JP6407987B2 - ナフチル又はイソキノリニル置換イソチアゾリン化合物 - Google Patents
ナフチル又はイソキノリニル置換イソチアゾリン化合物 Download PDFInfo
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- JP6407987B2 JP6407987B2 JP2016522420A JP2016522420A JP6407987B2 JP 6407987 B2 JP6407987 B2 JP 6407987B2 JP 2016522420 A JP2016522420 A JP 2016522420A JP 2016522420 A JP2016522420 A JP 2016522420A JP 6407987 B2 JP6407987 B2 JP 6407987B2
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- alkyl
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- cycloalkyl
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- alkoxy
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- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 title claims description 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 title description 2
- 125000001624 naphthyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 816
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims description 680
- 229910052739 hydrogen Inorganic materials 0.000 claims description 293
- 239000001257 hydrogen Substances 0.000 claims description 292
- 125000001424 substituent group Chemical group 0.000 claims description 146
- 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 127
- 125000005842 heteroatom Chemical group 0.000 claims description 119
- 125000000623 heterocyclic group Chemical group 0.000 claims description 112
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 101
- 229910052736 halogen Inorganic materials 0.000 claims description 92
- 150000002367 halogens Chemical class 0.000 claims description 92
- 229910052717 sulfur Inorganic materials 0.000 claims description 92
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 91
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 79
- 229910052760 oxygen Inorganic materials 0.000 claims description 71
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 70
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 70
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 63
- 229920006395 saturated elastomer Polymers 0.000 claims description 63
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 49
- 125000001931 aliphatic group Chemical group 0.000 claims description 49
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 42
- 241000607479 Yersinia pestis Species 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 26
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 24
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 20
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 241001465754 Metazoa Species 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 13
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 239000002689 soil Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000009395 breeding Methods 0.000 claims description 7
- 150000002466 imines Chemical class 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 230000001488 breeding effect Effects 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- 230000009545 invasion Effects 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 35
- 230000016571 aggressive behavior Effects 0.000 claims 2
- 238000003976 plant breeding Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 237
- 241000894007 species Species 0.000 description 144
- 241000196324 Embryophyta Species 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000002904 solvent Substances 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 150000003254 radicals Chemical class 0.000 description 36
- 241000244206 Nematoda Species 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 28
- 150000001412 amines Chemical class 0.000 description 25
- 239000002585 base Substances 0.000 description 21
- 108090000623 proteins and genes Proteins 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- 229910052801 chlorine Inorganic materials 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 102000004169 proteins and genes Human genes 0.000 description 18
- 239000003053 toxin Substances 0.000 description 18
- 231100000765 toxin Toxicity 0.000 description 18
- 108700012359 toxins Proteins 0.000 description 18
- 241000238631 Hexapoda Species 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 241000258937 Hemiptera Species 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 150000003573 thiols Chemical class 0.000 description 11
- 241000254173 Coleoptera Species 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000004009 herbicide Substances 0.000 description 10
- 230000000749 insecticidal effect Effects 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
- 125000004434 sulfur atom Chemical group 0.000 description 10
- 241000255777 Lepidoptera Species 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 241001414989 Thysanoptera Species 0.000 description 9
- 229940126214 compound 3 Drugs 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000257303 Hymenoptera Species 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 241000482268 Zea mays subsp. mays Species 0.000 description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 241001124076 Aphididae Species 0.000 description 7
- 241000239223 Arachnida Species 0.000 description 7
- 125000006414 CCl Chemical group ClC* 0.000 description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 241000219146 Gossypium Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 235000002595 Solanum tuberosum Nutrition 0.000 description 7
