JP2016518428A5 - - Google Patents
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- JP2016518428A5 JP2016518428A5 JP2016513346A JP2016513346A JP2016518428A5 JP 2016518428 A5 JP2016518428 A5 JP 2016518428A5 JP 2016513346 A JP2016513346 A JP 2016513346A JP 2016513346 A JP2016513346 A JP 2016513346A JP 2016518428 A5 JP2016518428 A5 JP 2016518428A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- hydroxypyridin
- sulfonamide
- methanesulfonamide
- dichlorophenyl
- Prior art date
- 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.)
- Granted
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- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- -1 3-hydroxy-4-pyridazinyl Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- JPUKVENJJAUFEC-UHFFFAOYSA-N n-(3-hydroxypyridin-2-yl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound OC1=CC=CN=C1NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 JPUKVENJJAUFEC-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- VEHNLECJKJMMJX-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-N-(4-oxo-1H-pyridin-3-yl)methanesulfonamide Chemical compound OC1=C(NS(=O)(=O)CC2=C(Cl)C=C(Cl)C=C2)C=NC=C1 VEHNLECJKJMMJX-UHFFFAOYSA-N 0.000 claims 1
- DOYSAKLCJQENDT-UHFFFAOYSA-N 1-(2-chloro-5-cyanophenyl)-N-(2-chloro-5-hydroxypyrimidin-4-yl)methanesulfonamide Chemical compound Oc1cnc(Cl)nc1NS(=O)(=O)Cc1cc(ccc1Cl)C#N DOYSAKLCJQENDT-UHFFFAOYSA-N 0.000 claims 1
- UTYORXRCKZULIL-UHFFFAOYSA-N 1-(2-chloro-5-cyanophenyl)-n-(6-chloro-4-oxo-1h-pyridazin-3-yl)methanesulfonamide Chemical compound N1C(Cl)=CC(=O)C(NS(=O)(=O)CC=2C(=CC=C(C=2)C#N)Cl)=N1 UTYORXRCKZULIL-UHFFFAOYSA-N 0.000 claims 1
- ICQVOLPESKBOCO-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-(6-methylsulfonyl-4-oxo-1h-pyridazin-3-yl)methanesulfonamide Chemical compound N1C(S(=O)(=O)C)=CC(=O)C(NS(=O)(=O)CC=2C(=CC=CC=2)Cl)=N1 ICQVOLPESKBOCO-UHFFFAOYSA-N 0.000 claims 1
- RWYRVCXMOXEJPF-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-N-[4-oxo-6-(trifluoromethyl)-1H-pyridin-3-yl]methanesulfonamide Chemical compound OC1=C(NS(=O)(=O)CC2=CC(Cl)=C(Cl)C=C2)C=NC(=C1)C(F)(F)F RWYRVCXMOXEJPF-UHFFFAOYSA-N 0.000 claims 1
- UJGYXTCIWSCRIG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-N-[5-hydroxy-2-(trifluoromethyl)pyrimidin-4-yl]methanesulfonamide Chemical compound ClC=1C=C(C=CC=1Cl)CS(=O)(=O)NC1=NC(=NC=C1O)C(F)(F)F UJGYXTCIWSCRIG-UHFFFAOYSA-N 0.000 claims 1
