TW200825054A - Quinoline compounds - Google Patents

Info

Publication number

TW200825054A

TW200825054A TW096138869A TW96138869A TW200825054A TW 200825054 A TW200825054 A TW 200825054A TW 096138869 A TW096138869 A TW 096138869A TW 96138869 A TW96138869 A TW 96138869A TW 200825054 A TW200825054 A TW 200825054A

Authority

TW

Taiwan

Prior art keywords

group

atoms

optionally substituted

substituted

compound

Prior art date

2006-10-18

Links

• Espacenet
• Global Dossier
• Discuss

• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 5
• 238000000034 method Methods 0.000 claims abstract description 103
• 102000004311 liver X receptors Human genes 0.000 claims abstract description 29
• 108090000865 liver X receptors Proteins 0.000 claims abstract description 29
• 150000001875 compounds Chemical class 0.000 claims description 445
• 125000004429 atom Chemical group 0.000 claims description 252
• -1 [1,2,4]-oxadiazolyl Chemical group 0.000 claims description 247
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 212
• 125000000217 alkyl group Chemical group 0.000 claims description 122
• 239000001257 hydrogen Substances 0.000 claims description 113
• 229910052739 hydrogen Inorganic materials 0.000 claims description 113
• 125000000623 heterocyclic group Chemical group 0.000 claims description 107
• 125000003118 aryl group Chemical group 0.000 claims description 104
• 239000000460 chlorine Substances 0.000 claims description 79
• 125000001072 heteroaryl group Chemical group 0.000 claims description 79
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 60
• 125000005843 halogen group Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 59
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 43
• 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 claims description 43
• 125000003342 alkenyl group Chemical group 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 31
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• 239000007789 gas Substances 0.000 claims description 26
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 23
• 230000000694 effects Effects 0.000 claims description 22
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 235000012000 cholesterol Nutrition 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
• 125000004122 cyclic group Chemical group 0.000 claims description 18
• 239000011737 fluorine Substances 0.000 claims description 18
• 229910052731 fluorine Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 201000010099 disease Diseases 0.000 claims description 17
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 16
• 241000219112 Cucumis Species 0.000 claims description 15
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 15
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 15
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 13
• 125000004104 aryloxy group Chemical group 0.000 claims description 13
• 230000001154 acute effect Effects 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000006413 ring segment Chemical group 0.000 claims description 12
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
• 229910052703 rhodium Inorganic materials 0.000 claims description 11
• 125000005404 thioheteroaryloxy group Chemical group 0.000 claims description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 229910052707 ruthenium Inorganic materials 0.000 claims description 10
• 210000002966 serum Anatomy 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 125000005296 thioaryloxy group Chemical group 0.000 claims description 10
• 230000003143 atherosclerotic effect Effects 0.000 claims description 9
• 150000002632 lipids Chemical class 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 230000009759 skin aging Effects 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 150000001540 azides Chemical class 0.000 claims description 7
• 230000001965 increasing effect Effects 0.000 claims description 7
• 230000004054 inflammatory process Effects 0.000 claims description 7
• 239000002243 precursor Substances 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 239000002689 soil Substances 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 6
• 206010040047 Sepsis Diseases 0.000 claims description 6
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
• 230000001684 chronic effect Effects 0.000 claims description 6
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
• 206010012442 Dermatitis contact Diseases 0.000 claims description 5
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
• 238000008214 LDL Cholesterol Methods 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 208000010247 contact dermatitis Diseases 0.000 claims description 5
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 230000003902 lesion Effects 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 150000003431 steroids Chemical class 0.000 claims description 5
• 239000004575 stone Substances 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• 102000004127 Cytokines Human genes 0.000 claims description 4
• 108090000695 Cytokines Proteins 0.000 claims description 4
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
• 201000009273 Endometriosis Diseases 0.000 claims description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 230000032683 aging Effects 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 4
• 208000029078 coronary artery disease Diseases 0.000 claims description 4
• 125000000524 functional group Chemical group 0.000 claims description 4
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
• 206010043778 thyroiditis Diseases 0.000 claims description 4
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
• 206010012735 Diarrhoea Diseases 0.000 claims description 3
• 102000034570 NR1 subfamily Human genes 0.000 claims description 3
• 108020001305 NR1 subfamily Proteins 0.000 claims description 3
• 206010051246 Photodermatosis Diseases 0.000 claims description 3
• 230000003848 cartilage regeneration Effects 0.000 claims description 3
• 230000001906 cholesterol absorption Effects 0.000 claims description 3
• 208000018631 connective tissue disease Diseases 0.000 claims description 3
• 229910052805 deuterium Chemical group 0.000 claims description 3
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
• NOVHEGOWZNFVGT-UHFFFAOYSA-N hydrazine Chemical compound NN.NN NOVHEGOWZNFVGT-UHFFFAOYSA-N 0.000 claims description 3
• 235000013336 milk Nutrition 0.000 claims description 3
• 239000008267 milk Substances 0.000 claims description 3
• 210000004080 milk Anatomy 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 230000008845 photoaging Effects 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• 125000004354 sulfur functional group Chemical group 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 229910002651 NO3 Inorganic materials 0.000 claims description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
• MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 2
• 125000006612 decyloxy group Chemical group 0.000 claims description 2
• 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 2
• 230000008482 dysregulation Effects 0.000 claims description 2
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 2
• 230000001939 inductive effect Effects 0.000 claims description 2
• 125000005403 thiohaloalkoxy group Chemical group 0.000 claims description 2
• 125000005323 thioketone group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 3
• 150000001336 alkenes Chemical class 0.000 claims 2
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 2
• QSJNAFJALFWFMT-UHFFFAOYSA-N meridine Chemical compound N1C=CC(=O)C2=C1C(=O)C1=NC=CC3=C(C=CC=C4)C4=NC2=C13 QSJNAFJALFWFMT-UHFFFAOYSA-N 0.000 claims 2
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims 1
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
• 206010003246 arthritis Diseases 0.000 claims 1
• 210000000988 bone and bone Anatomy 0.000 claims 1
• 125000003700 epoxy group Chemical group 0.000 claims 1
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• 230000004968 inflammatory condition Effects 0.000 claims 1
• 230000002757 inflammatory effect Effects 0.000 claims 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
• 125000004001 thioalkyl group Chemical group 0.000 claims 1
• 230000002792 vascular Effects 0.000 claims 1
• 208000019553 vascular disease Diseases 0.000 claims 1
• 239000013598 vector Substances 0.000 claims 1
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 90
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 304
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 202
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 130
• 235000019439 ethyl acetate Nutrition 0.000 description 126
• 239000000203 mixture Substances 0.000 description 114
• 239000002585 base Substances 0.000 description 105
• 238000006243 chemical reaction Methods 0.000 description 105
• 239000007787 solid Substances 0.000 description 89
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
• 230000002829 reductive effect Effects 0.000 description 61
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 55
• 239000000376 reactant Substances 0.000 description 54
• 229940076134 benzene Drugs 0.000 description 48
• 239000000243 solution Substances 0.000 description 43
• 239000002253 acid Substances 0.000 description 42
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
• 239000006260 foam Substances 0.000 description 33
• 239000000284 extract Substances 0.000 description 32
• 239000002168 alkylating agent Substances 0.000 description 31
• 229940100198 alkylating agent Drugs 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 30
• 238000002360 preparation method Methods 0.000 description 28
• 125000001424 substituent group Chemical group 0.000 description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 22
• 229910052799 carbon Inorganic materials 0.000 description 22
• 239000002904 solvent Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 108090000623 proteins and genes Proteins 0.000 description 21
• 229920006395 saturated elastomer Polymers 0.000 description 21
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
• 238000004587 chromatography analysis Methods 0.000 description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 19
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
• 239000007864 aqueous solution Substances 0.000 description 18
• 239000012267 brine Substances 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
• 210000004027 cell Anatomy 0.000 description 17
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 17
• 238000010992 reflux Methods 0.000 description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 238000005859 coupling reaction Methods 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 125000001153 fluoro group Chemical group F* 0.000 description 15
• 239000000463 material Substances 0.000 description 15
• 229910000027 potassium carbonate Inorganic materials 0.000 description 15
• 239000000651 prodrug Substances 0.000 description 15
• 229940002612 prodrug Drugs 0.000 description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
• 101150092476 ABCA1 gene Proteins 0.000 description 14
• 230000014509 gene expression Effects 0.000 description 14
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 13
• 229960000583 acetic acid Drugs 0.000 description 13
• 150000001450 anions Chemical class 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 125000002619 bicyclic group Chemical group 0.000 description 12
• 210000004185 liver Anatomy 0.000 description 12
• BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 11
• 102000055510 ATP Binding Cassette Transporter 1 Human genes 0.000 description 11
• 108700005241 ATP Binding Cassette Transporter 1 Proteins 0.000 description 11
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• 210000003491 skin Anatomy 0.000 description 11
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• 125000005362 aryl sulfone group Chemical group 0.000 description 10
• 239000010949 copper Substances 0.000 description 10
• 125000001183 hydrocarbyl group Chemical group 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 229940124530 sulfonamide Drugs 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• 238000002347 injection Methods 0.000 description 9
• 239000007924 injection Substances 0.000 description 9
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 238000006467 substitution reaction Methods 0.000 description 9
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
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