CZ302982B6 - 3-Chinolinylfenylsulfonamidová sloucenina, tato sloucenina pro použití jako lécivo a použití této slouceniny pri výrobe léciva - Google Patents

Info

Publication number

CZ302982B6

CZ302982B6 CZ20024197A CZ20024197A CZ302982B6 CZ 302982 B6 CZ302982 B6 CZ 302982B6 CZ 20024197 A CZ20024197 A CZ 20024197A CZ 20024197 A CZ20024197 A CZ 20024197A CZ 302982 B6 CZ302982 B6 CZ 302982B6

Authority

CZ

Czechia

Prior art keywords

compound

dmso

chloro

nmr

mhz

Prior art date

2000-06-28

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 237
• -1 3-Quinolinyl phenyl Chemical group 0.000 title claims abstract description 122
• 239000003814 drug Substances 0.000 title claims abstract description 22
• 229940124530 sulfonamide Drugs 0.000 title abstract description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 76
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 22
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 18
• 230000004968 inflammatory condition Effects 0.000 claims abstract description 17
• 239000012453 solvate Substances 0.000 claims abstract description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 10
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• 208000008589 Obesity Diseases 0.000 claims description 7
• 229910052770 Uranium Inorganic materials 0.000 claims description 7
• 235000020824 obesity Nutrition 0.000 claims description 7
• 229910052721 tungsten Inorganic materials 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 5
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
• 206010022489 Insulin Resistance Diseases 0.000 claims description 4
• 201000001421 hyperglycemia Diseases 0.000 claims description 4
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 4
• 201000008980 hyperinsulinism Diseases 0.000 claims description 4
• 238000007911 parenteral administration Methods 0.000 claims description 4
• 238000011200 topical administration Methods 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 3
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims 1
• 230000002503 metabolic effect Effects 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 163
• 239000000243 solution Substances 0.000 description 155
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 154
• 239000000203 mixture Substances 0.000 description 135
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 99
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
• 239000000047 product Substances 0.000 description 65
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• 238000000034 method Methods 0.000 description 58
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 239000012267 brine Substances 0.000 description 45
• 239000011541 reaction mixture Substances 0.000 description 45
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
• 239000007787 solid Substances 0.000 description 44
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
• 239000012044 organic layer Substances 0.000 description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 31
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 238000001914 filtration Methods 0.000 description 27
• 239000002904 solvent Substances 0.000 description 26
• 108010016731 PPAR gamma Proteins 0.000 description 24
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 24
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
• 238000001816 cooling Methods 0.000 description 22
• 239000012043 crude product Substances 0.000 description 21
• IIPWXGDGKTVTQN-UHFFFAOYSA-N 3,5-dichloro-4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]aniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=NC2=CC=C(Cl)C=C2S1 IIPWXGDGKTVTQN-UHFFFAOYSA-N 0.000 description 20
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
• 238000004587 chromatography analysis Methods 0.000 description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• QDZGJGWDGLHVNK-UHFFFAOYSA-N 2,6-dichloro-1,3-benzothiazole Chemical compound C1=C(Cl)C=C2SC(Cl)=NC2=C1 QDZGJGWDGLHVNK-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 238000000921 elemental analysis Methods 0.000 description 9
