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【结 构 式】 
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【药物名称】Semapimod hydrochloride, AXD-455, CNI-1493 【化学名称】N,N'-Bis[3,5-bis[1-(2-amidinohydrazono)ethyl]phenyl]decanediamide tetrahydrochloride 【CA登记号】164301-51-3, 352513-83-8 (free base) 【 分 子 式 】C34H56Cl4N18O2 【 分 子 量 】890.75682 |
【开发单位】Picower Institute for Medical Research (Originator), Axxima (Licensee), Cytokine PharmaSciences (Licensee), Cytokine PharmaSciences (Codevelopment) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Antipsoriatics, DERMATOLOGIC DRUGS, GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, Oncolytic Drugs, Pancreatic Disorders, Treatment of, Renal Cancer Therapy, Mitogen-Activated Protein (MAP) Kinase Inhibitors, Nitric Oxide Synthase Inhibitors |
合成路线1
The reaction of decanedioyl dichloride (I) with 3,5-diacetylaniline (II) by means of pyridine in dichloromethane gives the corresponding diamide (III), which is condensed with aminoguanidine (IV) in refluxing aqueous ethanol to afford the target tetrakis amidinohydrazone.
| 【1】 Cerami, A.; Ulrich, P.; Tracey, K.J.; Bianchi, M. (Picower Institute for Medical Research); Guanylhydrazones for treating inflammatory conditions. EP 0746312; EP 1160240; US 5599984; WO 9519767 . |
| 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) | 53486 | Sebacic acid chloride; Sebacoyl chloride; Sebacoyl dichloride; Sebacic acid dichloride | 111-19-3 | C10H16Cl2O2 | 详情 | 详情 |
| (II) | 53487 | 1-(3-acetyl-5-aminophenyl)-1-ethanone | n/a | C10H11NO2 | 详情 | 详情 |
| (III) | 53488 | N1,N10-bis(3,5-diacetylphenyl)decanediamide | n/a | C30H36N2O6 | 详情 | 详情 |
| (IV) | 10015 | 1-Hydrazinecarboximidamide; Hydrazinecarboximidamide | 79-17-4 | CH6N4 | 详情 | 详情 |