TW201713212A - 抗寄生蟲組合物 - Google Patents

抗寄生蟲組合物 Download PDF

Info

Publication number: TW201713212A
Authority: TW; Taiwan
Prior art keywords: alkyl; substituted; halogen; group; compound
Prior art date: 2015-04-30

Application number

TW105113218A

Other languages

English (en)

Chinese (zh)

Inventor

克麗斯汀娜梅騰斯

沃納哈勒恩巴斯

翰斯喬格施瓦茨

Original Assignee

拜耳動物保健有限公司

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2015-04-30

Filing date

2016-04-28

Publication date

2017-04-16

2016-04-28 Application filed by 拜耳動物保健有限公司 filed Critical 拜耳動物保健有限公司

2017-04-16 Publication of TW201713212A publication Critical patent/TW201713212A/zh

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239000003096 antiparasitic agent Substances 0.000 title abstract description 4
230000002141 anti-parasite Effects 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 382
241001465754 Metazoa Species 0.000 claims abstract description 25
244000078703 ectoparasite Species 0.000 claims abstract description 14
229910052721 tungsten Inorganic materials 0.000 claims abstract description 10
230000000507 anthelmentic effect Effects 0.000 claims abstract description 6
239000003904 antiprotozoal agent Substances 0.000 claims abstract description 6
-1 1-(cyano)cyclopropyl Chemical group 0.000 claims description 550
229910052757 nitrogen Inorganic materials 0.000 claims description 178
229910052736 halogen Inorganic materials 0.000 claims description 169
150000002367 halogens Chemical class 0.000 claims description 135
229910052739 hydrogen Inorganic materials 0.000 claims description 91
239000000203 mixture Substances 0.000 claims description 77
125000005842 heteroatom Chemical group 0.000 claims description 71
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 69
125000004432 carbon atom Chemical group C* 0.000 claims description 64
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 56
229910052799 carbon Inorganic materials 0.000 claims description 48
125000004093 cyano group Chemical group *C#N 0.000 claims description 48
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 46
229910052760 oxygen Inorganic materials 0.000 claims description 46
229910052717 sulfur Inorganic materials 0.000 claims description 43
238000002360 preparation method Methods 0.000 claims description 37
125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 34
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 28
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
229910052796 boron Inorganic materials 0.000 claims description 28
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 25
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 25
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 25
125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 23
125000003277 amino group Chemical group 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 15
125000004434 sulfur atom Chemical group 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
244000045947 parasite Species 0.000 claims description 11
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 10
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 6
150000001204 N-oxides Chemical class 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000000034 method Methods 0.000 abstract description 87
244000000013 helminth Species 0.000 abstract description 6
230000008569 process Effects 0.000 abstract description 5
229940124339 anthelmintic agent Drugs 0.000 abstract description 2
239000000921 anthelmintic agent Substances 0.000 abstract description 2
239000000460 chlorine Substances 0.000 description 133
229910052801 chlorine Inorganic materials 0.000 description 132
229910052731 fluorine Inorganic materials 0.000 description 119
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 115
239000011737 fluorine Substances 0.000 description 112
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 111
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 103
229910052794 bromium Inorganic materials 0.000 description 96
238000006243 chemical reaction Methods 0.000 description 87
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 81
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 74
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 73
125000005843 halogen group Chemical group 0.000 description 57
125000001424 substituent group Chemical group 0.000 description 54
125000000217 alkyl group Chemical group 0.000 description 49
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 47
239000007858 starting material Substances 0.000 description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 37
239000001257 hydrogen Substances 0.000 description 33
238000007796 conventional method Methods 0.000 description 32
229910052740 iodine Inorganic materials 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
150000002431 hydrogen Chemical class 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 26
125000001153 fluoro group Chemical group F* 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000000623 heterocyclic group Chemical group 0.000 description 24
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
125000004122 cyclic group Chemical group 0.000 description 22
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000011630 iodine Substances 0.000 description 20
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 20
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 19
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
239000004327 boric acid Substances 0.000 description 18
125000001246 bromo group Chemical group Br* 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
150000003839 salts Chemical class 0.000 description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000001309 chloro group Chemical group Cl* 0.000 description 15
239000000126 substance Substances 0.000 description 15
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
239000003208 petroleum Substances 0.000 description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 12
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 11
241001674044 Blattodea Species 0.000 description 11
241000255925 Diptera Species 0.000 description 11
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 11
125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 11
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 10
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 10
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
125000004430 oxygen atom Chemical group O* 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 9
DXKZEUUVPWJJCX-UHFFFAOYSA-N 9h-fluorene;hydrochloride Chemical compound Cl.C1=CC=C2CC3=CC=CC=C3C2=C1 DXKZEUUVPWJJCX-UHFFFAOYSA-N 0.000 description 9
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
239000004567 concrete Substances 0.000 description 9
150000008282 halocarbons Chemical class 0.000 description 9
229930195733 hydrocarbon Natural products 0.000 description 9
150000002430 hydrocarbons Chemical class 0.000 description 9
PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 9
239000013598 vector Substances 0.000 description 9
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 8
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 8
125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 8
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 8
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 8
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
238000009835 boiling Methods 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
239000003085 diluting agent Substances 0.000 description 8
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 8
238000010931 ester hydrolysis Methods 0.000 description 8
150000002576 ketones Chemical class 0.000 description 8
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 8
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 8
238000006467 substitution reaction Methods 0.000 description 8
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 8
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 8
239000008096 xylene Substances 0.000 description 8
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 7
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 7
125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 7
241000238876 Acari Species 0.000 description 7
241001481703 Rhipicephalus <genus> Species 0.000 description 7
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 7
230000036541 health Effects 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 7
125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 7
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 6
FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 6
125000006002 1,1-difluoroethyl group Chemical group 0.000 description 6
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
241001128004 Demodex Species 0.000 description 6
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
125000003636 chemical group Chemical group 0.000 description 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
230000002140 halogenating effect Effects 0.000 description 6
125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 6
238000005897 peptide coupling reaction Methods 0.000 description 6
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 6
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239000000341 volatile oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Chemical Kinetics & Catalysis (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW105113218A 2015-04-30 2016-04-28 抗寄生蟲組合物 TW201713212A (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP15165955		2015-04-30

