BRPI0712262A2 - agonistas de fxr - Google Patents
agonistas de fxr Download PDFInfo
- Publication number
- BRPI0712262A2 BRPI0712262A2 BRPI0712262-4A BRPI0712262A BRPI0712262A2 BR PI0712262 A2 BRPI0712262 A2 BR PI0712262A2 BR PI0712262 A BRPI0712262 A BR PI0712262A BR PI0712262 A2 BRPI0712262 A2 BR PI0712262A2
- Authority
- BR
- Brazil
- Prior art keywords
- methyl
- phenyl
- isopropyl
- hydrogen
- pyrazol
- Prior art date
Links
- 239000000556 agonist Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 322
- 238000000034 method Methods 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 16
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 benzoisoxazoyl Chemical group 0.000 claims description 207
- 229910052739 hydrogen Inorganic materials 0.000 claims description 152
- 239000001257 hydrogen Substances 0.000 claims description 147
- 239000000460 chlorine Substances 0.000 claims description 74
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 229910052801 chlorine Inorganic materials 0.000 claims description 55
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 54
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 51
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 36
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 32
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 21
- 239000005711 Benzoic acid Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 19
- 125000001041 indolyl group Chemical group 0.000 claims description 19
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 6
- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 150000003626 triacylglycerols Chemical class 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 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 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
- 238000008214 LDL Cholesterol Methods 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 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
- 150000002431 hydrogen Chemical class 0.000 claims 32
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 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
- 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
- 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
- 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
- DLJPTDRKSOMUBW-UHFFFAOYSA-N 4-[[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylanilino]methyl]naphthalene-1-carboxylic acid Chemical compound C=1C=C(N(C)CC=2C3=CC=CC=C3C(C(O)=O)=CC=2)C(C)=CC=1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl DLJPTDRKSOMUBW-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
- 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
- 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
- MBCMEMRMRKGJNN-UHFFFAOYSA-N 6-[2-methyl-4-[[4-propan-2-yl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]phenyl]-1-benzothiophene-3-carboxylic acid Chemical compound C=1C=C(C=2C=C3SC=C(C3=CC=2)C(O)=O)C(C)=CC=1OCC1=C(C(C)C)C=NN1C1=CC=CC=C1OC(F)(F)F MBCMEMRMRKGJNN-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 524
- 238000002360 preparation method Methods 0.000 description 333
- 235000019439 ethyl acetate Nutrition 0.000 description 210
- 239000000203 mixture Substances 0.000 description 207
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 187
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 176
- 239000000243 solution Substances 0.000 description 170
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 139
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 131
- 239000011541 reaction mixture Substances 0.000 description 120
- 238000006243 chemical reaction Methods 0.000 description 116
- 230000002829 reductive effect Effects 0.000 description 103
- 238000005160 1H NMR spectroscopy Methods 0.000 description 100
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
- 239000012044 organic layer Substances 0.000 description 81
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
- 239000012267 brine Substances 0.000 description 69
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 239000007787 solid Substances 0.000 description 61
- 239000010410 layer Substances 0.000 description 60
- 238000003818 flash chromatography Methods 0.000 description 59
- 239000007858 starting material Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 239000011734 sodium Substances 0.000 description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 39
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 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 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
- 235000019341 magnesium sulphate Nutrition 0.000 description 29
- 150000004702 methyl esters Chemical class 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 235000012000 cholesterol Nutrition 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 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 14
- 235000011181 potassium carbonates Nutrition 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- XZXKGSCMQKHARC-UHFFFAOYSA-N dimethyl 5-butoxybenzene-1,3-dicarboxylate Chemical compound CCCCOC1=CC(C(=O)OC)=CC(C(=O)OC)=C1 XZXKGSCMQKHARC-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- CRHWEIDCXNDTMO-UHFFFAOYSA-N ditert-butylphosphane Chemical compound CC(C)(C)PC(C)(C)C CRHWEIDCXNDTMO-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- ANEDZEVDORCLPM-UHFFFAOYSA-N ethyl 1,3-dithiane-2-carboxylate Chemical compound CCOC(=O)C1SCCCS1 ANEDZEVDORCLPM-UHFFFAOYSA-N 0.000 description 1
- KVTZSCYPOQMXTO-UHFFFAOYSA-N ethyl 1-benzothiophene-7-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1SC=C2 KVTZSCYPOQMXTO-UHFFFAOYSA-N 0.000 description 1
- OYQVQWIASIXXRT-UHFFFAOYSA-N ethyl 2,4-dioxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)=O OYQVQWIASIXXRT-UHFFFAOYSA-N 0.000 description 1
- IYUJSDLNZRVUND-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-methylphenyl)-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OCC)=CN=C1C1=CC=C(O)C=C1C IYUJSDLNZRVUND-UHFFFAOYSA-N 0.000 description 1
- HHFXANRCFLCNJW-UHFFFAOYSA-N ethyl 2-(4-methoxy-2-methylphenyl)-1-benzothiophene-5-carboxylate Chemical compound C=1C2=CC(C(=O)OCC)=CC=C2SC=1C1=CC=C(OC)C=C1C HHFXANRCFLCNJW-UHFFFAOYSA-N 0.000 description 1
- XGOWYXHVRJISDX-UHFFFAOYSA-N ethyl 2-(6-hydroxy-1-benzothiophen-3-yl)acetate Chemical compound OC1=CC=C2C(CC(=O)OCC)=CSC2=C1 XGOWYXHVRJISDX-UHFFFAOYSA-N 0.000 description 1
- HGGCGFRYUUGPFG-UHFFFAOYSA-N ethyl 2-(6-methoxy-1-benzothiophen-3-yl)acetate Chemical compound COC1=CC=C2C(CC(=O)OCC)=CSC2=C1 HGGCGFRYUUGPFG-UHFFFAOYSA-N 0.000 description 1
- GSBNBIUKZHQMJQ-UHFFFAOYSA-N ethyl 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)OCC)=CSC2=CC=1B1OC(C)(C)C(C)(C)O1 GSBNBIUKZHQMJQ-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- HDMJBDNQNKWAHU-UHFFFAOYSA-N ethyl 2-methoxyimino-4-oxopentanoate Chemical compound CCOC(=O)C(CC(C)=O)=NOC HDMJBDNQNKWAHU-UHFFFAOYSA-N 0.000 description 1
- KANJMAYCVZVTER-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2C=CC(O)=CC=2)=C1 KANJMAYCVZVTER-UHFFFAOYSA-N 0.000 description 1
- OMGLLHZYCHTOJE-UHFFFAOYSA-N ethyl 3-(4-phenylmethoxyphenyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1 OMGLLHZYCHTOJE-UHFFFAOYSA-N 0.000 description 1
- XMPYEWCBWRELII-UHFFFAOYSA-N ethyl 3-bromo-4-(hydroxymethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CO)C(Br)=C1 XMPYEWCBWRELII-UHFFFAOYSA-N 0.000 description 1