- 244000061456 Solanum tuberosum Species 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000005580 one pot reaction Methods 0.000 description 6
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 5
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 4
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 108091000699 pea lectin Proteins 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004477 pesticide formulation type Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
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- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 108020001580 protein domains Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004290 pyrazolidin-3-yl group Chemical group [H]N1N([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- YUWAUUTYKFAJBH-UHFFFAOYSA-N pyridin-4-ylmethanethiol Chemical compound SCC1=CC=NC=C1 YUWAUUTYKFAJBH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- XXVLCYRUWQRBLP-UHFFFAOYSA-N quinolin-2-ylmethanethiol Chemical compound C1=CC=CC2=NC(CS)=CC=C21 XXVLCYRUWQRBLP-UHFFFAOYSA-N 0.000 description 1
- 235000020079 raki Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002795 scorpion venom Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002708 spider venom Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 108010076424 stilbene synthase Proteins 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 1
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 125000004569 thiomorpholin-2-yl group Chemical group N1CC(SCC1)* 0.000 description 1
- 125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 229940035289 tobi Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 229940116861 trichinella britovi Drugs 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- AECHPKVYOLOZLF-UHFFFAOYSA-N trifluoro(phenyl)-$l^{4}-sulfane Chemical compound FS(F)(F)C1=CC=CC=C1 AECHPKVYOLOZLF-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
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- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838354P | 2013-06-24 | 2013-06-24 | |
| US61/838,354 | 2013-06-24 | ||
| PCT/EP2014/063101 WO2014206907A1 (en) | 2013-06-24 | 2014-06-23 | Naphthyl- or isoquinolinyl-substituted isothiazoline compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016530226A JP2016530226A (ja) | 2016-09-29 |
| JP2016530226A5 JP2016530226A5 (enExample) | 2017-07-06 |
| JP6407987B2 true JP6407987B2 (ja) | 2018-10-17 |
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Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10327446B2 (enExample) |
| EP (1) | EP3013807B1 (enExample) |
| JP (1) | JP6407987B2 (enExample) |
| CN (1) | CN105473564A (enExample) |
| BR (1) | BR112015032344A2 (enExample) |
| CA (1) | CA2916824C (enExample) |
| ES (1) | ES2817098T3 (enExample) |
| MX (1) | MX374351B (enExample) |
| WO (1) | WO2014206907A1 (enExample) |
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| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | Substituted cyclopropyl derivatives |
| CN111333512A (zh) * | 2020-03-09 | 2020-06-26 | 江苏君若药业有限公司 | 阿福拉纳关键中间体4-乙酰基-1-萘甲酸酯的制备 |
| CN114380762A (zh) * | 2022-01-23 | 2022-04-22 | 贵州大学 | 异恶唑啉酰肼衍生物及其制备方法和用途 |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| CN118765716B (zh) * | 2024-09-09 | 2024-12-06 | 云南省农业科学院药用植物研究所 | 一种中华腐生牛肝菌菌种培养方法 |
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| TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| AU2008235089B8 (en) * | 2007-04-10 | 2014-04-10 | Bayer Intellectual Property Gmbh | Insecticidal aryl isoxazoline derivatives |
| CN101815706A (zh) * | 2007-06-13 | 2010-08-25 | 杜邦公司 | 异*唑啉杀昆虫剂 |
| JP5316808B2 (ja) * | 2007-06-29 | 2013-10-16 | 日産化学工業株式会社 | 置換イソキサゾリン又はエノンオキシム化合物および有害生物防除剤 |
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| EP2382196B1 (en) * | 2008-12-23 | 2015-08-12 | Basf Se | Imine compounds for combating invertebrate pests |
| CN102762543B (zh) * | 2010-02-01 | 2016-03-09 | 巴斯夫欧洲公司 | 用于防除动物害虫的取代的酮型异*唑啉化合物和衍生物 |
| EP2536698B1 (en) * | 2010-02-17 | 2015-06-10 | Syngenta Participations AG | Isoxazoline derivatives as insecticides |
| WO2013026933A1 (en) * | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
| BR122018069466B1 (pt) * | 2011-09-13 | 2019-04-02 | Syngenta Participations Ag | Derivados isotiazolina como compostos inseticidas |
| US20140343085A1 (en) * | 2011-11-29 | 2014-11-20 | Novartis Ag | Use of aryl derivatives for controlling ectoparasites |
| KR20140115329A (ko) | 2011-12-23 | 2014-09-30 | 바스프 에스이 | 무척추동물 해충 퇴치를 위한 이소티아졸린 화합물 |
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2014
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- 2014-06-23 CA CA2916824A patent/CA2916824C/en not_active Expired - Fee Related
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| CA2916824A1 (en) | 2014-12-31 |
| MX374351B (es) | 2025-03-06 |
| CN105473564A (zh) | 2016-04-06 |
| US10327446B2 (en) | 2019-06-25 |
| JP2016530226A (ja) | 2016-09-29 |
| WO2014206907A1 (en) | 2014-12-31 |
| BR112015032344A2 (pt) | 2017-07-25 |
| US20160374342A1 (en) | 2016-12-29 |
| EP3013807A1 (en) | 2016-05-04 |
| MX2015018019A (es) | 2016-07-06 |
| ES2817098T3 (es) | 2021-04-06 |
| EP3013807B1 (en) | 2020-04-08 |
| CA2916824C (en) | 2021-05-25 |
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