AU2007267692B2 - Compounds and methods for modulating FXR - Google Patents

Info

Publication number

AU2007267692B2

AU2007267692B2 AU2007267692A AU2007267692A AU2007267692B2 AU 2007267692 B2 AU2007267692 B2 AU 2007267692B2 AU 2007267692 A AU2007267692 A AU 2007267692A AU 2007267692 A AU2007267692 A AU 2007267692A AU 2007267692 B2 AU2007267692 B2 AU 2007267692B2

Authority

AU

Australia

Prior art keywords

methyl

phenyl

hydrogen

isopropyl

triazol

Prior art date

2006-05-24

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

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 195
• 238000000034 method Methods 0.000 title claims abstract description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 15
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 15
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 121
• 239000001257 hydrogen Substances 0.000 claims description 119
• -1 benzoisothiazolyl Chemical group 0.000 claims description 66
• 150000002431 hydrogen Chemical class 0.000 claims description 65
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 36
• 239000005711 Benzoic acid Substances 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000001153 fluoro group Chemical group F* 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
• 125000001041 indolyl group Chemical group 0.000 claims description 18
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 102100038495 Bile acid receptor Human genes 0.000 claims description 12
• 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 150000003626 triacylglycerols Chemical class 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 238000008214 LDL Cholesterol Methods 0.000 claims description 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 230000001404 mediated effect Effects 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 229910052701 rubidium Inorganic materials 0.000 claims description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 11
• POPANIGZHUWMKL-UHFFFAOYSA-N 4-[[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoic acid Chemical compound C=1C=C(OCC=2N(N=NC=2C(F)(F)F)C=2C(=CC=CC=2Cl)Cl)C=C(C)C=1N(C)CC1=CC=C(C(O)=O)C(C)=C1 POPANIGZHUWMKL-UHFFFAOYSA-N 0.000 claims 2
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
• SFYBFUNJECIUDC-UHFFFAOYSA-N 3-[[4-[[3-(2-chloro-6-fluorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2F)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 SFYBFUNJECIUDC-UHFFFAOYSA-N 0.000 claims 1
• VXSPMOACFPKZRC-UHFFFAOYSA-N 3-[[n,2-dimethyl-4-[[5-propan-2-yl-3-[2-(trifluoromethoxy)phenyl]triazol-4-yl]methoxy]anilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 VXSPMOACFPKZRC-UHFFFAOYSA-N 0.000 claims 1
• PBOQIQQEKMWEIF-UHFFFAOYSA-N 4-[[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 PBOQIQQEKMWEIF-UHFFFAOYSA-N 0.000 claims 1
• IJOWOXZRGNLVHF-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoic acid Chemical compound C=1C=C(OCC=2N(N=NC=2C2CC2)C=2C(=CC=CC=2Cl)Cl)C=C(C)C=1N(C)CC1=CC=C(C(O)=O)C(C)=C1 IJOWOXZRGNLVHF-UHFFFAOYSA-N 0.000 claims 1
• WNJCAUVBQDAAFY-UHFFFAOYSA-N 6-[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-propan-2-ylindazole-3-carboxylic acid Chemical compound C1=C2N(C(C)C)N=C(C(O)=O)C2=CC=C1C(C(=C1)C)=CC=C1OCC1=C(C(F)(F)F)N=NN1C1=C(Cl)C=CC=C1Cl WNJCAUVBQDAAFY-UHFFFAOYSA-N 0.000 claims 1
• BEGCLZGRPXQHPZ-UHFFFAOYSA-N 6-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-propan-2-ylindazole-3-carboxylic acid Chemical compound C1=C2N(C(C)C)N=C(C(O)=O)C2=CC=C1C(C(=C1)C)=CC=C1OCC1=C(C2CC2)N=NN1C1=C(Cl)C=CC=C1Cl BEGCLZGRPXQHPZ-UHFFFAOYSA-N 0.000 claims 1
• 101150038588 CHRNB1 gene Proteins 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• 125000003944 tolyl group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 235
• 238000002360 preparation method Methods 0.000 description 142
• 239000000243 solution Substances 0.000 description 107
• 238000006243 chemical reaction Methods 0.000 description 102
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 98
• 235000019439 ethyl acetate Nutrition 0.000 description 94
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 93
• 239000011541 reaction mixture Substances 0.000 description 83
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
• 239000000203 mixture Substances 0.000 description 73
• 230000002829 reductive effect Effects 0.000 description 73
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
• 239000012267 brine Substances 0.000 description 33
• 239000012044 organic layer Substances 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• 239000007787 solid Substances 0.000 description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• 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 description 30
• 239000007858 starting material Substances 0.000 description 30
• 239000010410 layer Substances 0.000 description 29
• 238000003818 flash chromatography Methods 0.000 description 28
• 238000005481 NMR spectroscopy Methods 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 26
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 25
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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 21
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
• 239000011734 sodium Substances 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
• 235000012000 cholesterol Nutrition 0.000 description 14
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 12
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 12
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 239000000741 silica gel Substances 0.000 description 11
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• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• IJVUIOCXNVEGKH-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methanol Chemical compound OCC1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl IJVUIOCXNVEGKH-UHFFFAOYSA-N 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 108010003814 member 2 group B nuclear receptor subfamily 0 Proteins 0.000 description 10
• 239000000377 silicon dioxide Substances 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• 239000005909 Kieselgur Substances 0.000 description 9
• 102100023172 Nuclear receptor subfamily 0 group B member 2 Human genes 0.000 description 9
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• KTORKRBAIRTBCP-UHFFFAOYSA-N 1,2-benzothiazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NSC2=C1 KTORKRBAIRTBCP-UHFFFAOYSA-N 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 239000006188 syrup Substances 0.000 description 8
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• 238000003556 assay Methods 0.000 description 7
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• 125000001188 haloalkyl group Chemical group 0.000 description 7
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
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• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
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• BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-UHFFFAOYSA-N 0.000 description 5
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• LHJKZERUIPGPCK-UHFFFAOYSA-N methyl 4-formyl-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1C LHJKZERUIPGPCK-UHFFFAOYSA-N 0.000 description 5
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• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 239000000556 agonist Substances 0.000 description 4
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• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• SKZJYJMYLUQJPG-UHFFFAOYSA-N methyl 6-bromo-1h-indole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=CNC2=C1 SKZJYJMYLUQJPG-UHFFFAOYSA-N 0.000 description 4
• 229920000728 polyester Polymers 0.000 description 4
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• 210000002966 serum Anatomy 0.000 description 4
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• HFJZDPWNYGWWQZ-UHFFFAOYSA-N methyl 4-[2-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-2-methylphenyl]propan-2-ylsulfanyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC(C)(C)C(C(=C1)C)=CC=C1OCC1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl HFJZDPWNYGWWQZ-UHFFFAOYSA-N 0.000 description 1
• WQIOUBBFTOIXBD-UHFFFAOYSA-N methyl 4-[4-hydroxy-2-(trifluoromethyl)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C(F)(F)F WQIOUBBFTOIXBD-UHFFFAOYSA-N 0.000 description 1
• YBMURXWJPXNOQB-UHFFFAOYSA-N methyl 4-[[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C(F)(F)F)N=NN1C1=C(Cl)C=CC=C1Cl YBMURXWJPXNOQB-UHFFFAOYSA-N 0.000 description 1
• CGGGWRDRBMSXOL-UHFFFAOYSA-N methyl 4-formyl-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1C(F)(F)F CGGGWRDRBMSXOL-UHFFFAOYSA-N 0.000 description 1
• BTZOMWXSWVOOHG-UHFFFAOYSA-N methyl 4-sulfanylbenzoate Chemical compound COC(=O)C1=CC=C(S)C=C1 BTZOMWXSWVOOHG-UHFFFAOYSA-N 0.000 description 1
• ZCPCZELMTZDPAK-UHFFFAOYSA-N methyl 5-(4-hydroxy-2-methylphenyl)-4-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C)=C1C1=CC=C(O)C=C1C ZCPCZELMTZDPAK-UHFFFAOYSA-N 0.000 description 1
• LIQIPOFQWQLBCQ-UHFFFAOYSA-N methyl 5-(4-hydroxy-2-methylphenyl)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C LIQIPOFQWQLBCQ-UHFFFAOYSA-N 0.000 description 1
• MSCOMZNDKVOGGI-UHFFFAOYSA-N methyl 5-(4-hydroxyphenyl)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1 MSCOMZNDKVOGGI-UHFFFAOYSA-N 0.000 description 1
• UYFFMVDJHCONSM-UHFFFAOYSA-N methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)triazole-4-carboxylate Chemical compound COC(=O)C1=C(C2CC2)N=NN1C1=C(Cl)C=CC=C1Cl UYFFMVDJHCONSM-UHFFFAOYSA-N 0.000 description 1
• INSNZBHWOMPOKH-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-benzothiophene-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CSC2=CC=1C1=CC=C(O)C=C1C INSNZBHWOMPOKH-UHFFFAOYSA-N 0.000 description 1
• NRTWWGSSWOLVHM-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-methylindole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CN(C)C2=CC=1C1=CC=C(O)C=C1C NRTWWGSSWOLVHM-UHFFFAOYSA-N 0.000 description 1
• XXEWKZYLPOJIIL-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-propan-2-ylindole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CN(C(C)C)C2=CC=1C1=CC=C(O)C=C1C XXEWKZYLPOJIIL-UHFFFAOYSA-N 0.000 description 1
• UVTAKNMJKKEKED-UHFFFAOYSA-N methyl 6-[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-benzothiophene-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CSC2=CC=1C(C(=C1)C)=CC=C1OCC1=C(C(F)(F)F)N=NN1C1=C(Cl)C=CC=C1Cl UVTAKNMJKKEKED-UHFFFAOYSA-N 0.000 description 1
• LFFOXNXUGCBVHQ-UHFFFAOYSA-N methyl 6-[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-propan-2-ylindazole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=NN(C(C)C)C2=CC=1C(C(=C1)C)=CC=C1OCC1=C(C(F)(F)F)N=NN1C1=C(Cl)C=CC=C1Cl LFFOXNXUGCBVHQ-UHFFFAOYSA-N 0.000 description 1
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