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Novel cannabinoid receptor 2 agonist

Technology of a compound, pharmaceutically acceptable salt, in the field of new cannabinoid receptor 2 agonists

Active Publication Date: 2017-01-11
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The diverse clinical application value of CB2 receptor agonists shows its broad prospects in the field of medicine. However, so far, no CB2 receptor agonists have become marketed drugs. Better druggable CB2 receptor agonists are of great significance to this field

Method used

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  • Novel cannabinoid receptor 2 agonist
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  • Novel cannabinoid receptor 2 agonist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0028] The first step: the preparation of 4-[2-(trifluoromethoxy)phenyl]piperidine-1-carbonitrile

[0029]

[0030] Add 4-[2-(trifluoromethoxy)phenyl]piperidine (10.0g, 40.8mmol), potassium carbonate (11.1g, 80.2mmol) to 100mL dichloromethane / water (1:1), Stir and cool to 0°C. Slowly drop cyanobromide (5.3 g, 50.0 mmol) dissolved in 20 mL of dichloromethane into the above solution, react at 0°C for 30 min, return to room temperature and continue the reaction for 2 h, separate the organic layer, and use saturated sodium bicarbonate solution to saturate The organic layer was washed with sodium chloride solution, dried over anhydrous magnesium sulfate, and the organic phase was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography (petroleum ether / ethyl acetate=7 / 3) to obtain 4-[2-(trifluoromethoxy 8.7 g of phenyl]piperidine-1-carbonitrile (yield: 80%).

[0031] 1 H-NMR (400MHz, CDCl 3 ):δ7.12-7.03(m,2H),6.69-6.51(m,2H),3....

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Abstract

The invention relates to an ethylidene coupled piperidinoxadiazole and indole-2-formamide derivative shown as a formula I and / or medicinal salts thereof and a preparation method thereof, as well as a pharmaceutical composition comprising the compound. The compound shown as the formula I is a potential cannabinoid receptor 2(CB2) agonist and can be used for treating and / or preventing diseases such as inflammation, inflammatory bowel diseases, glaucoma, diabetes, nephropathy, cardiomyopathy and the like. The structural formula is as shown in the specification, wherein R1 is aryl and heteroaryl; R2 is H, (C1-C6) linear alkyl or branched alkyl; and R3 is indolyl and substituted indolyl.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a piperidinyl oxadiazole and indole-2-carboxamide compounds and physiologically acceptable salts thereof described in the claims. preparations and their use in the prevention and / or treatment of pain, inflammation, inflammatory bowel disease, glaucoma, diabetes, diabetic retinopathy, atherosclerosis, age-related macular degeneration, acute liver failure, liver fibrosis, pulmonary fibrosis, Renal fibrosis, systemic fibrosis, ischemia-reperfusion injury, acute allograft rejection, chronic allograft nephropathy, diabetic nephropathy, glomerulonephropathy, cardiomyopathy, heart failure, myocardial ischemia, myocardial infarction , systemic sclerosis, thermal injury, burn, hypertrophic scar, gingivitis fever, liver cirrhosis or tumor, osteoporosis, neurodegeneration, stroke and other cannabinoid receptor 2 (CB2) agonist-related diseases. [0002] technical background [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A61K31/454A61P29/00A61P1/00A61P3/10A61P27/06A61P9/10A61P1/16A61P11/00A61P13/12A61P9/04A61P37/02A61P17/02A61P35/00A61P25/28A61P19/10
CPCC07D413/14
Inventor 周立宏
Owner CHENGDU UNIVERSITY OF TECHNOLOGY