JP5119241B2 - Ｆｘｒアゴニスト - Google Patents

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Publication number

JP5119241B2

JP5119241B2 JP2009512259A JP2009512259A JP5119241B2 JP 5119241 B2 JP5119241 B2 JP 5119241B2 JP 2009512259 A JP2009512259 A JP 2009512259A JP 2009512259 A JP2009512259 A JP 2009512259A JP 5119241 B2 JP5119241 B2 JP 5119241B2

Authority

JP

Japan

Prior art keywords

methyl

phenyl

isopropyl

alkyl

mmol

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.)

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• 229940121360 farnesoid X receptor (fxr) agonists Drugs 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 310
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 184
• 229910052739 hydrogen Inorganic materials 0.000 claims description 133
• 239000001257 hydrogen Substances 0.000 claims description 131
• 150000002431 hydrogen Chemical class 0.000 claims description 100
• 239000000460 chlorine Substances 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 41
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 239000011737 fluorine Substances 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 17
• 125000001041 indolyl group Chemical group 0.000 claims description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 16
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 14
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 10
• 239000005711 Benzoic acid Substances 0.000 claims description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
• 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 description 8
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• PSEWBWUHJNKCHR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 PSEWBWUHJNKCHR-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 8
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
• ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical group CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 2
• GGNHFTLUMHDWKB-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]indole-3-carboxylic acid Chemical compound C=1C=C(C=2C=C3N(C)C=C(C3=CC=2)C(O)=O)C(C)=CC=1OCC1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F GGNHFTLUMHDWKB-UHFFFAOYSA-N 0.000 claims 1
• RLJHXZZDXOVPKO-UHFFFAOYSA-N 2-(butanoylamino)-4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)CCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 RLJHXZZDXOVPKO-UHFFFAOYSA-N 0.000 claims 1
• ACXZZSVJTYLZNP-UHFFFAOYSA-N 2-butoxy-4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCCCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 ACXZZSVJTYLZNP-UHFFFAOYSA-N 0.000 claims 1
• FZXSJMZVSAPXFE-UHFFFAOYSA-N 2-butoxy-5-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCCCC)=CC=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl FZXSJMZVSAPXFE-UHFFFAOYSA-N 0.000 claims 1
• HUMDEMOEWLRNNM-UHFFFAOYSA-N 2-methoxy-5-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN(C)C(C(=N1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F HUMDEMOEWLRNNM-UHFFFAOYSA-N 0.000 claims 1
• ZCGIYEVATNPATF-UHFFFAOYSA-N 2-methyl-4-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(N=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C)=C1 ZCGIYEVATNPATF-UHFFFAOYSA-N 0.000 claims 1
• SZUCNHMTJUGQAM-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-4-fluorobenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC(C(O)=O)=CC=C1F SZUCNHMTJUGQAM-UHFFFAOYSA-N 0.000 claims 1
• JDMOVNWTUBRGJG-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl JDMOVNWTUBRGJG-UHFFFAOYSA-N 0.000 claims 1
• LFMFHOSIFXYMRP-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-5-(trifluoromethyl)benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC(C(O)=O)=CC(C(F)(F)F)=C1 LFMFHOSIFXYMRP-UHFFFAOYSA-N 0.000 claims 1
