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【结 构 式】 
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【药物名称】Procaterol hydrochloride hemihydrate, OPC-2009(anhydrous), CI-888(anhydrous), Meptin, Procadil Aerosol, Onsukil Aerosol, Masacin Aerosol 【化学名称】(±)-(R*,S*)-8-Hydroxy-5-[1-hydroxy-2-[(1-methylethyl)amino]butyl]-2(1H)-quinolinone monohydrochloride hemihydrate 【CA登记号】59828-07-8 (anhydrous), 72332-33-3 (free base, anhydrous) 【 分 子 式 】C16H25ClN2O4 【 分 子 量 】344.84165 |
【开发单位】Otsuka (Originator), Recordati (Licensee), ML Laboratories (Formulation) 【药理作用】Asthma Therapy, Bronchodilators, RESPIRATORY DRUGS, beta2-Adrenoceptor Agonists |
合成路线1
The Friedel-Crafts condensation of 8-hydroxycarbostyril (I) with 2-bromobutyryl chloride by means of AlCl3 in refluxing CS2 gives 5-(2-bromobutyryl)-8-hydroxycarbostyril (II), which by reaction with isopropylamine in isopropanol affords 5-(2-isopropylaminobutyryl)-8-hydroxycarbostyril (III). Finally, this compound is reduced with NaBH4 in methanol.
| 【1】 Nakagawa, K.; et al.; Dérivés de 5-(1-hydroxy-2-amino substitué)alkyl-8-carbostyryle substitué et de 5-(1-hydroxy-2-amino substitué)alkyl-8-(3,4-dihydro)carbostyryle substitué et leur procédé de préparation. BE 0823841; JP 50095279 . |
| 【2】 Yoshizaki, S.; et al.; Sympathomimetic amines having a carbostyril nucleus. J Med Chem 1976, 19, 9, 35-45. |
| 【3】 Castaner, J.; Weetman, D.F.; Procaterol. Drugs Fut 1978, 3, 2, 135. |
| 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) | 39072 | 8-hydroxy-2(1H)-quinolinone | 15450-76-7 | C9H7NO2 | 详情 | 详情 |
| (II) | 39781 | 2-bromobutanoyl chloride | 22118-12-3 | C4H6BrClO | 详情 | 详情 |
| (III) | 39782 | 5-(2-bromobutanoyl)-8-hydroxy-2(1H)-quinolinone | C13H12BrNO3 | 详情 | 详情 | |
| (IV) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
| (V) | 39783 | 8-hydroxy-5-[2-(isopropylamino)butanoyl]-2(1H)-quinolinone | C16H20N2O3 | 详情 | 详情 |