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【结 构 式】 
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【药物名称】BAY-58-2667 【化学名称】4-[N-(4-Carboxybutyl)-N-[2-[2-[4-(2-phenylethyl)benzyloxy]phenyl]ethyl]aminomethyl]benzoic acid 【CA登记号】329773-35-5 【 分 子 式 】C36H39NO5 【 分 子 量 】565.71593 |
【开发单位】Bayer (Originator) 【药理作用】Antiplatelet Therapy, CARDIOVASCULAR DRUGS, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Hypertension, Treatment of, Vasodilators, Guanylate Cyclase Activators |
合成路线1
2-Methoxyphenethylamine (I) is condensed with methyl 4-formylbenzoate (II) to form imine (III), which is further reduced to amine (IV) with NaBH4 in MeOH. Alkylation of amine (IV) by ethyl 5-bromovalerate (V) affords the amino diester (VI). Methyl ether cleavage in (VI) by means of BBr3 gives rise to the phenol compound (VII), which is alkylated with 4-(chloromethyl)stilbene (VIII) to yield ether (IX). Catalytic hydrogenation of stilbene (IX) yields the phenethylbenzyl derivative (X). Finally, alkaline hydrolysis of the methyl ester groups of (X) leads to the title dicarboxylic acid.
| 【1】 Perzborn, E.; Stasch, J.-P.; Heil, M.; Naab, P.; Dembowsky, K.; Alonso-Alija, C.; Stahl, E.; Pernerstorfer, J.; Flubacher, D.; Wunder, F. (Bayer AG); Novel derivs. of dicarboxylic acid having pharmaceutical properties. DE 19943635; EP 1216225; WO 0119780 . |
| 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) | 57674 | 1-Amino-2-(2-methoxyphenyl)ethane; 2-(2-Aminoethyl)anisole; 2-(2-Methoxyphenyl)ethylamine; 2-Methoxyphenethylamine | 2045-79-6 | C9H13NO | 详情 | 详情 |
| (II) | 10170 | methyl 4-formylbenzoate | 1571-08-0 | C9H8O3 | 详情 | 详情 |
| (III) | 57675 | methyl 4-{[(2-methoxyphenethyl)imino]methyl}benzoate | C18H19NO3 | 详情 | 详情 | |
| (IV) | 57676 | methyl 4-{[(2-methoxyphenethyl)amino]methyl}benzoate | C18H21NO3 | 详情 | 详情 | |
| (V) | 37151 | ethyl 5-bromopentanoate | 14660-52-7 | C7H13BrO2 | 详情 | 详情 |
| (VI) | 57677 | methyl 4-{[(5-ethoxy-5-oxopentyl)(2-methoxyphenethyl)amino]methyl}benzoate | C25H33NO5 | 详情 | 详情 | |
| (VII) | 57678 | methyl 4-{[(2-hydroxyphenethyl)(5-methoxy-5-oxopentyl)amino]methyl}benzoate | C23H29NO5 | 详情 | 详情 | |
| (VIII) | 57679 | 4-Chloromethylstilbene | C15H13Cl | 详情 | 详情 | |
| (IX) | 57680 | methyl 4-({(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenylethenyl]benzyl}oxy)phenethyl]amino}methyl)benzoate | C38H41NO5 | 详情 | 详情 | |
| (X) | 57681 | methyl 4-[((5-methoxy-5-oxopentyl){2-[(4-phenethylbenzyl)oxy]phenethyl}amino)methyl]benzoate | C38H43NO5 | 详情 | 详情 |