WO2006127487A1 - Useful high load concentrate compositions for control of ecto-and endo-parasites - Google Patents
Useful high load concentrate compositions for control of ecto-and endo-parasites Download PDFInfo
- Publication number
- WO2006127487A1 WO2006127487A1 PCT/US2006/019513 US2006019513W WO2006127487A1 WO 2006127487 A1 WO2006127487 A1 WO 2006127487A1 US 2006019513 W US2006019513 W US 2006019513W WO 2006127487 A1 WO2006127487 A1 WO 2006127487A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- metaflumizone
- carrier solvent
- surfactant
- composition according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 239000012141 concentrate Substances 0.000 title abstract description 22
- 244000079386 endoparasite Species 0.000 title description 2
- 241001465754 Metazoa Species 0.000 claims abstract description 35
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 claims abstract description 32
- 239000005914 Metaflumizone Substances 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 239000004094 surface-active agent Substances 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 claims abstract description 18
- 229960004816 moxidectin Drugs 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000003120 macrolide antibiotic agent Substances 0.000 claims abstract description 13
- 230000002141 anti-parasite Effects 0.000 claims abstract description 10
- 239000003096 antiparasitic agent Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 239000007921 spray Substances 0.000 claims description 9
- 230000000149 penetrating effect Effects 0.000 claims description 8
- 206010061217 Infestation Diseases 0.000 claims description 7
- 239000004540 pour-on Substances 0.000 claims description 7
- 238000011200 topical administration Methods 0.000 claims description 5
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 4
- 239000005660 Abamectin Substances 0.000 claims description 4
- 241000282326 Felis catus Species 0.000 claims description 4
- 241001494479 Pecora Species 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 241000282898 Sus scrofa Species 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 2
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 2
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 2
- 241000283707 Capra Species 0.000 claims description 2
- 241000282994 Cervidae Species 0.000 claims description 2
- 241000283073 Equus caballus Species 0.000 claims description 2
- 229950008167 abamectin Drugs 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 229960002418 ivermectin Drugs 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 241000282836 Camelus dromedarius Species 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 30
- 230000000699 topical effect Effects 0.000 abstract description 4
- -1 moxidectin Chemical class 0.000 abstract description 3
- 206010014143 Ectoparasitic Infestations Diseases 0.000 abstract description 2
- 208000029380 parasitic ectoparasitic infectious disease Diseases 0.000 abstract 1
- 241000238421 Arthropoda Species 0.000 description 8
- 239000004544 spot-on Substances 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- 244000078703 ectoparasite Species 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 4
- 241000283086 Equidae Species 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 241000258242 Siphonaptera Species 0.000 description 4
- 239000008389 polyethoxylated castor oil Substances 0.000 description 4
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Chemical class COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000692095 Cuterebra Species 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 2
- 241001660203 Gasterophilus Species 0.000 description 2
- 208000006968 Helminthiasis Diseases 0.000 description 2
- 241000257176 Hypoderma <fly> Species 0.000 description 2
- 241000257162 Lucilia <blowfly> Species 0.000 description 2
- 241000920471 Lucilia caesar Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 229960005233 cineole Drugs 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 244000000013 helminth Species 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 1
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 description 1
- KRUABTDBQQLWLS-UHFFFAOYSA-N 1-methylsulfinyltetradecane Chemical compound CCCCCCCCCCCCCCS(C)=O KRUABTDBQQLWLS-UHFFFAOYSA-N 0.000 description 1
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
- 241001147657 Ancylostoma Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000282832 Camelidae Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 241001147667 Dictyocaulus Species 0.000 description 1
- 241000243990 Dirofilaria Species 0.000 description 1
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 108010034145 Helminth Proteins Proteins 0.000 description 1
