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【结 构 式】 
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【药物名称】RPR-132294 【化学名称】N-(3,5-Dimethylisoxazol-4-yl)-4-methoxy-3-(tetrahydrofuran- 3-yloxy)benzamide 【CA登记号】 【 分 子 式 】C17H20N2O5 【 分 子 量 】332.35935 |
【开发单位】Rh?ne-Poulenc Rorer 【药理作用】RESPIRATORY DRUGS, ASTHMA THERAPY |
合成路线1
Coupling of isovanillin (I) with 3-hydroxytetrahyrofuran (II) in the presence of triphenyl phosphine and diisopropyl azodicarboxylate yielded the tetrahydrofuryl ether (III). Subsequent oxidation of the aldehyde using sodium chlorite and sulfamic acid gave carboxylic acid (IV), which was further converted to acid chloride (V) upon treatment with SOCl2 in toluene. Finally, condensation of (V) with 4-amino-3,5-dimethylisoxazole (VI) provided the title compound.
| 【1】 Tober, C.; Rundfeldt, C.; Rostock, A.; Bartsch, R.; Nickel, B.; Szeleny, I.; Herbst, M.; Dieter, R.; Olbrich, A.; Kutscher, B.; Sauer, W.; Jainta, H.; Jahn, W.; Engel, J.; D-23129. Drugs Fut 1995, 20, 11, 1112. |
| 【2】 Fenton, G.; Palfreyman, M.N.; Thurairatnam, S. (Aventis Pharma SA); Substd. aromatic cpds. as cAMP phosphodiesterase- and TNF-inhibitors. EP 0741707; JP 1997509654; WO 9520578 . |
| 【3】 Dieter, H.-R.; Engel, J.; Kutscher, B.; Polymeropoulos, E.; Szelenyi, S.; Nickel, B. (Asta Medica AG); Novel 1,2,4-Triaminobenzene derivs. and process for their preparation. DE 4200259; EP 0554543; JP 1993345752; US 5384330 . |
| 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) | 18455 | 3-hydroxy-4-methoxybenzaldehyde; Isovanillin | 621-59-0 | C8H8O3 | 详情 | 详情 |
| (II) | 20619 | tetrahydro-3-furanol | 453-20-3 | C4H8O2 | 详情 | 详情 |
| (III) | 20620 | 4-methoxy-3-(tetrahydro-3-furanyloxy)benzaldehyde | C12H14O4 | 详情 | 详情 | |
| (IV) | 20621 | 4-methoxy-3-(tetrahydro-3-furanyloxy)benzoic acid | C12H14O5 | 详情 | 详情 | |
| (V) | 20622 | 4-methoxy-3-(tetrahydro-3-furanyloxy)benzoyl chloride | C12H13ClO4 | 详情 | 详情 | |
| (VI) | 20623 | 3,5-dimethyl-4-isoxazolamine; 3,5-dimethyl-4-isoxazolylamine | C5H8N2O | 详情 | 详情 |
Extended Information