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Fluoroquinolone acetal ftivazide as well as preparation method and application thereof

A technology of fluoroquinolone aldehyde and quinolone aldehyde, which is applied in the field of fluoroquinolone derivative compounds, can solve the problems of affecting animal cartilage development, poor efficacy of tuberculosis, and phototoxicity, and achieves the reduction of the probability of drug resistance, better inhibition, and lower toxicity. side effects

Inactive Publication Date: 2012-12-19
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because fluoroquinolones (FQs) affect cartilage development in animals, have phototoxicity, and are less effective against tuberculosis than classic first-line anti-tuberculosis drugs such as isoniazid (INH) and rifampicin (RFP), so this class Drugs have certain defects in the treatment of tuberculosis
However, isoniazid is an anti-tuberculosis drug that has a strong killing effect on Mycobacterium tuberculosis, but it has certain liver toxicity.

Method used

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  • Fluoroquinolone acetal ftivazide as well as preparation method and application thereof
  • Fluoroquinolone acetal ftivazide as well as preparation method and application thereof
  • Fluoroquinolone acetal ftivazide as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0040] The fluoroquinolone aldehyde isonicotinoid hydrazone in this embodiment is N'-[1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-quinolin(1H)-4-one-3-ylidene Methyl] isonicotinoid hydrazone, its chemical structural formula is:

[0041]

[0042] That is, R in formula I 1 is cyclopropanyl, R 2 is a hydrogen atom, X is a carbon atom, Y is a hydrogen atom, Z is a substituent 1, R 3 is a hydrogen atom, R 4 for a hydrogen atom.

[0043] The preparation method of the fluoroquinolone aldehyde isonicotinoid hydrazone of the present embodiment is: take 1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-3-formyl-4(1H)-quinoline Ketone 0.32g (1mmol), absolute ethanol 15ml, heated to dissolve, then add isoniazid 0.14g (1mmol), reflux for 5h. After standing overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.4 g of the fluoroquinolone isoniadrazone compound of Example 1, with a yield of 93%, m.p.290-292°C. 1 HNMR (DMSO-d 6 , 400MHz...

Embodiment 2

[0045] The fluoroquinolone aldehyde abbreviated isonicotidine hydrazone in this embodiment is N'-[1-ethyl 6-fluoro-7-piperazin-1-yl-quinolin(1H)-4-one-3-methylene]iso Nicotinic hydrazone, its chemical structural formula is:

[0046]

[0047] That is, R in formula I 1 is ethyl, R 2 is a hydrogen atom, X is a carbon atom, Y is a hydrogen atom, Z is a substituent 1, R 3 is a hydrogen atom, R 4 for a hydrogen atom.

[0048]The preparation method of the fluoroquinolone aldehyde isoniazone acetal in this embodiment is as follows: take 1-ethyl-6-fluoro-7-(piperazine-1-yl)-3-formyl-4(1H)-quinolinone 0.31 g (1 mmol), 15 ml of absolute ethanol, heated to dissolve, then 0.14 g (1 mmol) of isoniazid was added, and refluxed for 4 h. After standing overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.35 g of the fluoroquinolone isoniazone compound of Example 2, with a yield of 83%, m.p. 166-169°C. 1 HNMR(CD 3 CO 2 D, 400M...

Embodiment 3

[0050] The fluoroquinolone aldehyde isonazone acetal in this embodiment is N'-[1-cyclopropyl-[6-fluoro-7-(4-ethylpiperazin-1-yl)-quinoline(1H)-4- Keto-3-methylene]isoniazone, its chemical structural formula is:

[0051]

[0052] That is, R in formula I 1 is cyclopropane, R 2 is a hydrogen atom, X is a carbon atom, Y is a hydrogen atom, Z is a substituent 1, R 3 is ethyl, R 4 for the hydrogen atom.

[0053] The preparation method of the fluoroquinolone aldehyde isoniazid acetal in this embodiment is as follows: take 1-cyclopropyl-6-fluoro-7-(4-ethylpiperazine-1-yl)-3-formyl-4(1H )-quinolinone 0.34g (1mmol), 15ml of absolute ethanol, heated to dissolve, then added isoniazid 0.14g (1mmol), refluxed for 4h. After standing overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.38 g of the fluoroquinolone isoniazone compound of Example 3, with a yield of 83%, m.p. 281.8-283.6°C. 1 HNMR(CD 3 CO 2 D, 400MHz) δ: 8.83~8...

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Abstract

The invention discloses a fluoroquinolone acetal ftivazide. According to the fluoroquinolone acetal ftivazide, fluoroquinolone aldehyde and isoniazide are combined to form a hydrazones compound which has a chemical structure shown as the following chemical structural formula in the specification. The fluoroquinolone acetal ftivazide achieves the parataxis of fluoroquinolone and isoniazide antituberculous medicines, and reduces the toxic and side effects of the two, and reduces the probability of the generation of the resistance of mycobacterium tuberculosis to an antibacterial agent with double effects; and the fluoroquinolone can be used as a medicine active substance to develop a mycobacterium tuberculosis medicine with a brand new structure.

Description

technical field [0001] The invention relates to a fluoroquinolone derivative compound, in particular to a fluoroquinolone aldehyde isonicotidine hydrazone, a preparation method of the fluoroquinolone aldehyde isonicotidine hydrazone, and its application in anti-tuberculosis drugs. Background technique [0002] Tuberculosis is a major threat to human health. At present, more than 10 million people in the world have been infected with tuberculosis, and about 1.5 million people have died of tuberculosis infection. Currently, tuberculosis is the infectious disease with the highest mortality rate except AIDS. Due to the long clinical development process of anti-tuberculosis drugs, it is difficult to find active new compounds and develop them into clinically promising anti-tuberculosis drugs. In the 40 years since the advent of rifampicin, no new compound has been used for anti-tuberculosis treatment. In addition, irrational drug use and incomplete treatment make the infection ra...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D401/14C07D471/04A61K31/4709A61K31/496A61P31/06
Inventor 胡国强王国强敬永升
Owner HENAN UNIVERSITY
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