Publications (1)

Publication Number	Publication Date
TW201713212A true TW201713212A (zh)	2017-04-16

Family

ID=53039318

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW105113218A TW201713212A (zh)	2015-04-30	2016-04-28	抗寄生蟲組合物

Country Status (4)

Country	Link
AR (1)	AR104398A1 (es)
TW (1)	TW201713212A (es)
UY (1)	UY36652A (es)
WO (1)	WO2016174052A1 (es)

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KR102419769B1 (ko)	2016-08-11	2022-07-13	아다미스 파마슈티칼스 코포레이션	약물 조성물
BR112019010341B1 (pt) *	2016-12-19	2022-12-06	Nippon Soda Co., Ltd	Composto, e, formulação para controle de organismos nocivos, formulação inseticida ou formulação acaricida, formulação para controle de ectoparasitas, e, formulação para controle de endoparasitas ou para expulsão de endoparasitas
EP4298908A3 (de)	2017-03-31	2024-03-20	Bayer Animal Health GmbH	Trizyklische carboxamide zur bekämpfung von arthropoden
AR112673A1 (es)	2017-08-11	2019-11-27	Syngenta Participations Ag	Derivados de pirazol activos como plaguicidas
AR112672A1 (es)	2017-08-11	2019-11-27	Syngenta Participations Ag	Derivados de tiofeno activos como plaguicidas
EP3720844A4 (en)	2017-12-08	2021-08-11	Adamis Pharmaceuticals Corporation	MEDICINAL COMPOSITIONS
JP2021524461A (ja)	2018-05-24	2021-09-13	バイエル・アクチエンゲゼルシヤフト	置換ｎ−アリールピラゾールの製造方法
JP2021524459A (ja)	2018-05-24	2021-09-13	バイエル・アクチエンゲゼルシヤフト	ハロゲン化ｎ−アリールピラゾールの製造方法
MX2020013827A (es)	2018-06-22	2021-03-25	Bayer Ag	Proceso de preparacion de compuestos triciclicos.
EP3586630A1 (en) *	2018-06-28	2020-01-01	Bayer AG	Active compound combinations having insecticidal/acaricidal properties
EP3590927A1 (en)	2018-07-05	2020-01-08	Bayer Animal Health GmbH	Novel compounds for controlling arthropods
WO2020093014A1 (en) *	2018-11-02	2020-05-07	Adamis Pharmaceuticals Corporation	Drug compositions
EP3886854A4 (en)	2018-11-30	2022-07-06	Nuvation Bio Inc.	Pyrrole and pyrazole compounds and methods of use thereof
JP7547340B2 (ja)	2018-12-20	2024-09-09	バイエル・アクチエンゲゼルシヤフト	置換アニリンの製造方法
WO2020164994A1 (en)	2019-02-13	2020-08-20	Syngenta Crop Protection Ag	Pesticidally active pyrazole derivatives
EP3771711A1 (en)	2019-07-29	2021-02-03	Bayer Animal Health GmbH	Pyrazole derivatives for controlling arthropods
BR112022023012A2 (pt)	2020-05-12	2022-12-20	Bayer Ag	(tio)amidas de triazina e pirimidina como compostos fungicidas
CN112219852A (zh) *	2020-10-20	2021-01-15	青岛滕润翔检测评价有限公司	一种含烟酰胺类化合物的杀虫组合物在防治金银花虫害中的用途
EP4001271A1 (en)	2020-11-12	2022-05-25	Bayer Aktiengesellschaft	Crystalline form of 2-chloro-n-cyclopropyl-5-[1-[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]pyrazol-4-yl]-n-methyl-pyridine-3-carboxamide
EP3943483A1 (de)	2021-05-26	2022-01-26	Bayer AG	Verfahren zur herstellung von substituierten anilinen
AR126264A1 (es) *	2021-07-06	2023-10-04	Sumitomo Chemical Co	Composición de control de plagas y método de control de plagas
CN117736196A (zh) *	2022-09-15	2024-03-22	顺毅股份有限公司	一种吡啶酰胺衍生物及其用途
CN115843812B (zh) *	2022-12-23	2024-08-06	青岛凯源祥化工有限公司	一种含螺甲螨酯的杀虫杀螨组合物及其用途
CN118452218A (zh) *	2023-05-26	2024-08-09	江西海阔利斯生物科技有限公司	一种农药组合物及其应用
CN119462599A (zh) *	2023-08-11	2025-02-18	顺毅股份有限公司	一种n-取代的苯基吡唑衍生物及其制备和应用
CN121627640A (zh) *	2024-08-29	2026-03-10	沈阳思钺科技有限公司	一种苯基吡唑类化合物及其用途
WO2026046224A1 (zh) *	2024-08-29	2026-03-05	沈阳思钺科技有限公司	一种苯基吡唑类化合物及其应用

