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【结 构 式】 
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【药物名称】Ocinaplon, DOV-273547, CL-273547 【化学名称】7-(4-Pyridyl)-3-(pyridin-2-ylcarbonyl)pyrazolo[1,5-a]pyrimidine 【CA登记号】96604-21-6 【 分 子 式 】C17H11N5O 【 分 子 量 】301.31012 |
【开发单位】Wyeth Pharmaceuticals (Originator), DOV Pharmaceutical (Licensee) 【药理作用】Anxiolytics, Generalized Anxiety Disorder (GAD), Treatment of, PSYCHOPHARMACOLOGIC DRUGS, GABA(A) Receptor Modulators |
合成路线1
Reaction of 4-acetylpyridine (I) with hot dimethylformamide dimethyl acetal (II) gives the enamino ketone (III), which is then condensed with (3-amino-1H-pyrazol-4-yl)(2-pyridyl)methanone (IV) in boiling acetic acid. Intermediate (IV), (3-amino-1H-pyrazol-4-yl)(2-pyrid-yl)methanone, is obtained by condensation of 3-oxo-3-(2-pyridyl)propionitrile (V) with dimethylformamide dimethyl acetal (II) to provide 2-(dimethylaminomethylene)-3-oxo-3-(2-pyridyl)propionitrile (VI), which is finally coupled with aminoguanidine nitrate (VII) by means of 10N NaOH in refluxing EtOH
| 【1】 Castaner, J.; Silvestre, J.S.; Chilman-Blair, K.; Ocinaplon. Drugs Fut 2003, 28, 2, 115-120. |
| 【2】 Tomcufcik, A.S.; Dusza, J.P. (Wyeth); (3-Amino-1H-pyrazol-4-yl)(aryl)methanones. EP 0129846; JP 1985013764; US 4900836 . |
| 【3】 Dusza, J.P.; Tomcufcik, A.S.; Albright, J.D. (Wyeth); Aryl and heteroaryl 7-(aryl and heteroaryl)-pyrazolo[1,5-a]pyrimidin-3-ylmethanones. DE 3422844; EP 0129847; JP 1985019788 . |
| 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) | 59510 | 4-Acetylpyridine; Methyl 4-pyridyl ketone | 1122-54-9 | C7H7NO | 详情 | 详情 |
| (II) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (III) | 59511 | (E)-3-(dimethylamino)-1-(4-pyridinyl)-2-propen-1-one | C10H12N2O | 详情 | 详情 | |
| (IV) | 59512 | (3-amino-1H-pyrazol-4-yl)(2-pyridinyl)methanone | C9H8N4O | 详情 | 详情 | |
| (V) | 59513 | 3-oxo-3-(2-pyridinyl)propanenitrile | C8H6N2O | 详情 | 详情 | |
| (VI) | 59514 | (E)-3-(dimethylamino)-2-(2-pyridinylcarbonyl)-2-propenenitrile | C11H11N3O | 详情 | 详情 | |
| (VII) | 10015 | 1-Hydrazinecarboximidamide; Hydrazinecarboximidamide | 79-17-4 | CH6N4 | 详情 | 详情 |