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【结 构 式】 
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【药物名称】Rec-2615, Rec-15/2615 【化学名称】1-[4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-2-[2-(isopropyl)-6-methoxyphenoxy]ethan-1-one hydrochloride 【CA登记号】173059-17-1, 173059-47-7 (free base) 【 分 子 式 】C26H34ClN5O5 【 分 子 量 】532.04438 |
【开发单位】Recordati (Originator) 【药理作用】Disorders of Sexual Function and Reproduction, Treatment of, ENDOCRINE DRUGS, RENAL-UROLOGIC DRUGS, Treatment of Erectile Dysfunction, Treatment of Female Sexual Dysfunction, Treatment of Male Sexual Dysfunction, alpha1B-Adrenoceptor Antagonists |
合成路线1
The alkylation of 2-isopropyl-6-methoxyphenol (I) with ethyl bromoacetate (II) under phase-transfer conditions in the presence of NaOH provided (aryloxy)acetic acid (III) which, upon treatment with SOCl2, was converted into acid chloride (IV). Coupling of (IV) with 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline (V) then furnished the target amide. The title compound was finally isolated as the hydrochloride salt.
| 【1】 Leonardi, A.; Motta, G.; Boi, C.; Testa, R. (Recordati Industria Chimica e Farmaceutica SpA); Quinazolinyl-amino derivs. having alpha-antagonist activity. EP 0750614; JP 1997511238; US 5798362; WO 9525726 . |
| 【2】 Leonardi, A.; Motta, G.; Boi, C.; Testa, R.; Poggesi, E.; De Benedetti, P.G.; Menziani, M.C.; Synthesis, pharmacological evaluation, and structure-activity relationship and quantitative structure-activity relationship studies on novel derivatives of 2,4-diamino-6,7-dimethoxyquinazoline alpha1-adrenoceptor antagonists. J Med Chem 2000, 42, 3, 427. |
| 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) | 40765 | 2-isopropyl-6-methoxyphenol | C10H14O2 | 详情 | 详情 | |
| (II) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (III) | 40766 | 2-(2-isopropyl-6-methoxyphenoxy)acetic acid | C12H16O4 | 详情 | 详情 | |
| (IV) | 40767 | 2-(2-isopropyl-6-methoxyphenoxy)acetyl chloride | C12H15ClO3 | 详情 | 详情 | |
| (V) | 12050 | 6,7-Dimethoxy-2-piperazino-4-quinazolinylamine; 6,7-Dimethoxy-2-piperazino-4-quinazolinamine | C14H19N5O2 | 详情 | 详情 |