MX2011004217A - Compuestos de tioamida, metodo de elaboracion y metodo para usarlos. - Google Patents
Compuestos de tioamida, metodo de elaboracion y metodo para usarlos.Info
- Publication number
- MX2011004217A MX2011004217A MX2011004217A MX2011004217A MX2011004217A MX 2011004217 A MX2011004217 A MX 2011004217A MX 2011004217 A MX2011004217 A MX 2011004217A MX 2011004217 A MX2011004217 A MX 2011004217A MX 2011004217 A MX2011004217 A MX 2011004217A
- Authority
- MX
- Mexico
- Prior art keywords
- halo
- alkyl
- alkoxy
- alkylthio
- alkylsulfinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 150000003556 thioamides Chemical class 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title description 4
- 230000008569 process Effects 0.000 claims abstract description 12
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 186
- -1 Thioamide compound Chemical class 0.000 claims description 158
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical class 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 125000005110 aryl thio group Chemical group 0.000 claims description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- 241001465754 Metazoa Species 0.000 claims description 21
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 241000243974 Haemonchus contortus Species 0.000 claims description 5
- 244000000013 helminth Species 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
- 108010034145 Helminth Proteins Proteins 0.000 claims 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 105
- 238000002360 preparation method Methods 0.000 abstract description 14
- 239000000575 pesticide Substances 0.000 abstract description 8
- 238000009472 formulation Methods 0.000 description 47
- 239000003795 chemical substances by application Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 150000002148 esters Chemical class 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000011734 sodium Substances 0.000 description 23
- 229910052708 sodium Inorganic materials 0.000 description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- 229940083542 sodium Drugs 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 239000005660 Abamectin Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- 150000003839 salts Chemical group 0.000 description 12
- 235000015424 sodium Nutrition 0.000 description 12
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 239000002917 insecticide Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 10
- 239000004530 micro-emulsion Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 230000000361 pesticidal effect Effects 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 241000607479 Yersinia pestis Species 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 244000078703 ectoparasite Species 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 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 9
- 239000006072 paste Substances 0.000 description 9
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- 238000012360 testing method Methods 0.000 description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 9
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 8
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- 229910052799 carbon Inorganic materials 0.000 description 8
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- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
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- 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 8
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 125000004438 haloalkoxy group Chemical group 0.000 description 7
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 7
- 125000004995 haloalkylthio group Chemical group 0.000 description 7
- 239000003120 macrolide antibiotic agent Substances 0.000 description 7
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- 239000000463 material Substances 0.000 description 7
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- 241000238876 Acari Species 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
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- 241000282412 Homo Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
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- 229940045605 vanadium Drugs 0.000 description 1
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- 229960003165 vancomycin Drugs 0.000 description 1
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- 229960001722 verapamil Drugs 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
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- 229960002110 vincristine sulfate Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
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- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1
- 229960002911 zonisamide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Physiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10711408P | 2008-10-21 | 2008-10-21 | |
| PCT/US2009/061337 WO2010048191A1 (en) | 2008-10-21 | 2009-10-20 | Thioamide compounds, method of making and method of using thereof |
Publications (1)
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| MX2011004217A true MX2011004217A (es) | 2011-06-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| MX2011004217A MX2011004217A (es) | 2008-10-21 | 2009-10-20 | Compuestos de tioamida, metodo de elaboracion y metodo para usarlos. |
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| BR (1) | BRPI0920145B8 (enExample) |
| CA (1) | CA2741186C (enExample) |
| CL (1) | CL2011000917A1 (enExample) |
| EA (1) | EA026649B1 (enExample) |
| ES (1) | ES2393965T3 (enExample) |
| MX (1) | MX2011004217A (enExample) |
| NZ (1) | NZ592382A (enExample) |
| WO (1) | WO2010048191A1 (enExample) |
| ZA (1) | ZA201103033B (enExample) |
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| PH12018501647A1 (en) | 2011-09-12 | 2019-02-27 | Merial Inc | Parasiticidal compositions comprising an isoxazoline active agent, methods and uses thereof |
| SG11201404595TA (en) | 2012-02-06 | 2014-09-26 | Merial Ltd | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| NZ723198A (en) | 2012-11-20 | 2018-11-30 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic compounds and compositions and methods of using thereof |
| CN103073487B (zh) * | 2013-01-15 | 2014-11-19 | 西华大学 | N-双取代硫代乙酰胺类化合物的合成方法 |
| AR094961A1 (es) | 2013-03-15 | 2015-09-09 | Lilly Co Eli | 1-hidroxi-benzooxaboroles como agentes antiparasitarios |
| SG11201603430XA (en) | 2013-11-01 | 2016-05-30 | Merial Ltd | Antiparasitic and pesticidal isoxazoline compounds |
| CN104610110A (zh) * | 2014-03-12 | 2015-05-13 | 广东东阳光药业有限公司 | 一种制备4-取代硫代苯甲酰胺衍生物的方法 |
| ES2765405T3 (es) | 2014-04-17 | 2020-06-09 | Boehringer Ingelheim Animal Health Usa Inc | Utilización de compuestos de malononitrilo para proteger animales de parásitos |
| US10045979B2 (en) | 2014-05-19 | 2018-08-14 | Merial Inc. | Anthelmintic compounds |
| ES2887302T3 (es) | 2014-10-31 | 2021-12-22 | Boehringer Ingelheim Animal Health Usa Inc | Composiciones parasiticidas que comprenden fipronil |
| UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
| US10081656B2 (en) | 2015-05-20 | 2018-09-25 | Merial, Inc. | Anthelmintic depsipeptide compounds |
| UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| EP3525590B1 (en) | 2016-10-14 | 2025-08-20 | Boehringer Ingelheim Vetmedica GmbH | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| EP3541789A1 (en) | 2016-11-16 | 2019-09-25 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| CN111194316A (zh) | 2017-08-14 | 2020-05-22 | 勃林格殷格翰动物保健美国公司 | 农药的和杀寄生物的吡唑-异噁唑啉化合物 |
| IL279977B2 (en) | 2018-07-09 | 2024-06-01 | Boehringer Ingelheim Animal Health Usa Inc | Heterocyclic anthelmintic compounds |
| CN113260419A (zh) | 2018-11-20 | 2021-08-13 | 勃林格殷格翰动物保健美国公司 | 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 |
| KR102281492B1 (ko) * | 2018-12-24 | 2021-07-26 | 동인당제약 주식회사 | 세벨라머 함유 경구투여용 현탁제 조성물 및 그 제조방법 |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| MX2022015038A (es) | 2020-05-29 | 2023-01-04 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos como anthelminticos. |
| CN111781291A (zh) * | 2020-06-23 | 2020-10-16 | 广西壮族自治区水产科学研究院 | 一种水中13种大环内酯类抗生素的高分辨质谱检测方法 |
| WO2022140728A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animam Health Usa Inc. | Parasiticidal collar comprising isoxazoline compounds |
| WO2023156938A1 (en) | 2022-02-17 | 2023-08-24 | Boehringer Ingelheim Vetmedica Gmbh | Method and system for providing a fluid product mailer |
| CN117837424A (zh) * | 2024-02-04 | 2024-04-09 | 黄淮学院 | 一种控制农作物灰飞虱的方法 |
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| WO2006043654A1 (ja) | 2004-10-22 | 2006-04-27 | Nihon Nohyaku Co., Ltd. | アセトニトリル誘導体及び有害生物防除剤並びにその使用方法 |
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| EP2115927A1 (en) | 2007-02-05 | 2009-11-11 | Nokia Corporation | Method and apparatus for providing acknowledgment signaling |
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| EP2155699B9 (en) | 2007-05-15 | 2016-09-14 | Merial, Inc. | Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof |
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2009
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| US20100130565A1 (en) | 2010-05-27 |
| ES2393965T9 (es) | 2013-07-19 |
| EP2358687B1 (en) | 2012-09-19 |
| BRPI0920145B1 (pt) | 2021-03-30 |
| US8314146B2 (en) | 2012-11-20 |
| BRPI0920145B8 (pt) | 2021-05-25 |
| KR20170003704A (ko) | 2017-01-09 |
| CA2741186C (en) | 2016-07-19 |
| CA2741186A1 (en) | 2010-04-29 |
| ES2393965T3 (es) | 2013-01-03 |
| NZ592382A (en) | 2013-03-28 |
| EA026649B1 (ru) | 2017-05-31 |
| CL2011000917A1 (es) | 2011-09-16 |
| EP2358687A1 (en) | 2011-08-24 |
| AU2009307736A1 (en) | 2010-04-29 |
| KR101782311B1 (ko) | 2017-09-27 |
| ZA201103033B (en) | 2012-02-29 |
| CN102239151A (zh) | 2011-11-09 |
| EP2358687B9 (en) | 2013-04-17 |
| JP5614853B2 (ja) | 2014-10-29 |
| KR20110071140A (ko) | 2011-06-28 |
| AU2009307736B2 (en) | 2015-02-05 |
| US20110190231A1 (en) | 2011-08-04 |
| US7964621B2 (en) | 2011-06-21 |
| BRPI0920145A2 (pt) | 2017-06-06 |
| EA201100666A1 (ru) | 2011-12-30 |
| JP2012506441A (ja) | 2012-03-15 |
| WO2010048191A1 (en) | 2010-04-29 |
| KR101782308B1 (ko) | 2017-09-27 |
| CN102239151B (zh) | 2014-07-02 |
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