MX2008014854A - Antagonistas de fxr. - Google Patents
Antagonistas de fxr.Info
- Publication number
- MX2008014854A MX2008014854A MX2008014854A MX2008014854A MX2008014854A MX 2008014854 A MX2008014854 A MX 2008014854A MX 2008014854 A MX2008014854 A MX 2008014854A MX 2008014854 A MX2008014854 A MX 2008014854A MX 2008014854 A MX2008014854 A MX 2008014854A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- phenyl
- isopropyl
- ylmethoxy
- hydrogen
- Prior art date
Links
- 239000000556 agonist Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 320
- 238000000034 method Methods 0.000 claims abstract description 19
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 17
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 benzoisoxazolyl Chemical group 0.000 claims description 384
- 229910052739 hydrogen Inorganic materials 0.000 claims description 158
- 239000001257 hydrogen Substances 0.000 claims description 147
- 239000002253 acid Substances 0.000 claims description 116
- 239000005711 Benzoic acid Substances 0.000 claims description 83
- 150000002431 hydrogen Chemical class 0.000 claims description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 59
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 50
- 125000001309 chloro group Chemical group Cl* 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 47
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 20
- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 19
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group 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
- 150000003626 triacylglycerols Chemical class 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
- 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 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 238000008214 LDL Cholesterol Methods 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 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 group 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
- NRISCNNFEGZXJO-UHFFFAOYSA-N 3-[[4-[[4-cyclopropyl-2-(2,6-dichlorophenyl)pyrazol-3-yl]methoxy]-n-methylanilino]methyl]benzoic acid Chemical compound C=1C=C(OCC=2N(N=CC=2C2CC2)C=2C(=CC=CC=2Cl)Cl)C=CC=1N(C)CC1=CC=CC(C(O)=O)=C1 NRISCNNFEGZXJO-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
- 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
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 528
- 238000002360 preparation method Methods 0.000 description 332
- 235000019439 ethyl acetate Nutrition 0.000 description 213
- 239000000203 mixture Substances 0.000 description 208
- 239000000243 solution Substances 0.000 description 169
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 157
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 141
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 133
- 239000011541 reaction mixture Substances 0.000 description 122
- 238000006243 chemical reaction Methods 0.000 description 121
- 229910001868 water Inorganic materials 0.000 description 121
- 230000002829 reductive effect Effects 0.000 description 105
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
- 238000005481 NMR spectroscopy Methods 0.000 description 90
- 101150041968 CDC13 gene Proteins 0.000 description 84
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 84
- 239000012044 organic layer Substances 0.000 description 82
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
- 239000012267 brine Substances 0.000 description 68
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 68
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 66
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 64
- 239000010410 layer Substances 0.000 description 61
- 238000003818 flash chromatography Methods 0.000 description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- 239000007787 solid Substances 0.000 description 58
- 239000007858 starting material Substances 0.000 description 55
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
- 239000011734 sodium Substances 0.000 description 32
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 150000004702 methyl esters Chemical class 0.000 description 28
- 239000000126 substance Substances 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- 235000010233 benzoic acid Nutrition 0.000 description 26
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
- 235000011152 sodium sulphate Nutrition 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 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 21
- 238000004587 chromatography analysis Methods 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 20
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 229910000027 potassium carbonate Inorganic materials 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 235000012000 cholesterol Nutrition 0.000 description 14
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 14
