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【结 构 式】 
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【药物名称】He-30582 【化学名称】6-[4-[4-[3-(1H-Imidazol-4-yl)propylaminoiminomethyl]piperazin-1-yl]-3-nitrophenyl]-5-methyl-2,3,4,5-tetrahydropyridazin-3-one 【CA登记号】126856-36-8 【 分 子 式 】C22H29N9O3 【 分 子 量 】467.53493 |
【开发单位】Heumann (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy |
合成路线1
The acylation of 5-methyl-6-[3-nitro-4-(piperazin-1-yl)phenyl]-4,5-dihydro-3(2H)-pyridazinone (I) with benzoyl isothiocyanate gives the benzoylthiourea (II), which is cleaved by alkaline hydrolysis with potassium carbonate and methylated with methyl iodide to the isothiouronium salt (III). This compound is condensed with 3-(1H-imidazol-4-yl)propylamine (homohistamine, IV) to yield title compound.
| 【1】 Herter, R.; Engler, H.; Pfahlert, V.; Weidner, R.; Ahrens, K.H. (Heumann Pharma GmbH & Co.); 6-Oxo-pyridazinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel. DE 3814057 . |
| 【2】 Morsdorf, P.; Engler, H.; HE 30582. Drugs Fut 1989, 14, 12, 1161. |
| 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) | 21504 | 5-methyl-6-[3-nitro-4-(1-piperazinyl)phenyl]-4,5-dihydro-3(2H)-pyridazinone | C15H19N5O3 | 详情 | 详情 | |
| (II) | 21505 | N-([4-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridazinyl)-2-nitrophenyl]-1-piperazinyl]carbothioyl)benzamide | C23H24N6O4S | 详情 | 详情 | |
| (III) | 21506 | methyl 4-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridazinyl)-2-nitrophenyl]-1-piperazinecarbimidothioate hydroiodide | C17H23IN6O3S | 详情 | 详情 | |
| (IV) | 21507 | 3-(1H-imidazol-4-yl)-1-propanamine | C6H11N3 | 详情 | 详情 | |
| (V) | 23530 | benzoyl isothiocyanate | 532-55-8 | C8H5NOS | 详情 | 详情 |
Extended Information