NO313518B1 - Parasitticidale forbindelser - Google Patents
Parasitticidale forbindelser Download PDFInfo
- Publication number
- NO313518B1 NO313518B1 NO19992732A NO992732A NO313518B1 NO 313518 B1 NO313518 B1 NO 313518B1 NO 19992732 A NO19992732 A NO 19992732A NO 992732 A NO992732 A NO 992732A NO 313518 B1 NO313518 B1 NO 313518B1
- Authority
- NO
- Norway
- Prior art keywords
- dichloro
- cyano
- compound
- pyrazole
- trifluoromethylphenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 313
- 230000000590 parasiticidal effect Effects 0.000 title claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 357
- 238000002360 preparation method Methods 0.000 claims description 164
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 143
- 239000000203 mixture Substances 0.000 claims description 101
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 77
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 40
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 36
- -1 2,4,6-trisubstituted phenyl Chemical group 0.000 claims description 33
- 238000010992 reflux Methods 0.000 claims description 33
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical group [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 21
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical group C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 19
- 229950005228 bromoform Drugs 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 15
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- PLHSKXBFZPAQOD-UHFFFAOYSA-N phenyl(tribromomethyl)mercury Chemical compound BrC(Br)(Br)[Hg]C1=CC=CC=C1 PLHSKXBFZPAQOD-UHFFFAOYSA-N 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052723 transition metal Inorganic materials 0.000 claims description 10
- 150000003624 transition metals Chemical class 0.000 claims description 10
- SOWFJRRENUZFJD-UHFFFAOYSA-N 4-(2,2-dibromocyclopropyl)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=C(C#N)C(C2C(C2)(Br)Br)=C1 SOWFJRRENUZFJD-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 238000001149 thermolysis Methods 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- DRBAAFANJKSJOI-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[1-(trifluoromethyl)cyclopropyl]pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=C(C#N)C(C2(CC2)C(F)(F)F)=C1 DRBAAFANJKSJOI-UHFFFAOYSA-N 0.000 claims description 5
- 241000282412 Homo Species 0.000 claims description 5
- 230000003071 parasitic effect Effects 0.000 claims description 5
- FMCJEPSLAMDJTN-UHFFFAOYSA-N 4-(2,2-dichlorocyclopropyl)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=C(C#N)C(C2C(C2)(Cl)Cl)=C1 FMCJEPSLAMDJTN-UHFFFAOYSA-N 0.000 claims description 4
- JPCAVYRPGUDXAK-UHFFFAOYSA-N 4-[1-chloro-2-(difluoromethyl)cyclopropyl]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound FC(F)C1CC1(Cl)C1=CN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)N=C1C#N JPCAVYRPGUDXAK-UHFFFAOYSA-N 0.000 claims description 4
- ZFHFCQOBLUMTCL-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[1-(trifluoromethyl)cyclopropyl]pyrazole-3-carbonitrile Chemical compound NC1=C(C2(CC2)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZFHFCQOBLUMTCL-UHFFFAOYSA-N 0.000 claims description 4
- VUGACNDBOVRKKT-UHFFFAOYSA-N 5-amino-4-(2,2-dibromocyclopropyl)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound N#CC1=NN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C(N)=C1C1CC1(Br)Br VUGACNDBOVRKKT-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 238000011200 topical administration Methods 0.000 claims description 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000002297 parasiticide Substances 0.000 claims description 2
