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【结 构 式】 
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【药物名称】FPL-66096(formerly), ARL-66096, AR-C66096 【化学名称】5'-O-[[[Difluoro(phosphono)methyl](hydroxy)phosphoryloxy](hydroxy)phosphoryl]-2-(propylsulfanyl)adenosine 【CA登记号】145783-24-0, 145782-74-7 (tetrasodium salt) 【 分 子 式 】C14H22F2N5O12P3S 【 分 子 量 】615.33994 |
【开发单位】AstraZeneca Charnwood (Originator) 【药理作用】Antiplatelet Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, PHARMACOLOGICAL TOOLS, P2Y12 (P2T) Antagonists |
合成路线1
Alkylation of adenosine-2-thione (I) with iodopropane produced the propylthioether (II). Subsequent treatment with phosphoryl chloride in triethyl phosphate, followed by aqueous work-up afforded (propylthio)adenylic acid (III). Then, after activation with carbonyldiimidazole, the condensation of (III) with difluoromethylenebisphosphonic acid (IV) generated the target anhydride.
| 【1】 Ingall, A.H.; Cage, P.A. (Celltech Medeva plc); ATP analogues. EP 0508687; US 5654285 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 28758 | 1-iodopropane | 107-08-4 | C3H7I | 详情 | 详情 | |
| (I) | 28113 | 6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3,9-dihydro-2H-purine-2-thione | C10H13N5O4S | 详情 | 详情 | |
| (II) | 22302 | (2R,3R,4S,5R)-2-[6-amino-2-(propylsulfanyl)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C13H19N5O4S | 详情 | 详情 | |
| (III) | 22303 | [(2R,3S,4R,5R)-5-[6-amino-2-(propylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxytetrahydro-2-furanyl]methyl dihydrogen phosphate | C13H20N5O7PS | 详情 | 详情 | |
| (IV) | 28114 | difluoro(phosphono)methylphosphonic acid | CH4F2O6P2 | 详情 | 详情 |