- 241001608644 Hippoboscidae Species 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241000771994 Melophagus ovinus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 210000003165 abomasum Anatomy 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- RFFOTVCVTJUTAD-UHFFFAOYSA-N cineole Natural products C1CC2(C)CCC1(C(C)C)O2 RFFOTVCVTJUTAD-UHFFFAOYSA-N 0.000 description 1
- 229940000188 cydectin Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229960001673 diethyltoluamide Drugs 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229960003639 laurocapram Drugs 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- CKVMAPHTVCTEMM-ALPQRHTBSA-N milbemycin oxime Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\2)O)C[C@H]4C1.C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)C(=N/O)/[C@H]3OC\1)O)C[C@H]4C2 CKVMAPHTVCTEMM-ALPQRHTBSA-N 0.000 description 1
- 229940099245 milbemycin oxime Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Definitions
- Arthropod ectoparasites commonly infecting warm-blooded animals include ticks, mites, lice, fleas, blowfly, the ectoparasite Lucilia sp. of sheep, biting insects including keds (Melophagus ovinus) and migrating dipterous larvae such as
- Helminthiasis is a widespread disease found in many animals and is responsible for significant economic losses throughout the world. Among the helminths most frequently encountered are the group of worms referred to. as nematodes. The nematodes are found in the gastrointestinal tract, heart, lungs, blood vessels and other body tissues of animals and are a primary cause of anemia, weight loss and malnutrition in the infected animals. They do serious damage to the walls and tissue of the organs in which they reside and, if left untreated, may result in death to the infected animals.
- the nematodes most commonly found to be the infecting agents of ruminants include Haemonchus and Ostertagia generally found in the abomasum; Cooperia, Trichostrongylus and Nematodirus generally found in the intestinal tract, and Dictyocaulus found in the lungs.
- important nematodes include Toxocara and Ancylostoma in the intestine and Dirofilaria in the heart of dogs and cats; Ascaridae in the intestine of swine; and large and small strongyles in equines.
- Arthropod ectoparasites commonly infecting warm-blooded animals include ticks, mites, lice, fleas, blowfly, the ectoparasite Lucilia sp. of sheep, biting insects and migrating dipterous larvae such as Hypoderma sp. in cattle, Gastrophilus in horses and Cuterebra sp. in rodents.
- Anti-parasitic macrolide compounds such as LL-F28249 ⁇ - ⁇ compounds, 23- oxo or 23-imino derivatives of LL-F28249 ⁇ - ⁇ compounds, including, but not limited to, moxidectin, milbemycin compounds, including but not limited to milbemycin oxime, avermectin compounds, including, but not limited to abamectin, ivermectin, and mixtures thereof, are useful for the prevention and control of helminthiasis and infection by acarids and arthropod endo- and ectoparasites in warm-blooded animals.
- Metaflumizone is useful for the prevention and control of infestation by ectoparasites in warm-blooded animals. Topical administration of this active is a preferred method for administering this compound.
- Metaflumizone is one of several useful insecticidal agents which have found particular application for the control of fleas and ticks on animals, particularly companion animals such as dogs, cats and horses. It is particularly advantageous in that it can provide 4-6 weeks of protection from fleas and ticks in companion animals, but it would be potentially useful for many other species if suitable formulations could be developed. Nonetheless, formulation of metaflumizone is made difficult by its insolubility in many solvents, and its instability in the presence of primary alcohols.
- It is the object of the present invention to provide a method for preventing, controlling or treating helminth, acarid or arthropod endo- or ectoparasitic infection or infestation in warm-blooded animals which method comprises topically administering to the warm-blooded animals an anthelmintically, acaricidally or arthropod endo- or ectoparasiticidally effective amount of a nonaqueous composition which comprises about 0.1 to 10% w/v of a substantially water-insoluble anti-parasitic macrolide compound, about 5% to about 40% of metaflumizone; about 0% to about 15% of a bridging or penetrating agent; about 2 to 8% of a surfactant, and about 50 to 80% w/v of a pharmaceutically acceptable water-miscible or water immiscible solvent or solvent system as the carrier.
- the formulation can function as a concentrate, which with simple modifications, can be extended to use for a wide variety of other animals.
- the concentrated formulation can be utilized as a small volume spot-on formulation, for instance, for protection of companion animals, while further dilutions can be utilized as conventional pour-on products for farm animals, with still further dilutions utilizable for sprays and application to the feed.
