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Novel benzoheterocyclic ether derivative, preparation method thereof and application of novel benzoheterocyclic ether derivative in hypoglycemic drugs

A technology of benzoheterocyclic ethers and derivatives, applied in the field of drug synthesis

Inactive Publication Date: 2021-05-18
林剑雄
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Long-term use of traditional hypoglycemic drugs on the market has certain side effects, so it is urgent to find new target drugs to make up for the shortcomings of traditional drugs

Method used

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  • Novel benzoheterocyclic ether derivative, preparation method thereof and application of novel benzoheterocyclic ether derivative in hypoglycemic drugs
  • Novel benzoheterocyclic ether derivative, preparation method thereof and application of novel benzoheterocyclic ether derivative in hypoglycemic drugs
  • Novel benzoheterocyclic ether derivative, preparation method thereof and application of novel benzoheterocyclic ether derivative in hypoglycemic drugs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Synthesis of Intermediate 2:

[0031] Dissolve tert-butyl 4-aminothiocarbonyltetrahydropyridine-1(2H)-carboxylate (4.00g, 16.37mmol) in toluene, add 1,3-dichloroacetone (2.29g, 18.01mmol), and heat up to Reflux reaction, after 8h TLC detects that the reaction is complete, concentrate under reduced pressure to remove toluene, then add 100mL water, extract with 100mL ethyl acetate, wash the organic layer with saturated brine, Na 2 SO 4 Let dry overnight. The desiccant was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4.22 g of the final product with a yield of 81.36%.

[0032] 1 H NMR (400MHz, DMSO-d 6 )δ: 7.64(s, 1H), 4.78(s, 2H), 4.22(t, J=6.5Hz, 2H), 3.22-3.19(m, 1H), 2.91(t, J=12.0Hz, 2H,) ,1.70(dt,J=12.0Hz,3.0Hz,2H),1.40(d,J=5.1Hz,9H).

[0033] Synthesis of Intermediate 3

[0034] Intermediate 2 (4.00g, 12.62mmol) and 5-hydroxybenzothiazole (1.91g, 12.6...

Embodiment 2

[0041]

[0042] 1 H NMR (400MHz, DMSO-d 6 )δ:9.23(s,1H),8.26(s,2H),7.64(s,1H),7.56–7.54(m,2H),7.01(d,J=8.0Hz,1H),5.21(s,2H ), 4.62(d, J=12.4Hz, 2H), 4.25-4.22(m, 1H), 3.06(t, J=12.0Hz, 2H), 2.41(q, J=7.9Hz, 2H), 2.13(d ,J=12.0Hz,2H),1.65-1.62(m,2H),1.14(t,J=7.6Hz,3H).ESI-MS m / z:438.1[M+H] + .

Embodiment 3

[0044]

[0045] 1 H NMR (400MHz, DMSO-d 6 ( d, J=11.0Hz, 2H), 4.24-4.20(m, 1H), 3.03(t, J=12.1Hz, 2H), 2.44(q, J=7.6Hz, 2H), 2.10(d, J=11.2 Hz,2H),1.64-1.62(m,2H),1.15(t,J=7.5Hz,3H).ESI-MS m / z:437.2[M+H] + .

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Abstract

The invention belongs to the technical field of drug synthesis, and particularly relates to a novel benzoheterocyclic ether derivative, a preparation method thereof and application of the novel benzoheterocyclic ether derivative as a GPR119 agonist in hypoglycemic drugs. The MTT experiment shows that the benzoheterocyclic ether derivative synthesized by the research group has the prospect of developing the hypoglycemic drugs.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a novel benzoheterocyclic ether derivative and a preparation method thereof, and its application as a GPR119 agonist in hypoglycemic drugs. Background technique [0002] Diabetes mellitus (DM) is a chronic metabolic disease, which is mainly manifested by abnormal blood sugar levels (hyperglycemia), which in turn causes serious complications in vital organs, blood vessels and nerves. The incidence of diabetes worldwide is increasing year by year, especially in developing countries. According to the report of the International Diabetes Federation (IDF), 415 million people were affected by diabetes in 2017, and it is expected to rise to 629 million in 2045. According to the World Health Organization, diabetes will become the seventh leading cause of death in the world by 2030. The mortality rate of diabetes is highest in Africa, reaching 77.0%, 32.9% in Europe, ...

Claims

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Application Information

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IPC IPC(8): C07D417/14A61P3/10A61K31/506
CPCA61P3/10C07D417/14
Inventor 林剑雄
Owner 林剑雄
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