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【结 构 式】 
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【药物名称】FR-167344 【化学名称】(E)-N-[N-[3-(3-Bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-N-methylcarbamoylmethyl]-4-(N,N-dimethylcarbamoyl)cinnamamide hydrochloride 【CA登记号】188550-14-3, 160644-75-7 (free base) 【 分 子 式 】C30H29BrCl3N5O4 【 分 子 量 】709.85973 |
【开发单位】Fujisawa (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, RESPIRATORY DRUGS, Bradykinin B2 Antagonists, Non-Steroidal Antiinflammatory Drugs |
合成路线1
Knoevenagel condensation of aldehyde (I) with malonic acid (II) provided substituted cinnamic acid (III). This was condensed with amino compound (IV) in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.HCl (EDC) and 1-hydroxy-benzotriazole (HOBt) to give amide (V), which was then converted to the hydrochloride salt by reaction with methanolic HCl.
| 【1】 Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Inamura, N.; Asano, M.; Hatori, C.; Sawai, H.; Oku, T.; Tanaka, H.; A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 2. Overcoming the species difference between guinea pig and man. J Med Chem 1998, 41, 21, 4053. |
| 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) | 25120 | 4-formyl-N,N-dimethylbenzamide | C10H11NO2 | 详情 | 详情 | |
| (II) | 12963 | Malonic acid | 141-82-2 | C3H4O4 | 详情 | 详情 |
| (III) | 25121 | (E)-3-[4-[(dimethylamino)carbonyl]phenyl]-2-propenoic acid | C12H13NO3 | 详情 | 详情 | |
| (IV) | 25122 | 2-amino-N-(3-[[(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yl)oxy]methyl]-2,4-dichlorophenyl)-N-methylacetamide | C18H17BrCl2N4O2 | 详情 | 详情 | |
| (V) | 25123 | 4-((E)-3-[[2-(3-[[(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yl)oxy]methyl]-2,4-dichloromethylanilino)-2-oxoethyl]amino]-3-oxo-1-propenyl)-N,N-dimethylbenzamide | C30H28BrCl2N5O4 | 详情 | 详情 |