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Aryl gpr120 receptor agonists and uses thereof

A bicyclic aryl and bicyclic heteroaryl technology, applied in the field of aryl GPR120 receptor agonists and their uses, can solve problems such as elevation and increased insulin release

Inactive Publication Date: 2011-09-14
CYMABAY THERAPEUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The second component is the inability to respond to a hyperglycemic challenge with increased insulin release above the already elevated basal output
However, to date, there does not appear to be a way to selectively affect these pathways to promote incretin secretion for therapeutic benefit

Method used

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  • Aryl gpr120 receptor agonists and uses thereof
  • Aryl gpr120 receptor agonists and uses thereof
  • Aryl gpr120 receptor agonists and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0402] Preparation of compounds of the present invention

[0403] The compounds of the present invention can be prepared in a variety of ways familiar to those skilled in the art of synthetic organic chemistry. Synthetic routes to compounds of the present invention are not limited to the methods outlined herein or as provided in the Examples. Individual compounds may require manipulation of conditions to provide various functional groups and may require the appropriate use of protecting groups. Purification can be achieved, if necessary, by elution on a silica gel column with an appropriate organic solvent system. Reverse phase HPLC or recrystallization can also be used.

[0404] Therapeutic compositions and methods

[0405] According to the present invention there is provided a method of treating a disease or condition selected from the group consisting of Type I diabetes, Type II diabetes and metabolic syndrome. The methods comprise administering to a subject in need of ...

example 1

[0648] 3-(3,5-Difluoro-4-((3-isopropyl-1-phenyl-1H-pyrazol-5-yl)methoxy)phenyl)propanoic acid (55)

[0649]

[0650] Step A: Add intermediate (53) (0.160 g, 0.693 mmol), polymer-supported triphenylphosphine (3 mmol / g, 0.347g, 1.04mmol) and diisopropyl azodicarboxylate (0.205mL, 1.04mmol). The resulting suspension was stirred for 18 hours. The reaction was diluted with ethyl acetate and filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (0-20% EtOAc in hexanes) to afford intermediate (54).

[0651] Step B: To a solution of intermediate (54) (0.270 g, 0.630 mmol) in THF (1 mL) and methanol (1 mL) was added lithium hydroxide solution (1.0 M, 1.0 mL). The reaction was stirred at room temperature for 4 hours. The mixture was acidified with 1M HCl and diluted with EtOAc (5 mL). The organic layer was washed with brine (5 mL), dried over sodium sulfate and filtered. The filtrate was concentrated i...

example 2

[0653] Ethyl 3-(3,5-difluoro-4-((4-phenyl-1,2,3-thiadiazol-5-yl)methoxy)phenyl)propanoate (57)

[0654]

[0655] Step A: To a solution of intermediate (5) (0.200 g, 0.787 mmol) in acetonitrile (3 mL) was added intermediate (53) (0.181 g, 0.787 mmol) and cesium carbonate (0.308 g, 0.945). The resulting suspension was stirred at 80°C for 4 hours. The reaction was cooled to room temperature, diluted with ethyl acetate and filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (0-20% EtOAc in hexanes) to afford intermediate (56).

[0656] Step B: To a solution of intermediate (56) (0.318 g, 0.787 mmol) in THF (1 mL) and methanol (1 mL) was added lithium hydroxide solution (1.0 M, 1.0 mL). The reaction was stirred at room temperature for 4 hours. The mixture was acidified with 1M HCl and diluted with EtOAc (5 mL). The organic layer was washed with brine (5 mL), dried over sodium sulfate and filtered....

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Abstract

Aryl GPR120 agonists are provided. These compounds are useful for the treatment of metabolic diseases, including Type II diabetes and diseases associated with poor glycemic control.

Description

Background technique [0001] Diabetes can be divided into two clinical syndromes, Type I and Type II diabetes. Type I diabetes or insulin-dependent diabetes is a chronic autoimmune disease characterized by a massive loss of insulin-producing beta cells (hereinafter referred to as "islet cells") in the islets of Langerhans of the pancreas. As these cells are progressively destroyed, the amount of insulin secreted decreases, eventually leading to hyperglycemia (abnormal levels of glucose in the blood) when the amount secreted falls below the level required for euglycemia (normal blood sugar levels). high). Although the exact trigger of this immune response is unknown, type 1 diabetics have high levels of antibodies directed against pancreatic beta cells (hereinafter "beta cells"). However, not all patients with high levels of these antibodies develop type 1 diabetes. [0002] Type 2 diabetes, or non-insulin-dependent diabetes, develops when muscle, fat, and liver cells fail to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D233/64C07D249/06C07D261/08C07D263/32C07D277/24C07D285/06C07D307/42C07D333/16C07D409/04A61K31/41A61P3/10
CPCC07D231/12C07D285/06C07D263/32C07D277/24C07D409/04C07D307/42C07D233/64C07D249/06C07D261/08C07D333/16A61P3/00A61P3/06A61P5/50A61P3/10A61K31/415
Inventor 马靖原阿龙·诺瓦克伊马德·纳沙希比凤利·范克里斯多夫·J·拉巴特宋建高施东芳赵祖春崔于中陈新
Owner CYMABAY THERAPEUTICS
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