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Phenoxyacetic acid derivatives and preparation method thereof, and application of phenoxyacetic acid derivatives as drug

A technology of acetic acid and alkoxy, applied in the field of pharmacy, can solve the problems of hypoglycemia and weight gain, side effects, edema side effects, etc.

Inactive Publication Date: 2015-10-07
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing methods for the treatment of diabetes all have certain defects.
Examples include insulin injections and sulfonylureas, which may cause hypoglycemia and weight gain; metformin, alpha-glucosidase inhibitors, and GLP-1 analogs, which may cause gastrointestinal side effects; PPAR-γ agonists, which may cause weight gain and edema side effects; DPP-IV inhibitors may cause suprapharyngitis, headache and infection side effects

Method used

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  • Phenoxyacetic acid derivatives and preparation method thereof, and application of phenoxyacetic acid derivatives as drug
  • Phenoxyacetic acid derivatives and preparation method thereof, and application of phenoxyacetic acid derivatives as drug
  • Phenoxyacetic acid derivatives and preparation method thereof, and application of phenoxyacetic acid derivatives as drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] 2-(2-fluoro-4-(2-phenoxyacetylamino)phenoxy)acetic acid (I-1)

[0103]

[0104] first step

[0105] Methyl 2-(4-(2-chloroacetylamino)-2-fluorophenoxy)acetate (1c)

[0106] Methyl 2-fluoro-4-aminophenoxyacetate 1b (2.0 g, 10.1 mmol) was dissolved in CH 2 Cl 2 (50mL), add triethylamine (2.7mL, 20.2mmol) and a catalytic amount of DMAP, cool to 0°C, slowly drop CH 2 Cl 2 Dissolved chloroacetyl chloride 1a (1.5mL, 15.1mmol), reacted at 0°C for 2h, after the reaction was complete by TLC, quenched the reaction by adding water, CH 2 Cl 2 (30ml×4) extraction, the combined organic phases were sequentially washed with 1N NaOH (20ml×1), 1N HCl (20ml×1), saturated NaCl solution (20ml×2), dried, concentrated, and recrystallized with EtOH to obtain 2.2g of a white solid , the yield was 75.9%.

[0107] second step

[0108] Methyl 2-(2-fluoro-4-(2-phenoxyacetamido)phenoxy)acetate (1d)

[0109] Methyl 2-(4-(2-chloroacetamido)-2-fluorophenoxy)acetate 1c (0.20 g, 0.73 mmol) and...

Embodiment 2

[0115] 2-(2-fluoro-4-(2-(o-tolyloxy)acetamide)phenoxy)acetic acid (I-2)

[0116]

[0117] Referring to the preparation method of I-1, 103 mg of white solid was obtained, the yield was 50.4%, and mp: 172-174°C.

[0118] 1 H NMR (300MHz, DMSO-d 6 )δ: 13.02(s, 1H), 10.13(s, 1H), 7.62, 7.58(dd, J=1.8, 13.6Hz, 1H), 7.28(d, J=7.4Hz, 1H), 7.15-7.05(m , 3H), 6.87-6.84(m, 2H), 4.73(s, 2H), 4.68(s, 2H), 2.24(s, 3H); 13 C NMR (75MHz, DMSO-d 6 )δ: 169.84, 166.63, 155.95, 152.44, 141.55, 132.32, 132.19, 126.87, 126.16, 120.94, 118.23, 115.45, 112.13, 109.36, 67.36, 65.24, 16.06 (: ESI-MS2 m / z] - ).

Embodiment 3

[0120] 2-(2-Fluoro-4-(2-(m-tolyloxy)acetamide)phenoxy)acetic acid (I-3)

[0121]

[0122] Referring to the preparation method of I-1, 115 mg of white solid was obtained, the yield was 47.1%, and mp: 157-159°C.

[0123] 1 H NMR (300MHz, DMSO-d 6 )δ: 13.09(s, 1H), 10.09(s, 1H), 7.62, 7.58(dd, J=1.8, 13.6Hz, 1H), 7.31(d, J=8.6Hz, 1H), 7.18(t, J =8.6Hz, 1H), 7.05(t, J=9.3Hz, 1H), 6.83-6.78(m, 3H), 4.73(s, 2H), 4.64(s, 2H), 2.27(s, 3H); 13 C NMR (75MHz, DMSO-d 6 ( - ).

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PUM

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Abstract

The invention relates to novel phenoxyacetic acid derivatives disclosed as general formula (I) and a preparation method thereof, and application of a pharmaceutical composition containing the derivatives for preparing a drug for treating diabetes and metabolic syndrome. The phenoxyacetic acid derivatives have excellent in-vivo activity for lowering blood sugar, and can be used for preventing or treating diabetes.

Description

technical field [0001] The invention relates to the field of pharmacology related to diabetes, in particular to a new phenoxyacetic acid derivative, its preparation method and the application of the pharmaceutical composition containing the derivative in the preparation of medicines for treating diabetes and metabolic syndrome. The derivative structure involved in the present invention has uniqueness and novelty in structural modification of this type of compound. Background technique [0002] Diabetes is a disease of energy metabolism and is divided into type 1 diabetes (insulin-dependent diabetes) and type 2 diabetes (non-insulin-dependent diabetes). At present, there are about 366 million diabetic patients in the world, accounting for 6.4% of the world's population, and type 2 diabetic patients account for about 90-95% of the total number of diabetic patients. [0003] Diabetes can be treated with diet and exercise. When these do not relieve symptoms, medical treatment ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/24C07C231/12A61K31/196A61P3/10A61P3/00
Inventor 黄文龙钱海李政王学堃杨建勇邱倩倩
Owner CHINA PHARM UNIV
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