NO971766L - Anvendelsen av dioksomorfoliner for bekjempning av endoparasitter, nye dioksomorfoliner samt deres fremstilling - Google Patents
Anvendelsen av dioksomorfoliner for bekjempning av endoparasitter, nye dioksomorfoliner samt deres fremstillingInfo
- Publication number
- NO971766L NO971766L NO971766A NO971766A NO971766L NO 971766 L NO971766 L NO 971766L NO 971766 A NO971766 A NO 971766A NO 971766 A NO971766 A NO 971766A NO 971766 L NO971766 L NO 971766L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- residues
- spp
- compounds
- tert
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- MENOBBYDZHOWLE-UHFFFAOYSA-N morpholine-2,3-dione Chemical class O=C1NCCOC1=O MENOBBYDZHOWLE-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 244000079386 endoparasite Species 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 49
- 230000008569 process Effects 0.000 claims abstract description 13
- -1 alkali metal salt Chemical class 0.000 claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 24
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 12
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 12
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 12
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 12
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 12
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 12
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 108010002156 Depsipeptides Proteins 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000003978 alpha-halocarboxylic acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 13
- 239000003974 emollient agent Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 239000000243 solution Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 230000033228 biological regulation Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 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 description 6
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 210000004899 c-terminal region Anatomy 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000011814 protection agent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241000243974 Haemonchus contortus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical compound [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 235000019426 modified starch Nutrition 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XQZOGOCTPKFYKC-VSZULPIASA-N (2r)-n-[(3s,6s,8s,12s,13r,16s,17r,20s,23s)-13-[(2s)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]-4-methyl-2-(m Chemical compound C([C@H]1C(=O)O[C@H](C)[C@H](NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@@H]([C@H](CC(=O)O[C@H](C(=O)[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N2CCC[C@H]2C(=O)N1C)C(C)C)O)[C@@H](C)CC)C1=CC=C(OC)C=C1 XQZOGOCTPKFYKC-VSZULPIASA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Polymers FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 1
- LZILFXHGPBJADI-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;nonanoic acid Chemical compound CC(O)COC(C)CO.CCCCCCCCC(O)=O LZILFXHGPBJADI-UHFFFAOYSA-N 0.000 description 1
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- LBVZCSKDTGDAQW-UHFFFAOYSA-N 3-[(2-oxo-1,3-oxazolidin-3-yl)phosphanyl]-1,3-oxazolidin-2-one;hydrochloride Chemical compound [Cl-].O=C1OCCN1[PH2+]N1C(=O)OCC1 LBVZCSKDTGDAQW-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- XZQJHTXJNQNXIU-UHFFFAOYSA-N 6-benzyl-4-methyl-3-(2-methylpropyl)morpholine-2,5-dione Chemical compound O1C(=O)C(CC(C)C)N(C)C(=O)C1CC1=CC=CC=C1 XZQJHTXJNQNXIU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241001147657 Ancylostoma Species 0.000 description 1
- 241001626718 Anoplocephala Species 0.000 description 1
- 241000256837 Apidae Species 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241001448292 Austrobilharzia Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000999616 Avitellina Species 0.000 description 1
- 241001284802 Bertiella <tapeworm> Species 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241001323427 Bothridium Species 0.000 description 1
- 241001262976 Brachylaima Species 0.000 description 1
- 241000244036 Brugia Species 0.000 description 1
- 241000030939 Bubalus bubalis Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
- 241001126289 Calicophoron Species 0.000 description 1
- 241000282832 Camelidae Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000614965 Catatropis Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700112 Chinchilla Species 0.000 description 1
- 241001327942 Clonorchis Species 0.000 description 1
- 241000085576 Collyriclum Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 241000512048 Cotylophoron Species 0.000 description 1
