JP2009524678A5 - - Google Patents
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- JP2009524678A5 JP2009524678A5 JP2008552424A JP2008552424A JP2009524678A5 JP 2009524678 A5 JP2009524678 A5 JP 2009524678A5 JP 2008552424 A JP2008552424 A JP 2008552424A JP 2008552424 A JP2008552424 A JP 2008552424A JP 2009524678 A5 JP2009524678 A5 JP 2009524678A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- thiophen
- optionally substituted
- difluoro
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 35
- -1 thiadiazole-5-carboxylic acid [4- (2-methyl-5-thiazol-2-yl-furan-3-yl) -phenyl] -amide Chemical compound 0.000 claims 22
- 125000001475 halogen functional group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 11
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 11
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 5
- WYYSCGSALKNGNK-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)thiophen-3-yl]phenyl]benzamide Chemical compound CC=1SC(C=2OC=CN=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F WYYSCGSALKNGNK-UHFFFAOYSA-N 0.000 claims 4
- UBSSMFGUCHZQGJ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)furan-3-yl]phenyl]benzamide Chemical compound CC=1OC(C=2SC=CN=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F UBSSMFGUCHZQGJ-UHFFFAOYSA-N 0.000 claims 4
- FOXXSBDVNODXFR-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)thiophen-3-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1SC(C=2OC=CN=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C FOXXSBDVNODXFR-UHFFFAOYSA-N 0.000 claims 4
- YBFYHJUUMVRXFS-UHFFFAOYSA-N 3-methyl-n-[4-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C YBFYHJUUMVRXFS-UHFFFAOYSA-N 0.000 claims 4
- CLIZOUKKYIGODI-UHFFFAOYSA-N 4-methyloxadiazole-5-carboxylic acid Chemical compound CC=1N=NOC=1C(O)=O CLIZOUKKYIGODI-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- VJUSEJIBZTZGOL-UHFFFAOYSA-N methyl 5-[4-[(2,6-difluorobenzoyl)amino]phenyl]-4-methyl-1,3-thiazole-2-carboxylate Chemical compound S1C(C(=O)OC)=NC(C)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VJUSEJIBZTZGOL-UHFFFAOYSA-N 0.000 claims 4
- MALCUNUUEAWQQQ-UHFFFAOYSA-N methyl 5-[4-[(2,6-difluorobenzoyl)amino]phenyl]-4-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F MALCUNUUEAWQQQ-UHFFFAOYSA-N 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- YKXVQWJCACQYTR-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-3-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]urea Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)NC1=C(F)C=CC=C1F YKXVQWJCACQYTR-UHFFFAOYSA-N 0.000 claims 2
- SCMWFMZOIDPSFD-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-3-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]urea Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)NC1=C(F)C=CC=C1F SCMWFMZOIDPSFD-UHFFFAOYSA-N 0.000 claims 2
- MNTPYSYREGZGFV-UHFFFAOYSA-N 1-(3-fluoropyridin-4-yl)-3-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]urea Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1F MNTPYSYREGZGFV-UHFFFAOYSA-N 0.000 claims 2
- XVQJJZMHUKKPBO-UHFFFAOYSA-N 1-methyl-n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]pyrrole-2-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=CN1C XVQJJZMHUKKPBO-UHFFFAOYSA-N 0.000 claims 2