- MVIAEGXPYBMVPT-UHFFFAOYSA-N phenyl(trichloromethyl)mercury Chemical compound ClC(Cl)(Cl)[Hg]C1=CC=CC=C1 MVIAEGXPYBMVPT-UHFFFAOYSA-N 0.000 claims description 2
- ITDJKCJYYAQMRO-UHFFFAOYSA-L rhodium(2+);diacetate Chemical group [Rh+2].CC([O-])=O.CC([O-])=O ITDJKCJYYAQMRO-UHFFFAOYSA-L 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 1
- 150000002730 mercury Chemical class 0.000 claims 1
- 150000003219 pyrazolines Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 317
- 239000000243 solution Substances 0.000 description 170
- 239000007787 solid Substances 0.000 description 110
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 105
- 239000003480 eluent Substances 0.000 description 97
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 96
- 239000000741 silica gel Substances 0.000 description 96
- 229910002027 silica gel Inorganic materials 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 95
- 239000011541 reaction mixture Substances 0.000 description 80
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 238000004440 column chromatography Methods 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
- 238000002425 crystallisation Methods 0.000 description 23
- 230000008025 crystallization Effects 0.000 description 23
- 239000011734 sodium Substances 0.000 description 23
- 239000012267 brine Substances 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 22
- 238000004007 reversed phase HPLC Methods 0.000 description 22
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 14
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- 241000254173 Coleoptera Species 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 241000238876 Acari Species 0.000 description 10
- 241000255925 Diptera Species 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 238000010828 elution Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241000238421 Arthropoda Species 0.000 description 8
- 241000607479 Yersinia pestis Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
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- 239000002243 precursor Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- VUPQHSHTKBZVML-UHFFFAOYSA-J rhodium(3+);tetraacetate Chemical compound [Rh+3].[Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O VUPQHSHTKBZVML-UHFFFAOYSA-J 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
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- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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- FYOWOHMZNWQLFG-UHFFFAOYSA-N [2,6-dichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C=C1Cl FYOWOHMZNWQLFG-UHFFFAOYSA-N 0.000 description 3
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9625290.3A GB9625290D0 (en) | 1996-12-05 | 1996-12-05 | Parasiticidal agents |
| GBGB9702235.4A GB9702235D0 (en) | 1997-02-04 | 1997-02-04 | Parasiticidal agents |
| GBGB9712045.5A GB9712045D0 (en) | 1997-06-10 | 1997-06-10 | Parasiticidal agents |
| PCT/EP1997/006697 WO1998024767A1 (fr) | 1996-12-05 | 1997-11-25 | Pyrazoles antiparasitaires |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992732D0 NO992732D0 (no) | 1999-06-04 |
| NO992732L NO992732L (no) | 1999-08-05 |
| NO313518B1 true NO313518B1 (no) | 2002-10-14 |
Family
ID=27268619
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO992736A NO992736D0 (no) | 1996-12-05 | 1999-06-04 | Ikke oppgitt |
| NO19992732A NO313518B1 (no) | 1996-12-05 | 1999-06-04 | Parasitticidale forbindelser |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO992736A NO992736D0 (no) | 1996-12-05 | 1999-06-04 | Ikke oppgitt |
Country Status (40)
| Country | Link |
|---|---|
| US (2) | US6075043A (fr) |
| EP (1) | EP0946515B1 (fr) |
| JP (2) | JP3950483B2 (fr) |
| KR (1) | KR100354311B1 (fr) |
| CN (1) | CN1106386C (fr) |
| AR (1) | AR013879A1 (fr) |
| AT (1) | ATE233736T1 (fr) |
| AU (1) | AU720705B2 (fr) |
| BG (1) | BG64127B1 (fr) |
| BR (1) | BR9713565A (fr) |
| CA (1) | CA2273951C (fr) |
| CO (1) | CO5031251A1 (fr) |
| CZ (1) | CZ295295B6 (fr) |
| DE (1) | DE69719547T2 (fr) |
| DK (1) | DK0946515T3 (fr) |
| DZ (1) | DZ2360A1 (fr) |
| EA (1) | EA002278B1 (fr) |
| ES (1) | ES2191870T3 (fr) |
| HK (1) | HK1029111A1 (fr) |
| HR (1) | HRP970663B1 (fr) |
| HU (1) | HUP0000544A3 (fr) |
| ID (1) | ID21556A (fr) |
| IL (1) | IL129866A (fr) |
| IS (1) | IS1982B (fr) |
| MA (1) | MA24414A1 (fr) |
| MY (1) | MY117021A (fr) |
| NO (2) | NO992736D0 (fr) |
| NZ (1) | NZ335611A (fr) |
| OA (1) | OA11055A (fr) |
| PA (1) | PA8442101A1 (fr) |
| PE (1) | PE20199A1 (fr) |
| PL (1) | PL190926B1 (fr) |
| PT (1) | PT946515E (fr) |
| RS (1) | RS49720B (fr) |
| SK (1) | SK285203B6 (fr) |
| TN (1) | TNSN97197A1 (fr) |
| TW (1) | TW524667B (fr) |
| UA (1) | UA60321C2 (fr) |
| UY (2) | UY24798A1 (fr) |
| WO (1) | WO1998024767A1 (fr) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW524667B (en) | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| GB9801851D0 (en) * | 1998-01-29 | 1998-03-25 | Pfizer Ltd | Parasiticidal agents |
| GB9810354D0 (en) * | 1998-05-14 | 1998-07-15 | Pfizer Ltd | Heterocycles |
| GB9811050D0 (en) * | 1998-05-22 | 1998-07-22 | Pfizer Ltd | Pyrazoles |
| US6531501B1 (en) | 1998-12-11 | 2003-03-11 | Aventis Cropscience, S.A. | Control of arthropods in animals |
| AR021608A1 (es) * | 1998-12-11 | 2002-07-31 | Merial Ltd | Represion de artropodos en animales |
| GB9916052D0 (en) * | 1999-07-08 | 1999-09-08 | Pfizer Ltd | Anthelmintic compositions |
| EP1237873B1 (fr) | 1999-12-02 | 2013-04-03 | Merial Limited | Controle des arthropodes chez les animaux |
| WO2003076409A1 (fr) * | 2002-03-14 | 2003-09-18 | Syngenta Participations Ag | Derives de 1-phenyl-3-phenylpyrazole utilises comme herbicides |
| CH697663B1 (de) * | 2003-01-07 | 2009-01-15 | Lanxess Deutschland Gmbh | Pyrazolylalkine. |
| WO2005023773A1 (fr) * | 2003-09-04 | 2005-03-17 | Pfizer Limited | Procede pour la preparation d'arylpyrazoles substitues |
| GB0329314D0 (en) * | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
| US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
| EP1735284A1 (fr) | 2004-03-18 | 2006-12-27 | Pfizer Limited | Sulfamides n-(1-arylpyrazol-4l) et leur utilisation en tant qu'anti-parasitaires |
| BRPI0611798A2 (pt) | 2005-06-15 | 2009-01-13 | Pfizer Ltd | compostos de arilpirazàis substituÍdos, sua composiÇço farmacÊutica e uso |
| US20070149464A1 (en) * | 2005-06-15 | 2007-06-28 | Pfizer Inc. | Combination |
| US20080146643A1 (en) * | 2005-06-15 | 2008-06-19 | Pfizer Limited | Combination |
| US7645786B2 (en) | 2005-06-15 | 2010-01-12 | Pfizer Inc. | Substituted arylpyrazoles |
| US20080176865A1 (en) * | 2005-06-15 | 2008-07-24 | Pfizer Limited | Substituted arylpyrazoles |
| JP2009500425A (ja) | 2005-07-06 | 2009-01-08 | セプラコア インコーポレーテッド | エスゾピクロン及びトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−ｎ−メチル−１−ナフタレンアミン又はトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−１−ナフタレンアミンの組み合わせ、並びに閉経期並びに気分、不安、及び認知障害の治療方法 |
| EP1783114A1 (fr) * | 2005-11-03 | 2007-05-09 | Novartis AG | Dérivés de N-(hétéro)aryle indole comme pesticides |
| DE102006061537A1 (de) | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
| DE102006061538A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren |
| MX2012011549A (es) | 2010-04-08 | 2013-01-29 | Ah Usa 42 Llc | Derivados de 3,5-difenil-isoxazolina sustituida como insecticidas y acaricidas. |
| CA2807005C (fr) | 2010-08-05 | 2015-04-07 | Ah Usa 42 Llc | Derives d'isoxazoline en tant qu'agents antiparasitaires |
| BR112013006686A2 (pt) | 2010-09-24 | 2017-11-14 | Zoetis Llc | isoxazolina oximas como agentes antiparasitários |
| AU2012226475C1 (en) | 2011-03-10 | 2015-08-06 | Zoetis Services Llc | Spirocyclic isoxazoline derivatives as antiparasitic agents |
| CA2829179C (fr) | 2011-03-22 | 2016-07-05 | Zoetis Llc | Derives d'isoxazoline en tant qu'agents anti-parasitaires |
| WO2013000572A1 (fr) | 2011-06-30 | 2013-01-03 | 2LUTION GmbH | Agents de lutte contre les parasites d'animaux |
| RU2014131951A (ru) | 2012-02-03 | 2016-03-27 | Зоэтис Ллс | Производные дигидрофуран азетидина в качестве противопаразитарных агентов |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| MX336431B (es) | 2012-05-09 | 2016-01-18 | Zoetis Services Llc | Derivados de azetidina como agentes antiparasitarios. |
| WO2014093481A1 (fr) | 2012-12-12 | 2014-06-19 | Zoetis Llc | Compositions injectables de phénylpyrazole |
| AR112480A1 (es) | 2017-08-24 | 2019-10-30 | Novo Nordisk As | Composiciones de glp-1 y sus usos |
| CN111116478B (zh) * | 2019-12-18 | 2021-10-26 | 浙江金伯士药业有限公司 | 一种兽用抗生素维吉霉素中间体的制备方法 |
| AU2021208601A1 (en) | 2020-02-18 | 2022-07-28 | Novo Nordisk A/S | Glp-1 compositions and uses thereof |
| CN115894374A (zh) * | 2023-02-16 | 2023-04-04 | 广州佳途科技股份有限公司 | 一种氟甲腈的制备方法及其应用 |
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| DE2658725A1 (de) * | 1976-12-24 | 1978-07-06 | Bayer Ag | Mittel zur bekaempfung von tierischen ektoparasiten mit stark ausgepraegter residualwirkung |
| US4479968A (en) * | 1980-10-17 | 1984-10-30 | The Wellcome Foundation Ltd. | Control of ectoparasitic infestations of pigs |
| GB2086302A (en) * | 1980-10-24 | 1982-05-12 | Bone Cravens Ltd | Prefill Valve System |
| GB8713769D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5232940A (en) * | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| GB8613914D0 (en) * | 1986-06-07 | 1986-07-09 | Coopers Animal Health | Liquid formulations |
| DE3771318D1 (de) * | 1986-12-05 | 1991-08-14 | Ciba Geigy Ag | Ektoparasitizide nicht-waessrige pour-on-fluessigformulierung. |
| DE3706993A1 (de) * | 1987-03-05 | 1988-09-15 | Bayer Ag | 5-amino-3-halogenalkyl-1-aryl-pyrazole |
| SE455750B (sv) | 1987-06-11 | 1988-08-01 | Ericsson Telefon Ab L M | Digitalt tidsmultiplext mobiltelefonisystem med ett effektivt utnyttjande av varje tidsram |
| GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| ZA94170B (en) * | 1993-01-20 | 1995-03-15 | Soltec Res Pty Ltd | Ectoparasiticidal formulation |
| AUPM437194A0 (en) * | 1994-03-11 | 1994-03-31 | Commonwealth Scientific And Industrial Research Organisation | Pesticide formulation |
| GB9601128D0 (en) * | 1995-08-11 | 1996-03-20 | Pfizer Ltd | Parasiticidal compounds |
| JP4068142B2 (ja) | 1995-08-11 | 2008-03-26 | ノボザイムス アクティーゼルスカブ | 新規の脂肪分解酵素 |
| JPH0987111A (ja) * | 1995-09-27 | 1997-03-31 | Sumitomo Chem Co Ltd | 害虫駆除用毒餌剤 |
| FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| ATE236883T1 (de) * | 1995-12-19 | 2003-04-15 | Bayer Cropscience Sa | Neue 1-aryl pyrazol derivate und ihre verwendung als schädlingsbekämpfungsmittel |
| GR970100096A (el) * | 1996-03-29 | 1997-11-28 | Merial | Εξωτερικη διαταξη κατα των παρασιτων για βοοειδη με βαση τη ν-φαινυλπυραζολη, ειδικα σκουλαρικια. |
| IE80657B1 (en) * | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
| IE970215A1 (en) * | 1996-03-29 | 1997-10-08 | Rhone Merieux | Direct pour-on skin solution for antiparasitic use in cattle¹and sheep |
| GR1002899B (el) * | 1996-03-29 | 1998-05-11 | Rhone Merieux | Περιλαιμιο κατα ψυλλων και κροτωνων για σκυλους και γατες, με βαση ν-φαινυλπυραζολη |
| TW524667B (en) | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| US7100379B2 (en) * | 2003-08-14 | 2006-09-05 | Samsung Electronics Co., Ltd. | Water supply control apparatus and method for ice maker |
-
1997
- 1997-10-24 TW TW086115810A patent/TW524667B/zh not_active IP Right Cessation
- 1997-11-25 CN CN97180334A patent/CN1106386C/zh not_active Expired - Fee Related
- 1997-11-25 ES ES97951271T patent/ES2191870T3/es not_active Expired - Lifetime
- 1997-11-25 CZ CZ19991951A patent/CZ295295B6/cs not_active IP Right Cessation
- 1997-11-25 IL IL12986697A patent/IL129866A/en not_active IP Right Cessation
- 1997-11-25 JP JP52517898A patent/JP3950483B2/ja not_active Expired - Fee Related
- 1997-11-25 PT PT97951271T patent/PT946515E/pt unknown
- 1997-11-25 UA UA99052678A patent/UA60321C2/uk unknown
- 1997-11-25 AU AU54859/98A patent/AU720705B2/en not_active Ceased
- 1997-11-25 KR KR1019997005032A patent/KR100354311B1/ko not_active IP Right Cessation
- 1997-11-25 HU HU0000544A patent/HUP0000544A3/hu unknown
- 1997-11-25 AT AT97951271T patent/ATE233736T1/de active
- 1997-11-25 CA CA002273951A patent/CA2273951C/fr not_active Expired - Fee Related
- 1997-11-25 ID IDW990469A patent/ID21556A/id unknown
- 1997-11-25 DK DK97951271T patent/DK0946515T3/da active
- 1997-11-25 DE DE69719547T patent/DE69719547T2/de not_active Expired - Lifetime
- 1997-11-25 NZ NZ335611A patent/NZ335611A/xx not_active IP Right Cessation
- 1997-11-25 RS YUP-252/99A patent/RS49720B/sr unknown
- 1997-11-25 US US09/319,310 patent/US6075043A/en not_active Expired - Lifetime
- 1997-11-25 EA EA199900447A patent/EA002278B1/ru not_active IP Right Cessation
- 1997-11-25 EP EP97951271A patent/EP0946515B1/fr not_active Expired - Lifetime
- 1997-11-25 WO PCT/EP1997/006697 patent/WO1998024767A1/fr active IP Right Grant
- 1997-11-25 PL PL333922A patent/PL190926B1/pl not_active IP Right Cessation
- 1997-11-25 SK SK740-99A patent/SK285203B6/sk not_active IP Right Cessation
- 1997-11-25 BR BR9713565-8A patent/BR9713565A/pt not_active Application Discontinuation
- 1997-11-28 PA PA19978442101A patent/PA8442101A1/es unknown
- 1997-12-01 PE PE1997001081A patent/PE20199A1/es not_active Application Discontinuation
- 1997-12-02 CO CO97070532A patent/CO5031251A1/es unknown
- 1997-12-03 AR ARP970105679A patent/AR013879A1/es active IP Right Grant
- 1997-12-03 TN TNTNSN97197A patent/TNSN97197A1/fr unknown
- 1997-12-03 UY UY24798A patent/UY24798A1/es not_active IP Right Cessation
- 1997-12-03 DZ DZ970210A patent/DZ2360A1/fr active
- 1997-12-03 MA MA24885A patent/MA24414A1/fr unknown
- 1997-12-04 MY MYPI97005853A patent/MY117021A/en unknown
- 1997-12-04 HR HR970663A patent/HRP970663B1/xx not_active IP Right Cessation
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1998
- 1998-03-12 UY UY24923A patent/UY24923A1/es not_active IP Right Cessation
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1999
- 1999-05-11 IS IS5050A patent/IS1982B/is unknown
- 1999-05-28 OA OA9900114A patent/OA11055A/en unknown
- 1999-06-01 BG BG103454A patent/BG64127B1/bg unknown
- 1999-06-04 NO NO992736A patent/NO992736D0/no unknown
- 1999-06-04 NO NO19992732A patent/NO313518B1/no not_active IP Right Cessation
-
2000
- 2000-02-23 US US09/511,885 patent/US6268509B1/en not_active Expired - Fee Related
- 2000-12-21 HK HK00108339A patent/HK1029111A1/xx not_active IP Right Cessation
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2007
- 2007-03-02 JP JP2007053011A patent/JP2007211016A/ja active Pending
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Legal Events
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| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: ZOETIS LLC, US |
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| MM1K | Lapsed by not paying the annual fees |