JP2019501171A5 - - Google Patents
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- JP2019501171A5 JP2019501171A5 JP2018532553A JP2018532553A JP2019501171A5 JP 2019501171 A5 JP2019501171 A5 JP 2019501171A5 JP 2018532553 A JP2018532553 A JP 2018532553A JP 2018532553 A JP2018532553 A JP 2018532553A JP 2019501171 A5 JP2019501171 A5 JP 2019501171A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- chloro
- trifluoromethyl
- methyl
- benzamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 nitro, amino Chemical group 0.000 claims description 308
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 claims description 4
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 4
- XYPGUQJKWJLIIO-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-4-(trifluoromethyl)-5-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(OC(F)(F)F)F)(F)F)C XYPGUQJKWJLIIO-UHFFFAOYSA-N 0.000 claims description 4
- AUCMKUXVMRJOGM-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C AUCMKUXVMRJOGM-UHFFFAOYSA-N 0.000 claims description 4
- PJROJUSMSYNWFE-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,2-trifluoroethoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(F)(F)F)C PJROJUSMSYNWFE-UHFFFAOYSA-N 0.000 claims description 4
- QQWRDBDXPYIEQO-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C QQWRDBDXPYIEQO-UHFFFAOYSA-N 0.000 claims description 4
- HQFJGHZEFNCANX-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5-octafluoropentoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(C(C(C(F)F)(F)F)(F)F)(F)F)C HQFJGHZEFNCANX-UHFFFAOYSA-N 0.000 claims description 4
- WPDNAWPERWCVAS-VIZOYTHASA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[(Z)-1,3,3,3-tetrafluoroprop-1-enoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)O/C(=C/C(F)(F)F)/F)C WPDNAWPERWCVAS-VIZOYTHASA-N 0.000 claims description 4
- NOUPMINKQHIZMS-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[1,1,2-trifluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)ethoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(OC(C(C(F)(F)F)(F)F)(F)F)F)(F)F)C NOUPMINKQHIZMS-UHFFFAOYSA-N 0.000 claims description 4
- HUGKDRZBWLFMLP-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-[2-(trifluoromethoxy)ethoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCCOC(F)(F)F)C HUGKDRZBWLFMLP-UHFFFAOYSA-N 0.000 claims description 4
- SDSDUHGTZHNUNA-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,2,3,3,3-heptafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(C(F)(F)F)(F)F)(F)F)C SDSDUHGTZHNUNA-UHFFFAOYSA-N 0.000 claims description 4
- GACXRNUAQWGTJQ-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C GACXRNUAQWGTJQ-UHFFFAOYSA-N 0.000 claims description 4
- CHRHXFGDTWPFBB-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(C(F)(F)F)F)(F)F)C CHRHXFGDTWPFBB-UHFFFAOYSA-N 0.000 claims description 4
- ZJZOAJGIWQISPN-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-(2,2,3,3,4,4,4-heptafluorobutoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(C(C(F)(F)F)(F)F)(F)F)C ZJZOAJGIWQISPN-UHFFFAOYSA-N 0.000 claims description 4
- MMYPQBCUYZPBKV-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[1,1,2,3,4,4,4-heptafluoro-3-(trifluoromethyl)butoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(C(C(F)(F)F)(C(F)(F)F)F)F)(F)F)C MMYPQBCUYZPBKV-UHFFFAOYSA-N 0.000 claims description 4
- DNQZUAPWECRHCX-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[5-[1,1,2,4,4,4-hexafluoro-3-(trifluoromethyl)but-2-enoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(=C(C(F)(F)F)C(F)(F)F)F)(F)F)C DNQZUAPWECRHCX-UHFFFAOYSA-N 0.000 claims description 4
- BVSLIIPONRIAKT-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3,3-pentafluoropropoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(C(F)(F)F)(F)F)C BVSLIIPONRIAKT-UHFFFAOYSA-N 0.000 claims description 4
- FKRJMLBCQXQBQY-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)C FKRJMLBCQXQBQY-UHFFFAOYSA-N 0.000 claims description 4
- LAEARBAWVDZMQS-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(2,2,3,3,4,4,5,5-octafluoropentoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(C(C(C(F)F)(F)F)(F)F)(F)F)C LAEARBAWVDZMQS-UHFFFAOYSA-N 0.000 claims description 4
- WPZBNEVKHNLITP-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-(5,6,6-trifluorohex-5-enoxy)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCCCCC(=C(F)F)F)C WPZBNEVKHNLITP-UHFFFAOYSA-N 0.000 claims description 4
- KJPMGBPCZCOHDM-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[2-methyl-5-[2-(trifluoromethoxy)ethoxy]-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCCOC(F)(F)F)C KJPMGBPCZCOHDM-UHFFFAOYSA-N 0.000 claims description 4
- REPKAWMAWKEUGQ-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[5-(2,2-difluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(F)F)C REPKAWMAWKEUGQ-UHFFFAOYSA-N 0.000 claims description 4
- VACKVQSLTVHDBG-UHFFFAOYSA-N 2-chloro-N-cyclopropyl-5-[1-[5-[2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OCC(OC(C(OC(F)(F)F)(F)F)(F)F)(F)F)C VACKVQSLTVHDBG-UHFFFAOYSA-N 0.000 claims description 4
- NCEXKWBMKCZBOB-UHFFFAOYSA-N 2-chloro-N-ethyl-5-[1-[5-(1,1,2,3,3,3-hexafluoropropoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NCC)C=C(C=C1)C=1C=NN(C=1)C=1N(N=C(C=1C(F)(F)F)OC(C(C(F)(F)F)F)(F)F)C NCEXKWBMKCZBOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- OYKSWPUJASQFBF-UHFFFAOYSA-N 5-[1-[5-(2-bromo-1,1,2,2-tetrafluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide Chemical compound BrC(C(OC=1C(=C(N(N=1)C)N1N=CC(=C1)C=1C=CC(=C(C(=O)NC2(CC2)C#N)C=1)Cl)C(F)(F)F)(F)F)(F)F OYKSWPUJASQFBF-UHFFFAOYSA-N 0.000 claims description 4
- SZRPEPRPKSCSDM-UHFFFAOYSA-N 5-[1-[5-(2-bromo-1,1,2-trifluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide Chemical compound BrC(C(OC=1C(=C(N(N=1)C)N1N=CC(=C1)C=1C=CC(=C(C(=O)NC2(CC2)C#N)C=1)Cl)C(F)(F)F)(F)F)F SZRPEPRPKSCSDM-UHFFFAOYSA-N 0.000 claims description 4
- NSYVLDMCMITOOE-UHFFFAOYSA-N 5-[1-[5-(2-bromo-1,1,2-trifluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-cyclopropylbenzamide Chemical compound BrC(C(OC=1C(=C(N(N=1)C)N1N=CC(=C1)C=1C=CC(=C(C(=O)NC2CC2)C=1)Cl)C(F)(F)F)(F)F)F NSYVLDMCMITOOE-UHFFFAOYSA-N 0.000 claims description 4
- GPVMFQWTSZTIPX-UHFFFAOYSA-N 5-[1-[5-(2-bromo-1,1-difluoroethoxy)-2-methyl-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]-2-chloro-N-(1-cyanocyclopropyl)benzamide Chemical compound BrCC(OC=1C(=C(N(N=1)C)N1N=CC(=C1)C=1C=CC(=C(C(=O)NC2(CC2)C#N)C=1)Cl)C(F)(F)F)(F)F GPVMFQWTSZTIPX-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- VAAWVIKUWJMYHD-UHFFFAOYSA-N [5-[4-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]pyrazol-1-yl]-1-methyl-4-(trifluoromethyl)pyrazol-3-yl] trifluoromethanesulfonate Chemical compound FC(S(=O)(=O)OC1=NN(C(=C1C(F)(F)F)N1N=CC(=C1)C1=CC(=C(C=C1)Cl)C(NC1(CC1)C#N)=O)C)(F)F VAAWVIKUWJMYHD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 claims description 2
- 125000006017 1-propenyl group Chemical group 0.000 claims description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
