HRP970418A2 - Parasiticidal pyrazoles - Google Patents

Parasiticidal pyrazoles

Info

Publication number: HRP970418A2
Authority: HR; Croatia
Prior art keywords: optionally substituted; halogens; cyano; dichloro; compound
Prior art date: 1996-07-25

Application number

HR9704775.7A

Other languages

English (en)

Croatian (hr)

Inventor

Bernard Joseph Banks

Original Assignee

Bernard Joseph Banks

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.)

1996-07-25

Filing date

1997-07-24

Publication date

1998-08-31

1996-07-25 Priority claimed from GBGB9615660.9A external-priority patent/GB9615660D0/en

1997-07-24 Application filed by Bernard Joseph Banks filed Critical Bernard Joseph Banks

1998-08-31 Publication of HRP970418A2 publication Critical patent/HRP970418A2/hr

Links

230000000590 parasiticidal effect Effects 0.000 title claims description 9
150000003217 pyrazoles Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 156
239000000203 mixture Substances 0.000 claims description 85
229910052736 halogen Inorganic materials 0.000 claims description 68
150000002367 halogens Chemical class 0.000 claims description 68
150000003839 salts Chemical class 0.000 claims description 39
238000000034 method Methods 0.000 claims description 37
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
241000894007 species Species 0.000 claims description 16
-1 2,2,3,3-tetramethylcyclopropyl Chemical group 0.000 claims description 12
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 12
238000009472 formulation Methods 0.000 claims description 11
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
206010061217 Infestation Diseases 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
244000045947 parasite Species 0.000 claims description 7
LLNQWPTUJJYTTE-UHFFFAOYSA-N 4-iodopyrazole Chemical class IC=1C=NNC=1 LLNQWPTUJJYTTE-UHFFFAOYSA-N 0.000 claims description 6
230000003647 oxidation Effects 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
230000003071 parasitic effect Effects 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
XAHWAZBYPWNDJM-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(2,2,2-trifluoroacetyl)pyrazole-3-carbonitrile Chemical compound NC1=C(C(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XAHWAZBYPWNDJM-UHFFFAOYSA-N 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
DQGYLHNJMPWBPL-UHFFFAOYSA-N 4-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DQGYLHNJMPWBPL-UHFFFAOYSA-N 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
SRIGNWSMYMDBBR-UHFFFAOYSA-N 4-acetyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(=O)C)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SRIGNWSMYMDBBR-UHFFFAOYSA-N 0.000 claims description 3
ILKFYAOWLKDRLS-UHFFFAOYSA-N 4-formyl-1-phenylpyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C=O)=CN1C1=CC=CC=C1 ILKFYAOWLKDRLS-UHFFFAOYSA-N 0.000 claims description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
INCCXEDCEVKLSH-UHFFFAOYSA-N [Li]C1=CC=NN1 Chemical compound [Li]C1=CC=NN1 INCCXEDCEVKLSH-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
238000006138 lithiation reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims description 2
SETDRZRDBVXEDG-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(2-methylpropanoyl)pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(=O)C(C)C)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SETDRZRDBVXEDG-UHFFFAOYSA-N 0.000 claims description 2
XVMSEGBMJIILFH-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methylamino)-4-(2,2,2-trifluoroacetyl)pyrazole-3-carbonitrile Chemical compound CNC1=C(C(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XVMSEGBMJIILFH-UHFFFAOYSA-N 0.000 claims description 2
VWXTYHGCKKUWFF-UHFFFAOYSA-N 4-(cyclopropanecarbonyl)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=C(C#N)C(C(=O)C2CC2)=C1 VWXTYHGCKKUWFF-UHFFFAOYSA-N 0.000 claims description 2
DKPQFNLTNKJXRF-UHFFFAOYSA-N 4-acetyl-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(=O)C)=CN1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl DKPQFNLTNKJXRF-UHFFFAOYSA-N 0.000 claims description 2
JELJOVPTVKSDCD-UHFFFAOYSA-N 4-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(=O)C)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl JELJOVPTVKSDCD-UHFFFAOYSA-N 0.000 claims description 2
UMRPGBHVNGOFMG-UHFFFAOYSA-N 4-ethenyl-1h-pyrazole Chemical class C=CC=1C=NNC=1 UMRPGBHVNGOFMG-UHFFFAOYSA-N 0.000 claims description 2
LFZRBTITIPECIU-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(n-methoxy-c-methylcarbonimidoyl)pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(C)=NOC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl LFZRBTITIPECIU-UHFFFAOYSA-N 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
230000002147 killing effect Effects 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
239000012752 auxiliary agent Substances 0.000 claims 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims 1
125000005265 dialkylamine group Chemical group 0.000 claims 1
BAPZCSMFCUVUHW-UHFFFAOYSA-N dichloro(fluoro)methane Chemical compound F[C](Cl)Cl BAPZCSMFCUVUHW-UHFFFAOYSA-N 0.000 claims 1
230000036571 hydration Effects 0.000 claims 1
238000006703 hydration reaction Methods 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
238000007248 oxidative elimination reaction Methods 0.000 claims 1
125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
239000007787 solid Substances 0.000 description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 44
238000005481 NMR spectroscopy Methods 0.000 description 43
239000007921 spray Substances 0.000 description 41
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
239000012044 organic layer Substances 0.000 description 29
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 26
238000011176 pooling Methods 0.000 description 26
239000000741 silica gel Substances 0.000 description 25
229910002027 silica gel Inorganic materials 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
238000001704 evaporation Methods 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
241001465754 Metazoa Species 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 15
239000007832 Na2SO4 Substances 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
239000011259 mixed solution Substances 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
238000004440 column chromatography Methods 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
238000003756 stirring Methods 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
241000196324 Embryophyta Species 0.000 description 11
239000012267 brine Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 10
241000244206 Nematoda Species 0.000 description 9
241000607479 Yersinia pestis Species 0.000 description 9
230000006978 adaptation Effects 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
241000238421 Arthropoda Species 0.000 description 8
241000255925 Diptera Species 0.000 description 8
241000238631 Hexapoda Species 0.000 description 8
201000010099 disease Diseases 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
235000013399 edible fruits Nutrition 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 6
DDYLFCCPKXYTOI-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-iodopyrazole-3-carbonitrile Chemical compound NC1=C(I)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DDYLFCCPKXYTOI-UHFFFAOYSA-N 0.000 description 5
241000238876 Acari Species 0.000 description 5
241000256602 Isoptera Species 0.000 description 5
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 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
238000000746 purification Methods 0.000 description 5
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 5
241000282414 Homo sapiens Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 4
150000001299 aldehydes Chemical class 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
241000254173 Coleoptera Species 0.000 description 3
229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
241000254171 Curculionidae Species 0.000 description 3
241000223924 Eimeria Species 0.000 description 3
241000282412 Homo Species 0.000 description 3
235000002637 Nicotiana tabacum Nutrition 0.000 description 3
244000061176 Nicotiana tabacum Species 0.000 description 3
240000000111 Saccharum officinarum Species 0.000 description 3
235000007201 Saccharum officinarum Nutrition 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
238000010549 co-Evaporation Methods 0.000 description 3
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
230000000968 intestinal effect Effects 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
KADXVMRYQRCLAH-UHFFFAOYSA-N n'-iodobutanediamide Chemical compound NC(=O)CCC(=O)NI KADXVMRYQRCLAH-UHFFFAOYSA-N 0.000 description 3
239000012285 osmium tetroxide Substances 0.000 description 3
229910000489 osmium tetroxide Inorganic materials 0.000 description 3
244000144977 poultry Species 0.000 description 3
235000013594 poultry meat Nutrition 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 3
QLLWUQFHBKKOSR-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(2,2,2-trifluoroacetyl)pyrazole-3-carbonitrile Chemical compound N1=C(C#N)C(C(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLLWUQFHBKKOSR-UHFFFAOYSA-N 0.000 description 2
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230000002829 reductive effect Effects 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000005871 repellent Substances 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000028070 sporulation Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
GMMAPXRGRVJYJY-UHFFFAOYSA-J tetrasodium 4-acetamido-5-hydroxy-6-[[7-sulfonato-4-[(4-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].OC1=C2C(NC(=O)C)=CC=C(S([O-])(=O)=O)C2=CC(S([O-])(=O)=O)=C1N=NC(C1=CC(=CC=C11)S([O-])(=O)=O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 GMMAPXRGRVJYJY-UHFFFAOYSA-J 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
229940096911 trichinella spiralis Drugs 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000013598 vector Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pest Control & Pesticides (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Public Health (AREA)
Agronomy & Crop Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

HR9704775.7A 1996-07-25 1997-07-24 Parasiticidal pyrazoles HRP970418A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9615660.9A GB9615660D0 (en)	1996-07-25	1996-07-25	Parasiticidal compounds
GBGB9704775.7A GB9704775D0 (en)	1996-07-25	1997-03-07	Parasiticidal compounds

Publications (1)

Publication Number	Publication Date
HRP970418A2 true HRP970418A2 (en)	1998-08-31

Family

ID=26309761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR9704775.7A HRP970418A2 (en)	1996-07-25	1997-07-24	Parasiticidal pyrazoles

Country Status (15)

Country	Link
US (1)	US6028096A (de)
EP (1)	EP0918756B1 (de)
JP (1)	JP3432522B2 (de)
AP (1)	AP9701048A0 (de)
AT (1)	ATE260260T1 (de)
AU (1)	AU3552497A (de)
BR (1)	BR9710563A (de)
CA (1)	CA2260914C (de)
DE (1)	DE69727812T2 (de)
DK (1)	DK0918756T3 (de)
ES (1)	ES2215231T3 (de)
HR (1)	HRP970418A2 (de)
ID (1)	ID17666A (de)
PT (1)	PT918756E (de)
WO (1)	WO1998004530A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE295167T1 (de) *	1998-03-19	2005-05-15	Merck & Co Inc	Schwefelpentafluorophenylpyrazole zur kontrolle von ektoparasitenbefall
GB9810354D0 (en) *	1998-05-14	1998-07-15	Pfizer Ltd	Heterocycles
GB9916052D0 (en) *	1999-07-08	1999-09-08	Pfizer Ltd	Anthelmintic compositions
GB0413970D0 (en)	2004-06-22	2004-07-28	Syngenta Participations Ag	Chemical compounds
EP1893581B1 (de)	2005-06-15	2010-01-27	Pfizer Limited	Substituierte arylpyrazole zur verwendung gegen parasiten
US20080146643A1 (en) *	2005-06-15	2008-06-19	Pfizer Limited	Combination
US7645786B2 (en)	2005-06-15	2010-01-12	Pfizer Inc.	Substituted arylpyrazoles
US20080176865A1 (en) *	2005-06-15	2008-07-24	Pfizer Limited	Substituted arylpyrazoles
DE102006061537A1 (de)	2006-12-27	2008-07-03	Bayer Healthcare Ag	Mittel zur Bekämpfung von Parasiten an Tieren
DE102006061538A1 (de) *	2006-12-27	2008-07-03	Bayer Healthcare Ag	Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren
US9925167B2 (en)	2011-06-30	2018-03-27	Hansen-Ab Gmbh	Agents for the control of parasites on animals
JO3626B1 (ar)	2012-02-23	2020-08-27	Merial Inc	تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها
CN111116478B (zh) *	2019-12-18	2021-10-26	浙江金伯士药业有限公司	一种兽用抗生素维吉霉素中间体的制备方法
CN111072568B (zh) *	2019-12-26	2024-07-23	华东理工大学	含偶氮结构的苯基吡唑类化合物及其制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5232940A (en) *	1985-12-20	1993-08-03	Hatton Leslie R	Derivatives of N-phenylpyrazoles
DE3712204A1 (de) *	1987-04-10	1988-10-27	Bayer Ag	3-halogenalkyl-1-aryl-pyrazole
GB9120641D0 (en) *	1991-09-27	1991-11-06	Ici Plc	Heterocyclic compounds
DE19518054A1 (de) *	1995-03-08	1996-09-12	Hoechst Schering Agrevo Gmbh	N-Arylpyrazolketone und deren Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel

1997
- 1997-07-16 EP EP97931943A patent/EP0918756B1/de not_active Expired - Lifetime
- 1997-07-16 CA CA002260914A patent/CA2260914C/en not_active Expired - Fee Related
- 1997-07-16 US US09/230,200 patent/US6028096A/en not_active Expired - Fee Related
- 1997-07-16 PT PT97931943T patent/PT918756E/pt unknown
- 1997-07-16 AU AU35524/97A patent/AU3552497A/en not_active Abandoned
- 1997-07-16 BR BR9710563A patent/BR9710563A/pt not_active IP Right Cessation
- 1997-07-16 WO PCT/GB1997/001925 patent/WO1998004530A1/en not_active Ceased
- 1997-07-16 DK DK97931943T patent/DK0918756T3/da active
- 1997-07-16 AT AT97931943T patent/ATE260260T1/de not_active IP Right Cessation
- 1997-07-16 DE DE69727812T patent/DE69727812T2/de not_active Expired - Fee Related
- 1997-07-16 JP JP50858398A patent/JP3432522B2/ja not_active Expired - Fee Related
- 1997-07-16 ES ES97931943T patent/ES2215231T3/es not_active Expired - Lifetime
- 1997-07-24 ID IDP972564A patent/ID17666A/id unknown
- 1997-07-24 AP APAP/P/1997/001048A patent/AP9701048A0/en unknown
- 1997-07-24 HR HR9704775.7A patent/HRP970418A2/hr not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69727812D1 (de)	2004-04-01
CA2260914C (en)	2002-09-24
ES2215231T3 (es)	2004-10-01
DK0918756T3 (da)	2004-06-28
EP0918756A1 (de)	1999-06-02
PT918756E (pt)	2004-06-30
JP3432522B2 (ja)	2003-08-04
AP9701048A0 (en)	1997-07-31
JPH11514014A (ja)	1999-11-30
ID17666A (id)	1998-01-15
AU3552497A (en)	1998-02-20
ATE260260T1 (de)	2004-03-15
WO1998004530A1 (en)	1998-02-05
BR9710563A (pt)	1999-08-17
US6028096A (en)	2000-02-22
EP0918756B1 (de)	2004-02-25
CA2260914A1 (en)	1998-02-05
DE69727812T2 (de)	2004-08-05

Legal Events

Date	Code	Title	Description
1997-07-24	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1998-07-04	ODRP	Renewal fee for the maintenance of a patent	Payment date: 19980704 Year of fee payment: 2
1998-08-31	A1OB	Publication of a patent application
2005-02-16	ODBC	Application rejected

Publication	Publication Date	Title
DE3856585T2 (de)	2006-08-24	N-Phenylpyrazolderivate
CA2018704C (en)	2000-08-29	N-phenylpyrazole derivatives
DE3650042T2 (de)	1995-04-06	Pestizides Verfahren unter Verwendung von N-Phenylpyrazolen.
DE69709532T2 (de)	2002-10-31	1-Phenyl-Pyrazolderivate und ihr Verwendung als Schädlingsbekämpfungsmittel
AU710736B2 (en)	1999-09-30	Parasiticidal compounds
DE69627281T2 (de)	2003-11-13	Neue 1-Aryl Pyrazol Derivate und ihre Verwendung als Schädlingsbekämpfungsmittel
KR0160515B1 (ko)	1998-12-01	살충제로서의 n-페닐피라졸 유도체
EP0918756B1 (de)	2004-02-25	Parasitizide pyrazole
EP0295118A1 (de)	1988-12-14	N-Phenylpyrazol-Derivate
US5055482A (en)	1991-10-08	N-phenylpyrazol-4-yl ether derivatives
DE69013766T2 (de)	1995-04-06	N-Phenylpyrazol-Derivate.
DE69937771T2 (de)	2008-12-24	1-Aryl-4-cycloalk(en)ylpyrazole als antiparasitäre Mittel
US5177100A (en)	1993-01-05	N-phenylpyrazole derivatives
HK1021820A1 (en)	2000-07-07	Derivatives of n-phenylpyrazoles
HK1021820B (en)	2006-06-02	Derivatives of n-phenylpyrazoles
MXPA97009279A (en)	1999-04-27	Antiparasitici compounds
MXPA99004767A (en)	2000-02-02	Pirazo
IE84607B1 (en)	2007-06-13	Derivatives of N-Phenylpyrazoles
MXPA99006001A (en)	2000-02-02	Pesticidal 1-arylpyrazoles