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Benzo six-membered ring derivative as DPP-4 inhibitor and application thereof

A solvate, compound technology, applied in the field of medicinal chemistry, can solve problems such as insufficient insulin secretion

Pending Publication Date: 2021-12-17
SHANDONG BIOPOLAR DICHANG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 4. Dipeptidyl peptidase-IV (DPP-4) is an effective target for the treatment of type 2 diabetes, which can rapidly degrade incretin glucagon-like peptide-1 (GLP-1) and glucose-dependent insulin releasing peptide (GIP) and other important incretins, resulting in insufficient insulin secretion
[0007] 6. However, all currently marketed DPP-4 inhibitors are under patent protection, and there are many new DPP-4 inhibitors in the preclinical research stage

Method used

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  • Benzo six-membered ring derivative as DPP-4 inhibitor and application thereof
  • Benzo six-membered ring derivative as DPP-4 inhibitor and application thereof
  • Benzo six-membered ring derivative as DPP-4 inhibitor and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0120] Embodiment 1. Concrete synthetic method

[0121] Synthesis of 1-methoxy-naphthalene derivatives (8c, 8e, 8g-j)

[0122] 1-methoxy-4-methylsulfonylnaphthalene (8c)

[0123]

[0124] 1-iodo-4-methoxynaphthol (100.00mg, 0.35mmol), sodium methanesulfinate (50.00mg, 0.42mmol), cuprous iodide (7.00mg, 0.10mmol), L-proline Add acid (10.00mg, 0.07mmol), sodium hydroxide (2.80mg, 0.07mmol), anhydrous DMSO (5mL) into a 25mL three-necked reaction flask, protect with nitrogen, heat up to 130°C and stir, TLC monitors the progress of the reaction. After the reaction was completed, cool to room temperature, add 10 mL of water to the reaction system, then extract with ethyl acetate (10 mL×3), wash the organic phase with brine, and then add anhydrous Na 2 SO 4 After drying, purification and separation by silica gel column chromatography (PE:EA=10:1), 73.01 mg of a light yellow product was obtained with a yield of 87.9%.

[0125] 1 H NMR (400MHz, CDCl 3 )δ8.60(dd, J=40.4,26.8Hz,...

Embodiment 2

[0511] Example 2. Biological activity test

[0512] 1. DPP-4 is the extracellular fragment of protease DPP-4 (aa29-766) expressed and purified using the baculovirus expression system Bac-to-Bac. DPP-4 can specifically hydrolyze the substrate Ala-Pro-AMC to generate The product AMC, AMC is excited by 355nm ultraviolet light to produce 460nm emission light, and the linear change of fluorescence value at 460nm wavelength per unit time in dynamic measurement can be displayed as the dipeptidyl peptidase activity of DPP-4.

[0513] 2. Mix the test compound, enzyme and reaction buffer, incubate in the greenhouse for 30 minutes, add the substrate to start the reaction, and continuously measure the change of the fluorescence value at the wavelength of 460nm within 5 minutes. At the same time, a solvent control group in which DMSO was used instead of the test compound, and an alogliptin positive control group were set up. The final reaction volume was 50 μl, and the specific reaction s...

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Abstract

The invention relates to a benzo six-membered ring derivative serving as a DPP-4 inhibitor and application thereof. Specifically, the invention relates to a compound shown in a formula I, a pharmaceutical composition containing the compound shown in the formula I and application of the compound in preparation of drugs for treating DPP-4 related diseases or inhibiting DPP-4.

Description

technical field [0001] The invention relates to the field of medicinal chemistry; specifically, the invention relates to a novel benzo six-membered ring derivative, its synthesis method and its application as a DPP-4 inhibitor in the preparation of medicines for diabetes-related diseases. Background technique [0002] 1. Diabetes is a metabolic disease. The main feature of this disease is the lack of insulin in the body or the decrease in the utilization rate of insulin in the body, which leads to the increase of blood sugar level. If left untreated, diabetes can cause serious damage to the body, such as cardiovascular disease, kidney disease, neurological disease, retinopathy and blindness. According to the report of the International Diabetes Federation (IDF) in 2019, about 463 million adults worldwide suffer from diabetes in 2019, and it is estimated that by 2045, the number of diabetic patients may reach 700 million. In mainland China alone, there are about 116.4 millio...

Claims

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Application Information

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IPC IPC(8): C07D311/92C07D405/10C07D491/052C07D311/04A61P3/10A61P3/08A61P1/00A61P29/00A61P1/04A61P3/04A61P3/00A61K31/352A61K31/5377A61K31/41
CPCC07D311/92C07D405/10C07D491/052C07D311/04A61P3/10A61P3/08A61P1/00A61P29/00A61P1/04A61P3/04A61P3/00
Inventor 李丹李洪林苏明波赵振江罗娜李诗良
Owner SHANDONG BIOPOLAR DICHANG PHARM CO LTD
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