CA2412723C - Benzothiazolyl ppar-gamma modulators - Google Patents

Info

Publication number

CA2412723C

CA2412723C CA2412723A CA2412723A CA2412723C CA 2412723 C CA2412723 C CA 2412723C CA 2412723 A CA2412723 A CA 2412723A CA 2412723 A CA2412723 A CA 2412723A CA 2412723 C CA2412723 C CA 2412723C

Authority

CA

Canada

Prior art keywords

chloro

alkyl

nmr

dmso

compound

Prior art date

2000-06-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 186
• -1 2-benzothiazolyl Chemical group 0.000 claims abstract description 100
• 125000003118 aryl group Chemical group 0.000 claims abstract description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
• 239000001257 hydrogen Substances 0.000 claims abstract description 47
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 41
• 125000001424 substituent group Chemical group 0.000 claims abstract description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
• 230000001404 mediated effect Effects 0.000 claims abstract description 12
• 208000008589 Obesity Diseases 0.000 claims abstract description 7
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 7
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 7
• 235000020824 obesity Nutrition 0.000 claims abstract description 7
• 230000002265 prevention Effects 0.000 claims abstract description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
• 239000000203 mixture Substances 0.000 claims description 128
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 39
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 208000030159 metabolic disease Diseases 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 150000002431 hydrogen Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• 208000027866 inflammatory disease Diseases 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 230000002503 metabolic effect Effects 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 229910052710 silicon Inorganic materials 0.000 claims description 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 2
• 206010022489 Insulin Resistance Diseases 0.000 claims description 2
• 201000001421 hyperglycemia Diseases 0.000 claims description 2
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 2
• 201000008980 hyperinsulinism Diseases 0.000 claims description 2
• 238000007911 parenteral administration Methods 0.000 claims description 2
• 241000282693 Cercopithecidae Species 0.000 claims 1
• 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 72
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
• 208000035475 disorder Diseases 0.000 abstract description 15
• 206010012601 diabetes mellitus Diseases 0.000 abstract description 9
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 6
• 125000005843 halogen group Chemical group 0.000 abstract description 2
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 469
• 238000005160 1H NMR spectroscopy Methods 0.000 description 256
• 239000000460 chlorine Substances 0.000 description 206
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 163
• 239000000243 solution Substances 0.000 description 135
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 131
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 93
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 78
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
• 239000000047 product Substances 0.000 description 67
• 229910001868 water Inorganic materials 0.000 description 61
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• 125000000217 alkyl group Chemical group 0.000 description 50
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
• 239000012267 brine Substances 0.000 description 44
• 239000007787 solid Substances 0.000 description 43
• 238000005481 NMR spectroscopy Methods 0.000 description 42
• 239000011541 reaction mixture Substances 0.000 description 41
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
• 239000012044 organic layer Substances 0.000 description 38
• 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
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 238000001914 filtration Methods 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
• 239000002904 solvent Substances 0.000 description 24
• 239000007832 Na2SO4 Substances 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
• 235000019341 magnesium sulphate Nutrition 0.000 description 20
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• 101150041968 CDC13 gene Proteins 0.000 description 16
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
• 238000006243 chemical reaction Methods 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
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 238000004587 chromatography analysis Methods 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 15
• 238000004440 column chromatography Methods 0.000 description 14
• 239000012043 crude product Substances 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 229910052717 sulfur Inorganic materials 0.000 description 14
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 13
• 238000001816 cooling Methods 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• 238000005406 washing Methods 0.000 description 10
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
• HHLCSFGOTLUREE-UHFFFAOYSA-N 1,2,3-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 HHLCSFGOTLUREE-UHFFFAOYSA-N 0.000 description 7
• 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 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
• 229940126062 Compound A Drugs 0.000 description 7
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 230000027455 binding Effects 0.000 description 7
• 230000004968 inflammatory condition Effects 0.000 description 7
• 239000002198 insoluble material Substances 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 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
• 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 6
• NJXDBSSSDPOAFI-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 NJXDBSSSDPOAFI-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
• QGAINDISDKKVOV-UHFFFAOYSA-N 3-amino-5-[(5-chloro-1,3-benzothiazol-2-yl)oxy]-n-ethylbenzamide Chemical compound CCNC(=O)C1=CC(N)=CC(OC=2SC3=CC=C(Cl)C=C3N=2)=C1 QGAINDISDKKVOV-UHFFFAOYSA-N 0.000 description 6
• 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 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 210000001789 adipocyte Anatomy 0.000 description 6
• 125000002947 alkylene group Chemical group 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 238000000921 elemental analysis Methods 0.000 description 6
• 239000003446 ligand Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
• 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
• 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 5
• 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 5
• 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 5
• 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 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
• 150000001448 anilines Chemical class 0.000 description 5
• 239000012148 binding buffer Substances 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 230000004069 differentiation Effects 0.000 description 5
• 125000004474 heteroalkylene group Chemical group 0.000 description 5
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 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 5
• 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 5
• MDRVWQBDZXCECU-UHFFFAOYSA-N n-[4-[(5-amino-1,3-benzothiazol-2-yl)oxy]-3,5-dichlorophenyl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound N=1C2=CC(N)=CC=C2SC=1OC(C(=C1)Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl MDRVWQBDZXCECU-UHFFFAOYSA-N 0.000 description 5
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 4
• LHUHAARPMJISMM-UHFFFAOYSA-N 2,5-dichloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(Cl)=NC2=C1 LHUHAARPMJISMM-UHFFFAOYSA-N 0.000 description 4
• XNSVFQRJBKTRNE-UHFFFAOYSA-N 2-benzylsulfanyl-3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1SCC1=CC=CC=C1 XNSVFQRJBKTRNE-UHFFFAOYSA-N 0.000 description 4
• ZTMZXFRNPJOZGH-UHFFFAOYSA-N 2-chloro-n-[3-chloro-5-[(5-chloro-1,3-benzothiazol-2-yl)methyl]phenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC(Cl)=CC(CC=2SC3=CC=C(Cl)C=C3N=2)=C1 ZTMZXFRNPJOZGH-UHFFFAOYSA-N 0.000 description 4
• WVJPKRWMBOLFRB-UHFFFAOYSA-N 3,5-dichloro-4-[(6-methoxy-1,3-benzothiazol-2-yl)oxy]aniline Chemical compound S1C2=CC(OC)=CC=C2N=C1OC1=C(Cl)C=C(N)C=C1Cl WVJPKRWMBOLFRB-UHFFFAOYSA-N 0.000 description 4
• BELZOTPYGNBTEZ-UHFFFAOYSA-N 3-[(5-chloro-1,3-benzothiazol-2-yl)oxy]-5-[[2-chloro-4-(trifluoromethyl)phenyl]sulfonylamino]-n-ethylbenzamide Chemical compound C=1C(OC=2SC3=CC=C(Cl)C=C3N=2)=CC(C(=O)NCC)=CC=1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl BELZOTPYGNBTEZ-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• 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 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 239000012190 activator Substances 0.000 description 4
• 235000011114 ammonium hydroxide Nutrition 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 230000003178 anti-diabetic effect Effects 0.000 description 4
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• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
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