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【结 构 式】 
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【药物名称】Fipamezole hydrochloride, JP-1730 【化学名称】4-(2-Ethyl-5-fluoroindan-2-yl)-1H-imidazole hydrochloride 【CA登记号】150586-72-4, 150586-58-6 (free base) 【 分 子 式 】C14H16ClFN2 【 分 子 量 】266.74842 |
【开发单位】Orion Corp. (Originator), Juvantia (Licensee) 【药理作用】Antiparkinsonian Drugs, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS, alpha2-Adrenoceptor Antagonists |
合成路线1
The previously reported indanyl imidazole (I) was nitrated by means of urea nitrate in sulfuric acid to afford (II). Reduction of the nitro group of (II) to the corresponding aniline (III) was carried out by catalytic hydrogenation over PtO2. Diazotization of (III) with sodium nitrite and fluoroboric acid gave rise to the diazonium fluoroborate (IV), which was then subjected to thermal decomposition to generate the title fluoro derivative.
| 【1】 Sorbera, L.A.; Castaner, J.; Bayes, M.; Fipamezole Hydrochloride. Drugs Fut 2003, 28, 1, 14. |
| 【2】 Karjalainen, A.J.; Virtanen, R.E.; Karjalainen, A.L.; Eloranta, M.M.; Salonen, J.S.; Sipilä, H.T.; Haapalinna, A.S. (Orion Corporation); Substd. imidazole derivs. and their preparation and use. EP 0618906; JP 1995506087; US 5498623; WO 9313074 . |
| 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) | 51582 | 4-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole | C14H16N2 | 详情 | 详情 | |
| (II) | 51583 | 4-(2-ethyl-5-nitro-2,3-dihydro-1H-inden-2-yl)-1H-imidazole | C14H15N3O2 | 详情 | 详情 | |
| (III) | 51584 | 2-ethyl-2-(1H-imidazol-4-yl)-2,3-dihydro-1H-inden-5-ylamine; 2-ethyl-2-(1H-imidazol-4-yl)-5-indanamine | C14H17N3 | 详情 | 详情 | |
| (IV) | 51585 | C14H15BF4N4 | 详情 | 详情 | ||
| (V) | 51586 | 4-Methylimidazole; 4-Methyl-1H-imidazole; 4-Methyl Imidazole | 822-36-6 | C4H6N2 | 详情 | 详情 |