JP2012519693A5 - - Google Patents
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- Publication number
- JP2012519693A5 JP2012519693A5 JP2011553063A JP2011553063A JP2012519693A5 JP 2012519693 A5 JP2012519693 A5 JP 2012519693A5 JP 2011553063 A JP2011553063 A JP 2011553063A JP 2011553063 A JP2011553063 A JP 2011553063A JP 2012519693 A5 JP2012519693 A5 JP 2012519693A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- pyrazol
- alkyl
- independently
- difluorophenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 47
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000004432 carbon atoms Chemical group C* 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 12
- -1 cyano, cyanomethyl Chemical group 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 150000002829 nitrogen Chemical group 0.000 claims 12
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004434 sulfur atoms Chemical group 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 6
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatoms Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 4
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 2
- DMBVWPWLMUNZCO-UHFFFAOYSA-N 4-(2,6-difluoro-4-methoxyphenyl)-2,5-dimethyl-N-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C(=CC(F)=CC=2F)F)N(C)N=C1C DMBVWPWLMUNZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- VXXSVCZAHLUQEJ-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-[4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1C(O)C1=CC=C(F)C=C1Br VXXSVCZAHLUQEJ-UHFFFAOYSA-N 0.000 claims 1
- KHQNYTMRFDRULL-UHFFFAOYSA-N (2-chloro-4,6-difluorophenyl)-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1C(O)C1=C(F)C=C(F)C=C1Cl KHQNYTMRFDRULL-UHFFFAOYSA-N 0.000 claims 1
- VYRMNTABYYNYHW-UHFFFAOYSA-N (4-chloro-2,6-difluorophenyl)-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1C(O)C1=C(F)C=C(Cl)C=C1F VYRMNTABYYNYHW-UHFFFAOYSA-N 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- XIUXHKYVNPGCEP-UHFFFAOYSA-N 3-bromo-4-[4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Br XIUXHKYVNPGCEP-UHFFFAOYSA-N 0.000 claims 1
- AWBRZFXUAUARTI-UHFFFAOYSA-N 3-chloro-4-[4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Cl AWBRZFXUAUARTI-UHFFFAOYSA-N 0.000 claims 1
- NTWXHOHUZNUBGG-UHFFFAOYSA-N 3-chloro-4-[4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Cl NTWXHOHUZNUBGG-UHFFFAOYSA-N 0.000 claims 1
- RHXPXUWLNBCVEP-UHFFFAOYSA-N 3-chloro-4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Cl RHXPXUWLNBCVEP-UHFFFAOYSA-N 0.000 claims 1
- GNNSNXJRJGUOFW-UHFFFAOYSA-N 3-chloro-4-[5-(2-chloro-4,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]benzonitrile Chemical compound C=1C=C(C#N)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl GNNSNXJRJGUOFW-UHFFFAOYSA-N 0.000 claims 1
- DKTYKODJDGLPEN-UHFFFAOYSA-N 3-chloro-4-[5-(4-chloro-2,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]benzonitrile Chemical compound C=1C=C(C#N)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F DKTYKODJDGLPEN-UHFFFAOYSA-N 0.000 claims 1
- XICXFPPCHFGZAG-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-2,5-dimethyl-N-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1F XICXFPPCHFGZAG-UHFFFAOYSA-N 0.000 claims 1
- JPULADNQXLGRKU-UHFFFAOYSA-N 4-(2,6-difluoro-4-methoxyphenyl)-N-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C(=CC(F)=CC=2)F)N(C)N=C1C JPULADNQXLGRKU-UHFFFAOYSA-N 0.000 claims 1
- KIULVEFSDWGFEQ-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-2,5-dimethyl-N-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1F KIULVEFSDWGFEQ-UHFFFAOYSA-N 0.000 claims 1
- ICPUBUJYUQMSGY-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-4,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl ICPUBUJYUQMSGY-UHFFFAOYSA-N 0.000 claims 1
- MVCXZBKZESDLBY-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-N-(4-chloro-2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F MVCXZBKZESDLBY-UHFFFAOYSA-N 0.000 claims 1
- CQCKUFBAPXFDHZ-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-2,5-dimethyl-N-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1F CQCKUFBAPXFDHZ-UHFFFAOYSA-N 0.000 claims 1
- VKBIFWCNUMRFAD-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-N-(2,4-dichloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1Cl VKBIFWCNUMRFAD-UHFFFAOYSA-N 0.000 claims 1
- JVBZXENYGMUMPI-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-N-(2,6-dichloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(Cl)C=C(F)C=C1Cl JVBZXENYGMUMPI-UHFFFAOYSA-N 0.000 claims 1
- OJTSHHXIWDLHGO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=CC=C1F OJTSHHXIWDLHGO-UHFFFAOYSA-N 0.000 claims 1
- WLLBTGPVVUDNIM-UHFFFAOYSA-N 4-[4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3-fluorobenzonitrile Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1F WLLBTGPVVUDNIM-UHFFFAOYSA-N 0.000 claims 1
- WXHDEWKACNCFQQ-UHFFFAOYSA-N 4-[4-(2-bromo-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1OC1=C(F)C=C(C#N)C=C1F WXHDEWKACNCFQQ-UHFFFAOYSA-N 0.000 claims 1
- VDBLUBUZHAZTHA-UHFFFAOYSA-N 4-[4-(2-bromo-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1F VDBLUBUZHAZTHA-UHFFFAOYSA-N 0.000 claims 1
- DSMGHOLXQLQVMA-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-2,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=CC(F)=C(C#N)C=C1F DSMGHOLXQLQVMA-UHFFFAOYSA-N 0.000 claims 1
- OFNRVDXZQMDYER-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=C(F)C=C(C#N)C=C1F OFNRVDXZQMDYER-UHFFFAOYSA-N 0.000 claims 1
- RAKKOIQLYSDCJT-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1F RAKKOIQLYSDCJT-UHFFFAOYSA-N 0.000 claims 1
- GQMGMVRAMWNLHW-UHFFFAOYSA-N 4-[5-(2-chloro-4,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]-3-fluorobenzonitrile Chemical compound C=1C=C(C#N)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl GQMGMVRAMWNLHW-UHFFFAOYSA-N 0.000 claims 1
- GQUSTSWMNBDBJG-UHFFFAOYSA-N 4-[5-(4-chloro-2,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]-3-fluorobenzonitrile Chemical compound C=1C=C(C#N)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F GQUSTSWMNBDBJG-UHFFFAOYSA-N 0.000 claims 1
- BXVAVILFNGHERL-UHFFFAOYSA-N 4-[[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]amino]-3,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(C#N)C=C1F BXVAVILFNGHERL-UHFFFAOYSA-N 0.000 claims 1
- KKZUQQVWIKDTJZ-UHFFFAOYSA-N ClC1=C(C=CC(=C1)F)C=1C(=NN(C=1CO)C)C Chemical compound ClC1=C(C=CC(=C1)F)C=1C(=NN(C=1CO)C)C KKZUQQVWIKDTJZ-UHFFFAOYSA-N 0.000 claims 1
- KAEDTPSBWDVHHS-UHFFFAOYSA-N N,4-bis(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Cl KAEDTPSBWDVHHS-UHFFFAOYSA-N 0.000 claims 1
- ZPTPYNOCNLVTNU-UHFFFAOYSA-N N-(2,4-dichloro-6-fluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1Cl ZPTPYNOCNLVTNU-UHFFFAOYSA-N 0.000 claims 1
- FJFIHSRMQYTTPH-UHFFFAOYSA-N N-(2,6-dichloro-4-fluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(Cl)C=C(F)C=C1Cl FJFIHSRMQYTTPH-UHFFFAOYSA-N 0.000 claims 1
