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Novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, method of preparing same and pharmaceutical composition for preventing and treating metabolic disease including same as effective ingredient

一种苄氧基、苯基的技术，应用在3-苯基)己-4-炔酸衍生物领域，能够解决增加体重、失去治疗药物反应性、胃肠道问题等问题，达到促进活化的效果

Active Publication Date: 2015-12-02
HYUNDAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, recent treatment methods have problems: causing hypoglycemia, gaining weight, losing responsiveness to therapeutic drugs after a long period of time, causing gastrointestinal problems and edema, etc.

Method used

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  • Novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, method of preparing same and pharmaceutical composition for preventing and treating metabolic disease including same as effective ingredient
  • Novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, method of preparing same and pharmaceutical composition for preventing and treating metabolic disease including same as effective ingredient
  • Novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, method of preparing same and pharmaceutical composition for preventing and treating metabolic disease including same as effective ingredient

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0165] In the preparation method of the compound represented by Formula 1 of the present invention, step 1) is to prepare the compound represented by Formula 4 by causing a coupling reaction between the compound represented by Formula 2 and the compound represented by Formula 3. More specifically, the compound represented by Formula 2, the compound represented by Formula 3, and triphenylphosphine were all mixed to obtain a mixed solution. Azocarboxylate reagent (Azocarboxylate reagent) is slowly added to the mixed solution at a temperature of -5°C to 10°C, followed by causing Mitsunobureaction to obtain the compound represented by Formula 4.

[0166] At this time, the azodicarboxylate reagent can be selected from the group consisting of diethyl azodicarboxylate (DEAD) and diisopropyl azodicarboxylate (DIAD), and preferably diethyl azodicarboxylate Isopropyl ester (DIAD).

[0167] The reaction solvent here may be selected from the group consisting of tetrahydrofuran (THF), dic...

manufacture example 1

[0254] Production Example 1: Preparation of ethyl 3-(4-hydroxyphenyl)hex-4-ynoate

[0255]

[0256] 3-(4-Hydroxyphenyl)-hex-4-ynoic acid (20.0 g) and ethanol (200 mL) were charged into a 250 mL flask under a nitrogen atmosphere, followed by stirring to dissolve them. Sulfuric acid (9.6 mL) was slowly added to this at room temperature. The mixture was stirred at reflux for at least 6 hours. Upon completion of the reaction, distilled water (150 mL) was slowly added thereto, followed by extraction with ethyl acetate (200 mL). The extracted organic layer was dried under reduced pressure to obtain the target compound (19.5 g, 85.7%).

[0257] 1 HNMR (400MHz, CDCl 3 ): δ7.25(2H,d), 6.78(2H,d), 4.95(1H,s), 4.14(2H,m), 4.04(1H,m), 2.68(2H,m), 1.84(3H, d), 1.29(3H,t).

manufacture example 2

[0258] Production Example 2: Preparation of (S)-3-(4-hydroxyphenyl)hex-4-ynoic acid ethyl ester

[0259]

[0260] (S)-3-(4-Hydroxyphenyl)-hex-4-ynoic acid (20.0 g) and ethanol (200 mL) were charged into a 250 mL flask under a nitrogen atmosphere, followed by stirring to dissolve them. Sulfuric acid (9.6 mL) was slowly added to this at room temperature. The mixture was stirred at reflux for at least 6 hours. Upon completion of the reaction, distilled water (150 mL) was slowly added thereto, followed by extraction with ethyl acetate (200 mL). The extracted organic layer was dried under reduced pressure to obtain the target compound (21.2 g, 93.2%).

[0261] 1 HNMR (400MHz, CDCl 3 ): δ7.25(2H,d), 6.78(2H,d), 4.95(1H,s), 4.14(2H,m), 4.04(1H,m), 2.68(2H,m), 1.84(3H, d), 1.29(3H,t).

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Abstract

The present invention relates to a novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, a method of preparing same and a pharmaceutical composition for preventing and treating metabolic disease including same as an effective ingredient. The novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, an optical isomer thereof, or a pharmaceutically acceptable salt thereof, according to the present invention, has an excellent effect on activation of GPR40 protein and thus has excellent promoting effect of insulin secretion; is nontoxic when co-administrated with other drugs and is possibly co-administrated with other drugs; and has excellent effective effect of activating GPR40 protein in vivo. Therefore, a composition including the novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof may be availably used in a pharmaceutical composition for preventing and treating metabolic disease such as obesity, type I diabetes, type II diabetes, incompatible glucose tolerance, insulin tolerance, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia, syndrome X, etc.

Description

technical field [0001] The present invention relates to a novel 3-(4-(benzyloxy)phenyl)hex-4-ynoic acid derivative, a preparation method thereof, and a drug for preventing and treating metabolic diseases comprising the same as an active ingredient combination. Background technique [0002] Diabetes is a serious disease that continues to threaten our health, and at least 100 million people worldwide already suffer from diabetes. Diabetes can be classified into two clinical symptom categories, Type I diabetes and Type II diabetes. Type 1 diabetes, known as insulin-dependent diabetes mellitus (IDDM), results from autoimmune destruction of insulin-producing pancreatic beta cells, so that it requires regular administration of exogenous insulin. Type 2 diabetes, known as non-insulin-dependent diabetes mellitus (NIDDM), results from defective control of blood sugar. Thus, those with type II diabetes characteristically show a defect in insulin secretion or insulin resistance, whi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/72A61K31/357A61P3/10
CPCC07D213/85C07D215/06C07D217/04C07D221/20C07D317/72C07D239/42C07D271/07C07D277/82C07D209/44C07D211/14C07D295/073C07D295/096C07C51/367C07C51/373C07C59/72C07C59/90C07D207/06C07D211/70C07D213/74C07D215/04C07D217/24C07D239/28C07D295/155C07D413/04A61P3/00A61P3/04A61P3/06A61P43/00A61P3/10A61K31/496A61K31/47A61K31/4035A61K31/357C07D221/04C07D241/04C07D213/55
Inventor 梁镇金镇雄李汉奎金在贤孙昌模李揆焕崔亨豪金大训河泰荣李在杰
Owner HYUNDAI PHARMA
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