- UOTCZQATGPKGPN-UHFFFAOYSA-N 2,6-difluoro-n-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]benzamide Chemical compound N1=CSC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C UOTCZQATGPKGPN-UHFFFAOYSA-N 0.000 claims 2
- OMIWEKCZTBZHCO-UHFFFAOYSA-N 2,6-difluoro-n-[4-(4-methyl-2-morpholin-4-yl-1,3-thiazol-5-yl)phenyl]benzamide Chemical compound CC=1N=C(N2CCOCC2)SC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F OMIWEKCZTBZHCO-UHFFFAOYSA-N 0.000 claims 2
- KKXSDIJYVBPQHH-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3-oxazol-5-yl)thiophen-3-yl]phenyl]benzamide Chemical compound CC=1SC(C=2OC=NC=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F KKXSDIJYVBPQHH-UHFFFAOYSA-N 0.000 claims 2
- VAVCVYFBYJGTAW-UHFFFAOYSA-N 2,6-difluoro-n-[4-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]phenyl]benzamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VAVCVYFBYJGTAW-UHFFFAOYSA-N 0.000 claims 2
- BXXSXUNGYWEENS-UHFFFAOYSA-N 2,6-difluoro-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]benzamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BXXSXUNGYWEENS-UHFFFAOYSA-N 0.000 claims 2
- VSPGFXQQJAMOPO-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-2-(1,3-oxazol-2-yl)-1,3-thiazol-5-yl]phenyl]benzamide Chemical compound CC=1N=C(C=2OC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VSPGFXQQJAMOPO-UHFFFAOYSA-N 0.000 claims 2
- ONUMOWYRZRJYOK-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-(1,3-oxazol-2-yl)thiophen-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C=C(SC=2)C=2OC=CN=2)C=C1 ONUMOWYRZRJYOK-UHFFFAOYSA-N 0.000 claims 2
- NLQYAINTFBUWPL-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-(1,3-oxazol-5-yl)thiophen-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C=C(SC=2)C=2OC=NC=2)C=C1 NLQYAINTFBUWPL-UHFFFAOYSA-N 0.000 claims 2
- GOBZDEQKITVFIS-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-(furan-2-yl)-2-methylthiophen-3-yl]phenyl]benzamide Chemical compound CC=1SC(C=2OC=CC=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F GOBZDEQKITVFIS-UHFFFAOYSA-N 0.000 claims 2
- IETXJKHJJASRGT-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-(furan-3-yl)-2-methylthiophen-3-yl]phenyl]benzamide Chemical compound CC=1SC(C2=COC=C2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F IETXJKHJJASRGT-UHFFFAOYSA-N 0.000 claims 2
- LOFGHTSTMGFTCK-UHFFFAOYSA-N 2,6-difluoro-n-[4-[5-(furan-3-yl)thiophen-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C=C(SC=2)C2=COC=C2)C=C1 LOFGHTSTMGFTCK-UHFFFAOYSA-N 0.000 claims 2
- HYTZVPMLOFDSDK-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]benzamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F HYTZVPMLOFDSDK-UHFFFAOYSA-N 0.000 claims 2
- GYKPMYJAPTZVHH-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F GYKPMYJAPTZVHH-UHFFFAOYSA-N 0.000 claims 2
- VZDOQVKFDKBJBE-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-methyl-5-(1,3,4-oxadiazol-2-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2OC=NN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VZDOQVKFDKBJBE-UHFFFAOYSA-N 0.000 claims 2
- BZFYYTDRBCWRBM-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BZFYYTDRBCWRBM-UHFFFAOYSA-N 0.000 claims 2
- HKDURICRSXXGMI-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F HKDURICRSXXGMI-UHFFFAOYSA-N 0.000 claims 2
- IRBQNAUMMUUTTE-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]benzamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=CC=C1F IRBQNAUMMUUTTE-UHFFFAOYSA-N 0.000 claims 2
