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Oxazolidinone derivatives as PPAR ligands

A technology of oxazolidine and alkyl, applied in the field of oxazolidinone derivatives used as PPAR ligands, can solve problems such as liver damage

Inactive Publication Date: 2016-08-24
セルビシオアンダルーサデサルー +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In addition, certain chemicals that act as PPAR gamma agonists have been documented to cause liver damage and must be used with caution, evaluating their benefits and side effects

Method used

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  • Oxazolidinone derivatives as PPAR ligands
  • Oxazolidinone derivatives as PPAR ligands
  • Oxazolidinone derivatives as PPAR ligands

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0157] Embodiment 1. Preparation of (R)-3-((4-benzyl-2-oxooxazolidin-3-yl)methyl)-N-(4-((4-( tert-butyl)benzyl)carbamoyl)phenyl)benzamide (1)

[0158]

[0159] in N 2 Under the atmosphere, take the Al(CH 3 ) 3 2.0 M heptane (0.18 mL, 0.36 mmol) was added to (R)-methyl 3-((4-benzyl-2-oxooxazolidin-3-yl)methyl)benzoate (0.06 g , 0.18 mmol) and compound 4-amino-N-(4-(tert-butyl)benzyl)benzamide (0.10 g, 0.36 mmol); the reaction mixture was heated at 125°C in a microwave reactor 35 minutes. The crude reaction product was cooled in an ice-water mixture and acidified with HCl (1N) until effervescence ceased. Then, it was extracted with diethyl ether (20 mL), and the organic extract was washed with anhydrous MgSO 4 Dry, and remove the solvent under reduced pressure. The crude reaction product was purified by biotage chromatography (Hex / AcOEt) to afford compound 1 as a white solid (0.05 g, 44%). 1 H NMR (300MHz, CDCl 3 )δ8.91(s,1H,NH),7.83(m,1H),7.78–7.63(m,5H),7.44–7.15(m...

Embodiment 2

[0168]Example 2. Preparation of (R)-3-((4-benzyl-2-oxooxazolidin-3-yl)methyl)-N-(4-((4-( Trifluoromethyl)benzyl)carbamoyl)phenyl)benzamide (2)

[0169]

[0170] in N 2 Under the atmosphere, take the Al(CH 3 ) 3 2.0 M heptane (0.30 mL, 0.61 mmol) was added to (R)-methyl 3-((4-benzyl-2-oxooxazolidin-3-yl)methyl)benzoate (0.10 g , 0.31 mmol) and 4-amino-N-(4-(trifluoromethyl)benzyl)benzamide (0.18 g, 0.61 mmol); the reaction mixture was heated at 125°C in a microwave reactor 35 minutes. The crude reaction product was cooled in an ice-water mixture and acidified with HCl (1N) until effervescence ceased. Then, it was extracted with diethyl ether (30ml), and the organic extract was washed with anhydrous MgSO 4 Dry, and remove the solvent under reduced pressure. The crude reaction product was purified by chromatography (6:4 hexane / ethyl acetate) to afford compound 2 as a white solid (0.05 g, 44%). 1 H NMR (300MHz, DMSO-d 6 )δ10.49(s,1H,NH),9.07(t,J=6.1Hz,1H,CH 2 NH ),7...

Embodiment 3

[0175] Example 3. Preparation of (R)-3-((4-benzyl-2-oxooxazolidin-3-yl)methyl)-N-(4-(benzylaminomethyl) of formula (VI) Acyl)phenyl)benzamide (3)

[0176]

[0177] in N 2 Under the atmosphere, take the Al(CH 3 ) 3 2.0 M heptane (0.18 mL, 0.36 mmol) was added to (R)-methyl 3-((4-benzyl-2-oxooxazolidin-3-yl)methyl)benzoate (0.06 g , 0.18 mmol) and compound 4-amino-N-benzylbenzamide (0.081 g, 0.36 mmol) in anhydrous THF solution (10 mL); the reaction mixture was heated in a microwave reactor at 125 °C for 35 min . The crude reaction product was cooled in a mixture of ice and water, and HCl (1 N) was added dropwise until effervescence ceased. Then, it was extracted with diethyl ether (20 mL), and the organic extract was washed with anhydrous MgSO 4 Dry, and remove the solvent under reduced pressure. The crude reaction product was purified by chromatography (6:4 hexane / ethyl acetate) to afford 3 as a white solid (0.04 g, 40%). 1 H NMR (300MHz, DMSO-d 6 )δ10.47(s,1H,NH),...

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Abstract

The present invention relates to a family of differently substituted oxazolidinones and to the pharmaceutically acceptable salts, esters, prodrugs, tautomers, solvates and hydrates thereof, which show affinity for the alpha and gamma subtypes of the peroxisome proliferator-activated receptors (PPAR) and which, therefore, modulate the actions regulated by said receptors, such as inducing satiety, controlling ingestion and modulating metabolic effects, and thus are useful for the administration thereof as a pharmacological tool and as drugs for the treatment and / or prevention of metabolic diseases and cardiovascular diseases.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry and pharmacology, and in particular, relates to a family of different substituted oxazolidinones and pharmaceutically acceptable salts, esters, prodrugs, tautomers, solvates and hydrates thereof, It has an affinity for the alpha and gamma subtypes of the peroxisome proliferator-activated receptor (PPAR) receptor, and thus modulates activities regulated by the receptor, such as inducing satiety, controlling digestion, and regulating Metabolism, therefore, can be used for administration as a pharmacological tool and as a drug for the treatment and / or prevention of metabolic and cardiovascular diseases. Background technique [0002] PPAR receptors belong to a family of nuclear receptors consisting of three subtypes α, β and γ, which are involved in the transcription of genes responsible for regulating metabolism and energy balance. Therefore, their role in regulating carbohydrate and lipid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/20A61K31/421A61P3/00A61P9/00
CPCA61K8/49A61K31/421A61K2800/10A61Q19/00A61P3/00A61P9/00C07D263/22
Inventor 露丝·佩雷斯-费尔南德斯玛丽亚-尼夫斯·佛雷斯诺-洛佩兹何塞·埃尔格罗-贝尔托利尼皮拉尔·戈雅-拉扎安娜-贝伦·托雷斯-扎吉雷费尔南多·罗里格兹-德-丰塞卡弗朗西斯科-哈维尔·帕文-莫隆曼纽尔·马西亚斯-冈萨雷斯米格尔·罗梅罗-奎瓦斯
Owner セルビシオアンダルーサデサルー
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