• MANPWOKQIHKJPW-UHFFFAOYSA-N 3,5-dichloro-4-(isoquinolin-3-ylmethyl)aniline Chemical compound ClC1=CC(N)=CC(Cl)=C1CC1=CC2=CC=CC=C2C=N1 MANPWOKQIHKJPW-UHFFFAOYSA-N 0.000 description 8
• KYWNWTKGXUPWET-UHFFFAOYSA-N 3,5-dichloro-4-(quinolin-3-ylmethyl)aniline Chemical compound ClC1=CC(N)=CC(Cl)=C1CC1=CN=C(C=CC=C2)C2=C1 KYWNWTKGXUPWET-UHFFFAOYSA-N 0.000 description 8
• ITRFJJLSAYPVGB-UHFFFAOYSA-N 3-(2,6-dichloro-4-nitrophenoxy)-6-methylquinoline Chemical compound C=1C2=CC(C)=CC=C2N=CC=1OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ITRFJJLSAYPVGB-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 150000003456 sulfonamides Chemical class 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
• LHUHAARPMJISMM-UHFFFAOYSA-N 2,5-dichloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(Cl)=NC2=C1 LHUHAARPMJISMM-UHFFFAOYSA-N 0.000 description 7
• QTKZVKRDROGNIQ-UHFFFAOYSA-N 3,5-dichloro-4-(quinolin-2-ylmethyl)aniline Chemical compound ClC1=CC(N)=CC(Cl)=C1CC1=CC=C(C=CC=C2)C2=N1 QTKZVKRDROGNIQ-UHFFFAOYSA-N 0.000 description 7
• KGEXISHTCZHGFT-UHFFFAOYSA-N 4-azaniumyl-2,6-dichlorophenolate Chemical compound NC1=CC(Cl)=C(O)C(Cl)=C1 KGEXISHTCZHGFT-UHFFFAOYSA-N 0.000 description 7
• 239000002198 insoluble material Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• XNSVFQRJBKTRNE-UHFFFAOYSA-N 2-benzylsulfanyl-3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1SCC1=CC=CC=C1 XNSVFQRJBKTRNE-UHFFFAOYSA-N 0.000 description 6
• MCCTXJVKIFYBJV-UHFFFAOYSA-N 2-chloro-4-methoxy-1,3-benzothiazole Chemical compound COC1=CC=CC2=C1N=C(Cl)S2 MCCTXJVKIFYBJV-UHFFFAOYSA-N 0.000 description 6
• GGMDTIJDHGLRNW-UHFFFAOYSA-N 3,5-bis[(5-chloro-1,3-benzothiazol-2-yl)oxy]aniline Chemical compound ClC1=CC=C2SC(OC=3C=C(OC=4SC5=CC=C(Cl)C=C5N=4)C=C(C=3)N)=NC2=C1 GGMDTIJDHGLRNW-UHFFFAOYSA-N 0.000 description 6
• RNVHFNUPNYTNMZ-UHFFFAOYSA-N 3-(2,6-dichloro-4-nitrophenoxy)quinoline-6-carboxylic acid Chemical compound C=1C2=CC(C(=O)O)=CC=C2N=CC=1OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl RNVHFNUPNYTNMZ-UHFFFAOYSA-N 0.000 description 6
• VMNXKIDUTPOHPO-UHFFFAOYSA-N 6-chloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1 VMNXKIDUTPOHPO-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 230000027455 binding Effects 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 239000003446 ligand Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• PDJXUYXEXGLNMW-UHFFFAOYSA-N methyl 3-(2,6-dichloro-4-nitrophenoxy)quinoline-6-carboxylate Chemical compound C=1C2=CC(C(=O)OC)=CC=C2N=CC=1OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl PDJXUYXEXGLNMW-UHFFFAOYSA-N 0.000 description 6
• WNLRCUMSWNCWFD-UHFFFAOYSA-N methyl 3-(4-amino-2,6-dichlorophenoxy)quinoline-6-carboxylate Chemical compound C=1C2=CC(C(=O)OC)=CC=C2N=CC=1OC1=C(Cl)C=C(N)C=C1Cl WNLRCUMSWNCWFD-UHFFFAOYSA-N 0.000 description 6
• LFXVDSOQRJVXTC-UHFFFAOYSA-N methyl 3-hydroxyquinoline-8-carboxylate Chemical compound OC1=CN=C2C(C(=O)OC)=CC=CC2=C1 LFXVDSOQRJVXTC-UHFFFAOYSA-N 0.000 description 6
• QXKIMFUKNOLNJG-UHFFFAOYSA-N n-[4-[(6-amino-1,3-benzothiazol-2-yl)oxy]phenyl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound S1C2=CC(N)=CC=C2N=C1OC(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl QXKIMFUKNOLNJG-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• DMPZJACLHDWUFS-UHFFFAOYSA-N 1,3-benzothiazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CSC2=C1 DMPZJACLHDWUFS-UHFFFAOYSA-N 0.000 description 5
• JJWANONAOYNRME-UHFFFAOYSA-N 2,4-dichloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1Cl JJWANONAOYNRME-UHFFFAOYSA-N 0.000 description 5
• UJPUDOZKKFYJHL-UHFFFAOYSA-N 2,4-dichloro-n-(3-chloro-5-fluoro-4-quinolin-3-yloxyphenyl)-5-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC=2C=C(Cl)C(OC=3C=C4C=CC=CC4=NC=3)=C(F)C=2)=C1Cl UJPUDOZKKFYJHL-UHFFFAOYSA-N 0.000 description 5
• FDTPBIKNYWQLAE-UHFFFAOYSA-N 2,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FDTPBIKNYWQLAE-UHFFFAOYSA-N 0.000 description 5
