Fibric acid compounds and medical uses thereof

A technology of compounds and hydrates, applied in the field of medicine, can solve problems such as threats to health and life safety

Active Publication Date: 2020-03-03
青岛睿森生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, currently available drugs for metabolic diseases are limited by some important drawbacks, and some important metabolic diseases such as steatohepatitis have no approved treatment drugs, and the complications of these metabolic diseases seriously threaten For health and life safety, it is urgent to find new drugs for the treatment of metabolic diseases and preventive drugs for complications of metabolic diseases

Method used

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  • Fibric acid compounds and medical uses thereof
  • Fibric acid compounds and medical uses thereof
  • Fibric acid compounds and medical uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0402] Example 1: Preparation of 5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (BJMU-1)

[0403]

[0404] Step 1: Preparation of isobutyl 5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoate (Int 1)

[0405] Compound 1-1 (4-chloro-2,5-dimethylphenol) (780mg, 5.0mmol), 5-chloro-2,2-dimethylvaleric acid isobutyl ester (1144mg, 5.2mmol), TBAI (36.9mg, 0.1mmol), potassium carbonate (1380mg, 10.0mmol) were dissolved in DMF (30mL), stirred overnight at 90 degrees Celsius, TLC monitored the trend of continuous conversion, the reaction solution was poured into water, separated, and the aqueous phase After extraction with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated, and the crude product was separated by silica gel column chromatography to obtain compound 1-2 (1.5 g), with a yield of 88%.

[0406] The second step: the preparation of 5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpent...

Embodiment 2

[0409] Example 2: Preparation of 5-(4-bromo-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (BJMU-2)

[0410]

[0411] In the first step in Example 2, compound 2-1 was used to replace the compound 1-1 in the first step in Example 1. The compound BJMU-2 was synthesized by the similar method described in the first step to the second step of Example 1, and the two-step yield was 66%.

[0412] 1 H NMR (400MHz, Chloroform-d) δ7.25(s,1H),6.64(s,1H),3.90(t,J=5.9Hz,2H),2.33(s,3H),2.15(s,3H) ,1.91–1.58(m,4H),1.25(s,6H). 13 C NMR (101MHz, CDCl3) δ184.38, 156.20, 135.57, 133.65, 126.29, 114.58, 113.47, 68.23, 41.94, 36.78, 25.04, 24.98, 22.87, 15.44

Embodiment 3

[0413] Example 3: Preparation of 5-(4-fluoro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (BJMU-3)

[0414]

[0415] In the first step in Example 3, compound 3-1 was used to replace the compound 1-1 in the first step in Example 1. The compound BJMU-3 was synthesized by the similar method described in the first step to the second step of Example 1, and the two-step yield was 78%.

[0416] 1 H NMR (400MHz, CDCl3) δ6.78 (d, J = 9.8Hz, 1H), δ6.56 (d, J = 7.0 Hz, 1H), δ3.89 (t, J = 6.0Hz, 2H), δ2 .22(s,3H),δ2.17(s,3H),δ1.85–1.69 (m,4H),δ1.25(s,6H). 13 C NMR (101MHz, CDCl3) δ184.76, 155.12 (d, J = 236.3Hz), 152.72 (d, J = 2.15), 125.60 (d, J = 7.57), 121.61 (J = 18.4), 116.82 (d, J = 23.74), 113.78 (d, J=5.43), 68.69, 41.94, 36.81, 25.12, 24.94, 22.83, 15.41. 19 F NMR (376MHz, CDCl3), δ-129.00 (s, 1F)

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PUM

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Abstract

The invention belongs to the technical field of medicines, particularly relates to fibric acid compounds, pharmaceutically acceptable salts or esters, stereoisomers, prodrugs, hydrates, solvates, crystalline forms, metabolite forms, or any combinations or mixtures thereof, a pharmaceutical composition containing the compound, the pharmaceutically acceptable salt or ester, the stereoisomer, the prodrug, the hydrate, the solvate, the crystal form, the metabolite form or any combination or mixture, and medical uses of the compounds, the pharmaceutically acceptable salts or esters, the stereoisomers, the prodrugs, the hydrates, the solvates, the crystal forms, the metabolite forms or any combinations or mixtures thereof. For example, the compounds of the present invention can be used for preventing and / or treating metabolic diseases (such as metabolic syndrome, non-alcoholic fatty liver disease, and / or diabetes).

Description

technical field [0001] The invention belongs to the technical field of medicine. In particular, the present invention relates to a phenoxy acid compound, a pharmaceutical composition containing the compound, and a medical application of the compound. For example, the compounds of the invention are useful in the prevention and / or treatment of metabolic diseases and complications of such diseases. Background technique [0002] With the development of society and economy, the incidence of metabolic diseases such as diabetes, obesity, fatty liver disease, and metabolic syndrome continues to rise. These diseases are not only related to each other, but also lead to a variety of serious complications and a significant increase in the risk of other major diseases such as cancer, cardiovascular and cerebrovascular diseases, etc., and have become one of the greatest threats to human health. [0003] Despite the long-term research on the pathogenesis and treatment of metabolic diseas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/125C07C205/37C07C255/13A61K31/19A61K31/275A61P3/10A61P3/04A61P9/12A61P9/10A61P3/06A61P29/00A61P39/06A61P3/00A61P1/16A61P5/48A61P27/02A61P25/00A61P13/12A61P17/02A61P9/00
CPCC07C59/125C07C205/37C07C255/13A61P3/10A61P3/04A61P9/12A61P9/10A61P3/06A61P29/00A61P39/06A61P3/00A61P1/16A61P5/48A61P27/02A61P25/00A61P13/12A61P17/02A61P9/00A61K31/275C07C59/68A61K31/192A61K45/06C07C59/13
Inventor 焦宁余四旺宋颂刘雅萌杨思敏
Owner 青岛睿森生物科技有限公司
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