CGS-9896, -Drug Synthesis Database

【结构式】

【药物名称】CGS-9896

【化学名称】2-(4-Chlorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one

【CA登记号】77779-36-3

【分子式】C₁₆H₁₀ClN₃O

【分子量】295.7306

【开发单位】Novartis (Originator)

【药理作用】Antiepileptic Drugs, Anxiolytics, NEUROLOGIC DRUGS, PSYCHOPHARMACOLOGIC DRUGS, GABA(A) BZ Site Receptor Partial Agonists

合成路线1

The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III), which is cyclized to ethyl 4-hydroxyquinoline-3carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl. The reaction of (IV) with hot POCl3 affords ethyl-4-chloroquinoline-3-carboxylate (V), which is finally cyclized with 4-chlorophenylhydrazine (VIII) by heating at 105 C in xylene. (VIII) is prepared in the usual way starting from 4-chloroaniline (IX) by diazotation with NaNO2-HCl to 4-chlorophenyldiazonium chloride (X), and reduction with SnCl2-HCl.

参考文献中间体

【1】 Yokoyama, N.; US 4312870 .
【2】 Yokoyama, N.; EP 0022078 .
【3】 Ritter, B.; Yokoyama, N.; Neubert, A.D.; 2-Arylpyrazolo[4,3-c]quinolin-3-ones: A partial novel agonist and antagonist of benzodiazepines. J Med Chem 1982, 25, 4, 337-339.
【4】 Castaner, J.; Blancafort, P.; Grau, M.; Serradell, M.N.; CGS-8216 and CGS-9896. Drugs Fut 1983, 8, 2, 99.

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)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(II)	14088	Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate	87-13-8	C₁₀H₁₆O₅	详情	详情
(III)	35953	diethyl 2-(anilinomethylene)malonate		C₁₄H₁₇NO₄	详情	详情
(IV)	35954	ethyl 4-hydroxy-3-quinolinecarboxylate		C₁₂H₁₁NO₃	详情	详情
(V)	35955	ethyl 4-chloro-3-quinolinecarboxylate		C₁₂H₁₀ClNO₂	详情	详情
(VIII)	33345	1-(4-chlorophenyl)hydrazine; 4-Chlorophenylhydrazine	1073-70-7	C₆H₇ClN₂	详情	详情
(IX)	12034	4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline	106-47-8	C₆H₆ClN	详情	详情
(X)	10197	4-Chlorobenzenediazonium chloride		C₆H₄Cl₂N₂	详情	详情

Extended Information

FDA Approved Drug Products(1)