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Hybrid molecules qa, wherein q is an aminoquinoline and a is an antibiotic or a resistance enzyme inhibitor, their synthesis and their uses as antibacterial agent

An aminoquinoline and antibiotic technology, applied to a hybrid QA molecule in which Q is an aminoquinoline and A is an antibiotic residue, which can solve the problem of not showing the special activity of the aminoquinoline substituent.

Inactive Publication Date: 2007-11-07
PALUMED +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the aromatic moieties disclosed in these documents for conjugation to antibiotics are very broad and do not show specific activity of aminoquinoline substituents.

Method used

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  • Hybrid molecules qa, wherein q is an aminoquinoline and a is an antibiotic or a resistance enzyme inhibitor, their synthesis and their uses as antibacterial agent
  • Hybrid molecules qa, wherein q is an aminoquinoline and a is an antibiotic or a resistance enzyme inhibitor, their synthesis and their uses as antibacterial agent
  • Hybrid molecules qa, wherein q is an aminoquinoline and a is an antibiotic or a resistance enzyme inhibitor, their synthesis and their uses as antibacterial agent

Examples

Experimental program
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preparation example Construction

[0029] The invention also relates to processes for their preparation, to their various uses, to pharmaceutical compositions containing them, and to methods of therapeutic treatment. These new molecules could also be used as antimicrobial agents.

[0030] According to a first aspect, the present invention provides hybrid aminoquinoline-antibiotic compounds, characterized in that they have the following general formula (I):

[0031] Q-(Y 1 ) p -(U) p’ -(Y 2 ) p” -A (I)

[0032] in:

[0033] -Q represents an aminoquinoline having the following formula (IIa), (IIb), (IIIa), (IIIb), (IIIc) or (IIId):

[0034]

[0035] In the above formula:

[0036] - symbol Indicates other fragments, such as Y 1 , or U, or Y 2 , or a fixed bit of A;

[0037] - n and n' represent 0, 1, 2 or 3 independently of each other;

[0038] -R 1a and R 1b denotes the same or different substituent(s) occupying any position and denotes a substituent selected from the group cons...

Embodiment 1-4

[0505] Examples 1-4 below illustrate the preparation of hybrid molecules of the quinoline-penicillin family

Embodiment 1

[0506] Embodiment 1: the preparation of quinoline-penicillin, reference number PA 1007

[0507] (2S, 5R, 6R)-6-{[1-(7-chloro-quinolin-4-yl)-piperidine-4-carbonyl]-amino}-3,3-dimethyl-7-oxo - 2,2-dimethyl-propionyloxymethyl 4-thio-1-aza-bicyclo[3.2.0]heptane-2-carboxylate.

[0508]

[0509] 1.1. 1-(7-Chloro-quinolin-4-yl)-piperidine-4-carboxylic acid.

[0510] A mixture of 4,7-dichloroquinoline (17.4 g, 0.09 mol), isonipecotic acid (23.8 g, 0.18 mol) and phenol (46.3 g, 0.49 mol) was heated at 120°C under magnetic stirring for 24 hours. After returning to room temperature, the reaction medium is diluted with 400 ml of ethyl acetate, filtered through sintered glass and the resulting precipitate is washed with water. Next, the precipitate was recrystallized by thermal dissolution (100° C.) in 300 ml of 10% (w / v) carbonate-containing water and precipitated at 0° C. by adding 2M aqueous hydrochloric acid until pH 5. The precipitate formed was filtered off, washed successively...

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PUM

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Abstract

The invention concerns an aminoquinoline-antibiotic hybrid compound of general formula (I): Q-(Y1)p-(U)p'-(Y2)p''-A; wherein Q represents an aminoquinoline, (Y1)p-(U)p'-(Y2)p'' is an optional spacer and A is an antibiotic residue. The invention enables the antibiotic residue activity to be unexpectedly enhanced.

Description

technical field [0001] The object of the present invention is a hybrid molecule "OA" comprising an aminoquinoline moiety (Q) covalently linked to an antibiotic residue (A). The invention also relates to their synthesis and their use as antibacterial agents. Background technique [0002] The introduction of penicillin and subsequently many other antimicrobial agents over the past 50 years represents one of the greatest successes of modern medicine in the treatment of bacterial infections (Greenwood, D et al., antimicrobial Chemotherapy; Greenwood, D., Ed.; Oxford University Press: New York , United States, 2000). The emergence and multiplication of bacterial strains resistant to virtually all antimicrobial agents currently in existence is becoming a serious public health problem (World Health Organization. Anti-microbial resistance: a gobal threat. Essential drugs: Monitor, 2000, 28 and 29, 1-35. Accessible on www.who.int ). [0003] The problem of bacterial resistance wa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/76C07D499/48C07D499/54C07D499/64C07D501/00C07D501/34A61P31/04C07D215/56C07D401/12C07D401/14A61K31/4709C07K5/00C07D499/00
CPCC07K5/0806C07K5/0827C07D401/12C07K5/0202C07K9/008C07K7/06C07K5/0205C07K7/08C07K5/06182C07D215/56C07D401/14A61P31/00A61P31/04
Inventor M·桑切斯B·默尼耶
Owner PALUMED
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