- 241000986238 Crenosoma Species 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 241001133296 Cyathostoma Species 0.000 description 1
- 241000217886 Cyclocoelum Species 0.000 description 1
- 241000244152 Cyclophyllidea Species 0.000 description 1
- 241001235115 Cylicostephanus Species 0.000 description 1
- 241000252233 Cyprinus carpio Species 0.000 description 1
- 241001513864 Cystocaulus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241001262815 Dactylogyrus Species 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- 241000577452 Dicrocoelium Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241001389925 Digenea <Rhodophyta> Species 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical class CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- 241001222688 Diorchis Species 0.000 description 1
- 241001137876 Diphyllobothrium Species 0.000 description 1
- 241001626447 Diplopylidium Species 0.000 description 1
- 241000217468 Diplostomum Species 0.000 description 1
- 241000935794 Dipylidium Species 0.000 description 1
- 241000243990 Dirofilaria Species 0.000 description 1
- XEUXVSVRYSKWPZ-UHFFFAOYSA-N Dolastatin 3 Natural products C1NC(=O)C(N=2)=CSC=2C(CCC(N)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C2CCCN2C(=O)C2=CSC1=N2 XEUXVSVRYSKWPZ-UHFFFAOYSA-N 0.000 description 1
- 235000003550 Dracunculus Nutrition 0.000 description 1
- 241000316827 Dracunculus <angiosperm> Species 0.000 description 1
- 241001271717 Echinochasmus Species 0.000 description 1
- 241000244160 Echinococcus Species 0.000 description 1
- 241000990156 Echinoparyphium Species 0.000 description 1
- 241001126301 Echinostoma Species 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241001439622 Elaphostrongylus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000578375 Enoplida Species 0.000 description 1
- 241000498256 Enterobius Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 241000144295 Eurytrema Species 0.000 description 1
- 241001126309 Fasciolopsis Species 0.000 description 1
- HMCCXLBXIJMERM-UHFFFAOYSA-N Febantel Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)COC)=CC(SC=2C=CC=CC=2)=C1 HMCCXLBXIJMERM-UHFFFAOYSA-N 0.000 description 1
- 241001652048 Fischoederius Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241001448191 Gigantobilharzia Species 0.000 description 1
- 241000284013 Gigantocotyle Species 0.000 description 1
- 241000866662 Gigantorhynchida Species 0.000 description 1
- 241000880292 Gnathostoma Species 0.000 description 1
- 241001167431 Gongylonema Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241001636403 Gyalocephalus Species 0.000 description 1
- 241001523601 Gyrodactylus Species 0.000 description 1
- 241000315566 Habronema Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241001491880 Heterophyes Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- CMBYOWLFQAFZCP-UHFFFAOYSA-N Hexyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCCC CMBYOWLFQAFZCP-UHFFFAOYSA-N 0.000 description 1
- 241001464082 Hydatigera Species 0.000 description 1
- 241000404582 Hymenolepis <angiosperm> Species 0.000 description 1
- 241001547406 Hyostrongylus Species 0.000 description 1
- 241000223816 Hypoderaeum Species 0.000 description 1
- 241001626440 Joyeuxiella Species 0.000 description 1
- 241000990101 Leucochloridium Species 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000360065 Ligula Species 0.000 description 1
- 241000244011 Litomosoides Species 0.000 description 1
- 241000866639 Macracanthorhynchus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001523499 Marshallagia Species 0.000 description 1
- 241000520690 Mesocestoides Species 0.000 description 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- 241000556230 Metastrongylus Species 0.000 description 1
- 241001549582 Metorchis Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000274183 Micromeria Species 0.000 description 1
- 241001137878 Moniezia Species 0.000 description 1
- 241000700601 Moniliformis Species 0.000 description 1
- 241001524040 Monogenea Species 0.000 description 1
- 241000986227 Muellerius Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 241001501625 Nanophyetus Species 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000216953 Notocotylus Species 0.000 description 1
- IERDPZTZIONHSM-UHFFFAOYSA-N O=C1OCCN1[ClH]P(=O)[ClH]N1C(OCC1)=O Chemical compound O=C1OCCN1[ClH]P(=O)[ClH]N1C(OCC1)=O IERDPZTZIONHSM-UHFFFAOYSA-N 0.000 description 1
- 241000520254 Oesophagodontus Species 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000863910 Ollulanus Species 0.000 description 1
- 241000242716 Opisthorchis Species 0.000 description 1
