IL122281A - History of pyrazole acting against parasites, process for their preparation and veterinary medicinal preparations containing them - Google Patents
History of pyrazole acting against parasites, process for their preparation and veterinary medicinal preparations containing themInfo
- Publication number
- IL122281A IL122281A IL12228196A IL12228196A IL122281A IL 122281 A IL122281 A IL 122281A IL 12228196 A IL12228196 A IL 12228196A IL 12228196 A IL12228196 A IL 12228196A IL 122281 A IL122281 A IL 122281A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- group
- halogen
- optionally substituted
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 89
- 238000002360 preparation method Methods 0.000 title claims description 62
- 238000000034 method Methods 0.000 title claims description 49
- 230000000590 parasiticidal effect Effects 0.000 title claims description 9
- 150000003217 pyrazoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 328
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 114
- 150000002367 halogens Chemical class 0.000 claims abstract description 113
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- -1 CSNH2 Chemical group 0.000 claims abstract description 17
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 32
- 241000894007 species Species 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 238000009472 formulation Methods 0.000 claims description 15
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 230000003071 parasitic effect Effects 0.000 claims description 7
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 claims description 6
- 206010061217 Infestation Diseases 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 5
- 229910018482 SF5 Inorganic materials 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 244000045947 parasite Species 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- 229940045803 cuprous chloride Drugs 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 390
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 352
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 154
- 239000000243 solution Substances 0.000 description 148
- 239000007787 solid Substances 0.000 description 112
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 96
- 239000000741 silica gel Substances 0.000 description 88
- 229910002027 silica gel Inorganic materials 0.000 description 88
- 239000011541 reaction mixture Substances 0.000 description 87
- 238000004440 column chromatography Methods 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- 238000001704 evaporation Methods 0.000 description 71
- 230000008020 evaporation Effects 0.000 description 70
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 67
- 239000012044 organic layer Substances 0.000 description 55
- 238000005160 1H NMR spectroscopy Methods 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000003756 stirring Methods 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000012267 brine Substances 0.000 description 27
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
- 238000010992 reflux Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000012043 crude product Substances 0.000 description 17
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 17
- 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 16
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 15
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 15
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 10
- 241000238876 Acari Species 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 241000238421 Arthropoda Species 0.000 description 9
- 241000254173 Coleoptera Species 0.000 description 9
- 241000255925 Diptera Species 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 9
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 230000002411 adverse Effects 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 229910001961 silver nitrate Inorganic materials 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
- 241000256602 Isoptera Species 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 238000004452 microanalysis Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 230000006978 adaptation Effects 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 244000000013 helminth Species 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 4
- 239000012285 osmium tetroxide Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 241000223924 Eimeria Species 0.000 description 3
- 241000258937 Hemiptera Species 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 235000013594 poultry meat Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241000294569 Aphelenchoides Species 0.000 description 2
- 241000726103 Atta Species 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- 208000003495 Coccidiosis Diseases 0.000 description 2
- 241001427559 Collembola Species 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- 241001635274 Cydia pomonella Species 0.000 description 2
- 241000268912 Damalinia Species 0.000 description 2
- 241001124144 Dermaptera Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000399934 Ditylenchus Species 0.000 description 2
- 241000399949 Ditylenchus dipsaci Species 0.000 description 2
- 241000353522 Earias insulana Species 0.000 description 2
- 241000223931 Eimeria acervulina Species 0.000 description 2
- 241000499563 Eimeria necatrix Species 0.000 description 2
- 241000256257 Heliothis Species 0.000 description 2
- 241000256244 Heliothis virescens Species 0.000 description 2
- 241000590466 Heterotermes Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000577496 Hypothenemus hampei Species 0.000 description 2
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Classifications
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- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- 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
- C07D231/40—Acylated on said nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9516454.7A GB9516454D0 (en) | 1995-08-11 | 1995-08-11 | Parasiticidal compounds |
| GBGB9601128.3A GB9601128D0 (en) | 1995-08-11 | 1996-01-19 | Parasiticidal compounds |
| PCT/EP1996/003501 WO1997007102A1 (en) | 1995-08-11 | 1996-08-05 | Parasiticidal compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL122281A0 IL122281A0 (en) | 1998-04-05 |
| IL122281A true IL122281A (en) | 2002-11-10 |
Family
ID=26307556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12228196A IL122281A (en) | 1995-08-11 | 1996-08-05 | History of pyrazole acting against parasites, process for their preparation and veterinary medicinal preparations containing them |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6255333B1 (zh) |
| EP (1) | EP0871617B1 (zh) |
| JP (1) | JP3154413B2 (zh) |
| KR (1) | KR100310571B1 (zh) |
| CN (1) | CN1159298C (zh) |
| AR (1) | AR003976A1 (zh) |
| AT (1) | ATE208762T1 (zh) |
| AU (1) | AU710736B2 (zh) |
| BR (1) | BR9610608A (zh) |
| CA (1) | CA2229173C (zh) |
| CO (1) | CO4480737A1 (zh) |
| CZ (1) | CZ292275B6 (zh) |
| DE (1) | DE69617041T2 (zh) |
| DK (1) | DK0871617T3 (zh) |
| ES (1) | ES2165520T3 (zh) |
| GB (1) | GB9601128D0 (zh) |
| HU (1) | HUP9802865A3 (zh) |
| IL (1) | IL122281A (zh) |
| MX (1) | MX9801147A (zh) |
| NO (1) | NO310459B1 (zh) |
| NZ (1) | NZ316473A (zh) |
| PL (1) | PL185765B1 (zh) |
| PT (1) | PT871617E (zh) |
| RU (1) | RU2151766C1 (zh) |
| TW (1) | TW381082B (zh) |
| WO (1) | WO1997007102A1 (zh) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028126A1 (en) * | 1996-01-30 | 1997-08-07 | Takeda Chemical Industries, Ltd. | Arylpyrazole insecticides |
| 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 |
| AR021608A1 (es) * | 1998-12-11 | 2002-07-31 | Merial Ltd | Represion de artropodos en animales |
| US6531501B1 (en) | 1998-12-11 | 2003-03-11 | Aventis Cropscience, S.A. | Control of arthropods in animals |
| GB9916052D0 (en) * | 1999-07-08 | 1999-09-08 | Pfizer Ltd | Anthelmintic compositions |
| CN1096267C (zh) * | 1999-08-19 | 2002-12-18 | 李春生 | 一种治疗鸡住白细胞原虫药物 |
| JP2003516941A (ja) | 1999-12-02 | 2003-05-20 | アベンティス クロップサイエンス ソシエテ アノニム | 動物における節足動物の制御 |
| AU4589701A (en) | 2000-03-24 | 2001-10-08 | Cocensys Inc | Aryl substituted pyrazoles, triazoles and tetrazoles, and the use thereof |
| SI1483245T1 (sl) * | 2002-03-05 | 2007-02-28 | Merial Ltd | 5-substituirani alkilaminopirazolni derivati kot pesticidi |
| US6663876B2 (en) | 2002-04-29 | 2003-12-16 | Piedmont Pharmaceuticals, Llc | Methods and compositions for treating ectoparasite infestation |
| AR040082A1 (es) * | 2002-05-22 | 2005-03-16 | Novartis Ag | Derivados de n-acilaminoacetonitrilo y su uso para el control de parasitos |
| DE10300124A1 (de) * | 2003-01-07 | 2004-07-15 | Bayer Ag | Verfahren zur Herstellung von Arylalkinen |
| CH697574B1 (de) * | 2003-01-07 | 2008-12-15 | Lanxess Deutschland Gmbh | Pyrazolylarylalkine. |
| US7514464B2 (en) * | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
| GB0329314D0 (en) | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
| GB0413970D0 (en) * | 2004-06-22 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| ES2341974T3 (es) * | 2004-06-26 | 2010-06-30 | Merial Limited | Derivados de 1-arilpirazol como agentes pesticidas. |
| US20080146643A1 (en) * | 2005-06-15 | 2008-06-19 | Pfizer Limited | Combination |
| WO2006134459A1 (en) * | 2005-06-15 | 2006-12-21 | Pfizer Limited | Substituted arylpyrazoles |
| US20080176865A1 (en) * | 2005-06-15 | 2008-07-24 | Pfizer Limited | Substituted arylpyrazoles |
| KR20080016648A (ko) | 2005-06-15 | 2008-02-21 | 화이자 리미티드 | 기생충 방제용 치환된 아릴피라졸 |
| US7645786B2 (en) | 2005-06-15 | 2010-01-12 | Pfizer Inc. | Substituted arylpyrazoles |
| US9447042B2 (en) * | 2011-03-02 | 2016-09-20 | The University Of Tokyo | Endoparasite control agent |
| CN103613543B (zh) * | 2013-11-05 | 2015-09-02 | 温州大学 | 一种氟虫腈衍生物的制备方法 |
| US10941132B2 (en) * | 2016-01-05 | 2021-03-09 | Hua Medicine (Shanghai) Ltd. | Pyrazole derivatives |
| CN105541821B (zh) * | 2016-01-28 | 2018-05-18 | 中南民族大学 | 噁嗪酮化芳基吡唑型化合物及其超声波辐射合成方法和应用 |
| KR101691604B1 (ko) | 2016-03-29 | 2017-01-02 | 주식회사 한일라바테크 | 양변기용 패킹 슬리브 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| US5091378A (en) * | 1987-05-22 | 1992-02-25 | E. R. Squibb & Sons, Inc. | Phosphorus-containing HMG-CoA reductase inhibitors, new intermediates and method |
| DE69408950T2 (de) | 1993-12-14 | 1998-10-15 | Mitsubishi Chem Corp | N-Pyrazolylcarbamatderivate und Fungizide für Landwirtschaft und Gartenbau, die diese als aktive Bestandteile erhalten, Produktion und Zwischenprodukte |
-
1996
- 1996-01-19 GB GBGB9601128.3A patent/GB9601128D0/en active Pending
- 1996-07-13 TW TW085108511A patent/TW381082B/zh not_active IP Right Cessation
- 1996-08-05 AU AU68712/96A patent/AU710736B2/en not_active Ceased
- 1996-08-05 PL PL96324995A patent/PL185765B1/pl not_active IP Right Cessation
- 1996-08-05 DE DE69617041T patent/DE69617041T2/de not_active Expired - Fee Related
- 1996-08-05 PT PT96929222T patent/PT871617E/pt unknown
- 1996-08-05 WO PCT/EP1996/003501 patent/WO1997007102A1/en active IP Right Grant
- 1996-08-05 BR BR9610608A patent/BR9610608A/pt not_active IP Right Cessation
- 1996-08-05 CZ CZ1998392A patent/CZ292275B6/cs not_active IP Right Cessation
- 1996-08-05 AT AT96929222T patent/ATE208762T1/de not_active IP Right Cessation
- 1996-08-05 JP JP50891197A patent/JP3154413B2/ja not_active Expired - Fee Related
- 1996-08-05 DK DK96929222T patent/DK0871617T3/da active
- 1996-08-05 US US09/011,815 patent/US6255333B1/en not_active Expired - Fee Related
- 1996-08-05 ES ES96929222T patent/ES2165520T3/es not_active Expired - Lifetime
- 1996-08-05 HU HU9802865A patent/HUP9802865A3/hu unknown
- 1996-08-05 KR KR1019980700923A patent/KR100310571B1/ko not_active IP Right Cessation
- 1996-08-05 EP EP96929222A patent/EP0871617B1/en not_active Expired - Lifetime
- 1996-08-05 RU RU98102359/04A patent/RU2151766C1/ru not_active IP Right Cessation
- 1996-08-05 CN CNB961962070A patent/CN1159298C/zh not_active Expired - Fee Related
- 1996-08-05 NZ NZ316473A patent/NZ316473A/en unknown
- 1996-08-05 IL IL12228196A patent/IL122281A/en not_active IP Right Cessation
- 1996-08-05 MX MX9801147A patent/MX9801147A/es not_active IP Right Cessation
- 1996-08-05 CA CA002229173A patent/CA2229173C/en not_active Expired - Fee Related
- 1996-08-09 CO CO96042283A patent/CO4480737A1/es unknown
- 1996-08-09 AR ARP960103932A patent/AR003976A1/es unknown
-
1998
- 1998-02-10 NO NO19980570A patent/NO310459B1/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |