NZ553777A - Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives - Google Patents
Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivativesInfo
- Publication number
- NZ553777A NZ553777A NZ553777A NZ55377705A NZ553777A NZ 553777 A NZ553777 A NZ 553777A NZ 553777 A NZ553777 A NZ 553777A NZ 55377705 A NZ55377705 A NZ 55377705A NZ 553777 A NZ553777 A NZ 553777A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cf3s02hn
- cf3so2hn
- hydrogen
- solvate
- salt
- Prior art date
Links
- -1 trifluoromethanesulfonanilide oxime ether derivatives Chemical class 0.000 title claims abstract description 341
- 241001465754 Metazoa Species 0.000 title claims abstract description 87
- 244000045947 parasite Species 0.000 title claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 100
- 239000012453 solvate Substances 0.000 claims abstract description 80
- 241000238421 Arthropoda Species 0.000 claims abstract description 56
- 244000000013 helminth Species 0.000 claims abstract description 55
- 108010034145 Helminth Proteins Proteins 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 20
- OXDSKEQSEGDAFN-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenylmethanesulfonamide Chemical class FC(F)(F)S(=O)(=O)NC1=CC=CC=C1 OXDSKEQSEGDAFN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 338
- 125000000217 alkyl group Chemical group 0.000 claims description 177
- 229910052739 hydrogen Inorganic materials 0.000 claims description 154
- 239000001257 hydrogen Substances 0.000 claims description 154
- 238000000034 method Methods 0.000 claims description 125
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 82
- 150000002431 hydrogen Chemical class 0.000 claims description 75
- 125000001188 haloalkyl group Chemical group 0.000 claims description 74
- 239000000460 chlorine Chemical group 0.000 claims description 66
- 125000001072 heteroaryl group Chemical group 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 206010061217 Infestation Diseases 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
- 241000282414 Homo sapiens Species 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000001589 carboacyl group Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000003435 aroyl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- 230000002147 killing effect Effects 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 22
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 20
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 19
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 19
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 19
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 19
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 19
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 18
- 125000005110 aryl thio group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 17
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 17
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 17
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 17
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 16
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 16
- 239000011737 fluorine Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 16
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 16
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 15
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 15
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 15
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 15
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 15
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 14
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 13
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 13
- 125000005108 alkenylthio group Chemical group 0.000 claims description 13
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 12
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 12
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 12
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 11
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 4
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 4
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 3
- 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 3
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 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 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 129
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical class Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 101
- 239000000243 solution Substances 0.000 description 95
- 239000011541 reaction mixture Substances 0.000 description 93
- 238000006243 chemical reaction Methods 0.000 description 86
- 229910001868 water Inorganic materials 0.000 description 84
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 76
- 239000007787 solid Substances 0.000 description 75
- 241000258924 Ctenocephalides felis Species 0.000 description 72
- 238000002360 preparation method Methods 0.000 description 72
- 239000002904 solvent Substances 0.000 description 61
- 239000000377 silicon dioxide Substances 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 230000002829 reductive effect Effects 0.000 description 52
- 125000005843 halogen group Chemical group 0.000 description 45
