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Nitroimidazole derivative as well as preparation method and application thereof

An alkyl and group technology, applied in the field of new nitroimidazoles, infection-related diseases, can solve problems such as difficult research, and achieve the effect of safety advantages

Pending Publication Date: 2021-10-22
NANJING CHANGAO PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

We have conducted systematic research on this target drug and achieved good results (patent publication number: CN105732659A). However, when the representative compound was subjected to toxicological experiments, the PK-PD study showed that the representative compound had a "capping" phenomenon, and it was difficult to further study. research, and the efficacy in mice did not exceed that of PA-824

Method used

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  • Nitroimidazole derivative as well as preparation method and application thereof
  • Nitroimidazole derivative as well as preparation method and application thereof
  • Nitroimidazole derivative as well as preparation method and application thereof

Examples

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preparation example Construction

[0066] The preparation method of anti-tuberculosis antibacterial compound of the present invention, its process can comprise:

[0067] Process 1: Process when X=O

[0068] In the first step, the compound with the structure shown in Formula I-5 is reduced to obtain the compound with the structure shown in Formula I-6;

[0069] In the second step, the compound shown in the formula I-6 is chlorinated to obtain the compound shown in the formula I-7;

[0070] The third step is to mix the compound with the structure of formula I-7 and the compound with the structure of formula I-8, and react to obtain the compound with the structure of formula I.

[0071] The reduction reaction of the above-mentioned first step can be selected to be carried out in a suitable solvent, and a suitable reducing agent is used; the solvent includes but not limited to, alcohols such as methanol, ethanol, ethers such as tetrahydrofuran, etc.; the reducing agent used includes But not limited to, sodium bor...

Embodiment 1

[0145] Example 1: (S)-N-methyl-5-(((2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6 -yl)oxy)methyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine (compound 1)

[0146]

[0147] (1) 4-trifluoromethoxyaniline (26.7g, 0.15mol), 5-bromo-2-chloropyrimidine (19.34g, 0.1mmol), DIPEA (25.85g, 0.2mol) were dissolved in n-butanol ( 180 mL), stirred overnight at 120°C. TLC detection (petroleum ether: ethyl acetate = 10:1), after the reaction was completed, the reaction solution was spin-dried, a small amount of dichloromethane was added to dissolve the concentrate, petroleum ether was added dropwise, and the solid was precipitated, and a light yellow solid 1-1 (13.85 g, yield: 42%).

[0148] 1 H-NMR (400MHz, CDCl 3 )δ8.44(s,2H),7.66-7.56(m,2H),7.37(s,1H),7.24-7.15(m,2H).ESI-Ms:233.9[M+1]+.

[0149] (2) Dissolve 1-1 (6.68g, 20mmol) in dry DMF (70mL), add NaH (1.2g, 30mmol) to it under argon protection under ice-cooling, stir for 30min under ice-cooling, and then add Iodomet...

Embodiment 2

[0159] Example 2: (S)-N-ethyl-5-(((2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6 -yl)oxy)methyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine (compound 2)

[0160]

[0161] Compound 2 was prepared by the same method as in Example 1.

[0162] 1 H-NMR (400MHz, CDCl 3 )δ8.20(s, 2H), 7.33(s, 1H), 7.19(s, 4H), 4.55(d, J=11.8Hz, 1H), 4.49(d, J=11.6Hz, 1H), 4.38( d,J=11.3Hz,1H),4.29(d,J=12.2Hz,1H),4.15(dd,J=13.6,4.8Hz,1H),4.08-4.03(t,J=8.5Hz,2H), 3.95(q, J=6.9Hz, 2H), 1.15(t, J=6.9Hz, 3H).ESI-Ms: 481.1[M+1] + .

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Abstract

The invention discloses a nitroimidazole derivative as well as a preparation method and application thereof. The compounds have the following general formula (I).

Description

technical field [0001] The invention belongs to the fields of pharmacology, medicinal chemistry and pharmacology, and more specifically, relates to a class of novel nitroimidazole compounds, a preparation method thereof, and the use of such compounds for treating diseases related to infection caused by Mycobacterium tuberculosis . Background technique [0002] Tuberculosis is caused by Mycobacterium tuberculosis infection and is one of the oldest human diseases. Up to now, tuberculosis still seriously endangers human health. According to WHO statistics, about 1 / 3 of the world's people have been infected with Mycobacterium tuberculosis, and tuberculosis is the infectious disease that causes the largest number of deaths (higher than HIV). [0003] According to the "Global Tuberculosis Report 2019" released by the World Health Organization (WHO), there were about 10 million new tuberculosis patients worldwide in 2018, and the number of patients has been relatively stable in re...

Claims

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Application Information

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IPC IPC(8): C07D498/04A61K31/506A61P31/06
CPCC07D498/04A61P31/06A61K31/506A61K31/5365
Inventor 赵传生向军刘广才董吉宋海峰
Owner NANJING CHANGAO PHARMA SCI & TECH CO LTD
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