JP2009502948A5 - - Google Patents

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Publication number: JP2009502948A5
Authority: JP; Japan
Prior art keywords: alkyl; optionally substituted; haloalkyl; membered; cycloalkyl
Prior art date: 2006-07-26
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

Application number

JP2008524143A

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English (en)

Japanese (ja)

Other versions

JP5049276B2 (ja

JP2009502948A (ja

Filing date

2006-07-26

Publication date

2009-09-17

2006-07-26 Application filed filed Critical

2006-07-26 Priority claimed from PCT/US2006/029175 external-priority patent/WO2007014290A2/en

2009-01-29 Publication of JP2009502948A publication Critical patent/JP2009502948A/ja

2009-09-17 Publication of JP2009502948A5 publication Critical patent/JP2009502948A5/ja

2012-10-17 Application granted granted Critical

2012-10-17 Publication of JP5049276B2 publication Critical patent/JP5049276B2/ja

Status Expired - Fee Related legal-status Critical Current

2026-07-26 Anticipated expiration legal-status Critical

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-1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 48
125000004093 cyano group Chemical group *C#N 0.000 claims description 43
229910052736 halogen Inorganic materials 0.000 claims description 42
150000002367 halogens Chemical class 0.000 claims description 42
229910052799 carbon Inorganic materials 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 32
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 30
125000005842 heteroatom Chemical group 0.000 claims description 28
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 21
229920006395 saturated elastomer Polymers 0.000 claims description 21
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 20
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 19
125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 19
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 19
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 15
230000000855 fungicidal effect Effects 0.000 claims description 15
125000002619 bicyclic group Chemical group 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 14
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 11
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
150000001204 N-oxides Chemical class 0.000 claims description 10
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 9
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
239000000417 fungicide Substances 0.000 claims description 4
SNRBMGJIULYTAN-GOSISDBHSA-N 2-[1-[2-(2-chlorophenyl)acetyl]piperidin-4-yl]-n-methyl-n-[(1r)-1-phenylethyl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H](C)C=1C=CC=CC=1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CC1=CC=CC=C1Cl SNRBMGJIULYTAN-GOSISDBHSA-N 0.000 claims description 2
230000000844 anti-bacterial effect Effects 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 description 12
150000001721 carbon Chemical group 0.000 description 9
125000004438 haloalkoxy group Chemical group 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
XQBHOLVFZPJNNK-UHFFFAOYSA-N 1-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]pyrazole-3-carboxylic acid Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(N2N=C(C=C2)C(O)=O)CC1 XQBHOLVFZPJNNK-UHFFFAOYSA-N 0.000 description 2
RTUMBXWWAJPWSC-UHFFFAOYSA-N 1-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]pyrazole-4-carboxylic acid Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(N2N=CC(=C2)C(O)=O)CC1 RTUMBXWWAJPWSC-UHFFFAOYSA-N 0.000 description 2
MPELFIVEWZTVKB-UHFFFAOYSA-N 2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]triazole-4-carboxylic acid Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(N2N=C(C=N2)C(O)=O)CC1 MPELFIVEWZTVKB-UHFFFAOYSA-N 0.000 description 2
JDVPUJHPWZGOKG-UHFFFAOYSA-N 2-[4-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperazin-1-yl]-1,3-thiazole-4-carboxylic acid Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCN(C=2SC=C(N=2)C(O)=O)CC1 JDVPUJHPWZGOKG-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 2
SKUPMNMFYNVIBJ-RUZDIDTESA-N 2-[1-[2-(2,5-dichlorophenyl)acetyl]piperidin-4-yl]-n-methyl-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CC1=CC(Cl)=CC=C1Cl SKUPMNMFYNVIBJ-RUZDIDTESA-N 0.000 description 1
QKZDSAALUUROKV-UHFFFAOYSA-N 2-[1-[2-(2,5-dimethylphenyl)acetyl]piperidin-4-yl]-1,3-oxazole-4-carboxylic acid Chemical compound CC1=CC=C(C)C(CC(=O)N2CCC(CC2)C=2OC=C(N=2)C(O)=O)=C1 QKZDSAALUUROKV-UHFFFAOYSA-N 0.000 description 1
FPDZRCHZHOTNMG-UHFFFAOYSA-N 2-[1-[2-(2,5-dimethylphenyl)acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxylic acid Chemical compound CC1=CC=C(C)C(CC(=O)N2CCC(CC2)C=2SC=C(N=2)C(O)=O)=C1 FPDZRCHZHOTNMG-UHFFFAOYSA-N 0.000 description 1
ZSQUEQZILBDXCU-HXUWFJFHSA-N 2-[1-[2-(3,5-dichloropyrazol-1-yl)acetyl]piperidin-4-yl]-n-methyl-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(Cl)C=C1Cl ZSQUEQZILBDXCU-HXUWFJFHSA-N 0.000 description 1
FEWYZVUAJYIABR-HXUWFJFHSA-N 2-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-methyl-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C(F)(F)F FEWYZVUAJYIABR-HXUWFJFHSA-N 0.000 description 1
BPTXHBNOTZOSQU-HXUWFJFHSA-N 2-[1-[2-[5-chloro-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-methyl-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1Cl BPTXHBNOTZOSQU-HXUWFJFHSA-N 0.000 description 1
