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5-amino-8-methoxy quinolone carboxylic acid derivatives and its preparation

A technology for protecting groups of methoxy and amino groups, applied in the field of 5-amino-8-methoxyquinolone carboxylic acid derivatives and their preparation methods

Inactive Publication Date: 2004-04-28
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the 5-amino-8-methoxyquinolone analogues they synthesized, the 7-position side chain is only some of the common substituted piperazines, substituted aminopyrrolidines and substituted aminopiperidines, and the other 7-position ring aminosides chain is not evaluated

Method used

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  • 5-amino-8-methoxy quinolone carboxylic acid derivatives and its preparation
  • 5-amino-8-methoxy quinolone carboxylic acid derivatives and its preparation
  • 5-amino-8-methoxy quinolone carboxylic acid derivatives and its preparation

Examples

Experimental program
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Effect test

preparation example 1

[0124] Preparation of 1-cyclopropyl-6,7-difluoro-8-methoxy-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester

[0125] Under ice bath, ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (10.0g, 30.9mmol) Soluble in concentrated H 2 SO 4 (85.0mL), add KNO in batches 3 (4.7g, 46.4mmol) and reacted at the same temperature for 3h. After the reaction was completed, the reaction solution was poured into rapidly stirred ice water (500 mL), continued to stir for 0.5 h, filtered, and the filter cake was dried and recrystallized from methanol to obtain VII-1 (9.5 g, 83.3%) as a white solid. mp>270°C.

[0126] 1 H NMR (CDCl 3 )δ, ppm: 1.07-1.24 (4H, m), 1.36 (3H, t, J = 7.8Hz), 4.02-4.04 (1H, m), 4.17 (3H, s), 4.35 (2H, q, J = 7.8Hz), 8.60(1H, s)

preparation example 2

[0128] Preparation of 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester

[0129] Reduced iron powder (2.4g, 42.8mmol), H 2 A mixture of O (4.5mL) and glacial acetic acid (0.3mL) was reacted under reflux for 15min, a chloroform (100mL) solution of the compound (4.0g, 10.8mmol) prepared in Preparation Example 1 was added dropwise, and the reflux reaction was continued for 6h, and then After filtering, the filtrate was left to cool and washed twice with 6M HCl. Dry, filter, and remove the solvent from the filtrate to obtain a crude product, which is recrystallized from a mixed solvent of ethanol and chloroform to obtain a yellow solid (3.2 g, 87.2%), mp 209-210°C.

preparation example 3

[0131] Preparation of 5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

[0132] The compound (3.2g, 9.5mmol) prepared in Preparation Example 2 was dissolved in concentrated HCl (4.0mL) and HOAc (16.0mL), reacted at 100°C for 1h, concentrated the reaction solution to about 5.0mL, and poured the residue into 100mL of ice water, stirred for 0.5h and then filtered, the filter cake was washed with H 2 O was washed and dried to give a yellow solid (2.8g, 93.1%), mp>270°C

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Abstract

The present invention relates to new quinolone compounds with excellent antiseptic activity and its preparation process, and antiseptic and feed additive containing the compounds. Specifically, the present invention is a new kind of quinolinecarboxylic acid derivative with amino radical in Place 5 of quinolone kernel, various cyclic amino substituent in Place 7 and methoxy radical in Place 8. Compared with available quinolone antiseptic with weak resisting activity to Gram-positive bacteria, the quinolinecarboxylic acid derivative has excellent resisting activity to Gram-positive bacteria and wide spectrum antiseptic activity.

Description

technical field [0001] The present invention relates to a new quinolone compound with excellent antibacterial activity and a preparation method thereof, and relates to an antibacterial pharmaceutical composition and a feed additive containing them. Background technique [0002] Quinolones were from nalidixic acid (nalidixic acid, see G.Y.Lesher et al., J.Med.Chem.5,1063-1065 (1962)) in 1962 to moxifloxacin (moxifloxacin) listed in 1999, Chinese patent disclosure NO. 1074218 (1993)), in terms of antibacterial activity, it has undergone a transition from being only effective against most Gram-negative bacteria to broad-spectrum antibacterial. [0003] According to the existing structure-activity relationship of quinolones, the 5-position substituent is NH 2 It can improve the activity of the compound against Gram-positive bacteria while reducing the phototoxicity of the compound. [0004] Sanchez J.P. etc. report in J.Med.Chem.1995,38,4478-4487: a series of 8-alkoxy groups a...

Claims

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Application Information

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IPC IPC(8): A61K9/02A61K9/06A61K9/08A61K31/4709A61K31/496C07D215/56C07D401/04C07D471/04C07D487/04
Inventor 郭慧元刘九雨王玉成
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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