• QYBBADGECQOJHZ-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-5-methylbenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC(C)=CC(C(O)=O)=C1 QYBBADGECQOJHZ-UHFFFAOYSA-N 0.000 claims 1
• JOPUCUPZVDBNPA-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 JOPUCUPZVDBNPA-UHFFFAOYSA-N 0.000 claims 1
• JDJSBOVIXJVINF-UHFFFAOYSA-N 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n-ethyl-2-methylanilino]methyl]benzoic acid Chemical compound C=1C=C(OCC=2N(N=CC=2C(C)C)C=2C(=CC=CC=2Cl)Cl)C=C(C)C=1N(CC)CC1=CC=CC(C(O)=O)=C1 JDJSBOVIXJVINF-UHFFFAOYSA-N 0.000 claims 1
• PNNSHXNLGFOCAJ-UHFFFAOYSA-N 3-[[[4-[[4-cyclopropyl-2-(2,6-dichlorophenyl)pyrazol-3-yl]methoxy]phenyl]methylamino]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CNCC=2C=CC(OCC=3N(N=CC=3C3CC3)C=3C(=CC=CC=3Cl)Cl)=CC=2)=C1 PNNSHXNLGFOCAJ-UHFFFAOYSA-N 0.000 claims 1
• VYQZBAPNWMTQLG-UHFFFAOYSA-N 3-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(N=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 VYQZBAPNWMTQLG-UHFFFAOYSA-N 0.000 claims 1
• NFEWMKBZBHGQJD-UHFFFAOYSA-N 3-[[n,2-dimethyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]anilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 NFEWMKBZBHGQJD-UHFFFAOYSA-N 0.000 claims 1
• CENNTJAMJCFMBY-UHFFFAOYSA-N 3-butoxy-5-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound OC(=O)C1=CC(OCCCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 CENNTJAMJCFMBY-UHFFFAOYSA-N 0.000 claims 1
• PRXHPULVPUYSCR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-(trifluoromethyl)benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C(F)(F)F)=C1 PRXHPULVPUYSCR-UHFFFAOYSA-N 0.000 claims 1
• IWXHDMNTQMXGJI-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C)=C1 IWXHDMNTQMXGJI-UHFFFAOYSA-N 0.000 claims 1
• YYUPSWNBHVSIQR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-pentylbenzoic acid Chemical compound C1=C(C(O)=O)C(CCCCC)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 YYUPSWNBHVSIQR-UHFFFAOYSA-N 0.000 claims 1
• NSVDMBZEFQUZEO-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-phenylmethoxybenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC(C=1)=CC=C(C(O)=O)C=1OCC1=CC=CC=C1 NSVDMBZEFQUZEO-UHFFFAOYSA-N 0.000 claims 1
• QOTUZOQZTNNEIR-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-propan-2-yloxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(CN(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 QOTUZOQZTNNEIR-UHFFFAOYSA-N 0.000 claims 1
• ZYPVLILUKZRKCD-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-3-hydroxybenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1O ZYPVLILUKZRKCD-UHFFFAOYSA-N 0.000 claims 1
• IEEPTKVPJBRGTH-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 IEEPTKVPJBRGTH-UHFFFAOYSA-N 0.000 claims 1
• RHGRIDMWHLCVGZ-UHFFFAOYSA-N 4-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]-2-pentylbenzoic acid Chemical compound C1=C(C(O)=O)C(CCCCC)=CC(CN(C)C=2C(=NC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3)OC(F)(F)F)=CC=2)C)=C1 RHGRIDMWHLCVGZ-UHFFFAOYSA-N 0.000 claims 1
• RYGDOPNSOPUGDO-UHFFFAOYSA-N 4-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(N=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 RYGDOPNSOPUGDO-UHFFFAOYSA-N 0.000 claims 1
• UXRMSUBAWLOIKL-UHFFFAOYSA-N 4-[[n,2-dimethyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]anilino]methyl]-2-methylbenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C(C)=C1 UXRMSUBAWLOIKL-UHFFFAOYSA-N 0.000 claims 1
• OMCYUGSEGWFIEN-UHFFFAOYSA-N 4-[[n,2-dimethyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]anilino]methyl]benzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 OMCYUGSEGWFIEN-UHFFFAOYSA-N 0.000 claims 1
