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Compound containing hydrazide and cyanobenzene structures as well as preparation method and application thereof

A compound and drug technology, applied in the field of GPR119 agonists, can solve the problems of decreased insulin secretion, decreased GIP activity, and unclear exact reasons, etc.

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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  • Compound containing hydrazide and cyanobenzene structures as well as preparation method and application thereof
  • Compound containing hydrazide and cyanobenzene structures as well as preparation method and application thereof
  • Compound containing hydrazide and cyanobenzene structures as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 compound I-1

[0028]

[0029] A. Synthesis of Compound IV-1

[0030] Compound II-1 (0.68g, 10mmol) and compound III (1.95g, 10mmol) were dissolved in 20mL dry DMF, stirred at room temperature, solid potassium carbonate (4.15g, 30mmol) and 0.5g KI were added, and then heated at 80°C Stirring was continued until the reaction was complete (about 5 hours). The reaction mixture was poured into 150 mL ice water with 50 mL × 3 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, a white solid, ESI-MS, m / z=183 ([M+H] + ).

[0031] B. Synthesis of Compound V-1

[0032] Compound IV-1 (1.28g, 7mmol) was dissolved in 15mL of absolute ethanol, stirred at room temperature, 1mL of...

Embodiment 2-3

[0036] Referring to the method of Example 1, the following compounds were synthesized.

[0037]

Embodiment 4

[0038] The synthesis of embodiment 4 compound D-1

[0039] In order to further illustrate the beneficial effect of the compound of the present invention, the applicant has recorded the compound D-1 and pharmacological data that the applicant has studied but not yet published.

[0040]

[0041] A. Synthesis of Compound IV-1

[0042] Compound II-1 (0.68g, 10mmol) and compound III (1.95g, 10mmol) were dissolved in 20mL dry DMF, stirred at room temperature, solid potassium carbonate (4.15g, 30mmol) and 0.5g KI were added, and then heated at 80°C Stirring was continued until the reaction was complete (about 5 hours). The reaction mixture was poured into 150 mL of ice water, extracted with 50 mL×3 of CH2Cl2, the combined extracts were 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 ...

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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 hydrazide and cyanobenzene structures, a preparation method of the GPR119 agonist and application of the GPR119 agonist to preparation of medicines related to type II diabetes mellitus. A structure of the GPR119 agonist is shown in the specification.

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 agonist containing hydrazide and nitrile benzene 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. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/56A61P3/10
CPCC07D233/56
Inventor 蔡子洋
Owner FOSHAN SAIWEISI MEDICINE SCI & TECH
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