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Substituted cyclohexane carboxylic acid amide derivative and pharmaceutical application thereof

A diabetes drug, alkyl technology, applied in the field of drugs for the treatment of diabetes, can solve problems such as undiscovered weight gain

Inactive Publication Date: 2015-02-18
ZHEJIANG PHARMA COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinical results show that this type of drug has a good hypoglycemic effect, and no adverse reactions such as weight gain and hypoglycemia, which are common in other diabetes drugs, have been found

Method used

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  • Substituted cyclohexane carboxylic acid amide derivative and pharmaceutical application thereof
  • Substituted cyclohexane carboxylic acid amide derivative and pharmaceutical application thereof
  • Substituted cyclohexane carboxylic acid amide derivative and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] 14.22g (100mmol) of compound II-1 was refluxed in 50mL of thionyl chloride for 5 hours, and then the excess thionyl chloride was aliphatically divided, and the obtained residue was dissolved in 20mL of dry dichloromethane for later use. Dissolve 19.61g (100mmol) of compound III-1 and 30.36g (300mmol) of triethylamine in dichloromethane, stir under cooling in an ice-water bath, then slowly add the above-prepared II-1 acid chloride solution dropwise, and the dropwise addition is complete Afterwards, stirring was continued overnight at room temperature. The reaction mixture was poured into 500 mL of ice water, stirred, extracted with 100 mL×3 dichloromethane, the combined extracts were washed with saline, dried over anhydrous sodium sulfate, and then evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography , to obtain the pure product of IV-1. ESI-MS, m / z=321 ([M+H] + ).

[0028] 6.40 g (20 mmol) of compoun...

Embodiment 2-4

[0031] Referring to the method of Example 1, the following compounds can be prepared.

[0032]

Embodiment 5

[0033] Embodiment 5 compound measures the inhibition of DPP-IV enzyme

[0034] The Fluorogenic DPP4Assay Kit from BPS Company was used to determine the inhibitory activity of the compounds of the present invention on DPP-IV enzymes.

[0035] Dilute the samples successively according to the concentration of 5, 10, 30, 100 and 200ng / kg, and add the samples in the following table in the fluorescence reaction 96-well plate:

[0036]

[0037] Place in a water bath at 22°C for 10 minutes, use a Spectra Max M5 fluorescence detector with an excitation light of 350am, and measure the absorbance with 450nm fluorescence. Calculation of IC from the concentration-fluorescence intensity curve 50 values, see the table below.

[0038] IC of compounds for inhibition of DPP-IV enzymes 50 value

[0039]

[0040] It can be seen from the above table that the compound of the present invention has a strong inhibitory effect on DPP-IV enzyme.

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PUM

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Abstract

The invention relates to the field of diabetes related medicines. Specifically, the invention relates to a cyclohexane carboxylic acid amide structure-containing dipeptidyl peptidase-IV inhibitor with the general formula I shown in specifications and a preparation method thereof, a pharmaceutical composition containing the dipeptidyl peptidase-IV inhibitor and application of the dipeptidyl peptidase-IV inhibitor in preparation of medicines for treating diabetes, wherein R1 can be selected from H and C1-C5 alkyl; R2 can be selected from CN and NO2.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a dipeptidyl peptidase-IV inhibitor containing a cyclohexanecarboxamide structure, a preparation method thereof, a pharmaceutical composition containing them and a medicine for treating diabetes. Background technique [0002] According to statistics, there were approximately 250 million diabetic patients in the world in 2007, most of whom were type II (ie, non-insulin-dependent) diabetic patients. The antidiabetic drugs currently in clinical use mainly include sulfonylureas, metformin and insulin drugs. In recent years, insulin sensitizers and α-glucosidase inhibitors have also been marketed. These drugs have good therapeutic effects, but severe side effects such as hypoglycemia are common, and there are safety problems in long-term treatment, such as liver toxicity and weight gain. [0003] Dipeptidyl peptidase IV (dipeptidyl peptidase ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/52A61P3/10
CPCC07D209/52
Inventor 郭章华
Owner ZHEJIANG PHARMA COLLEGE