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【结 构 式】 
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【药物名称】Pelrinone hydrochloride, AY-28768 【化学名称】1,4-Dihydro-2-methyl-4-oxo-6-[(3-pyridinylmethyl)amino]-5-pyrimidinecarbonitrile monohydrochloride 【CA登记号】89232-84-8, 94386-65-9 (free base) 【 分 子 式 】C12H12ClN5O 【 分 子 量 】277.71534 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, Phosphodiesterase III Inhibitors |
合成路线1
The cyclization of acetamidine (I) with 2-cyano-3,3-bis(methylthio)-2-propenoic acid methyl ester (II) by means ot NaH in DMF gives 2-methyl-6-(methylthio)-4 oxo-1,4-dihydropyrimidine-5-carbonitrile (III), which is then condensed with 3-pyridylmethyl amine (IV) by refluxing in dimethoxyethane solution.
| 【1】 Bagli, J.F. (American Home Products Corp.); Amino-pyrimidine derivs.. EP 0130735; ES 8602694; JP 1985025974; US 4505910 . |
| 【2】 Prous, J.; Castaner, J.; Pelrinone hydrochloride. Drugs Fut 1988, 13, 8, 728. |
| 【3】 Bagli, J.; Bogri, T.; Palameta, B.; Rakhit, S.; Peseckis, S.; McQuillan, J.; Lee, D.K.; Chemistry and positive inotropic effect of pelrino. J Med Chem 1988, 31, 4, 814-23. |
| 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) | 15866 | ethanimidamide | C2H6N2 | 详情 | 详情 | |
| (II) | 22737 | methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate | C7H9NO2S2 | 详情 | 详情 | |
| (III) | 22738 | 2-methyl-6-(methylsulfanyl)-4-oxo-1,4-dihydro-5-pyrimidinecarbonitrile | C7H7N3OS | 详情 | 详情 | |
| (IV) | 18731 | 3-pyridinylmethanamine; 3-pyridinylmethylamine | 3731-52-0 | C6H8N2 | 详情 | 详情 |
Extended Information