- the present invention provides high-load concentrate compositions for topical administration which comprise on a weight to volume basis: about 0.1 to about 10% of substantially water-insoluble anti-parasitic macrolide compound, especially, moxidectin: about 5% to about 40% of metaflumizone; about 0% to about 15% of a bridging or penetrating agent; about 2 to about 8% of a surfactant and about 50% to about 80% of a carrier solvent.
- the present invention further provides a method for preventing or treating ectoparasitic and endoparasitic infection or infestation in a warm-blooded animal which method comprises topically administering to the animal an acaricidally or arthropod ectoparasiticidally effective amount of the composition of this invention.
- the high load concentrate compositions comprise a substantially water-insoluble anti-parasitic macrolide compound, especially, moxidectin, metaflumizone; an optional bridging agent or penetration enhancer, a surfactant, and a carrier solvent.
- the invention also provides a method for preventing or treating acarid or arthropod ectoparasitic infection or infestation in warm-blooded animals by topical application of the aforesaid formulations.
- Preferred high load concentrate compositions of this invention comprise on a weight to volume basis:
- a substantially water-insoluble anti-parasitic macrolide compound especially, moxidectin about 5% to about 40% of metaflumizone; about 0% to about 15% of a bridging or penetrating agent; about 2 to about 8% of a surfactant and about 50% to about 80% of a carrier solvent.
- compositions of the present invention have the requisite stability by virtue of physical and or chemical interactions between the surfactant and the metaflumizone.
- the exact nature of the interactions is unknown, but apparently the surfactant stabilizes the metaflumizone in solution so as to ensure that the resultant formulation retains the desired physical characteristics over time, without loss of potency of the active. Further, the formulation is sufficiently viscous to be retained upon the animal's skin, hair, and be released over the desired period of time.
- these high load concentrate compositions can be further utilized to prepare more dilute compositions for application in various other manners, i.e., for use as a pour-on for large animals, as a spray for large animals or for outdoor use, and as a water-dilutable formulation for addition to the feed and/or water supply of animals under treatment.
- This has the dual advantage of providing a concentrated formulation that can be shipped to the end-user for dilution and use, or to an intermediate formulator to prepare the compositions.
- the high loading of metaflumizone in the formulation thus provides a small volume of formulation to use as a "spot-on" formulation, for instance, for companion animals, especially felines.
- the concentrate can then be diluted by an appropriate organic solvent for use as a pour-on or in a spray, or with water, to provide the feed/water additive.
- metaflumizone is known as (E Z)-2-[2-(4-cyanophenyl)-1-[3- (trifluoromethyl)phenyl]ethylidene]- ⁇ /-[4-(trifluoromethoxy)phenyl] hydrazinecarboxamide.
- the substantially water-insoluble anti-parasitic macrolide compounds useful for the compositions of the present invention are well-know in the art, and are described in detail in, for instance, "Macrocyclic Lactones in Antiparasitic Therapy," edited by J. Vercruysse and R. S. Rew, CABI Publishing, London, 2002.
- Such macrolide compounds are subclassed into avermectins and milbemycins, with avermectins being glycosylated milbemycins.
- avermectins being glycosylated milbemycins.
- Bridging agents or penetrating agents or enhancers suitable for use in the compositions of this invention include, but are not limited to, alkyl methyl sulfoxides (such as dimethyl sulfoxide, decylmethyl sulfoxide and tetradecyl methyl sulfoxide); pyrrolidones (such as 2-pyrrolidone, N-methyl-2-pyrrolidone and N-(2-hydroxyethyl) pyrrolidone); laurocapram; and miscellaneous solvents such as acetone, dimethyl acetamide, dimethyl formamide, tetrahydrofurfuryl alcohol, cineole, N,N-diethyl-3- methylbenzamide (DEET), isopropyl myristate (IPM) and dimethyl isosorbide.
- Other bridging agents include amphiphiles such as L-amino acids, and fatty acids.
