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2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound, preparation method therefor and use of 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound

A technology of compounds and substituents, applied in the field of medicine, can solve problems such as adverse reactions of patients, difficulty in regular drug use, threats to tuberculosis prevention and control, etc.

Active Publication Date: 2018-12-07
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, long-term drug combination therapy causes adverse reactions in patients, and it is difficult to adhere to regular drug use. In addition, the incidence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) has been on the rise in recent years, posing a serious threat global tuberculosis control

Method used

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  • 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound, preparation method therefor and use of 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound
  • 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound, preparation method therefor and use of 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound
  • 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound, preparation method therefor and use of 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound

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Experimental program
Comparison scheme
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specific Embodiment approach

[0078] The present invention can be described in detail by the following examples, but it does not imply any adverse limitation on the present invention. The present invention has been described in detail herein, and its specific embodiments are also disclosed. For those skilled in the art, it is necessary to make various changes and improvements to the specific embodiments of the present invention without departing from the spirit and scope of the present invention. Obvious.

[0079] For all of the following examples, standard manipulations and purification methods known to those skilled in the art can be used. All temperatures are in °C (degrees Celsius) unless otherwise indicated. The structures of the compounds were determined by nuclear magnetic resonance spectroscopy (NMR).

[0080] Preparation of the Example section

[0081] The structure of the compound was obtained by H NMR spectroscopy ( 1 H NMR) to determine. Proton and Carbon NMR shifts (δ) are given in part...

Embodiment 1

[0096]

[0097] 2-((Phenyl)amino)-6-trifluoromethyl-8-nitro-chromen-4-one

[0098] route:

[0099]

[0100] Experimental steps:

[0101] Preparation of the first step 3-(2-chloro-3-nitro-5-(trifluoromethyl)phenyl)-3-oxo-N-phenylpropanamide B-1

[0102] In a 25mL reaction bottle, the compound 3-(2-chloro-3-nitro-5-(trifluoromethyl)phenyl)-3-oxopropionic acid A (311mg, 1.0mmol), DCC (201mg, 1.0 mmol) was dissolved in dry dichloromethane (5 mL), protected by Ar, aniline (93 mg, 1.0 mmol) was added, and stirred at room temperature for 12 hours. The insoluble solids were filtered off, concentrated, and separated by silica gel (200-300 mesh) column chromatography, using ethyl acetate-petroleum ether (V:V=5-15:100) mixture as the eluent. Intermediate B-1 was obtained, 218 mg of light yellow solid, yield 56.5%.

[0103] 1 H NMR (400MHz, CDCl 3 )δ: 14.19(s, 1H), 8.05(d, J=8.4Hz, 2H), 7.54(d, J=7.6Hz, 2H), 7.38(t, J=7.6Hz, 2H), 7.18(t, J=7.6Hz,1H),7.11(brs,1H),5.57(s,1H). ...

Embodiment 2

[0108]

[0109] 2-(((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)(methyl)amino)-6-trifluoromethyl-8 -Nitro-benzopyran-4-one

[0110] route:

[0111]

[0112] Experimental steps:

[0113] The first step 3-(2-chloro-3-nitro-5-trifluoromethylphenyl)-N-((2,3-dihydrobenzo[b][1,4]dioxane Preparation of En-6-yl)methyl)-N-methyl-3-oxopropionamide B-2

[0114] Using 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-methylmethylamine (179mg, 1.0mmol) as raw material, using the example The first step in 1 was similarly operated to obtain intermediate B-2, 285 mg of light yellow solid, with a yield of 60.3%.

[0115] 1 H NMR (400MHz, CDCl 3 )δ:15.57(m,1H),8.02(m,2H),6.86(m,1H),6.81(m,1H),6.70(m,1H),5.71(m,1H),4.50(m,2H ),4.26(m,4H),3.02(m,3H).

[0116] The second step 2-(((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)(methyl)amino)-6-trifluoromethane Preparation of yl-8-nitro-benzopyran-4-one II-2 (compound 2)

[0117] With 3-(2-chloro-3-nitro-5-trifluoromethylphenyl)-N-((2,3-dihydro...

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Abstract

The invention discloses a 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound represented by a formula (I) shown in the description, a preparation method therefor and application of the 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio-)pyran-4-one compound in drugs for treating and / or preventing infectious diseases induced by mycobacterium tuberculosis. Specifically, the invention relates to the compound represented by the formula (I) and pharmaceutically-acceptable salts thereof and a pharmaceutical composition containing the compound disclosed by the invention, wherein X, R1, R2 and n are as defined in the description. The invention aims at preparing a novel compound with the activity of resisting the mycobacterium tuberculosis; and as a potential new drug, the compound can be applied to the treatment or prophylactic treatment of microbial infectious diseases, particularly pulmonary tuberculosis (TB) induced by mycobacteria, and meanwhile, the compound can be used for overcoming problems related to drug resistance of the mycobacterium tuberculosis.

Description

technical field [0001] The invention belongs to the technical field of medicine. In particular, it relates to 2-substituted amino-5-trifluoromethyl-8-nitrobenzo(thio)pyran-4-one compounds represented by the general formula (I), and its preparation method uses the compound as an active Pharmaceutical compositions of ingredients, and their use in the treatment and / or prevention of infectious diseases caused by Mycobacterium tuberculosis. Background technique [0002] Tuberculosis (TB) is a chronic fatal disease caused by Mycobacterium tuberculosis. It is a major infectious disease that endangers human health and causes human death. There were more than 10 million tuberculosis cases and 1.5 million deaths. Tuberculosis is now one of the leading causes of death worldwide, along with AIDS. Chemotherapy is the mainstay of tuberculosis treatment. With the emergence of isoniazid, rifampicin, and pyrazinamide, the treatment of tuberculosis has entered the "short-course chemothera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22C07D407/12C07D335/06C07D409/12C07D417/12A61K31/352A61K31/357A61K31/382A61K31/4439A61K31/427A61P31/06
CPCC07D311/22C07D335/06C07D407/12C07D409/12C07D417/12
Inventor 黄海洪李鹏李刚
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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