- 241001448188 Ornithobilharzia Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001221709 Oxyurida Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000648839 Parabronema Species 0.000 description 1
- 241001480233 Paragonimus Species 0.000 description 1
- 241000531596 Paramphistomum Species 0.000 description 1
- 241001234663 Paranoplocephala Species 0.000 description 1
- 241000244187 Parascaris Species 0.000 description 1
- 241001344126 Parelaphostrongylus Species 0.000 description 1
- 241000069686 Passalurus Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241001277123 Physaloptera Species 0.000 description 1
- 241001657532 Plagiorchis Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000331522 Polystoma Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000578525 Posthodiplostomum Species 0.000 description 1
- 241000522483 Poteriostomum Species 0.000 description 1
- 241000282330 Procyon lotor Species 0.000 description 1
- 241000408369 Prosthogonimus Species 0.000 description 1
- 241001617421 Protostrongylus Species 0.000 description 1
- 241001222576 Raillietina Species 0.000 description 1
- 241000283011 Rangifer Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 241000277331 Salmonidae Species 0.000 description 1
- 241001222586 Schistocephalus Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 241000203992 Spirometra Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241001617580 Stephanurus Species 0.000 description 1
- 241000843044 Stilesia Species 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001220316 Syngamus Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000244155 Taenia Species 0.000 description 1
- 241001477954 Thelazia Species 0.000 description 1
- 241000999614 Thysaniezia Species 0.000 description 1
- 241000607216 Toxascaris Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000869417 Trematodes Species 0.000 description 1
- 241000243774 Trichinella Species 0.000 description 1
- 241001448053 Trichobilharzia Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 241001489151 Trichuris Species 0.000 description 1
- 241000530048 Triodontophorus Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 241001116191 Troglotrema Species 0.000 description 1
- 241000244002 Wuchereria Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 238000003975 animal breeding Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229940022769 d- lactic acid Drugs 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 230000036576 dermal application Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 108010061297 didemnins Proteins 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- ATCVYMAKQRUVDS-OSAZLGQLSA-N dolastatin 3 Chemical compound C1NC(=O)C(N=2)=CSC=2[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)C)NC(=O)C2=CSC1=N2 ATCVYMAKQRUVDS-OSAZLGQLSA-N 0.000 description 1
- 108010027025 dolastatin 3 Proteins 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- XQZOGOCTPKFYKC-UHFFFAOYSA-N epididemnin A1 Natural products CN1C(=O)C2CCCN2C(=O)C(CC(C)C)NC(=O)C(C)C(=O)C(C(C)C)OC(=O)CC(O)C(C(C)CC)NC(=O)C(NC(=O)C(CC(C)C)NC)C(C)OC(=O)C1CC1=CC=C(OC)C=C1 XQZOGOCTPKFYKC-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229960005282 febantel Drugs 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- XUPOMLOPDVAPNA-UHFFFAOYSA-N fenestin A Natural products CCC(C)C1NC(=O)C2CCCN2C(=O)C3CCCN3C(=O)C(NC1=O)C(C)CC XUPOMLOPDVAPNA-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- KCXYZMFPZHYUFO-UHFFFAOYSA-N n-methyl-n-phosphanylmethanamine Chemical compound CN(C)P KCXYZMFPZHYUFO-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 229930015720 peptide alkaloid Natural products 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- FIRCLRMVJNSQDR-UHFFFAOYSA-N phosphanylformonitrile Chemical compound PC#N FIRCLRMVJNSQDR-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 239000004297 potassium metabisulphite Substances 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 229960002957 praziquantel Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- YSAUAVHXTIETRK-AATRIKPKSA-N pyrantel Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1 YSAUAVHXTIETRK-AATRIKPKSA-N 0.000 description 1
- 229960005134 pyrantel Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 108010060791 ulicyclamide Proteins 0.000 description 1
- QMJCCXDXQJABCW-UHFFFAOYSA-N ulicyclamide Chemical compound N1C(=O)C(N=2)=CSC=2C(C)NC(=O)C(N=2)=CSC=2C(C(C)CC)NC(=O)C(C(O2)C)N=C2C2CCCN2C(=O)C1CC1=CC=CC=C1 QMJCCXDXQJABCW-UHFFFAOYSA-N 0.000 description 1
- ABGWWXGWIGDCFQ-UHFFFAOYSA-N ulicyclamide Natural products N1C(=O)C(N=2)=CSC=2C(C)NC(=O)C2CCCN2C(=O)C(C(O2)C)N=C2C(N=2)=CSC=2C(C(C)CC)NC(=O)C1CC1=CC=CC=C1 ABGWWXGWIGDCFQ-UHFFFAOYSA-N 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
