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Benzimidazole derivative and preparation method and application as medicine thereof

A drug, benzo technology, applied in the field of pharmacology, can solve problems such as single action

Active Publication Date: 2019-03-12
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of drug treatment of metabolic syndrome, the hypoglycemic drugs or lipid-lowering drugs currently used in clinical practice have a single effect, and none of them have an ideal effect on improving various pathological indicators of metabolic syndrome. Metabolic syndrome drug research is underway to bring new, safer and more effective drugs to patients with metabolic syndrome

Method used

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  • Benzimidazole derivative and preparation method and application as medicine thereof
  • Benzimidazole derivative and preparation method and application as medicine thereof
  • Benzimidazole derivative and preparation method and application as medicine thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] 2-Methyl-2-(2-methyl-4-(6-methyl-1H-benzo[d]imidazol-2-yl)phenoxy)propanoic acid (I-1)

[0068]

[0069] first step

[0070] Methyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate (2a)

[0071] Dissolve 3-methyl-4-hydroxybenzaldehyde 1a (1.0g, 7.35mmol) and methyl 2-bromoisobutyrate (4.0g, 22.1mmol) in acetonitrile (20mL), add potassium carbonate (3.0g, 22.1mmol), reacted at 50°C for 12h, after TLC detected that the reaction was complete, added water to dissolve the solid mixture in the reaction, extracted with ethyl acetate (30mL×4), combined the organic phases with water (20mL×1), 1NHCl (20mL×1 ), washed with saturated NaCl solution (20mL×2), dried, concentrated, and the resulting product was directly used in the next reaction without purification.

[0072] second step

[0073] Methyl 2-methyl-2-(2-methyl-4-(6-methyl-1H-benzo[d]imidazol-2-yl)phenoxy)propanoate (3a)

[0074] Dissolve 2a (0.5g, 2.12mmol) and 3,4-diaminotoluene (0.29g, 2.12mmol) in DMF (15mL) with...

Embodiment 2

[0080] 2-Methyl-2-(2-methyl-4-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)phenoxy)propanoic acid (I-2)

[0081]

[0082] Referring to the preparation method of I-1, 1.5 g of white solid was obtained with a yield of 43%.

[0083] 1 H NMR (300MHz, D 2 O) δ: 10.67-10.44(m, 2H), 10.26(s, 1H), 10.17(d, J=8.5Hz, 1H), 10.00(d, J=8.5Hz, 1H), 9.09(d, J= 8.7Hz, 1H), 5.37(s, 1H), 4.47(s, 3H), 3.84(s, 6H). 13 C NMR (75MHz, DMSO-d 6 )δ: 174.87, 158.57, 151.79, 135.46, 132.90, 131.31, 129.53, 128.01, 126.47, 126.05, 125.62, 122.27, 115.79, 115.35, 111.67, 79.69, 25.60, 137.87 m.z [ES-MS] m.z - .Anal.calcd.For C 19 h 17 f 3 N 2 o 3 : C, 60.32; H, 4.53; N, 7.40; Found: C, 60.15; H, 4.38; N, 7.52.

Embodiment 3

[0085] 2-(2-fluoro-4-(6-methyl-1H-benzo[d]imidazol-2-yl)phenoxy)-2-methylpropanoic acid (I-3)

[0086]

[0087] Referring to the preparation method of I-1, 0.29 g of white solid was obtained with a yield of 49%.

[0088] 1 H NMR (300MHz, D 2 O) δ: 10.74-10.57(m, 1H), 10.44(d, J=8.7Hz, 1H), 9.89(d, J=8.4Hz, 1H), 9.80(s, 1H), 9.56(d, J= 8.4Hz, 1H), 9.38(t, J=8.6Hz, 1H), 5.37(s, 1H), 4.69(s, 3H), 3.85(s, 6H). 13 C NMR (75MHz, DMSO-d 6 )δ: 174.23, 147.62, 147.38, 136.27, 132.54, 130.41, 127.75, 125.41, 119.85, 116.52, 113.90, 113.69, 81.16, 25.43, 21.64. ESI-MS m / z: 327.1 [M-H] - .Anal.calcd.For C 18 h 17 FN 2 o 3 : C, 65.85; H, 5.22; N, 8.53; Found: C, 65.67; H, 5.35; N, 8.58.

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Abstract

The invention relates to a novel benzimidazole PPAR alpha / gamma / delta panto-agonist as shown in the general formula (I) and a preparation method thereof and application of a medicine compound containing the derivative in preparing a medicine for preventing or / and treating abnormal glucose metabolism or / and abnormal lipids metabolism disease. The PPAR alpha / gamma / delta panto-agonist has excellent in-vivo hypoglycemic activity and blood fat adjusting action, can be applied for preparing medicines for preventing or / and treating metabolic syndrome related diseases of diabetes, obesity, hyperlipidemia, atherosclerosis, fatty liver and the like, and has wide application prospects.

Description

technical field [0001] The present invention relates to the field of pharmacy related to glucose and lipid metabolic diseases, in particular to a new benzimidazole derivative, its preparation method and a pharmaceutical composition containing the derivative as a drug for the preparation of glucose and lipid metabolic diseases Applications. The derivative structures involved in the present invention are unique and novel in this field. Background technique [0002] Metabolic syndrome is a common disease characterized by abnormal glucose and lipid metabolism, accompanied by elevated low-density lipoprotein and low high-density lipoprotein cholesterol. The common symptoms are obesity, diabetes, hyperlipidemia, atherosclerosis Cirrhosis and fatty liver, etc. Among them, diabetic patients often have hyperlipidemia, cardiovascular disease, diabetic nephropathy, diabetic neuropathy and other diseases. [0003] According to the World Health Organization, more than 220 million peopl...

Claims

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Application Information

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IPC IPC(8): C07D235/18A61K31/4184A61P3/10A61P3/04A61P3/06A61P9/10A61P3/00A61P1/16
CPCA61P1/16A61P3/00A61P3/04A61P3/06A61P3/10A61P9/10C07D235/18
Inventor 李政张陆勇刘柔佳
Owner GUANGDONG PHARMA UNIV
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