- CKCUVYREMLVMLD-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=CC=C1F CKCUVYREMLVMLD-UHFFFAOYSA-N 0.000 claims 2
- JYLNGRCSHMKZFG-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[5-[3-methyl-5-(1,3,4-oxadiazol-2-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2OC=NN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=CC=C1F JYLNGRCSHMKZFG-UHFFFAOYSA-N 0.000 claims 2
- ATUXAQXPCUYCEB-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[5-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=CC=C1F ATUXAQXPCUYCEB-UHFFFAOYSA-N 0.000 claims 2
- HQXYTDOBPHDLKV-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[5-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]benzamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=CC=C1F HQXYTDOBPHDLKV-UHFFFAOYSA-N 0.000 claims 2
- CABOPYJGLIHNJX-UHFFFAOYSA-N 2-methoxyethyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OCCOC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 CABOPYJGLIHNJX-UHFFFAOYSA-N 0.000 claims 2
- SLWSJZJVONOHBU-UHFFFAOYSA-N 2-methyl-n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]pyrazole-3-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NN1C SLWSJZJVONOHBU-UHFFFAOYSA-N 0.000 claims 2
- YESCYMQTYYOHKY-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)furan-3-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1OC(C=2SC=CN=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F YESCYMQTYYOHKY-UHFFFAOYSA-N 0.000 claims 2
- KMFJJSIKGMFPMX-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=NC=C1F KMFJJSIKGMFPMX-UHFFFAOYSA-N 0.000 claims 2
- FKGQYHFDXFZUAB-UHFFFAOYSA-N 3,5-difluoro-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=NC=C1F FKGQYHFDXFZUAB-UHFFFAOYSA-N 0.000 claims 2
- GTKIZSBVRZRZLP-UHFFFAOYSA-N 3,5-difluoro-n-[5-[3-methyl-5-(1,3,4-oxadiazol-2-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=NC=C1F GTKIZSBVRZRZLP-UHFFFAOYSA-N 0.000 claims 2
- TYRAHOLIXRSUMC-UHFFFAOYSA-N 3,5-difluoro-n-[5-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(F)C=NC=C1F TYRAHOLIXRSUMC-UHFFFAOYSA-N 0.000 claims 2
- NEYMYSWSKAUKEA-UHFFFAOYSA-N 3-fluoro-5-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)furan-3-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1OC(C=2OC=CN=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(C)C=NC=C1F NEYMYSWSKAUKEA-UHFFFAOYSA-N 0.000 claims 2
- VRBCBWGCJZPWNU-UHFFFAOYSA-N 3-fluoro-5-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=NC=C1F VRBCBWGCJZPWNU-UHFFFAOYSA-N 0.000 claims 2
- SJTUGOQXIQCEGV-UHFFFAOYSA-N 3-fluoro-5-methyl-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=C(C)C=NC=C1F SJTUGOQXIQCEGV-UHFFFAOYSA-N 0.000 claims 2
- AHDYGWPDKLCIBQ-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)furan-3-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1OC(C=2SC=CN=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F AHDYGWPDKLCIBQ-UHFFFAOYSA-N 0.000 claims 2
- AWEIDKMWUHVSTM-UHFFFAOYSA-N 3-fluoro-n-[4-[4-methyl-2-(1,3-oxazol-2-yl)-1,3-thiazol-5-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1N=C(C=2OC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F AWEIDKMWUHVSTM-UHFFFAOYSA-N 0.000 claims 2
- NILCWRWPCGLKMY-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1F NILCWRWPCGLKMY-UHFFFAOYSA-N 0.000 claims 2
