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Transient receptor potential vanilloid subtype 1 antagonist and its preparation method and use

A technology of thiocyanic acid and hemisulphuric acid, used in anti-inflammatory agents, anesthetics, pharmaceutical formulations, etc., can solve problems such as pain and burning sensation, achieve stable emotions, reduce the number of twists, and increase MPE%.

Active Publication Date: 2019-12-03
重庆美莱德生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds suffer from a number of problems including pain and burning sensation upon initial application

Method used

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  • Transient receptor potential vanilloid subtype 1 antagonist and its preparation method and use
  • Transient receptor potential vanilloid subtype 1 antagonist and its preparation method and use
  • Transient receptor potential vanilloid subtype 1 antagonist and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: preparation compound (1)

[0023] Preparation route:

[0024]

[0025] 3-(2-Oxygen-5-phenyl-2,3-dihydro-1H-benzo[1,4]diazepin-3-yl)propionic acid (a) (0.46g, 1.50mmol) Dissolved in dichloromethane (10ml), sequentially added EDCI (0.31g, 1.64mol), catalytic amount of DMAP and diethylamine (b) (0.11g, 1.62mmol), reacted for 2h, evaporated the solvent under reduced pressure, column Chromatography gave 0.25 g of light yellow solid with a yield of 45.2%. 1 H NMR (300MHz, DMSO-d6) δ: 8.38(d, J=6.5Hz, 2H), 8.29–8.03(m, 2H), 7.82(t, J=7.3Hz, 2H), 7.73–7.42(m, 3H), 6.19(s, 1H), 4.08(t, J=6.6Hz, 1H), 3.74(q, 4H), 2.48(d, J=7.3Hz, 2H), 1.84(s, 3H), 1.00( t,6H); ESI-MS m / z:363.5([M+H] + ).

Embodiment 2

[0026] Embodiment 2: preparation compound (2)

[0027] Preparation route:

[0028]

[0029] 3-(2-Oxygen-5-phenyl-2,3-dihydro-1H-benzo[1,4]diazepin-3-yl)propionic acid (a) (0.46g, 1.50mmol) Dissolved in dichloromethane (10ml), sequentially added EDCI (0.31g, 1.64mol), catalytic amount of DMAP and diisopropylamine (b) (0.16g, 1.62mmol), reacted for 2h, evaporated the solvent under reduced pressure, column Chromatography gave 0.31 g of light yellow solid with a yield of 48.9%. 1 H NMR (300MHz, DMSO-d6) δ: 8.38(d, J=6.5Hz, 2H), 8.29–8.03(m, 2H), 7.82(t, J=7.3Hz, 2H), 7.73–7.42(m, 3H), 6.19(s, 1H), 4.08(t, J=6.6Hz, 1H), 3.88(m, 2H), 2.48(d, J=7.3Hz, 2H), 1.84(s, 3H), 1.39( d,12H); ESI-MS m / z: 392.5 ([M+H] + ).

Embodiment 3

[0030]Embodiment 3: preparation compound (3)

[0031] Preparation route:

[0032]

[0033] 3-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[1,4]diazepine-3-yl)propionic acid (a) (0.50g, 1.62mmol) Dissolve in dichloromethane (10ml), add EDCI (0.34g, 1.78mmol), catalytic amount of DMAP and 1-phenylpiperazine (c) (0.33g, 1.62mmol) successively, react for 2h, evaporate under reduced pressure Solvent, column chromatography, 0.339g of light yellow solid was obtained, the yield was 43.7%. 1 H NMR (300MHz, DMSO-d6)δ:8.52–8.26(m,3H),8.28–8.05(m,2H),7.82(t,J=7.6Hz,2H),7.77–7.49(m,3H), 4.03(t, J=11.8Hz, 1H), 3.64–3.04(m, 8H), 2.89(d, J=5.5Hz, 2H), 2.60(s, 4H); ESI-MS m / z: 482.3([ M+H] + ).

[0034] biological example

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Abstract

The invention discloses a TRPV1 (transient receptor potential vanilloid 1) antagonist which is a compound with a formula (I) in the description, wherein R is selected from -NEt2, -NiPr2 and a component shown in the description. The TRPV1 antagonist can have the analgesia and anesthesia effects while calming down the mood of patients, relieving anxiety of the patients and playing calming and hypnosis activity. The TRPV1 antagonist has remarkable antagonism activity for activating TRPV1 through capsaicin, and the licking time and the writhing times are remarkably reduced as compared with a blank group and the prior art; compared with the blank group, the compound can notably increase MPE% of mice and has the function of relieving thermally induced pain in a hot bath tail flick model for the mice. The preparation method is simple and suitable for industrial production.

Description

technical field [0001] The present invention relates to a novel transient receptor potential vanillic acid subtype 1 antagonist and its pharmaceutically acceptable salt, its preparation method and application. Background technique [0002] Pain is one of the most common clinical symptoms. Due to the complexity of its pathological mechanism, pain has become a major unmet medical need. There are two main types of drugs currently used clinically for analgesia: opioids and nonsteroidal anti-inflammatory drugs (NSAIDs). Opioids bind to and activate opioid receptors, thereby producing analgesic effects. These drugs usually work quickly and can significantly reduce or eliminate pain. However, opioids have side effects: continuous and repeated use will produce drug resistance and lead to addiction, and once the drug is stopped, withdrawal symptoms will appear, which is extremely harmful. The mechanism of action of NSAIDs is to inhibit the biosynthesis of prostaglandins by inhibit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D243/26A61K31/5513A61P25/20A61P23/00A61P29/00
CPCC07D243/26
Inventor 刘颜王娅王林万颖王洪燕
Owner 重庆美莱德生物医药有限公司
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