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【结 构 式】 
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【药物名称】Terbogrel, BIBV-308-SE, BIBV-308 【化学名称】6-[3-(3-tert-Butyl-2-cyanoguanidino)phenyl]-6-(3-pyridyl)-5(E)-hexenoic acid 【CA登记号】149979-74-8 【 分 子 式 】C23H27N5O2 【 分 子 量 】405.50394 |
【开发单位】Boehringer Ingelheim (Originator) 【药理作用】Antiplatelet Therapy, CARDIOVASCULAR DRUGS, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Peripheral Vascular Disease, Treatment of, Treatment of Peripheral Obstructive Vascular Disease, Prostanoid TP (Thromboxane A2) Antagonists, Thromboxane Synthase Inhibitors |
合成路线1
The reaction of (E)-6-(3-aminophenyl)-6-(3-pyridyl)-5-hexenoic acid methyl ester (I) with diphenyl N-cyanocarbinimidate (II) in isopropanol gives the N-cyanoisourea (III), which is condensed with tert-butylamine (IV) in refluxing isopropanol yielding the guanidine derivative (IV). Finally, hydrolysis of the ester group of (IV) with NaOH affords the target compound.
| 【1】 Soyka, R.; et al.; Guanidine derivatives as combined thromboxane A2 receptor antagonists and synthase inhibitors. J Med Chem 1999, 42, 7, 1235. |
| 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) | 25867 | methyl (E)-6-(3-aminophenyl)-6-(3-pyridinyl)-5-hexenoate | C18H20N2O2 | 详情 | 详情 | |
| (II) | 25868 | 1-[(cyanoimino)(phenoxy)methoxy]benzene | 107-37-9 | C14H10N2O2 | 详情 | 详情 |
| (III) | 25869 | methyl (E)-6-(3-[[(cyanoimino)(phenoxy)methyl]amino]phenyl)-6-(3-pyridinyl)-5-hexenoate | C26H24N4O3 | 详情 | 详情 | |
| (IV) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
| (V) | 25870 | methyl (E)-6-(3-[[(tert-butylamino)(cyanoimino)methyl]amino]phenyl)-5-methyl-6-(3-pyridinyl)-5-hexenoate | C25H31N5O2 | 详情 | 详情 |