- the penetrating agent is used at a level of about 10% w/v of the formulation where the end use is for a topical application, but this may vary, especially when the end use of the composition is for oral administration.
- the surfactant utilized in the present invention may be a single surfactant, or a mixture of two or more surfactants, again, in part dependent upon whether the end use of the composition is topical or oral.
- the surfactant should be non-irritating, and non-toxic.
- non-ionic, low foaming surfactants such as the alcohol alkoxylate surfactants, with those such as nonylphenol ethoxylate (sold under the tradename Surfonic N-95), and alcohol alkoxylates (sold under the tradename Synperonic® NCA by Uniqema), and the polyethoxylated caster oil surfactants (also known as macrogolglycerol ricinoleate, and sold under the Cremaphore® EL tradename by BASF) being especially suitable.
- ionic surfactants such as sodium lauryl sulfate and dioctyl sodium sulfosuccinate.
- the surfactant is utilized at a level of about 2 to about 8% w/v of the composition, but this may vary somewhat depending upon the end use of the composition.
- the end use of the concentrate is as a spray formulation, or as a water-dispersible feed /water additive, it may be desirable to add a further surfactant to ensure that the diluted formulation will be a unitary phase.
- the additional surfactant may be added to the concentrate formulation, or added to the end use formulation with the diluting solvent.
- Particularly useful surfactants for use with an organic solvent diluent are non-ionic surfactants such as polyethoxylated castor oil, sold under the tradename Cremophor® EL by BASF Corporation.
- the carrier solvent for the compositions of the present invention may be a single solvent, or a mixture of solvents. Due to the instability of metaflumizone in the presence of primary alcohols, preferred solvents are non-hydroxyl-group-containing solvents, especially those such as ⁇ -hexalactone (gamma-hexalactone). Optionally, other such solvents such as N,N-diethyl-m-toluamide, eucalyptol, dimethyl isosorbide, diisopropyl adipate and/or methoxypropyl acetate (1-methoxy-2-propyl acetate) can be utilized in combination with the ⁇ -hexalactone to comprise the carrier solvent.
- solvents such as N,N-diethyl-m-toluamide, eucalyptol, dimethyl isosorbide, diisopropyl adipate and/or methoxypropyl acetate (1-methoxy-2-propyl acetate) can be
- the metaflumizone is dissolved in the carrier solvent or solvents, and the surfactant and bridging agent, if desired added to the mixture.
- This composition can then be utilized as a high load spot-on, or further diluted for additional uses.
- An especially preferred composition for topical administration to warm- blooded animals comprises, on a weight to volume basis, about 20% to about 30% metaflumizone; 0.5% moxidectin, about 10% of a bridging or penetrating agent, especially dimethyl sulfoxide, about 2 to-about 8%, and especially about 5%, of a non-ionic, low foam surfactant, and about 50-60% carrier solvent, especially ⁇ -hexalactone.
- the high load concentrate compositions of this invention may further comprise other agents known in the art, such as preservatives (e.g., methylparaben and propylparaben), colorants, antioxidants, and the like.
- compositions of this invention are highly effective for preventing or treating ectoparasitic infection and infestation for prolonged periods of time in warm-blooded animals such as cows, sheep, horses, camels, deer, swine, goats, dogs, cats, birds, and the like. Additionally, the composition is highly effective against endoparasitic infections.
- the following examples are presented primarily for the purpose of illustrating specific embodiments thereof. The invention is not to be deemed limited thereby, except as defined in the claims.
