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【结 构 式】 
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【药物名称】Amtolmetin guacil, ST-679, MED-15, Eufans 【化学名称】2-[2-[1-Methyl-2-(4-methylbenzoyl)pyrrol-5-yl]acetamido]acetic acid 2-methoxyphenyl ester 【CA登记号】87344-06-7 【 分 子 式 】C24H24N2O5 【 分 子 量 】420.46928 |
【开发单位】Sigma-Tau (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antiarthritic Drugs, Non-Opioid Analgesics, Osteoarthritis, Treatment of, Rheumatoid Arthritis, Treatment of, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Non-Steroidal Antiinflammatory Drugs |
合成路线1
The condensation of 1-methyl-5-(4-methylbenzoyl)pyrrole-2-acetic acid (I) with glycine ethyl ester (II) by means of carbonyldiimidazole (CDI) and triethylamine in THF gives the corresponding acetamidoacetate (III), which is hydrolyzed with NaOH in THF-water yielding 2-[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetamido]acetic acid (IV). Finally, this compound is esterified with 2-methoxyphenol (guayacol) (V) by means of CDI in hot THF.
| 【1】 Baglioni, A. (Medosan; Sigma-Tau); Pyrroleacetic acid amides, their preparation and use. BE 0896018 . |
| 【2】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Arrigoni-Martelli, E.; ST-679. Drugs Fut 1989, 14, 10, 963. |
| 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) | 11352 | 2-[1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid | C15H15NO3 | 详情 | 详情 | |
| (II) | 10309 | ethyl 2-aminoacetate; Glycine ethyl ester | 459-73-4 | C4H9NO2 | 详情 | 详情 |
| (III) | 21363 | ethyl 2-([2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl]amino)acetate | C19H22N2O4 | 详情 | 详情 | |
| (IV) | 21364 | 2-([2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetyl]amino)acetic acid | C17H18N2O4 | 详情 | 详情 | |
| (V) | 13182 | Guaiacol; 2-Methoxyphenol | 90-05-1 | C7H8O2 | 详情 | 详情 |