- YEKYFGBKBPJUFL-UHFFFAOYSA-N ethyl 3-cyclobutyl-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1CCC1 YEKYFGBKBPJUFL-UHFFFAOYSA-N 0.000 description 1
- AXZYLOKPPDEQJP-UHFFFAOYSA-N ethyl 3-cyclobutyl-4-(dimethylamino)-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C(=CN(C)C)C1CCC1 AXZYLOKPPDEQJP-UHFFFAOYSA-N 0.000 description 1
- POGCXCWRMMXDAQ-UHFFFAOYSA-N ethyl 3-iodobenzoate Chemical compound CCOC(=O)C1=CC=CC(I)=C1 POGCXCWRMMXDAQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PCSAOKNUAJNUEO-UHFFFAOYSA-N ethyl 4-cyclobutyl-2-(2,6-dichlorophenyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=C(C2CCC2)C=NN1C1=C(Cl)C=CC=C1Cl PCSAOKNUAJNUEO-UHFFFAOYSA-N 0.000 description 1
- CNMNZKPHJJSIBH-UHFFFAOYSA-N ethyl 4-cyclopropyl-2-[2-(trifluoromethoxy)phenyl]pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=C(C2CC2)C=NN1C1=CC=CC=C1OC(F)(F)F CNMNZKPHJJSIBH-UHFFFAOYSA-N 0.000 description 1
- ADEQGMXEHRCMKL-UHFFFAOYSA-N ethyl 6-bromo-1,2-benzoxazole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OCC)=NOC2=C1 ADEQGMXEHRCMKL-UHFFFAOYSA-N 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
- JZGZKRJVTIRPOK-UHFFFAOYSA-N ethyl thiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC=CS1 JZGZKRJVTIRPOK-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 102000006602 glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 108010003814 member 2 group B nuclear receptor subfamily 0 Proteins 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WMCUKJTWFDYDML-UHFFFAOYSA-N methyl 1-(4-formylphenyl)cyclopropane-1-carboxylate Chemical compound C=1C=C(C=O)C=CC=1C1(C(=O)OC)CC1 WMCUKJTWFDYDML-UHFFFAOYSA-N 0.000 description 1
- VDKNOCBCIJGIOC-UHFFFAOYSA-N methyl 1-(4-methylphenyl)cyclopropane-1-carboxylate Chemical compound C=1C=C(C)C=CC=1C1(C(=O)OC)CC1 VDKNOCBCIJGIOC-UHFFFAOYSA-N 0.000 description 1
- LOXCTPDCGDIIIJ-UHFFFAOYSA-N methyl 1-[4-(bromomethyl)phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(CBr)C=CC=1C1(C(=O)OC)CC1 LOXCTPDCGDIIIJ-UHFFFAOYSA-N 0.000 description 1
- VONGYFFEWFJHNP-UHFFFAOYSA-N methyl 1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 1
- ACCUUUNXLXOTHG-UHFFFAOYSA-N methyl 2,6-difluoro-4-(4-hydroxy-2-methylphenyl)benzoate Chemical compound C1=C(F)C(C(=O)OC)=C(F)C=C1C1=CC=C(O)C=C1C ACCUUUNXLXOTHG-UHFFFAOYSA-N 0.000 description 1
- YXXXYJUILAIMES-UHFFFAOYSA-N methyl 2-(2,6-dichloro-4-fluorophenyl)-4-propan-2-ylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)C=NN1C1=C(Cl)C=C(F)C=C1Cl YXXXYJUILAIMES-UHFFFAOYSA-N 0.000 description 1
- BBXUUQXFFBJQBW-UHFFFAOYSA-N methyl 2-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CC=O BBXUUQXFFBJQBW-UHFFFAOYSA-N 0.000 description 1
- PDYBKGSAHOFAHN-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound OC1=CC=C(C=C1)C=1SC(=C(N=1)C)C(=O)OC PDYBKGSAHOFAHN-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
- CFHNGWMTGLSMST-UHFFFAOYSA-N methyl 2-(6-hydroxy-1-benzothiophen-3-yl)acetate Chemical compound OC1=CC=C2C(CC(=O)OC)=CSC2=C1 CFHNGWMTGLSMST-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
- 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
- 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
- VQKLNUAFDHYEFB-UHFFFAOYSA-N methyl 2-[3-(4-hydroxy-2-methylphenyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(C=2C(=CC(O)=CC=2)C)=C1 VQKLNUAFDHYEFB-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
- VAQBJVZNPBNHGC-UHFFFAOYSA-N methyl 2-amino-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1N VAQBJVZNPBNHGC-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
- MXTBKONLFSQASX-UHFFFAOYSA-N methyl 2-bromo-4-(4h-1,3-dioxin-2-yl)benzoate Chemical compound C1=C(Br)C(C(=O)OC)=CC=C1C1OC=CCO1 MXTBKONLFSQASX-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
