• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】Motapizone, NAT-5239

【化学名称】(±)-4,5-Dihydro-6-[4-(1H-imidazol-1-yl)-2-thienyl]-5-methyl-3(2H)-pyridazinone

【CA登记号】90697-57-7

【 分 子 式 】C12H12N4OS

【 分 子 量 】260.31964

【开发单位】Nattermann (Originator)

【药理作用】Antiplatelet Therapy, CARDIOVASCULAR DRUGS, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Hypertension, Treatment of, Vasodilators

合成路线1

The reaction of 4-bromo-2-thiophienecarboxaldehyde (I) with imidazole yields 4-(1H-imidazol-1-yl)-2 thiophenecarboxaldehyde (II), which by cyanide-catalyzed conjugate addition to 2-butenenitrile (III) in DMF is converted to 4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutyronitrile (IV). Hydrolysis of (IV) in refluxing 4N HCl gives 4-[4-(1H imidazol-1-yl)-2-thienyl-4 oxobutanoic acid (V), which is finally cyclized with hydrazine in refluxing water to afford motapizone.

1 Borbe, H.; Doppelfeld, I.-S.; Hilboll, G.; Lohr, J.P.; Prop, G. (A. Nattermann & Cie. GmbH); Imidazolylalkylthienyl tetrahydropyridazines and processes for their use. DE 3241102; EP 0112987; US 4644998 .
2 Prop, G.; Hilboll, G.; Borbe, H.O.; Motapizone. Drugs Fut 1986, 11, 1, 24.
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) 24142 4-bromo-2-thiophenecarbaldehyde 18791-75-8 C5H3BrOS 详情 详情
(II) 24143 4-(1H-Imidazol-1-yl)-2-thiophenecarbaldehyde; 4-(1H-Imidazol-1-yl)-2 thiophenecarboxaldehyde C8H6N2OS 详情 详情
(III) 24144 (E)-2-butenenitrile 4786-20-3 C4H5N 详情 详情
(IV) 24145 4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutanenitrile C12H11N3OS 详情 详情
(V) 24146 4-[4-(1H-imidazol-1-yl)-2-thienyl]-3-methyl-4-oxobutyric acid C12H12N2O3S 详情 详情
Extended Information