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【结 构 式】 
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【药物名称】Y-27152 【化学名称】(+)-(3S,4R)-trans-4-(N-Acetyl-N-benzyloxyamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile 【CA登记号】127408-30-4, 127408-32-6 ((-)-enantiomer) 【 分 子 式 】C21H22N2O4 【 分 子 量 】366.42049 |
【开发单位】Mitsubishi Pharma (Originator), Japan Tobacco (Licensee) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Potassium Channel Activators |
合成路线1
This compound is prepared as follows: Optical active (-)-epoxide (I) is reacted with O-benzylhydroxylamine (II) to give (+)-trans-4-benzyloxyamino-3-ol (III), which, without further purification, is converted with acetyl chloride/pyridine into the final product, Y-27152.
| 【1】 Yamanaka, T.; Seki, T.; Nakajima, T.; Yaoka, O. (Welfide Corporation); Benzopyran compound and its pharmaceutical use. EP 0339562; JP 1990223574; US 5021432; US 5143936 . |
| 【2】 Yamanaka, T.; Nakajima, T.; Y-27152. Drugs Fut 1992, 17, 11, 999. |
| 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) | 14639 | (1aS,7bS)-2,2-dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile | C12H11NO2 | 详情 | 详情 | |
| (II) | 14640 | O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene | 622-33-3 | C7H9NO | 详情 | 详情 |
| (III) | 14641 | (3S,4R)-4-[(benzyloxy)amino]-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbonitrile | C19H20N2O3 | 详情 | 详情 |