【药物名称】Pranlukast hydrate, Ono-1070(monoNa salt), SB-205312, RS-411, Ono-RS-411, Ono-1078, Ultair, Onon
化学结构式(Chemical Structure):
参考文献No.4011
标题:(Fused) benz(thio)amides and pharmaceutical use
作者:Toda, M.; Arai, Y.; Miyamoto, T. (Ono Pharmaceutical Co., Ltd.)
来源:AU 8546462; EP 0173516; JP 8650977; US 4780469; US 4939141
合成路线图解说明:

The reaction of ethyl 8-nitro-4-oxo-1-benzopyran-2-carboxylate (I) with ammonia in methanol gives the corresponding amide (II), which is dehydrated with POCl3 yielding 2-cyano-8-nitro-1-benzopyran-4-one (III). The cyclization of (III) with sodium azide by means of pyridinium chloride in hot DMF affords 8-nitro-2-(tetrazol-5-yl)-1-benzopyran-4-one (IV), which is hydrogenated with H2 over Pd/C in methanol - HCl giving 8-amino-2-(tetrazol-5-yl)-1-benzopyran-4-one (V). Finally, this compound is condensed with 4-(4-phenylbutoxy)benzoic acid (VI) by means of oxalyl chloride in dichloromethane-pyridine.

参考文献No.62397
标题:ONO-RS-411
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1988,13(4),317
合成路线图解说明:

The reaction of ethyl 8-nitro-4-oxo-1-benzopyran-2-carboxylate (I) with ammonia in methanol gives the corresponding amide (II), which is dehydrated with POCl3 yielding 2-cyano-8-nitro-1-benzopyran-4-one (III). The cyclization of (III) with sodium azide by means of pyridinium chloride in hot DMF affords 8-nitro-2-(tetrazol-5-yl)-1-benzopyran-4-one (IV), which is hydrogenated with H2 over Pd/C in methanol - HCl giving 8-amino-2-(tetrazol-5-yl)-1-benzopyran-4-one (V). Finally, this compound is condensed with 4-(4-phenylbutoxy)benzoic acid (VI) by means of oxalyl chloride in dichloromethane-pyridine.

合成路线图解说明:

2) The acid chloride (IV) is reacted with chloroethanol to give compound (V), which, upon condensation with a piperazine (I), yields lobuprofen.

参考文献No.328085
标题:New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships
作者:Nakai, H.; Konno, M.; Kosuge, S.; Sakuyama, S.; Toda, M.; Arai, Y.; Obata, T.; Katsube, N.; Miyamoto, T.; Okegawa, T.; et al.
来源:J Med Chem 1988,31(1),84-91
合成路线图解说明:

The reaction of ethyl 8-nitro-4-oxo-1-benzopyran-2-carboxylate (I) with ammonia in methanol gives the corresponding amide (II), which is dehydrated with POCl3 yielding 2-cyano-8-nitro-1-benzopyran-4-one (III). The cyclization of (III) with sodium azide by means of pyridinium chloride in hot DMF affords 8-nitro-2-(tetrazol-5-yl)-1-benzopyran-4-one (IV), which is hydrogenated with H2 over Pd/C in methanol - HCl giving 8-amino-2-(tetrazol-5-yl)-1-benzopyran-4-one (V). Finally, this compound is condensed with 4-(4-phenylbutoxy)benzoic acid (VI) by means of oxalyl chloride in dichloromethane-pyridine.

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