-
- 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
- A61P33/02—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4440193A DE4440193A1 (de) | 1994-11-10 | 1994-11-10 | Verwendung von Dioxomorpholinen zur Bekämpfung von Endoparasiten, neue Dioxomorpholine und Verfahren zur ihrer Herstellung |
PCT/EP1995/004255 WO1996015121A1 (de) | 1994-11-10 | 1995-10-30 | Verwendung von dioxomorpholinen zur bekämpfung von endoparasiten, neue dioxomorpholine und verfahren zu ihrer herstellung |
Publications (2)
Publication Number | Publication Date |
---|---|
NO971766D0 NO971766D0 (no) | 1997-04-17 |
NO971766L true NO971766L (no) | 1997-04-17 |
Family
ID=6532993
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO971766A NO971766L (no) | 1994-11-10 | 1997-04-17 | Anvendelsen av dioksomorfoliner for bekjempning av endoparasitter, nye dioksomorfoliner samt deres fremstilling |
Country Status (22)
Country | Link |
---|---|
US (1) | US5856324A (ja) |
EP (1) | EP0790988B1 (ja) |
JP (1) | JP4163746B2 (ja) |
CN (1) | CN1070481C (ja) |
AT (1) | ATE231134T1 (ja) |
AU (1) | AU697150B2 (ja) |
BR (1) | BR9509708B1 (ja) |
CA (1) | CA2204748C (ja) |
CZ (1) | CZ125697A3 (ja) |
DE (2) | DE4440193A1 (ja) |
DK (1) | DK0790988T3 (ja) |
ES (1) | ES2190458T3 (ja) |
FI (1) | FI971967A (ja) |
HU (1) | HUT77132A (ja) |
IL (1) | IL115903A (ja) |
MX (1) | MX9703430A (ja) |
NO (1) | NO971766L (ja) |
NZ (1) | NZ295173A (ja) |
PL (1) | PL320064A1 (ja) |
SK (1) | SK58297A3 (ja) |
WO (1) | WO1996015121A1 (ja) |
ZA (1) | ZA959516B (ja) |
Families Citing this family (158)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6221894B1 (en) | 1995-03-20 | 2001-04-24 | Merck & Co., Inc. | Nodulisporic acid derivatives |
US6136838A (en) * | 1998-03-19 | 2000-10-24 | Merck & Co., Inc. | Sulfurpentafluorophenylpyrazoles for controlling ectoparasitic infestations |
EP1229934B1 (en) | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
CN1448393A (zh) * | 2002-03-28 | 2003-10-15 | 拜尔公司 | 抗内寄生物用的新型二氧代吗啉 |
AU2005223483B2 (en) | 2004-03-18 | 2009-04-23 | Zoetis Llc | N-(1-arylpyrazol-4l)sulfonamides and their use as parasiticides |
FR2896502B1 (fr) * | 2006-01-25 | 2010-09-24 | Scras | Nouvelle methode de synthese de 1,4-morpholine-2,5-diones |
TWI487486B (zh) | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
US8754053B2 (en) | 2010-02-17 | 2014-06-17 | Syngenta Crop Protection Llc | Isoxazoline derivatives as insecticides |
KR20130034011A (ko) | 2010-02-22 | 2013-04-04 | 신젠타 파티서페이션즈 아게 | 살곤충 화합물로서의 디하이드로푸란 유도체 |
CN102822168B (zh) | 2010-02-25 | 2016-10-26 | 先正达参股股份有限公司 | 制备异恶唑啉衍生物的方法 |
US8957058B2 (en) | 2010-10-05 | 2015-02-17 | Syngenta Participations Ag | Insecticidal pyrrolidin-yl-aryl-carboxamides |
WO2012049327A2 (en) | 2010-10-15 | 2012-04-19 | Syngenta Participations Ag | Pesticidal mixtures |
WO2012069366A1 (en) | 2010-11-23 | 2012-05-31 | Syngenta Participations Ag | Insecticidal compounds |
WO2012080376A1 (en) | 2010-12-17 | 2012-06-21 | Syngenta Participations Ag | Insecticidal compounds |
BR112013020213A2 (pt) | 2011-02-09 | 2016-08-02 | Syngenta Participations Ag | compostos inseticidas |
WO2012126881A1 (en) | 2011-03-22 | 2012-09-27 | Syngenta Participations Ag | Insecticidal compounds |
AU2012257690A1 (en) | 2011-05-18 | 2013-11-21 | Syngenta Participations Ag | Insecticidal compounds based on arylthioacetamide derivatives |
TW201311677A (zh) | 2011-05-31 | 2013-03-16 | Syngenta Participations Ag | 殺蟲化合物 |
WO2012163948A1 (en) | 2011-05-31 | 2012-12-06 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
WO2012175474A1 (en) | 2011-06-20 | 2012-12-27 | Syngenta Participations Ag | 1,2,3 triazole pesticides |
CN103732567A (zh) | 2011-08-22 | 2014-04-16 | 先正达参股股份有限公司 | 作为杀虫化合物的二氢呋喃衍生物 |
US20140343049A1 (en) | 2011-08-22 | 2014-11-20 | Syngenta Participations Ag | Dihydrofuran derivatives as insecticidal compounds |
CN103764644A (zh) | 2011-08-25 | 2014-04-30 | 先正达参股股份有限公司 | 作为杀虫化合物的异噁唑啉衍生物 |
US9204648B2 (en) | 2011-08-25 | 2015-12-08 | Syngenta Participations Ag | Process for the preparation of thietane derivatives |
WO2013026929A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Dihydropyrrole derivatives as insecticidal compounds |
CN103781356A (zh) | 2011-08-25 | 2014-05-07 | 先正达参股股份有限公司 | 作为杀虫化合物的异噁唑啉衍生物 |
WO2013026695A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
EP3190110B1 (en) | 2011-09-13 | 2020-01-08 | Syngenta Participations AG | Isothiazoline derivatives as insecticidal compounds |
JP2014534182A (ja) | 2011-10-03 | 2014-12-18 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫化合物としてのイソオキサゾリン誘導体 |
