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【结 构 式】 
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【药物名称】PD-159790 【化学名称】N-(1-Ethylpiperidin-3-yl)-N-[6-iodo-2-(trifluoromethyl)quinazolin-4-yl]amine 【CA登记号】 【 分 子 式 】C16H18F3IN4 【 分 子 量 】450.24826 |
【开发单位】Pfizer (Originator) 【药理作用】Acute Myocardial Infarction, Treatment of, Atherosclerosis Therapy, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Restenosis Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Endothelin-Converting Enzyme Inhibitors |
合成路线1
The cyclization of 2-amino-5-iodobenzoic acid (I) with an excess of refluxing trifluoroacetic anhydride (II) by means of triethylamine gives 6-iodo-2-(trifluoromethyl)-3,1-benzoxazin-4-one (III), which is treated with conc. aqueous NH4OH to afford 6-iodo-2-(trifluoromethyl)quinazolin-4(3H)-one (IV). The reaction of (IV) with refluxing POCl3 yields 4-chloro-6-iodo-2-(trifluoromethyl)quinazoline (V), which is finally condensed with 1-Ethylpiperidine-3-amine (VI) by means of triethylamine in ether.
| 【1】 Ahn, K.; Cheng, X.-M.; Doherty, A.M.; Elslager, E.F.; Kornberg, B.; Lee, C.; Leonard, D.; Nikam, S.S.; Werbel, L.M. (Pfizer Inc.); Quinazolines as inhibitors of endothelin converting enzyme. EP 0799221; JP 1998510834; US 5658902; WO 9619474 . |
| 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) | 19964 | 5-Iodoanthranilic acid; 2-amino-5-iodobenzoic acid | 5326-47-6 | C7H6INO2 | 详情 | 详情 |
| (III) | 19965 | 6-iodo-2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one | C9H3F3INO2 | 详情 | 详情 | |
| (IV) | 19966 | 6-iodo-2-(trifluoromethyl)-4(3H)-quinazolinone | C9H4F3IN2O | 详情 | 详情 | |
| (V) | 19967 | 4-chloro-6-iodo-2-(trifluoromethyl)quinazoline | C9H3ClF3IN2 | 详情 | 详情 | |
| (VI) | 19968 | 1-ethyl-3-piperidinamine; 1-ethyl-3-piperidinylamine | C7H16N2 | 详情 | 详情 |