Composite preparation, containing novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative and another active ingredient, for preventing or treating metabolic diseases

A metabolic disease, benzyloxy technology, applied in the field of pharmaceutical compositions for the prevention or treatment of metabolic diseases, can solve problems such as low therapeutic responsiveness, and achieve excellent blood sugar lowering effect

Active Publication Date: 2017-05-24
HYUNDAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are problems associated with currently available treatments including hypoglycemia, weight gain, problems with lower responsiveness to treatment over time, gastrointestinal problems, and edema

Method used

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  • Composite preparation, containing novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative and another active ingredient, for preventing or treating metabolic diseases
  • Composite preparation, containing novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative and another active ingredient, for preventing or treating metabolic diseases
  • Composite preparation, containing novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative and another active ingredient, for preventing or treating metabolic diseases

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0119] The preparation method of the compound represented by Chemical Formula 1 of the present invention is as follows.

[0120] Preparation method 1

[0121] As shown in the following reaction formula 1, the preparation method of the compound represented by chemical formula 1 of the present invention comprises: step 1, making the compound represented by chemical formula 2 and the compound represented by chemical formula 3 undergo condensation reaction to prepare the compound represented by chemical formula 4 a compound; and step 2 of performing a reduction reaction on the compound represented by Chemical Formula 4 prepared in the above Step 1 to prepare the compound represented by Chemical Formula 1.

[0122] Reaction 1:

[0123] (In the above reaction formula 1, R 1 , R 2 , R 3 , R 4A , R 4B , R 5 , A, E, n and X are the same as defined in the above chemical formula 1; Y is C 1-10 straight-chain or side-chain alkyl).

[0124] Hereinafter, the preparation method of...

preparation example 1

[0203] Preparation of 3-(4-hydroxyphenyl)-4-hexenoic acid ethyl ester

[0204]

[0205] Under a nitrogen atmosphere, inject 3-(4-hydroxyphenyl)-hex-4-enoic acid (20.0 g) and ethanol (200 mL) into a 250 mL flask, and after stirring to complete the dissolution, slowly Sulfuric acid (9.6 mL) was instilled dropwise. Then, reflux stirring was performed for 6 hours or more, and when the reaction was complete, distilled water (150 mL) was dripped slowly, and ethyl acetate (200 mL) was inject|poured, and extraction was performed. The extracted layers were dried under reduced pressure to obtain the target compound (19.5 g, 85.7%).

[0206] 1 H NMR (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).

preparation example 2

[0207] Preparation of (S)-3-(4-hydroxyphenyl)-4-hexenoic acid ethyl ester

[0208]

[0209] Under a nitrogen atmosphere, (S)-3-(4-hydroxyphenyl)-hex-4-enoic acid (20.0 g) and ethanol (200 mL) were injected into a 250 mL flask, and after dissolution was completed by stirring, Sulfuric acid (9.6 mL) was slowly dripped at room temperature. Then, reflux stirring was performed for 6 hours or more, and when the reaction was completed, distilled water (150 mL) was dripped slowly, and extraction was performed with ethyl acetate (200 mL). The extracted layers were dried under reduced pressure to obtain the target compound (21.2 g, 93.2%).

[0210] 1 H NMR (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 pharmaceutical composition for preventing or treating metabolic diseases, in which a novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative and at least another active ingredient, which is selected from the group consisting of dipeptidyl peptidase-4 (DPPIV) inhibitor-based, sulfonylurea-based, thiazolidinedione (TZD)-based, biguanide-based, and sodium / glucose cotransporter 2 (SGLT2) inhibitor-based drugs, may be administered in combination or in the form of a composite preparation. The use of the composition of the present invention can provide a remarkably excellent blood sugar reducing effect in various animal diabetic disease models, and the composition of the present invention can be favorably used as a pharmaceutical composition for preventing or treating metabolic diseases, such as obesity, diabetes type I, diabetes type II, glucose intolerance symptoms, insulin resistance symptoms, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia, and syndrome X.

Description

technical field [0001] This patent application claims the priority right of the Korean application right No. 10-2014-0141216 filed with the Korean Patent Office on October 17, 2014, and the disclosure of the patent application is incorporated herein by reference. [0002] The present invention relates to novel 3-(4-(benzyloxy)phenyl)-4-hexenoic acid derivatives which can be obtained by selecting novel 3-(4-(benzyloxy)phenyl)-4-hexenoic acid derivatives and consisting of dipeptidyl peptidase 4 (Dipeptidyl peptidas e-4, DPPIV) inhibitors, sulfonic acid Select at least one other drug from the group consisting of Sulfonylurea, Thiazolidinediones, TZD, Biguanide and sodium / glucose cotransporter 2 inhibitors A pharmaceutical composition for preventing or treating metabolic diseases with active ingredients administered in combination or in the form of a compound. Background technique [0003] Diabetes, as a disease that affects more than 100 million people worldwide, is continuous...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/72C07C59/72C07C59/90C07D217/04C07D211/70C07D295/096C07D211/14C07D209/44C07D413/04C07D271/07C07D277/82C07D239/42C07D213/84C07D207/06A61K31/357A61K31/192A61K31/472A61K31/4418A61K31/495A61K31/506A61K31/4035A61K31/454A61K31/496A61K31/40A61P3/04A61P3/10A61P5/50A61P3/06A61P3/00
CPCA61K31/192A61K31/357A61K31/40A61K31/4035A61K31/4418A61K31/454A61K31/472A61K31/495A61K31/496A61K31/506C07C59/72C07C59/90C07D207/06C07D209/44C07D211/14C07D211/70C07D213/84C07D217/04C07D239/42C07D271/07C07D277/82C07D295/096C07D317/72C07D413/04A61K31/44A61K31/445A61K31/47C07D215/06C07D401/04C07D403/04C07D417/04A61P3/00A61P3/04A61P3/06A61P43/00A61P5/50A61P3/10A61K31/435C07D213/55C07D241/04A61K9/0019A61K9/14A61K9/20A61K9/48A61K45/06
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兑妗李在杰
Owner HYUNDAI PHARMA
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