EA005976B1 - Хинолинил и бензотиазолил ppar-гамма модуляторы - Google Patents

Info

Publication number

EA005976B1

EA005976B1 EA200300078A EA200300078A EA005976B1 EA 005976 B1 EA005976 B1 EA 005976B1 EA 200300078 A EA200300078 A EA 200300078A EA 200300078 A EA200300078 A EA 200300078A EA 005976 B1 EA005976 B1 EA 005976B1

Authority

EA

Eurasian Patent Office

Prior art keywords

nmr

dmso

chloro

mhz

dichloro

Prior art date

2000-06-28

Links

• Espacenet
• Global Dossier
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• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract description 7
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 title 1
• -1 2-benzothiazolyl Chemical group 0.000 claims abstract description 167
• 150000001875 compounds Chemical class 0.000 claims abstract description 166
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
• 150000002367 halogens Chemical class 0.000 claims abstract description 37
• 239000001257 hydrogen Substances 0.000 claims abstract description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
• 125000001424 substituent group Chemical group 0.000 claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
• 230000001404 mediated effect Effects 0.000 claims abstract description 10
• 208000008589 Obesity Diseases 0.000 claims abstract description 9
• 235000020824 obesity Nutrition 0.000 claims abstract description 9
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 3
• 239000000203 mixture Substances 0.000 claims description 136
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 19
• 239000000460 chlorine Substances 0.000 claims description 16
• 208000030159 metabolic disease Diseases 0.000 claims description 12
• 239000013256 coordination polymer Substances 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 230000004968 inflammatory condition Effects 0.000 claims description 7
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 2
• 230000002503 metabolic effect Effects 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims 2
• 241000282693 Cercopithecidae Species 0.000 claims 1
• 150000002632 lipids Chemical class 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 230000008520 organization Effects 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 230000000069 prophylactic effect Effects 0.000 claims 1
• 239000012453 solvate Substances 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 74
• 125000003118 aryl group Chemical group 0.000 abstract description 31
• 206010012601 diabetes mellitus Diseases 0.000 abstract description 10
• 230000002265 prevention Effects 0.000 abstract description 9
• 208000035475 disorder Diseases 0.000 abstract description 3
• 102000000536 PPAR gamma Human genes 0.000 abstract 2
• 108010016731 PPAR gamma Proteins 0.000 abstract 2
• 238000005481 NMR spectroscopy Methods 0.000 description 298
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 129
• 239000000243 solution Substances 0.000 description 116
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 108
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• 239000000047 product Substances 0.000 description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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 45
• 239000012267 brine Substances 0.000 description 44
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 39
• 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
• 238000010992 reflux Methods 0.000 description 33
• 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
• 239000002244 precipitate Substances 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• 238000001914 filtration Methods 0.000 description 24
• 125000004404 heteroalkyl group Chemical group 0.000 description 24
• 238000001816 cooling Methods 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
• 230000002829 reductive effect Effects 0.000 description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 238000004587 chromatography analysis Methods 0.000 description 17
• 239000000706 filtrate Substances 0.000 description 16
• 239000002253 acid Substances 0.000 description 15
• 239000012043 crude product Substances 0.000 description 15
• 229910052757 nitrogen Inorganic materials 0.000 description 15
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 125000004093 cyano group Chemical group *C#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
• 125000004433 nitrogen atom Chemical group N* 0.000 description 11
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 125000005842 heteroatom Chemical group 0.000 description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
• 150000004702 methyl esters Chemical class 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• 230000000694 effects Effects 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 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 8
