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Substituted cyclobutane carboxylic acid compounds and uses thereof

A compound, alkyl technology, application in the prevention and treatment of influenza virus-related diseases, application fields in the preparation of drugs for the prevention and treatment of influenza virus-related diseases

Active Publication Date: 2016-04-20
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to literature reports, other anti-influenza virus drugs have good inhibitory effects on viruses and antiviral application prospects, but further demonstration is often needed

Method used

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  • Substituted cyclobutane carboxylic acid compounds and uses thereof
  • Substituted cyclobutane carboxylic acid compounds and uses thereof
  • Substituted cyclobutane carboxylic acid compounds and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0157] Example 1: 3-Acetamido-3-(1-amino-3-ethylpentyl)cyclobutanecarboxylic acid

[0158]

[0159] Step 1: Synthesis of 3-ethyl-1-nitro-1-pentanol

[0160] At -10°C, slowly add nitromethane (32mL, 0.6mol, 3.0eq) dropwise to a solution of tetrabutylammonium fluoride (20.0g, 0.2mol, 0.2eq) in tetrahydrofuran (100mL), dropwise, and mix The solution was continued to stir at this temperature for 1 hour. Then 2-ethylbutyraldehyde (20 g, 0.5 mol, 1 eq) was added dropwise to the above solution. After the dropwise addition, the reaction solution continued to stir, and the reaction progress was monitored by TLC, and the reaction was processed after about 1 hour. Saturated ammonium chloride solution was added to the reaction solution, and the layers were separated. The aqueous phase was extracted with ethyl acetate (50 mLx3), and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed under reduced pressure, a...

Embodiment 2

[0192] Example 2: 3-(1-Acetamido-3-ethylpentyl)-3-aminocyclobutanecarboxylic acid

[0193]

[0194] Step 1: Synthesis of methyl 3-benzyloxycarbonylamino-3-(3-ethyl-1-nitropentyl)cyclobutanecarboxylate

[0195] At 0°C, methyl 3-amino-3-(3-ethyl-1-nitropentyl)cyclobutanecarboxylate (0.5g, 1.83mmol, 1.0eq) and triethylamine (0.56mL, 4.04 To a solution of mmol, 2.2 eq) in dichloromethane (5 mL) was added dropwise CbzCl (0.38 g, 2.2 mmol, 1.2 eq). After dropping, the mixture was stirred at 0°C for reaction, and the reaction progress was monitored by TLC. A saturated ammonium chloride solution (5 mL) was added to the reaction solution, and the layers were separated. The aqueous phase was extracted with dichloromethane (10 mLx3), and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to remove the solvent, purified by silica gel column chromatography, eluent PE / EA (V / V)=5 / 1, and the product ...

Embodiment 3

[0208] Example 3: 3-Acetamido-3-(3-ethyl-1-guanidinopentyl)-cyclobutanecarboxylic acid

[0209]

[0210] Step 1: Synthesis of methyl 3-acetamido-3-(1-amino-3-ethylpentyl)cyclobutanecarboxylate

[0211] At room temperature, Raney nickel (20mg, content 20%) was added to methyl 3-acetamido-3-(3-ethyl-1-nitropentyl)cyclobutanecarboxylate (0.1g, 0.32mmol, 1.0eq) in methanol solution (5mL), the reaction system was replaced by H 2 system, and TLC monitored the reaction progress. The reaction solution was filtered with celite, the filter cake was washed with methanol (10 mL), the solvent was removed under reduced pressure, and purified by silica gel column chromatography (eluent DCM / MeOH (V / V)=8 / 1) to obtain the product as a yellow oil Material, 56mg, yield 62%.

[0212] MS(ESI,pos.ion)m / z:285.2[M+1] + .

[0213] Step 2: Synthesis of methyl 3-(1-(2,3-bis(tert-butoxycarbonyl)guanidino)-3-ethylpentyl)-3-acetylaminocyclobutanecarboxylate

[0214] Dissolve methyl 3-acetylamino-3-...

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Abstract

The invention discloses substituted cyclobutane carboxylic acid compounds and application thereof and relates to cyclobutane carboxylic acid compounds or stereoisomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically-acceptable salts or prodrugs of the cyclobutane carboxylic acid compounds. The invention also relates to application of the cyclobutane carboxylic acid compounds or the stereoisomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically-acceptable salts or prodrugs of the cyclobutane carboxylic acid compounds as drugs and particularly relates to application of the cyclobutane carboxylic acid compounds or the stereoisomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically-acceptable salts or prodrugs of the cyclobutane carboxylic acid compounds to preparation of antiviral drugs.

Description

technical field [0001] The invention relates to a class of substituted cyclobutane carboxylic acid compounds, its preparation method and its application in the preparation of antiviral drugs, especially the application in the preparation of drugs for the prevention and treatment of influenza virus-related diseases. The present invention also relates to a pharmaceutical composition containing these compounds, and the application of the pharmaceutical composition in preventing and treating influenza virus-related diseases. Background technique [0002] Influenza (influenza, referred to as influenza) is an acute respiratory infection caused by influenza virus, and it is also a highly contagious and fast-spreading disease. It is mainly spread through droplets in the air, person-to-person contact or contact with contaminated items. Typical clinical symptoms are: sudden onset of high fever, general pain, significant fatigue and mild respiratory symptoms. Generally, autumn and wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/14C07C279/16C07C233/52C07C233/47A61K31/196A61P31/16
Inventor 张健存任青云敖丽华胡柏林张英俊
Owner SUNSHINE LAKE PHARM CO LTD
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