- DMSO dimethyl sulfoxide
- Example 2 To 25 ml of the high load concentrate prepared in Example 1 is added q.s. to 100 ml ⁇ -hexalactone. This provides a pour-on formulation having sufficient metaflumizone and moxidectin and volume to treat 5 head of cattle weighed 200 Kg each at 5 mg/kg dose rate metaflumizone and 0.25 mg/kg dose rate moxidectin.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002609212A CA2609212A1 (en) | 2005-05-24 | 2006-05-19 | Useful high load concentrate compositions for control of ecto-and endo-parasites |
AP2007094237A AP2007004237A0 (en) | 2005-05-24 | 2006-05-19 | Useful high load concentrate compositions for control of ecto- and endo-parasites |
AU2006251752A AU2006251752A1 (en) | 2005-05-24 | 2006-05-19 | Useful high load concentrate compositions for control of ecto-and endo-parasites |
BRPI0610143-7A BRPI0610143A2 (en) | 2005-05-24 | 2006-05-19 | composition for topical administration; and method for preventing or treating endoparasitic and ectoparasitic infection or infestation in warm-blooded animals |
MX2007014768A MX2007014768A (en) | 2005-05-24 | 2006-05-19 | Useful high load concentrate compositions for control of ecto-and endo-parasites. |
JP2008513562A JP2008542274A (en) | 2005-05-24 | 2006-05-19 | High-load concentrated composition useful for control of ectoparasites and endoparasites |
EA200702593A EA012041B1 (en) | 2005-05-24 | 2006-05-19 | High load concentrate compositions for control of ecto- and endo-parasites |
EP06770701A EP1890548A1 (en) | 2005-05-24 | 2006-05-19 | Useful high load concentrate compositions for control of ecto-and endo-parasites |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68395005P | 2005-05-24 | 2005-05-24 | |
US60/683,950 | 2005-05-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006127487A1 true WO2006127487A1 (en) | 2006-11-30 |
Family
ID=36954917
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2006/019513 WO2006127487A1 (en) | 2005-05-24 | 2006-05-19 | Useful high load concentrate compositions for control of ecto-and endo-parasites |
Country Status (14)
Country | Link |
---|---|
US (1) | US20060293260A1 (en) |
EP (1) | EP1890548A1 (en) |
JP (1) | JP2008542274A (en) |
KR (1) | KR20080029969A (en) |
CN (1) | CN101179939A (en) |
AP (1) | AP2007004237A0 (en) |
AR (1) | AR057319A1 (en) |
AU (1) | AU2006251752A1 (en) |
BR (1) | BRPI0610143A2 (en) |
CA (1) | CA2609212A1 (en) |
EA (1) | EA012041B1 (en) |
MX (1) | MX2007014768A (en) |
TW (1) | TW200718360A (en) |
WO (1) | WO2006127487A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008098168A2 (en) * | 2007-02-09 | 2008-08-14 | Wyeth | High-dose, long-acting ectoparasiticide for extended control |
WO2009035908A1 (en) * | 2007-09-11 | 2009-03-19 | Wyeth | Compositions and their use for the treatment of protozoal infections comprising metaflumi zone |
WO2010092014A2 (en) | 2009-02-11 | 2010-08-19 | Basf Se | Pesticidal mixtures |
WO2018167271A1 (en) * | 2017-03-17 | 2018-09-20 | Krka, D.D., Novo Mesto | Stable topical veterinary composition |
US10105323B2 (en) | 2008-06-06 | 2018-10-23 | Boehringer Ingelheim International Gmbh | Pharmaceutical dosage form for immediate release of an indolinone derivative |
EP2658542B1 (en) | 2010-12-27 | 2022-01-26 | Intervet International B.V. | Topical localized isoxazoline formulation |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100095900A1 (en) * | 2005-05-24 | 2010-04-22 | Wyeth Llc | Device and method for controlling insects |
DK2299987T3 (en) * | 2008-06-06 | 2018-05-22 | Boehringer Ingelheim Int | Pharmaceutical Capsule Dosage Form Containing A Suspension Formulation Of An Indolinone Derivative |
EP2331068B1 (en) * | 2008-10-08 | 2017-01-04 | Zoetis Services LLC | Benzimidazole anthelmintic compositions |
