OA13346A - Topical formulations comprising a 1-N-arylpyrazolederivative and a formamidine. - Google Patents

Topical formulations comprising a 1-N-arylpyrazolederivative and a formamidine. Download PDF

Info

Publication number: OA13346A
Authority: OA; OAPI
Prior art keywords: alkyl; haloalkyl; hydrogen; parasitical; halogen
Prior art date: 2003-12-17

Application number

OA1200600204A

Other languages

English (en)

Inventor

Albert Boeckh

Luiz Gustavo Cramer

Mark D Soll

Original Assignee

Merial Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-12-17

Filing date

2004-12-17

Publication date

2007-04-13

2004-12-17 Application filed by Merial Ltd filed Critical Merial Ltd

2007-04-13 Publication of OA13346A publication Critical patent/OA13346A/en

Links

239000012049 topical pharmaceutical composition Substances 0.000 title claims abstract description 23
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 title claims description 11
239000000203 mixture Substances 0.000 claims abstract description 90
150000001875 compounds Chemical class 0.000 claims abstract description 83
238000009472 formulation Methods 0.000 claims abstract description 73
229960002587 amitraz Drugs 0.000 claims abstract description 30
QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound 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 abstract description 30
244000045947 parasite Species 0.000 claims abstract description 25
239000005660 Abamectin Substances 0.000 claims abstract description 21
241000238876 Acari Species 0.000 claims abstract description 19
239000004544 spot-on Substances 0.000 claims abstract description 18
241000124008 Mammalia Species 0.000 claims abstract description 15
239000004540 pour-on Substances 0.000 claims abstract description 13
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 claims abstract description 12
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 claims abstract description 12
239000007921 spray Substances 0.000 claims abstract description 6
239000002728 pyrethroid Substances 0.000 claims abstract description 5
230000000507 anthelmentic effect Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 98
125000001188 haloalkyl group Chemical group 0.000 claims description 65
-1 diethyl phthalate fatty acid esters Chemical class 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 56
229910052736 halogen Inorganic materials 0.000 claims description 42
150000002367 halogens Chemical class 0.000 claims description 39
125000005843 halogen group Chemical group 0.000 claims description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 27
125000004438 haloalkoxy group Chemical group 0.000 claims description 27
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
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 20
239000002904 solvent Substances 0.000 claims description 20
239000007788 liquid Substances 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
239000005899 Fipronil Substances 0.000 claims description 18
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 18
229940013764 fipronil Drugs 0.000 claims description 18
239000003112 inhibitor Substances 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
239000003981 vehicle Substances 0.000 claims description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
125000003282 alkyl amino group Chemical group 0.000 claims description 15
125000000262 haloalkenyl group Chemical group 0.000 claims description 15
125000000304 alkynyl group Chemical group 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
239000003795 chemical substances by application Substances 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
241000282326 Felis catus Species 0.000 claims description 11
241000238631 Hexapoda Species 0.000 claims description 11
238000002425 crystallisation Methods 0.000 claims description 11
230000008025 crystallization Effects 0.000 claims description 11
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 11
239000004094 surface-active agent Substances 0.000 claims description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
235000014113 dietary fatty acids Nutrition 0.000 claims description 10
229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 10
229930195729 fatty acid Natural products 0.000 claims description 10
239000000194 fatty acid Substances 0.000 claims description 10
125000000232 haloalkynyl group Chemical group 0.000 claims description 10
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 10
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 9
239000003093 cationic surfactant Substances 0.000 claims description 9
125000005347 halocycloalkyl group Chemical group 0.000 claims description 9
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
229920001577 copolymer Polymers 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
229920001223 polyethylene glycol Polymers 0.000 claims description 8
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 8
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 8
229940068968 polysorbate 80 Drugs 0.000 claims description 8
229920000053 polysorbate 80 Polymers 0.000 claims description 8
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 description 7
239000004255 Butylated hydroxyanisole Substances 0.000 claims description 7
239000004322 Butylated hydroxytoluene Substances 0.000 claims description 7
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 description 7
125000003118 aryl group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 7
229940043253 butylated hydroxyanisole Drugs 0.000 claims description 7
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 claims description 7
235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 7
229940095259 butylated hydroxytoluene Drugs 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
150000004665 fatty acids Chemical class 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 7
239000004215 Carbon black (E152) Substances 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
239000006184 cosolvent Substances 0.000 claims description 6
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
239000002736 nonionic surfactant Substances 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
239000002280 amphoteric surfactant Substances 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
235000011187 glycerol Nutrition 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 5
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
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 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
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 description 4
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 description 4
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 description 4
229930195725 Mannitol Natural products 0.000 claims description 4
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
239000001768 carboxy methyl cellulose Substances 0.000 claims description 4
239000004359 castor oil Substances 0.000 claims description 4
235000019438 castor oil Nutrition 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
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 description 4
125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
239000000787 lecithin Substances 0.000 claims description 4
235000010445 lecithin Nutrition 0.000 claims description 4
229940067606 lecithin Drugs 0.000 claims description 4
239000000594 mannitol Substances 0.000 claims description 4
235000010355 mannitol Nutrition 0.000 claims description 4
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 description 4
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 4
229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 4
239000000600 sorbitol Substances 0.000 claims description 4
235000010356 sorbitol Nutrition 0.000 claims description 4
230000000699 topical effect Effects 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
150000005215 alkyl ethers Chemical class 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
239000003945 anionic surfactant Substances 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
230000002141 anti-parasite Effects 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
230000003078 antioxidant effect Effects 0.000 claims description 3
235000006708 antioxidants Nutrition 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 claims description 3
229940093476 ethylene glycol Drugs 0.000 claims description 3
239000003630 growth substance Substances 0.000 claims description 3
125000004992 haloalkylamino group Chemical group 0.000 claims description 3
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
229920000223 polyglycerol Polymers 0.000 claims description 3
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
ITCAUAYQCALGGV-XTICBAGASA-M sodium;(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound [Na+].C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C([O-])=O ITCAUAYQCALGGV-XTICBAGASA-M 0.000 claims description 3
HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 claims description 3
125000004961 1-arylpyrazolyl group Chemical group 0.000 claims description 2
125000006414 CCl Chemical group ClC* 0.000 claims description 2
125000006193 alkinyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
235000010323 ascorbic acid Nutrition 0.000 claims description 2
239000011668 ascorbic acid Substances 0.000 claims description 2
229960005070 ascorbic acid Drugs 0.000 claims description 2
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
239000000473 propyl gallate Substances 0.000 claims description 2
235000010388 propyl gallate Nutrition 0.000 claims description 2
229940075579 propyl gallate Drugs 0.000 claims description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 2
239000004296 sodium metabisulphite Substances 0.000 claims description 2
235000010262 sodium metabisulphite Nutrition 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-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
238000004519 manufacturing process Methods 0.000 claims 1
238000000034 method Methods 0.000 abstract description 20
241001465754 Metazoa Species 0.000 abstract description 18
244000078703 ectoparasite Species 0.000 abstract description 13
206010061217 Infestation Diseases 0.000 abstract description 10
239000002917 insecticide Substances 0.000 abstract description 9
241000255925 Diptera Species 0.000 abstract description 8
241001674048 Phthiraptera Species 0.000 abstract description 7
241000283690 Bos taurus Species 0.000 abstract description 5
UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical class C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 abstract description 4
241000258242 Siphonaptera Species 0.000 abstract description 4
150000001556 benzimidazoles Chemical class 0.000 abstract description 4
229940124339 anthelmintic agent Drugs 0.000 abstract description 3
239000000921 anthelmintic agent Substances 0.000 abstract description 3
RFEJUZJILGIRHQ-XRIOVQLTSA-N 2,3-dihydroxybutanedioic acid;3-[(2s)-1-methylpyrrolidin-2-yl]pyridine Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O.CN1CCC[C@H]1C1=CC=CN=C1 RFEJUZJILGIRHQ-XRIOVQLTSA-N 0.000 abstract description 2
208000035056 Tick-Borne disease Diseases 0.000 abstract description 2
239000013057 ectoparasiticide Substances 0.000 abstract description 2
201000002266 mite infestation Diseases 0.000 abstract description 2
208000016523 tick-borne infectious disease Diseases 0.000 abstract description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 24
150000002431 hydrogen Chemical group 0.000 description 19
241000282472 Canis lupus familiaris Species 0.000 description 15
208000015181 infectious disease Diseases 0.000 description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
239000004530 micro-emulsion Substances 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 9
238000011282 treatment Methods 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
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 6
241000271566 Aves Species 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
229950008167 abamectin Drugs 0.000 description 6
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239000010773 plant oil Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940104257 polyglyceryl-6-dioleate Drugs 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940095574 propionic acid Drugs 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
230000005180 public health Effects 0.000 description 1
XTAIYAYAHZCMOG-UHFFFAOYSA-N pyrazol-4-ylidenemethanethione Chemical compound S=C=C1C=NN=C1 XTAIYAYAHZCMOG-UHFFFAOYSA-N 0.000 description 1
ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
229940070846 pyrethrins Drugs 0.000 description 1
NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
229960002245 selamectin Drugs 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002699 waste material Substances 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
- A01N43/48—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)
Environmental Sciences (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General 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)

OA1200600204A 2003-12-17 2004-12-17 Topical formulations comprising a 1-N-arylpyrazolederivative and a formamidine. OA13346A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
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

Publications (1)

Publication Number	Publication Date
OA13346A true OA13346A (en)	2007-04-13

Family

ID=34681575

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200600204A OA13346A (en)	2003-12-17	2004-12-17	Topical formulations comprising a 1-N-arylpyrazolederivative and a formamidine.

Country Status (21)

Country	Link
US (3)	US7531186B2 (es)
EP (1)	EP1694123B1 (es)
JP (2)	JP4926719B2 (es)
KR (1)	KR101187235B1 (es)
CN (1)	CN1905794B (es)
AP (1)	AP2083A (es)
AU (2)	AU2004299120B2 (es)
BR (1)	BRPI0417209B1 (es)
CA (1)	CA2550256C (es)
CO (1)	CO5700671A2 (es)
CR (2)	CR8464A (es)
ES (1)	ES2650713T3 (es)
IL (1)	IL176360A (es)
IN (1)	IN2012DN02432A (es)
NO (1)	NO336284B1 (es)
NZ (2)	NZ578628A (es)
OA (1)	OA13346A (es)
PL (2)	PL210628B1 (es)
RU (1)	RU2361401C2 (es)
WO (1)	WO2005058038A1 (es)
ZA (1)	ZA200605109B (es)

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2004
- 2004-02-20 US US10/783,459 patent/US7531186B2/en active Active
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2006
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Also Published As

Publication number	Publication date
EP1694123A1 (en)	2006-08-30
AU2004299120A1 (en)	2005-06-30
CN1905794A (zh)	2007-01-31
NZ578628A (en)	2011-01-28
NO20063234L (no)	2006-09-14
ES2650713T3 (es)	2018-01-22
WO2005058038A1 (en)	2005-06-30
AU2004299120B2 (en)	2011-05-12
KR20060131807A (ko)	2006-12-20
EP1694123A4 (en)	2012-04-25
US8242161B2 (en)	2012-08-14
JP4926719B2 (ja)	2012-05-09
JP2007517782A (ja)	2007-07-05
EP1694123B1 (en)	2017-09-06
PL210628B1 (pl)	2012-02-29
CO5700671A2 (es)	2006-11-30
BRPI0417209B1 (pt)	2018-06-26
CN1905794B (zh)	2011-12-14
CA2550256A1 (en)	2005-06-30
US7531186B2 (en)	2009-05-12
IL176360A (en)	2015-09-24
RU2361401C2 (ru)	2009-07-20
NZ548178A (en)	2009-08-28
US9066515B2 (en)	2015-06-30
US20130023490A1 (en)	2013-01-24
PL393289A1 (pl)	2011-05-23
KR101187235B1 (ko)	2012-10-02
BRPI0417209A (pt)	2007-02-06
CA2550256C (en)	2013-04-16
RU2006125432A (ru)	2008-01-27
CR8464A (es)	2007-01-31
ZA200605109B (en)	2007-11-28
JP2012102133A (ja)	2012-05-31
US20050137244A1 (en)	2005-06-23
PL380682A1 (pl)	2007-03-05
IN2012DN02432A (es)	2015-08-21
AP2006003661A0 (en)	2006-06-30
AU2011202218B2 (en)	2011-12-22
CR20120144A (es)	2012-05-24
AP2083A (en)	2010-01-04
NO336284B1 (no)	2015-07-13
AU2011202218A1 (en)	2011-06-02
US20090192207A1 (en)	2009-07-30
IL176360A0 (en)	2006-10-05

Publication	Publication Date	Title
CA2550256C (en)	2013-04-16	Topical formulations comprising a 1-n-arylpyrazole derivative and a formamidine
CA2517135C (en)	2012-07-03	1-n-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases
US20080003282A1 (en)	2008-01-03	Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals
US20050234119A1 (en)	2005-10-20	Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals
ZA200502904B (en)	2005-10-19	Nodulisporic acid derivative spot-on formulations for combating parasites.
MXPA06006961A (es)	2006-12-13	Formulaciones topicas que comprenden un derivado de 1-n-arilpirazol y una formamidina
HK1078439A (en)	2006-03-17	1-n-arylpyrazole derivatives for interrupting the transmission of mosquito-borne diseases
HK1078439B (en)	2021-01-29	1-n-arylpyrazole derivatives for interrupting the transmission of mosquito-borne diseases