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5,5-dimethylcyclohexyl-1-ene derivative and application thereof in metabolic diseases

A technology of dimethylcyclohexane and derivatives, applied in the field of medicine, to achieve the effect of great research value

Pending Publication Date: 2020-06-19
邱曲真
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far only 2 TGR5 agonists have carried out clinical research, and there is no marketed drug

Method used

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  • 5,5-dimethylcyclohexyl-1-ene derivative and application thereof in metabolic diseases
  • 5,5-dimethylcyclohexyl-1-ene derivative and application thereof in metabolic diseases
  • 5,5-dimethylcyclohexyl-1-ene derivative and application thereof in metabolic diseases

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] (1) Preparation of 2-bromo-5,5-dimethylcyclohex-1-enylcarbaldehyde

[0027] Add 2.1mL (30.0mmol) of N,N-dimethylformamide into 10mL of chloroform, after cooling down to 0°C, slowly add 2.8mL (27.0mmol) of phosphorus tribromide, continue stirring at 0°C for 2h, then batch 1.3 g (10.0 mmol) of 4,4-dimethylcyclohexanone was added, and the mixture was raised to room temperature for 6 h. TLC detected that the reaction was complete, and the reaction solution was slowly poured into ice water, and the reaction solution was adjusted to pH=7 with sodium bicarbonate. Extract with dichloromethane, combine the organic phases, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. The desiccant was filtered off, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.2 g of light yellow oil with a yield of 54.8%.

[0028] (2) Preparation of 2-(4-fluorophenyl)-5,5-dimethylcyclohex-1-en...

Embodiment 2

[0036]

[0037] 1 H-NMR (400MHz, DMSO-d 6 )δ7.44-7.38(m,2H),7.28(d,J=7.5Hz,2H),7.13-7.04(m,3H),4.36(t,J=7.1Hz,2H),4.10(t,J =7.1Hz, 2H), 2.57–2.52(m, 1H), 2.30-2.28(m, 1H), 1.96~1.92(m, 2H), 1.36(t, J=6.4Hz, 2H), 0.93(s, 6H).MS(ESI)m / z 382.4[M+H] + .

Embodiment 3

[0039]

[0040] 1 H-NMR (400MHz, DMSO-d 6 )δ7.38(d,J=7.4Hz,1H),7.20–7.15(m,3H),7.04-6.96(m,4H),4.36(t,J=7.2Hz,2H),4.07(t,J =7.1Hz, 2H), 2.55–2.52(m, 1H), 2.37(s, 3H), 2.29-2.25(m, 1H), 1.96~1.91(m, 2H), 1.36(t, J=6.4Hz, 2H),0.94(s,6H).MS(ESI)m / z362.2[M+H] + .

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PUM

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Abstract

The invention belongs to the technical field of medicines, provides a 5,5-dimethylcyclohexyl-1-ene derivative with a general formula which is described in the specification and a preparation method thereof, and further discloses an application of the 5,5-dimethylcyclohexyl-1-ene derivative in activation of TGR5 activity and treatment or prevention of diseases related to TGR5 activity regulation.

Description

technical field [0001] The invention belongs to the technical field of medicines, and relates to a 5,5-dimethylcyclohex-1-ene derivative, a preparation method and an application thereof, specifically, the derivative can activate TGR5 activity, and can be used for treatment or prevention of TGR5 activity regulates related diseases. Background technique [0002] TGR-5 is a GPCR on the cell membrane surface, and its endogenous ligand is bile acid. TGR-5 receptors are involved in the regulation of blood glucose homeostasis, immune system, liver and gallbladder function, and gastrointestinal function. The most important and clear one is the regulation of blood glucose homeostasis by TGR-5 receptor. Stimulation of TGR-5 on intestinal secretory cells promotes the secretion of GLP-1, GLP-2 and PYY. GLP-1 can promote blood glucose-dependent insulin release, suppress appetite, slow gastric emptying, etc., thereby maintaining blood glucose homeostasis. GLP-2 mainly maintains the in...

Claims

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Application Information

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IPC IPC(8): C07D265/36C07D215/08C07D241/42A61P3/10A61P9/12A61P3/04A61P3/06A61P1/16
CPCC07D265/36C07D215/08C07D241/42A61P3/10A61P9/12A61P3/04A61P3/06A61P1/16
Inventor 邱曲真
Owner 邱曲真
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