UA112556C2 (uk) | 2011-10-03 | 2016-09-26 | Сінгента Партісіпейшнс Аг | Інсектицидні похідні 2-метоксибензамідів |
US8962681B2 (en) | 2011-10-19 | 2015-02-24 | Zoetis Llc | Use of aminoacetonitrile derivatives against endoparasites |
WO2013135674A1 (en) | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
WO2014001121A1 (en) | 2012-06-25 | 2014-01-03 | Syngenta Participations Ag | Isothiazole derivatives as insecticidal compounds |
WO2014001120A1 (en) | 2012-06-25 | 2014-01-03 | Syngenta Participations Ag | Isothiazole derivatives as insecticidal compounds |
CN104755457A (zh) | 2012-10-31 | 2015-07-01 | 先正达参股股份有限公司 | 杀虫化合物 |
WO2014079935A1 (en) | 2012-11-21 | 2014-05-30 | Syngenta Participations Ag | Insecticidal compounds based on arylthioacetamide derivatives |
BR112015025028B1 (pt) | 2013-04-02 | 2020-10-13 | Syngenta Participations Ag | compostos, processo para a produção de compostos, métodos para controle de insetos, ácaros, nematódeos ou moluscos e para proteção de plantas úteis e composição |
JP6505080B2 (ja) | 2013-04-02 | 2019-04-24 | シンジェンタ パーティシペーションズ アーゲー | 殺虫性化合物 |
WO2015007451A1 (en) | 2013-07-15 | 2015-01-22 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives |
WO2015097091A1 (en) | 2013-12-23 | 2015-07-02 | Syngenta Participations Ag | Insecticidal compounds |
WO2016087593A1 (en) | 2014-12-05 | 2016-06-09 | Syngenta Participations Ag | Novel fungicidal quinolinylamidines |
EP3848364A1 (en) | 2015-03-27 | 2021-07-14 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives and intermediates for their preparation |
WO2016155831A1 (en) | 2015-04-02 | 2016-10-06 | Syngenta Participations Ag | Isoxazoline-styrene derivatives as insecticidal compounds |
WO2017055473A1 (en) | 2015-10-02 | 2017-04-06 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
CN108347936B (zh) | 2015-10-28 | 2021-04-20 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
US10357035B2 (en) | 2015-11-04 | 2019-07-23 | Syngenta Participations Ag | Microbiocidal anilide derivatives |
US10640497B2 (en) | 2015-12-02 | 2020-05-05 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
JP2019504010A (ja) | 2015-12-17 | 2019-02-14 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
BR112018068358A2 (pt) | 2016-03-15 | 2019-01-15 | Syngenta Participations Ag | derivados de oxadiazol microbiocidas |
US11083196B2 (en) | 2016-03-24 | 2021-08-10 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
JP2019514860A (ja) | 2016-04-08 | 2019-06-06 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性オキサジアゾール誘導体 |
US20190345150A1 (en) | 2016-04-12 | 2019-11-14 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2017178408A1 (en) | 2016-04-15 | 2017-10-19 | Syngenta Participations Ag | Microbiocidal silicon containing aryl derivatives |
ES2842550T3 (es) | 2016-05-30 | 2021-07-14 | Syngenta Participations Ag | Derivados de tiazol microbiocidas |
EP3464251B1 (en) | 2016-06-03 | 2021-03-03 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
AR108745A1 (es) | 2016-06-21 | 2018-09-19 | Syngenta Participations Ag | Derivados de oxadiazol microbiocidas |
US20190284148A1 (en) | 2016-07-22 | 2019-09-19 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
BR112019001226B1 (pt) | 2016-07-22 | 2022-11-29 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocida, composições agroquímicas compreendendo os referidos compostos, seus usos e método para controlar ou prevenir a infestação de plantas por micro-organismos fitopatogênicos |
JP2019528252A (ja) | 2016-07-22 | 2019-10-10 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
WO2018029242A1 (en) | 2016-08-11 | 2018-02-15 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018055135A1 (en) | 2016-09-23 | 2018-03-29 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018055133A1 (en) | 2016-09-23 | 2018-03-29 | Syngenta Participations Ag | Microbiocidal tetrazolone derivatives |
US10653146B2 (en) | 2016-10-06 | 2020-05-19 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
UY37623A (es) | 2017-03-03 | 2018-09-28 | Syngenta Participations Ag | Derivados de oxadiazol tiofeno fungicidas |
EP3592738A1 (en) | 2017-03-10 | 2020-01-15 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
CN110506040A (zh) | 2017-04-03 | 2019-11-26 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
WO2018184987A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018184984A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
BR112019020735B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas e seu uso, composição agroquímica e método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos |
BR112019020734B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso dos referidos compostos |
