ZA200605109B - Topical formulations comprising A 1-N-arylpyrazole derivative and a formamidine - Google Patents
Topical formulations comprising A 1-N-arylpyrazole derivative and a formamidine Download PDFInfo
- Publication number
- ZA200605109B ZA200605109B ZA200605109A ZA200605109A ZA200605109B ZA 200605109 B ZA200605109 B ZA 200605109B ZA 200605109 A ZA200605109 A ZA 200605109A ZA 200605109 A ZA200605109 A ZA 200605109A ZA 200605109 B ZA200605109 B ZA 200605109B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- haloalkyl
- parasitical
- hydrogen
- topical formulation
- Prior art date
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- 239000012049 topical pharmaceutical composition Substances 0.000 title claims description 18
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- -1 dimethylaecetamide Chemical compound 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 19
- 244000045947 parasite Species 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 241000238876 Acari Species 0.000 claims description 12
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical group C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 10
- 229960002587 amitraz Drugs 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 5
- 239000004540 pour-on Substances 0.000 claims description 5
- 239000004544 spot-on Substances 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical group NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 4
- 241000282326 Felis catus Species 0.000 claims description 4
- 239000005899 Fipronil Substances 0.000 claims description 4
- 230000000507 anthelmentic effect Effects 0.000 claims description 4
- 230000002141 anti-parasite Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229940013764 fipronil Drugs 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 239000003963 antioxidant agent Substances 0.000 claims 3
- 230000003078 antioxidant effect Effects 0.000 claims 3
- 235000006708 antioxidants Nutrition 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims 2
- 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 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 239000002280 amphoteric surfactant Substances 0.000 claims 2
- 239000003945 anionic surfactant Substances 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 239000002736 nonionic surfactant Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000003981 vehicle Substances 0.000 claims 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims 1
- 240000002791 Brassica napus Species 0.000 claims 1
- 125000006414 CCl Chemical group ClC* 0.000 claims 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 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 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 claims 1
- 241000283715 Damaliscus lunatus Species 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 1
- 101150034459 Parpbp gene Proteins 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 241001249696 Senna alexandrina Species 0.000 claims 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000004359 castor oil Substances 0.000 claims 1
- 235000019438 castor oil Nutrition 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000003093 cationic surfactant Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002191 fatty alcohols Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 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 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical class C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 1
- 229940100242 glycol stearate Drugs 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 239000003630 growth substance Substances 0.000 claims 1
- 125000004992 haloalkylamino group Chemical group 0.000 claims 1
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001145 hydrido group Chemical class *[H] 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000000787 lecithin Substances 0.000 claims 1
- 235000010445 lecithin Nutrition 0.000 claims 1
- 229940067606 lecithin Drugs 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N phthalic acid di-n-ethyl ester Natural products CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 1
- 229920000053 polysorbate 80 Polymers 0.000 claims 1
