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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| WO2002015701A2 (en) | 2000-08-25 | 2002-02-28 | Syngenta Participations Ag | Bacillus thuringiensis crystal protein hybrids |
| WO2003000906A2 (en) | 2001-06-22 | 2003-01-03 | Syngenta Participations Ag | Plant disease resistance genes |
| US7230167B2 (en) | 2001-08-31 | 2007-06-12 | Syngenta Participations Ag | Modified Cry3A toxins and nucleic acid sequences coding therefor |
| DE60205767D1 (de) | 2001-10-25 | 2005-09-29 | Siamdutch Mosquito Netting Co | Behandlung von geweben mit einem insektizid |
| 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 |
| DE102004023894A1 (de) | 2004-05-12 | 2005-12-08 | Basf Ag | Verfahren zur Behandlung von flexiblen Substraten |
| KR20070067165A (ko) | 2004-10-13 | 2007-06-27 | 피티씨 테라퓨틱스, 인크. | 넌센스 변이 억제용 화합물, 및 이의 사용 방법 |
| DE102005007160A1 (de) | 2005-02-16 | 2006-08-24 | Basf Ag | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| DE102005020889A1 (de) | 2005-05-04 | 2006-11-09 | Fritz Blanke Gmbh & Co.Kg | Verfahren zur antimikrobiellen Ausrüstung von textilen Flächengebilden |
| MX2007015020A (es) | 2005-06-03 | 2008-01-17 | Basf Ag | Composicion para la impregnacion de fibras, telas y mallas que comparte una actividad protectora contra plagas. |
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| EP1984555B1 (de) | 2006-02-03 | 2016-05-11 | Basf Se | Verfahren zum behandeln von textilen substraten |
| AU2007341232B2 (en) | 2006-12-29 | 2013-01-31 | AbbVie Deutschland GmbH & Co. KG | Carboxamide compounds and their use as calpain inhibitors |
| EP2152270B1 (en) | 2007-06-08 | 2015-03-04 | Janssen Pharmaceutica, N.V. | Piperidine/piperazine derivatives |
| JP5230731B2 (ja) | 2007-06-12 | 2013-07-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 害虫からの保護活性を付与するための非生物材料への含浸用水性製剤及び含浸方法 |
| CN101821239B (zh) | 2007-10-18 | 2014-01-01 | 组合化学工业株式会社 | 3-烷氧基-1-苯基吡唑衍生物及有害生物防除剂 |
| EP2294062B1 (en) | 2008-06-09 | 2013-08-21 | Bayer Intellectual Property GmbH | Substituted 4- (indazolyl) -1,4-dihydropyridines and methods of use thereof |
| EP2184273A1 (de) * | 2008-11-05 | 2010-05-12 | Bayer CropScience AG | Halogen-substituierte Verbindungen als Pestizide |
| DE102009003975A1 (de) | 2009-01-07 | 2010-07-08 | Merck Patent Gmbh | Benzothiazolonderivate |
| DE102009003954A1 (de) | 2009-01-07 | 2010-07-08 | Merck Patent Gmbh | Pyridazinonderivate |
| EP2253617A1 (de) | 2009-05-20 | 2010-11-24 | Bayer CropScience AG | Halogen-substituierte Verbindungen als Pestizide |
| US8080541B2 (en) | 2009-08-27 | 2011-12-20 | Hoffman-La Roche Inc. | Carbocyclic GlyT-1 receptor antagonists |
| WO2011088181A1 (en) | 2010-01-13 | 2011-07-21 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
| JP5743418B2 (ja) * | 2010-04-09 | 2015-07-01 | Ｏａｔアグリオ株式会社 | 新規なピラゾール化合物、その製造方法及び有害生物防除剤 |
| JP5815029B2 (ja) | 2010-07-09 | 2015-11-17 | クオンベルゲンセ プハルマセウトイカルス リミテッド | カルシウムチャネル遮断薬としてのテトラゾール化合物 |
| EP2643302A1 (en) | 2010-11-23 | 2013-10-02 | Syngenta Participations AG | Insecticidal compounds |
| TWI528899B (zh) | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| MX2013009067A (es) * | 2011-02-09 | 2013-10-01 | Syngenta Participations Ag | Compuestos insecticidas. |
| 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 |
| BR112013029201B1 (pt) | 2011-05-13 | 2022-08-09 | Array Biopharma Inc | Compostos de pirrolidinil ureia e pirrolidinil tioureia, seu processo de preparação, seu uso e composições farmacêuticas |
| JP6007417B2 (ja) | 2011-05-31 | 2016-10-12 | レセプトス エルエルシー | 新規ｇｌｐ−１受容体安定剤および調節剤 |
| 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 |
| CA2900029C (en) * | 2013-02-06 | 2021-03-02 | Bayer Cropscience Aktiengesellschaft | Halogen-substituted pyrazol derivatives as pest-control agents |
| LT3066080T (lt) | 2013-11-05 | 2018-09-10 | Bayer Cropscience Aktiengesellschaft | Nauji junginiai kovai su artropodais |
| WO2015067648A1 (de) | 2013-11-05 | 2015-05-14 | Bayer Cropscience Ag | Neue verbindungen zur bekämpfung von arthropoden |
| AR101816A1 (es) | 2014-04-02 | 2017-01-18 | Bayer Cropscience Ag | Derivados de 3-[(pirazol-5-il)-heteroaril]-benzamidas como agentes pesticidas |
-
2016
- 2016-12-15 US US16/064,916 patent/US10750742B2/en active Active
- 2016-12-15 JP JP2018532553A patent/JP6943857B2/ja active Active
- 2016-12-15 BR BR112018012926-7A patent/BR112018012926B1/pt active IP Right Grant
- 2016-12-15 CN CN201680075075.3A patent/CN108463109B/zh active Active
- 2016-12-15 MX MX2018007527A patent/MX2018007527A/es unknown
- 2016-12-15 WO PCT/EP2016/081167 patent/WO2017108569A1/en not_active Ceased
- 2016-12-15 EP EP16809111.4A patent/EP3393245A1/en not_active Withdrawn
- 2016-12-15 CA CA3006911A patent/CA3006911C/en active Active
-
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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