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【结 构 式】 
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【药物名称】Gadoversetamide, Gd-DTPA-bismethoxyethylamide, MP-1177-10, OptiMARK 【化学名称】[N,N-Bis[2-[(carboxymethyl)[N-(2-methoxyethyl)carbamoylmethyl]amino]ethyl]glycinato(3-)]gadolinium 【CA登记号】131069-91-5, 129009-83-2 (ligand) 【 分 子 式 】C20H34GdN5O10 【 分 子 量 】661.77148 |
【开发单位】Mallinckrodt (Originator) 【药理作用】DIAGNOSTIC AGENTS, Magnetic Resonance Imaging Agents |
合成路线1
The reaction of diethylenetriamine-pentaacetic acid (I) with acetic anhydride in hot pyridine gives the dianhydride (II), which is treated with 2-methoxyethylamine (III) in hot acetonitrile or isopropanol to yield the diamide ligand (IV). Finally, this compound is treated with Gd2O3 in hot water/isopropanol/acetonitrile or other mixed solvents to afford the target gadolinium complex.
| 【1】 Geraldes, C.F.G.C.; et al.; Preparation, physico-chemical characterization, and relaxometry studies of various gadolinium(III)-DTPA-bis(amide) derivatives as potential magnetic resonance contrast agents. Magn Reson Imaging 1995, 13, 3, 401. |
| 【2】 White, D.H.; Moore, D.A.; deLearie, L.; Lin, W.H. (Mallinckrodt Medical Inc.); Process for manufacturing DTPA-bis amide magnetic resonance imaging. US 5508388 . |
| 【3】 Periasamy, M.P.; Weber, R.W. (Mallinckrodt Medical Inc.); Novel magnetic resonance imaging agents. WO 9001024 . |
| 【4】 Periasamy, M.; et al.; The synthesis and screening of nonionic gadolinium (III) DTPA-bisamide complexes as magnetic resonance imaging contrast agents. Invest Radiol 1991, 26, Suppl. 1, S217. |
| 【5】 White, D.H.; et al.; Synthesis and characterization of nonionic paramagnetic metal complexes as potential magnetic resonance imaging contrast agents. Invest Radiol 1990, 25, Suppl. 1, S56. |
| 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) | 55225 | 2-(bis{2-[bis(carboxymethyl)amino]ethyl}amino)acetic acid | C14H23N3O10 | 详情 | 详情 | |
| (II) | 49150 | Diethylenetriaminepentaacetic acid; N,N-Bis[2-(2,6-dioxomorpholino)ethyl]glycine | 23911-26-4 | C14H19N3O8 | 详情 | 详情 |
| (III) | 34675 | 2-methoxyethylamine; 2-methoxy-1-ethanamine | 109-85-3 | C3H9NO | 详情 | 详情 |
| (IV) | 55226 | 8,11-bis(carboxymethyl)-14-{2-[(2-methoxyethyl)amino]-2-oxoethyl}-6-oxo-2-oxa-5,8,11,14-tetraazahexadecan-16-oic acid | C20H37N5O10 | 详情 | 详情 |