BR112019020739B1 (pt) | 2017-04-05 | 2023-12-19 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas e seu uso, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos |
BR112019020819B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Composto de fórmula (i), composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por micro-organismos fitopatogênicos e uso de um composto de fórmula (i) |
WO2018185211A1 (en) | 2017-04-06 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018206419A1 (en) | 2017-05-12 | 2018-11-15 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives |
CN110709395A (zh) | 2017-06-02 | 2020-01-17 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
BR112020000470A2 (pt) | 2017-07-11 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
WO2019011923A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
BR112020000457A2 (pt) | 2017-07-11 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
BR112020000456A2 (pt) | 2017-07-11 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
BR112020000371A2 (pt) | 2017-07-12 | 2020-07-14 | Syngenta Participations Ag | derivados de oxadiazol microbiocidas |
WO2019012001A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
BR112020000463A2 (pt) | 2017-07-13 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
WO2019053010A1 (en) | 2017-09-13 | 2019-03-21 | Syngenta Participations Ag | MICROBIOCIDE DERIVATIVES OF QUINOLINE (THIO) CARBOXAMIDE |
JP7330949B2 (ja) | 2017-09-13 | 2023-08-22 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
ES2904910T3 (es) | 2017-09-13 | 2022-04-06 | Syngenta Participations Ag | Derivados de quinolina (tio)carboxamida microbiocidas |
CN111093372B (zh) | 2017-09-13 | 2022-05-27 | 先正达参股股份有限公司 | 杀微生物的喹啉(硫代)羧酰胺衍生物 |
JP7158468B2 (ja) | 2017-09-13 | 2022-10-21 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
CN111094248A (zh) | 2017-09-13 | 2020-05-01 | 先正达参股股份有限公司 | 杀微生物的喹啉(硫代)羧酰胺衍生物 |
EP3681869B1 (en) | 2017-09-13 | 2021-12-08 | Syngenta Participations AG | Microbiocidal quinoline (thio)carboxamide derivatives |
UY37912A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan grupos terminales heteroarilo o heteroariloxi |
UY37913A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan un grupo terminal cuaternario |
BR112020009659A2 (pt) | 2017-11-15 | 2020-11-10 | Syngenta Participations Ag | derivados picolinamida microbiocidas |
BR112020009984A2 (pt) | 2017-11-20 | 2020-11-03 | Syngenta Participations Ag | derivados de oxadiazol microbicidas |
JP7241751B2 (ja) | 2017-11-29 | 2023-03-17 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物チアゾール誘導体 |
CN111566087A (zh) | 2017-12-19 | 2020-08-21 | 先正达参股股份有限公司 | 杀微生物的吡啶甲酰胺衍生物 |
GB201721235D0 (en) | 2017-12-19 | 2018-01-31 | Syngenta Participations Ag | Polymorphs |
WO2019207062A1 (en) | 2018-04-26 | 2019-10-31 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
CN112154141A (zh) | 2018-05-25 | 2020-12-29 | 先正达参股股份有限公司 | 杀微生物的吡啶甲酰胺衍生物 |
EP3814339A1 (en) | 2018-06-29 | 2021-05-05 | Syngenta Crop Protection AG | Microbiocidal oxadiazole derivatives |
WO2020007658A1 (en) | 2018-07-02 | 2020-01-09 | Syngenta Crop Protection Ag | 3-(2-thienyl)-5-(trifluoromethyl)-1,2,4-oxadiazole derivatives as agrochemical fungicides |
WO2020016180A1 (en) | 2018-07-16 | 2020-01-23 | Syngenta Crop Protection Ag | Microbiocidal oxadiazole derivatives |
GB201812692D0 (en) | 2018-08-03 | 2018-09-19 | Syngenta Participations Ag | Microbiocidal compounds |
ES2935972T3 (es) | 2018-09-19 | 2023-03-13 | Syngenta Crop Protection Ag | Derivados de quinolina carboxamida microbiocidas |
JP2022504304A (ja) | 2018-10-06 | 2022-01-13 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリンジヒドロ-(チアジン)オキサジン誘導体 |
WO2020070132A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
WO2020078732A1 (en) | 2018-10-17 | 2020-04-23 | Syngenta Crop Protection Ag | Microbiocidal oxadiazole derivatives |
AR116628A1 (es) | 2018-10-18 | 2021-05-26 | Syngenta Crop Protection Ag | Compuestos microbiocidas |
AR117200A1 (es) | 2018-11-30 | 2021-07-21 | Syngenta Participations Ag | Derivados de tiazol microbiocidas |
AR117183A1 (es) | 2018-11-30 | 2021-07-14 | Syngenta Crop Protection Ag | Derivados de tiazol microbiocidas |
WO2020165403A1 (en) | 2019-02-15 | 2020-08-20 | Syngenta Crop Protection Ag | Phenyl substituted thiazole derivatives as microbiocidal compounds |
GB201903942D0 (en) | 2019-03-22 | 2019-05-08 | Syngenta Crop Protection Ag | Microbiocidal compounds |
WO2020193618A1 (en) | 2019-03-27 | 2020-10-01 | Syngenta Crop Protection Ag | Microbiocidal thiazole derivatives |
WO2020208095A1 (en) | 2019-04-10 | 2020-10-15 | Syngenta Crop Protection Ag | Microbiocidal picolinamide derivatives |
