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【结 构 式】 
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【药物名称】FR-194921 【化学名称】2-(1-Methylpiperidin-4-yl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)pyridazin-3(2H)-one 【CA登记号】202646-80-8, 202646-82-0 (hydrochloride) 【 分 子 式 】C23H23N5O 【 分 子 量 】385.47266 |
【开发单位】Fujisawa (Originator) 【药理作用】Antidepressants, Cognition Disorders, Treatment of, Mood Disorders, Treatment of, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, Adenosine A1 Antagonists |
合成路线1
The title compound was synthesized by alkylation of the previously described 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-3(2H)-pyridazinone (I) with 4-chloro-1-methylpiperidine (II) in the presence of NaH in hot DMF.
| 【1】 Akahane, A.; Kuroda, S.; Itani, H.; Shimizu, Y. (Fujisawa Pharmaceutical Co., Ltd.); Pyrazolopyridine cpd. and pharmaceutical use thereof. EP 0925299; JP 2000514821; US 6124456; WO 9803507 . |
合成路线2
An alternative procedure consisted in the Mitsunobu coupling of pyridazinone (I) with 4-hydroxy-1-methylpiperidine (III) in the presence of either diisopropyl- or diethyl azodicarboxylate and triphenylphosphine
| 【1】 Kuroda, S.; et al.; Design, synthesis and biological evaluation of a novel series of potent, orally active adenosine A1 receptor antagonists with high blood-brain barrier permeability. Chem Pharm Bull 2001, 49, 8, 988. |
| 【2】 Akahane, A.; Kuroda, S.; Itani, H.; Shimizu, Y. (Fujisawa Pharmaceutical Co., Ltd.); Pyrazolopyridine cpd. and pharmaceutical use thereof. EP 0925299; JP 2000514821; US 6124456; WO 9803507 . |