- 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 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
- 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
- FSQOQFQTZISUJL-UHFFFAOYSA-N methyl 2-butoxy-4-methylbenzoate Chemical compound CCCCOC1=CC(C)=CC=C1C(=O)OC FSQOQFQTZISUJL-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
- 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 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
- BZVOGSNBJLGYFV-UHFFFAOYSA-N methyl 3-(bromomethyl)-2-propan-2-yloxybenzoate Chemical compound COC(C1=C(C(=CC=C1)CBr)OC(C)C)=O BZVOGSNBJLGYFV-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
- IHXVDUQOHZEJLU-UHFFFAOYSA-N methyl 3-[2-(4-hydroxy-2-methylphenyl)ethenyl]benzoate Chemical compound COC(=O)C1=CC=CC(C=CC=2C(=CC(O)=CC=2)C)=C1 IHXVDUQOHZEJLU-UHFFFAOYSA-N 0.000 description 1
- MDPRILJZISNKTF-UHFFFAOYSA-N methyl 3-[3-(4-hydroxy-2-methylphenyl)phenyl]prop-2-enoate Chemical compound COC(=O)C=CC1=CC=CC(C=2C(=CC(O)=CC=2)C)=C1 MDPRILJZISNKTF-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
- JFIBGYJEALNQIX-UHFFFAOYSA-N methyl 3-formamido-4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C(NC=O)=C1 JFIBGYJEALNQIX-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
- LXCQVWRESZDFGW-UHFFFAOYSA-N methyl 3-hydroxy-4-iodobenzoate Chemical compound COC(=O)C1=CC=C(I)C(O)=C1 LXCQVWRESZDFGW-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
- 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
- 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 1
- 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 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
- PEJFTMUXOSWNSS-UHFFFAOYSA-N methyl 4-[(4-hydroxy-n,2-dimethylanilino)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1C PEJFTMUXOSWNSS-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
- PKQUYHNHKATQGH-UHFFFAOYSA-N methyl 4-[[4-[tert-butyl(dimethyl)silyl]oxy-n,2-dimethylanilino]methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C PKQUYHNHKATQGH-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- CYEXEOXALMJXDI-UHFFFAOYSA-N methyl 4-bromo-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1C CYEXEOXALMJXDI-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
- MXLVMXVIALSSLJ-UHFFFAOYSA-N methyl 4-chloro-1,2-dimethylindole-3-carboxylate Chemical compound C1=CC(Cl)=C2C(C(=O)OC)=C(C)N(C)C2=C1 MXLVMXVIALSSLJ-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
- DSXKFVAZLNEDTI-UHFFFAOYSA-N methyl 4-formyl-2-pentylbenzoate Chemical compound CCCCCC1=CC(C=O)=CC=C1C(=O)OC DSXKFVAZLNEDTI-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
- 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
- APLVQJOTIQUJAB-UHFFFAOYSA-N methyl 4-methyl-3-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=C(C)C(CC=O)=C1 APLVQJOTIQUJAB-UHFFFAOYSA-N 0.000 description 1
- LXUTXZRWQVCTTR-UHFFFAOYSA-N methyl 4-methyl-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C)C(C(F)(F)F)=C1 LXUTXZRWQVCTTR-UHFFFAOYSA-N 0.000 description 1
- LPLYJJXZWSVXHW-UHFFFAOYSA-N methyl 4-methylnaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=C(C)C2=C1 LPLYJJXZWSVXHW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BTZOMWXSWVOOHG-UHFFFAOYSA-N methyl 4-sulfanylbenzoate Chemical compound COC(=O)C1=CC=C(S)C=C1 BTZOMWXSWVOOHG-UHFFFAOYSA-N 0.000 description 1
- COVWTINOAVASMD-UHFFFAOYSA-N methyl 5-(2-chloro-4-hydroxyphenyl)-4-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C)=C1C1=CC=C(O)C=C1Cl COVWTINOAVASMD-UHFFFAOYSA-N 0.000 description 1
- KQHSDTRELVCLHW-UHFFFAOYSA-N methyl 5-(2-chloro-4-hydroxyphenyl)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1Cl KQHSDTRELVCLHW-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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 1
