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Carbamyl uracil derivative and application thereof

A technology of carbamoyluracil and derivatives, which is applied in the field of carbamoyluracil derivatives, and can solve the problems that anti-inflammatory and analgesic drugs have not been reported yet

Inactive Publication Date: 2016-04-20
XIAMEN INST OF RARE EARTH MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] So far, various types of FAAH inhibitors or NAAA inhibitors have been reported, but anti-inflammatory and analgesic drugs with carbamoyluracil as the core structure and endogenous cannabinoid hydrolase as the therapeutic target have not been reported yet.

Method used

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  • Carbamyl uracil derivative and application thereof
  • Carbamyl uracil derivative and application thereof
  • Carbamyl uracil derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1. compound general synthetic method

[0058] Dissolve uracil derivative (10mmol) and 4-dimethylaminopyridine (0.5mmol) in pyridine (20mL), heat up to 60°C, slowly add isocyanate (20mmol) dropwise, and react at this temperature for 5h. Pyridine was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the product.

Embodiment 2

[0059] Embodiment 2. Synthesis of compound 2.1

[0060] As described in Example 1, compound 2.1 was prepared, and the characterization data were as follows: IR (film) v max :2914,2844,1777,1701,1582,1486,1387cm -1 ; 1 HNMR (400MHz, CDCl 3 )δ0.86(t, J=6.8Hz, 3H), 1.23-1.28(m, 6H), 1.47-1.52(m, 2H), 3.24-3.29(m, 2H), 5.79(d, J=8.4Hz ,1H),8.20(d,J=8.4Hz,1H),9.11(t,J=5.2Hz,1H),11.70(s,1H)ppm; 13 CNMR (100MHz, CDCl 3 )δ14.3,22.5,26.3,29.1,31.3,40.8,104.0,139.2,150.4,152.0,163.3ppm; MS(ESI,m / z):238(M-H) - ;Anal.calcdforC 11 h 17 N 3 o 3 :C,55.22;H,7.16;N,17.56;Found:C,55.06;H,7.15;N,17.59.

Embodiment 3

[0061] Embodiment 3. Synthesis of compound 2.2

[0062] As described in Example 1, compound 2.2 was prepared, and the characterization data were as follows: IR (film) v max :3079,2914,2844,1750,1700,1570,1486,1387cm -1 ; 1 HNMR (400MHz, CDCl 3 )δ0.89(t, J=6.8Hz, 3H), 1.29-1.38(m, 6H), 1.59-1.62(m, 2H), 1.99(d, J=1.2Hz, 3H), 3.35-3.40(m ,2H),8.24(q,J=1.2Hz,1H),8.60(s,1H),9.09(br,1H)ppm; 13 CNMR (100MHz, CDCl 3 )δ12.4,14.0,22.5,26.5,29.2,31.4,41.2,112.3,134.6,150.0,151.5,163.0ppm; MS(ESI,m / z):252(M-H) - ;Anal.calcdforC 12 h 19 N 3 o3 : C, 56.90; H, 7.56; N, 16.59; Found: C, 57.08; H, 7.55; N, 17.02.

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Abstract

The invention discloses a carbamyl uracil derivative and application thereof. The structural formula of the derivative is as shown in the description. The derivative is a novel compound with the endogenous cannabinoid hydrolase inhibiting function, and a new method is provided for inflammation and pain treatment.

Description

technical field [0001] The invention belongs to the technical field of medical organic chemistry, and specifically relates to a carbamoyluracil derivative and an application thereof. Background technique [0002] Tetrahydrocannabinol (Tetrahydrocannabinol, THC for short) acts on receptors of cannabinoid receptor type 1 or type 2 (cannabinoid receptor 1 / 2, CB1 or CB2 for short). The discovery prompted scientists to investigate endogenous ligands for cannabinoid receptors. N-arachidonoyldopamine (N-arachidonoyldopamine) and other endocannabinoids have been found to act on cannabinoid receptors. . Like lipid transmitters such as prostaglandins, these endocannabinoids do not accumulate in the body, but are synthesized locally on demand, and are regulated by enzymes and receptors, and can be metabolized into corresponding cannabinoids by their specific hydrolytic enzymes. Fatty acids and substances such as ethanolamine and glycerin, thereby reducing the effect of such substanc...

Claims

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Application Information

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IPC IPC(8): C07D239/54C07D239/553C07D239/557C07D239/545C07D239/60C07D403/06C07D401/06A61P29/00A61P25/00A61P25/02A61P25/06A61P19/02A61P11/06A61P11/00A61P11/02A61P17/06A61P17/00A61P1/04A61P1/00
CPCC07D239/54C07D239/545C07D239/553C07D239/557C07D239/60C07D401/06C07D403/06
Inventor 李宇航邱彦杨隆河任杰张洋李燕婷陈玲朱程刚卢灿忠
Owner XIAMEN INST OF RARE EARTH MATERIALS
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