Azetidine-substituted pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2
US-12180196-B2 · Dec 31, 2024 · US
US10239859B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10239859-B2 |
| Application number | US-201615742369-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 4, 2016 |
| Priority date | Jul 6, 2015 |
| Publication date | Mar 26, 2019 |
| Grant date | Mar 26, 2019 |
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The present application relates to novel heterocyclic compounds, to processes and intermediates for the preparation thereof, and their use for controlling animal pests.
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The invention claimed is: 1. A compound of formula (I) wherein the structural unit of the formula represents a radical A selected from the group consisting of wherein these radicals carry m substituents X, X represents a radical selected from the group consisting of halogen, cyano (CN), nitro, alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulphonyl, alkoxycarbonyl, alkylcarbonyl and cycloalkylcarbonyl, m represents a number selected from the group consisting of 0, 1 and 2, R represents a radical B selected from the group consisting of wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A, Y represents a radical selected from the group consisting of halogen, cyano, nitro, amino, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkoxycarbonyl, alkylcarbonyl, cycloalkylcarbonyl, alkylamino, dialkylamino, alkylaminosulphonyl, dialkylaminosulphonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxyalkylcarbonylamino, haloalkylcarbonylamino and in each case optionally substituted aryl and hetaryl, n represents a number selected from the group consisting of 0, 1 and 2, W represents CH or N (nitrogen) and R 1 represents a radical selected from the group consisting of nitro, cyano, CS—NH 2 and CO—CF 3 . 2. The compound of formula (I) according to claim 1 wherein the structural unit of the formula represents a radical A selected from the group consisting of wherein these radicals carry m substituents X, X represents a radical selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, halo-C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl and C 3 -C 6 -cycloalkylcarbonyl, m represents a number selected from the group consisting of 0, 1 and 2, R represents a radical B selected from the group consisting of wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A, Y represents a radical selected from the group consisting of halogen, cyano, nitro, amino, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halo-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, halo-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, halo-C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 1 -C 4 -alkylaminosulphonyl, di-(C 1 -C 4 -alkyl)aminosulphonyl, C 1 -C 4 -alkylaminocarbonyl, di-(C 1 -C 4 -alkyl)aminocarbonyl, C 1 -C 4 -alkylcarbonylamino, C 1 -C 4 -alkoxy-C 1 -C 4 -alkylcarbonylamino, halo-C 1 -C 4 -alkylcarbonylamino, in each case optionally substituted aryl and 5- or 6-membered hetaryl and in the case of aryl and hetaryl in particular in each case optionally halogen-, cyano-, C 1 -C 4 -alkyl-, halo-C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, halo-C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, halo-C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl-, halo-C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or halo-C 1 -C 4 -alkylsulphonyl-substituted phenyl and 5- or 6-membered hetaryl, wherein hetaryl is preferably selected from the group consisting of N-pyrazolyl, N-imidazolyl and N-1,2,4-triazolyl, n represents a number selected from the group consisting of 0, 1 and 2, W represents CH or N (nitrogen) and R 1 represents a radical selected from the group consisting of nitro, cyano, CS—NH 2 and CO—CF 3 . 3. The compound of formula (I) according to claim 1 wherein the structural unit of the formula represents a radical A selected from the group consisting of wherein these radicals carry m substituents X, X represents a radical selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, and halo-C 1 -C 4 -alkyl, m represents a number selected from the group consisting of 0, 1 and 2, R represents a radical B selected from the group consisting of wherein these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A, Y represents a radical selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halo-C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, halo-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, halo-C 1 -C 4 -alkylsulphonyl and 5-membered hetaryl which is optionally substituted by a substituent from the group consisting of halogen, cyano, C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halo-C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halo-C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, halo-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, and halo-C 1 -C 4 -alkylsulphonyl, n represents a number selected from the group consisting of 0, 1 and 2, W represents N (nitrogen) and R 1 represents cyano or CO—CF 3 . 4. The compound of formula (I) according to claim 1 wherein the structural unit of the formula represents a radical A selected from the group consisting of wherein these radicals carry m substituents X, X represents a radical selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl,
1,2-Diazines; Hydrogenated 1,2-diazines · CPC title
containing three or more hetero rings · CPC title
characterised by the surfactants · CPC title
Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title
1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title
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