- CTNSKTHPQMEBKR-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-n-(6-methylsulfonyl-4-oxo-1h-pyridazin-3-yl)methanesulfonamide Chemical compound N1C(S(=O)(=O)C)=CC(=O)C(NS(=O)(=O)CC=2C=C(F)C(F)=CC=2)=N1 CTNSKTHPQMEBKR-UHFFFAOYSA-N 0.000 claims 1
- ICJWYOPJJOCLMY-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-(3-hydroxy-5-methylsulfonylpyridin-2-yl)methanesulfonamide Chemical compound CS(=O)(=O)C1=CN=C(NS(=O)(=O)CC2=CC(Cl)=CC(Cl)=C2)C(O)=C1 ICJWYOPJJOCLMY-UHFFFAOYSA-N 0.000 claims 1
- OKGTXONRYBIZIL-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-(3-hydroxypyridin-4-yl)methanesulfonamide Chemical compound OC1=C(NS(=O)(=O)CC2=CC(Cl)=CC(Cl)=C2)C=CN=C1 OKGTXONRYBIZIL-UHFFFAOYSA-N 0.000 claims 1
- RMCKRTNOEGCEMD-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-(4-oxo-1H-pyridin-3-yl)methanesulfonamide Chemical compound OC1=C(NS(=O)(=O)CC2=CC(Cl)=CC(Cl)=C2)C=NC=C1 RMCKRTNOEGCEMD-UHFFFAOYSA-N 0.000 claims 1
- XKLNZKKWMSTMEF-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-(5-ethylsulfonyl-3-hydroxypyridin-2-yl)methanesulfonamide Chemical compound CCS(=O)(=O)C1=CN=C(NS(=O)(=O)CC2=CC(Cl)=CC(Cl)=C2)C(O)=C1 XKLNZKKWMSTMEF-UHFFFAOYSA-N 0.000 claims 1
- BCUJHQFDVFOSKC-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-(6-ethylsulfonyl-2-oxo-1H-pyridin-3-yl)methanesulfonamide Chemical compound CCS(=O)(=O)C1=CC=C(NS(=O)(=O)CC2=CC(Cl)=CC(Cl)=C2)C(O)=N1 BCUJHQFDVFOSKC-UHFFFAOYSA-N 0.000 claims 1
- DWTXOMHBGVCKKW-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-[5-hydroxy-2-(trifluoromethyl)pyrimidin-4-yl]methanesulfonamide Chemical compound ClC=1C=C(C=C(C=1)Cl)CS(=O)(=O)NC1=NC(=NC=C1O)C(F)(F)F DWTXOMHBGVCKKW-UHFFFAOYSA-N 0.000 claims 1
- MLKJZMPSJOINOJ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-N-[6-(3-hydroxypropylsulfonyl)-4-oxo-1H-pyridazin-3-yl]methanesulfonamide Chemical compound OCCCS(=O)(=O)C1=CC(O)=C(NS(=O)(=O)CC2=CC(Cl)=CC(Cl)=C2)N=N1 MLKJZMPSJOINOJ-UHFFFAOYSA-N 0.000 claims 1
- SVSRUBJJXNRUNV-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-n-(6-ethylsulfonyl-4-oxo-1h-pyridazin-3-yl)methanesulfonamide Chemical compound N1C(S(=O)(=O)CC)=CC(=O)C(NS(=O)(=O)CC=2C=C(Cl)C=C(Cl)C=2)=N1 SVSRUBJJXNRUNV-UHFFFAOYSA-N 0.000 claims 1
- OFPXRDIIWHLCII-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-n-(6-methylsulfonyl-2-oxo-1h-pyrazin-3-yl)methanesulfonamide Chemical compound O=C1NC(S(=O)(=O)C)=CN=C1NS(=O)(=O)CC1=CC(Cl)=CC(Cl)=C1 OFPXRDIIWHLCII-UHFFFAOYSA-N 0.000 claims 1
- NQYKJLDYIFCZPM-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-n-(6-methylsulfonyl-4-oxo-1h-pyridazin-3-yl)methanesulfonamide Chemical compound N1C(S(=O)(=O)C)=CC(=O)C(NS(=O)(=O)CC=2C=C(Cl)C=C(Cl)C=2)=N1 NQYKJLDYIFCZPM-UHFFFAOYSA-N 0.000 claims 1
- MJBMPRVXOLYRER-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-n-[4-oxo-6-(trifluoromethyl)-1h-pyridin-3-yl]methanesulfonamide Chemical compound N1C(C(F)(F)F)=CC(=O)C(NS(=O)(=O)CC=2C=C(Cl)C=C(Cl)C=2)=C1 MJBMPRVXOLYRER-UHFFFAOYSA-N 0.000 claims 1
- PMVKNZVUFSNQMC-UHFFFAOYSA-N 1-(3-chloro-5-cyanophenyl)-N-(6-chloro-4-oxo-1H-pyridazin-3-yl)methanesulfonamide Chemical compound Oc1cc(Cl)nnc1NS(=O)(=O)Cc1cc(Cl)cc(c1)C#N PMVKNZVUFSNQMC-UHFFFAOYSA-N 0.000 claims 1
- MGUPDRHILDSXNQ-UHFFFAOYSA-N 1-(3-chloro-5-cyanophenyl)-n-(5-chloro-3-hydroxypyridin-2-yl)methanesulfonamide Chemical compound OC1=CC(Cl)=CN=C1NS(=O)(=O)CC1=CC(Cl)=CC(C#N)=C1 MGUPDRHILDSXNQ-UHFFFAOYSA-N 0.000 claims 1
- IDTROZMNKNSSPR-UHFFFAOYSA-N 1-(3-chloro-5-ethylsulfanylphenyl)-N-(6-chloro-2-oxo-1H-pyridin-3-yl)methanesulfonamide Chemical compound CCSc1cc(Cl)cc(CS(=O)(=O)Nc2ccc(Cl)nc2O)c1 IDTROZMNKNSSPR-UHFFFAOYSA-N 0.000 claims 1
- FAXYLVXBKNVCKU-UHFFFAOYSA-N 1-(3-chloro-5-fluorophenyl)-N-(5-chloro-3-hydroxypyridin-2-yl)methanesulfonamide Chemical compound Oc1cc(Cl)cnc1NS(=O)(=O)Cc1cc(F)cc(Cl)c1 FAXYLVXBKNVCKU-UHFFFAOYSA-N 0.000 claims 1
- LIGIRDISLRWNAM-UHFFFAOYSA-N 1-(3-chloro-5-fluorophenyl)-n-(6-chloro-4-oxo-1h-pyridazin-3-yl)methanesulfonamide Chemical compound FC1=CC(Cl)=CC(CS(=O)(=O)NC=2C(C=C(Cl)NN=2)=O)=C1 LIGIRDISLRWNAM-UHFFFAOYSA-N 0.000 claims 1
- ZYKDUUXGSSDPSY-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-(6-ethylsulfonyl-2-oxo-1h-pyrazin-3-yl)methanesulfonamide Chemical compound O=C1NC(S(=O)(=O)CC)=CN=C1NS(=O)(=O)CC1=CC=CC(Cl)=C1 ZYKDUUXGSSDPSY-UHFFFAOYSA-N 0.000 claims 1
- CWOYNHCVVRXXKW-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)-N-(5-chloro-3-hydroxypyridin-2-yl)methanesulfonamide Chemical compound OC1=CC(Cl)=CN=C1NS(=O)(=O)CC1=C(F)C=CC(Cl)=C1 CWOYNHCVVRXXKW-UHFFFAOYSA-N 0.000 claims 1
- GHOIZZRUBGGBHC-UHFFFAOYSA-N 1-(5-chloro-6-methoxypyridin-3-yl)-N-(6-chloro-2-oxo-1H-pyridin-3-yl)methanesulfonamide Chemical compound ClC1=CC=C(C(=N1)O)NS(=O)(=O)CC=1C=NC(=C(C1)Cl)OC GHOIZZRUBGGBHC-UHFFFAOYSA-N 0.000 claims 1
- OTVAEFIXJLOWRX-UHFFFAOYSA-N 2,2-dichloro-n-[1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide Chemical group CS(=O)(=O)C1=CC=C(C(O)C(CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-UHFFFAOYSA-N 0.000 claims 1
