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GPR40 receptor agonist, methods of preparing the same, and pharmaceutical compositions containing same as active ingredient

A compound and pharmaceutical technology, applied in the field of GPR40 receptor agonist, preparation thereof and pharmaceutical composition containing it as an active ingredient, can solve problems such as weight gain, weak hypoglycemia function, gastrointestinal disorders, etc.

Inactive Publication Date: 2015-08-12
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, these agents have undesired side effects such as hypoglycemia, liver failure, gastrointestinal disturbance, and weight gain, or weak hypoglycemic function or have the disadvantage of having to be used as an injection

Method used

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  • GPR40 receptor agonist, methods of preparing the same, and pharmaceutical compositions containing same as active ingredient
  • GPR40 receptor agonist, methods of preparing the same, and pharmaceutical compositions containing same as active ingredient
  • GPR40 receptor agonist, methods of preparing the same, and pharmaceutical compositions containing same as active ingredient

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0464] Preparation Example 1: Synthesis of 1-isopropyl-1H-indole-6-carbaldehyde

[0465] 1-H-Indole-6-carbaldehyde (320 mg, 2.2 mmol) was dissolved in dimethylformamide (2 ml), to which was slowly added isopropyl iodide (0.33 ml, 3.3 mmol) and sodium hydride ( 104 mg, 2.6 mmol), then the mixture was stirred at 50 °C for 8 h. A 1N hydrochloric acid solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (300 mg, 73%).

[0466] NMR: 1 H-NMR (400 HMz, CDCl 3 ); δ10.11(s, 1H), 7.96(s, 1H), 7.71(d 1H), 7.62(dd, 1H), 7.45(d, 1H), 6.59(d, 1H), 4.73-4.84(m , 1H), 1.57(d, 6H)

preparation Embodiment 2

[0467] Preparation Example 2: Synthesis of 1-benzyl-1H-indole-6-carbaldehyde

[0468] 1-H-Indole-6-carbaldehyde (320 mg, 2.2 mmol) and benzyl bromide (0.36 ml, 3.3 mmol) were reacted according to the method of Preparative Example 1 to obtain the title compound (400 mg, 77%).

[0469] NMR: 1 H-NMR (400 HMz, CDCl 3 ); δ10.06(s, 1H), 7.86(s, 1H), 7.73(d 1H), 7.64(dd, 1H), 7.35(d, 1H), 7.28-7.33(m, 3H), 7.12(dd , 2H), 6.62(d, 1H), 5.41(s, 2H)

preparation Embodiment 3

[0470] Preparation Example 3: Synthesis of 1-benzyl-3-chloro-1H-indole-6-carbaldehyde

[0471] 1-Benzyl-1H-indole-6-carbaldehyde (835 mg, 3.5 mmol) from Preparative Example 2 was dissolved in tetrahydrofuran (30 ml). N-chlorosuccinimide (NCS, 474 mg, 3.5 mmol) was added dropwise thereto, and the mixture was stirred at 70°C for 2 hours. After the reaction was completed, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (800 mg, 76%).

[0472] NMR: 1 H-NMR (400 HMz, CDCl 3 ); δ10.29(s, 1H), 7.92(s, 1H), 7.79(m, 2H), 7.37(m, 4H), 7.20(d, 2H), 5.41(s, 2H)

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Abstract

The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

Description

technical field [0001] The present invention relates to novel compounds having GPR40 receptor agonist activity, which promote insulin secretion and inhibit blood glucose elevation after glucose loading, and are thus useful in the treatment of diabetes and its complications, or pharmaceutically acceptable salts thereof and Isomers, and pharmaceutical compositions containing them. Background technique [0002] Diabetes adversely affects the health of many people and induces various complications. Diabetes is divided into type I diabetes and type II diabetes. Type I diabetes occurs due to the destruction of pancreatic cells that do not produce insulin. Type II diabetes occurs because insulin is not produced for other reasons or the body does not respond to insulin. Type II diabetes is present in 90% or more of people with diabetes. [0003] Currently, sulfonylureas (promoting insulin secretion by pancreatic cells), biguanides (inhibiting glucose production in the liver), α-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/22C07D409/04A61K31/404A61P3/10
CPCC07D409/04C07D209/22C07D209/08C07D209/12C07D209/30C07D231/56C07D235/26C07D249/18C07D261/20C07D401/04C07D401/06C07D403/06C07D405/06C07D405/12C07D413/12C07D413/14C07D417/06C07D471/04A61P13/12A61P27/02A61P3/04A61P3/06A61P43/00A61P9/00A61P9/10A61P9/12A61P3/10A61K31/404A61K31/416A61K31/4184A61K31/422A61K31/437A61K31/4439A61K31/497A61K31/5377C07D209/14C07D235/12C07D405/14
Inventor 李成培白承烨尹淑卿尹胜玄崔增洵
Owner LG CHEM LTD
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