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【结 构 式】 
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【药物名称】Nimesulide, NIM-03, R-805, Nise Gel, Orthobid, Guaxan, Antifloxil, Nimedex, Nisulid, Nimed, Aldoron, Mesulid, Aulin 【化学名称】N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide 【CA登记号】51803-78-2 【 分 子 式 】C13H12N2O5S 【 分 子 量 】308.31499 |
【开发单位】Boehringer Ingelheim (Originator), Helsinn (Originator), LPB (Originator), Alter (Marketer), Italfarmaco (Licensee), Roche (Licensee) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Cyclooxygenase-2 Inhibitors |
合成路线1
Compound can be prepared in three different ways: 1) By nitration of 2-phenoxymethanesulfonanilide (I) with nitric acid in acetic acid. 2) By condensation of 2-phenoxy-4-nitroaniline (II) with methanesulfonyl chloride in pyridine. 3) By condensation of 2-bromo-4-nitromethanesulfonanilide (III) with phenol (A) by means of KOH and pyridine in benzene.
| 【1】 Moore, G.; Harrington, J.K.; Substituted 2-phenoxy alkanesulfonanilides. US 3840597 . |
| 【2】 2-Phenoxy alkyl sulphonalides. DE 2333643; FR 2190460; GB 1435755; JP 57136560; JP 57140712 . |
| 【3】 Castaner, J.; Chatterjee, S.S.; R-805. Drugs Fut 1976, 1, 3, 145. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 23540 | Phenol | 108-95-2 | C6H6O | 详情 | 详情 |
| (I) | 34063 | N-(2-phenoxyphenyl)methanesulfonamide; 2-Phenoxymethanesulfonanilide | 51765-51-6 | C13H13NO3S | 详情 | 详情 |
| (II) | 34064 | 4-nitro-2-phenoxyaniline; 4-nitro-2-phenoxyphenylamine | C12H10N2O3 | 详情 | 详情 | |
| (III) | 34065 | N-(2-bromo-4-nitrophenyl)methanesulfonamide | C7H7BrN2O4S | 详情 | 详情 |