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Cannabinoid receptor agonist for treating inflammation and synthetic method of cannabinoid receptor agonist

A cannabinoid receptor and synthesis method technology, applied in the directions of anti-inflammatory agents, drug combinations, non-central analgesics, etc., to achieve the effects of easy purchase of raw materials, short production cycle, and simple operation

Inactive Publication Date: 2018-04-06
张玉玲
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, a more complex situation arises in different cell types, other potassium channels, calcium channels, protein kinases A and C, Raf-1, ERK, JNK, p38, c-fos, c-jun, etc. are all possible affected by it

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthetic conditions of 4-(4-methyl-1-naphthylcarboxamide) methyl nicotinate 2 are:

[0028] Mix 4-aminonicotinic acid methyl ester 1 (22 g), 4-methyl-1-naphthoic acid (70 g), triethylamine (44 g), DMAP (7 g), and dichloromethane (120 mL) , stirred at 20 - 80 °C for 12 - 20 hours; added toluene (150 mL) to the system, stirred for 2 - 5 hours, and filtered to obtain methyl 4-(4-methyl-1-naphthylcarboxamide) nicotinate 2 (34g).

[0029] 1 H NMR (400 MHz, DMSO- d6 ) δ = 2.77 (s, 3H), 4.00 (s, 3H), 7.42 (d,1H), 7.55−7.66 (m, 3H), 7.80 (d, 1H), 8.03−8.14 (m, 1H), 8.49 (dd, 1H), 8.53−8.6 (m, 1H), 9.42 (dd, 1H), 11.59 (s, 1H) ppm; m / z (MS-ESI): 321.35 [M + 1] + .

[0030] The synthetic conditions of 4-(4-bromomethyl-1-naphthylcarboxamide) methyl nicotinate 3 are:

[0031] Methyl 4-(4-methyl-1-naphthylcarboxamide) nicotinate 2 (26 g), N - Bromosuccinimide (22 g), benzoyl peroxide (10 g) and chloroform (60 mL) were mixed, stirred at 60 - 120 °C for 1 - 4 hours; cooled...

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Abstract

The invention discloses a cannabinoid receptor agonist 4-(4-((1H-1,2,3-triazole-1-yl)methyl)-1-naphthamide)methyl nicotinate for treating inflammation and a synthetic technology of the cannabinoid receptor agonist. The compound 4-(4-((1H-1,2,3-triazole-1-yl)methyl)-1-naphthamide)methyl nicotinate provided by the invention has good cannabinoid receptor activating activity; meanwhile, the inventionprovides the synthetic technology with simple operation for preparing the cannabinoid receptor agonist 4-(4-((1H-1,2,3-triazole-1-yl)methyl)-1-naphthamide)methyl nicotinate in a large scale, which provides enough 4-(4-((1H-1,2,3-triazole-1-yl)methyl)-1-naphthamide)methyl nicotinate for subsequent pharmaceutical tests.

Description

technical field [0001] The field of the invention belongs to the field of drug synthesis, in particular to a cannabinoid receptor agonist 4-(4-(( 1H -1,2,3-triazol-1-yl)methyl)-1-naphthylcarboxamide)nicotinic acid methyl ester and its synthesis process. Background technique [0002] Cannabinoid receptors are a class of cell membrane receptors in the G protein-coupled receptor superfamily. They are located throughout the body and are part of the endocannabinoid system, which is involved in various physiological processes, including appetite, pain, mood and memory. Like G protein-coupled receptors in general, cannabinoid receptors contain seven transmembrane transmembrane domains. Cannabinoid receptors are activated by three main ligands: endogenous cannabinoids produced by the mammalian body; phytocannabinoids (such as cannabidiol produced by the cannabis plant) and synthetic cannabinoids (such as HU-210). All endocannabinoids and phytocannabinoids are lipophilic, such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61P29/00
CPCC07D401/12
Inventor 张玉玲宋富华王茂盛申钊袁和平
Owner 张玉玲
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