【药物名称】KF-15570
化学结构式(Chemical Structure):
参考文献No.13087
标题:Imidazoquinoline derivs
作者:Suzuki, F.; Kuroda, T.; Nakazato, Y.; Manabe, H.; Ohmori, K. (Kyowa Hakko Kogyo Co., Ltd.)
来源:EP 0386722; JP 1991264585; US 4994468
合成路线图解说明:

KF15570 is prepared as follows: 1-Butylisatoic anhydride (I) (3) was reacted with anion of ethylnitroacetate to give 1-butyl-4-hydroxy-3-nitroquinolin-2(1H)-one. Without purification, the hydroxy group was chlorinated with phosphorus oxychloride under reflux to give (II). The chlorine in (II) was readily replaced by methyl amino group in THF to provide (III). Hydrogenation of the nitro group in (III), followed by cyclization in refluxing triethylorthoformate, afforded KF15570 (IV).

参考文献No.183829
标题:KF15570
作者:Suzuki, F.
来源:Drugs Fut 1992,17(10),873
合成路线图解说明:

KF15570 is prepared as follows: 1-Butylisatoic anhydride (I) (3) was reacted with anion of ethylnitroacetate to give 1-butyl-4-hydroxy-3-nitroquinolin-2(1H)-one. Without purification, the hydroxy group was chlorinated with phosphorus oxychloride under reflux to give (II). The chlorine in (II) was readily replaced by methyl amino group in THF to provide (III). Hydrogenation of the nitro group in (III), followed by cyclization in refluxing triethylorthoformate, afforded KF15570 (IV).

参考文献No.195403
标题:New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones
作者:Suzuki, F.; Kuroda, T.; Nakasato, Y.; Manabe, H.; Ohmori, K.; Kitamura, S.; Ichikawa, S.; Ohno, T.
来源:J Med Chem 1992,35(22),4045
合成路线图解说明:

A new synthesis for KF-15570 has been described: The oxidation of 1-methyl-1H-imidazo[4,5-c]quinoline (I) with H2O2 in hot acetic acid gives 4-hydroxy-1-methyl-1H-imidazo[4,5-c]quinoline (II), which is then alkylated with butyl iodide and NaH in hot DMF. Compound was much more potent than theophylline in inhibiting Schulz-Dale reaction-induced tracheal contractions (ID50 = 0.25 mcM) and showed similar acute toxicity in mice (minimal lethal dose > 300 mg/kg i.v.). It was more effective than aminophylline in inhibiting antigen-induced bronchoconstriction in anesthetized guinea pigs (ED50 = 0.42 mg/kg i.v.), but showed fewer cardiac and CNS side effects than theophylline.

参考文献No.802095
标题:New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones
作者:Suzuki, F.; Kuroda, T.; Nakasato, Y.; Manabe, H.; Ohmori, K.; Kitamura, S.; Ichikawa, S.; Ohno, T.
来源:J Med Chem 1992,35(22),4045-53
合成路线图解说明:

KF15570 is prepared as follows: 1-Butylisatoic anhydride (I) (3) was reacted with anion of ethylnitroacetate to give 1-butyl-4-hydroxy-3-nitroquinolin-2(1H)-one. Without purification, the hydroxy group was chlorinated with phosphorus oxychloride under reflux to give (II). The chlorine in (II) was readily replaced by methyl amino group in THF to provide (III). Hydrogenation of the nitro group in (III), followed by cyclization in refluxing triethylorthoformate, afforded KF15570 (IV).

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