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GPR119 agonist containing glucosamine and halogenated pyridine structures and application thereof

An alkyl and halogen technology, applied in the field of GPR119 agonists, can solve the problems of unclear exact cause, loss of sensitivity, and decreased insulin secretion promoting effect

Inactive Publication Date: 2015-05-13
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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  • GPR119 agonist containing glucosamine and halogenated pyridine structures and application thereof
  • GPR119 agonist containing glucosamine and halogenated pyridine structures and application thereof
  • GPR119 agonist containing glucosamine and halogenated pyridine structures and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The synthesis of embodiment 1 compound I-1

[0030]

[0031] A. Synthesis of Compound IV-1

[0032] Compound II-14.10g (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=551 ([M+H] + ).

[0033] B. Synthesis of Compound VI-...

Embodiment 2-10

[0038] Referring to the method of Example 1, the compounds listed in the following table were synthesized.

[0039]

[0040]

Embodiment 11

[0041] Preparation of Example 11 Reference Compound D-1

[0042] 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.

[0043]

[0044] A. Synthesis of Compound IV-11

[0045] Compound II-11 3.95g (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 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 evap...

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Abstract

The invention relates to the field of medicines related to type II diabetes mellitus and in particular relates to a GPR119 agonist containing glucosamine and halogenated pyridine structures, a preparation method of the GPR119 agonist and application of the GPR119 agonist to preparation of medicines related to type II diabetes mellitus. The GPR119 agonist has a structure shown in a general formula in the specification, wherein in the general formula, R1 is selected from C1-C3 alkyl; R2 is selected from halogen substituent.

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 class of GPR119 agonists containing glucosamine and halopyridine structures that have therapeutic effects on type II diabetes, its preparation method, and its use 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): C07H15/14A61P3/10
CPCC07H15/14
Inventor 蔡子洋
Owner FOSHAN SAIWEISI MEDICINE SCI & TECH
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