• BGVLILXNEXIWMW-UHFFFAOYSA-N 2-[(2,6-dichloro-4-nitrophenyl)methyl]-1,3-benzothiazole Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1CC1=NC2=CC=CC=C2S1 BGVLILXNEXIWMW-UHFFFAOYSA-N 0.000 description 5
• JZYXWKXXTIMVOA-UHFFFAOYSA-N 2-chloro-5-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(N)=C1 JZYXWKXXTIMVOA-UHFFFAOYSA-N 0.000 description 5
• PPGSYGPSOLZOOU-UHFFFAOYSA-N 2-chloro-6-(trifluoromethoxy)-1,3-benzothiazole Chemical compound FC(F)(F)OC1=CC=C2N=C(Cl)SC2=C1 PPGSYGPSOLZOOU-UHFFFAOYSA-N 0.000 description 5
• FVUFTABOJFRHSU-UHFFFAOYSA-N 2-chloro-6-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2N=C(Cl)SC2=C1 FVUFTABOJFRHSU-UHFFFAOYSA-N 0.000 description 5
• CKCLOSHFYMUHSU-UHFFFAOYSA-N 2-isoquinolin-3-ylacetonitrile Chemical compound C1=CC=C2C=NC(CC#N)=CC2=C1 CKCLOSHFYMUHSU-UHFFFAOYSA-N 0.000 description 5
• AMNPNQPJCREQBE-UHFFFAOYSA-N 2-quinolin-3-ylacetonitrile Chemical compound C1=CC=CC2=CC(CC#N)=CN=C21 AMNPNQPJCREQBE-UHFFFAOYSA-N 0.000 description 5
• GUTIBLKZIXOZCM-UHFFFAOYSA-N 3-[(2,6-dichloro-4-nitrophenyl)methyl]quinoline Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1CC1=CN=C(C=CC=C2)C2=C1 GUTIBLKZIXOZCM-UHFFFAOYSA-N 0.000 description 5
• KRBRYJLBILJHAS-UHFFFAOYSA-N 3-amino-4-chlorobenzonitrile Chemical compound NC1=CC(C#N)=CC=C1Cl KRBRYJLBILJHAS-UHFFFAOYSA-N 0.000 description 5
• KKNLZRGMHKODES-UHFFFAOYSA-N 3-chloro-5-[(5-chloro-1,3-benzothiazol-2-yl)methyl]aniline Chemical compound NC1=CC(Cl)=CC(CC=2SC3=CC=C(Cl)C=C3N=2)=C1 KKNLZRGMHKODES-UHFFFAOYSA-N 0.000 description 5
• ZVLLYIMPDTXFNC-UHFFFAOYSA-N 3-hydroxy-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC(O)=CC([N+]([O-])=O)=C1 ZVLLYIMPDTXFNC-UHFFFAOYSA-N 0.000 description 5
• FPTKJLNQDMJUDY-UHFFFAOYSA-N 5-chloro-2-[(2,6-dichloro-4-nitrophenyl)methyl]-1,3-benzothiazole Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1CC1=NC2=CC(Cl)=CC=C2S1 FPTKJLNQDMJUDY-UHFFFAOYSA-N 0.000 description 5
• YDYCQECGRFNCNN-UHFFFAOYSA-N 5-chloro-2-[(3-chloro-5-nitrophenyl)methyl]-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(CC=2SC3=CC=C(Cl)C=C3N=2)=C1 YDYCQECGRFNCNN-UHFFFAOYSA-N 0.000 description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 5
• 210000001789 adipocyte Anatomy 0.000 description 5
• 239000012148 binding buffer Substances 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 201000010099 disease Diseases 0.000 description 5
• 239000003480 eluent Substances 0.000 description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
• CMGQQHGOFWZGJH-UHFFFAOYSA-N isoquinolin-3-ylmethanol Chemical compound C1=CC=C2C=NC(CO)=CC2=C1 CMGQQHGOFWZGJH-UHFFFAOYSA-N 0.000 description 5
• OODDBHYJTLZNDL-UHFFFAOYSA-N methyl 3-(2,6-dichloro-4-nitrophenoxy)quinoline-8-carboxylate Chemical compound C=1N=C2C(C(=O)OC)=CC=CC2=CC=1OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl OODDBHYJTLZNDL-UHFFFAOYSA-N 0.000 description 5
• UYQJTXQJNZMDBI-UHFFFAOYSA-N methyl 3-chloro-5-nitrobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1 UYQJTXQJNZMDBI-UHFFFAOYSA-N 0.000 description 5
• QJWJEOFSWPDVCW-UHFFFAOYSA-N n-[3,5-bis[(5-chloro-1,3-benzothiazol-2-yl)oxy]phenyl]-2,4-dichloro-5-methylbenzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC=2C=C(OC=3SC4=CC=C(Cl)C=C4N=3)C=C(OC=3SC4=CC=C(Cl)C=C4N=3)C=2)=C1Cl QJWJEOFSWPDVCW-UHFFFAOYSA-N 0.000 description 5
• PZGNPYOSJCPLAK-UHFFFAOYSA-N n-[3,5-bis[(5-chloro-1,3-benzothiazol-2-yl)oxy]phenyl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC(OC=2SC3=CC=C(Cl)C=C3N=2)=CC(OC=2SC3=CC=C(Cl)C=C3N=2)=C1 PZGNPYOSJCPLAK-UHFFFAOYSA-N 0.000 description 5
• NIGHJTUVLNNLSH-UHFFFAOYSA-N n-[4-[(6-amino-1,3-benzothiazol-2-yl)oxy]-3-chlorophenyl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound S1C2=CC(N)=CC=C2N=C1OC(C(=C1)Cl)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl NIGHJTUVLNNLSH-UHFFFAOYSA-N 0.000 description 5
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 5
• 230000002265 prevention Effects 0.000 description 5
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