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Containing adamantane and amide derivatives, its preparation method and use

An alkyl and aspect technology, applied in the field of diabetes-related drugs, can solve problems such as undiscovered weight gain

Active Publication Date: 2016-03-23
怀仁诚隆化工科技有限公司
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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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  • Containing adamantane and amide derivatives, its preparation method and use
  • Containing adamantane and amide derivatives, its preparation method and use
  • Containing adamantane and amide derivatives, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of embodiment 1 compound I-1

[0026]

[0027] In a 100mL round bottom flask, add 2.22g (10mmol) compound II-1, 3.21g (10mmol) compound III, 2.06g (10mmol) N, N'-dicyclohexylcarbodiimide (DCC) and 1.22g (10mmol) 4-dimethylaminopyridine (DMAP), dissolved in 20mL of dry THF, stirred at room temperature overnight, TLC showed that the reaction was almost complete. The reaction mixture was suction filtered to remove the solid, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by column chromatography to obtain compound IV-1, a white solid, ESI-MS, m / z=543 ([M+NH 4 ] + ).

[0028] 3.15 g (6 mmol) of compound IV-1 was dissolved in 30 mL THF, 0.10 g of 10% Pd / C was added, catalytic hydrogenolysis was carried out at room temperature, and the reaction was completed within 12 hours. The reaction mixture was suction filtered to remove the catalyst, and the filtrate was concentrated on a rotary evaporator, poured into 2...

Embodiment 2-6

[0032] Referring to the method of Example 1, the following compounds can be prepared.

[0033]

[0034]

Embodiment 7

[0035] Embodiment 7 compound is measured to the inhibitory action of DPP-IV enzyme

[0036] Using the fluorescent DPP4 activity detection kit of BPS Bioscience Company, the inhibitory activity of the compound of the present invention on DPP-IV enzyme was determined.

[0037] 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:

[0038]

[0039] Place in a water bath at 22°C for 10 minutes, use a SpectraMaxM5 type fluorescence detector with an excitation light of 350nm, and measure the absorbance with 450nm fluorescence. Calculation of IC from the concentration-fluorescence intensity curve 50 values, see the table below.

[0040] IC of compounds for inhibition of DPP-IV enzymes 50 value

[0041]

[0042] 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 drugs relevant to diabetes, in particular to a dipeptidyl peptidase-IV inhibitor containing a general formula I, adamantane, amide and other structures, a preparation method of the dipeptidyl peptidase-IV inhibitor and application in diabetes drug preparation. According to the general formula I (please see the specification), R<1> is selected from an alkyl group of H, an alkyl group of C1-C5 and a naphthenic base of C3-C5.

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 adamantane and amide structures, 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 (dipeptidylpeptidase IV, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/16A61K31/4025A61P3/10
CPCY02P20/55
Inventor 蔡子洋
Owner 怀仁诚隆化工科技有限公司