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【结 构 式】 
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【药物名称】Lorglumide, CR-1409 【化学名称】D,L-4-(3,4-Dichlorobenzoylamino)-5-(di-n-pentylamino)-5-oxo-pentanoic acid 【CA登记号】97964-56-2 【 分 子 式 】C22H32Cl2N2O4 【 分 子 量 】459.41734 |
【开发单位】Rotta (Originator) 【药理作用】GASTROINTESTINAL DRUGS, Pancreatic Disorders, Treatment of, CCK1 (CCKA) Antagonists |
合成路线1
The condensation of glutamic acid (I) with 3,4-dichlorobenzoyl chloride (II) by means of Na2CO3 in water gives N-(3,4-dichlorobenzoyl)glutamic acid (III), which is treated with acetic anhydride in refluxing isopropyl ether to afford N-(3,4-dichlorobenzoyl)glutamic anhydride (IV). Finally, this compound is treated with dipentylamine (V) in water.
| 【1】 Zrenner, E.; Laties, A.M.; Eur J Med Chem - Chim Ther 1986, 21, 1, 9-20. |
| 【2】 Chiste, R.; Makovec, F.; Rovati, L.A.; Pacini, M.A.; Bani, M.; Setnikar, I.; New glutaramic acid derivatives with potent competitive and specific cholecystokinin-antagonistic activity. Arzneim-Forsch Drug Res 1985, 35, 7, 1048-1051. |
| 【3】 Rovati, L.C.; Chiste, R.; Bani, M.; Revel, L.; Makovec, F.; Rovati, L.A.; Differentiation of central and peripheral cholecystokinin receptors by new glutaramic acid derivatives with cholecystokinin-antagonistic activity. Arzneim-Forsch Drug Res 1986, 36, 1, 98-102. |
| 【4】 Rovati, L.; Makovec, F.; Senin, P.; Chiste', R. (Rotta Research Laboratorium SpA); Derivatives of glutamic acid and aspartic acid. AU 8544109; BE 0902726; CH 674203; DE 3522506; ES 8604859; FR 2566397; GB 2160869; JP 1986044855; US 4791215 . |
| 【5】 Castaner, J.; Serradell, M.N.; Castaner, R.M.; Lorglumide. Drugs Fut 1987, 12, 9, 851. |
| 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) | 28752 | DL-2-Amino propane dicarboxylic acid; DL-2-Aminopentanoic acid; glutamic acid; DL-glutamic acid; (+/-)-2-Aminoglutaric acid | 617-65-2 | C5H9NO4 | 详情 | 详情 |
| (II) | 26356 | 3,4-dichlorobenzoyl chloride | 3024-72-4 | C7H3Cl3O | 详情 | 详情 |
| (III) | 28750 | N-(3,4-dichlorobenzoyl)glutamic acid | C12H11Cl2NO5 | 详情 | 详情 | |
| (IV) | 12129 | 3,4-Dichloro-N-(2,6-dioxotetrahydro-2H-pyran-3-yl)benzamide | C12H9Cl2NO4 | 详情 | 详情 | |
| (V) | 28751 | N-pentyl-1-pentanamine | 2050-92-2 | C10H23N | 详情 | 详情 |
Extended Information