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【结 构 式】

【药物名称】Razobazam, HR-175, Hoe-175

【化学名称】4,8-Dihydro-3,8-dimethyl-4-phenylpyrazolo[3,4-b][1,4]diazepine-5,7(1H,6H)-dione

【CA登记号】78466-98-5

【 分 子 式 】C14H14N4O2

【 分 子 量 】270.29328

【开发单位】Aventis Pharma (Originator)

【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS

合成路线1

The reductive cleavage of 4-phenylazo-3-methyl-5-methylaminopyrazole (I) with H2 over RaNi in ethanol gives 4-amino-3-methyl-5-methylaminopyrazole (II), which is acylated with ethoxycarbonylacetyl chloride (III) in toluene yielding 4-(ethoxycarbonylacetylamino)-3-methyl-5-methylaminopyrazole (IV). The cyclization of (IV) by means of sodium ethoxide in ethanol affords 4,8-dihydro-3,8-dimethylpyrazolo[3,4b][1,4]diazepine-5,7(1H,6H) dione (V), which is finally phenylated by a treatment with powdered Cu and potassium acetate in refluxing bromobenzene

1 Rackur, G.; Hoffmann, I. (Aventis SA); 4-Aryl-5,6,7,8-tetrahydropyrazolo[3,4-b]-[1,5]diazepine-1H,4H-5,7-diones and medicaments containing same. DD 152936; DE 2932835; EP 0024038; EP 0050376; JP 5603977; US 4302468 .
2 Castaner, J.; Prous, J.; Razobazam. Drugs Fut 1986, 11, 6, 465.
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) 24717 N,3-dimethyl-4-[(E)-2-phenyldiazenyl]-1H-pyrazol-5-amine C11H13N5 详情 详情
(II) 24718 N-(4-amino-3-methyl-1H-pyrazol-5-yl)-N-methylamine C5H10N4 详情 详情
(III) 13188 ethyl 3-chloro-3-oxopropanoate; 2-Ethoxycarbonylacetyl chloride; Ethyl malonyl chloride 36239-09-5 C5H7ClO3 详情 详情
(IV) 24720 ethyl 3-[[3-methyl-5-(methylamino)-1H-pyrazol-4-yl]amino]-3-oxopropanoate C10H16N4O3 详情 详情
(V) 24721 3,8-dimethyl-4,8-dihydropyrazolo[3,4-b][1,4]diazepine-5,7(1H,6H)-dione C8H10N4O2 详情 详情
(VI) 13365 Monobromobenzene; 1-Bromobenzene;Phenylbromide;bromobenzene 108-86-1 C6H5Br 详情 详情
Extended Information