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【结 构 式】

【药物名称】Doxefazepam, SAS-643, Doxans

【化学名称】7-Chloro-5-(o-fluorophenyl)-1,3-dihydro-3-hydroxy-1-(2-hydroxyethyl)-2H-1,4-benzodiazepin-2-one

【CA登记号】40762-15-0

【 分 子 式 】C17H14ClFN2O3

【 分 子 量 】348.76413

【开发单位】Schiapparelli Farmaceutici (Originator)

【药理作用】PSYCHOPHARMACOLOGIC DRUGS, Sedative/Hypnotics, Sleep Disorders, Treatment of, Benzodiazepines, GABA(A) BZ Site Receptor Agonists

合成路线1

Compound can be prepared in two similar ways both starting from 7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one-4-oxide (I): 1) The condensation of (I) with 2-bromoethanol (A) by means of NaH in DMF gives the N-hydroxyethyl derivative (II), which by refluxing with acetic anhydride is converted into 7-chloro-1,3-dihydro-1-(2-acetoxyethyl)-3-acetoxy-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-one (III). Finally, (III) is deacetylated with methanolic ammonia. 2) The condensation of (I) with 2-bromoethylacetate (B) as before gives the N-acetoxyethyl derivative (IV), which by refluxing with acetic anhydride is converted into (III).

1 Tamagnone, G.F.; et al.; A new benzodiazepine: 1-(2-hydroxyethyl)-3-hydroxy-7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepine-2-one. J Pharm Pharmacol 1974, 26, 566.
2 De Marchi, F.; Tamagnone, G.F.; Benzodiazepine compounds for therapeutical use. DE 2338058; ES 405260; FR 2194432; GB 1431282; JP 49080086 .
3 Tamagnone, G.F.; et al.; A new series of benzodiazepines: 1-Hydroxyalkyl derivatives of 1,3-dihydro-2H-1,4-benzodiazepin-2-one. Arzneim-Forsch Drug Res 1975, 25, 5, 720-722.
4 de Angelis, L.; Castaner, J.; SAS-643. Drugs Fut 1978, 3, 2, 145.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10059 Ethylene bromohydrin; 2-Bromo-1-ethanol 540-51-2 C2H5BrO 详情 详情
(B) 33463 2-bromoethyl acetate 927-68-4 C4H7BrO2 详情 详情
(I) 33459 7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate C15H10ClFN2O2 详情 详情
(II) 33460 7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate C17H14ClFN2O3 详情 详情
(III) 33461 2-[3-(acetoxy)-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]ethyl acetate C21H18ClFN2O5 详情 详情
(IV) 33462 1-[2-(acetoxy)ethyl]-7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate C19H16ClFN2O4 详情 详情
Extended Information