• NEXRZLRNZNTMOZ-UHFFFAOYSA-N 4-methyl-2-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]-1,3-thiazole-5-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1C1=NC(C)=C(C(O)=O)S1 NEXRZLRNZNTMOZ-UHFFFAOYSA-N 0.000 claims 1
• ZLSHXKXFGGKERO-UHFFFAOYSA-N 5-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]thiophene-2-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1C1=CC=C(C(O)=O)S1 ZLSHXKXFGGKERO-UHFFFAOYSA-N 0.000 claims 1
• GECYOKBCGOQDRO-UHFFFAOYSA-N 5-[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methylphenyl]thiophene-2-carboxylic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1C1=CC=C(C(O)=O)S1 GECYOKBCGOQDRO-UHFFFAOYSA-N 0.000 claims 1
• JZMNRJPITYPLOG-UHFFFAOYSA-N 5-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-fluorobenzoic acid Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(F)C(C(O)=O)=C1 JZMNRJPITYPLOG-UHFFFAOYSA-N 0.000 claims 1
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• VJPVESOWUMXSCN-UHFFFAOYSA-N ethyl 3-(dimethylaminomethylidene)-4-methyl-2-oxopentanoate Chemical compound CCOC(=O)C(=O)C(C(C)C)=CN(C)C VJPVESOWUMXSCN-UHFFFAOYSA-N 0.000 description 2
• NSTNXLNCIUDOKF-UHFFFAOYSA-N ethyl 3-[(4-hydroxy-2-methylphenyl)methylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NCC=2C(=CC(O)=CC=2)C)=C1 NSTNXLNCIUDOKF-UHFFFAOYSA-N 0.000 description 2
• YEKYFGBKBPJUFL-UHFFFAOYSA-N ethyl 3-cyclobutyl-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1CCC1 YEKYFGBKBPJUFL-UHFFFAOYSA-N 0.000 description 2
• WAHQCERRHFAQHG-UHFFFAOYSA-N ethyl 4-(3-methoxyphenyl)sulfanyl-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CSC1=CC=CC(OC)=C1 WAHQCERRHFAQHG-UHFFFAOYSA-N 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 230000007717 exclusion Effects 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 238000003304 gavage Methods 0.000 description 2
• 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 2
• PUYCICVJCRLABY-UHFFFAOYSA-N heptane;oxolane Chemical compound C1CCOC1.CCCCCCC PUYCICVJCRLABY-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 239000013067 intermediate product Substances 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 238000004811 liquid chromatography Methods 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
• 239000012139 lysis buffer Substances 0.000 description 2
• VONGYFFEWFJHNP-UHFFFAOYSA-N methyl 1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 2
• YCFUSIDKEYANIW-UHFFFAOYSA-N methyl 2,3-difluoro-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(F)=C1F YCFUSIDKEYANIW-UHFFFAOYSA-N 0.000 description 2
• KZIQXLCAEUTYPY-UHFFFAOYSA-N methyl 2-[4-(bromomethyl)phenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=C(CBr)C=C1 KZIQXLCAEUTYPY-UHFFFAOYSA-N 0.000 description 2
• RIVBHQXMRWUXSI-UHFFFAOYSA-N methyl 2-bromo-4-(hydroxymethyl)benzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1Br RIVBHQXMRWUXSI-UHFFFAOYSA-N 0.000 description 2
• DJTUYAFJAGLQCK-UHFFFAOYSA-N methyl 2-bromo-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1Br DJTUYAFJAGLQCK-UHFFFAOYSA-N 0.000 description 2
• LTIHOWCLTSRYGS-UHFFFAOYSA-N methyl 2-fluoro-4-(4-hydroxy-2-methylphenyl)benzoate Chemical compound C1=C(F)C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C LTIHOWCLTSRYGS-UHFFFAOYSA-N 0.000 description 2
• AEQBQMUJJMQZFW-UHFFFAOYSA-N methyl 2-methyl-2-(4-methylphenyl)propanoate Chemical compound COC(=O)C(C)(C)C1=CC=C(C)C=C1 AEQBQMUJJMQZFW-UHFFFAOYSA-N 0.000 description 2
• BVLZMHRTGRUAKZ-UHFFFAOYSA-N methyl 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=C(C)OC2=CC=1B1OC(C)(C)C(C)(C)O1 BVLZMHRTGRUAKZ-UHFFFAOYSA-N 0.000 description 2
• IHXXYBKSTSUCGT-UHFFFAOYSA-N methyl 2-methyl-6-(trifluoromethylsulfonyloxy)-1-benzofuran-3-carboxylate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=C2C(C(=O)OC)=C(C)OC2=C1 IHXXYBKSTSUCGT-UHFFFAOYSA-N 0.000 description 2