- VZAGTGXQBDBNLB-UHFFFAOYSA-N 3-fluoro-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1F VZAGTGXQBDBNLB-UHFFFAOYSA-N 0.000 claims 2
- NTBFYSQWMJKSPD-UHFFFAOYSA-N 3-fluoro-n-[5-[3-methyl-5-(1,3,4-oxadiazol-2-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1F NTBFYSQWMJKSPD-UHFFFAOYSA-N 0.000 claims 2
- IATBPPCRDUULEC-UHFFFAOYSA-N 3-fluoro-n-[5-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1F IATBPPCRDUULEC-UHFFFAOYSA-N 0.000 claims 2
- HFBSGPQSVRKCFW-UHFFFAOYSA-N 3-methyl-n-[4-(3-methyl-5-pyridin-3-ylthiophen-2-yl)phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2C=NC=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C HFBSGPQSVRKCFW-UHFFFAOYSA-N 0.000 claims 2
- LAMZJGAAGYQWAA-UHFFFAOYSA-N 3-methyl-n-[4-(3-methyl-5-pyrimidin-4-ylthiophen-2-yl)phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2N=CN=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C LAMZJGAAGYQWAA-UHFFFAOYSA-N 0.000 claims 2
- HETSCJCZMZWQMJ-UHFFFAOYSA-N 3-methyl-n-[4-(3-methyl-5-pyrimidin-5-ylthiophen-2-yl)phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2C=NC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C HETSCJCZMZWQMJ-UHFFFAOYSA-N 0.000 claims 2
- PUHHSLLZMMTMAX-UHFFFAOYSA-N 3-methyl-n-[4-(4-methyl-2-morpholin-4-yl-1,3-thiazol-5-yl)phenyl]pyridine-4-carboxamide Chemical compound CC=1N=C(N2CCOCC2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C PUHHSLLZMMTMAX-UHFFFAOYSA-N 0.000 claims 2
- ZYZPHIVQCALSRL-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-5-yl)thiophen-3-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1SC(C=2OC=NC=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C ZYZPHIVQCALSRL-UHFFFAOYSA-N 0.000 claims 2
- WLJHFNBVHVAEJP-UHFFFAOYSA-N 3-methyl-n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]-1h-pyrrole-2-carboxamide Chemical compound C1=CNC(C(=O)NC=2C=CC(=CC=2)C2=C(C=C(S2)C=2ON=CC=2)C)=C1C WLJHFNBVHVAEJP-UHFFFAOYSA-N 0.000 claims 2
- FAZLFNZSTZTKRO-UHFFFAOYSA-N 3-methyl-n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C FAZLFNZSTZTKRO-UHFFFAOYSA-N 0.000 claims 2
- WTCUIIZBHGWZKX-UHFFFAOYSA-N 3-methyl-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C WTCUIIZBHGWZKX-UHFFFAOYSA-N 0.000 claims 2
- GIHDUQJVBKUUQO-UHFFFAOYSA-N 3-methyl-n-[4-[3-methyl-5-(1,3-thiazol-2-yl)thiophen-2-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2SC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C GIHDUQJVBKUUQO-UHFFFAOYSA-N 0.000 claims 2
- LYYVKXGKNZGVKD-UHFFFAOYSA-N 3-methyl-n-[4-[4-methyl-2-(1,3-oxazol-2-yl)-1,3-thiazol-5-yl]phenyl]pyridine-4-carboxamide Chemical compound CC=1N=C(C=2OC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C LYYVKXGKNZGVKD-UHFFFAOYSA-N 0.000 claims 2
- BRGOBBDBCBQQKM-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]pyridazine-4-carboxamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=CC=NN=C1C BRGOBBDBCBQQKM-UHFFFAOYSA-N 0.000 claims 2
- LBTLOHJNNSSKBQ-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1SC(C=2ON=CC=2)=CC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C LBTLOHJNNSSKBQ-UHFFFAOYSA-N 0.000 claims 2
- GSLYIRZIASTLAO-UHFFFAOYSA-N 3-methyl-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridazine-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NN=C1C GSLYIRZIASTLAO-UHFFFAOYSA-N 0.000 claims 2
- YXJGEBMXEHCLQX-UHFFFAOYSA-N 3-methyl-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C YXJGEBMXEHCLQX-UHFFFAOYSA-N 0.000 claims 2