US20230192628A1 (en) | 2019-05-29 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal derivatives |
AR119009A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | Derivados de alcoxipiridina y alcoxipirimidina microbicidas |
AR119011A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | DERIVADOS DE [1,3]DIOXOLO[4,5-c]PIRIDIN-4-CARBOXAMIDA, COMPOSICIONES AGROQUÍMICAS QUE LOS COMPRENDEN Y SU EMPLEO COMO FUNGICIDA PARA CONTROLAR O PREVENIR LA INFESTACIÓN DE PLANTAS ÚTILES |
US20220227763A1 (en) | 2019-05-29 | 2022-07-21 | Syngenta Crop Protection Ag | Microbiocidal derivatives |
JP2022535110A (ja) * | 2019-06-07 | 2022-08-04 | エランコ・ティアゲゾンタイト・アーゲー | 内部寄生虫を治療するための二環式誘導体 |
WO2021004968A1 (en) | 2019-07-05 | 2021-01-14 | Syngenta Crop Protection Ag | Microbiocidal picolinamide derivatives |
GB201910037D0 (en) | 2019-07-12 | 2019-08-28 | Syngenta Crop Protection Ag | Microbiocidal compounds |
AU2020333829A1 (en) | 2019-08-21 | 2022-03-03 | Syngenta Participations Ag | Precision treatment and sowing or planting method and device |
US20220279703A1 (en) | 2019-08-21 | 2022-09-08 | Syngenta Participations Ag | Apparatus and method for reducing dust development in precision drill sowing |
EP4017243A1 (en) | 2019-08-21 | 2022-06-29 | Syngenta Participations Ag | High precision greenhouse seed and seedling treatment |
EP4017245A1 (en) | 2019-08-21 | 2022-06-29 | Syngenta Participations Ag | Sowing device and method for treating seeds during planting |
CN114269145A (zh) | 2019-08-21 | 2022-04-01 | 先正达参股股份有限公司 | 用于转变现有的播种设备的器械和方法 |
BR112022020239A2 (pt) | 2020-04-08 | 2022-11-22 | Syngenta Crop Protection Ag | Derivados de quinolina di-hidro-(tiazina)oxazina microbiocidas |
AR121734A1 (es) | 2020-04-08 | 2022-07-06 | Syngenta Crop Protection Ag | Derivados microbicidas de tipo dihidropirrolopirazina de quinolina |
AR121733A1 (es) | 2020-04-08 | 2022-07-06 | Syngenta Crop Protection Ag | Derivados microbiocidas de tipo dihidro-(tiazina)oxazina de quinolina |
GB202006386D0 (en) | 2020-04-30 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal Compounds |
GB202006399D0 (en) | 2020-04-30 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
GB202006480D0 (en) | 2020-05-01 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
GB202006606D0 (en) | 2020-05-05 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
WO2021244952A1 (en) | 2020-06-03 | 2021-12-09 | Syngenta Crop Protection Ag | Microbiocidal derivatives |
GB202014840D0 (en) | 2020-09-21 | 2020-11-04 | Syngenta Crop Protection Ag | Microbiocidal compounds |
BR112023019532A2 (pt) | 2021-03-27 | 2023-10-31 | Syngenta Crop Protection Ag | Derivados de amida isonicotínicos microbicidas |
UY39696A (es) | 2021-03-31 | 2022-10-31 | Syngenta Crop Protection Ag | Derivados microbiocidas de quinolin/quinoxalin-benzotiazina como agentes fungicidas, en particular c |
EP4326710A1 (en) | 2021-04-20 | 2024-02-28 | Syngenta Crop Protection AG | Microbiocidal quinoline/quinoxaline isoquinoline derivatives |
AU2022323303A1 (en) | 2021-08-02 | 2024-02-01 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2023089049A2 (en) | 2021-11-19 | 2023-05-25 | Syngenta Crop Protection Ag | Microbiocidal isonicotinic amide derivatives |
WO2023094303A1 (en) | 2021-11-25 | 2023-06-01 | Syngenta Crop Protection Ag | Microbiocidal heterobiaryl amide derivatives |
WO2023094304A1 (en) | 2021-11-25 | 2023-06-01 | Syngenta Crop Protection Ag | Microbiocidal heterobiaryl amide derivatives |
AR127922A1 (es) | 2021-12-15 | 2024-03-13 | Syngenta Crop Protection Ag | Derivados heterocíclicos bicíclicos microbiocidas |
WO2023110871A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2023111215A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal pyridine-substituted benzothiazine derivatives |
WO2023118011A1 (en) | 2021-12-22 | 2023-06-29 | Syngenta Crop Protection Ag | Microbiocidal aza-heterobiaryl derivatives |
WO2023139166A1 (en) | 2022-01-19 | 2023-07-27 | Syngenta Crop Protection Ag | Methods for controlling plant pathogens |
WO2023148206A1 (en) | 2022-02-02 | 2023-08-10 | Syngenta Crop Protection Ag | Microbiocidal n-amide derivatives |
WO2023166067A1 (en) | 2022-03-02 | 2023-09-07 | Syngenta Crop Protection Ag | Microbiocidal pyridazinone amide derivatives |
WO2023247552A1 (en) | 2022-06-21 | 2023-12-28 | Syngenta Crop Protection Ag | Microbiocidal bicyclic heterocyclic carboxamide derivatives |
WO2024018016A1 (en) | 2022-07-21 | 2024-01-25 | Syngenta Crop Protection Ag | Crystalline forms of 1,2,4-oxadiazole fungicides |
