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【结 构 式】 
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【药物名称】NNC-21-0300 【化学名称】5'-Deoxy-2,5'-dichloro-N6-[4-(2-pyridylsulfanyl)piperidin-1-yl]adenosine 【CA登记号】206270-32-8 【 分 子 式 】C20H23Cl2N7O3S 【 分 子 量 】512.42141 |
【开发单位】Novo Nordisk (Originator) 【药理作用】Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, Adenosine A1 Agonists |
合成路线1
The N-amination of 4-(2-pyridylthio)piperidine (I) with hydroxylamine O-sulfonic acid afforded hydrazine (II). This was condensed with dichloropurine derivative (III) to yield the piperidinyl adenosine (IV). Deacetylation of (IV) by treatment with methanolic ammonia gave (V). Finally, the primary hydroxyl group of (V) was converted to the title chloride by reaction with SOCl2 in the presence of pyridine.
| 【1】 Knutsen, L. (Novo Nordisk A/S); Novel therapeutically active adenosine derivs.. WO 9816539 . |
| 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) | 45792 | 2-(4-piperidinylsulfanyl)pyridine; 4-piperidinyl 2-pyridinyl sulfide | C10H14N2S | 详情 | 详情 | |
| (II) | 45793 | 4-(2-pyridinylsulfanyl)-1-piperidinylamine; 4-(2-pyridinylsulfanyl)-1-piperidinamine | C10H15N3S | 详情 | 详情 | |
| (III) | 25228 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate | C16H16Cl2N4O7 | 详情 | 详情 | |
| (IV) | 45794 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-(2-chloro-6-[[4-(2-pyridinylsulfanyl)-1-piperidinyl]amino]-9H-purin-9-yl)tetrahydro-3-furanyl acetate | C26H30ClN7O7S | 详情 | 详情 | |
| (V) | 45795 | (2R,3R,4S,5R)-2-(2-chloro-6-[[4-(2-pyridinylsulfanyl)-1-piperidinyl]amino]-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C20H24ClN7O4S | 详情 | 详情 |
Extended Information