- RDHXXUCKODARDZ-UHFFFAOYSA-N 2,3-dichloro-N-cyclopropyl-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C=C1Cl)C=1C=NN(C=1)C=1N(N=C(C=1C)OC(C(C)F)(F)F)C RDHXXUCKODARDZ-UHFFFAOYSA-N 0.000 claims description 2
- NPFGBABJRQOQRK-UHFFFAOYSA-N 2,4-dichloro-N-cyclopropyl-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]benzamide Chemical compound ClC1=C(C(=O)NC2CC2)C=C(C(=C1)Cl)C=1C=NN(C=1)C=1N(N=C(C=1C)OC(C(C)F)(F)F)C NPFGBABJRQOQRK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 claims description 2
- ZIIVGVRBRRQWKO-UHFFFAOYSA-N 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2,4-dimethyl-5-(1,1,2-trifluoropropoxy)pyrazol-3-yl]pyrazol-4-yl]-3-fluorobenzamide Chemical compound ClC1=C(C(=O)NC2(CC2)C#N)C=C(C=C1F)C=1C=NN(C=1)C=1N(N=C(C=1C)OC(C(C)F)(F)F)C ZIIVGVRBRRQWKO-UHFFFAOYSA-N 0.000 claims description 2
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| AU2002361696A1 (en) | 2001-12-17 | 2003-06-30 | Syngenta Participations Ag | Novel corn event |
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| US20050132500A1 (en) | 2003-12-22 | 2005-06-23 | Basf Aktiengesellschaft | Composition for impregnation of fibers, fabrics and nettings imparting a protective activity against pests |
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| DE102005007160A1 (de) | 2005-02-16 | 2006-08-24 | Basf Ag | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
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| WO2012069366A1 (en) | 2010-11-23 | 2012-05-31 | Syngenta Participations Ag | Insecticidal compounds |
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| JP2014510049A (ja) * | 2011-02-09 | 2014-04-24 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫性化合物 |
| UY33895A (es) * | 2011-02-09 | 2012-09-28 | Syngenta Participations Ag | Compuestos insecticidas, método para combatir y controlar insectos, ácaros, nematodos o moluscos, y composición insecticida, acaricida o nematicida |
| KR102001364B1 (ko) | 2011-05-13 | 2019-07-22 | 어레이 바이오파마 인크. | Trka 키나제 저해제로서의 피롤리디닐 유레아 및 피롤리디닐 티오유레아 화합물 |
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| WO2012175474A1 (en) | 2011-06-20 | 2012-12-27 | Syngenta Participations Ag | 1,2,3 triazole pesticides |
| KR20140045542A (ko) | 2011-07-12 | 2014-04-16 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 그에 관한 방법 |
| JP2013256468A (ja) * | 2012-06-13 | 2013-12-26 | Nissan Chem Ind Ltd | 動物の寄生虫防除剤 |
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| RU2712092C2 (ru) | 2013-11-05 | 2020-01-24 | Байер Кропсайенс Акциенгезельшафт | Замещенные бензамиды для борьбы с членистоногими |
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-
2016
- 2016-12-15 US US16/064,916 patent/US10750742B2/en active Active
- 2016-12-15 EP EP16809111.4A patent/EP3393245A1/en not_active Withdrawn
- 2016-12-15 CN CN201680075075.3A patent/CN108463109B/zh active Active
- 2016-12-15 MX MX2018007527A patent/MX2018007527A/es unknown
- 2016-12-15 JP JP2018532553A patent/JP6943857B2/ja active Active
- 2016-12-15 WO PCT/EP2016/081167 patent/WO2017108569A1/en not_active Ceased
- 2016-12-15 CA CA3006911A patent/CA3006911C/en active Active
- 2016-12-15 BR BR112018012926-7A patent/BR112018012926B1/pt active IP Right Grant
-
2018
- 2018-06-19 CO CONC2018/0006320A patent/CO2018006320A2/es unknown
- 2018-06-21 CL CL2018001710A patent/CL2018001710A1/es unknown
- 2018-06-22 EC ECSENADI201847467A patent/ECSP18047467A/es unknown
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