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Novel heterocyclic amide piperidine derivative as well as preparation method and application thereof in hypoglycemic drugs

A kind of technology of heterocyclic amide piperidine and derivatives, applied in the field of drug synthesis

Inactive Publication Date: 2021-08-13
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 heterocyclic amide piperidine derivative as well as preparation method and application thereof in hypoglycemic drugs
  • Novel heterocyclic amide piperidine derivative as well as preparation method and application thereof in hypoglycemic drugs
  • Novel heterocyclic amide piperidine derivative as well as preparation method and application thereof in hypoglycemic drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of Example 1

[0030]

[0031] Synthesis of Intermediate 2:

[0032] Dissolve 4-aminothiocarbonyltetrahydropyridine-1(2H)-carboxylic acid tert-butyl ester (3.00g, 12.28mmol) and 1,3-dichloroacetone (1.71g, 13.51mmol) in toluene, heat up to Reflux reaction, after 10h TLC detects that the reaction is complete, concentrate under reduced pressure to remove toluene, then add 100mL ethyl acetate for extraction, wash the organic layer with water and saturated brine respectively, anhydrous Na 2 SO 4 Let dry overnight. The desiccant was filtered off, the solvent was evaporated by concentration under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 3.01 g of the final product with a yield of 77.38%. 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] Intermed...

Embodiment 2

[0041]

[0042] 1 H NMR (400MHz, DMSO-d 6 )δ: 8.54(d, J=8.4Hz, 2H), 8.30(d, J=8.0Hz, 1H), 8.15(d, J=1.4Hz, 1H), 7.99-7.95(m, 3H), 7.64( s,1H),7.01(d,J=7.8Hz,1H),6.24(d,J=8.1Hz,1H),5.21(s,2H),4.23(d,J=12.1Hz,2H),3.40( s,3H),3.21-3.18(m,1H),2.90(t,J=12.0Hz,2H),1.76-1.71(m,2H).ESI-MS m / z:525.1[M+H] + .

Embodiment 3

[0044]

[0045] 1 H NMR (400MHz, DMSO-d 6 )δ:8.57-8.54(m,3H),8.14(d,J=2.4Hz,1H),7.98-7.94(m,3H),7.64(s,1H),7.30(d,J=8.0Hz,1H ),7.02(d,J=7.9Hz,1H),5.20(s,2H),4.24(d,J=12.1Hz,2H),3.38(s,3H),3.20-3.17(m,1H),2.91 (t,J=12.4Hz,2H),1.76-1.72(m,2H).ESI-MS m / z:541.1[M+H] + .

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Abstract

The invention belongs to the technical field of drug synthesis, and particularly relates to a novel heterocyclic amide piperidine derivative and a preparation method thereof, and application of the derivative as a GPR119 agonist in hypoglycemic drugs. An MTT experiment shows that the novel heterocyclic amide piperidine 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 heterocyclic amide piperidine 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 Eu...

Claims

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Application Information

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