- 235000011181 potassium carbonates Nutrition 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 229920006395 saturated elastomer Polymers 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 229920002554 vinyl polymer Polymers 0.000 description 13
- 102100038495 Bile acid receptor Human genes 0.000 description 11
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 description 11
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 102100023172 Nuclear receptor subfamily 0 group B member 2 Human genes 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 9
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 9
- ZMYVNLUQZOLTHI-UHFFFAOYSA-N 4-[[2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazol-3-yl]methoxy]-n,2-dimethylaniline Chemical compound C1=C(C)C(NC)=CC=C1OCC1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl ZMYVNLUQZOLTHI-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- LHJKZERUIPGPCK-UHFFFAOYSA-N methyl 4-formyl-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1C LHJKZERUIPGPCK-UHFFFAOYSA-N 0.000 description 8
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 239000006188 syrup Substances 0.000 description 8
- 235000020357 syrup Nutrition 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- CKBBSFOOIOHLPC-UHFFFAOYSA-N 6-bromo-1-benzothiophene-2-carboxylic acid Chemical compound C1=C(Br)C=C2SC(C(=O)O)=CC2=C1 CKBBSFOOIOHLPC-UHFFFAOYSA-N 0.000 description 7
- ZXMDECZLLPFSJO-UHFFFAOYSA-N 6-bromo-1-benzothiophene-3-carboxylic acid Chemical compound BrC1=CC=C2C(C(=O)O)=CSC2=C1 ZXMDECZLLPFSJO-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 108010010234 HDL Lipoproteins Proteins 0.000 description 7
- 102000015779 HDL Lipoproteins Human genes 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000007832 Na2SO4 Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
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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 2
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- 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
- FIKBYSIYPIRVFD-UHFFFAOYSA-N methyl 2-butoxy-4-formylbenzoate Chemical compound CCCCOC1=CC(C=O)=CC=C1C(=O)OC FIKBYSIYPIRVFD-UHFFFAOYSA-N 0.000 description 2
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- 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
- 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
- UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- 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
- 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 2
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OGYAVWKYDVBIMW-UHFFFAOYSA-N methyl 4-methoxy-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1C OGYAVWKYDVBIMW-UHFFFAOYSA-N 0.000 description 2
- FINKSGWSBJRISB-UHFFFAOYSA-N methyl 4-methoxy-2-methylbenzoate Natural products COC(=O)C1=CC=C(O)C=C1C FINKSGWSBJRISB-UHFFFAOYSA-N 0.000 description 2
- 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
- ZCPCZELMTZDPAK-UHFFFAOYSA-N methyl 5-(4-hydroxy-2-methylphenyl)-4-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C)=C1C1=CC=C(O)C=C1C ZCPCZELMTZDPAK-UHFFFAOYSA-N 0.000 description 2
- UORNZLAJCQFFFU-UHFFFAOYSA-N methyl 5-hydroxy-2-propylbenzoate Chemical compound CCCC1=CC=C(O)C=C1C(=O)OC UORNZLAJCQFFFU-UHFFFAOYSA-N 0.000 description 2
- DBVHXKYDXKZWTM-UHFFFAOYSA-N methyl 5-methoxy-2-propylbenzoate Chemical compound CCCC1=CC=C(OC)C=C1C(=O)OC DBVHXKYDXKZWTM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MOOHLFRSZUFCOU-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-benzothiophene-2-carboxylate Chemical compound C1=C2SC(C(=O)OC)=CC2=CC=C1C1=CC=C(O)C=C1C MOOHLFRSZUFCOU-UHFFFAOYSA-N 0.000 description 2
- 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
- WKLAMMFIYQQZPD-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1h-indole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CNC2=CC=1C1=CC=C(O)C=C1C WKLAMMFIYQQZPD-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
- RPUAGJVFXJADEK-UHFFFAOYSA-N methyl 6-chloro-2-methyl-1h-indole-3-carboxylate Chemical compound ClC1=CC=C2C(C(=O)OC)=C(C)NC2=C1 RPUAGJVFXJADEK-UHFFFAOYSA-N 0.000 description 2
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 2
- OQJBFFCUFALWQL-UHFFFAOYSA-N n-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 description 2
- FTNFEHXDETWERN-UHFFFAOYSA-N n-[bis(aziridin-1-yl)phosphoryl]-2,6-dimethyl-5-[(4-propan-2-yloxyphenyl)methyl]pyrimidin-4-amine Chemical compound C1=CC(OC(C)C)=CC=C1CC1=C(C)N=C(C)N=C1NP(=O)(N1CC1)N1CC1 FTNFEHXDETWERN-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
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- 235000011056 potassium acetate Nutrition 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
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- 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
