Azetidine-substituted pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2
US-12180196-B2 · Dec 31, 2024 · US
US2018201600A1 · US · A1
| Field | Value |
|---|---|
| Publication number | US-2018201600-A1 |
| Application number | US-201615742369-A |
| Country | US |
| Kind code | A1 |
| Filing date | Jul 4, 2016 |
| Priority date | Jul 6, 2015 |
| Publication date | Jul 19, 2018 |
| Grant date | — |
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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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1 . Compound of formula (I) in which the structural unit of the formula represents a radical A from the group consisting of where these radicals carry m substituents X, X represents a radical 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 from the group consisting of 0, 1 and 2, R represents a radical B from the group consisting of where these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A, Y represents a radical 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 from the group consisting of 0, 1 and 2, W represents CH or N (nitrogen) and R 1 represents a radical from the group consisting of nitro, cyano, CS—NH 2 and CO—CF 3 . 2 . Compound of formula (I) according to claim 1 in which the structural unit of the formula represents a radical A from the group consisting of where these radicals carry m substituents X, X represents a radical 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 from the group consisting of 0, 1 and 2, R represents a radical B from the group consisting of where these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A, Y represents a radical 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 -alkyl thio, 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, where hetaryl is preferably selected from the group consisting of N-pyrazolyl, N-imidazolyl and N-1,2,4-triazolyl, n represents a number from the group consisting of 0, 1 and 2, W represents CH or N (nitrogen) and R 1 represents a radical from the group consisting of nitro, cyano, CS—NH 2 and CO—CF 3 . 3 . Compound of formula (I) according to claim 1 in which the structural unit of the formula represents a radical A from the group consisting of where these radicals carry m substituents X, X represents a radical from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkyl, m represents a number from the group consisting of 0, 1 and 2, R represents a radical B from the group consisting of where these radicals carry n substituents Y and the dashed line represents the bond to the nitrogen atom in radical A, Y represents a radical 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, halo-C 1 -C 4 -alkylsulphonyl, where hetaryl is, for example, N-pyrazolyl, N-imidazolyl or N-1,2,4-triazolyl, n represents a number from the group consisting of 0, 1 and 2, W represents N (nitrogen) and R 1 represents cyano or CO—CF 3 . 4 . Compound of formula (I) according to claim 1 in which the structural unit of the formula represents a radical A from the group consisting of where these radicals carry m substituents X, X represents a radical from the group consisting of fluorine, chlorine, bromine or iodine, cyano, methyl, ethyl, trifluoromethyl and difluoromethyl, m represents a number from the group consisting of 0, 1 and 2, R represents a radical from the group consisting of where these radicals carry n substituents Y and t
Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title
containing three or more hetero rings · CPC title
1,2-Diazines; Hydrogenated 1,2-diazines · CPC title
directly linked by a ring-member-to-ring-member bond · CPC title
1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title
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