• JWLLHJGGRZGJHB-UHFFFAOYSA-N methyl 3-(2-methoxyethenyl)benzoate Chemical compound COC=CC1=CC=CC(C(=O)OC)=C1 JWLLHJGGRZGJHB-UHFFFAOYSA-N 0.000 description 2
• IWZQJSPPSISZEC-UHFFFAOYSA-N methyl 3-[1-[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methylphenyl]ethylsulfanyl]benzoate Chemical compound COC(=O)C1=CC=CC(SC(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 IWZQJSPPSISZEC-UHFFFAOYSA-N 0.000 description 2
• NYEHKJYWMUGBFY-UHFFFAOYSA-N methyl 4-(2-methoxyethenyl)benzoate Chemical compound COC=CC1=CC=C(C(=O)OC)C=C1 NYEHKJYWMUGBFY-UHFFFAOYSA-N 0.000 description 2
• KOPJXWORERXNRW-UHFFFAOYSA-N methyl 4-(4-hydroxy-2-methylphenyl)-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C KOPJXWORERXNRW-UHFFFAOYSA-N 0.000 description 2
• DCXFLSHDURQRML-UHFFFAOYSA-N methyl 4-(bromomethyl)-2-methoxybenzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1OC DCXFLSHDURQRML-UHFFFAOYSA-N 0.000 description 2
• USAPRVQCMANWFG-UHFFFAOYSA-N methyl 4-[(2-chloro-4-hydroxyanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CNC1=CC=C(O)C=C1Cl USAPRVQCMANWFG-UHFFFAOYSA-N 0.000 description 2
• WXCLPAPFMVVTOX-UHFFFAOYSA-N methyl 4-[(2-fluoro-4-hydroxy-n-methylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1F WXCLPAPFMVVTOX-UHFFFAOYSA-N 0.000 description 2
• GNEADNFRBXZVDG-UHFFFAOYSA-N methyl 4-[(2-fluoro-4-hydroxyanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CNC1=CC=C(O)C=C1F GNEADNFRBXZVDG-UHFFFAOYSA-N 0.000 description 2
• YCPAENNGFUONNL-UHFFFAOYSA-N methyl 4-[[4-[[4-cyclopropyl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]-2-propan-2-yloxybenzoate Chemical compound C1=C(OC(C)C)C(C(=O)OC)=CC=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C2CC2)C=NN1C1=CC=CC=C1OC(F)(F)F YCPAENNGFUONNL-UHFFFAOYSA-N 0.000 description 2
• LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 2
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• NRCUDUNFYQHVLK-UHFFFAOYSA-N methyl 4-methyl-2-prop-2-enylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1CC=C NRCUDUNFYQHVLK-UHFFFAOYSA-N 0.000 description 2
• XTQJPWKPUVJCHF-UHFFFAOYSA-N methyl 4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazole-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F XTQJPWKPUVJCHF-UHFFFAOYSA-N 0.000 description 2
• AALWVKQRLXHHRT-UHFFFAOYSA-N methyl 5-(4-methoxy-2-methylphenyl)-4-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C)=C1C1=CC=C(OC)C=C1C AALWVKQRLXHHRT-UHFFFAOYSA-N 0.000 description 2
• MFOKOKHNSVUKON-UHFFFAOYSA-N methyl 5-bromo-1H-indole-3-carboxylate Natural products C1=C(Br)C=C2C(C(=O)OC)=CNC2=C1 MFOKOKHNSVUKON-UHFFFAOYSA-N 0.000 description 2
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• 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 2
• HVSAEJIBGMVUJK-UHFFFAOYSA-N methyl 6-bromo-1-propan-2-ylindole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=CN(C(C)C)C2=C1 HVSAEJIBGMVUJK-UHFFFAOYSA-N 0.000 description 2
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• KHXUTOLCCFWPDH-UHFFFAOYSA-N methyl 2-(4-bromo-2-nitrophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Br)C=C1[N+]([O-])=O KHXUTOLCCFWPDH-UHFFFAOYSA-N 0.000 description 1
• JMHGPQXQCHSCGN-UHFFFAOYSA-N methyl 2-(4-formylphenyl)-2-methylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=C(C=O)C=C1 JMHGPQXQCHSCGN-UHFFFAOYSA-N 0.000 description 1
• ZELDTJAAMDIHDY-UHFFFAOYSA-N methyl 2-(4-hydroxy-2-methylphenyl)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OC)SC(C=2C(=CC(O)=CC=2)C)=N1 ZELDTJAAMDIHDY-UHFFFAOYSA-N 0.000 description 1
• USOHUXMHLGFRHW-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)-1-benzothiophene-6-carboxylate Chemical compound S1C2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(O)C=C1 USOHUXMHLGFRHW-UHFFFAOYSA-N 0.000 description 1