- PSGHMPWEDAMDGX-UHFFFAOYSA-N methyl 5-(bromomethyl)-2-butoxybenzoate Chemical compound CCCCOC1=CC=C(CBr)C=C1C(=O)OC PSGHMPWEDAMDGX-UHFFFAOYSA-N 0.000 description 1
- FJYDBKPPGRZSOZ-UHFFFAOYSA-N methyl 5-bromo-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(Br)=CC=C1O FJYDBKPPGRZSOZ-UHFFFAOYSA-N 0.000 description 1
- RJWZFHRMQRWEIH-UHFFFAOYSA-N methyl 5-bromo-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC(C)=C(Br)S1 RJWZFHRMQRWEIH-UHFFFAOYSA-N 0.000 description 1
- AJTSGHATZFXLKC-UHFFFAOYSA-N methyl 5-methoxy-2-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1CC=O AJTSGHATZFXLKC-UHFFFAOYSA-N 0.000 description 1
- QINDVPODKVLUCW-UHFFFAOYSA-N methyl 5-methyl-2-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC(C)=CC=C1CC=O QINDVPODKVLUCW-UHFFFAOYSA-N 0.000 description 1
- ASHFLMVXCNOCHI-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1h-indole-2-carboxylate Chemical compound C1=C2NC(C(=O)OC)=CC2=CC=C1C1=CC=C(O)C=C1C ASHFLMVXCNOCHI-UHFFFAOYSA-N 0.000 description 1
- GHWMXIAQENLMIG-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C GHWMXIAQENLMIG-UHFFFAOYSA-N 0.000 description 1
- GXBAOCBKESNGJI-UHFFFAOYSA-N methyl 6-(4-hydroxyphenyl)-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=C1 GXBAOCBKESNGJI-UHFFFAOYSA-N 0.000 description 1
- IRQSKJQDKUAART-UHFFFAOYSA-N methyl 6-(bromomethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(CBr)N=C1 IRQSKJQDKUAART-UHFFFAOYSA-N 0.000 description 1
- SJICLOHNXORMBV-UHFFFAOYSA-N methyl 6-bromo-1-methylindazole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=NN(C)C2=C1 SJICLOHNXORMBV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FIPMZRPZSZXFGK-UHFFFAOYSA-N methyl 6-bromo-1h-indazole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=NNC2=C1 FIPMZRPZSZXFGK-UHFFFAOYSA-N 0.000 description 1
- VXZQFDQHCLWBHX-UHFFFAOYSA-N methyl 6-chloro-1,2-dimethylindole-3-carboxylate Chemical compound ClC1=CC=C2C(C(=O)OC)=C(C)N(C)C2=C1 VXZQFDQHCLWBHX-UHFFFAOYSA-N 0.000 description 1
- ODAVTXGNQNWWJZ-UHFFFAOYSA-N methyl 6-hydroxy-2-methyl-1-benzofuran-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=C(C)OC2=C1 ODAVTXGNQNWWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- FRIYZZJZQXAKQF-UHFFFAOYSA-N n-(2-bromoethyl)-4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylaniline Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC1=CC=C(N(C)CCBr)C(C)=C1 FRIYZZJZQXAKQF-UHFFFAOYSA-N 0.000 description 1
- XHXVAJHZTIXQQD-UHFFFAOYSA-N n-[bis(aziridin-1-yl)phosphoryl]-5-[(4-butoxyphenyl)methyl]-2,6-dimethylpyrimidin-4-amine Chemical compound C1=CC(OCCCC)=CC=C1CC1=C(C)N=C(C)N=C1NP(=O)(N1CC1)N1CC1 XHXVAJHZTIXQQD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 108091008679 retinoid hormone receptors Proteins 0.000 description 1
- 102000027483 retinoid hormone receptors Human genes 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ZPISGWNOROJGNW-UHFFFAOYSA-N tert-butyl n-[4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-2-methylphenyl]carbamate Chemical compound CC(C)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC1=CC=C(NC(=O)OC(C)(C)C)C(C)=C1 ZPISGWNOROJGNW-UHFFFAOYSA-N 0.000 description 1
- CASWTRCMBMULAJ-UHFFFAOYSA-N tert-butyl n-[4-[[4-cyclopropyl-2-[2-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]-2-methylphenyl]-n-methylcarbamate Chemical compound C1=C(C)C(N(C(=O)OC(C)(C)C)C)=CC=C1OCC1=C(C2CC2)C=NN1C1=CC=CC=C1OC(F)(F)F CASWTRCMBMULAJ-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- CIMWKWOZHMGSHS-UHFFFAOYSA-M zinc;pentane;bromide Chemical compound Br[Zn+].CCCC[CH2-] CIMWKWOZHMGSHS-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| Application Number | Priority Date | Filing Date | Title |
