Benzopyran compound and its prepn and use

A technology of benzopyran and compounds, which is applied in the preparation of anti-type II diabetes drugs and the synthesis of benzopyran compounds, which can solve the problems of liver toxicity and high liver toxicity

Inactive Publication Date: 2006-08-02
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1997, troglitazone, the first thiazolidinedione insulin sensitizer, was launched on the market. This drug and its similar drugs, pioglitazone and rosiglitazone, which were later marketed, can control blood sugar well in clinical practice. , but these drugs have shown varying degrees of liver toxicity [Henry, R.R. Endocrinol. out of the market

Method used

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  • Benzopyran compound and its prepn and use
  • Benzopyran compound and its prepn and use
  • Benzopyran compound and its prepn and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Example 1: 7-[2-(5-methyl-2-biphenyl-4-oxazole)ethoxy]-2-oxo-2H-1-benzopyran-3-carboxylic acid Esters (compound 1)

[0087] 2-[5-Methyl-2-(4-biphenyl)-4-oxazole]ethanol [Alexander, G.G.; Dawn.A.B.J.Org.Chem.2003, 68, 2623] 0.09g (0.32mmol), Dissolve 0.07g (0.32mmol) of methyl 7-hydroxy-3-coumarincarboxylate in 15ml of anhydrous tetrahydrofuran, add 0.11g (0.42mmol) of triphenylphosphine, and add diethyl azodicarboxylate dropwise at 0°C Ester 0.08ml (0.53mmol). Stir at room temperature for 24 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in methanol to precipitate a white solid. The resulting solid was recrystallized from methanol to obtain 0.08 g of the target product, yield: 51.6%. M.P.159.0-160.0°C.

[0088] 1 HNMR (CDCl 3 ): δ=2.40(s, 3H), 3.04(t, J=6.3Hz, 2H), 3.94(s, 3H), 4.36(t, J=6.6Hz, 2H), 6.88(m, 2H), 7.37 (m, 5H), 7.60 (m, 4H), 8.04 (dd, J=8.41 Hz, J=6.92 Hz, 1H), 8.54 (s, 1H).

Embodiment 2

[0089] Example 2: 7-[2-(5-methyl-2-(4-biphenyl)-4-oxazole)ethoxy]-3,4-dihydro-2-oxo-4H-1 - Methyl benzopyran-3-carboxylate (compound 15)

[0090] Dissolve 0.07 g (0.14 mmol) of compound 1 in 10 ml of a mixed solvent of methanol:dioxane = 1:3, add 20 mg of 10% Pd-C, mix well, stir and pass hydrogen under normal pressure until hydrogen absorption stops. Pd-C was filtered off, the solvent was distilled off under reduced pressure, the residue was precipitated into a solid in methanol, and 0.06 g of the product was obtained by suction filtration, yield: 85.4%. M.P.122.5-123.0°C.

[0091] 1 HNMR (CDCl 3 ): δ=2.40(s, 3H), 3.03(t, J=6.3Hz, 2H), 3.29(dd, J=15.8Hz, J=6.05Hz, 1H), 3.54(dd, J=15.9Hz, J =8.66Hz, 1H), 3.93(m, 4H), 4.35(t, J=6.7Hz, 2H), 6.86(m, 2H), 7.02(d, J=8.65Hz, 1H), 7.37(m, 5H ), 7.59 (m, 4H).

Embodiment 3

[0092] Example 3: 7-[2-(5-methyl-2-(3-methylphenyl)-4-oxazole)ethoxy]-2-oxo-2H-1-benzopyran- 3-Carboxylic acid methyl ester (compound 2)

[0093] 2-[5-Methyl-2-(3-methylphenyl)-4-oxazole]ethanol 0.40 g (1.84 mmol) [Alexander, G.G.; Dawn.A.B.J.Org.Chem.2003, 68, 2623], Dissolve 0.41g (1.84mmol) of methyl 7-hydroxy-3-coumarincarboxylate in 60ml of anhydrous tetrahydrofuran, add 0.63g (2.40mmol) of triphenylphosphine, and add diethyl azodicarboxylate dropwise at 0°C Ester 0.08ml (3.11mmol). Stir at room temperature for 24 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in methanol to precipitate a white solid. The resulting solid was recrystallized from methanol to obtain 0.45 g of the target product, yield: 58.3%. M.P.134.0-134.5°C.

[0094] 1 HNMR (CDCl 3 ): δ=2.40(s, 3H), 2.38(s, 3H), 3.02(t, J=6.59Hz, 2H), 3.93(s, 3H), 4.34(t, J=6.59Hz, 2H), 6.83 (d, J=2.33Hz, 1H), 6.88(dd, J=8.66Hz, J=2.34Hz, 1H), 7.22(dd, J=7.70Hz, J=0.69Hz...

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Abstract

The present invention provides benzopyran compound as shown and its pharmaceutically acceptable inorganic and organic salts. The present invention also provides the preparation process of the compounds and medicine composite including the compounds as the active matter for treating type-II diabetes and its complications.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and endocrine therapy, in particular to the synthesis of a class of benzopyran compounds and their use in the preparation of anti-II diabetes drugs. Background technique [0002] Diabetes mellitus is a group of clinical syndromes characterized by chronic hyperglycemia as the main manifestation of abnormal carbohydrate, fat and protein metabolism due to insufficient secretion of insulin or insulin resistance. It is now believed that insulin resistance (skeletal muscle, liver, fat tissue and other peripheral tissues are less sensitive to insulin) is the main cause of type 2 diabetes. Sustained hyperglycemia can lead to many complications, such as retinal, renal, nervous system, and cardiovascular complications, especially cardiovascular complications are the main cause of death and disability in diabetic patients [Shinkai, H.Exp.Opin.Ther. Patents. 2000, 10: 596]. [0003] Studies have shown th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C07D311/20A61K31/352A61K31/353A61P3/10
CPCC07D311/16C07D413/12C07D311/20A61P3/10
Inventor 杨玉社余娟红嵇汝运陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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