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【结 构 式】 
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【药物名称】Flestolol sulfate, ACC-9089 【化学名称】2-Fluorobenzoic acid 3-(1,1-dimethyl-2-ureidoethylamino)-2-hydroxypropyl ester sulfate (1:1) salt 【CA登记号】88844-73-9, 87721-62-8 (free base) 【 分 子 式 】C15H24FN3O8S 【 分 子 量 】425.43623 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, beta-Adrenoceptor Antagonists |
合成路线1
The condensation in DMF of 1,1-dimethyl-2-[(aminocarbonyl)amino]ethylamine (III) [prepared from 1,2-diamino-2-methylpropane (I) and urea (II)] and 2,3-epoxypropyl o-fluorobenzoate (VI) [prepared from o-fluorobenzoyl chloride (VI) and glycidol (V) in diethyl ether using triethylamine as a proton scavenger], followed by salt formation using 98% sulfuric acid in ethanol yields ACC-9089.
| 【1】 Mai, K.X.; Kam, S.T.; Matier, W.L.; O'Donnel, J.P.; Sum, C.Y.; Gorczynski, R.J.; Lee, R.J.; Stamfli, H.F.; Barcelon-Yang, C.; Anderson, W.G.; Borgman, R.J.; [(Arylcarbonyl)oxy]propanolamines. 1. Novel beta-blockers with ultrashort duration of action. J Med Chem 1984, 27, 8, 1007. |
| 【2】 Day, B.W.; Pento, J.T.; ACC-9089. Drugs Fut 1985, 10, 6, 447. |
| 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) | 29645 | 2-amino-1,1-dimethylethylamine; 2-methyl-1,2-propanediamine | 811-93-8 | C4H12N2 | 详情 | 详情 |
| (II) | 19310 | urea | 57-13-6 | CH4N2O | 详情 | 详情 |
| (III) | 29646 | N-(2-amino-2-methylpropyl)urea | C5H13N3O | 详情 | 详情 | |
| (IV) | 19551 | 2-Fluorobenzoyl chloride | 393-52-2 | C7H4ClFO | 详情 | 详情 |
| (V) | 29648 | 2-oxiranylmethanol | 556-52-5 | C3H6O2 | 详情 | 详情 |
| (VI) | 29647 | 2-oxiranylmethyl 2-fluorobenzoate | C10H9FO3 | 详情 | 详情 |