- YNJFVGGDRQJYRE-UHFFFAOYSA-N 3-methyl-n-[5-[3-methyl-5-(1,3,4-oxadiazol-2-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C YNJFVGGDRQJYRE-UHFFFAOYSA-N 0.000 claims 2
- LDYXOQJWNNVEOE-UHFFFAOYSA-N 3-methyl-n-[5-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C LDYXOQJWNNVEOE-UHFFFAOYSA-N 0.000 claims 2
- PAZGTNYQTOWXLZ-UHFFFAOYSA-N 3-methyl-n-[5-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C PAZGTNYQTOWXLZ-UHFFFAOYSA-N 0.000 claims 2
- RHORFJIRYBWPJA-UHFFFAOYSA-N 4-chloro-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]-1,3-thiazole-5-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C=1SC=NC=1Cl RHORFJIRYBWPJA-UHFFFAOYSA-N 0.000 claims 2
- FLSQWLWHYDIBPQ-UHFFFAOYSA-N 4-methyl-n-[4-(3-methyl-5-pyridin-2-ylthiophen-2-yl)phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2N=CC=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C FLSQWLWHYDIBPQ-UHFFFAOYSA-N 0.000 claims 2
- CRIHNZZWEPWKAV-UHFFFAOYSA-N 4-methyl-n-[4-(3-methyl-5-pyridin-4-ylthiophen-2-yl)phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2C=CN=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C CRIHNZZWEPWKAV-UHFFFAOYSA-N 0.000 claims 2
- QDFDAROAJLFZKU-UHFFFAOYSA-N 4-methyl-n-[4-(3-methyl-5-pyrimidin-5-ylthiophen-2-yl)phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2C=NC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C QDFDAROAJLFZKU-UHFFFAOYSA-N 0.000 claims 2
- KIFHSJDDGSKKIT-UHFFFAOYSA-N 4-methyl-n-[4-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C KIFHSJDDGSKKIT-UHFFFAOYSA-N 0.000 claims 2
- LUARNLNVJNZXHV-UHFFFAOYSA-N 4-methyl-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]pyrimidine-5-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CN=CN=C1C LUARNLNVJNZXHV-UHFFFAOYSA-N 0.000 claims 2
- OPHXRKCXCQZUHY-UHFFFAOYSA-N 4-methyl-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C OPHXRKCXCQZUHY-UHFFFAOYSA-N 0.000 claims 2
- DIFLVBGBRJYJFE-UHFFFAOYSA-N 4-methyl-n-[4-[4-methyl-2-(1,3-oxazol-2-yl)-1,3-thiazol-5-yl]phenyl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C2=C(N=C(S2)C=2OC=CN=2)C)=C1C DIFLVBGBRJYJFE-UHFFFAOYSA-N 0.000 claims 2
- QOQLEZIVWWLHMI-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)thiophen-3-yl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C2=C(SC(=C2)C=2ON=CC=2)C)=C1C QOQLEZIVWWLHMI-UHFFFAOYSA-N 0.000 claims 2
- QUYSSUAQKGGKRX-UHFFFAOYSA-N 4-methyl-n-[5-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=N1)=CC=C1NC(=O)C=1SN=NC=1C QUYSSUAQKGGKRX-UHFFFAOYSA-N 0.000 claims 2
- ODKNNXGUHSATSH-UHFFFAOYSA-N 4-methyl-n-[5-[3-methyl-5-(1,3,4-oxadiazol-2-yl)thiophen-2-yl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2OC=NN=2)SC=1C(C=N1)=CC=C1NC(=O)C=1SN=NC=1C ODKNNXGUHSATSH-UHFFFAOYSA-N 0.000 claims 2
- BHQCOOVXUDLALR-UHFFFAOYSA-N 4-methyl-n-[5-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=N1)=CC=C1NC(=O)C=1SN=NC=1C BHQCOOVXUDLALR-UHFFFAOYSA-N 0.000 claims 2
- XTCNNYNBZPKKSM-UHFFFAOYSA-N 4-methyl-n-[5-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=N1)=CC=C1NC(=O)C=1SN=NC=1C XTCNNYNBZPKKSM-UHFFFAOYSA-N 0.000 claims 2
- IRWVNKPZGOZNOH-UHFFFAOYSA-N 5-methyl-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]pyrimidine-4-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=NC=NC=C1C IRWVNKPZGOZNOH-UHFFFAOYSA-N 0.000 claims 2
- BAWCGQLFZYCZMO-UHFFFAOYSA-N ethyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methyl-1,3-thiazole-2-carboxylate Chemical compound S1C(C(=O)OCC)=NC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C BAWCGQLFZYCZMO-UHFFFAOYSA-N 0.000 claims 2
- OANGQYWAULSSCC-UHFFFAOYSA-N ethyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methylfuran-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C OANGQYWAULSSCC-UHFFFAOYSA-N 0.000 claims 2
- TVLJVSMXJAHIAB-UHFFFAOYSA-N ethyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OCC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C TVLJVSMXJAHIAB-UHFFFAOYSA-N 0.000 claims 2
- 230000005931 immune cell recruitment Effects 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- ALGLKNDJOSAABE-UHFFFAOYSA-N methyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methoxythiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1OC ALGLKNDJOSAABE-UHFFFAOYSA-N 0.000 claims 2
- VSAYYWCFHUNSNQ-UHFFFAOYSA-N methyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methyl-1,3-oxazole-2-carboxylate Chemical compound O1C(C(=O)OC)=NC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C VSAYYWCFHUNSNQ-UHFFFAOYSA-N 0.000 claims 2
- ACBKSBLMNVCGNN-UHFFFAOYSA-N methyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methyl-1,3-thiazole-2-carboxylate Chemical compound S1C(C(=O)OC)=NC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C ACBKSBLMNVCGNN-UHFFFAOYSA-N 0.000 claims 2
- ABWCBPSIWHRJDK-UHFFFAOYSA-N methyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methylfuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C ABWCBPSIWHRJDK-UHFFFAOYSA-N 0.000 claims 2
- NTNLWSYOFAXBGI-UHFFFAOYSA-N methyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]-5-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1C NTNLWSYOFAXBGI-UHFFFAOYSA-N 0.000 claims 2
- LRZUWRRODQAODP-UHFFFAOYSA-N methyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 LRZUWRRODQAODP-UHFFFAOYSA-N 0.000 claims 2
- LYCOWRFYJATDPH-UHFFFAOYSA-N methyl 4-[4-[(3-fluoropyridine-4-carbonyl)amino]phenyl]-5-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)=C1C LYCOWRFYJATDPH-UHFFFAOYSA-N 0.000 claims 2
- JRYJWXSLFQQXLX-UHFFFAOYSA-N methyl 4-[4-[(3-methylpyridine-4-carbonyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 JRYJWXSLFQQXLX-UHFFFAOYSA-N 0.000 claims 2
- AXXVQOXZDCWEAW-UHFFFAOYSA-N methyl 5-[4-[(2,6-difluorobenzoyl)amino]phenyl]-4-methyl-1,3-oxazole-2-carboxylate Chemical compound O1C(C(=O)OC)=NC(C)=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F AXXVQOXZDCWEAW-UHFFFAOYSA-N 0.000 claims 2
- DFSCLRADUDGVLO-UHFFFAOYSA-N methyl 5-chloro-4-[4-[(2,6-difluorobenzoyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1Cl DFSCLRADUDGVLO-UHFFFAOYSA-N 0.000 claims 2
- KDXJHGVNBJDYCH-UHFFFAOYSA-N methyl 5-methyl-4-[4-[(3-methylpyridine-4-carbonyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1C KDXJHGVNBJDYCH-UHFFFAOYSA-N 0.000 claims 2
- SYALBUWEQXTIRN-UHFFFAOYSA-N methyl 5-methyl-4-[4-[(4-methyl-1,2-thiazole-5-carbonyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C3=C(C=NS3)C)=CC=2)=C1C SYALBUWEQXTIRN-UHFFFAOYSA-N 0.000 claims 2
- BWTHHOGRKUTRQG-UHFFFAOYSA-N methyl 5-methyl-4-[4-[(4-methylthiadiazole-5-carbonyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C3=C(N=NS3)C)=CC=2)=C1C BWTHHOGRKUTRQG-UHFFFAOYSA-N 0.000 claims 2
