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【结 构 式】 
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【药物名称】GENZ-29155 【化学名称】2-Benzoyl-N-[1-(3-cyanophenyl)-1-[N-(2,2-diphenylethyl)carbamoylmethyl]-N-[2-(1H-imidazol-4-yl)ethyl]benzamide 【CA登记号】374080-21-4, 374080-26-9 ((R)-isomer), 374080-27-0 ((S)-isomer) 【 分 子 式 】C42H35N5O3 【 分 子 量 】657.77895 |
【开发单位】Genzyme (Originator) 【药理作用】Immunologic Neuromuscular Disorders, Treatment of, IMMUNOMODULATING AGENTS, Multiple Sclerosis, Agents for, NEUROLOGIC DRUGS, Treatment of Transplant Rejection, Apoptosis Inhibitors |
合成路线1
2,2-Diphenylethylamine (I) is converted into the corresponding formamide (II) upon refluxing in ethyl formate. Subsequent dehydration of formamide (II) with phosphorus oxychloride in the presence of diisopropylamine furnishes isocyanide (III)
| 【1】 Hirth, B.H.; Sneddon, S.F.; Kane, J.L.; Vinick, F.; Qiao, S.; Nahill, S.R. (Genzyme Corp.); Modulators of TNF-alpha signaling. WO 0187849 . |
合成路线2
The title compound is prepared according to the Ugi reaction by combination of the four components: isocyanide (III), m-cyanobenzaldehyde (IV), 2-benzoylbenzoic acid (V), and histamine (VI) in refluxing MeOH
| 【1】 Hirth, B.H.; Bernasconi, R.; Biemann, H.P.; et al.; Discovery of TNF-alpha induced apoptosis inhibitors with activity in a murine model of multiple sclerosis: Glycine diamides. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 272. |
| 【2】 Hirth, B.H.; Sneddon, S.F.; Kane, J.L.; Vinick, F.; Qiao, S.; Nahill, S.R. (Genzyme Corp.); Modulators of TNF-alpha signaling. WO 0187849 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 60310 | C15H13N | 详情 | 详情 | ||
| (IV) | 13245 | 3-Formylbenzonitrile; 3-Cyanobenzaldehyde | 24964-64-5 | C8H5NO | 详情 | 详情 |
| (V) | 59365 | 2-benzophenone carboxylic acid; 2-Benzoylbenzoic acid; 2-Carboxybenzophenone; Benzophenone-2-carboxylic acid; O-benzoylbenzoic acid | 85-52-9 | C14H10O3 | 详情 | 详情 |
| (VI) | 60311 | 2-(1H-imidazol-5-yl)-1-ethanamine; 2-(1H-imidazol-5-yl)ethylamine | C5H9N3 | 详情 | 详情 |