• DDTWPJUKVPLVTL-UHFFFAOYSA-N methyl 2-(4-methoxyphenyl)-1-benzothiophene-6-carboxylate Chemical compound S1C2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(OC)C=C1 DDTWPJUKVPLVTL-UHFFFAOYSA-N 0.000 description 1
• NVQIKIDABBHFGT-UHFFFAOYSA-N methyl 2-(4-sulfanylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(S)C=C1 NVQIKIDABBHFGT-UHFFFAOYSA-N 0.000 description 1
• SSWHBDSYYMBTKI-UHFFFAOYSA-N methyl 2-(5-bromo-1h-indol-3-yl)acetate Chemical compound C1=C(Br)C=C2C(CC(=O)OC)=CNC2=C1 SSWHBDSYYMBTKI-UHFFFAOYSA-N 0.000 description 1
• FVLAQXLXLDPMDI-UHFFFAOYSA-N methyl 2-(butanoylamino)-4-(hydroxymethyl)benzoate Chemical compound CCCC(=O)NC1=CC(CO)=CC=C1C(=O)OC FVLAQXLXLDPMDI-UHFFFAOYSA-N 0.000 description 1
• ONRUOMROKJZAIQ-UHFFFAOYSA-N methyl 2-(butanoylamino)-4-formylbenzoate Chemical compound CCCC(=O)NC1=CC(C=O)=CC=C1C(=O)OC ONRUOMROKJZAIQ-UHFFFAOYSA-N 0.000 description 1
• FPSBVFVXCAKBSN-UHFFFAOYSA-N methyl 2-(butanoylamino)-4-methylbenzoate Chemical compound CCCC(=O)NC1=CC(C)=CC=C1C(=O)OC FPSBVFVXCAKBSN-UHFFFAOYSA-N 0.000 description 1
• WDQKWLOSGFSNQW-UHFFFAOYSA-N methyl 2-[2-chloro-6-(trifluoromethyl)phenyl]-4-propan-2-ylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1C(F)(F)F WDQKWLOSGFSNQW-UHFFFAOYSA-N 0.000 description 1
• ZIHNLAQBEBEMFE-UHFFFAOYSA-N methyl 2-[2-fluoro-6-(trifluoromethyl)phenyl]-4-propan-2-ylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)C=NN1C1=C(F)C=CC=C1C(F)(F)F ZIHNLAQBEBEMFE-UHFFFAOYSA-N 0.000 description 1
• RCGDPBQRRUOJSD-UHFFFAOYSA-N methyl 2-[3,5-difluoro-2-(trifluoromethyl)phenyl]-4-propan-2-ylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)C=NN1C1=CC(F)=CC(F)=C1C(F)(F)F RCGDPBQRRUOJSD-UHFFFAOYSA-N 0.000 description 1
• FWKUWWTUGPFARL-UHFFFAOYSA-N methyl 2-[4-(4-hydroxy-2-methylphenyl)phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1C1=CC=C(O)C=C1C FWKUWWTUGPFARL-UHFFFAOYSA-N 0.000 description 1
• APXOMRFLJBRHNX-UHFFFAOYSA-N methyl 2-[4-(bromomethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=C(CBr)C=C1 APXOMRFLJBRHNX-UHFFFAOYSA-N 0.000 description 1
• FNLZPQBOAYFUFR-UHFFFAOYSA-N methyl 2-[4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1CN(C)C(C(=C1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl FNLZPQBOAYFUFR-UHFFFAOYSA-N 0.000 description 1
• XFHXPFCCIGVOES-UHFFFAOYSA-N methyl 2-[5-(4-hydroxy-2-methylphenyl)-1h-indol-3-yl]acetate Chemical compound C1=C2C(CC(=O)OC)=CNC2=CC=C1C1=CC=C(O)C=C1C XFHXPFCCIGVOES-UHFFFAOYSA-N 0.000 description 1
• MXCORZGOCXMLPH-UHFFFAOYSA-N methyl 2-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzothiophen-3-yl]acetate Chemical compound C=1C=C2C(CC(=O)OC)=CSC2=CC=1B1OC(C)(C)C(C)(C)O1 MXCORZGOCXMLPH-UHFFFAOYSA-N 0.000 description 1
• SHZZCYREFYGRNZ-UHFFFAOYSA-N methyl 2-benzoyl-4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1C(=O)C1=CC=CC=C1 SHZZCYREFYGRNZ-UHFFFAOYSA-N 0.000 description 1
• SICUPTLSTAURTC-UHFFFAOYSA-N methyl 2-benzoyl-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1C(=O)C1=CC=CC=C1 SICUPTLSTAURTC-UHFFFAOYSA-N 0.000 description 1
• ORHVRAHCCKRMAF-UHFFFAOYSA-N methyl 2-bromo-1-benzothiophene-3-carboxylate Chemical compound COC(=O)C1=C(SC2=C1C=CC=C2)Br ORHVRAHCCKRMAF-UHFFFAOYSA-N 0.000 description 1
• ZTDXOVAPGGNGSD-UHFFFAOYSA-N methyl 2-bromo-4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1Br ZTDXOVAPGGNGSD-UHFFFAOYSA-N 0.000 description 1
• VRTQLDFCPNVQNT-UHFFFAOYSA-N methyl 2-bromo-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1Br VRTQLDFCPNVQNT-UHFFFAOYSA-N 0.000 description 1
• DSYLZQPIJVFYBP-UHFFFAOYSA-N methyl 2-butoxy-4-(hydroxymethyl)benzoate Chemical compound CCCCOC1=CC(CO)=CC=C1C(=O)OC DSYLZQPIJVFYBP-UHFFFAOYSA-N 0.000 description 1
• DNMOLHRZGOTBED-UHFFFAOYSA-N methyl 2-butoxy-4-[(4-hydroxy-n,2-dimethylanilino)methyl]benzoate Chemical compound C1=C(C(=O)OC)C(OCCCC)=CC(CN(C)C=2C(=CC(O)=CC=2)C)=C1 DNMOLHRZGOTBED-UHFFFAOYSA-N 0.000 description 1
• VXQZIUJCGSIQEL-UHFFFAOYSA-N methyl 2-butoxy-4-[[4-[tert-butyl(dimethyl)silyl]oxy-n,2-dimethylanilino]methyl]benzoate Chemical compound C1=C(C(=O)OC)C(OCCCC)=CC(CN(C)C=2C(=CC(O[Si](C)(C)C(C)(C)C)=CC=2)C)=C1 VXQZIUJCGSIQEL-UHFFFAOYSA-N 0.000 description 1
• FIKBYSIYPIRVFD-UHFFFAOYSA-N methyl 2-butoxy-4-formylbenzoate Chemical compound CCCCOC1=CC(C=O)=CC=C1C(=O)OC FIKBYSIYPIRVFD-UHFFFAOYSA-N 0.000 description 1
• FSQOQFQTZISUJL-UHFFFAOYSA-N methyl 2-butoxy-4-methylbenzoate Chemical compound CCCCOC1=CC(C)=CC=C1C(=O)OC FSQOQFQTZISUJL-UHFFFAOYSA-N 0.000 description 1
• HEUCCNBDPMIQOO-UHFFFAOYSA-N methyl 2-butoxy-5-(2-oxoethyl)benzoate Chemical compound CCCCOC1=CC=C(CC=O)C=C1C(=O)OC HEUCCNBDPMIQOO-UHFFFAOYSA-N 0.000 description 1
• WHGPOEHVTUKTIX-UHFFFAOYSA-N methyl 2-butoxy-5-methylbenzoate Chemical compound CCCCOC1=CC=C(C)C=C1C(=O)OC WHGPOEHVTUKTIX-UHFFFAOYSA-N 0.000 description 1
• HQCXKXPONVJZBV-UHFFFAOYSA-N methyl 2-chloro-4-(4-hydroxy-2-methylphenyl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C HQCXKXPONVJZBV-UHFFFAOYSA-N 0.000 description 1
• XVMRTAJYFLOFOG-UHFFFAOYSA-N methyl 2-fluoro-5-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC(CC=O)=CC=C1F XVMRTAJYFLOFOG-UHFFFAOYSA-N 0.000 description 1
• UITFCFWKYAOJEJ-UHFFFAOYSA-N methyl 2-hydroxy-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1O UITFCFWKYAOJEJ-UHFFFAOYSA-N 0.000 description 1
• WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 1
• ZECXBDQLXINILP-UHFFFAOYSA-N methyl 3-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CC=O)=C1 ZECXBDQLXINILP-UHFFFAOYSA-N 0.000 description 1
• LOYWLECAZBDCSU-UHFFFAOYSA-N methyl 3-(bromomethyl)-5-methylbenzoate Chemical compound COC(=O)C1=CC(C)=CC(CBr)=C1 LOYWLECAZBDCSU-UHFFFAOYSA-N 0.000 description 1
• VDBHABWBYGEHFE-UHFFFAOYSA-N methyl 3-(hydroxymethyl)-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(CO)=CC(C(F)(F)F)=C1 VDBHABWBYGEHFE-UHFFFAOYSA-N 0.000 description 1
• SVKLHAXESBIPNF-UHFFFAOYSA-N methyl 3-[2-(2-chloro-4-hydroxyphenyl)ethenyl]benzoate Chemical compound COC(=O)C1=CC=CC(C=CC=2C(=CC(O)=CC=2)Cl)=C1 SVKLHAXESBIPNF-UHFFFAOYSA-N 0.000 description 1
• UDNOIRKUBPWPHF-UHFFFAOYSA-N methyl 3-[2-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]methoxy]phenyl]ethenyl]benzoate Chemical compound COC(=O)C1=CC=CC(C=CC=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3)C(F)(F)F)=CC=2)C)=C1 UDNOIRKUBPWPHF-UHFFFAOYSA-N 0.000 description 1
• DYQAAMRZMHVBNW-UHFFFAOYSA-N methyl 3-[2-[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methylphenyl]propan-2-ylsulfanyl]benzoate Chemical compound COC(=O)C1=CC=CC(SC(C)(C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 DYQAAMRZMHVBNW-UHFFFAOYSA-N 0.000 description 1
• LMXAEAUMBUAFOL-UHFFFAOYSA-N methyl 3-[3-(4-hydroxy-2-methylphenyl)phenyl]propanoate Chemical compound COC(=O)CCC1=CC=CC(C=2C(=CC(O)=CC=2)C)=C1 LMXAEAUMBUAFOL-UHFFFAOYSA-N 0.000 description 1
• AJAIFLFVMXERDD-UHFFFAOYSA-N methyl 3-[4-(4-hydroxy-2-methylphenyl)phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OC)=CC=C1C1=CC=C(O)C=C1C AJAIFLFVMXERDD-UHFFFAOYSA-N 0.000 description 1
• LAOPQGYDUZCDMD-UHFFFAOYSA-N methyl 3-[4-[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methylphenyl]phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OC)=CC=C1C(C(=C1)C)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl LAOPQGYDUZCDMD-UHFFFAOYSA-N 0.000 description 1