RBFLPVNBNKDMKF-HSZRJFAPSA-N 2-[1-[2-[5-ethyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-methyl-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CCC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C(=O)N(C)[C@H]2C3=CC=CC=C3CCC2)CC1 RBFLPVNBNKDMKF-HSZRJFAPSA-N 0.000 description 1
OAUOSWMZYFFMKL-UHFFFAOYSA-N 2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carbonyl chloride Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C(Cl)=O)CC1 OAUOSWMZYFFMKL-UHFFFAOYSA-N 0.000 description 1
JZNPWTCYRWYSEY-UHFFFAOYSA-N 2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxylic acid Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C(O)=O)CC1 JZNPWTCYRWYSEY-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
0 CC(*)(*1C=C*C1)NN Chemical compound CC(*)(*1C=C*C1)NN 0.000 description 1
XLMAAYKCVSXVBT-UHFFFAOYSA-N CC1=CC(=NN1CC(=O)N1CCC(CC1)N1N=CC(=C1)C(=O)Cl)C(F)(F)F Chemical compound CC1=CC(=NN1CC(=O)N1CCC(CC1)N1N=CC(=C1)C(=O)Cl)C(F)(F)F XLMAAYKCVSXVBT-UHFFFAOYSA-N 0.000 description 1
RZEYEVFSZQXZPM-UHFFFAOYSA-N CC1=CC(=NN1CC(=O)N1CCC(CC1)N1N=CC(=N1)C(=O)Cl)C(F)(F)F Chemical compound CC1=CC(=NN1CC(=O)N1CCC(CC1)N1N=CC(=N1)C(=O)Cl)C(F)(F)F RZEYEVFSZQXZPM-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
OLTXSYWHXKRGJQ-UHFFFAOYSA-N ethyl 2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2CCN(CC2)C(=O)CN2C(=CC(=N2)C(F)(F)F)C)=N1 OLTXSYWHXKRGJQ-UHFFFAOYSA-N 0.000 description 1
125000000262 haloalkenyl group Chemical group 0.000 description 1
KHIBKVWKDHTSQB-UHFFFAOYSA-N methyl 2-[1-[2-(2,5-dimethylphenyl)acetyl]piperidin-4-yl]-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(C2CCN(CC2)C(=O)CC=2C(=CC=C(C)C=2)C)=N1 KHIBKVWKDHTSQB-UHFFFAOYSA-N 0.000 description 1
FVMGTRCSUFFEOO-UHFFFAOYSA-N n-(2,2-dimethyl-1,3-dihydroinden-1-yl)-n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound C12=CC=CC=C2CC(C)(C)C1N(C)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C FVMGTRCSUFFEOO-UHFFFAOYSA-N 0.000 description 1
KSIOECBVCPYQGX-OAQYLSRUSA-N n-[(1r)-2,3-dihydro-1h-inden-1-yl]-n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C KSIOECBVCPYQGX-OAQYLSRUSA-N 0.000 description 1
ZFMRVPMSGQVVFA-FGZHOGPDSA-N n-[(1r,4r)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2[C@H](O)CC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C ZFMRVPMSGQVVFA-FGZHOGPDSA-N 0.000 description 1
ZFMRVPMSGQVVFA-YADHBBJMSA-N n-[(1r,4s)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2[C@@H](O)CC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C ZFMRVPMSGQVVFA-YADHBBJMSA-N 0.000 description 1
XGVMDGMRIDMICT-HSZRJFAPSA-N n-methyl-1-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrazole-3-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(=N1)C=CN1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C XGVMDGMRIDMICT-HSZRJFAPSA-N 0.000 description 1
UQTUMNOANUXUEN-HSZRJFAPSA-N n-methyl-1-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(=C1)C=NN1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C UQTUMNOANUXUEN-HSZRJFAPSA-N 0.000 description 1
SDGIMKQCTSHABM-UHFFFAOYSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-(4-oxo-2,3-dihydro-1h-naphthalen-1-yl)-1,3-thiazole-4-carboxamide Chemical compound C1CC(=O)C2=CC=CC=C2C1N(C)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C SDGIMKQCTSHABM-UHFFFAOYSA-N 0.000 description 1
JDSXSIAERFOPBZ-JOCHJYFZSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-oxazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=COC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C JDSXSIAERFOPBZ-JOCHJYFZSA-N 0.000 description 1
QKAJPMBNXBFVEW-JOCHJYFZSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carbothioamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=S)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C QKAJPMBNXBFVEW-JOCHJYFZSA-N 0.000 description 1
AHJKPWGTBVOQFA-JOCHJYFZSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C AHJKPWGTBVOQFA-JOCHJYFZSA-N 0.000 description 1
CVBLSRVLRQMKOO-JOCHJYFZSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]triazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(=N1)C=NN1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C CVBLSRVLRQMKOO-JOCHJYFZSA-N 0.000 description 1
BAOIJSKWVPXJRM-OAQYLSRUSA-N n-methyl-2-[4-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperazin-1-yl]-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1N(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C BAOIJSKWVPXJRM-OAQYLSRUSA-N 0.000 description 1
MPXYRZUILSLDQG-GMUIIQOCSA-N n-methyl-2-piperidin-4-yl-n-[(1r)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide;hydrochloride Chemical compound Cl.CN([C@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C1CCNCC1 MPXYRZUILSLDQG-GMUIIQOCSA-N 0.000 description 1
VYOUMGUYZFCSGY-UHFFFAOYSA-N n-methyl-n-(2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound CC1CCC2=CC=CC=C2C1N(C)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C VYOUMGUYZFCSGY-UHFFFAOYSA-N 0.000 description 1
GXGGURAMASLWEJ-CYBMUJFWSA-N n-methyl-n-[(1r)-1-phenylethyl]-2-piperazin-1-yl-1,3-thiazole-5-carboxamide Chemical compound CN([C@H](C)C=1C=CC=CC=1)C(=O)C(S1)=CN=C1N1CCNCC1 GXGGURAMASLWEJ-CYBMUJFWSA-N 0.000 description 1
GVJNYQCKURCIJI-QGZVFWFLSA-N n-methyl-n-[(1r)-1-phenylpropyl]-2-piperidin-4-yl-1,3-thiazole-4-carboxamide Chemical compound CN([C@H](CC)C=1C=CC=CC=1)C(=O)C(N=1)=CSC=1C1CCNCC1 GVJNYQCKURCIJI-QGZVFWFLSA-N 0.000 description 1
VYOUMGUYZFCSGY-SSOJOUAXSA-N n-methyl-n-[(1r,2s)-2-methyl-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2CC[C@@H]1C)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C VYOUMGUYZFCSGY-SSOJOUAXSA-N 0.000 description 1
244000000003 plant pathogen Species 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1