- 241000607479 Yersinia pestis Species 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 241000238876 Acari Species 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- 238000012360 testing method Methods 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 231100000111 LD50 Toxicity 0.000 description 28
- 240000000528 Ricinus communis Species 0.000 description 28
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 26
- 238000004809 thin layer chromatography Methods 0.000 description 26
- 238000003756 stirring Methods 0.000 description 25
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- 239000012267 brine Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- 239000000725 suspension Substances 0.000 description 21
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- 239000002585 base Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
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- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 241000254173 Coleoptera Species 0.000 description 11
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- 230000000694 effects Effects 0.000 description 11
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
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- 239000004480 active ingredient Substances 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 241000244206 Nematoda Species 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 9
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- 229910052717 sulfur Inorganic materials 0.000 description 9
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 8
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 7
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- 239000002253 acid Substances 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- 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
- A01N47/02—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 no bond to a nitrogen atom
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- A—HUMAN NECESSITIES
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- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/04—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 no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
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- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
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- A61P33/14—Ectoparasiticides, e.g. scabicides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catching Or Destruction (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cultivation Of Plants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61253904P | 2004-09-23 | 2004-09-23 | |
| PCT/US2005/033791 WO2006034333A2 (en) | 2004-09-23 | 2005-09-21 | Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ553777A true NZ553777A (en) | 2010-11-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ553777A NZ553777A (en) | 2004-09-23 | 2005-09-21 | Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives |
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| EP (1) | EP1799636B1 (enExample) |
| JP (2) | JP4644254B2 (enExample) |
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| AU (2) | AU2005286723A1 (enExample) |
| BR (1) | BRPI0515917A (enExample) |
| CA (1) | CA2580843C (enExample) |
| DE (1) | DE602005009381D1 (enExample) |
| EC (1) | ECSP077336A (enExample) |
| ES (1) | ES2314724T3 (enExample) |
| IL (1) | IL181999A0 (enExample) |
| MX (1) | MX2007003378A (enExample) |
| NZ (1) | NZ553777A (enExample) |
| PE (1) | PE20060693A1 (enExample) |
| TW (1) | TW200624414A (enExample) |
| WO (1) | WO2006034333A2 (enExample) |
| ZA (1) | ZA200702389B (enExample) |
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| MX2007006072A (es) | 2004-11-19 | 2007-07-11 | Schering Plough Ltd | Control de parasitos en animales mediante el uso de derivados del parasiticida 2-fenil-3-(1h-pirrol-2-il)acrilonitrilo. |
| EP1890547A2 (en) * | 2005-06-09 | 2008-02-27 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| US20070238700A1 (en) * | 2006-04-10 | 2007-10-11 | Winzenberg Kevin N | N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their usage in controlling parasites |
| MX2009006467A (es) * | 2006-12-13 | 2009-08-21 | Schering Plough Ltd | Profarmacos solubles en agua de cloranfenicol, tiamfenicol y analogos de los mismos. |
| EP2091909A1 (en) * | 2006-12-13 | 2009-08-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| MX368680B (es) | 2007-06-27 | 2019-10-11 | Du Pont | Administración subcutánea de un derivado de isoxazol-benzamida para usarse en un método para proteger un mamífero de una pulga. |
| TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
| US8809268B2 (en) * | 2008-10-29 | 2014-08-19 | The Regents Of The University Of California | Combination therapy to combat helminth resistance |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| BR112012002524A2 (pt) | 2009-08-05 | 2019-09-24 | Du Pont | "composto de fórmula, composição, composição para proteger um animal de uma praga parasítica de invertebrados, métodos para controlar uma praga invertebrada e semente tratada" |
| EP2461684A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
| EP2531506B1 (en) | 2010-02-05 | 2014-05-14 | Intervet International B.V. | Spiroindoline compounds for use as anthelminthics |
| DK2568980T3 (en) * | 2010-05-12 | 2015-11-30 | Merial Inc | INJECTABLE PARASITICIDE FORMULATIONS OF LEVAMISOL AND MACROCYCLIC LACTONS |
| BR112013006030B1 (pt) | 2010-09-29 | 2020-03-17 | Intervet International B.V. | Composto e sais ou n-óxidos farmaceuticamente aceitáveis, e, uso do composto |
| WO2012041872A1 (en) | 2010-09-29 | 2012-04-05 | Intervet International B.V. | N-heteroaryl compounds with cyclic bridging unit for the treatment of parasitic diseases |
| CN103201265A (zh) * | 2010-11-12 | 2013-07-10 | 先正达参股股份有限公司 | 新颖的杀微生物剂 |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| JP2014520151A (ja) | 2011-06-20 | 2014-08-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 蠕虫感染を処置するためのヘテロ環式化合物 |
| WO2013017678A1 (en) | 2011-08-04 | 2013-02-07 | Intervet International B.V. | Novel spiroindoline compounds |
| RU2014126367A (ru) | 2011-11-28 | 2016-01-27 | Е.И.Дюпон Де Немур Энд Компани | Производные n-(4-хинолинметил)сульфонамидов и их применение в качестве антигельминтных средств |
| AU2013241853B2 (en) | 2012-03-28 | 2017-11-09 | Intervet International B.V. | Heteroaryl compounds with A-cyclic bridging unit |
| EP2830615A1 (en) | 2012-03-28 | 2015-02-04 | Intervet International B.V. | Heteroaryl compounds with cyclic bridging unit for use in the treatment helminth infection |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| EP2957557A1 (en) * | 2014-06-17 | 2015-12-23 | Novartis Tiergesundheit AG | New compounds |
| CN104910051B (zh) * | 2015-04-23 | 2016-08-24 | 郑州大学 | 一种硝酮取代的磺酰芳香胺衍生物及其制备方法 |
| WO2017188078A1 (ja) * | 2016-04-28 | 2017-11-02 | 住友化学株式会社 | 複素環化合物 |
| AR111260A1 (es) | 2017-03-31 | 2019-06-19 | Intervet Int Bv | Formulación farmacéutica de la sal de crotonil amino piridina |
| WO2019194220A1 (ja) * | 2018-04-06 | 2019-10-10 | 日本曹達株式会社 | (ヘテロ)アリールスルホンアミド化合物および有害生物防除剤 |
| WO2020002593A1 (en) | 2018-06-29 | 2020-01-02 | Intervet International B.V. | Compound for use against helminthic infection |
| EP3670491A1 (en) * | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-trifluoromethyl-acetophenone |
| EP3670492A1 (en) * | 2018-12-18 | 2020-06-24 | BASF Agro B.V. | Process for the preparation of 4-nitro-2-(trifluoromethyl)-1-(1-nitroethyl)-benzene |
| CN114364655B (zh) | 2019-09-12 | 2025-01-07 | 巴斯夫农业公司 | 硝酸α-甲基-[4-(硝基)-2-(三氟甲基)]-苄酯的制备方法 |
| BR112022012126A2 (pt) | 2019-12-18 | 2022-08-30 | Intervet Int Bv | Compostos antelmínticos compreendendo uma estrutura quinolínica |
| CN114846014B (zh) | 2019-12-18 | 2025-06-13 | 英特维特国际股份有限公司 | 包含氮杂吲哚结构的驱虫化合物 |
| MX2023006744A (es) | 2020-12-11 | 2023-06-19 | Intervet Int Bv | Compuestos antihelminticos que comprenden una estructura de tienopiridina. |
| WO2025027117A1 (en) | 2023-08-02 | 2025-02-06 | Intervet International B.V. | Carboxamide-4-quinoline compounds with anthelmintic activity |
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-
2005
- 2005-09-21 NZ NZ553777A patent/NZ553777A/en not_active IP Right Cessation
- 2005-09-21 CA CA2580843A patent/CA2580843C/en not_active Expired - Fee Related
- 2005-09-21 CN CNA2005800397960A patent/CN101065352A/zh active Pending
- 2005-09-21 WO PCT/US2005/033791 patent/WO2006034333A2/en not_active Ceased
- 2005-09-21 MX MX2007003378A patent/MX2007003378A/es active IP Right Grant
- 2005-09-21 AU AU2005286723A patent/AU2005286723A1/en not_active Abandoned
- 2005-09-21 DE DE602005009381T patent/DE602005009381D1/de not_active Expired - Lifetime
- 2005-09-21 US US11/231,423 patent/US7312248B2/en not_active Expired - Fee Related
- 2005-09-21 BR BRPI0515917-2A patent/BRPI0515917A/pt not_active IP Right Cessation
- 2005-09-21 PE PE2005001090A patent/PE20060693A1/es not_active Application Discontinuation
- 2005-09-21 JP JP2007533602A patent/JP4644254B2/ja not_active Expired - Fee Related
- 2005-09-21 KR KR1020077006702A patent/KR20070054691A/ko not_active Ceased
- 2005-09-21 EP EP05799819A patent/EP1799636B1/en not_active Expired - Lifetime
- 2005-09-21 ES ES05799819T patent/ES2314724T3/es not_active Expired - Lifetime
- 2005-09-21 AR ARP050103962A patent/AR054981A1/es unknown
- 2005-09-21 AT AT05799819T patent/ATE406348T1/de not_active IP Right Cessation
- 2005-09-22 TW TW094132870A patent/TW200624414A/zh unknown
-
2007
- 2007-03-18 IL IL181999A patent/IL181999A0/en unknown
- 2007-03-22 ZA ZA200702389A patent/ZA200702389B/xx unknown
- 2007-03-22 EC EC2007007336A patent/ECSP077336A/es unknown
- 2007-10-31 US US11/930,907 patent/US7906538B2/en not_active Expired - Fee Related
-
2010
- 2010-04-12 JP JP2010091788A patent/JP2010209083A/ja not_active Withdrawn
- 2010-04-12 AU AU2010201450A patent/AU2010201450A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101065352A (zh) | 2007-10-31 |
| US20060063841A1 (en) | 2006-03-23 |
| US7906538B2 (en) | 2011-03-15 |
| WO2006034333A3 (en) | 2006-07-27 |
| JP4644254B2 (ja) | 2011-03-02 |
| MX2007003378A (es) | 2007-05-10 |
| CA2580843C (en) | 2011-03-29 |
| PE20060693A1 (es) | 2006-09-01 |
| EP1799636B1 (en) | 2008-08-27 |
| US20080262048A1 (en) | 2008-10-23 |
| ZA200702389B (en) | 2008-10-29 |
| JP2010209083A (ja) | 2010-09-24 |
| CA2580843A1 (en) | 2006-03-30 |
| KR20070054691A (ko) | 2007-05-29 |
| BRPI0515917A (pt) | 2008-08-12 |
| TW200624414A (en) | 2006-07-16 |
| JP2008514610A (ja) | 2008-05-08 |
| US7312248B2 (en) | 2007-12-25 |
| ATE406348T1 (de) | 2008-09-15 |
| WO2006034333A2 (en) | 2006-03-30 |
| IL181999A0 (en) | 2007-07-04 |
| ES2314724T3 (es) | 2009-03-16 |
| AR054981A1 (es) | 2007-08-01 |
| AU2010201450A1 (en) | 2010-05-13 |
| EP1799636A2 (en) | 2007-06-27 |
| ECSP077336A (es) | 2007-04-26 |
| DE602005009381D1 (de) | 2008-10-09 |
| AU2005286723A1 (en) | 2006-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |