HUE029006T2 - Antiparasitic dihydroazole compounds and compositions comprising same - Google Patents

Info

Publication number

HUE029006T2

HUE029006T2 HUE10796566A HUE10796566A HUE029006T2 HU E029006 T2 HUE029006 T2 HU E029006T2 HU E10796566 A HUE10796566 A HU E10796566A HU E10796566 A HUE10796566 A HU E10796566A HU E029006 T2 HUE029006 T2 HU E029006T2

Authority

HU

Hungary

Prior art keywords

alkyl

haloalkyl

compound

hydrogen

formula

Prior art date

2009-12-17

Links

• Espacenet
• Global Dossier
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• 239000000203 mixture Substances 0.000 title claims abstract description 219
• 150000001875 compounds Chemical class 0.000 title claims description 421
• 239000003096 antiparasitic agent Substances 0.000 title description 5
• 230000002141 anti-parasite Effects 0.000 title description 4
• 238000000034 method Methods 0.000 claims abstract description 79
• 241001465754 Metazoa Species 0.000 claims abstract description 64
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 206010061217 Infestation Diseases 0.000 claims abstract description 25
• 238000002360 preparation method Methods 0.000 claims abstract description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 211
• 239000001257 hydrogen Substances 0.000 claims description 211
• -1 alpha Chemical group 0.000 claims description 188
• 150000002431 hydrogen Chemical class 0.000 claims description 149
• 125000001188 haloalkyl group Chemical group 0.000 claims description 128
• 125000000217 alkyl group Chemical group 0.000 claims description 119
• 229910052760 oxygen Inorganic materials 0.000 claims description 118
• 239000001301 oxygen Substances 0.000 claims description 114
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 113
• 229910052736 halogen Inorganic materials 0.000 claims description 109
• 150000002367 halogens Chemical class 0.000 claims description 107
• 125000003342 alkenyl group Chemical group 0.000 claims description 88
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 79
• 125000000304 alkynyl group Chemical group 0.000 claims description 79
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 79
• 125000003118 aryl group Chemical group 0.000 claims description 65
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
• 241000196324 Embryophyta Species 0.000 claims description 37
• 239000000463 material Substances 0.000 claims description 36
• 238000011282 treatment Methods 0.000 claims description 34
• 238000006243 chemical reaction Methods 0.000 claims description 33
• 241000607479 Yersinia pestis Species 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 21
• 239000000126 substance Substances 0.000 claims description 21
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 208000015181 infectious disease Diseases 0.000 claims description 15
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 14
• 150000001298 alcohols Chemical class 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 239000002689 soil Substances 0.000 claims description 5
• 150000003852 triazoles Chemical class 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
• 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
• 208000019901 Anxiety disease Diseases 0.000 claims 1
• 241000238558 Eucarida Species 0.000 claims 1
• 241000027355 Ferocactus setispinus Species 0.000 claims 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
• 230000001154 acute effect Effects 0.000 claims 1
• 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
• 230000036506 anxiety Effects 0.000 claims 1
• 239000002738 chelating agent Substances 0.000 claims 1
• 235000012000 cholesterol Nutrition 0.000 claims 1
• 239000000551 dentifrice Substances 0.000 claims 1
• 239000004744 fabric Substances 0.000 claims 1
• 239000002574 poison Substances 0.000 claims 1
• 231100000614 poison Toxicity 0.000 claims 1
• 238000011321 prophylaxis Methods 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 102200001903 rs762590894 Human genes 0.000 claims 1
• 208000030852 Parasitic disease Diseases 0.000 abstract description 14
• 230000008569 process Effects 0.000 abstract description 12
• 239000000575 pesticide Substances 0.000 abstract 1
• 235000013350 formula milk Nutrition 0.000 description 203
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 86
• 125000000232 haloalkynyl group Chemical group 0.000 description 72
• 238000009472 formulation Methods 0.000 description 64
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 125000004093 cyano group Chemical group *C#N 0.000 description 57
• 239000000243 solution Substances 0.000 description 52
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 46
• 125000001072 heteroaryl group Chemical group 0.000 description 43
• 230000002829 reductive effect Effects 0.000 description 39
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
• SHENXRCDBJGWNU-GOSISDBHSA-N 6-(1,3-benzothiazol-6-ylamino)-4-(cyclopropylamino)-n-[(2r)-2-fluoro-3-hydroxy-3-methylbutyl]pyridine-3-carboxamide Chemical compound CC(C)(O)[C@H](F)CNC(=O)C1=CN=C(NC=2C=C3SC=NC3=CC=2)C=C1NC1CC1 SHENXRCDBJGWNU-GOSISDBHSA-N 0.000 description 36
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
• 239000013543 active substance Substances 0.000 description 35
• 239000002904 solvent Substances 0.000 description 33
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 32
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
• 238000005160 1H NMR spectroscopy Methods 0.000 description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 26
• 239000007787 solid Substances 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 239000012267 brine Substances 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
• 238000004587 chromatography analysis Methods 0.000 description 21
• 150000002148 esters Chemical class 0.000 description 21
• 239000003112 inhibitor Substances 0.000 description 21
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• 239000007864 aqueous solution Substances 0.000 description 19
• 230000002265 prevention Effects 0.000 description 19
• 238000012360 testing method Methods 0.000 description 19
• 125000006239 protecting group Chemical group 0.000 description 18
• 125000006350 alkyl thio alkyl group Chemical group 0.000 description 17
• 125000004995 haloalkylthio group Chemical group 0.000 description 17
• 239000004094 surface-active agent Substances 0.000 description 17
• 125000004001 thioalkyl group Chemical group 0.000 description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
• 238000004293 19F NMR spectroscopy Methods 0.000 description 16
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 16
• 229910052938 sodium sulfate Inorganic materials 0.000 description 16
• 235000011152 sodium sulphate Nutrition 0.000 description 16
• 239000002023 wood Substances 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 238000002425 crystallisation Methods 0.000 description 15
• 230000008025 crystallization Effects 0.000 description 15
• 239000008187 granular material Substances 0.000 description 15
• 102200128931 rs3737311 Human genes 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 230000015572 biosynthetic process Effects 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 238000005859 coupling reaction Methods 0.000 description 14
• 235000014113 dietary fatty acids Nutrition 0.000 description 14
• 239000000839 emulsion Substances 0.000 description 14
• 239000000194 fatty acid Substances 0.000 description 14
• 229930195729 fatty acid Natural products 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• 239000004544 spot-on Substances 0.000 description 14
• 239000005660 Abamectin Chemical class 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• 150000001408 amides Chemical class 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 239000006184 cosolvent Substances 0.000 description 13
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
• 229920001223 polyethylene glycol Polymers 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 238000010790 dilution Methods 0.000 description 12
• 239000012895 dilution Substances 0.000 description 12
• 239000002270 dispersing agent Substances 0.000 description 12
• 235000011187 glycerol Nutrition 0.000 description 12
• 229960005150 glycerol Drugs 0.000 description 12
• 239000000543 intermediate Substances 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 239000003960 organic solvent Substances 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 11
• 244000078703 ectoparasite Species 0.000 description 11
• 125000000623 heterocyclic group Chemical group 0.000 description 11
• 230000000361 pesticidal effect Effects 0.000 description 11
• 229940068917 polyethylene glycols Drugs 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 238000006467 substitution reaction Methods 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• 239000003085 diluting agent Substances 0.000 description 10
• 150000004665 fatty acids Chemical class 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 239000004530 micro-emulsion Substances 0.000 description 10
• 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 10
• 235000019198 oils Nutrition 0.000 description 10
• 244000045947 parasite Species 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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• 125000005347 halocycloalkyl group Chemical group 0.000 description 9
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• 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 9
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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• 238000000844 transformation Methods 0.000 description 7
• 239000004562 water dispersible granule Substances 0.000 description 7
• CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 6
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• 241000258924 Ctenocephalides felis Species 0.000 description 6
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
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• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
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• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 241000258242 Siphonaptera Species 0.000 description 5
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• 239000007859 condensation product Substances 0.000 description 5
• 229910052802 copper Inorganic materials 0.000 description 5
• 239000010949 copper Substances 0.000 description 5
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 5
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