CN101564038B (en) * | 2009-04-23 | 2012-11-21 | 广东中迅农科股份有限公司 | Insecticidal composition containing metaflumizone |
UA108641C2 (en) | 2010-04-02 | 2015-05-25 | PARASITICID COMPOSITION CONTAINING FOUR ACTIVE AGENTS AND METHOD OF APPLICATION | |
TR201903499T4 (en) * | 2011-09-12 | 2019-04-22 | Merial Inc | PARASITIDAL COMPOSITIONS CONTAINING AN ISOXAZOLIN ACTIVE, THEIR METHODS AND USES |
WO2014132227A1 (en) * | 2013-02-27 | 2014-09-04 | Batt Laurie Robert | Transdermal formulations |
CN108294176A (en) * | 2017-12-29 | 2018-07-20 | 宣城市祥正生态农业发展有限公司 | A kind of ox cub feed addictive and application method |
KR20210082449A (en) * | 2018-10-24 | 2021-07-05 | 신젠타 파티서페이션즈 아게 | Novel Abamectin Soluble Concentrate Composition (SL) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1334661A1 (en) * | 2000-10-18 | 2003-08-13 | Nihon Nohyaku Co., Ltd. | Ectoparasitic insect pest controllers for animals and their usage |
EP1413201A2 (en) * | 2002-10-21 | 2004-04-28 | Wyeth | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
WO2004089239A2 (en) * | 2003-04-04 | 2004-10-21 | Merial Ltd. | Topical anthelmintic veterinary formulations |
WO2006042099A1 (en) * | 2004-10-08 | 2006-04-20 | Wyeth | Amitraz compositions |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69119301T2 (en) * | 1990-06-16 | 1996-10-17 | Nihon Nohyaku Co Ltd | Hydrazine carboxamide derivatives, process for their preparation and their use |
US20040122075A1 (en) * | 2002-12-16 | 2004-06-24 | Wyeth | N-phenyl-3-cyclopropylpyrazole-4-carbonitriles as ectoparasiticidal agents |
-
2006
- 2006-05-17 US US11/435,994 patent/US20060293260A1/en not_active Abandoned
- 2006-05-18 TW TW095117697A patent/TW200718360A/en unknown
- 2006-05-19 JP JP2008513562A patent/JP2008542274A/en not_active Withdrawn
- 2006-05-19 KR KR1020077030126A patent/KR20080029969A/en not_active Application Discontinuation
- 2006-05-19 WO PCT/US2006/019513 patent/WO2006127487A1/en active Application Filing
- 2006-05-19 BR BRPI0610143-7A patent/BRPI0610143A2/en not_active IP Right Cessation
- 2006-05-19 CN CNA2006800181316A patent/CN101179939A/en active Pending
- 2006-05-19 MX MX2007014768A patent/MX2007014768A/en unknown
- 2006-05-19 EA EA200702593A patent/EA012041B1/en not_active IP Right Cessation
- 2006-05-19 CA CA002609212A patent/CA2609212A1/en not_active Abandoned
- 2006-05-19 AP AP2007094237A patent/AP2007004237A0/en unknown
- 2006-05-19 EP EP06770701A patent/EP1890548A1/en not_active Withdrawn
- 2006-05-19 AU AU2006251752A patent/AU2006251752A1/en not_active Abandoned
- 2006-05-23 AR ARP060102130A patent/AR057319A1/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1334661A1 (en) * | 2000-10-18 | 2003-08-13 | Nihon Nohyaku Co., Ltd. | Ectoparasitic insect pest controllers for animals and their usage |
EP1413201A2 (en) * | 2002-10-21 | 2004-04-28 | Wyeth | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
WO2004089239A2 (en) * | 2003-04-04 | 2004-10-21 | Merial Ltd. | Topical anthelmintic veterinary formulations |
WO2006042099A1 (en) * | 2004-10-08 | 2006-04-20 | Wyeth | Amitraz compositions |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008098168A2 (en) * | 2007-02-09 | 2008-08-14 | Wyeth | High-dose, long-acting ectoparasiticide for extended control |
WO2008098168A3 (en) * | 2007-02-09 | 2009-05-22 | Wyeth Corp | High-dose, long-acting ectoparasiticide for extended control |
JP2010518118A (en) * | 2007-02-09 | 2010-05-27 | ワイス エルエルシー | High-dose long-acting ectoparasite control agent for long-term control |
WO2009035908A1 (en) * | 2007-09-11 | 2009-03-19 | Wyeth | Compositions and their use for the treatment of protozoal infections comprising metaflumi zone |
US10105323B2 (en) | 2008-06-06 | 2018-10-23 | Boehringer Ingelheim International Gmbh | Pharmaceutical dosage form for immediate release of an indolinone derivative |
WO2010092014A2 (en) | 2009-02-11 | 2010-08-19 | Basf Se | Pesticidal mixtures |
EP2658542B1 (en) | 2010-12-27 | 2022-01-26 | Intervet International B.V. | Topical localized isoxazoline formulation |
WO2018167271A1 (en) * | 2017-03-17 | 2018-09-20 | Krka, D.D., Novo Mesto | Stable topical veterinary composition |
Also Published As
Publication number | Publication date |
---|---|
BRPI0610143A2 (en) | 2010-06-01 |
JP2008542274A (en) | 2008-11-27 |
AU2006251752A1 (en) | 2006-11-30 |
CA2609212A1 (en) | 2006-11-30 |
TW200718360A (en) | 2007-05-16 |
AR057319A1 (en) | 2007-11-28 |
EA200702593A1 (en) | 2008-04-28 |
AP2007004237A0 (en) | 2007-12-31 |
US20060293260A1 (en) | 2006-12-28 |
EA012041B1 (en) | 2009-06-30 |
EP1890548A1 (en) | 2008-02-27 |
KR20080029969A (en) | 2008-04-03 |
CN101179939A (en) | 2008-05-14 |
MX2007014768A (en) | 2008-02-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20060293260A1 (en) | Useful high load concentrate compositions for control of ecto-and endo-parasites | |
EP1896000B1 (en) | Versatile high load concentrate compositions comprising metaflumizone for control of ecto-parasites | |
JP2010535231A (en) | Internal parasite control topical composition | |
NZ534704A (en) | Long acting parasiticidal composition containing a salicylanilide compound, a polymeric species and at least one other anti-parasitic compound | |
TWI418344B (en) | Stable non-aqueous pour-on compositions | |
US20060121072A1 (en) | Topical parasiticide formulations and methods of treatment | |
ES2290000T3 (en) | ANTIHELMINTIC COMPOSITIONS CONTAINING COMBINATIONS OF AVERMECTINES OR MILBEMICINES WITH BIS-ARILIC COMPOUNDS. | |
KR20080011224A (en) | Gel compositions for control of ecto-parasites | |
BR112015025875B1 (en) | STABLE INJECTABLE COMPOSITION FOR THE TREATMENT OF AN ENDOPARASITARY HELMINTH INFECTION IN NON-HUMAN ANIMALS, COMPOSITION FOR THE TREATMENT OF AN ENDOPARASITARY HELMINTH INFECTION OR INFESTATION IN A NON-HUMAN ANIMAL, AND THE USE OF DORAMECTIN OR A DORAMECTIN PHARMACEUTICALLY SALTY, | |
GB2386067A (en) | Long-acting parasiticidal composition with improved bioavailability comprising an avermectin or milbemycin, plus a salicylanilide & a polymeric species | |
EA009602B1 (en) | Antiparasiticidal composition | |
JP2966530B2 (en) | Pouring preparations effective for controlling in vivo and extracorporeal parasites of constant temperature animals and methods of using the same | |
AU2005336458B2 (en) | Anthelmintic formulations |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200680018131.6 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
ENP | Entry into the national phase |
Ref document number: 2609212 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 563556 Country of ref document: NZ Ref document number: 4474/KOLNP/2007 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 07123146 Country of ref document: CO Ref document number: 2006770701 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2008513562 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12007502638 Country of ref document: PH Ref document number: 2006251752 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/a/2007/014768 Country of ref document: MX |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200702593 Country of ref document: EA |
|
NENP | Non-entry into the national phase |
Ref country code: RU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020077030126 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref document number: PI0610143 Country of ref document: BR Kind code of ref document: A2 |