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【结 构 式】 
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【药物名称】Aptiganel, CNS-1102, Cerestat(former Brand Name) 【化学名称】N1-(3-Ethylphenyl)-N1-methyl-N3-(1-naphthyl)guanidine 【CA登记号】137159-92-3, 137160-11-3 (monoHCl) 【 分 子 式 】C20H21N3 【 分 子 量 】303.41047 |
【开发单位】CeNeS (Originator) 【药理作用】Antiparkinsonian Drugs, Cerebrovascular Diseases, Treatment of, Extrapyramidal Disorders, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, NMDA Antagonists |
合成路线1
(3-Ethylphenyl)cyanamide (III) was prepared by treatment of m-ethylaniline (I) with cyanogen bromide (II) in Et2O. Alkylation of (III) with iodomethane and NaH provided the N-methyl cyanamide (IV). This was finally condensed with 1-naphthylamine hydrochloride (V) by heating at 160 C or in the presence of AlCl3 as the catalyst.
| 【1】 Weber, E.; Keana, J.F.W. (University of Oregon); Tri- and tetra-substd. guanidines and their use as excitatory amino acid antagonists. JP 2002020361; US 5262568; WO 9112797 . |
| 【2】 Durant, G.J.; Nagar, S.S. (CeNeS Pharmaceuticals); Preparation of substd. guanidines. WO 9319042 . |
| 【3】 Reddy, N.L.; et al.; Synthesis and structure-activity studies of N,N'-diarylguanidine derivatives. N-(1-naphthyl)-N'-(3-ethylphenyl)-N'-methylguanidine: A new, selective noncompetitive NMDA receptor antagonist. J Med Chem 1994, 37, 2, 260. |
| 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) | 59208 | 3-Ethylaniline; m-Ethylaniline | 587-02-0 | C8H11N | 详情 | 详情 |
| (II) | 58017 | (4S)-4-(3-chloropropyl)-2,2-dimethyl-1,3-dioxolane | C8H15ClO2 | 详情 | 详情 | |
| (III) | 59209 | 3-ethylphenylcyanamide | C9H10N2 | 详情 | 详情 | |
| (IV) | 59210 | 3-ethylphenyl(methyl)cyanamide | C10H12N2 | 详情 | 详情 | |
| (V) | 59211 | 1-Aminonaphthalene; 1-Naphthylamine; alpha-Naphthylamine | 134-32-7 | C10H9N | 详情 | 详情 |
Extended Information