- 229940068968 polysorbate 80 Drugs 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002728 pyrethroid Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 229940020549 rayos Drugs 0.000 claims 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims 1
- 235000010262 sodium metabisulphite Nutrition 0.000 claims 1
- 239000004296 sodium metabisulphite Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 235000010356 sorbitol Nutrition 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 16
- 239000005660 Abamectin Substances 0.000 description 14
- 244000078703 ectoparasite Species 0.000 description 9
- 201000010099 disease Diseases 0.000 description 8
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- 208000015181 infectious disease Diseases 0.000 description 8
- 241000258242 Siphonaptera Species 0.000 description 7
- 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 7
- 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 description 6
- 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 description 6
- 229960002418 ivermectin Drugs 0.000 description 6
- 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 description 5
- 241001674048 Phthiraptera Species 0.000 description 5
- 229950008167 abamectin Drugs 0.000 description 5
- 239000003096 antiparasitic agent Substances 0.000 description 4
- 244000079386 endoparasite Species 0.000 description 4
- 150000002596 lactones Chemical group 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
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Classifications
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N47/02—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 no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
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| US53052503P | 2003-12-17 | 2003-12-17 | |
| US10/783,459 US7531186B2 (en) | 2003-12-17 | 2004-02-20 | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
| PCT/US2004/042379 WO2005058038A1 (en) | 2003-12-17 | 2004-12-17 | Topical formulations comprising a 1-n-arylpyrazole derivative and a formamidine |
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| ZA200605109B true ZA200605109B (en) | 2007-11-28 |
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| ZA200605109A ZA200605109B (en) | 2003-12-17 | 2006-06-21 | Topical formulations comprising A 1-N-arylpyrazole derivative and a formamidine |
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| JP (2) | JP4926719B2 (no) |
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| CN (1) | CN1905794B (no) |
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| BR (1) | BRPI0417209B1 (no) |
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| CR (2) | CR8464A (no) |
| ES (1) | ES2650713T3 (no) |
| IL (1) | IL176360A (no) |
| IN (1) | IN2012DN02432A (no) |
| NO (1) | NO336284B1 (no) |
| NZ (2) | NZ578628A (no) |
| OA (1) | OA13346A (no) |
| PL (2) | PL393289A1 (no) |
| RU (1) | RU2361401C2 (no) |
| WO (1) | WO2005058038A1 (no) |
| ZA (1) | ZA200605109B (no) |
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| US20060046988A1 (en) * | 2004-08-30 | 2006-03-02 | Albert Boeckh | Methoprene formulations for the control of tick infestations |
| CN1903029A (zh) * | 2005-07-27 | 2007-01-31 | 拜尔农作物科学有限公司 | 微乳剂 |
| HUE052378T2 (hu) | 2006-09-01 | 2021-04-28 | Fmc Corp | Lokális topikális adagolású, indoxacarb tartalmú formulációk |
| NZ552096A (en) * | 2006-12-15 | 2009-06-26 | Merial Ltd | Veterinary formulation |
| DE102006061538A1 (de) | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren |
| DE102006061537A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
| TW200846029A (en) * | 2007-02-09 | 2008-12-01 | Wyeth Corp | High dose, long-acting ectoparasiticide for extended control |
| WO2009070687A1 (en) * | 2007-11-26 | 2009-06-04 | Merial Limited | Solvent systems for pour-on formulations for combating parasites |
| US8404260B2 (en) | 2008-04-02 | 2013-03-26 | Bayer Cropscience Lp | Synergistic pesticide compositions |
| US20100041712A1 (en) * | 2008-08-18 | 2010-02-18 | Pfizer Inc. | Substituted imidazole combinations |
| GB2464449B (en) * | 2008-09-05 | 2011-10-12 | Norbrook Lab Ltd | A topical ectoparasticide composition |
| US9173728B2 (en) | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
| US8450357B2 (en) * | 2008-11-19 | 2013-05-28 | Merial Limited | Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof |
| PT2515646T (pt) | 2009-11-02 | 2017-03-28 | Meda Ab | Composições que compreendem extractos que contêm flavonóides de plantas do género citrus e/ou flavonóides citrus isolados e agentes surfactantes catiónicos especificos, e para utilizar a referida composição como um agente para tratar infestações com piolho da cabeça |
| UA108229C2 (uk) * | 2010-04-01 | 2015-04-10 | Інсектицидна композиція і спосіб боротьби з комахами за допомогою такої композиції | |
| UA108641C2 (uk) * | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| US8844193B2 (en) | 2010-10-19 | 2014-09-30 | Joseph Luongo | Apparatus for killing and removing ticks |
| DK2755473T3 (en) | 2011-09-12 | 2019-03-11 | Merial Inc | PARACITICIDE COMPOSITIONS CONTAINING AN ISOXAZOLINE ACTIVE SUBSTANCE, PROCEDURES AND APPLICATIONS THEREOF |
| ES2642715T3 (es) * | 2011-11-17 | 2017-11-17 | Merial, Inc. | Composiciones que comprenden un aril pirazol y un imidazol sustituido, procedimientos y utilizaciones de las mismas |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| ES2432465B1 (es) * | 2012-06-01 | 2014-07-17 | Química De Munguía S.A. (Quimunsa) | Sistema preventivo y curativo contra parásitos en entornos ganaderos y domésticos |
| US9314018B2 (en) * | 2012-06-25 | 2016-04-19 | Institut de Recherche en Semiochimie et Ethologie Appliquee | Feline scratch marking semiochemicals |
| EP2916810A4 (en) | 2012-10-16 | 2016-06-01 | Solano S P Ltd | TOPICAL FORMULATIONS FOR THE TREATMENT OF PARASITIC INFESTATIONS |
| US10258043B2 (en) * | 2012-10-26 | 2019-04-16 | Adama Makhteshim Ltd. | Pesticide compositions and methods for controlling invertebrate pests |
| US8993613B2 (en) * | 2013-04-17 | 2015-03-31 | The Hartz Mountain Corporation | Ectoparasiticidal formulations |
| WO2015112586A1 (en) | 2014-01-22 | 2015-07-30 | Duke University | Methods of treating pruritus |
| US10064871B2 (en) | 2014-01-22 | 2018-09-04 | Biomimetix Jv, Llc | Methods of treating skin disorders |
| RU2557986C1 (ru) * | 2014-07-31 | 2015-07-27 | Федеральное государственное бюджетное научное учреждение "Всероссийский научно-исследовательский институт ветеринарной энтомологии и арахнологии" (ФГБНУ ВНИИВЭА) | Способ защиты крупного рогатого скота от иксодовых клещей |
| CN105265460B (zh) * | 2015-02-12 | 2017-12-26 | 四川利尔作物科学有限公司 | 杀虫杀螨组合物及其应用 |
| AU2017202326A1 (en) * | 2016-04-07 | 2017-10-26 | Smartpak Equine Llc | Equine parasite treatment methods and compositions |
| US10512628B2 (en) | 2016-04-24 | 2019-12-24 | Solano S.P. Ltd. | Dinotefuran liquid flea and tick treatment |
| ES2668976B1 (es) * | 2016-10-21 | 2019-02-27 | Herrero Maria Del Pilar Mateo | Sustrato para el control de moscas y otros insectos, su proceso de fabricación y uso del sustrato como casa de animales. |
| BR112020012018A2 (pt) | 2017-12-15 | 2020-11-24 | Tarsus Pharmaceuticals, Inc. | formulações de parasiticida de isoxazolina e métodos para tratar blefarite |
| CN112006981B (zh) * | 2020-07-30 | 2023-01-10 | 瑞普（天津）生物药业有限公司 | 一种长效复方驱虫药物液体制剂及其制备方法与应用 |
| WO2023064241A1 (en) * | 2021-10-11 | 2023-04-20 | Valent Biosciences Llc | A mixture of pyrethroids and milbemycins and uses thereof |
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| US3781355A (en) | 1969-12-12 | 1973-12-25 | Boots Pure Drug Co Ltd | Pesticidal compounds and compositions |
| US3864497A (en) | 1970-12-01 | 1975-02-04 | Boots Pure Drug Co Ltd | Acaricidal and insecticidal 1,5-diphenyl-3-methyl-1,3,5-triazapenta-1,4-diener |
| US3950360A (en) | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| SE434277B (sv) | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| JPS5338621A (en) * | 1976-09-16 | 1978-04-08 | Nissan Chem Ind Ltd | Miticidal composition |
| JPS5341428A (en) * | 1976-09-27 | 1978-04-14 | Nissan Chem Ind Ltd | Miticidal composition |
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- 2004-12-17 KR KR1020067014316A patent/KR101187235B1/ko active IP Right Grant
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- 2004-12-17 JP JP2006545460A patent/JP4926719B2/ja active Active
- 2004-12-17 WO PCT/US2004/042379 patent/WO2005058038A1/en active Application Filing
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