-N-(4-pyridyl)acetamide 【CA登记号】176204-36-7 【 分 子 式 】C22H18FN3O 【 分 子 量 】359.40666 |
【开发单位】Asta Medica (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antiallergy/Antiasthmatic Drugs, Asthma Therapy, Drugs for Allergic Rhinitis, Non-Opioid Analgesics, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Histamine Release Inhibitors, Mediator Release Inhibitors |
合成路线1
Indolylacetic acid (I) was esterified with ethanolic HCl, and the resulting ethyl ester (II) was alkylated with 4-fluorobenzyl chloride (III) in the presence of NaH to afford the N-fluorobenzyl indole (IV). Subsequent saponification of (IV) provided carboxylic acid (V). This was finally coupled with 4-aminopyridine (VI) by means of activation with 2-chloro-1-methylpyridinium iodide.
| 【1】 Menciu, C.; Duflos, M.; Fouchard, F.; et al.; New N-(pyridin-4-yl)-(indol-3-yl)acetamides and propanamides as antiallergic agents. J Med Chem 1999, 42, 4, 638. |
| 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) | 25657 | Indole-3-acetic acid; 2-(1H-Indol-3-yl)acetic acid; 3-Indoleacetic acid | 87-51-4 | C10H9NO2 | 详情 | 详情 |
| (II) | 25658 | 2-(1H-Indol-3-yl)acetic acid ethyl ester | 778-82-5 | C12H13NO2 | 详情 | 详情 |
| (III) | 12354 | 4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene | 352-11-4 | C7H6ClF | 详情 | 详情 |
| (IV) | 25659 | ethyl 2-[1-(4-fluorobenzyl)-1H-indol-3-yl]acetate | C19H18FNO2 | 详情 | 详情 | |
| (V) | 25660 | 2-[1-(4-fluorobenzyl)-1H-indol-3-yl]acetic acid | C17H14FNO2 | 详情 | 详情 | |
| (VI) | 25661 | 4-pyridinamine; 4-aminopyridine | 5044-74-5 | C5H6N2 | 详情 | 详情 |