- ODYHOIUFIVBVLS-UHFFFAOYSA-N ethyl 1-benzothiophene-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2SC=CC2=C1 ODYHOIUFIVBVLS-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
- RFBZWPFBCXBBJS-UHFFFAOYSA-N ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1B1OC(C)(C)C(C)(C)O1 RFBZWPFBCXBBJS-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
- PFZRLTQDNVYPRP-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-methylphenyl)-1-benzothiophene-5-carboxylate Chemical compound C=1C2=CC(C(=O)OCC)=CC=C2SC=1C1=CC=C(O)C=C1C PFZRLTQDNVYPRP-UHFFFAOYSA-N 0.000 description 1
- FPCXJEYDHZXWDO-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-methylphenyl)-1-benzothiophene-7-carboxylate Chemical compound S1C=2C(C(=O)OCC)=CC=CC=2C=C1C1=CC=C(O)C=C1C FPCXJEYDHZXWDO-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
- YRDCTFWPXGBEPJ-UHFFFAOYSA-N ethyl 2-[2-chloro-6-(trifluoromethyl)phenyl]-4-cyclopropylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=C(C2CC2)C=NN1C1=C(Cl)C=CC=C1C(F)(F)F YRDCTFWPXGBEPJ-UHFFFAOYSA-N 0.000 description 1
- WASLOYGXYDURDY-UHFFFAOYSA-N ethyl 2-[6-(trifluoromethylsulfonyloxy)-1-benzothiophen-3-yl]acetate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=C2C(CC(=O)OCC)=CSC2=C1 WASLOYGXYDURDY-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
- 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
- NPFKOFAJKNFTMP-UHFFFAOYSA-N ethyl 3-[4-(4-hydroxy-2-methylphenyl)phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1C1=CC=C(O)C=C1C NPFKOFAJKNFTMP-UHFFFAOYSA-N 0.000 description 1
- AURADFMZLUCYCD-UHFFFAOYSA-N ethyl 3-acetyl-2-methoxyimino-5-methylhexanoate Chemical compound CCOC(=O)C(=NOC)C(CC(C)C)C(C)=O AURADFMZLUCYCD-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
- XQZIRQWYXJKNSV-UHFFFAOYSA-N ethyl 3-cyclopropyl-4-(dimethylamino)-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C(=CN(C)C)C1CC1 XQZIRQWYXJKNSV-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
- XRMJFFUFRCRGBO-UHFFFAOYSA-N ethyl 4-cyclopropyl-2-(2,6-dichlorophenyl)pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=C(C2CC2)C=NN1C1=C(Cl)C=CC=C1Cl XRMJFFUFRCRGBO-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
- OXPOWFJJRSYFME-UHFFFAOYSA-N ethyl 6-(4-hydroxy-2-methylphenyl)-1,2-benzoxazole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OCC)=NOC2=CC=1C1=CC=C(O)C=C1C OXPOWFJJRSYFME-UHFFFAOYSA-N 0.000 description 1
- VSZYBEHRDDIQQB-UHFFFAOYSA-N ethyl 6-(4-hydroxy-2-methylphenyl)-1h-indole-2-carboxylate Chemical compound C1=C2NC(C(=O)OCC)=CC2=CC=C1C1=CC=C(O)C=C1C VSZYBEHRDDIQQB-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
- 125000004705 ethylthio group Chemical group C(C)S* 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
- 238000011049 filling Methods 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
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 239000000833 heterodimer Substances 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
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 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
- 150000002576 ketones Chemical class 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
- 244000144972 livestock Species 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
- 239000002609 medium Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- LBBMOAOCCQOIAQ-UHFFFAOYSA-N methoxy(phenyl)borinic acid Chemical compound COB(O)C1=CC=CC=C1 LBBMOAOCCQOIAQ-UHFFFAOYSA-N 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
- 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
- IGNYATYBADTSRK-UHFFFAOYSA-N methyl 2-(2,6-dichlorophenyl)-4-propan-2-ylpyrazole-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)C=NN1C1=C(Cl)C=CC=C1Cl IGNYATYBADTSRK-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
- OERYMLHYCBBYLJ-UHFFFAOYSA-N methyl 2-(4-chloro-2-nitrophenyl)-3-hydroxybut-2-enoate Chemical compound COC(=O)C(=C(C)O)C1=CC=C(Cl)C=C1[N+]([O-])=O OERYMLHYCBBYLJ-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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 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
- 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
- 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
- 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
- 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
- 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
- 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
- ULUMAACGWLZNHF-UHFFFAOYSA-N methyl 4-(2-amino-4-methoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1N ULUMAACGWLZNHF-UHFFFAOYSA-N 0.000 description 1
- MBEOKSAQLBKHSD-UHFFFAOYSA-N methyl 4-(2-bromo-4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1Br MBEOKSAQLBKHSD-UHFFFAOYSA-N 0.000 description 1
- 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 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
