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【结 构 式】

【药物名称】Pazinaclone, A-77000, DN-2327

【化学名称】(±)-2-(7-Chloro-1,8-naphthyridin-2-yl)-3-[2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-oxoethyl]isoindolin-1-one
      (±)-8-[[2-(7-Chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-oxo-1H-isoindol-1-yl]acetyl]-1,4-dioxa-8-azaspiro[4.5]decane

【CA登记号】103255-66-9

【 分 子 式 】C25H23ClN4O4

【 分 子 量 】478.93946

【开发单位】Takeda (Originator), TAP (Originator)

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

合成路线1

The reaction of 2-(7-chloro-1,8-naphthyrin-2-yl)-3-hydroxyisoindolin-1-one (I) with tert-butoxycarbonylmethylenetriphenylphosphorane (II) in refluxing toluene gives 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindolin-1-acetic acid tert-butyl ester (III), which is hydrolyzed with trifluoroacetic acid to the corresponding free acid (IV). Finally, this compound is condensed with 1,4-dioxa-8-azaspiro[4.5]decane (V) by means of diethyl phosphorocyanidate and triethylamine in DMF.

1 Okada, T.; Mohler, M.; Benzodiazepine receptor: Demonstration in the central nervous system. Science 1977, 198, 849-51.
2 Goto, G.; Saji, Y. (Takeda Chemical Industries, Ltd.); Isoindolinone derivs., production and use thereof. EP 0174858; JP 1986069773; JP 1990262578; JP 1992364180; US 4778801 .
3 Graul, A.; Prous, J.; Castaner, J.; DN-2327. Drugs Fut 1993, 18, 5, 414.
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) 11334 2-(7-Chloro[1,8]naphthyridin-2-yl)-3-hydroxy-1-isoindolinone C16H10ClN3O2 详情 详情
(II) 11335 tert-butyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (tert-Butoxycarbonylmethylene)triphenylphosphorane 35000-38-5 C24H25O2P 详情 详情
(III) 11336 tert-butyl 2-[2-(7-chloro[1,8]naphthyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetate C22H20ClN3O3 详情 详情
(IV) 11337 2-[2-(7-chloro[1,8]naphthyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid C18H12ClN3O3 详情 详情
(V) 11338 1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal 177-11-7 C7H13NO2 详情 详情
Extended Information