• YIVMKZJJRPCBMA-UHFFFAOYSA-N methyl 3-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methyl-n-[(2-methylpropan-2-yl)oxycarbonyl]anilino]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN(C(=O)OC(C)(C)C)C=2C(=CC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 YIVMKZJJRPCBMA-UHFFFAOYSA-N 0.000 description 1
• PMRQTVRYDUKICZ-UHFFFAOYSA-N methyl 3-[[methyl-[2-methyl-6-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]pyridin-3-yl]amino]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN(C)C=2C(=NC(OCC=3N(N=CC=3C(C)C)C=3C(=CC=CC=3)OC(F)(F)F)=CC=2)C)=C1 PMRQTVRYDUKICZ-UHFFFAOYSA-N 0.000 description 1
• XFONNRDVFHFOGX-UHFFFAOYSA-N methyl 3-bromo-1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2C(Br)=C(C(=O)OC)SC2=C1 XFONNRDVFHFOGX-UHFFFAOYSA-N 0.000 description 1
• RKUNSPWAQIUGEZ-UHFFFAOYSA-N methyl 3-bromo-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(Br)=C1 RKUNSPWAQIUGEZ-UHFFFAOYSA-N 0.000 description 1
• MBKUHNGECMPIHH-UHFFFAOYSA-N methyl 3-ethenylbenzoate Chemical compound COC(=O)C1=CC=CC(C=C)=C1 MBKUHNGECMPIHH-UHFFFAOYSA-N 0.000 description 1
• KMHCSCDCZHSSOQ-UHFFFAOYSA-N methyl 3-formamido-4-formylbenzoate methyl 1H-indole-6-carboxylate Chemical compound N1C=CC2=CC=C(C=C12)C(=O)OC.COC(C1=CC(=C(C=C1)C=O)NC=O)=O KMHCSCDCZHSSOQ-UHFFFAOYSA-N 0.000 description 1
• YFEHZLHUOABJFH-UHFFFAOYSA-N methyl 3-formyl-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(C=O)=CC(C(F)(F)F)=C1 YFEHZLHUOABJFH-UHFFFAOYSA-N 0.000 description 1
• UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 1
• SRGOMBXXNIVIPR-UHFFFAOYSA-N methyl 3-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC(S)=C1 SRGOMBXXNIVIPR-UHFFFAOYSA-N 0.000 description 1
• SJVMXEXEYBEEHK-UHFFFAOYSA-N methyl 4-(2-bromo-4-methoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1Br SJVMXEXEYBEEHK-UHFFFAOYSA-N 0.000 description 1
• HKTGGDULWDLYKQ-UHFFFAOYSA-N methyl 4-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=C(CC=O)C=C1 HKTGGDULWDLYKQ-UHFFFAOYSA-N 0.000 description 1
• IXBJTIISONCRCS-UHFFFAOYSA-N methyl 4-(4-hydroxy-2-methylphenyl)-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C IXBJTIISONCRCS-UHFFFAOYSA-N 0.000 description 1
• AVSYCCCSEGFTDG-UHFFFAOYSA-N methyl 4-(4-hydroxy-2-methylphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C AVSYCCCSEGFTDG-UHFFFAOYSA-N 0.000 description 1
• WSZFWZXVFBXDCO-UHFFFAOYSA-N methyl 4-(4h-1,3-dioxin-2-yl)-2-pentylbenzoate Chemical compound C1=C(C(=O)OC)C(CCCCC)=CC(C2OC=CCO2)=C1 WSZFWZXVFBXDCO-UHFFFAOYSA-N 0.000 description 1
• DKTXXBLWUUYFNL-UHFFFAOYSA-N methyl 4-(bromomethyl)-2,3-difluorobenzoate Chemical compound COC(=O)C1=CC=C(CBr)C(F)=C1F DKTXXBLWUUYFNL-UHFFFAOYSA-N 0.000 description 1
• CSPFYVKDMLBOIW-UHFFFAOYSA-N methyl 4-(bromomethyl)-2-(butanoylamino)benzoate Chemical compound CCCC(=O)NC1=CC(CBr)=CC=C1C(=O)OC CSPFYVKDMLBOIW-UHFFFAOYSA-N 0.000 description 1
• JWDNUUUNFLHOPB-UHFFFAOYSA-N methyl 4-(bromomethyl)-2-(propylsulfonylamino)benzoate Chemical compound CCCS(=O)(=O)NC1=CC(CBr)=CC=C1C(=O)OC JWDNUUUNFLHOPB-UHFFFAOYSA-N 0.000 description 1
• JTOJTFMOZMCZKU-UHFFFAOYSA-N methyl 4-(bromomethyl)-2-butoxybenzoate Chemical compound CCCCOC1=CC(CBr)=CC=C1C(=O)OC JTOJTFMOZMCZKU-UHFFFAOYSA-N 0.000 description 1
• LXXRFFAIWGWJMA-UHFFFAOYSA-N methyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C(C(F)(F)F)=C1 LXXRFFAIWGWJMA-UHFFFAOYSA-N 0.000 description 1
• NZZLGVIQLWHWCI-UHFFFAOYSA-N methyl 4-(bromomethyl)naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=C(CBr)C2=C1 NZZLGVIQLWHWCI-UHFFFAOYSA-N 0.000 description 1
• IKVYKIJFJHJGIN-UHFFFAOYSA-N methyl 4-(hydroxymethyl)-2-(propylsulfonylamino)benzoate Chemical compound CCCS(=O)(=O)NC1=CC(CO)=CC=C1C(=O)OC IKVYKIJFJHJGIN-UHFFFAOYSA-N 0.000 description 1
• RUDDPYMBSUULPV-UHFFFAOYSA-N methyl 4-(hydroxymethyl)-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1C(F)(F)F RUDDPYMBSUULPV-UHFFFAOYSA-N 0.000 description 1
