SK12502003A3 - Halogénsubstituované chinolínové deriváty a prostriedok na kontrolu ektoparazitov - Google Patents
Halogénsubstituované chinolínové deriváty a prostriedok na kontrolu ektoparazitov Download PDFInfo
- Publication number
- SK12502003A3 SK12502003A3 SK1250-2003A SK12502003A SK12502003A3 SK 12502003 A3 SK12502003 A3 SK 12502003A3 SK 12502003 A SK12502003 A SK 12502003A SK 12502003 A3 SK12502003 A3 SK 12502003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- difluoroquinoline
- ethyl
- dimethyl
- compound
- Prior art date
Links
- 244000078703 ectoparasite Species 0.000 title claims abstract description 24
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 91
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- KFHKBLDXFJISQG-UHFFFAOYSA-N (2-ethyl-5,6-difluoro-3-methylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(CC)=NC2=CC=C(F)C(F)=C2C=1OC(=O)C1CC1 KFHKBLDXFJISQG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- BQRPVRURXOQHAE-UHFFFAOYSA-N (5,6-difluoro-2,3-dimethylquinolin-4-yl) acetate Chemical compound C1=C(F)C(F)=C2C(OC(=O)C)=C(C)C(C)=NC2=C1 BQRPVRURXOQHAE-UHFFFAOYSA-N 0.000 claims description 5
- HLVRJYILZOXTAC-UHFFFAOYSA-N (5-chloro-2-ethyl-6-fluoro-3-methylquinolin-4-yl) acetate Chemical compound C1=C(F)C(Cl)=C2C(OC(C)=O)=C(C)C(CC)=NC2=C1 HLVRJYILZOXTAC-UHFFFAOYSA-N 0.000 claims description 5
- 241000258242 Siphonaptera Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 241001427556 Anoplura Species 0.000 claims description 4
- 241001481698 Mesostigmata Species 0.000 claims description 4
- TXRJEDJSNCDCTA-UHFFFAOYSA-N (2-ethyl-5,6-difluoro-3-methylquinolin-4-yl) methyl carbonate Chemical compound C1=C(F)C(F)=C2C(OC(=O)OC)=C(C)C(CC)=NC2=C1 TXRJEDJSNCDCTA-UHFFFAOYSA-N 0.000 claims description 3
- BQIOUYRVROSONU-UHFFFAOYSA-N (5,6-dichloro-2,3-dimethylquinolin-4-yl) acetate Chemical compound C1=C(Cl)C(Cl)=C2C(OC(=O)C)=C(C)C(C)=NC2=C1 BQIOUYRVROSONU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- MZILRTVVUDVOJL-UHFFFAOYSA-N but-3-ynyl (2-ethyl-5,6-difluoro-3-methylquinolin-4-yl) carbonate Chemical compound C1=C(F)C(F)=C2C(OC(=O)OCCC#C)=C(C)C(CC)=NC2=C1 MZILRTVVUDVOJL-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- IPVRCPYFJOEQQK-UHFFFAOYSA-N (2-ethyl-5,6-difluoro-3-methylquinolin-4-yl) prop-2-ynyl carbonate Chemical compound C1=C(F)C(F)=C2C(OC(=O)OCC#C)=C(C)C(CC)=NC2=C1 IPVRCPYFJOEQQK-UHFFFAOYSA-N 0.000 claims description 2
- ZIVYTLMPKZDZGO-UHFFFAOYSA-N (5,6-dichloro-2,3-dimethylquinolin-4-yl) methyl carbonate Chemical compound C1=C(Cl)C(Cl)=C2C(OC(=O)OC)=C(C)C(C)=NC2=C1 ZIVYTLMPKZDZGO-UHFFFAOYSA-N 0.000 claims description 2
- AGALAUZNOAQELQ-UHFFFAOYSA-N (5,6-difluoro-2,3-dimethylquinolin-4-yl) methyl carbonate Chemical compound C1=C(F)C(F)=C2C(OC(=O)OC)=C(C)C(C)=NC2=C1 AGALAUZNOAQELQ-UHFFFAOYSA-N 0.000 claims description 2
- YQTGCPFCADMIEC-UHFFFAOYSA-N (5,6-difluoro-2,3-dimethylquinolin-4-yl) prop-2-ynyl carbonate Chemical compound C1=C(F)C(F)=C2C(OC(=O)OCC#C)=C(C)C(C)=NC2=C1 YQTGCPFCADMIEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- VZKASZPBERNUQD-UHFFFAOYSA-N but-3-ynyl (5,6-difluoro-2,3-dimethylquinolin-4-yl) carbonate Chemical compound C1=C(F)C(F)=C2C(OC(=O)OCCC#C)=C(C)C(C)=NC2=C1 VZKASZPBERNUQD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 8
- 241001465754 Metazoa Species 0.000 abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 2
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 153
- 239000000243 solution Substances 0.000 description 89
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 50
- 239000007858 starting material Substances 0.000 description 49
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 44
- 239000002904 solvent Substances 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000000725 suspension Substances 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 23
- 230000008020 evaporation Effects 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 22
- 235000017557 sodium bicarbonate Nutrition 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000499 gel Substances 0.000 description 19
- 239000003480 eluent Substances 0.000 description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- 239000012312 sodium hydride Substances 0.000 description 17
- 229910000104 sodium hydride Inorganic materials 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- PSEIYDYNKLOWMO-UHFFFAOYSA-N 5,6-difluoro-2,3-dimethyl-1h-quinolin-4-one Chemical compound C1=C(F)C(F)=C2C(O)=C(C)C(C)=NC2=C1 PSEIYDYNKLOWMO-UHFFFAOYSA-N 0.000 description 9
- 241000271566 Aves Species 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- CAESMXLPONVKMM-UHFFFAOYSA-N 2-ethyl-5,6-difluoro-3-methyl-1h-quinolin-4-one Chemical compound C1=C(F)C(F)=C2C(O)=C(C)C(CC)=NC2=C1 CAESMXLPONVKMM-UHFFFAOYSA-N 0.000 description 6
- XRJDVKKMKIPHJA-UHFFFAOYSA-N 2-ethyl-6,7-difluoro-3-methyl-1h-quinolin-4-one Chemical compound FC1=C(F)C=C2C(O)=C(C)C(CC)=NC2=C1 XRJDVKKMKIPHJA-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- HJYUQFUJRZFCLM-UHFFFAOYSA-N 2,3-difluoroquinoline Chemical compound C1=CC=C2N=C(F)C(F)=CC2=C1 HJYUQFUJRZFCLM-UHFFFAOYSA-N 0.000 description 5
- AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 5
- XIKGCYZXZDHVSW-UHFFFAOYSA-N 5-chloro-2-ethyl-6-fluoro-3-methyl-1h-quinolin-4-one Chemical compound C1=C(F)C(Cl)=C2C(O)=C(C)C(CC)=NC2=C1 XIKGCYZXZDHVSW-UHFFFAOYSA-N 0.000 description 5
- ZNEFCNVCENDWJZ-UHFFFAOYSA-N 6,7-difluoro-2,3-dimethyl-1h-quinolin-4-one Chemical compound FC1=C(F)C=C2C(O)=C(C)C(C)=NC2=C1 ZNEFCNVCENDWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- NJSLJTPFHIIDIJ-UHFFFAOYSA-N (5,6-difluoro-2,3-dimethylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(C)=NC2=CC=C(F)C(F)=C2C=1OC(=O)C1CC1 NJSLJTPFHIIDIJ-UHFFFAOYSA-N 0.000 description 4
- BCGHPTDHCRYICC-UHFFFAOYSA-N (5-chloro-2-ethyl-6-fluoro-3-methylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(CC)=NC2=CC=C(F)C(Cl)=C2C=1OC(=O)C1CC1 BCGHPTDHCRYICC-UHFFFAOYSA-N 0.000 description 4
- NZHDRVRTQLVBTK-UHFFFAOYSA-N (7-chloro-6-fluoro-2,3-dimethylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(C)=NC2=CC(Cl)=C(F)C=C2C=1OC(=O)C1CC1 NZHDRVRTQLVBTK-UHFFFAOYSA-N 0.000 description 4
- QSPYQKJMYXCIIQ-UHFFFAOYSA-N 7-chloro-2-ethyl-6-fluoro-3-methyl-1h-quinolin-4-one Chemical compound ClC1=C(F)C=C2C(O)=C(C)C(CC)=NC2=C1 QSPYQKJMYXCIIQ-UHFFFAOYSA-N 0.000 description 4
- GFECDLNIHZIGIF-UHFFFAOYSA-N 7-chloro-6-fluoro-2,3-dimethyl-1h-quinolin-4-one Chemical compound ClC1=C(F)C=C2C(O)=C(C)C(C)=NC2=C1 GFECDLNIHZIGIF-UHFFFAOYSA-N 0.000 description 4
- 241000238876 Acari Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 210000000941 bile Anatomy 0.000 description 4
- 238000009395 breeding Methods 0.000 description 4
- 230000001488 breeding effect Effects 0.000 description 4
- 238000007598 dipping method Methods 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- TWXCDUAVTIGUBY-UHFFFAOYSA-N (2-ethyl-5,6-difluoro-3-methylquinolin-4-yl) acetate Chemical compound C1=C(F)C(F)=C2C(OC(C)=O)=C(C)C(CC)=NC2=C1 TWXCDUAVTIGUBY-UHFFFAOYSA-N 0.000 description 3
- YKMVYQPQGUKIAK-UHFFFAOYSA-N (2-ethyl-6,7-difluoro-3-methylquinolin-4-yl) acetate Chemical compound FC1=C(F)C=C2C(OC(C)=O)=C(C)C(CC)=NC2=C1 YKMVYQPQGUKIAK-UHFFFAOYSA-N 0.000 description 3
- GBJBYCUNPFZNFT-UHFFFAOYSA-N (2-ethyl-6,7-difluoro-3-methylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(CC)=NC2=CC(F)=C(F)C=C2C=1OC(=O)C1CC1 GBJBYCUNPFZNFT-UHFFFAOYSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- FLNJOEYOCUWQOY-AATRIKPKSA-N (5,6-difluoro-2,3-dimethylquinolin-4-yl) (e)-3-chloroprop-2-enoate Chemical compound C1=C(F)C(F)=C2C(OC(=O)\C=C\Cl)=C(C)C(C)=NC2=C1 FLNJOEYOCUWQOY-AATRIKPKSA-N 0.000 description 3
- PDXZGPMVVOQXHP-UHFFFAOYSA-N (5-chloro-2-ethyl-6-fluoro-3-methylquinolin-4-yl) propan-2-yl carbonate Chemical compound C1=C(F)C(Cl)=C2C(OC(=O)OC(C)C)=C(C)C(CC)=NC2=C1 PDXZGPMVVOQXHP-UHFFFAOYSA-N 0.000 description 3
- BOLDWWOGIAJHOJ-UHFFFAOYSA-N (5-chloro-6-fluoro-2,3-dimethylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(C)=NC2=CC=C(F)C(Cl)=C2C=1OC(=O)C1CC1 BOLDWWOGIAJHOJ-UHFFFAOYSA-N 0.000 description 3
- FXEAMAUHHPRGKG-UHFFFAOYSA-N (6,7-difluoro-2,3-dimethylquinolin-4-yl) acetate Chemical compound FC1=C(F)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1 FXEAMAUHHPRGKG-UHFFFAOYSA-N 0.000 description 3
- UMMSAPJFKHGLEN-UHFFFAOYSA-N (6,7-difluoro-2,3-dimethylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(C)=NC2=CC(F)=C(F)C=C2C=1OC(=O)C1CC1 UMMSAPJFKHGLEN-UHFFFAOYSA-N 0.000 description 3
- OHEZZWDYYOOBGU-UHFFFAOYSA-N (7-chloro-2-ethyl-6-fluoro-3-methylquinolin-4-yl) cyclopropanecarboxylate Chemical compound CC=1C(CC)=NC2=CC(Cl)=C(F)C=C2C=1OC(=O)C1CC1 OHEZZWDYYOOBGU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 3
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Chemical group 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000037368 penetrate the skin Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Insulating Materials (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001114459 | 2001-04-12 | ||
| PCT/JP2002/003685 WO2002083644A1 (en) | 2001-04-12 | 2002-04-12 | Halogenated quinoline derivatives and ectoparasite controllers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK12502003A3 true SK12502003A3 (sk) | 2004-04-06 |
Family
ID=18965525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1250-2003A SK12502003A3 (sk) | 2001-04-12 | 2002-04-12 | Halogénsubstituované chinolínové deriváty a prostriedok na kontrolu ektoparazitov |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7022855B2 (cs) |
| EP (1) | EP1386914B1 (cs) |
| JP (1) | JP4242156B2 (cs) |
| KR (1) | KR100721628B1 (cs) |
| CN (1) | CN1310889C (cs) |
| AT (1) | ATE486060T1 (cs) |
| AU (1) | AU2002251459B2 (cs) |
| BR (1) | BR0208759A (cs) |
| CA (1) | CA2443484C (cs) |
| CZ (1) | CZ20032758A3 (cs) |
| DE (1) | DE60238116D1 (cs) |
| HU (1) | HUP0303856A3 (cs) |
| IL (1) | IL158277A0 (cs) |
| MA (1) | MA26163A1 (cs) |
| MX (1) | MXPA03009044A (cs) |
| NO (1) | NO20034252L (cs) |
| NZ (1) | NZ528040A (cs) |
| PL (1) | PL366867A1 (cs) |
| RU (1) | RU2003132870A (cs) |
| SK (1) | SK12502003A3 (cs) |
| WO (1) | WO2002083644A1 (cs) |
| ZA (1) | ZA200307573B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0314987A (pt) * | 2002-10-11 | 2005-08-09 | Meiji Seika Kaisha | Composição em mistura para o controle de ectoparasitas de manìferos e aves, método para o contrloe de um ectoparasita de mamìferos e aves, combinação, e, uso da mesma |
| BRPI0819112A2 (pt) * | 2007-11-09 | 2014-10-07 | Novartis Ag | Dihidroquinolinonas como ectoparasiticidas |
| EP2370411A4 (en) * | 2008-12-05 | 2012-10-24 | Univ Oregon Health & Science | COMPOUNDS WITH ANTIPARASITIC OR ANTI-INFECTIOUS EFFECT |
| US8598354B2 (en) | 2008-12-05 | 2013-12-03 | University Of South Florida | Compounds having antiparasitic or anti-infectious activity |
| KR102490180B1 (ko) * | 2017-03-17 | 2023-01-18 | 메이지 세이카 파루마 가부시키가이샤 | 중기문아목 진드기류의 방제제 |
| CN108689928B (zh) * | 2018-07-19 | 2020-05-26 | 山东省联合农药工业有限公司 | 一种喹啉类衍生物及其制备方法与用途 |
| JP7389750B2 (ja) * | 2018-09-14 | 2023-11-30 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | 中気門亜目ダニ類の防除用組成物 |
| CN110301441B (zh) * | 2019-07-09 | 2021-05-04 | 云南大学 | 氯喹防治根结线虫的新用途 |
| CN111205223B (zh) * | 2020-03-03 | 2021-06-22 | 山东省联合农药工业有限公司 | 喹啉类衍生物及其制备方法与用途 |
| CN114957116A (zh) * | 2022-07-01 | 2022-08-30 | 浙江工业大学 | 2,3-二甲基-8-氟喹啉-4-酯类化合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194617A (en) * | 1988-12-17 | 1993-03-16 | Meiji Seika Kaisha, Ltd. | 2,3-disubstituted-4-hydroxyquinoline derivatives |
| JPH0796481B2 (ja) * | 1989-07-06 | 1995-10-18 | 明治製菓株式会社 | 殺虫、殺ダニ剤 |
| DE69030030T2 (de) * | 1989-07-07 | 1997-06-26 | Meiji Seika Co | 4-Acyloxychinolin-Derivate und diese enthaltende insektizide und akarizide Mittel |
| JPH08311032A (ja) * | 1995-05-18 | 1996-11-26 | Eisai Co Ltd | α，β−不飽和ケトン誘導体 |
| TW521072B (en) * | 1997-06-02 | 2003-02-21 | Meiji Seika Kaisha | 4-quinolinol derivatives and fungicides containing the same as an active ingredient used for agriculture and horticulture |
| JP2001097866A (ja) * | 1999-07-28 | 2001-04-10 | Meiji Seika Kaisha Ltd | 抗ヘリコバクター・ピロリ剤 |
| GB0023918D0 (en) * | 2000-09-29 | 2000-11-15 | King S College London | Antiparasitic compounds |
| JP3912183B2 (ja) | 2001-05-25 | 2007-05-09 | 日立電線株式会社 | ポリイミド及び積層体 |
-
2002
- 2002-04-12 AT AT02720439T patent/ATE486060T1/de not_active IP Right Cessation
- 2002-04-12 RU RU2003132870/04A patent/RU2003132870A/ru not_active Application Discontinuation
- 2002-04-12 KR KR1020037013245A patent/KR100721628B1/ko not_active Expired - Fee Related
- 2002-04-12 EP EP02720439A patent/EP1386914B1/en not_active Expired - Lifetime
- 2002-04-12 JP JP2002581401A patent/JP4242156B2/ja not_active Expired - Fee Related
- 2002-04-12 PL PL02366867A patent/PL366867A1/xx unknown
- 2002-04-12 HU HU0303856A patent/HUP0303856A3/hu unknown
- 2002-04-12 AU AU2002251459A patent/AU2002251459B2/en not_active Ceased
- 2002-04-12 CA CA2443484A patent/CA2443484C/en not_active Expired - Fee Related
- 2002-04-12 DE DE60238116T patent/DE60238116D1/de not_active Expired - Lifetime
- 2002-04-12 WO PCT/JP2002/003685 patent/WO2002083644A1/ja not_active Ceased
- 2002-04-12 CZ CZ20032758A patent/CZ20032758A3/cs unknown
- 2002-04-12 MX MXPA03009044A patent/MXPA03009044A/es not_active Application Discontinuation
- 2002-04-12 CN CNB028080742A patent/CN1310889C/zh not_active Expired - Fee Related
- 2002-04-12 BR BR0208759-6A patent/BR0208759A/pt not_active Application Discontinuation
- 2002-04-12 IL IL15827702A patent/IL158277A0/xx unknown
- 2002-04-12 NZ NZ528040A patent/NZ528040A/en unknown
- 2002-04-12 SK SK1250-2003A patent/SK12502003A3/sk unknown
-
2003
- 2003-09-24 NO NO20034252A patent/NO20034252L/no not_active Application Discontinuation
- 2003-09-29 ZA ZA200307573A patent/ZA200307573B/en unknown
- 2003-10-09 MA MA27349A patent/MA26163A1/fr unknown
- 2003-10-09 US US10/681,192 patent/US7022855B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2443484C (en) | 2010-10-19 |
| MXPA03009044A (es) | 2004-02-12 |
| RU2003132870A (ru) | 2005-02-27 |
| CN1501918A (zh) | 2004-06-02 |
| PL366867A1 (en) | 2005-02-07 |
| ATE486060T1 (de) | 2010-11-15 |
| ZA200307573B (en) | 2004-09-29 |
| CA2443484A1 (en) | 2002-10-24 |
| KR100721628B1 (ko) | 2007-05-23 |
| HUP0303856A3 (en) | 2005-06-28 |
| CZ20032758A3 (cs) | 2004-01-14 |
| EP1386914A4 (en) | 2005-03-23 |
| CN1310889C (zh) | 2007-04-18 |
| NO20034252L (no) | 2003-12-08 |
| US20040087618A1 (en) | 2004-05-06 |
| BR0208759A (pt) | 2004-09-14 |
| JPWO2002083644A1 (ja) | 2004-08-05 |
| EP1386914B1 (en) | 2010-10-27 |
| NZ528040A (en) | 2005-07-29 |
| DE60238116D1 (de) | 2010-12-09 |
| IL158277A0 (en) | 2004-05-12 |
| US7022855B2 (en) | 2006-04-04 |
| NO20034252D0 (no) | 2003-09-24 |
| KR20030088130A (ko) | 2003-11-17 |
| HUP0303856A2 (hu) | 2004-03-29 |
| WO2002083644A1 (en) | 2002-10-24 |
| AU2002251459B2 (en) | 2007-05-10 |
| JP4242156B2 (ja) | 2009-03-18 |
| MA26163A1 (fr) | 2004-07-01 |
| EP1386914A1 (en) | 2004-02-04 |
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