ES2542409T3 - Derivados de isoxazol - Google Patents
Derivados de isoxazol Download PDFInfo
- Publication number
- ES2542409T3 ES2542409T3 ES12707629.7T ES12707629T ES2542409T3 ES 2542409 T3 ES2542409 T3 ES 2542409T3 ES 12707629 T ES12707629 T ES 12707629T ES 2542409 T3 ES2542409 T3 ES 2542409T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- haloalkyl
- substituted
- cyano
- halogen
- 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.)
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- 150000002545 isoxazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- -1 C1-alkylsulfinyl -C6 Chemical group 0.000 claims abstract description 114
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 105
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 74
- 150000002367 halogens Chemical class 0.000 claims abstract description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 56
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 51
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 18
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 15
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims abstract description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims abstract description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims abstract description 3
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims abstract description 3
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000006774 (C2-C7) haloalkylcarbonyl group Chemical group 0.000 claims abstract description 3
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims abstract description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 65
- 241001465754 Metazoa Species 0.000 claims description 44
- 150000003254 radicals Chemical class 0.000 claims description 29
- 239000004480 active ingredient Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 244000045947 parasite Species 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 241000251468 Actinopterygii Species 0.000 claims description 7
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 6
- 125000005458 thianyl group Chemical group 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- WUXYMHDSFCIQMA-UHFFFAOYSA-N n-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methyl]propanamide Chemical compound S1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 WUXYMHDSFCIQMA-UHFFFAOYSA-N 0.000 claims description 4
- ZQZFJPCIFQYLBC-UHFFFAOYSA-N [2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methanamine Chemical compound NCC1=C(C)OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 ZQZFJPCIFQYLBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000532 dioxanyl group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- BOTREHHXSQGWTR-UHFFFAOYSA-N oxolane-3-carboxylic acid Chemical compound OC(=O)C1CCOC1 BOTREHHXSQGWTR-UHFFFAOYSA-N 0.000 claims description 3
- YJEMQUPUTXKLMX-UHFFFAOYSA-N N-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]thiophen-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 YJEMQUPUTXKLMX-UHFFFAOYSA-N 0.000 claims description 2
- HRVNBQRGLQRTMT-UHFFFAOYSA-N N-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]thiophen-3-yl]methyl]propanamide Chemical compound S1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C1 HRVNBQRGLQRTMT-UHFFFAOYSA-N 0.000 claims description 2
- RHRVWNITRNKWCH-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 RHRVWNITRNKWCH-UHFFFAOYSA-N 0.000 claims description 2
- PSBMFJPWLMRSHY-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]propanamide Chemical compound O1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 PSBMFJPWLMRSHY-UHFFFAOYSA-N 0.000 claims description 2
- KFMNGJUVJJROFF-UHFFFAOYSA-N [5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methanamine Chemical compound NCC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 KFMNGJUVJJROFF-UHFFFAOYSA-N 0.000 claims description 2
- WFBFJMNWFUCZMJ-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 WFBFJMNWFUCZMJ-UHFFFAOYSA-N 0.000 claims description 2
- SLUWJSVOOWRWBS-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]propanamide Chemical compound O1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C1 SLUWJSVOOWRWBS-UHFFFAOYSA-N 0.000 claims description 2
- LTOSPMAKMXIYDK-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]oxolane-3-carboxamide Chemical compound CC=1OC(=CC1CNC(=O)C1COCC1)C1=NOC(C1)(C(F)(F)F)C1=CC(=CC(=C1)Cl)Cl LTOSPMAKMXIYDK-UHFFFAOYSA-N 0.000 claims 1
- IZXSNIIJCNUTPF-UHFFFAOYSA-N NCC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 Chemical compound NCC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 IZXSNIIJCNUTPF-UHFFFAOYSA-N 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000460 chlorine Substances 0.000 description 49
- 239000000243 solution Substances 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 238000000034 method Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000013543 active substance Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000012043 crude product Substances 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 241000607479 Yersinia pestis Species 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 241000238876 Acari Species 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 241000255925 Diptera Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 244000078703 ectoparasite Species 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000258924 Ctenocephalides felis Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 241000258242 Siphonaptera Species 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 238000011894 semi-preparative HPLC Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241000699684 Meriones unguiculatus Species 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000019688 fish Nutrition 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000283086 Equidae Species 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 241000699694 Gerbillinae Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000282887 Suidae Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- UVRRIABXNIGUJZ-UHFFFAOYSA-N methyl 2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=COC=1C UVRRIABXNIGUJZ-UHFFFAOYSA-N 0.000 description 1
- ZXGBIKDFARSQKO-UHFFFAOYSA-N methyl 5-acetyl-2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=C(C(C)=O)OC=1C ZXGBIKDFARSQKO-UHFFFAOYSA-N 0.000 description 1
- WINMHOHYPKKTEM-UHFFFAOYSA-N methyl 5-formyl-2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=C(C=O)OC=1C WINMHOHYPKKTEM-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000000590 parasiticidal effect Effects 0.000 description 1
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- 125000002255 pentenyl group Chemical class C(=CCCC)* 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000010665 pine oil Substances 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
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
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- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
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- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000001590 sorbitan monolaureate Substances 0.000 description 1
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- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
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- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- A01N43/72—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<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic 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 |
|---|---|---|---|
| CH407112011 | 2011-03-10 | ||
| CH4072011 | 2011-03-10 | ||
| PCT/EP2012/054161 WO2012120135A1 (en) | 2011-03-10 | 2012-03-09 | Isoxazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2542409T3 true ES2542409T3 (es) | 2015-08-05 |
Family
ID=45809012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12707629.7T Active ES2542409T3 (es) | 2011-03-10 | 2012-03-09 | Derivados de isoxazol |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8822466B2 (enExample) |
| EP (1) | EP2683713B1 (enExample) |
| JP (1) | JP2014507459A (enExample) |
| CN (1) | CN103502246A (enExample) |
| AR (1) | AR085657A1 (enExample) |
| AU (1) | AU2012224521B2 (enExample) |
| BR (1) | BR112013022755A2 (enExample) |
| CA (1) | CA2829149A1 (enExample) |
| CL (1) | CL2013002472A1 (enExample) |
| CO (1) | CO6801794A2 (enExample) |
| ES (1) | ES2542409T3 (enExample) |
| MX (1) | MX2013010297A (enExample) |
| RU (1) | RU2013145304A (enExample) |
| WO (1) | WO2012120135A1 (enExample) |
| ZA (1) | ZA201306175B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33403A (es) * | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
| RU2763496C2 (ru) | 2012-02-06 | 2021-12-29 | БЁРИНГЕР ИНГЕЛЬХАЙМ ЭНИМАЛ ХЕЛТ ЮЭсЭй ИНК. | Паразитицидные пероральные ветеринарные композиции, включающие системно действующие активные агенты, способы и применение этих композиций и способов |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
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| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| CN101331127B (zh) * | 2005-12-16 | 2012-05-23 | 杜邦公司 | 用于防治无脊椎害虫的5-芳基异噁唑啉 |
| TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| BRPI0707091B8 (pt) * | 2006-03-10 | 2018-02-14 | Nissan Chemical Ind Ltd | composto de isoxalina e benzaldoxima substituído ou um sal do mesmo; pesticida, agroquímico, endo- ou ecto-parasiticidapara mamíferos ou pássaros, inseticida e acaricida contendo como um ou mais ingredientes ativos selecionados a partir do composto de isoxalina substituído e o sal do mesmo |
| WO2008122375A2 (en) * | 2007-04-10 | 2008-10-16 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| TWI600639B (zh) | 2007-08-17 | 2017-10-01 | 杜邦股份有限公司 | 製備５-鹵烷基-４，５-二氫異唑衍生物之化合物 |
| WO2009071500A2 (en) | 2007-12-03 | 2009-06-11 | Novartis Ag | Organic compounds |
| TWI454472B (zh) * | 2008-12-19 | 2014-10-01 | Novartis Ag | 有機化合物 |
| JP2010235590A (ja) * | 2009-03-09 | 2010-10-21 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
| UY33403A (es) * | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
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- 2012-03-09 WO PCT/EP2012/054161 patent/WO2012120135A1/en not_active Ceased
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- 2012-03-09 MX MX2013010297A patent/MX2013010297A/es not_active Application Discontinuation
- 2012-03-09 CA CA2829149A patent/CA2829149A1/en not_active Abandoned
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- 2012-03-09 BR BR112013022755A patent/BR112013022755A2/pt not_active IP Right Cessation
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| EP2683713B1 (en) | 2015-04-22 |
| NZ614662A (en) | 2015-06-26 |
| CN103502246A (zh) | 2014-01-08 |
| US20130345221A1 (en) | 2013-12-26 |
| WO2012120135A1 (en) | 2012-09-13 |
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| AR085657A1 (es) | 2013-10-16 |
| ZA201306175B (en) | 2014-04-30 |
| EP2683713A1 (en) | 2014-01-15 |
| RU2013145304A (ru) | 2015-04-20 |
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