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【结 构 式】 
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【药物名称】Prinoxodan, RGW-2938, WHR-2938 【化学名称】3-Methyl-6-(3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,2,3,4-tetrahydroquinazolin-2-one 【CA登记号】111786-07-3 【 分 子 式 】C13H14N4O2 【 分 子 量 】258.28213 |
【开发单位】Aventis Pharma (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy |
合成路线1
The cyclization of 2-(methylaminomethyl)aniline (I) with 1,1'-carbonyldiimidazole (II) in refluxing THF gives 3-methyl-1,2,3,4-tetrahydroquinazolin-2-one (III), which is condensed with methyl succinyl chloride (IV) by means of anhydrous AlCl3 in refluxing carbon disulfide to yield 6-[3-(methoxycarbonyl)propionyl]-3-methyl-1,2,3,4-tetrahydroquinazolin-2-one (V). Finally, this compound is cyclocondensed with hydrazine in refluxing ethanol.
| 【1】 Kuhla, D.E.; Campbell, H.F.; Studt, W.L.; Faith, W.C.; Molino, B.F. (Aventis Pharma SA); Benzodiazinone-pyridazinone and hydroxy-pyrazolyl cpds., cardiotonic compsns. including the same, and their uses. EP 0247177; JP 1988502030; US 4725686; WO 8703201 . |
| 【2】 Prous, J.; Castaner, J.; RGW-2938. Drugs Fut 1989, 14, 2, 132. |
| 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) | 20377 | 2-[(methylamino)methyl]aniline; N-(2-aminobenzyl)-N-methylamine | C8H12N2 | 详情 | 详情 | |
| (II) | 11353 | 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) | 530-62-1 | C7H6N4O | 详情 | 详情 |
| (III) | 20379 | 3-methyl-3,4-dihydro-2(1H)-quinazolinone | 24365-65-9 | C9H10N2O | 详情 | 详情 |
| (IV) | 18060 | 4-Chloro-4-oxobutyric acid methyl ester; 3-Carbomethosypropionyl chloride; Methyl 4-chloro-4-oxobutanoate | 1490-25-1 | C5H7ClO3 | 详情 | 详情 |
| (V) | 20381 | methyl 4-(3-methyl-2-oxo-1,2,3,4-tetrahydro-6-quinazolinyl)-4-oxobutanoate | C14H16N2O4 | 详情 | 详情 |
Extended Information