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【结 构 式】 
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【药物名称】PNU-177553 【化学名称】N-[3-[3-Fluoro-4-(1-oxidothiomorpholin-4-yl)phenyl]-2-oxooxazolidin-5(S)-ylmethyl]thioacetamide 【CA登记号】216868-86-9 【 分 子 式 】C16H20FN3O3S2 【 分 子 量 】385.4825 |
【开发单位】Pfizer (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Oxazolidinones |
合成路线1
The known thiomorpholine derivative (I) was oxidized to the corresponding sulfoxide (II) employing either sodium metaperiodate or osmium tetroxide in the presence of N-methylmorpholine-N-oxide. Sulfonylation of the primary hydroxyl group of (II) with 3-nitrobenzenesulfonyl chloride and Et3N gave rise to the nosylate (IV), which was then displaced with ammonium hydroxide to furnish amine (IV). This was finally condensed with ethyl dithioacetate to produce the target thioacetamide.
| 【1】 Hester, J.B. Jr.; Perricone, S.C.; Nidy, E.G.; Poel, T.-J. (Pharmacia Corp.); Oxazolidinone antibacterial agents having a thiocarbonyl functionality. EP 0984947; JP 2002501530; US 6218413; WO 9854161 . |
| 【2】 Hester, J.B. Jr.; Perricone, S.C.; Nidy, E.G.; Poel, T.-J. (Pharmacia Corp.); Oxazolidinone antibacterial agents having a thiocarbonyl functionality. EP 1133493; JP 2002531455; WO 0032599 . |
| 【3】 Mesfin, G.-M.; Jensen, R.K. (Pharmacia Corp.); Use of thioamide oxazolidinones for the treatment of bone resorption and osteoporosis. WO 0180841 . |
| 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) | 56305 | (5R)-3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one | C14H17FN2O3S | 详情 | 详情 | |
| (II) | 56306 | 4-{2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-1lambda~4~,4-thiazinan-1-one | C14H17FN2O4S | 详情 | 详情 | |
| (III) | 56307 | {(5R)-3-[3-fluoro-4-(1-oxo-1lambda~4~,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl 3-nitrobenzenesulfonate | C20H20FN3O8S2 | 详情 | 详情 | |
| (IV) | 56308 | 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}-1lambda~4~,4-thiazinan-1-one | C14H18FN3O3S | 详情 | 详情 |