- RPQFJJKMVQMNAZ-UHFFFAOYSA-N N-(2,6-dichloro-4-fluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(Cl)C=C(F)C=C1Cl RPQFJJKMVQMNAZ-UHFFFAOYSA-N 0.000 claims 1
- RUVHNVSOOAVPJV-UHFFFAOYSA-N N-(2,6-difluoro-4-methoxyphenyl)-4-(3,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1NC1=C(C=2C=C(F)C(F)=CC=2)C(C)=NN1C RUVHNVSOOAVPJV-UHFFFAOYSA-N 0.000 claims 1
- PWGZAQWMMSWZHI-UHFFFAOYSA-N N-(2-bromo-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br PWGZAQWMMSWZHI-UHFFFAOYSA-N 0.000 claims 1
- VYZCGVAERODZMO-UHFFFAOYSA-N N-(2-bromo-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br VYZCGVAERODZMO-UHFFFAOYSA-N 0.000 claims 1
- OJWPZXSMQGXWDP-UHFFFAOYSA-N N-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br OJWPZXSMQGXWDP-UHFFFAOYSA-N 0.000 claims 1
- IZULPBUDCQEXJP-UHFFFAOYSA-N N-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br IZULPBUDCQEXJP-UHFFFAOYSA-N 0.000 claims 1
- JUZPPCLWIDRLOD-UHFFFAOYSA-N N-(2-bromo-4-fluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Br JUZPPCLWIDRLOD-UHFFFAOYSA-N 0.000 claims 1
- BPNKKYDDFRFQEJ-UHFFFAOYSA-N N-(2-bromo-4-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Br BPNKKYDDFRFQEJ-UHFFFAOYSA-N 0.000 claims 1
- INFARVMXVOIJBK-UHFFFAOYSA-N N-(2-chloro-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl INFARVMXVOIJBK-UHFFFAOYSA-N 0.000 claims 1
- DPNWUIPDHAQECH-UHFFFAOYSA-N N-(2-chloro-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl DPNWUIPDHAQECH-UHFFFAOYSA-N 0.000 claims 1
- NELBALCXLWXLGI-UHFFFAOYSA-N N-(2-chloro-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl NELBALCXLWXLGI-UHFFFAOYSA-N 0.000 claims 1
- HLRSVYVMAUGUEA-UHFFFAOYSA-N N-(2-chloro-4-fluorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C(=CC(F)=CC=2)Cl)N(C)N=C1C HLRSVYVMAUGUEA-UHFFFAOYSA-N 0.000 claims 1
- RXNUUCJQIFQLIM-UHFFFAOYSA-N N-(2-chloro-4-fluorophenyl)-4-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Cl RXNUUCJQIFQLIM-UHFFFAOYSA-N 0.000 claims 1
- QRUJTALPKCMJFC-UHFFFAOYSA-N N-(4-bromo-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Br)C=C1F QRUJTALPKCMJFC-UHFFFAOYSA-N 0.000 claims 1
- CASOODRLVWPKCS-UHFFFAOYSA-N N-(4-bromo-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Br)C=C1F CASOODRLVWPKCS-UHFFFAOYSA-N 0.000 claims 1
- ZPBTUAPAZAPRNV-UHFFFAOYSA-N N-(4-bromo-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Br)C=C1F ZPBTUAPAZAPRNV-UHFFFAOYSA-N 0.000 claims 1
- ZASNAGRZUWHOAF-UHFFFAOYSA-N N-(4-chloro-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F ZASNAGRZUWHOAF-UHFFFAOYSA-N 0.000 claims 1
- LOSLNCQXNBXLLF-UHFFFAOYSA-N N-(4-chloro-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F LOSLNCQXNBXLLF-UHFFFAOYSA-N 0.000 claims 1
- QKEKUMRXLOHZQJ-UHFFFAOYSA-N N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F QKEKUMRXLOHZQJ-UHFFFAOYSA-N 0.000 claims 1
- OPZOZYIDZMWTER-UHFFFAOYSA-N N-(4-chlorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C=CC(Cl)=CC=2)N(C)N=C1C OPZOZYIDZMWTER-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- GNBGNFVTOFWLSA-UHFFFAOYSA-N [4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]-(2,4-difluorophenyl)methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1C(O)C1=CC=C(F)C=C1F GNBGNFVTOFWLSA-UHFFFAOYSA-N 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR075713A1 (es) * | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| TW201245155A (en) | 2010-09-01 | 2012-11-16 | Du Pont | Fungicidal pyrazoles |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| WO2013126283A1 (en) | 2012-02-20 | 2013-08-29 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| EP2864293B1 (en) * | 2012-06-22 | 2016-04-27 | E. I. du Pont de Nemours and Company | Fungicidal 4-methylanilino pyrazoles |
| WO2017156493A1 (en) | 2016-03-11 | 2017-09-14 | Denali Therapeutics Inc. | Compounds, compositions, and methods |
| US20140235689A1 (en) * | 2013-02-20 | 2014-08-21 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| WO2014130241A1 (en) | 2013-02-20 | 2014-08-28 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| US20140288074A1 (en) * | 2013-03-22 | 2014-09-25 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI652012B (zh) * | 2013-05-20 | 2019-03-01 | 杜邦股份有限公司 | 殺真菌吡唑的固態形式 |
| US9961897B2 (en) * | 2013-08-20 | 2018-05-08 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI652014B (zh) * | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| US20170037014A1 (en) | 2014-05-06 | 2017-02-09 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| EP3172190A1 (en) | 2014-07-24 | 2017-05-31 | Bayer CropScience Aktiengesellschaft | Fungicidal pyrazole derivatives |
| WO2016026830A1 (en) * | 2014-08-21 | 2016-02-25 | Bayer Cropscience Aktiengesellschaft | Novel fungicidal pyrazole derivatives |
| US20180042234A1 (en) * | 2015-03-19 | 2018-02-15 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| ES2911341T3 (es) * | 2015-04-29 | 2022-05-18 | The State Of Israel Ministry Of Agriculture & Rural Development Agricultural Res Organization Aro Vo | Composiciones antifitopatogénicas |
| US20180160684A1 (en) * | 2015-06-01 | 2018-06-14 | Ishihara Sangyo Kaisha, Ltd. | Fungicide composition and plant disease control method |
| US11214565B2 (en) | 2015-11-20 | 2022-01-04 | Denali Therapeutics Inc. | Compound, compositions, and methods |
| PE20240221A1 (es) | 2016-06-16 | 2024-02-16 | Denali Therapeutics Inc | Pirimidin-2-ilamino-1h-pirazoles como inhibidores de lrrk2 para el uso en el tratamiento de trastornos neurodegenerativos |
| WO2018052838A1 (en) | 2016-09-16 | 2018-03-22 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| CN107286097B (zh) | 2017-07-13 | 2019-06-25 | 青岛清原化合物有限公司 | 双唑草酮c晶型及其制备方法和用途 |
| TW202400547A (zh) | 2018-09-06 | 2024-01-01 | 美商富曼西公司 | 殺真菌之經硝苯胺基取代之吡唑 |
| WO2020056090A1 (en) * | 2018-09-14 | 2020-03-19 | Fmc Corporation | Fungicidal halomethyl ketones and hydrates |
| TW202200012A (zh) | 2020-03-11 | 2022-01-01 | 美商富曼西公司 | 殺真菌劑混合物 |
| CN113549053B (zh) * | 2020-04-23 | 2022-09-13 | 沈阳中化农药化工研发有限公司 | 一种吡唑喹（唑）啉醚类化合物及其应用 |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| NL7812293A (nl) | 1977-12-23 | 1979-06-26 | Montedison Spa | Fosforzuur en thiofosforzuuresters van 5(3)-hydroxypyrazolen met insecticide werking. |
| GB2054555A (en) * | 1979-07-27 | 1981-02-18 | Abbott Lab | Pyrazolyl amino imidazolines |
| GB2076801A (en) * | 1980-04-14 | 1981-12-09 | Erba Farmitalia | alpha , beta -Disubstituted Acrylamido Cephalosporins |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| JPH01319478A (ja) * | 1988-06-20 | 1989-12-25 | Mitsui Toatsu Chem Inc | 免疫調節作用を有する化合物 |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| ATE208560T1 (de) | 1989-08-30 | 2001-11-15 | Kynoch Agrochemicals Proprieta | Herstellung eines dosierungsmittels |
| JPH05504964A (ja) | 1990-03-12 | 1993-07-29 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 熱―活性化結合剤からの水分散性又は水溶性有害生物防除剤顆粒 |
| US5189040A (en) * | 1990-05-28 | 1993-02-23 | Sumitomo Chemical Company, Limited | Pyrazole derivatives, method for producing the same and agricultural and/or horticultural fungicides containing the same as active ingredient |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| FR2676057B1 (fr) * | 1991-05-02 | 1995-03-03 | Therapeutique Moder Lab | Derives de 1,2-dithiole-3-thione, procede de preparation de ces derives, ainsi que l'utilisation de ces derives comme intermediaires de synthese ou comme medicaments. |
| FR2682379B1 (fr) | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
| AU3934693A (en) * | 1992-03-26 | 1993-10-21 | Dowelanco | N-heterocyclic nitro anilines as fungicides |
| JPH0665237A (ja) * | 1992-05-07 | 1994-03-08 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| EP0698013B1 (en) | 1993-05-12 | 2001-10-04 | E.I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| JPH0816059B2 (ja) * | 1993-05-21 | 1996-02-21 | 三井東圧化学株式会社 | 免疫調節剤 |
| DE4405207A1 (de) * | 1994-02-18 | 1995-08-24 | Bayer Ag | N-Pyrazolylaniline und N-Pyrazolylaminopyridine |
| JPH08208620A (ja) * | 1995-02-03 | 1996-08-13 | Takeda Chem Ind Ltd | アミノピラゾール誘導体、その製造法および用途 |
| EP0836602B1 (en) | 1995-07-05 | 2002-01-30 | E.I. Du Pont De Nemours And Company | Fungicidal pyrimidinones |
| JPH09208620A (ja) | 1996-02-02 | 1997-08-12 | Sumitomo Bakelite Co Ltd | 硬化性エラストマー及びその製造方法 |
| DK0888359T3 (da) | 1996-03-11 | 2002-08-12 | Syngenta Participations Ag | Pyrimidin-4-on-derivat som pesticid |
| AU7726898A (en) * | 1997-05-22 | 1998-12-11 | G.D. Searle & Co. | Pyrazole derivatives as p38 kinase inhibitors |
| GB9719411D0 (en) | 1997-09-12 | 1997-11-12 | Ciba Geigy Ag | New Pesticides |
| JP2000095778A (ja) * | 1998-09-28 | 2000-04-04 | Ube Ind Ltd | ピラゾール誘導体、その製造法及び農園芸用の殺菌剤 |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| TWI283164B (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| AR042067A1 (es) | 2002-11-27 | 2005-06-08 | Bayer Pharmaceuticals Corp | Derivados de anilinopirazol utiles en el tratamiento de la diabetes |
| GB0315657D0 (en) * | 2003-07-03 | 2003-08-13 | Astex Technology Ltd | Pharmaceutical compounds |
| US7517998B2 (en) | 2004-06-01 | 2009-04-14 | Boehringer Ingelheim International Gmbh | Non nucleoside reverse transcriptase inhibitors |
| WO2007027842A1 (en) | 2005-08-31 | 2007-03-08 | Bayer Healthcare Llc | Anilinopyrazole derivatives useful for the treatment of diabetes |
| CN101505747A (zh) | 2006-06-21 | 2009-08-12 | 杜邦公司 | 作为细胞增殖抑制剂的吡嗪酮 |
| WO2008093639A1 (ja) * | 2007-01-29 | 2008-08-07 | Takeda Pharmaceutical Company Limited | ピラゾール化合物 |
| PE20091953A1 (es) | 2008-05-08 | 2010-01-09 | Du Pont | Azoles sustituidos como fungicidas |
| AR075713A1 (es) * | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| WO2011051958A1 (en) | 2009-10-30 | 2011-05-05 | E.I. Du Pont De Nemours And Company | Fungicidal pyrazolones |
| TW201117722A (en) | 2009-11-04 | 2011-06-01 | Du Pont | Fungicidal mixtures |
| WO2012023143A1 (en) | 2010-08-19 | 2012-02-23 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TW201245155A (en) | 2010-09-01 | 2012-11-16 | Du Pont | Fungicidal pyrazoles |
| AU2011307289A1 (en) | 2010-09-29 | 2013-02-21 | E. I. Du Pont De Nemours And Company | Fungicidal imidazoles |
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