JP2011503006A - 殺菌性複素環アミン - Google Patents
殺菌性複素環アミン Download PDFInfo
- Publication number
- JP2011503006A JP2011503006A JP2010532330A JP2010532330A JP2011503006A JP 2011503006 A JP2011503006 A JP 2011503006A JP 2010532330 A JP2010532330 A JP 2010532330A JP 2010532330 A JP2010532330 A JP 2010532330A JP 2011503006 A JP2011503006 A JP 2011503006A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- fungicides
- formula
- alkoxy
- 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.)
- Abandoned
Links
- -1 heterocyclic amine Chemical class 0.000 title claims description 232
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 331
- 239000000203 mixture Substances 0.000 claims abstract description 233
- 201000010099 disease Diseases 0.000 claims abstract description 56
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 16
- 230000000855 fungicidal effect Effects 0.000 claims description 121
- 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 84
- 125000001424 substituent group Chemical group 0.000 claims description 63
- 239000007787 solid Substances 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 239000003899 bactericide agent Substances 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 29
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 20
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 12
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 12
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 11
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 10
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 10
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 8
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 7
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 7
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 7
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 7
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 7
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 claims description 6
- 125000006781 (C4-C10) cycloalkylcarbonyl group Chemical group 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 5
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 241000235349 Ascomycota Species 0.000 claims description 3
- 241000221198 Basidiomycota Species 0.000 claims description 3
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 3
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- XNNGIBBOOHUDLN-UHFFFAOYSA-N 4-[2-(3-chloroanilino)pyridin-4-yl]-n-(1-methoxypropan-2-yl)pyrimidin-2-amine Chemical compound COCC(C)NC1=NC=CC(C=2C=C(NC=3C=C(Cl)C=CC=3)N=CC=2)=N1 XNNGIBBOOHUDLN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- RFFJJTULQODEAZ-JTQLQIEISA-N n-(3,5-difluorophenyl)-4-[2-[[(2s)-1-methoxypropan-2-yl]amino]pyrimidin-4-yl]-1,3,5-triazin-2-amine Chemical compound COC[C@H](C)NC1=NC=CC(C=2N=C(NC=3C=C(F)C=C(F)C=3)N=CN=2)=N1 RFFJJTULQODEAZ-JTQLQIEISA-N 0.000 claims description 2
- CGRFEOXSDORMQK-UHFFFAOYSA-N n-(3-fluorophenyl)-4-[2-(1-methoxypropan-2-ylamino)pyrimidin-4-yl]-1,3,5-triazin-2-amine Chemical compound COCC(C)NC1=NC=CC(C=2N=C(NC=3C=C(F)C=CC=3)N=CN=2)=N1 CGRFEOXSDORMQK-UHFFFAOYSA-N 0.000 claims description 2
- CGRFEOXSDORMQK-NSHDSACASA-N n-(3-fluorophenyl)-4-[2-[[(2s)-1-methoxypropan-2-yl]amino]pyrimidin-4-yl]-1,3,5-triazin-2-amine Chemical compound COC[C@H](C)NC1=NC=CC(C=2N=C(NC=3C=C(F)C=CC=3)N=CN=2)=N1 CGRFEOXSDORMQK-NSHDSACASA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 244000000003 plant pathogen Species 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 244000053095 fungal pathogen Species 0.000 abstract description 4
- 239000000417 fungicide Substances 0.000 description 340
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 68
- 230000009471 action Effects 0.000 description 63
- 238000002360 preparation method Methods 0.000 description 62
- 239000000725 suspension Substances 0.000 description 58
- 238000012360 testing method Methods 0.000 description 55
- 239000000243 solution Substances 0.000 description 52
- 239000000047 product Substances 0.000 description 45
- 241000196324 Embryophyta Species 0.000 description 42
