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【结 构 式】 
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【药物名称】Dexloxiglumide, CR-2017 【化学名称】(R)-4-(3,4-Dichlorobenzamido)-5-[N-(3-methoxypropyl)-N-pentylamino]-5-oxopentanoic acid 【CA登记号】119817-90-2 【 分 子 式 】C21H30Cl2N2O5 【 分 子 量 】461.38965 |
【开发单位】Rotta (Originator), Forest (Licensee) 【药理作用】Constipation, Agents for, Esophageal Diseases, Treatment of, Gastroesophageal Reflux Disease, Agents for, GASTROINTESTINAL DRUGS, Irritable Bowel Syndrome, Agents for, CCK1 (CCKA) Antagonists |
合成路线1
The condensation of the N-(benzyloxycarbonyl)-D-glutamic acid 5-benzyl ester (I) with N-(3-methoxypropyl)-N-pentylamine (II) by means of ethyl chloroformate and triethylamine in THF gives the corresponding amide (III), which is debenzylated by hydrogenation over Pd/C in methanol, yielding compound (IV). Finally, the free amino group of (IV) is acylated with 3,4-dichlorobenzoyl chloride (V) by means of NaOH in water to give dexloxiglumide.
| 【1】 Castaner, J.; Revel, L.; Makovec, F.; Dexloxiglumide. Drugs Fut 1999, 24, 7, 725. |
| 【2】 Makovec, F.; Chiste, R.; Peris, W.; Rovati, L. (Rotta Research Laboratorium SpA); Derivs. of (R)-5-pentylamino-5-oxopentanoic acid with anticholecystokinin activity. EP 0344184; JP 1988201156; US 5130474; US 5391574; WO 8805774 . |
| 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) | 26353 | (2R)-5-(benzyloxy)-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid | 5680-86-4 | C20H21NO6 | 详情 | 详情 |
| (II) | 12130 | N-(3-Methoxypropyl)-N-pentylamine; N-(3-Methoxypropyl)-1-pentanamine | C9H21NO | 详情 | 详情 | |
| (III) | 26354 | benzyl (4R)-4-[[(benzyloxy)carbonyl]amino]-5-[(3-methoxypropyl)(pentyl)amino]-5-oxopentanoate | C29H40N2O6 | 详情 | 详情 | |
| (IV) | 26355 | benzyl (4R)-4-amino-5-[(3-methoxypropyl)(pentyl)amino]-5-oxopentanoate | C21H34N2O4 | 详情 | 详情 | |
| (V) | 26356 | 3,4-dichlorobenzoyl chloride | 3024-72-4 | C7H3Cl3O | 详情 | 详情 |