- SLSNOSPCTVDVJA-UHFFFAOYSA-N 2,5-dichloro-n-(4-oxo-1h-pyridin-3-yl)thiophene-3-sulfonamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC=2C(C=CNC=2)=O)=C1Cl SLSNOSPCTVDVJA-UHFFFAOYSA-N 0.000 claims 1
- VVVWFUDYRQSLFQ-UHFFFAOYSA-N 2,5-dichloro-n-(5-chloro-2-oxo-1h-pyridin-3-yl)thiophene-3-sulfonamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC=2C(NC=C(Cl)C=2)=O)=C1Cl VVVWFUDYRQSLFQ-UHFFFAOYSA-N 0.000 claims 1
- YJWWEBMNZMKNEU-UHFFFAOYSA-N 2,5-dichloro-n-(5-chloro-3-hydroxypyridin-2-yl)thiophene-3-sulfonamide Chemical compound OC1=CC(Cl)=CN=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1 YJWWEBMNZMKNEU-UHFFFAOYSA-N 0.000 claims 1
- MYYZURUVQLJGLJ-UHFFFAOYSA-N 2,5-dichloro-n-(6-chloro-4-oxo-1h-pyridazin-3-yl)thiophene-3-sulfonamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC=2C(C=C(Cl)NN=2)=O)=C1Cl MYYZURUVQLJGLJ-UHFFFAOYSA-N 0.000 claims 1
- YKWXLFLVIXAJLM-UHFFFAOYSA-N 2,5-dichloro-n-(6-chloro-4-oxo-1h-pyridin-3-yl)thiophene-3-sulfonamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC=2C(C=C(Cl)NC=2)=O)=C1Cl YKWXLFLVIXAJLM-UHFFFAOYSA-N 0.000 claims 1
- BNCLRARIZOFSJK-UHFFFAOYSA-N 2-chloro-N-(6-chloro-4-oxo-1H-pyridazin-3-yl)-4-cyanobenzenesulfonamide Chemical compound ClC1=C(C=CC(=C1)C#N)S(=O)(=O)NC=1N=NC(=CC1O)Cl BNCLRARIZOFSJK-UHFFFAOYSA-N 0.000 claims 1
- FCDDNYSIVRKTCJ-UHFFFAOYSA-N 3,4-dichloro-N-(2-chloro-5-hydroxypyrimidin-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC1Cl)S(=O)(=O)NC1=NC(=NC=C1O)Cl FCDDNYSIVRKTCJ-UHFFFAOYSA-N 0.000 claims 1
- BCNDJAIPEZAECP-UHFFFAOYSA-N 3,4-dichloro-N-(5-chloro-3-hydroxypyridin-2-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC1Cl)S(=O)(=O)NC1=NC=C(C=C1O)Cl BCNDJAIPEZAECP-UHFFFAOYSA-N 0.000 claims 1
- BLPYPBPBZUIRGB-UHFFFAOYSA-N 3,4-dichloro-N-(6-chloro-2-oxo-1H-pyridin-3-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC1Cl)S(=O)(=O)NC=1C(=NC(=CC1)Cl)O BLPYPBPBZUIRGB-UHFFFAOYSA-N 0.000 claims 1
- DYCQBJGGORQMHI-UHFFFAOYSA-N 3,4-dichloro-N-(6-chloro-4-oxo-1H-pyridazin-3-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=CC1Cl)S(=O)(=O)NC=1N=NC(=CC1O)Cl DYCQBJGGORQMHI-UHFFFAOYSA-N 0.000 claims 1
- CTWLFJWIGHROSY-UHFFFAOYSA-N 3,4-dichloro-n-(4-oxo-1h-pyridin-3-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CNC=CC1=O CTWLFJWIGHROSY-UHFFFAOYSA-N 0.000 claims 1
