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A kind of preparation method of nitroimidazopyran anti-tuberculosis drug

A nitroimidazopyran, anti-tuberculosis technology, applied in the directions of antibacterial drugs, pharmaceutical formulations, chemical instruments and methods, can solve the problems of high price, unfavorable for industrialized production, etc., and achieves reduction of production costs and ease of scale. Mild effects of preparation and reaction conditions

Active Publication Date: 2021-03-05
SHENYANG PHARMA UNIVERSITY
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Problems solved by technology

The preparation method of PA-824 provided in these documents is to use 2,4-dinitroimidazole and (S)-tert-butyldimethylsilyl glycidyl ether as starting materials to prepare PA-824, explosive The use of 2,4-dinitroimidazole and expensive (S)-tert-butyldimethylsilyl glycidyl ether is not conducive to industrial production

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  • A kind of preparation method of nitroimidazopyran anti-tuberculosis drug
  • A kind of preparation method of nitroimidazopyran anti-tuberculosis drug
  • A kind of preparation method of nitroimidazopyran anti-tuberculosis drug

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Embodiment Construction

[0022] The above content of the present invention will be further described in detail through the description of specific embodiments below. For those skilled in the art, it should not be understood that the scope of the above subject matter of the present invention is limited to the following method description; all technologies realized based on the above contents of the present invention belong to the scope of the present invention.

[0023] 1. Synthesis of (S)-1-chloro-3-(2-chloro-4-nitro-1H-imidazol-1-yl)propan-2-ol (4)

[0024] 2-Chloro-4-nitroimidazole (30.0g, 203.36mmol) and 210mL (S)-epichlorohydrin were added to a 500mL three-necked flask, 8.4g (61.01mmol) of potassium carbonate was added, and the temperature was raised to After reacting at 70°C for 30 min, TLC detected that the raw material spot disappeared. After cooling to room temperature and filtering, the filtrate was concentrated under reduced pressure to 100 mL, filtered to obtain white crystals, the filtrat...

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Abstract

The invention relates to a preparation method of a nitroimidazole pyran antituberculotic candidate drug PA-824. The method comprises five reaction steps, and specially comprises the following steps: firstly, carrying out nucleophilic substitution, hydrolysis and silylation to obtain a key intermediate 6, and then carrying out O-alkylation and cyclization to obtain a final product that is the PA-824. Raw materials required by the whole reaction are cheap and easily available, the use of explosive raw material 2,4-dinitroimidazole is avoided, the reaction conditions are mild, and the method is simple to operate and prone to large-scale production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a preparation method of a nitroimidazole pyran anti-tuberculosis drug (PA-824), more specifically to Oxygen)-3-(2-chloro-4-nitro-1H-imidazol-1-yl)propan-2-ol (6) Preparation method of PA-824 as key intermediate. Background technique [0002] Pretomanid(1), light yellow crystalline powder, molecular formula: C 13 h 12 N 3 o 5 f 3 , Molecular weight: 359.26. PA-824 is a nitroimidazole pyran compound, which mainly inhibits Mycobacterium tuberculosis through the dual mechanism of inhibiting bacterial protein synthesis and cell wall mycolic acid synthesis. The antibacterial activity is better than isoniazid, and it has better activity against sensitive tuberculosis and rifampicin-resistant tuberculosis. It has potential curative effect on isolated multidrug-resistant tuberculosis (MDR-TB), and it is possible to shorten the treatment cycle, which is comparable to clinical use ...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04C07F7/18A61P31/06A61K31/5365
CPCA61P31/06C07D498/04C07F7/1804C07F7/188
Inventor 翟鑫苗秀旗郭明宫平姜楠陈国军
Owner SHENYANG PHARMA UNIVERSITY