- SYWHKDGPGLWLKR-UHFFFAOYSA-N n-[(3-fluoropyridin-4-yl)methyl]-4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]aniline Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NCC1=CC=NC=C1F SYWHKDGPGLWLKR-UHFFFAOYSA-N 0.000 claims 2
- MBZNHEDRAUZYBX-UHFFFAOYSA-N n-[(3-fluoropyridin-4-yl)methyl]-4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]aniline Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NCC1=CC=NC=C1F MBZNHEDRAUZYBX-UHFFFAOYSA-N 0.000 claims 2
- GSQACQOYFRJZSB-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)thiophen-3-yl]phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C2=C(SC(=C2)C(F)(F)F)Cl)C=C1 GSQACQOYFRJZSB-UHFFFAOYSA-N 0.000 claims 2
- SGZPOKNXNNDVMX-UHFFFAOYSA-N n-[4-[3-chloro-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2ON=CC=2)Cl)C=C1 SGZPOKNXNNDVMX-UHFFFAOYSA-N 0.000 claims 2
- DAJNFRPCZUTFTL-UHFFFAOYSA-N n-[4-[3-chloro-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2ON=CC=2)Cl)C=C1 DAJNFRPCZUTFTL-UHFFFAOYSA-N 0.000 claims 2
- OFENLWLMCPARLH-UHFFFAOYSA-N n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]-1,2-thiazole-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C=1C=NSC=1 OFENLWLMCPARLH-UHFFFAOYSA-N 0.000 claims 2
- ONXZIMRIHBEHLA-UHFFFAOYSA-N n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]thiadiazole-4-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CSN=N1 ONXZIMRIHBEHLA-UHFFFAOYSA-N 0.000 claims 2
- GXFOPETWWQXAOO-UHFFFAOYSA-N n-[4-[3-methyl-5-(1,2-oxazol-5-yl)thiophen-2-yl]phenyl]thiadiazole-5-carboxamide Chemical compound CC=1C=C(C=2ON=CC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CN=NS1 GXFOPETWWQXAOO-UHFFFAOYSA-N 0.000 claims 2
- FFACYJASMJIMLV-UHFFFAOYSA-N n-[5-[3-chloro-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2OC=CN=2)Cl)C=N1 FFACYJASMJIMLV-UHFFFAOYSA-N 0.000 claims 2
- AMZUPFFHZNKAGX-UHFFFAOYSA-N n-[5-[3-chloro-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]-2-fluoro-6-methylbenzamide Chemical compound CC1=CC=CC(F)=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2OC=CN=2)Cl)C=N1 AMZUPFFHZNKAGX-UHFFFAOYSA-N 0.000 claims 2
- JMSDDJQQMQZTJC-UHFFFAOYSA-N n-[5-[3-chloro-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2OC=CN=2)Cl)C=N1 JMSDDJQQMQZTJC-UHFFFAOYSA-N 0.000 claims 2
- UXOWOJHWZFJHSH-UHFFFAOYSA-N n-[5-[3-chloro-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2OC=CN=2)Cl)C=N1 UXOWOJHWZFJHSH-UHFFFAOYSA-N 0.000 claims 2
- KQQJRYROFDDWDD-UHFFFAOYSA-N n-[5-[3-chloro-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C2=C(C=C(S2)C=2OC=CN=2)Cl)C=N1 KQQJRYROFDDWDD-UHFFFAOYSA-N 0.000 claims 2
- IOCFKRHNHBRWHM-UHFFFAOYSA-N n-[5-[3-chloro-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C2=C(C=C(S2)C=2OC=CN=2)Cl)=C1C IOCFKRHNHBRWHM-UHFFFAOYSA-N 0.000 claims 2
- UBNBNVBUHAWCLG-UHFFFAOYSA-N propyl 4-[4-[(2,6-difluorobenzoyl)amino]phenyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OCCC)=CC(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 UBNBNVBUHAWCLG-UHFFFAOYSA-N 0.000 claims 2
- PCNXMAYNSRXCKL-UHFFFAOYSA-N 1-methyl-n-[4-[3-methyl-5-(1,3-oxazol-5-yl)thiophen-2-yl]phenyl]pyrrole-2-carboxamide Chemical compound CC=1C=C(C=2OC=NC=2)SC=1C(C=C1)=CC=C1NC(=O)C1=CC=CN1C PCNXMAYNSRXCKL-UHFFFAOYSA-N 0.000 claims 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- ZNLXNMXTCAOHMI-UHFFFAOYSA-N 3-fluoro-n-[5-[3-methyl-5-(1,3-oxazol-2-yl)thiophen-2-yl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC=1C=C(C=2OC=CN=2)SC=1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1F ZNLXNMXTCAOHMI-UHFFFAOYSA-N 0.000 claims 1
- GGQQZWOIIGODQK-UHFFFAOYSA-N 4-methyl-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)furan-3-yl]phenyl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C2=C(OC(=C2)C=2SC=CN=2)C)=C1C GGQQZWOIIGODQK-UHFFFAOYSA-N 0.000 claims 1
- 102000004310 Ion Channels Human genes 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- 230000016396 cytokine production Effects 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- RFBCHWIHMOIXKH-UHFFFAOYSA-N methyl 5-methyl-4-[4-[(3-methylpyridine-4-carbonyl)amino]phenyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1C RFBCHWIHMOIXKH-UHFFFAOYSA-N 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 0 COC(c1cc(-c(cc2)ccc2S(N*)(=O)=O)c(C(F)(F)F)[s]1)=O Chemical compound COC(c1cc(-c(cc2)ccc2S(N*)(=O)=O)c(C(F)(F)F)[s]1)=O 0.000 description 2
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| PCT/US2007/002129 WO2007087429A2 (en) | 2006-01-25 | 2007-01-25 | Phenyl and pyridyl compounds for inflammation and immune-related uses |
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| TW (1) | TWI417096B (https=) |
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| CA2639910A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| WO2007087443A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
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| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
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| CA2779948A1 (en) | 2009-11-05 | 2011-05-12 | Piramal Life Sciences Limited | Carboxy oxazole or thiazole compounds as dgat-1 inhibitors useful for the treatment of obesity |
| DK2563776T3 (en) | 2010-04-27 | 2016-09-19 | Calcimedica Inc | Relations that modulate intracellular calcium |
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| WO2012112670A1 (en) * | 2011-02-16 | 2012-08-23 | Albert Einstein College Of Medicine Of Yeshiva University | Novel lipogenic inhibitors and uses thereof |
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| US9790231B2 (en) | 2013-06-24 | 2017-10-17 | Lupin Limited | Chromane and chromene derivatives and their use as CRAC modulators |
| WO2015187827A1 (en) * | 2014-06-03 | 2015-12-10 | The Trustees Of The University Of Pennsylvania | Novel effective antiviral compounds and methods using same |
| CN111978319B (zh) | 2014-06-27 | 2023-08-11 | 诺格拉制药有限公司 | 芳基受体调制剂及其制备和使用方法 |
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| WO2007087443A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| CA2639910A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| WO2007087441A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
-
2007
- 2007-01-25 US US11/698,982 patent/US20070275960A1/en not_active Abandoned
- 2007-01-25 WO PCT/US2007/002129 patent/WO2007087429A2/en not_active Ceased
- 2007-01-25 CA CA002639913A patent/CA2639913A1/en not_active Abandoned
- 2007-01-25 TW TW096102797A patent/TWI417096B/zh not_active IP Right Cessation
- 2007-01-25 EP EP07762437A patent/EP1983831A4/en not_active Withdrawn
- 2007-01-25 AU AU2007208227A patent/AU2007208227A1/en not_active Abandoned
- 2007-01-25 JP JP2008552424A patent/JP2009524678A/ja active Pending
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