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Benzopyran compounds and preparation method thereof as well as pharmaceutical composition and use of benzopyran compounds

A technology of benzopyran and compounds, applied in the field of benzopyran compounds, can solve problems such as lack, lack of triglyceride regulation, hypoglycemia, etc.

Inactive Publication Date: 2019-09-17
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs are only aimed at the index of hyperglycemia, but lack the regulation of triglycerides at the same time, and many antidiabetic drugs have a wide range of adverse reactions, such as liver toxicity, lactic acidosis, vitamin B 12 Deficiency and severe hypoglycemia etc.

Method used

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  • Benzopyran compounds and preparation method thereof as well as pharmaceutical composition and use of benzopyran compounds
  • Benzopyran compounds and preparation method thereof as well as pharmaceutical composition and use of benzopyran compounds
  • Benzopyran compounds and preparation method thereof as well as pharmaceutical composition and use of benzopyran compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 6-methoxybenzo-2H-pyran-3-yl-2′,3′-dihydroxyphenyl ketone 1c

[0022]

[0023] (1) The preparation method of 6-methoxybenzopyran-3-carbonitrile

[0024] Dissolve 1g of 2-hydroxy-5-methoxybenzaldehyde in 2mL of acrylonitrile, add 2eq. of 1,4-diazabicyclo[2.2.2]octane, and reflux for 12h. The product 6-methoxybenzopyran-3-carbonitrile was obtained by column chromatography. 1 HNMR (500MHz, CDCl 3 ):7.13(s,1H),6.84(dd,J=9.0,3.0Hz,1H),6.82(d,J=9.0Hz,1H),6.63(d,J=2.5Hz,1H),4.75(s ,2H),3.77(s,1H); 13 CNMR (125MHz, CDCl 3 ):154.9,148.5,139.1,120.8,118.8,117.6,116.7,112.7,104.4,64.6,56.0; ESI-MS:[M+H] + :188.1,[M+NH 4 ] + :205.1.

[0025] (2) The preparation method of 6-methoxybenzo-2H-pyran-3-aldehyde

[0026] Under argon protection, 6-methoxychromene-3-carbonitrile was dissolved in toluene (150mg / mL), cooled to -50°C, added diisopropylaluminum hydride (1.1eq.) and stirred for 2h. Stirring was then continued for 2 h at room temperature. Add 100 mL of eth...

Embodiment 2

[0033] Example 2 5-methoxybenzo-2H-pyran-3-yl-2′,3′-dihydroxyphenyl ketone 1h

[0034]

[0035] (1) The preparation method of 5-methoxybenzopyran-3-carbonitrile

[0036] Dissolve 1g of 2-hydroxy-6-methoxybenzaldehyde in 2mL of acrylonitrile, add 2eq. of 1,4-diazabicyclo[2.2.2]octane, and reflux for 12h. The product 5-methoxybenzopyran-3-carbonitrile was obtained by column chromatography. 1 HNMR (500MHz, CDCl 3 ):7.54(s,1H),7.21(t,J=8.5Hz,1H),6.48(t,J=9.0Hz,2H),4.74(d,J=1.0Hz,2H),3.85(s,3H ); 13 CNMR (125MHz, CDCl 3 ):156.4, 155.2, 134.5, 133.0, 117.0, 110.3, 109.0, 104.1, 100.5, 63.9, 55.8; ESI-MS: [M+H] + :188.1,[M+NH 4 ] + :205.1.

[0037] (2) The preparation method of 5-methoxybenzo-2H-pyran-3-aldehyde

[0038] Under argon protection, 5-methoxychromene-3-carbonitrile was dissolved in toluene (150mg / mL), cooled to -50°C, added diisopropylaluminum hydride (1.1eq.) and stirred for 2h. Stirring was then continued for 2 h at room temperature. Add 100 mL of ethyl ac...

Embodiment 3

[0045] Example 3 8-methoxybenzo-2H-pyran-3-yl-2′,5′-dihydroxyphenyl ketone 1i

[0046]

[0047] (1) Preparation of 8-methoxybenzo-2H-pyran-3-carbonitrile

[0048] Dissolve 1g of 2-hydroxy-3-methoxybenzaldehyde in 2mL of acrylonitrile, add 2eq. of 1,4-diazabicyclo[2.2.2]octane, and reflux for 12h. The product 8-methoxybenzo-2H-pyran-3-carbonitrile was obtained by column chromatography. 1 HNMR (500MHz, CDCl 3 ):7.17(s,1H),6.93-6.91(m,2H),6.75-6.73(m,1H),4.87(d,J=1.0Hz,2H),3.88(s,1H); 13 CNMR (125MHz, CDCl 3 ):148.2, 143.4, 139.0, 122.3, 120.8, 120.4, 116.4, 115.4, 103.6, 64.7, 56.3; ESI-MS: [M+H] + :188.1,[M+NH 4 ] + :205.1.

[0049] (2) Preparation of 8-methoxybenzo-2H-pyran-3-yl-2′,5′-dihydroxyphenylketone

[0050] Add 8-methoxybenzo-2H-pyran-3-carbonitrile (0.2eq.) to the newly prepared Grignard reagent 2,5-bisMOMO-phenylmagnesium bromide, and reflux for 22h until the raw material disappears. Add 2N hydrochloric acid (2 mL) and reflux for 30 min. Add 100 mL of et...

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Abstract

The invention discloses benzopyran compounds as shown in a formula I, a preparation method of the benzopyran compounds, a composition containing the compounds, and use of the compounds in preparation of a farnesoid X receptor antagonist, a liver protection agent and medicines for preventing and treating hyperlipidemia and diabetes mellitus type II.

Description

technical field [0001] The invention discloses a class of polyhydroxy polyalkoxy substituted benzopyran compounds, a preparation method of this type of benzopyran, a composition containing this type of compound and the use of this type of compound as an FXR antagonist for preparing and preventing The invention relates to new uses of type 2 diabetes, hyperlipidemia and liver protection drugs, and belongs to the field of medical technology. Background technique [0002] Diabetes is one of the most common chronic diseases that seriously endanger human health. With the advancement of science and technology and the change of people's lifestyle, the incidence rate is increasing year by year. According to the Baker Heart and Diabetes Institute in Australia, the global incidence of diabetes will reach 7.7% by 2030, and a total of 439 million people will suffer from diabetes; from 2010 to 2030, the incidence of diabetes among adults in developing countries will increase by 69%. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58C07D311/64A61K31/352A61P3/10A61P3/06A61P1/16
CPCC07D311/58C07D311/64A61P3/10A61P3/06A61P1/16
Inventor 方唯硕申竹芳张国宁环奕孙得洋王星贾文强孙素娟李彩娜
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI