NO320018B1 - 1-arylpyrazolforbindelse, preparat inneholdende den samme samt anvendelse derav. - Google Patents
1-arylpyrazolforbindelse, preparat inneholdende den samme samt anvendelse derav. Download PDFInfo
- Publication number
- NO320018B1 NO320018B1 NO20012820A NO20012820A NO320018B1 NO 320018 B1 NO320018 B1 NO 320018B1 NO 20012820 A NO20012820 A NO 20012820A NO 20012820 A NO20012820 A NO 20012820A NO 320018 B1 NO320018 B1 NO 320018B1
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- Norway
- Prior art keywords
- alkyl
- halo
- formula
- animal
- compound
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 10
- -1 1-arylpyrazole compound Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 63
- 241001465754 Metazoa Species 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000002895 emetic Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 244000045947 parasite Species 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 241000238876 Acari Species 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 241000282326 Felis catus Species 0.000 description 7
- 241000258242 Siphonaptera Species 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 244000144972 livestock Species 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RRXZEWZJQKBZCP-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methylamino)-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile Chemical compound CNC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RRXZEWZJQKBZCP-UHFFFAOYSA-N 0.000 description 4
- 241000238421 Arthropoda Species 0.000 description 4
- 241000258924 Ctenocephalides felis Species 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 3
- 241001414835 Cimicidae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005899 Fipronil Substances 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 229940013764 fipronil Drugs 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 206010004194 Bed bug infestation Diseases 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241000490513 Ctenocephalides canis Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241001481695 Dermanyssus gallinae Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000257232 Haematobia irritans Species 0.000 description 2
- 239000005912 Lufenuron Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000718000 Pulex irritans Species 0.000 description 2
- 241001481696 Rhipicephalus sanguineus Species 0.000 description 2
- 241000509427 Sarcoptes scabiei Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001494115 Stomoxys calcitrans Species 0.000 description 2
- 241001210412 Triatominae Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 244000078703 ectoparasite Species 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000036449 good health Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229960002418 ivermectin Drugs 0.000 description 2
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 2
- 229960000521 lufenuron Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
- RFEJUZJILGIRHQ-XRIOVQLTSA-N 2,3-dihydroxybutanedioic acid;3-[(2s)-1-methylpyrrolidin-2-yl]pyridine Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O.CN1CCC[C@H]1C1=CC=CN=C1 RFEJUZJILGIRHQ-XRIOVQLTSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001480748 Argas Species 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000322475 Bovicola Species 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 241001307956 Chorioptes bovis Species 0.000 description 1
- 241001124179 Chrysops Species 0.000 description 1
- 241000202814 Cochliomyia hominivorax Species 0.000 description 1
- 241000258922 Ctenocephalides Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000692095 Cuterebra Species 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 241000257324 Glossina <genus> Species 0.000 description 1
- 241001502121 Glossina brevipalpis Species 0.000 description 1
- 241000790933 Haematopinus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241001113970 Linognathus Species 0.000 description 1
- 241000692235 Lipoptena cervi Species 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 241000771994 Melophagus ovinus Species 0.000 description 1
- 241000035436 Menopon Species 0.000 description 1
- 241001481698 Mesostigmata Species 0.000 description 1
- 241000543819 Oestrus ovis Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001196585 Polyplax spinulosa Species 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241001649231 Psoroptidae Species 0.000 description 1
- 241001675082 Pulex Species 0.000 description 1
- AQXXZDYPVDOQEE-MXDQRGINSA-N Pyrantel pamoate Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 AQXXZDYPVDOQEE-MXDQRGINSA-N 0.000 description 1
- 241001481703 Rhipicephalus <genus> Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241000044136 Solenopotes Species 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241000255632 Tabanus atratus Species 0.000 description 1
- 241001414833 Triatoma Species 0.000 description 1
- 241000331598 Trombiculidae Species 0.000 description 1
- 241000353224 Xenopsylla Species 0.000 description 1
- 241000353223 Xenopsylla cheopis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000013057 ectoparasiticide Substances 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- ASLBZKNWGWVWSM-UHFFFAOYSA-N ethyl n-[5-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazol-3-yl]methanimidate Chemical compound CCOC=NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ASLBZKNWGWVWSM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960000996 pyrantel pamoate Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- 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
-
- 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11185798P | 1998-12-11 | 1998-12-11 | |
| US14068099P | 1999-06-24 | 1999-06-24 | |
| PCT/EP1999/010452 WO2000035884A1 (en) | 1998-12-11 | 1999-12-10 | Control of arthropods in animals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20012820D0 NO20012820D0 (no) | 2001-06-07 |
| NO20012820L NO20012820L (no) | 2001-08-13 |
| NO320018B1 true NO320018B1 (no) | 2005-10-10 |
Family
ID=26809313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20012820A NO320018B1 (no) | 1998-12-11 | 2001-06-07 | 1-arylpyrazolforbindelse, preparat inneholdende den samme samt anvendelse derav. |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6160002A (cs) |
| EP (1) | EP1137639B1 (cs) |
| JP (1) | JP4757385B2 (cs) |
| KR (2) | KR100859295B1 (cs) |
| CN (1) | CN1154638C (cs) |
| AP (1) | AP1603A (cs) |
| AR (1) | AR021608A1 (cs) |
| AT (1) | ATE440086T1 (cs) |
| AU (1) | AU770796B2 (cs) |
| BG (1) | BG65289B1 (cs) |
| BR (1) | BRPI9916967B8 (cs) |
| CA (1) | CA2355214C (cs) |
| CO (1) | CO5140086A1 (cs) |
| CU (1) | CU23113A3 (cs) |
| CZ (1) | CZ303314B6 (cs) |
| DE (1) | DE69941303D1 (cs) |
| EA (1) | EA004144B1 (cs) |
| EE (1) | EE05363B1 (cs) |
| ES (1) | ES2331672T3 (cs) |
| HK (1) | HK1042900B (cs) |
| HR (1) | HRP20010437B1 (cs) |
| HU (1) | HUP0104636A3 (cs) |
| ID (1) | ID30036A (cs) |
| IL (4) | IL143140A0 (cs) |
| MA (1) | MA25274A1 (cs) |
| NO (1) | NO320018B1 (cs) |
| NZ (1) | NZ511706A (cs) |
| OA (1) | OA11809A (cs) |
| PL (1) | PL352400A1 (cs) |
| SK (1) | SK287275B6 (cs) |
| WO (1) | WO2000035884A1 (cs) |
| YU (1) | YU39201A (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6531501B1 (en) | 1998-12-11 | 2003-03-11 | Aventis Cropscience, S.A. | Control of arthropods in animals |
| KR100784935B1 (ko) * | 2000-06-09 | 2007-12-17 | 메리얼 리미티드 | 살충 화합물의 제조 방법 |
| EP1223165A1 (en) * | 2001-01-16 | 2002-07-17 | Aventis Cropscience S.A. | Processes for the preparation of pesticidal compound |
| EP1286970B1 (en) * | 2000-06-09 | 2010-04-28 | Merial Limited | Processes for the preparation of pesticidal compounds and novel intermediates thereof |
| DK1483245T3 (da) * | 2002-03-05 | 2006-12-18 | Merial Ltd | 5-substituerede alkylaminopyrazolderivater som pesticider |
| US7517877B2 (en) | 2002-03-05 | 2009-04-14 | Merial Limited | 5-substituted-alkylaminopyrazole derivatives as pesticides |
| US20030215481A1 (en) * | 2002-05-09 | 2003-11-20 | Borchert Jeff N. | Control of ticks and fleas of rodents with systemic insecticides and insect growth regulators |
| GB0211924D0 (en) | 2002-05-23 | 2002-07-03 | Syngenta Ltd | Composition |
| EP1569517B1 (en) * | 2002-12-03 | 2013-10-02 | Merial Limited | Pesticidal 5- (acylamino) pyrazole derivatives |
| EA009293B1 (ru) | 2002-12-03 | 2007-12-28 | Байер Кропсайенс С. А. | Пестициды на основе сульфониламинопиразолов |
| MXPA06002380A (es) * | 2003-09-04 | 2006-06-20 | Bayer Cropscience Sa | Pesticidas. |
| BRPI0512578A (pt) | 2004-06-26 | 2008-03-25 | Bayer Cropscience Sa | derivados de n-fenilpirazol como pesticidas |
| JP5765371B2 (ja) * | 2013-06-14 | 2015-08-19 | 宇部興産株式会社 | ペンタフルオロスルファニル基を有する複素環オリゴマー化合物 |
| JP6779468B2 (ja) * | 2015-11-25 | 2020-11-04 | 宇部興産株式会社 | ペンタフルオロスルファニルピリジン |
| CN105503829A (zh) * | 2016-01-07 | 2016-04-20 | 河北蓝泰化工科技有限公司 | 一种氟虫腈-吡啶化合物及其制备方法和应用 |
| CN105712933B (zh) * | 2016-01-28 | 2019-01-11 | 中南民族大学 | 甲酰化芳基吡唑衍生物及其醚热合成方法和应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3719732A1 (de) * | 1987-06-12 | 1989-01-05 | Bayer Ag | Substituierte 5-methylamino-1-arylpyrazole |
| DE3724919A1 (de) * | 1987-07-28 | 1989-02-09 | Bayer Ag | 1-arylpyrazole |
| NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
| AU655014B2 (en) * | 1991-04-30 | 1994-12-01 | Merial Limited | Pesticidal 1-aryl-5-(substituted alkylideneimino)-pyrazoles |
| GB9120641D0 (en) * | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| US5556873A (en) * | 1993-02-24 | 1996-09-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles |
| GB9306184D0 (en) * | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| DE4343832A1 (de) * | 1993-12-22 | 1995-06-29 | Bayer Ag | Substituierte 1-Arylpyrazole |
| GB9601128D0 (en) * | 1995-08-11 | 1996-03-20 | Pfizer Ltd | Parasiticidal compounds |
| US5814652A (en) * | 1995-12-20 | 1998-09-29 | Rhone-Poulenc Inc. | Pesticidal 5-amino-4-ethylsulfinyl-1-arylpyrazoles |
| EP0811615A1 (en) * | 1996-06-03 | 1997-12-10 | Rhone-Poulenc Agrochimie | 1-Aryl-5-(substituted alkyl (thio) amido) pyrazoles and their use as pesticides |
| JP3735159B2 (ja) * | 1996-06-17 | 2006-01-18 | ローヌ−プーラン・アグロシミ | 新規な農薬 |
| GB9625045D0 (en) * | 1996-11-30 | 1997-01-22 | Pfizer Ltd | Parasiticidal compounds |
| TW524667B (en) * | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| AP1004A (en) * | 1996-12-24 | 2001-08-28 | Rhone Poulenc Agrochimie | Pesticidal 1-aryl and pyridylpyrazole derivatives. |
| CN1099415C (zh) * | 1996-12-24 | 2003-01-22 | 罗纳-普朗克农业化学公司 | 杀虫的1－芳基吡唑 |
| US6350771B1 (en) * | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
| ZA981776B (en) * | 1997-03-10 | 1998-09-03 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles |
| DE19824487A1 (de) * | 1998-06-02 | 1999-12-09 | Bayer Ag | Substituierte 3-Thiocarbamoylpyrazole |
-
1999
- 1999-12-09 AR ARP990106282A patent/AR021608A1/es active IP Right Grant
- 1999-12-10 NZ NZ511706A patent/NZ511706A/en not_active IP Right Cessation
- 1999-12-10 ID IDW00200101414A patent/ID30036A/id unknown
- 1999-12-10 HU HU0104636A patent/HUP0104636A3/hu unknown
- 1999-12-10 AT AT99964686T patent/ATE440086T1/de not_active IP Right Cessation
- 1999-12-10 CZ CZ20012030A patent/CZ303314B6/cs not_active IP Right Cessation
- 1999-12-10 KR KR1020077001923A patent/KR100859295B1/ko not_active Expired - Lifetime
- 1999-12-10 CA CA2355214A patent/CA2355214C/en not_active Expired - Lifetime
- 1999-12-10 US US09/457,869 patent/US6160002A/en not_active Expired - Lifetime
- 1999-12-10 AU AU30442/00A patent/AU770796B2/en not_active Expired
- 1999-12-10 IL IL14314099A patent/IL143140A0/xx active IP Right Grant
- 1999-12-10 EP EP99964686A patent/EP1137639B1/en not_active Expired - Lifetime
- 1999-12-10 HK HK02104424.6A patent/HK1042900B/zh not_active IP Right Cessation
- 1999-12-10 EA EA200100653A patent/EA004144B1/ru not_active IP Right Cessation
- 1999-12-10 BR BRPI9916967A patent/BRPI9916967B8/pt not_active IP Right Cessation
- 1999-12-10 EE EEP200100307A patent/EE05363B1/xx unknown
- 1999-12-10 HR HR20010437A patent/HRP20010437B1/xx not_active IP Right Cessation
- 1999-12-10 PL PL99352400A patent/PL352400A1/xx not_active Application Discontinuation
- 1999-12-10 OA OA1200100145A patent/OA11809A/en unknown
- 1999-12-10 SK SK790-2001A patent/SK287275B6/sk not_active IP Right Cessation
- 1999-12-10 DE DE69941303T patent/DE69941303D1/de not_active Expired - Lifetime
- 1999-12-10 WO PCT/EP1999/010452 patent/WO2000035884A1/en active Application Filing
- 1999-12-10 AP APAP/P/2001/002163A patent/AP1603A/en active
- 1999-12-10 CN CNB998142689A patent/CN1154638C/zh not_active Expired - Lifetime
- 1999-12-10 KR KR1020017007046A patent/KR100791407B1/ko not_active Expired - Lifetime
- 1999-12-10 JP JP2000588146A patent/JP4757385B2/ja not_active Expired - Lifetime
- 1999-12-10 ES ES99964686T patent/ES2331672T3/es not_active Expired - Lifetime
- 1999-12-11 YU YU39201A patent/YU39201A/sh unknown
- 1999-12-13 CO CO99077824A patent/CO5140086A1/es unknown
-
2001
- 2001-05-14 IL IL143140A patent/IL143140A/en not_active IP Right Cessation
- 2001-06-07 NO NO20012820A patent/NO320018B1/no not_active IP Right Cessation
- 2001-06-11 CU CU135A patent/CU23113A3/es unknown
- 2001-06-14 BG BG105603A patent/BG65289B1/bg unknown
- 2001-07-04 MA MA26258A patent/MA25274A1/fr unknown
-
2007
- 2007-07-09 IL IL184501A patent/IL184501A/en not_active IP Right Cessation
- 2007-07-09 IL IL184500A patent/IL184500A/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |