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Composite preparation for preventing or treating metabolic diseases
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A metabolic disease and inhibitor technology, applied in the field of compound preparations for the prevention or treatment of metabolic diseases, can solve the problems of low therapeutic responsiveness and achieve excellent blood sugar lowering effect
Pending Publication Date: 2020-07-17
HYUNDAI PHARMA
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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
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preparation example Construction
[0120] The preparation method of the compound represented by Chemical Formula 1 of the present invention is as follows.
[0121] Preparation method 1
[0122] 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 the compound; and step 2, 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.
[0123] Reaction 1:
[0124] (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).
[0125] Hereinafter, the preparation method of...
preparation example 1
[0204] Preparation of 3-(4-hydroxyphenyl)-4-hexenoic acid ethyl ester
[0205]
[0206] Under a nitrogenatmosphere, 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 completed, distilled water (150 mL) was slowly dripped, and then ethyl acetate (200 mL) was injected to perform extraction. The extracted layers were dried under reduced pressure to obtain the target compound (19.5 g, 85.7%).
[0207] 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
[0208] Preparation of (S)-3-(4-hydroxyphenyl)-4-hexenoic acid ethyl ester
[0209]
[0210] Under a nitrogenatmosphere, (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. After that, reflux stirring was performed for 6 hours or more, and when the reaction was completed, distilled water (150 mL) was slowly dripped, followed by extraction with ethyl acetate (200 mL). The extracted layers were dried under reduced pressure to obtain the target compound (21.2 g, 93.2%).
[0211] 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 remarkablyexcellent 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
[0001] This application was submitted on October 16, 2015. The title of the invention is "Prevention or treatment of metabolic diseases comprising novel 3-(4-(benzyloxy)phenyl)-4-hexenoic acid derivatives and other active ingredients." A divisional application of the invention patent application 201580050675.X. technical field [0002] This patent application claims the priority right of the Korean application right No. 10-2014-0141216 submitted to the Korean Patent Office on October 17, 2014, and the disclosure of the patent application is incorporated into this specification as a reference. [0003] The present invention relates to novel 3-(4-(benzyloxy)phenyl)-4-hexenoic acid derivatives that 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),...
Claims
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