• MKDRMEUNIJXIBA-UHFFFAOYSA-N methyl 4-(hydroxymethyl)-2-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1OCC1=CC=CC=C1 MKDRMEUNIJXIBA-UHFFFAOYSA-N 0.000 description 1
• ANTWEBPUXREIBG-UHFFFAOYSA-N methyl 4-[(2-chloro-4-hydroxy-n-methylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1Cl ANTWEBPUXREIBG-UHFFFAOYSA-N 0.000 description 1
• MFHUCPZYAVDHEI-UHFFFAOYSA-N methyl 4-[(2-fluoro-4-hydroxy-n,6-dimethylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=C(C)C=C(O)C=C1F MFHUCPZYAVDHEI-UHFFFAOYSA-N 0.000 description 1
• WEKDWRRJMSBWOK-UHFFFAOYSA-N methyl 4-[(4-hydroxy-2-methylphenyl)methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NCC1=CC=C(O)C=C1C WEKDWRRJMSBWOK-UHFFFAOYSA-N 0.000 description 1
• ARFIARSKKJAKGN-UHFFFAOYSA-N methyl 4-[(4-hydroxy-n,2-dimethylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1C ARFIARSKKJAKGN-UHFFFAOYSA-N 0.000 description 1
• CHVIOJWBENKHKS-UHFFFAOYSA-N methyl 4-[(4-hydroxy-n-methylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1 CHVIOJWBENKHKS-UHFFFAOYSA-N 0.000 description 1
• NFSVMTAZTWUULJ-UHFFFAOYSA-N methyl 4-[(4-hydroxyanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CNC1=CC=C(O)C=C1 NFSVMTAZTWUULJ-UHFFFAOYSA-N 0.000 description 1
• DFYNXSRKCVNRSO-UHFFFAOYSA-N methyl 4-[1-(4-hydroxy-2-methylphenyl)ethylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(C)C1=CC=C(O)C=C1C DFYNXSRKCVNRSO-UHFFFAOYSA-N 0.000 description 1
• CZBLJGKTYIWHSV-UHFFFAOYSA-N methyl 4-[[2-fluoro-n,6-dimethyl-4-tri(propan-2-yl)silyloxyanilino]methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=C(C)C=C(O[Si](C(C)C)(C(C)C)C(C)C)C=C1F CZBLJGKTYIWHSV-UHFFFAOYSA-N 0.000 description 1
• DLILIUSWDLJMCE-UHFFFAOYSA-N methyl 4-bromo-2-fluorobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1F DLILIUSWDLJMCE-UHFFFAOYSA-N 0.000 description 1
• RVNNYZMXLLTRBZ-UHFFFAOYSA-N methyl 4-butoxy-3-(2-oxoethyl)benzoate Chemical compound CCCCOC1=CC=C(C(=O)OC)C=C1CC=O RVNNYZMXLLTRBZ-UHFFFAOYSA-N 0.000 description 1
• BHFZMFQMTKSOIW-UHFFFAOYSA-N methyl 4-fluoro-2-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=C(F)C=C1CC=O BHFZMFQMTKSOIW-UHFFFAOYSA-N 0.000 description 1
• BJQTVTQFFBEZIS-UHFFFAOYSA-N methyl 4-fluoro-3-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=C(F)C(CC=O)=C1 BJQTVTQFFBEZIS-UHFFFAOYSA-N 0.000 description 1
• MFMRJPYWXWEKHT-UHFFFAOYSA-N methyl 4-formyl-2-(propylsulfonylamino)benzoate Chemical compound CCCS(=O)(=O)NC1=CC(C=O)=CC=C1C(=O)OC MFMRJPYWXWEKHT-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
• SYHVSQLPWXOXEL-UHFFFAOYSA-N methyl 4-formyl-2-pent-1-ynylbenzoate Chemical compound CCCC#CC1=CC(C=O)=CC=C1C(=O)OC SYHVSQLPWXOXEL-UHFFFAOYSA-N 0.000 description 1
• DLRIPFRLOJLVOL-UHFFFAOYSA-N methyl 4-formyl-2-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1OCC1=CC=CC=C1 DLRIPFRLOJLVOL-UHFFFAOYSA-N 0.000 description 1
• GARIEFYANPKBAU-UHFFFAOYSA-N methyl 4-iodo-3-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC=C(I)C(OCC=2C=CC=CC=2)=C1 GARIEFYANPKBAU-UHFFFAOYSA-N 0.000 description 1
• PMSZMWGSTQBAEI-UHFFFAOYSA-N methyl 4-methyl-2-(propylsulfonylamino)benzoate Chemical compound CCCS(=O)(=O)NC1=CC(C)=CC=C1C(=O)OC PMSZMWGSTQBAEI-UHFFFAOYSA-N 0.000 description 1
• LFVDEVQENPHSSD-UHFFFAOYSA-N methyl 4-methyl-2-oxopentanoate Chemical compound COC(=O)C(=O)CC(C)C LFVDEVQENPHSSD-UHFFFAOYSA-N 0.000 description 1
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• JXIFTJPLXDAQGY-UHFFFAOYSA-N methyl 5-(4-hydroxy-2-methylphenyl)-1h-indole-3-carboxylate Chemical compound C1=C2C(C(=O)OC)=CNC2=CC=C1C1=CC=C(O)C=C1C JXIFTJPLXDAQGY-UHFFFAOYSA-N 0.000 description 1
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