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【结 构 式】 
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【药物名称】Patamostat mesylate, E-3123 【化学名称】4-(2-Succinimidoethylthio)phenyl 4-guanidinobenzoate methanesulfonate 【CA登记号】114568-32-0, 114568-45-5 (carbonate ester (1:1)), 114568-26-2 (free base) 【 分 子 式 】C21H24N4O7S2 【 分 子 量 】508.57603 |
【开发单位】Eisai (Originator) 【药理作用】GASTROINTESTINAL DRUGS, Pancreatic Disorders, Treatment of, Trypsin Inhibitors |
合成路线1
The alkylation of succinimide (I) with 1,2-dibromoethane (II) by means of K2CO3 in refluxing butanone gives N-(2-bromoethyl)succinimide (III), which is condensed with 4-hydroxythiophenol (IV) by means of K2CO3 in refluxing ethanol to afford 4-hydroxyphenyl 2-succinimidoethyl sulfide (V). Finally, this compound is esterified with 4-guanidinobenzoyl chloride in pyridine, and treated with methanesulfonic acid in methanol.
| 【1】 Hishinuma, I.; Kawashima, H.; Kawata, T.; Miyamoto, K.; Miyazawa, S.; Nagakawa, J.; Nagaoka, J.; Nagaoka, N.; Shimomura, N.; Souda, S.; Ueda, N.; Wakabayashi, T.; Yamanaka, T. (Eisai Co., Ltd.); Guanidinobenzoic ester deriv., a process for preparing same and pharmaceutical compsns. containing same. EP 0229370; JP 1987155253; JP 1994298730; US 4801603; US 5075335 . |
| 【2】 Prous, J.; Castaner, J.; E-3123. Drugs Fut 1988, 13, 7, 613. |
| 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) | 22543 | 2,5-pyrrolidinedione | 123-56-8 | C4H5NO2 | 详情 | 详情 |
| (II) | 10252 | 1,2-Dibromoethane; Ethylene dibromide | 106-93-4 | C2H4Br2 | 详情 | 详情 |
| (III) | 22545 | 1-(2-bromoethyl)-2,5-pyrrolidinedione | C6H8BrNO2 | 详情 | 详情 | |
| (IV) | 22546 | 4-sulfanylphenol | 637-89-8 | C6H6OS | 详情 | 详情 |
| (V) | 22547 | 1-[2-[(4-hydroxyphenyl)sulfanyl]ethyl]-2,5-pyrrolidinedione | C12H13NO3S | 详情 | 详情 | |
| (VI) | 22548 | 4-[[amino(imino)methyl]amino]benzoyl chloride | C8H8ClN3O | 详情 | 详情 |