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Salt of benzothiopyrone compound and preparation method and use thereof

A technology of benzothiopyran and citrate, which is applied in the field of medicine and can solve problems such as undisclosed specific examples and experimental results

Active Publication Date: 2022-07-22
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Patent 201810092333.X and PCT / CN2018 / 080787 disclose 2-(4-(cyclohexylmethyl)piperazin-1-yl)-6-(trifluoromethyl)-8-nitro-benzothiopyr Examples of pyran-4-one and its hydrochloride, but did not disclose specific examples and experimental results of other pharmaceutically acceptable salts

Method used

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  • Salt of benzothiopyrone compound and preparation method and use thereof
  • Salt of benzothiopyrone compound and preparation method and use thereof
  • Salt of benzothiopyrone compound and preparation method and use thereof

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specific Embodiment approach

[0045] The present invention can be described in detail by the following examples, but does not imply any unfavorable limitation of the present invention. The present invention has been described in detail herein, and the specific embodiments thereof have also been disclosed. For those skilled in the art, various changes and modifications can be made to the specific embodiments of the present invention without departing from the spirit and scope of the invention. Obvious.

[0046] For all of the following examples, standard procedures and purification methods known to those skilled in the art can be used. All temperatures are expressed in °C (degrees Celsius) unless otherwise stated. The structures of the compounds were determined by nuclear magnetic resonance spectroscopy (NMR).

[0047] Preparation Examples Section

[0048] The structures of the compounds were determined by H NMR spectroscopy ( 1 H NMR) to determine. 1H NMR chemical shifts (δ) are given in parts per m...

Embodiment 1

[0072]

[0073]2-(4-(Cyclohexylmethyl)piperazin-1-yl)-6-(trifluoromethyl)-8-nitro-benzothiopyran-4-one·1maleate ( Compound 1)

[0074] synthetic route:

[0075]

[0076] Compound (I) (1.14g, 2.5mmol) was added into a 100mL there-necked flask, 21mL of anhydrous methanol was added, stirred at room temperature, maleic acid (0.348g, 3.0mmol) was slowly added at room temperature, after adding 2-3min, the solution A yellow solid started to precipitate, and after stirring at room temperature for 3 hours, suction filtration, the filter cake was rinsed with 5 mL of methanol, and dried to obtain 1.23 g of a yellow powdery solid, yield: 86%.

[0077] 1 H NMR (400MHz, CD 3 OD)δ: 9.02(d,J=2.2Hz,1H),8.90(d,J=2.2Hz,1H),6.40(s,1H),6.27(s,2H),3.98(brs,4H),3.32 (brs,4H),2.94-2.92(m,2H),1.86-1.79(m,5H),1.76-1.72(m,1H),1.39-1.21(m,3H),1.12-1.03(m,2H) .

Embodiment 2

[0079]

[0080] 2-(4-(Cyclohexylmethyl)piperazin-1-yl)-6-(trifluoromethyl)-8-nitro-benzothiopyran-4-one 3 / 2 fumaric acid Salt (compound 2)

[0081] synthetic route:

[0082]

[0083] Compound (I) (0.228g, 0.5mmol) was added to a 25mL single-necked flask, 6mL of anhydrous methanol was added, stirred at room temperature, and fumaric acid (0.232g, 2.0mmol) was added, and after the addition, kept 80°C under reflux and stirred for 3 After 1 hour, it was naturally cooled to room temperature, filtered with suction after ice bath for 10 min, the filter cake was rinsed with 1 mL of methanol, and dried to obtain 0.25 g of a yellow powdery solid, yield: 79%.

[0084] 1 H NMR (400MHz, DMSO-d 6 )δ: 13.08(brs, 2H), 8.85-8.83(m, 2H), 6.62(s, 3H), 6.30(s, 1H), 3.66-3.64(m, 4H), 2.48(brs, 4H), 2.16 -2.14(m,2H),1.76-1.65(m,5H),1.54-1.48(m,1H),1.27-1.12(m,3H),0.90-0.82(m,2H).

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Abstract

The invention discloses salts of benzothiopyrone compounds, specifically 2-(4-(cyclohexylmethyl)piperazine-1-yl)-6-(trifluoromethyl) represented by formula (I). base)-8-nitro-benzothiopyran-4-ketone salt, preparation method thereof and application in medicine for treating and / or preventing infectious diseases caused by Mycobacterium tuberculosis. In particular, the present invention relates to pharmaceutically acceptable salts of formula (I) and pharmaceutical compositions comprising the compounds of the present invention. The invention aims to prepare a kind of 2-(4-(cyclohexylmethyl)piperazine-1-yl)-6-(trifluoromethyl) with significantly improved pharmacokinetic properties and physicochemical properties and strong anti-mycobacterium tuberculosis activity base)-8-nitro-benzothiopyran-4-one as a potential new drug for infectious diseases caused by bacteria, especially pulmonary tuberculosis (TB) caused by Mycobacterium tuberculosis ) disease treatment or prophylactic treatment, and can be used to overcome problems associated with drug resistance in Mycobacterium tuberculosis.

Description

technical field [0001] The invention belongs to the technical field of medicine. In particular, it relates to salts of benzothiopyrones: 2-(4-(cyclohexylmethyl)piperazin-1-yl)-6-(trifluoromethyl)-8 represented by formula (I) - Salts of nitro-benzothiopyran-4-ones, methods for their preparation, pharmaceutical compositions using the salts as active ingredients, and their use in the treatment and / or prevention of infectious diseases caused by Mycobacterium tuberculosis applications in . Background technique [0002] Tuberculosis (TB) is a chronic lethal disease caused by Mycobacterium tuberculosis, which is a major infectious disease that endangers human health and causes human death. According to WHO estimates, there were about 1.7 billion people with latent tuberculosis infection in the world in 2017, and the latent infection rate was 23%. There are about 10 million new tuberculosis patients worldwide, and about 1.4 million deaths. The incidence of tuberculosis is 133 / 100...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D335/04A61K31/496A61P31/06
CPCC07D335/04A61P31/06A61K31/496A61K31/4535
Inventor 李刚黄海洪李鹏马辰张婷婷王宝莲李燕
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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