KR890002019A - 8-substituted quinoline carboxylic acid derivatives and preparation method thereof - Google Patents

Abstract

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Description

8-position substituted quinolone diacid derivative and preparation method thereof

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Claims (7)

The compounds of formula (I) and the hydrates of the spheres and pharmaceutically acceptable salts. Wherein R represents chlorine, bromine, nitro, cyano, -RO ² , -SR ² , or -NR ² R ³ , wherein R ² and R ³ are each independently hydrogen or lower alkyl. R ¹ represents ethyl, 4-fluorophenyl or 2.4-difluoro phenyl: Z is of the general formula A piperazino group of wherein R ⁴ is hydrogen, methyl or lower alkoxycarbonyl and R ⁵ is hydrogen or lower alkyl A pyrrolidine group wherein n is 0 or 1 degree, R ⁶ is hydrogen or methyl, R ⁷ is hydrogen or lower alkyl, and R ⁸ is hydrogen, lower alkyl, lower acyl or alkoxycarbonyl Provided that if R ¹ is ethyl and R is chlorine, then Z is not piperazino or 4-methylpiperazino. The compound of formula (II) is nitrated, and when R ⁹ is lower alkyl, the resulting condensation product is hydrolyzed to produce a carboxylic acid derivative, thereby preparing a compound of formula (III ′) How to. Wherein R ¹ represents ethyl, 4-fluorophenyl or 2.4-difluoro phenyl: Z is of the general formula The piperazino group of wherein R ⁴ is hydrogen, methyl or lower alkoxycarbonyl and R ⁵ is hydrogen or lower alkyl. Or general formula A pyrrolidine group wherein n is 0 or 1, R ⁶ is hydrogen or methyl, R ⁷ is hydrogen or lower alkyl, R ⁸ is hydrogen, lower alkyl, lower acyl or lower alkoxycarbonyl R ⁹ represents hydrogen or lower alkyl. The compound of formula (III) is reduced, and when R ⁹ is lower alkyl, the resulting product is hydrolyzed to form a carboxylic acid derivative, thereby producing a compound of formula (IV ′) . Wherein R ¹ represents ethyl, 4-fluorophenyl or 2.4-difluorophenyl, and Z is a general formula A piperazino group of wherein R ⁴ is hydrogen, methyl or lower alkoxycarbonyl and R ⁵ is hydrogen or lower alkyl. Or general formula A pyrrolidine group wherein n is 0 or 1, R ⁶ is hydrogen or methyl, R ⁷ is hydrogen or lower alkyl, and R ⁸ is hydrogen, lower alkyl, lower acyl or lower alkoxycarbonyl R ⁹ represents hydrogen or lower alkyl. Diazotizing the compound of the following formula (IV), and then reacting the resulting compound with a metal halide or metal cyanide, and when R ⁹ is lower alkyl, hydrolysis of the resultant side product produces a carboxylic acid derivative. To prepare a compound of formula (V ′). Wherein R ¹ represents ethyl, 4-fluorophenyl or 2.4-difluorophenyl: R ¹⁰ represents chlorine, bromine or cyano and Z is a general formula The piperazino group of wherein R ⁴ is hydrogen, methyl or lower alkoxycarbonyl and R ⁵ is hydrogen or lower alkyl. Or general formula Pyrrolidine group of wherein n is 0 or 1, R ⁶ is hydrogen or methyl, R ⁷ is hydrogen or lower alkyl, R ⁸ is hydrogen, lower alkyl, lower acyl or lower alkoxycarbonyl Represents; R ⁹ represents hydrogen or lower alkyl, provided that if R ¹ is ethyl and R ¹⁰ is chlorine then Z is not piperazino or 4-methylpiperazino. The compound of formula (VI) may be selected from the group consisting of alkali metal alcoholates, alkali metal alkalthiolates, alkali metal hydroxides, alkali metal hydrogen sulphates or amines of the general formula HNR ² R ³ , wherein R ² and R ³ are each independently hydrogen Or lower alkyl), and when R ⁹ is lower alkyl, the resulting condensation product is hydrolyzed to produce a carboxylic acid derivative, thereby producing a compound of formula (VII). Wherein R ¹ represents ethyl, 4-fluorophenyl or 2,4-difluoro phenyl: R ¹³ represents -OR ² , -SR ² or -NR ² R ³ , wherein R ² and R ³ are Each independently hydrogen or lower alkyl): Z is a general formula A piperazino group of wherein R ⁴ is hydrogen, methyl or lower alkoxycarbonyl and R ⁵ is hydrogen or lower alkyl, or Pyrrolidine group of wherein n is 0 or 1, R ⁶ is hydrogen or methyl, R ⁷ is hydrogen or lower alkyl, R ⁸ is hydrogen, lower alkyl, lower acyl or lower alkoxycarbonyl Hal represents halogen and R ⁹ represents hydrogen or lower alkyl. The compound of formula (VII) is reacted with a compound of formula (VII), and when R ⁹ is lower alkyl, the resulting condensation product is hydrolyzed to produce a carboxylic acid derivative. To prepare a compound. Wherein R represents chlorine, bromine, nitro, cyano, -OR ² , -SR ² or -NR ² R ³ (wherein R ² and R ³ are each independently hydrogen or swj-class alkyl): R ¹ represents ethyl, 4-fluorophenyl or 2.4-difluorophenyl: Z is a general formula A piperazino group of wherein R ⁴ is hydrogen, methyl or lower alkoxycarbonyl and R ⁵ is hydrogen or lower alkyl, or a general formula Pyrrolidine, wherein nd, s 0 or 1, R ⁶ is hydrogen or hydromethyl, R ⁷ is hydrogen or lower alkyl, R ⁸ is hydrogen, lower alkyl, lower acyl or lower alkoxycarbonyl R ⁹ represents hydrogen or lower alkyl; Z ¹ represents a halogen atom, provided that if R ¹ is ethyl and R is chlorine then Z is not piperazino or 4-methylpiperazino. An antimicrobial pharmaceutical composition comprising at least one compound as defined in claim 1 and an inert pharmaceutical acceptable carrier. ※ Note: The disclosure is based on the initial application.