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【结 构 式】 
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【药物名称】Suritozole, MDL-26479 【化学名称】5-(3-Fluorophenyl)-2,4-dimethyl-3,4-dihydro-2H-1,2,4-triazole-3-thione 【CA登记号】110623-33-1 【 分 子 式 】C10H10FN3S 【 分 子 量 】223.2737 |
【开发单位】Aventis Pharma (Originator) 【药理作用】Antidepressants, Cognition Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, GABA(A) Receptor Agonists |
合成路线1
The reaction of methyl hydrazine (I) and methyl isothiocyanate (II) in either ethanol or THF afforded 2,4-dimethylthiosemicarbazide (III). Acylation of (III) with 3-fluorobenzoyl chloride in either pyridine or THF/N(Et)3 yielded 1-(3-fluorobenzoyl)-2,4-dimethylthiosemicarbazide (IV), which was easily cyclized to MDL 26,479 by warming in 1 M aqueous NaOH.
| 【1】 Miller, J.A.; Dudley, M.W.; Kehne, J.H.; Sorensen, S.M.; Wenstrup, D.L.; Kane J.M.; MDL 26,479. Drugs Fut 1992, 17, 1, 21. |
| 【2】 Dudley, M.W.; Baron, B.M.; Sorensen, S.M.; Miller, F.P.; MDL 26,479: A potential antidepressant whose mechanism of action involves interaction at the GABAA receptor complex. 29th Annu Meet Amer Coll Neuropsychopharmacol (Dec 10-14, San Juan) 1990, Abst. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 63420 | 3-fluorobenzoyl chloride | C7H4ClFO | 详情 | 详情 | ||
| (I) | 12091 | 1-Methylhydrazine; Monomethyl hydrazine | 60-34-4 | CH6N2 | 详情 | 详情 |
| (II) | 12092 | Methyl isothiocyanate; MITC; (Methylimino)(thioxo)methane | 556-61-6 | C2H3NS | 详情 | 详情 |
| (III) | 12093 | 2,4-Dimethylthiosemicarbazide; N,1-Dimethyl-1-hydrazinecarbothioamide | 6621-75-6 | C3H9N3S | 详情 | 详情 |
| (IV) | 12094 | 2-(3-Fluorobenzoyl)-N,1-dimethyl-1-hydrazinecarbothioamide | C10H12FN3OS | 详情 | 详情 |
Extended Information