KR20140034743A - 체외기생충 구제용 활성 화합물의 배합물 - Google Patents

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Publication number

KR20140034743A

KR20140034743A KR1020137018518A KR20137018518A KR20140034743A KR 20140034743 A KR20140034743 A KR 20140034743A KR 1020137018518 A KR1020137018518 A KR 1020137018518A KR 20137018518 A KR20137018518 A KR 20137018518A KR 20140034743 A KR20140034743 A KR 20140034743A

Authority

KR

South Korea

Prior art keywords

alkyl

spp

haloalkyl

alkoxy

halogen

Prior art date

2010-12-21

Legal status (The legal status 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 status listed.)

Ceased

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• Espacenet
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• 239000013543 active substance Substances 0.000 title 1
• 230000001984 ectoparasiticidal effect Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 106
• 244000045947 parasite Species 0.000 claims abstract description 26
• 238000000338 in vitro Methods 0.000 claims abstract description 20
• 241001465754 Metazoa Species 0.000 claims abstract description 19
• -1 dialkylsulfonylamino Chemical group 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 125000003545 alkoxy group Chemical group 0.000 claims description 55
• 125000001188 haloalkyl group Chemical group 0.000 claims description 51
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical group 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 239000003112 inhibitor Substances 0.000 claims description 24
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 23
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 125000004414 alkyl thio group Chemical group 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 19
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
• 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 7
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 7
• 239000000556 agonist Substances 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 230000001419 dependent effect Effects 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 239000000018 receptor agonist Substances 0.000 claims description 7
• 229940044601 receptor agonist Drugs 0.000 claims description 7
• 239000003195 sodium channel blocking agent Substances 0.000 claims description 7
• 102000012440 Acetylcholinesterase Human genes 0.000 claims description 6
• 108010022752 Acetylcholinesterase Proteins 0.000 claims description 6
• 229920002101 Chitin Polymers 0.000 claims description 6
• 229940022698 acetylcholinesterase Drugs 0.000 claims description 6
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
• 230000015572 biosynthetic process Effects 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
• FXJRDUKXWHFPND-NSHDSACASA-N 2-[(1s)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C1([C@@H](C)C=2C(=C(C)C=CC=2)C)=NC=CN1 FXJRDUKXWHFPND-NSHDSACASA-N 0.000 claims description 5
• 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 5
• ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound 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 5
• 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 5
• JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 5
• 239000005946 Cypermethrin Substances 0.000 claims description 5
• 239000005892 Deltamethrin Substances 0.000 claims description 5
• 239000005899 Fipronil Substances 0.000 claims description 5
• 239000005906 Imidacloprid Substances 0.000 claims description 5
• 239000005930 Spinosad Substances 0.000 claims description 5
• INISTDXBRIBGOC-CGAIIQECSA-N [cyano-(3-phenoxyphenyl)methyl] (2s)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate Chemical compound N([C@@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-CGAIIQECSA-N 0.000 claims description 5
• YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
• 229960002587 amitraz Drugs 0.000 claims description 5
• 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 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
• 229960001591 cyfluthrin Drugs 0.000 claims description 5
• QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 5
• 229960005424 cypermethrin Drugs 0.000 claims description 5
• KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 5
• 229960002483 decamethrin Drugs 0.000 claims description 5
• OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 5
• 229950003960 demiditraz Drugs 0.000 claims description 5
• YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 5
• QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin 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](C3CCCCC3)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 QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 claims description 5
• 229960003997 doramectin Drugs 0.000 claims description 5
• WPNHOHPRXXCPRA-TVXIRPTOSA-N eprinomectin Chemical compound O1[C@@H](C)[C@@H](NC(C)=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 WPNHOHPRXXCPRA-TVXIRPTOSA-N 0.000 claims description 5