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| US80292006P | 2006-05-24 | 2006-05-24 | |
| US60/802,920 | 2006-05-24 | ||
| US86999506P | 2006-12-14 | 2006-12-14 | |
| US60/869,995 | 2006-12-14 | ||
| PCT/US2007/069445 WO2007140183A1 (en) | 2006-05-24 | 2007-05-22 | Fxr agonists |
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| BRPI0712262A2 true BRPI0712262A2 (pt) | 2012-07-10 |
Family
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| Country | Link |
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| EP (1) | EP2029547B1 (enExample) |
| JP (1) | JP5119241B2 (enExample) |
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| PL (1) | PL2029547T3 (enExample) |
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| TW200906823A (en) | 2007-07-16 | 2009-02-16 | Lilly Co Eli | Compounds and methods for modulating FXR |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| KR20100135711A (ko) | 2007-12-20 | 2010-12-27 | 엔비보 파마슈티칼즈, 인코퍼레이티드 | 사중치환된 벤젠 |
| EP2128158A1 (en) | 2008-05-26 | 2009-12-02 | Phenex Pharmaceuticals AG | Heterocyclic cyclopropyl-substituted FXR binding compounds |
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| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| KR20210110407A (ko) * | 2016-09-14 | 2021-09-07 | 노파르티스 아게 | Fxr 작용제의 신규 요법 |
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| WO2021108974A1 (en) | 2019-12-03 | 2021-06-10 | Gannex Pharma Co., Ltd | Compounds for modulating activity of fxr and uses thereof |
| CN110878052B (zh) * | 2019-12-11 | 2021-05-07 | 山东大学 | 一种含有fxr激动剂的化合物及其制备方法和应用 |
| WO2021122645A1 (en) | 2019-12-20 | 2021-06-24 | Syngenta Crop Protection Ag | Pesticidally active azole-amide compounds |
| EP4090327B1 (en) | 2020-01-15 | 2025-03-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of fxr agonists for treating an infection by hepatitis d virus |
| JP2024502673A (ja) | 2021-01-14 | 2024-01-22 | ウエヌイグレックオ・ファーマ | Ｈｂｖ感染の処置のためのｆｘｒアゴニストとｉｆｎの相乗効果 |
| CA3213217A1 (en) | 2021-04-28 | 2022-11-03 | Raphael Darteil | Strong potentiation of tlr3 agonists effects using fxr agonists as a combined treatment |
| JP7760117B2 (ja) * | 2021-08-23 | 2025-10-27 | 大学共同利用機関法人情報・システム研究機構 | オーキシンデグロンシステムのキット、及びその使用 |
| CN119462450A (zh) * | 2024-12-02 | 2025-02-18 | 西安近代化学研究所 | 一种双三氟甲基硫醚的制备方法 |
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| JPH07138258A (ja) | 1993-11-16 | 1995-05-30 | Taiho Yakuhin Kogyo Kk | チアゾリジンジオン誘導体又はその塩 |
| EP1285914B1 (en) | 2001-08-13 | 2007-12-19 | PheneX Pharmaceuticals AG | Nr1h4 nuclear receptor binding compounds |
| AU2003290700A1 (en) * | 2002-11-22 | 2004-06-18 | Smithkline Beecham Corporation | Farnesoid x receptor agonists |
| CN1909902A (zh) | 2003-12-22 | 2007-02-07 | 伊莱利利公司 | 用于治疗糖尿病的作为ppar调节剂的三唑、噁二唑和噻二唑衍生物 |
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Also Published As
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| CN101448791A (zh) | 2009-06-03 |
| DK2029547T3 (da) | 2010-07-26 |
| US20090270460A1 (en) | 2009-10-29 |
| CA2651378A1 (en) | 2007-12-06 |
| CA2651378C (en) | 2012-08-28 |
| AU2007267606A1 (en) | 2007-12-06 |
| JP5119241B2 (ja) | 2013-01-16 |
| EA015632B1 (ru) | 2011-10-31 |
| EP2029547B1 (en) | 2010-04-28 |
| JP2009538335A (ja) | 2009-11-05 |
| WO2007140183A1 (en) | 2007-12-06 |
| US7846960B2 (en) | 2010-12-07 |
| EP2029547A1 (en) | 2009-03-04 |
| CN101448791B (zh) | 2011-11-16 |
| EA200870570A1 (ru) | 2009-04-28 |
| MX2008014854A (es) | 2008-12-05 |
| PL2029547T3 (pl) | 2010-09-30 |
| EA015632B9 (ru) | 2012-08-30 |
| ATE465996T1 (de) | 2010-05-15 |
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