WO2024068656A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068655A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068950A1 (en) | 2022-09-30 | 2024-04-04 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024068947A1 (en) | 2022-09-30 | 2024-04-04 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024089191A1 (en) | 2022-10-27 | 2024-05-02 | Syngenta Crop Protection Ag | Microbiocidal heterobicyclic dihydrooxadiazine derivatives |
WO2024100069A1 (en) | 2022-11-08 | 2024-05-16 | Syngenta Crop Protection Ag | Microbiocidal pyridine derivatives |
WO2024100115A1 (en) | 2022-11-09 | 2024-05-16 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024105104A1 (en) | 2022-11-16 | 2024-05-23 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2139484A1 (en) * | 1992-07-31 | 1994-02-17 | Charles E. Nakamura | Process for the preparation of 3-,6-substituted 2,5-morpholinediones |
DE4317457A1 (de) * | 1993-05-26 | 1994-12-01 | Bayer Ag | Octacyclodepsipeptide mit endoparasitizider Wirkung |
DE4317432A1 (de) * | 1993-05-26 | 1994-12-01 | Bayer Ag | Octacyclodepsipeptide mit endoparasitizider Wirkung |
-
1994
- 1994-11-10 DE DE4440193A patent/DE4440193A1/de not_active Withdrawn
-
1995
- 1995-10-30 HU HU9701938A patent/HUT77132A/hu unknown
- 1995-10-30 CA CA2204748A patent/CA2204748C/en not_active Expired - Lifetime
- 1995-10-30 EP EP95936571A patent/EP0790988B1/de not_active Expired - Lifetime
- 1995-10-30 AU AU38456/95A patent/AU697150B2/en not_active Expired
- 1995-10-30 PL PL95320064A patent/PL320064A1/xx unknown
- 1995-10-30 SK SK582-97A patent/SK58297A3/sk unknown
- 1995-10-30 DE DE59510533T patent/DE59510533D1/de not_active Expired - Lifetime
- 1995-10-30 BR BRPI9509708-2A patent/BR9509708B1/pt active IP Right Grant
- 1995-10-30 WO PCT/EP1995/004255 patent/WO1996015121A1/de not_active Application Discontinuation
- 1995-10-30 NZ NZ295173A patent/NZ295173A/en not_active IP Right Cessation
- 1995-10-30 AT AT95936571T patent/ATE231134T1/de active
- 1995-10-30 DK DK95936571T patent/DK0790988T3/da active
- 1995-10-30 MX MX9703430A patent/MX9703430A/es unknown
- 1995-10-30 JP JP51567596A patent/JP4163746B2/ja not_active Expired - Lifetime
- 1995-10-30 ES ES95936571T patent/ES2190458T3/es not_active Expired - Lifetime
- 1995-10-30 US US08/836,560 patent/US5856324A/en not_active Expired - Lifetime
- 1995-10-30 CZ CZ971256A patent/CZ125697A3/cs unknown
- 1995-10-30 CN CN95197117A patent/CN1070481C/zh not_active Expired - Lifetime
- 1995-11-07 IL IL11590395A patent/IL115903A/xx not_active IP Right Cessation
- 1995-11-09 ZA ZA959516A patent/ZA959516B/xx unknown
-
1997
- 1997-04-17 NO NO971766A patent/NO971766L/no not_active Application Discontinuation
- 1997-05-07 FI FI971967A patent/FI971967A/fi unknown
Also Published As
Publication number | Publication date |
---|---|
NZ295173A (en) | 1998-06-26 |
EP0790988A1 (de) | 1997-08-27 |
ATE231134T1 (de) | 2003-02-15 |
IL115903A0 (en) | 1996-01-31 |
IL115903A (en) | 2000-07-26 |
ZA959516B (en) | 1996-05-28 |
ES2190458T3 (es) | 2003-08-01 |
CN1070481C (zh) | 2001-09-05 |
DK0790988T3 (da) | 2003-05-05 |
DE59510533D1 (de) | 2003-02-20 |
CA2204748C (en) | 2010-08-03 |
MX9703430A (es) | 1997-07-31 |
FI971967A0 (fi) | 1997-05-07 |
DE4440193A1 (de) | 1996-05-15 |
JP4163746B2 (ja) | 2008-10-08 |
WO1996015121A1 (de) | 1996-05-23 |
HUT77132A (hu) | 1998-03-02 |
CN1171105A (zh) | 1998-01-21 |
BR9509708A (pt) | 1998-06-16 |
BR9509708B1 (pt) | 2010-08-10 |
PL320064A1 (en) | 1997-09-01 |
CZ125697A3 (en) | 1997-08-13 |
AU697150B2 (en) | 1998-10-01 |
NO971766D0 (no) | 1997-04-17 |
FI971967A (fi) | 1997-05-07 |
US5856324A (en) | 1999-01-05 |
SK58297A3 (en) | 1998-07-08 |
AU3845695A (en) | 1996-06-06 |
EP0790988B1 (de) | 2003-01-15 |
JPH10508613A (ja) | 1998-08-25 |
CA2204748A1 (en) | 1996-05-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5856324A (en) | Use of dioxomorpholines for combat endoparasites, dioxomorpholines and process for their production | |
US6369028B1 (en) | Octacyclodepsipeptides having an endoparasiticidal action | |
US5717063A (en) | Octacyclodepsipeptides having an endoparasiticidal action | |
EP0644883A1 (de) | Enniatine und enniatinderivate zur bekämpfung von endoparasiten | |
KR100359618B1 (ko) | 내부기생충구제제조성물 | |
US5663140A (en) | Use of cyclic depsipeptides having 12 ring atoms for combating endoparasites, new cyclic despipeptides having 12 ring atoms, and processes for their preparation | |
AU768910B2 (en) | Endoparasiticidal agents | |
US5525591A (en) | Endoparasiticidal compositions based on open-chain octadepsipeptides | |
US5571793A (en) | Endoparasiticidal compositions based on open-chain tetradepsipeptides | |
DE4341991A1 (de) | Endoparasitizide Mittel auf Basis von offenkettigen Hexadepsipeptiden |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FC2A | Withdrawal, rejection or dismissal of laid open patent application |