JP2008524143A 2005-07-26 2006-07-26 殺菌・殺カビ性カルボキサミド Expired - Fee Related JP5049276B2 (ja)

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- 2006-07-24 PE PE2006000892A patent/PE20070370A1/es not_active Application Discontinuation
- 2006-07-25 UY UY29695A patent/UY29695A1/es not_active Application Discontinuation
- 2006-07-25 GT GT200600329A patent/GT200600329A/es unknown
- 2006-07-26 ES ES06800387T patent/ES2427153T3/es active Active
- 2006-07-26 EP EP06800387.0A patent/EP1948649B1/en active Active
- 2006-07-26 BR BRPI0615957-5A patent/BRPI0615957A2/pt not_active Application Discontinuation
- 2006-07-26 AR ARP060103219A patent/AR057688A1/es unknown
- 2006-07-26 US US11/988,359 patent/US8586611B2/en not_active Expired - Fee Related
- 2006-07-26 CN CN2006800271007A patent/CN101228156B/zh not_active Expired - Fee Related
- 2006-07-26 WO PCT/US2006/029175 patent/WO2007014290A2/en not_active Ceased
- 2006-07-26 MX MX2008001077A patent/MX2008001077A/es active IP Right Grant
- 2006-07-26 JP JP2008524143A patent/JP5049276B2/ja not_active Expired - Fee Related
- 2006-07-26 NZ NZ564017A patent/NZ564017A/en not_active IP Right Cessation
- 2006-07-26 RS RSP-2008/0027A patent/RS20080027A/sr unknown
- 2006-07-26 KR KR1020087002106A patent/KR101332900B1/ko not_active Expired - Fee Related
- 2006-07-26 ZA ZA200711055A patent/ZA200711055B/xx unknown
- 2006-07-26 RU RU2008106955/04A patent/RU2008106955A/ru not_active Application Discontinuation
- 2006-07-26 AU AU2006272551A patent/AU2006272551B2/en not_active Ceased
- 2006-07-26 PL PL06800387T patent/PL1948649T3/pl unknown
- 2006-07-26 CA CA002614288A patent/CA2614288A1/en not_active Abandoned
2007
- 2007-12-03 IL IL187868A patent/IL187868A0/en unknown
2008
- 2008-01-09 MA MA30560A patent/MA29621B1/fr unknown
- 2008-01-17 EC EC2008008112A patent/ECSP088112A/es unknown
- 2008-01-25 TN TNP2008000041A patent/TNSN08041A1/en unknown

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