- 230000012010 growth Effects 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 150000001412 amines Chemical class 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
- 229920006395 saturated elastomer Polymers 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 25
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000009472 formulation Methods 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 20
- 241000233866 Fungi Species 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000012298 atmosphere Substances 0.000 description 18
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 18
- 230000002538 fungal effect Effects 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 241000209140 Triticum Species 0.000 description 11
- 235000021307 Triticum Nutrition 0.000 description 11
- 150000003857 carboxamides Chemical class 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000000645 desinfectant Substances 0.000 description 11
- 230000008099 melanin synthesis Effects 0.000 description 11
- 230000008506 pathogenesis Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 238000011161 development Methods 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 230000001954 sterilising effect Effects 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 102100038239 Protein Churchill Human genes 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 229930182558 Sterol Natural products 0.000 description 7
- 230000003115 biocidal effect Effects 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 150000003904 phospholipids Chemical class 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000003206 sterilizing agent Substances 0.000 description 7
- 150000003432 sterols Chemical class 0.000 description 7
- 235000003702 sterols Nutrition 0.000 description 7
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 7
- YLZGKZDEFJIHIJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl) carbamate Chemical compound C1=CC=C2N(C)C(OC(N)=O)=NC2=C1 YLZGKZDEFJIHIJ-UHFFFAOYSA-N 0.000 description 6
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 6
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 102000029749 Microtubule Human genes 0.000 description 6
- 108091022875 Microtubule Proteins 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 229930182764 Polyoxin Natural products 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000005640 glucopyranosyl group Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 210000004688 microtubule Anatomy 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- XQJQCBDIXRIYRP-STQMWFEESA-N trans-(1S,2R)-sedaxane Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1[C@H]1[C@H](C2CC2)C1 XQJQCBDIXRIYRP-STQMWFEESA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 1
- PTONZGYJJBJAGZ-UHFFFAOYSA-N tributyl-(2-methylsulfanylpyrimidin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC(SC)=N1 PTONZGYJJBJAGZ-UHFFFAOYSA-N 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 108010013280 ubiquinol oxidase Proteins 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US212907P | 2007-11-06 | 2007-11-06 | |
| PCT/US2008/082398 WO2009061761A2 (en) | 2007-11-06 | 2008-11-05 | Fungicidal heterocyclic amines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011503006A true JP2011503006A (ja) | 2011-01-27 |
| JP2011503006A5 JP2011503006A5 (enExample) | 2011-12-22 |
Family
ID=40521581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010532330A Abandoned JP2011503006A (ja) | 2007-11-06 | 2008-11-05 | 殺菌性複素環アミン |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8026359B2 (enExample) |
| EP (1) | EP2205086B1 (enExample) |
| JP (1) | JP2011503006A (enExample) |
| KR (1) | KR20100088150A (enExample) |
| CN (1) | CN101902912A (enExample) |
| AU (1) | AU2008324833A1 (enExample) |
| BR (1) | BRPI0817135A2 (enExample) |
| MX (1) | MX2010005033A (enExample) |
| WO (1) | WO2009061761A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015093551A1 (ja) * | 2013-12-18 | 2015-06-25 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、インク組成物、有機エレクトロルミネッセンス素子、電子機器、及び化合物の製造方法 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012101065A2 (en) * | 2011-01-28 | 2012-08-02 | Novartis Ag | Pyrimidine biaryl amine compounds and their uses |