• 238000004458 analytical method Methods 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 239000003814 drug Substances 0.000 description 8
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
• 238000005406 washing Methods 0.000 description 8
• 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 7
• 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 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
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 150000002431 hydrogen Chemical class 0.000 description 7
• 239000003446 ligand Substances 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• 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
• 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 6
• 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 6
• 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 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
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
• 239000005457 ice water Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 239000012047 saturated solution Substances 0.000 description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 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
• 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
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• 210000001789 adipocyte Anatomy 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
• 125000004474 heteroalkylene group Chemical group 0.000 description 5
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
• 230000004054 inflammatory process Effects 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 239000000126 substance Substances 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
• 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 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
• 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 4
• SKWDIXBVQATQSG-UHFFFAOYSA-N 2-chloro-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(C(O)=O)=C1 SKWDIXBVQATQSG-UHFFFAOYSA-N 0.000 description 4
• AWOQNJSBSLXMSV-UHFFFAOYSA-N 3,5-dichloro-4-(6-methylquinolin-3-yl)oxyaniline Chemical compound C=1C2=CC(C)=CC=C2N=CC=1OC1=C(Cl)C=C(N)C=C1Cl AWOQNJSBSLXMSV-UHFFFAOYSA-N 0.000 description 4
• BKQZRDFPKRDXQQ-UHFFFAOYSA-N 3-[4-[(6-amino-1,3-benzothiazol-2-yl)oxy]-3-chlorophenyl]-2-chloro-4-(trifluoromethyl)benzenesulfonamide Chemical compound NC1=CC2=C(N=C(S2)OC2=C(C=C(C=C2)C=2C(=C(C=CC=2C(F)(F)F)S(=O)(=O)N)Cl)Cl)C=C1 BKQZRDFPKRDXQQ-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
• BSNXPXPWIJKKDH-UHFFFAOYSA-N 6-methylquinolin-3-ol Chemical compound N1=CC(O)=CC2=CC(C)=CC=C21 BSNXPXPWIJKKDH-UHFFFAOYSA-N 0.000 description 4
• 229940123208 Biguanide Drugs 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
• 239000012190 activator Substances 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 239000003472 antidiabetic agent Substances 0.000 description 4
• 150000004283 biguanides Chemical class 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• 230000004069 differentiation Effects 0.000 description 4
• 239000003480 eluent Substances 0.000 description 4
• 108020001507 fusion proteins Proteins 0.000 description 4
• 102000037865 fusion proteins Human genes 0.000 description 4
• 239000002198 insoluble material Substances 0.000 description 4
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 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 4
• MKFVLMCDXXXACL-UHFFFAOYSA-N n-[3,5-bis[(5-chloro-1,3-benzothiazol-2-yl)oxy]phenyl]-2,4-dichlorobenzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC(OC=2SC3=CC=C(Cl)C=C3N=2)=CC(OC=2SC3=CC=C(Cl)C=C3N=2)=C1 MKFVLMCDXXXACL-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 150000002828 nitro derivatives Chemical class 0.000 description 4
• 239000008194 pharmaceutical composition Substances 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 230000019491 signal transduction Effects 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• 229940124530 sulfonamide Drugs 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 239000011593 sulfur Substances 0.000 description 4
• IBQZISMSQLOUEA-UHFFFAOYSA-N tert-butyl n-[3,5-bis[(5-chloro-1,3-benzothiazol-2-yl)oxy]phenyl]carbamate Chemical compound ClC1=CC=C2SC(OC=3C=C(OC=4SC5=CC=C(Cl)C=C5N=4)C=C(C=3)NC(=O)OC(C)(C)C)=NC2=C1 IBQZISMSQLOUEA-UHFFFAOYSA-N 0.000 description 4
• JJWANONAOYNRME-UHFFFAOYSA-N 2,4-dichloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1Cl JJWANONAOYNRME-UHFFFAOYSA-N 0.000 description 3
• DFBKCDYLPLBSJP-UHFFFAOYSA-N 2,4-dichloro-5-methylbenzenesulfonyl chloride Chemical compound CC1=CC(S(Cl)(=O)=O)=C(Cl)C=C1Cl DFBKCDYLPLBSJP-UHFFFAOYSA-N 0.000 description 3
• LHUHAARPMJISMM-UHFFFAOYSA-N 2,5-dichloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(Cl)=NC2=C1 LHUHAARPMJISMM-UHFFFAOYSA-N 0.000 description 3
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
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