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Fluoroquinolone acetal ftivazide as well as preparation method and application thereof

A fluoroquinolone aldehyde and quinolone aldehyde technology, which is applied in the field of fluoroquinolone derivative compounds, can solve the problems of poor tuberculosis efficacy, phototoxicity, and influence on animal cartilage development, etc., so as to reduce the probability of drug resistance, improve the inhibitory effect, and reduce toxicity. Effects of side effects

Inactive Publication Date: 2014-01-22
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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
Comparison scheme
Effect test

Embodiment 1

[0040] The fluoroquinolone aldehyde isoniazone of this embodiment is N′-[1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-quinoline(1H)-4-one-3-ylidene Methyl] isonicotinohydrazone, its chemical structure is:

[0041]

[0042] R in formula I 1 Is cyclopropyl, 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 Is a hydrogen atom.

[0043] The preparation method of the fluoroquinolone aldehyde isoniazone in this embodiment is: take 1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-3-formyl-4(1H)-quinoline 0.32g (1mmol) of ketone, 15ml of absolute ethanol, heat to dissolve, then add 0.14g (1mmol) of isoniazid and 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 isoniazone compound of Example 1, with a yield of 93%, m.p. 290-292°C. 1 HNMR(DMSO-d 6 , 400MHz) δ: 11.98 (s, 1H, CONH), 8.77 (s, 1H, C 2 -H), 8.75(d, J=8.7Hz...

Embodiment 2

[0045] The fluoroquinolone aldehyde isoniazone in this embodiment is N′-[1-ethyl6-fluoro-7-piperazin-1-yl-quinoline(1H)-4-one-3-methylene]iso Cigarette hydrazone, its chemical structure is:

[0046]

[0047] 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 Is a hydrogen atom.

[0048] The preparation method of the fluoroquinolone aldehyde isoniazone in this embodiment is: take 1-ethyl-6-fluoro-7-(piperazin-1-yl)-3-formyl-4(1H)-quinolinone 0.31g (1mmol), 15ml of absolute ethanol, heat to dissolve, then add isoniazid 0.14g (1mmol), reflux for 4h. 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, 400MHz) δ: 8.88~8.90 (m, 3H, C 2 -Handpyridine-H), 8.82(s, 1H, N=CH), 8.12(d, J=6.4Hz, 2H, pyridine-H), 8...

Embodiment 3

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

[0051]

[0052] R in formula I 1 Is cyclopropyl, 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 Is a hydrogen atom.

[0053] The preparation method of the fluoroquinolone aldehyde isoniazone in this embodiment is: take 1-cyclopropyl-6-fluoro-7-(4-ethylpiperazin-1-yl)-3-formyl-4(1H )-Quinolinone 0.34g (1mmol), 15ml of absolute ethanol, heated to dissolve, then add isoniazid 0.14g (1mmol), reflux for 4h. Placed overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.38 g of the fluoroquinolone isonicotinohydrazone 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: 8.83~8.86 (m, 3H, C 2 -Handpyridine-H), 8.75(s, 1H, N=CH), 8.06(d, J...

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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 isoniazone condensate, and also relates to a preparation method of the fluoroquinolone aldehyde isoniazone 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 worldwide have been infected with tuberculosis and about 1.5 million people have died of tuberculosis infection. At present, tuberculosis is an infectious disease with the highest mortality rate except AIDS. Due to the long clinical development process of anti-tuberculosis drugs, it is difficult to discover active new compounds and develop them into clinically promising anti-tuberculosis drugs. Since the advent of rifampicin, there has not been a new compound used for anti-tuberculosis treatment in the 40 years. In addition, the irrational use of drugs and incomplete treat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D401/14C07D471/04A61K31/4709A61K31/496A61P31/06
Inventor 胡国强杜耀武陶志敏王锐胡海廷王国强敬永升
Owner HENAN UNIVERSITY
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