| CA2828478C (en) | 2011-02-28 | 2019-12-31 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| WO2013020062A1 (en) | 2011-08-04 | 2013-02-07 | Array Biopharma Inc. | Quinazoline compounds as serine/threonine kinase inhibitors |
| AU2013225737B2 (en) | 2012-03-01 | 2018-03-01 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| RS61664B1 (sr) | 2012-04-24 | 2021-04-29 | Vertex Pharma | Inhibitori dna-pk |
| BR112015004548A2 (pt) | 2012-08-27 | 2017-08-08 | Array Biopharma Inc | inibidores de serina/treonina para tratamento de doenças hiperproliferativas |
| SI3527563T1 (sl) | 2013-03-12 | 2022-01-31 | Vertex Pharmaceuticals Incorporated | Inhibitorji DNA-PK |
| SI3424920T1 (sl) | 2013-10-17 | 2020-08-31 | Vertex Pharmaceuticals Incorporated | Kokristali (s)-n-metil-8-(1-((2'-metil-(4,5'-bipirimidin)-6-il)amino)propan-2-il) kinolin-4-karboksamida in devterirani derivati le-teh kot inhibitorji dna-pk |
| PL3129025T3 (pl) * | 2014-04-09 | 2019-11-29 | Genentech Inc | Sposób wytwarzania środków leczniczych |
| KR20190062485A (ko) | 2016-09-27 | 2019-06-05 | 버텍스 파마슈티칼스 인코포레이티드 | Dna-손상제 및 dna-pk 저해제의 조합을 사용한 암 치료 방법 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
| CN119841771A (zh) * | 2025-01-08 | 2025-04-18 | 华中农业大学 | 一种猪链球菌丝氨酸蛋白激酶抑制剂的筛选方法及其应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2386218A1 (en) * | 1999-10-07 | 2001-04-12 | Amgen Inc. | Triazine kinase inhibitors |
| GB0014022D0 (en) * | 2000-06-08 | 2000-08-02 | Novartis Ag | Organic compounds |
| ATE497603T1 (de) * | 2001-03-02 | 2011-02-15 | Gpc Biotech Ag | Drei-hybrid-assaysystem |
| EA007298B1 (ru) * | 2001-11-01 | 2006-08-25 | Янссен Фармацевтика Н.В. | Гетероариламины в качестве ингибиторов гликогенсинтаза-киназы 3-бета (ингибиторов gsk3) |
| GB0307268D0 (en) * | 2003-03-28 | 2003-05-07 | Syngenta Ltd | Organic compounds |
| US20050014753A1 (en) * | 2003-04-04 | 2005-01-20 | Irm Llc | Novel compounds and compositions as protein kinase inhibitors |
| CN1798734A (zh) * | 2003-04-04 | 2006-07-05 | Irm责任有限公司 | 作为蛋白激酶抑制剂的新化合物和组合物 |
| US20050130968A1 (en) * | 2003-10-03 | 2005-06-16 | Irvine Nicholas M. | Fungicidal 4-(2-aminopyridin-4-yl)-N-phenyl-1,3,5-triazin-2-amine derivatives |
| HN2005000795A (es) * | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| CA2685588A1 (en) * | 2007-06-08 | 2008-12-11 | Bayer Cropscience Sa | Fungicide heterocyclyl-pyrimidinyl-amino derivatives |
-
2008
- 2008-11-05 KR KR1020107012295A patent/KR20100088150A/ko not_active Withdrawn
- 2008-11-05 CN CN2008801217475A patent/CN101902912A/zh active Pending
- 2008-11-05 MX MX2010005033A patent/MX2010005033A/es unknown
- 2008-11-05 EP EP08847187.5A patent/EP2205086B1/en not_active Not-in-force
- 2008-11-05 WO PCT/US2008/082398 patent/WO2009061761A2/en not_active Ceased
- 2008-11-05 AU AU2008324833A patent/AU2008324833A1/en not_active Abandoned
- 2008-11-05 JP JP2010532330A patent/JP2011503006A/ja not_active Abandoned
- 2008-11-05 BR BRPI0817135-1A2A patent/BRPI0817135A2/pt not_active Application Discontinuation
-
2009
- 2009-05-14 US US12/741,047 patent/US8026359B2/en not_active Expired - Fee Related
-
2011
- 2011-08-16 US US13/210,427 patent/US20110301123A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015093551A1 (ja) * | 2013-12-18 | 2015-06-25 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、インク組成物、有機エレクトロルミネッセンス素子、電子機器、及び化合物の製造方法 |
| US10032991B2 (en) | 2013-12-18 | 2018-07-24 | Idemitsu Kosan Co., Ltd. | Compound, organic electroluminescence element material, ink composition, organic electroluminescence element, electronic device, and method for producing compound |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2205086A2 (en) | 2010-07-14 |
| US20100267729A1 (en) | 2010-10-21 |
| US8026359B2 (en) | 2011-09-27 |
| WO2009061761A3 (en) | 2009-06-25 |
| AU2008324833A1 (en) | 2009-05-14 |
| CN101902912A (zh) | 2010-12-01 |
| MX2010005033A (es) | 2010-05-27 |
| WO2009061761A2 (en) | 2009-05-14 |
| EP2205086B1 (en) | 2013-08-14 |
| KR20100088150A (ko) | 2010-08-06 |
| US20110301123A1 (en) | 2011-12-08 |
| BRPI0817135A2 (pt) | 2014-10-07 |
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