- TYXOWTXOSOIMSE-UHFFFAOYSA-N methyl 4-(4-methoxy-2-nitrophenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1[N+]([O-])=O TYXOWTXOSOIMSE-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
- 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
- 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
- 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
- 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
- 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
- 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
- LFVDEVQENPHSSD-UHFFFAOYSA-N methyl 4-methyl-2-oxopentanoate Chemical compound COC(=O)C(=O)CC(C)C LFVDEVQENPHSSD-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
- 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
- JIYCCJRJZYQXLS-UHFFFAOYSA-N methyl 5-bromo-2-butoxybenzoate Chemical compound CCCCOC1=CC=C(Br)C=C1C(=O)OC JIYCCJRJZYQXLS-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
- SWUOLYKRMRWPLB-UHFFFAOYSA-N methyl 5-methoxy-2-prop-2-enylbenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1CC=C SWUOLYKRMRWPLB-UHFFFAOYSA-N 0.000 description 1
- ALLLYUJHFZWQHP-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1,2-dimethylindole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=C(C)N(C)C2=CC=1C1=CC=C(O)C=C1C ALLLYUJHFZWQHP-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
- 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
- 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
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 235000020824 obesity Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 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
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical group NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 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
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 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
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 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
- 102000027483 retinoid hormone receptors Human genes 0.000 description 1
- 108091008679 retinoid hormone receptors Proteins 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 101150096065 shp gene Proteins 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 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
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FBUBSOYGNIHPLK-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2-methylphenyl)carbamate Chemical compound CC1=CC(O)=CC=C1NC(=O)OC(C)(C)C FBUBSOYGNIHPLK-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
- 238000011285 therapeutic regimen Methods 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 229940062627 tribasic potassium phosphate Drugs 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
- TVBIVRGNYNBFCD-UHFFFAOYSA-N triethylazanium;trifluoromethanesulfonate Chemical compound CC[NH+](CC)CC.[O-]S(=O)(=O)C(F)(F)F TVBIVRGNYNBFCD-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
- 235000012431 wafers Nutrition 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- C07D401/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
-
- 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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- General Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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| US86999506P | 2006-12-14 | 2006-12-14 | |
| PCT/US2007/069445 WO2007140183A1 (en) | 2006-05-24 | 2007-05-22 | Fxr agonists |
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| MX2008014854A true MX2008014854A (es) | 2008-12-05 |
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| EP (1) | EP2029547B1 (enExample) |
| JP (1) | JP5119241B2 (enExample) |
| CN (1) | CN101448791B (enExample) |
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| MX (1) | MX2008014854A (enExample) |
| PL (1) | PL2029547T3 (enExample) |
| WO (1) | WO2007140183A1 (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 |
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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 |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
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| KR20210110407A (ko) * | 2016-09-14 | 2021-09-07 | 노파르티스 아게 | Fxr 작용제의 신규 요법 |
| JP2019537557A (ja) | 2016-10-04 | 2019-12-26 | エナンタ ファーマシューティカルズ インコーポレイテッド | Ｆｘｒアゴニストとしてのイソキサゾール類似体およびその使用方法 |
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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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| BRPI0712262A2 (pt) | 2012-07-10 |
| 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 |
| PL2029547T3 (pl) | 2010-09-30 |
| EA015632B9 (ru) | 2012-08-30 |
| ATE465996T1 (de) | 2010-05-15 |
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