- NHSNDDAWGRHBFN-UHFFFAOYSA-N 3,4-difluoro-n-(4-oxo-1h-pyridin-3-yl)benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1S(=O)(=O)NC1=CNC=CC1=O NHSNDDAWGRHBFN-UHFFFAOYSA-N 0.000 claims 1
- QRKAVNWNTFRNCH-UHFFFAOYSA-N 3,5-dichloro-N-(2-chloro-3-hydroxypyridin-4-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=C(C1)Cl)S(=O)(=O)NC1=C(C(=NC=C1)Cl)O QRKAVNWNTFRNCH-UHFFFAOYSA-N 0.000 claims 1
- MCKLUHOSCJNXRY-UHFFFAOYSA-N 3,5-dichloro-N-(5-chloro-3-hydroxypyridin-2-yl)benzenesulfonamide Chemical compound Oc1cc(Cl)cnc1NS(=O)(=O)c1cc(Cl)cc(Cl)c1 MCKLUHOSCJNXRY-UHFFFAOYSA-N 0.000 claims 1
- JZWLPBFSTZGOQD-UHFFFAOYSA-N 3,5-dichloro-N-(5-cyano-4-oxo-1H-pyridin-3-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=C(C1)Cl)S(=O)(=O)NC=1C=NC=C(C1O)C#N JZWLPBFSTZGOQD-UHFFFAOYSA-N 0.000 claims 1
- HAGDOXZAIQGDPG-UHFFFAOYSA-N 3,5-dichloro-N-(6-chloro-4-oxo-1H-pyridin-3-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=C(C1)Cl)S(=O)(=O)NC=1C=NC(=CC1O)Cl HAGDOXZAIQGDPG-UHFFFAOYSA-N 0.000 claims 1
- YHAQVDYRZBARGJ-UHFFFAOYSA-N 3,5-dichloro-N-(6-ethylsulfonyl-2-oxo-1H-pyridin-3-yl)benzenesulfonamide Chemical compound CCS(=O)(=O)c1ccc(NS(=O)(=O)c2cc(Cl)cc(Cl)c2)c(O)n1 YHAQVDYRZBARGJ-UHFFFAOYSA-N 0.000 claims 1
- LKGUUTSCHRBDGL-UHFFFAOYSA-N 3,5-dichloro-N-(6-methylsulfonyl-2-oxo-1H-pyrazin-3-yl)benzenesulfonamide Chemical compound CS(=O)(=O)c1cnc(NS(=O)(=O)c2cc(Cl)cc(Cl)c2)c(O)n1 LKGUUTSCHRBDGL-UHFFFAOYSA-N 0.000 claims 1
- MFOOJBYTSPRWEI-UHFFFAOYSA-N 3,5-dichloro-N-(6-methylsulfonyl-4-oxo-1H-pyridazin-3-yl)benzenesulfonamide Chemical compound ClC=1C=C(C=C(C1)Cl)S(=O)(=O)NC=1N=NC(=CC1O)S(=O)(=O)C MFOOJBYTSPRWEI-UHFFFAOYSA-N 0.000 claims 1
- XUCLWPUKHUHMOU-UHFFFAOYSA-N 3,5-dichloro-N-(6-methylsulfonyl-4-oxo-1H-pyridin-3-yl)benzenesulfonamide Chemical compound CS(=O)(=O)c1cc(O)c(NS(=O)(=O)c2cc(Cl)cc(Cl)c2)cn1 XUCLWPUKHUHMOU-UHFFFAOYSA-N 0.000 claims 1
- VFNCEUUAQRLOSU-UHFFFAOYSA-N 3,5-dichloro-n-(2-chloro-5-hydroxypyrimidin-4-yl)benzenesulfonamide Chemical compound OC1=CN=C(Cl)N=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 VFNCEUUAQRLOSU-UHFFFAOYSA-N 0.000 claims 1
- KUXNJQZRSHVQOS-UHFFFAOYSA-N 3,5-dichloro-n-(5-chloro-4-oxo-1h-pyridin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC=2C(C(Cl)=CNC=2)=O)=C1 KUXNJQZRSHVQOS-UHFFFAOYSA-N 0.000 claims 1
- DFFIUNTUEDBUST-UHFFFAOYSA-N 3,5-dichloro-n-(6-chloro-4-oxo-1h-pyridazin-3-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC=2C(C=C(Cl)NN=2)=O)=C1 DFFIUNTUEDBUST-UHFFFAOYSA-N 0.000 claims 1
- CSAXMZWBDSWQMB-UHFFFAOYSA-N 3-[(5-chloro-4-oxo-1h-pyridin-3-yl)sulfamoyl]-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC(S(=O)(=O)NC=2C(C(Cl)=CNC=2)=O)=C1 CSAXMZWBDSWQMB-UHFFFAOYSA-N 0.000 claims 1
- WTXJPKUNXPXISR-UHFFFAOYSA-N 3-[(6-bromo-2-oxo-1H-pyrazin-3-yl)sulfamoyl]-N,N-diethylbenzamide Chemical compound CCN(CC)C(=O)c1cccc(c1)S(=O)(=O)Nc1ncc(Br)nc1O WTXJPKUNXPXISR-UHFFFAOYSA-N 0.000 claims 1
- UFYCENOCIZIQBJ-UHFFFAOYSA-N 3-[(6-chloro-4-oxo-1H-pyridazin-3-yl)sulfamoyl]-N,N-diethylbenzamide Chemical compound CCN(CC)C(=O)c1cccc(c1)S(=O)(=O)Nc1nnc(Cl)cc1O UFYCENOCIZIQBJ-UHFFFAOYSA-N 0.000 claims 1
- DRPSJKKYPMCHGO-UHFFFAOYSA-N 3-bromo-n-(5-bromo-4-oxo-1h-pyridin-3-yl)-4-methoxybenzenesulfonamide Chemical compound C1=C(Br)C(OC)=CC=C1S(=O)(=O)NC1=CNC=C(Br)C1=O DRPSJKKYPMCHGO-UHFFFAOYSA-N 0.000 claims 1
- SNGRHDFAUDTIQL-UHFFFAOYSA-N 3-chloro-4-[(6-chloro-4-oxo-1H-pyridazin-3-yl)sulfamoyl]-N,N-diethylbenzamide Chemical compound CCN(CC)C(=O)c1ccc(c(Cl)c1)S(=O)(=O)Nc1nnc(Cl)cc1O SNGRHDFAUDTIQL-UHFFFAOYSA-N 0.000 claims 1
- KMHXCSAVNAJDCY-UHFFFAOYSA-N 3-chloro-5-[(6-chloro-4-oxo-1H-pyridazin-3-yl)sulfamoylmethyl]-N,N-diethylbenzamide Chemical compound CCN(CC)C(=O)c1cc(Cl)cc(CS(=O)(=O)Nc2nnc(Cl)cc2O)c1 KMHXCSAVNAJDCY-UHFFFAOYSA-N 0.000 claims 1
- SOTHPZUGJRTUIP-UHFFFAOYSA-N 3-chloro-5-fluoro-N-[4-oxo-6-(trifluoromethyl)-1H-pyridazin-3-yl]benzenesulfonamide Chemical compound Oc1cc(nnc1NS(=O)(=O)c1cc(F)cc(Cl)c1)C(F)(F)F SOTHPZUGJRTUIP-UHFFFAOYSA-N 0.000 claims 1
- HDURJOJFTUYJLE-UHFFFAOYSA-N 3-chloro-5-fluoro-N-[5-hydroxy-2-(trifluoromethyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound ClC=1C=C(C=C(C=1)F)S(=O)(=O)NC1=NC(=NC=C1O)C(F)(F)F HDURJOJFTUYJLE-UHFFFAOYSA-N 0.000 claims 1
- YUKDHINQZSVGTR-UHFFFAOYSA-N 3-chloro-N-(6-chloro-4-oxo-1H-pyridazin-3-yl)-4-fluorobenzenesulfonamide Chemical compound ClC=1C=C(C=CC1F)S(=O)(=O)NC=1N=NC(=CC1O)Cl YUKDHINQZSVGTR-UHFFFAOYSA-N 0.000 claims 1
- NWRJOMNXRPGVLM-UHFFFAOYSA-N 3-chloro-N-(6-chloro-4-oxo-1H-pyridazin-3-yl)-5-fluorobenzenesulfonamide Chemical compound ClC=1C=C(C=C(C1)F)S(=O)(=O)NC=1N=NC(=CC1O)Cl NWRJOMNXRPGVLM-UHFFFAOYSA-N 0.000 claims 1
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| CA2786289A1 (en) | 2010-01-06 | 2011-07-14 | Joseph P. Errico | Methods and compositions of targeted drug development |
| US9006433B2 (en) * | 2010-04-21 | 2015-04-14 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
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