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Derivative containing glucosamine and nitrile pyridine structure and use thereof

A technology for diabetes drugs and products, which is applied in the preparation of sugar derivatives, sugar derivatives, and sugar derivatives, etc., can solve the problems of unclear exact causes, loss of sensitivity, and decreased insulin secretion-stimulating effect.

Inactive Publication Date: 2015-05-20
FOSHAN SAIWEISI MEDICINE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in patients with type 2 diabetes it has been shown that the insulinotropic effect of GIP is decreased, although the insulinotropic effect of GLP-1 is maintained
What is puzzling is that patients with type 2 diabetes still have a good response to a large injection of GIP, but lose sensitivity to continuous small injections (Meier et al., Diabetes, 2004, 53, S220-S224), The exact reason for this decrease in GIP activity is therefore unclear

Method used

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  • Derivative containing glucosamine and nitrile pyridine structure and use thereof
  • Derivative containing glucosamine and nitrile pyridine structure and use thereof
  • Derivative containing glucosamine and nitrile pyridine structure and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0026]

[0027] A. Synthesis of Compound IV-1

[0028] Compound II-14.26g (10mmol) and compound III 2.21g (10mmol) were dissolved in 20mL of dichloromethane, stirred at room temperature, 20mL of 20% NaOH solution and 3g of benzyltriethylammonium bromide were added, and then the reaction mixture was heated at room temperature After stirring overnight, the reaction was checked by TLC for completion. The reaction mixture was poured into 100 mL of ice water, carefully adjusted to pH=2-3 with hydrochloric acid, and 50 mL×3 of CH 2 Cl 2 After extraction, the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IV-1 as a white solid, ESI-MS, m / z=567 ([M+H] + ).

[0029] B. Synthesis of Compound VI...

Embodiment 2

[0033] The preparation of embodiment 2 reference compound D-1

[0034] In order to further illustrate the pharmacological effects, the applicant listed a new compound D-1 (unpublished) and its pharmacological effects researched by the same applicant as a reference.

[0035]

[0036] A. Synthesis of Compound IV-2

[0037] Compound II-23.95g (10mmol) and compound III 2.21g (10mmol) were dissolved in 20mL of dichloromethane, stirred at room temperature, 20mL of 20% NaOH solution and 3g of benzyltriethylammonium bromide were added, and the reaction mixture was heated at room temperature After stirring overnight, the reaction was checked by TLC for completion. The reaction mixture was poured into 100 mL of ice water, carefully adjusted to pH=2-3 with hydrochloric acid, and 50 mL×3 of CH 2 Cl 2 After extraction, the extract phases were combined, washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evap...

Embodiment 3

[0042] The agonistic experiment of the compound of Example 3 on GPR119 in vitro

[0043] Three copies of a human-mouse chimeric GPR119 expression construct encoding the FLAG epitope tag, the first 198 amino acids of human GPR119, and the C-terminal 137 amino acids of the mouse receptor were cloned into the tetracycline-inducible vector pcDNA5 / FRT / TO (Invitrogen #V6520-20), which contains a hygromycin resistance marker. Finely controlled expression of the receptor was achieved by stable integration of this construct into the genome of a specific host cell line Flp-In-T-Rex-HEK293 (Invitrogen) expressing a tetracycline repressor. Once a stable hygromycin-resistant cell line is generated, maintain the cells at 37 °C in humidified 5% CO 2 atmosphere and medium. The medium consisted of Dulbecco's modified Eagle's medium supplemented with 2 mM L-glutamine, 10% fetal calf serum, 200 μg / ml hygromycin B and 15 μg / ml blasticidin. medium) (DMEM, Invitrogen).

[0044] Cells stably ...

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Abstract

The invention relates to the field of drugs associated with Type II diabetes and particularly relates to a GPR119 agonist containing glucosamine and a nitrile pyridine structure shown in the specification as well as a preparation method thereof and an application of the GPR119 agonist in preparation of Type II diabetes drugs.

Description

technical field [0001] The present invention relates to the pharmaceutical field for the treatment of type II diabetes. More specifically, the present invention relates to a GPR119 agonist containing glucosamine and cyanopyridine structure, which has a therapeutic effect on type II diabetes, its preparation method, and its application in pharmacy. Background technique [0002] Diabetes is increasingly threatening human health. In the United States today, approximately 16 million people are suffering from diabetes. Type 1 diabetes, also known as insulin-dependent diabetes, is an autoimmune disease. It is caused by the destruction of the pancreatic islet β cells that can produce insulin by the autoimmune system. There is currently no cure for this disease in the world, so patients must receive insulin injections. Without insulin injections, cells cannot absorb glucose for energy. Symptoms associated with type 1 diabetes usually appear in childhood and adolescence. Because...

Claims

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Application Information

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IPC IPC(8): C07H15/14C07H1/00A61P3/10
CPCY02P20/55C07H15/14C07H1/00
Inventor 蔡子洋
Owner FOSHAN SAIWEISI MEDICINE SCI & TECH
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