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2016
- 2016-04-25 UY UY0001036652A patent/UY36652A/es not_active Application Discontinuation
- 2016-04-25 AR ARP160101158A patent/AR104398A1/es unknown
- 2016-04-27 WO PCT/EP2016/059337 patent/WO2016174052A1/en not_active Ceased
- 2016-04-28 TW TW105113218A patent/TW201713212A/zh unknown

Also Published As

Publication number	Publication date
AR104398A1 (es)	2017-07-19
UY36652A (es)	2016-11-30
WO2016174052A1 (en)	2016-11-03

Publication	Publication Date	Title
WO2016174052A1 (en)	2016-11-03	Antiparasitic combinations
WO2016174049A1 (en)	2016-11-03	Anti-parasitic combinations including halogen-substituted compounds
US12377085B2 (en)	2025-08-05	Prolonged ectoparasite-controlling agent for animal
CN109890793B (zh)	2022-11-18	新的抗蠕虫药喹啉-3-甲酰胺衍生物
TWI484912B (zh)	2015-05-21	新穎之經鹵素取代的化合物
TWI742067B (zh)	2021-10-11	新吡唑並嘧啶衍生物
CN106103414B (zh)	2019-07-16	用于节肢动物处理的取代的苯酰胺类
TWI813680B (zh)	2023-09-01	新穎喹啉衍生物
TWI865563B (zh)	2024-12-11	新穎異喹啉衍生物
BR112015018311B1 (pt)	2021-01-05	compostos derivados de pirazol substituídos por halogêneo como agentes de controle de pragas, composição farmacêutica e uso dos mesmos, processo para a preparação de composições de proteção de colheitas e método para o controle de pragas
KR20200020911A (ko)	2020-02-26	새로운 아자퀴놀린 유도체
EP2253617A1 (de)	2010-11-24	Halogen-substituierte Verbindungen als Pestizide
TW202005532A (zh)	2020-02-01	控制節肢動物的新穎化合物
TW201317212A (zh)	2013-05-01	環胺化合物及有害生物防除劑
CN105008349A (zh)	2015-10-28	新的卤素取代的化合物
AU2022344499A1 (en)	2024-03-21	New quinoline derivatives
EP4003963B1 (en)	2023-08-16	Pyrazole derivatives for controlling arthropods
HK1227029A1 (en)	2017-10-13	Substituted benzamides for the treatment of arthropods