• 229960002346 eprinomectin Drugs 0.000 claims description 5
• 229940013764 fipronil Drugs 0.000 claims description 5
• JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 claims description 5
• 229940056881 imidacloprid Drugs 0.000 claims description 5
• YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 5
• 229960002418 ivermectin Drugs 0.000 claims description 5
• 229960000490 permethrin Drugs 0.000 claims description 5
• RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 5
• 229940014213 spinosad Drugs 0.000 claims description 5
• CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 claims description 4
• CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 claims description 4
• FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 claims description 4
• 241000125205 Anethum Species 0.000 claims description 4
• 108010009685 Cholinergic Receptors Proteins 0.000 claims description 4
• 239000005896 Etofenprox Substances 0.000 claims description 4
• 108010052164 Sodium Channels Proteins 0.000 claims description 4
• 102000018674 Sodium Channels Human genes 0.000 claims description 4
• 239000005929 Spinetoram Substances 0.000 claims description 4
• GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 claims description 4
• 102000034337 acetylcholine receptors Human genes 0.000 claims description 4
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 4
• 230000003281 allosteric effect Effects 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 150000003857 carboxamides Chemical class 0.000 claims description 4
• 239000003467 chloride channel stimulating agent Substances 0.000 claims description 4
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
• YUAUPYJCVKNAEC-SEYXRHQNSA-N cymiazole Chemical compound CC1=CC(C)=CC=C1\N=C/1N(C)C=CS\1 YUAUPYJCVKNAEC-SEYXRHQNSA-N 0.000 claims description 4
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 4
• YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 claims description 4
• 229950005085 etofenprox Drugs 0.000 claims description 4
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
• 229940079888 nitenpyram Drugs 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 150000002923 oximes Chemical class 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229960005235 piperonyl butoxide Drugs 0.000 claims description 4
• UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 4
• 229960005199 tetramethrin Drugs 0.000 claims description 4
• AWSZRJQNBMEZOI-UHFFFAOYSA-N 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate Chemical compound C=1C=C(C(C)(C)C)C=CC=1C(C#N)(C(=O)OCCOC)C(=O)C1=CC=CC=C1C(F)(F)F AWSZRJQNBMEZOI-UHFFFAOYSA-N 0.000 claims description 3
• 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 3
• 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 3
• 229940121683 Acetylcholine receptor antagonist Drugs 0.000 claims description 3
• 108010018763 Biotin carboxylase Proteins 0.000 claims description 3
• 101100421668 Caenorhabditis elegans slo-1 gene Proteins 0.000 claims description 3
• 229940123715 Chloride channel antagonist Drugs 0.000 claims description 3
• 239000005655 Cyflumetofen Substances 0.000 claims description 3
• 102000015782 Electron Transport Complex III Human genes 0.000 claims description 3
• 108010024882 Electron Transport Complex III Proteins 0.000 claims description 3
• 239000005926 Pyridalyl Substances 0.000 claims description 3
• 239000005934 Sulfoxaflor Substances 0.000 claims description 3
• ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 3
• 239000012636 effector Substances 0.000 claims description 3
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• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
• 230000010627 oxidative phosphorylation Effects 0.000 claims description 3
• AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 claims description 3
• 229940125794 sodium channel blocker Drugs 0.000 claims description 3
• VOKAJVSKGOCKRU-UHFFFAOYSA-N 4-(3,5-dichloro-4-methoxyphenyl)-2-(3-ethoxypyrazin-2-yl)-5-(trifluoromethyl)pyrazol-3-amine Chemical compound CCOC1=NC=CN=C1N1C(N)=C(C=2C=C(Cl)C(OC)=C(Cl)C=2)C(C(F)(F)F)=N1 VOKAJVSKGOCKRU-UHFFFAOYSA-N 0.000 claims description 2
• PUAAPBBXXVGAJX-UHFFFAOYSA-N 4-[3,5-dichloro-4-(dimethylamino)phenyl]-2-(3-ethoxypyrazin-2-yl)-5-(trifluoromethyl)pyrazol-3-amine Chemical compound CCOC1=NC=CN=C1N1C(N)=C(C=2C=C(Cl)C(N(C)C)=C(Cl)C=2)C(C(F)(F)F)=N1 PUAAPBBXXVGAJX-UHFFFAOYSA-N 0.000 claims description 2
• 229940126062 Compound A Drugs 0.000 claims description 2
• UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 claims description 2
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
• 150000001204 N-oxides Chemical class 0.000 claims description 2
• 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims description 2
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
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