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【结 构 式】 
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【药物名称】Sarpogrelate hydrochloride, MCI-9042, Anplag 【化学名称】Succinic acid (±)-1-(dimethylaminomethyl)-2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl monoester hydrochloride 【CA登记号】135159-51-2, 125926-17-2 (free base) 【 分 子 式 】C24H32ClNO6 【 分 子 量 】465.97874 |
【开发单位】Mitsubishi Pharma (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Antiplatelet Therapy, CARDIOVASCULAR DRUGS, Cerebrovascular Diseases, Treatment of, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, NEUROLOGIC DRUGS, Peripheral Vascular Disease, Treatment of, Stroke, Treatment of, Treatment of Intermittent Claudication, 5-HT2A Antagonists |
合成路线1
The reaction of 2-hydroxy-3'-methoxybibenzyl (I) with epichlorohydrin (II) by means of NaH in DMF gives 2-(2,3-epoxypropoxy)-3'-methoxybibenzyl (III), which by reaction with dimethylamine in refluxing THF yields 2-[3-(dimethylamino)-2-hydroxypropoxy]-3'-methoxybibenzyl (IV). Finally, this compound is treated with succinic anhydride (V) in refluxing THF and with HCl in acetone.
| 【1】 Kikumoto, R.; Fukami, H.; Hara, H.; Ninomiya, K.; Sugano, M. (Mitsubishi Chemical Corp.); Pharmaceutically active (3-aminopropoxy)-bibenzyl derivs. EP 0072942 . |
| 【2】 Prous, J.; Castaner, J.; Sarpogrelate Hydrochloride. Drugs Fut 1992, 17, 12, 1093. |
| 【3】 Osakabe, M.; Fukami, H.; Sugano, M.; Kikumoto, R.; Ninomiya, K.; Tamao, Y.; Hara, H.; Syntheses and platelet aggregation inhibitory and antithrombotic properties of [2-[(omega-aminoalkoxy)phenyl]ethyl]benzenes. J Med Chem 1990, 33, 6, 1818. |
| 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) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (II) | 13604 | 2-(3-Methoxyphenethyl)phenol | C15H16O2 | 详情 | 详情 | |
| (III) | 13605 | 2-(3-Methoxyphenethyl)phenyl 2-oxiranylmethyl ether; 2-[[2-(3-Methoxyphenethyl)phenoxy]methyl]oxirane | C18H20O3 | 详情 | 详情 | |
| (IV) | 13606 | 1-(Dimethylamino)-3-[2-(3-methoxyphenethyl)phenoxy]-2-propanol | C20H27NO3 | 详情 | 详情 | |
| (V) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |