JP2009524678A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76193106P | 2006-01-25 | 2006-01-25 | |
| US76201506P | 2006-01-25 | 2006-01-25 | |
| PCT/US2007/002129 WO2007087429A2 (en) | 2006-01-25 | 2007-01-25 | Phenyl and pyridyl compounds for inflammation and immune-related uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009524678A JP2009524678A (ja) | 2009-07-02 |
| JP2009524678A5 true JP2009524678A5 (https=) | 2010-03-18 |
Family
ID=38309865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008552424A Pending JP2009524678A (ja) | 2006-01-25 | 2007-01-25 | 炎症及び免疫関連用途のためのフェニル及びピリジル化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20070275960A1 (https=) |
| EP (1) | EP1983831A4 (https=) |
| JP (1) | JP2009524678A (https=) |
| AU (1) | AU2007208227A1 (https=) |
| CA (1) | CA2639913A1 (https=) |
| TW (1) | TWI417096B (https=) |
| WO (1) | WO2007087429A2 (https=) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050095228A1 (en) | 2001-12-07 | 2005-05-05 | Fraser John K. | Methods of using regenerative cells in the treatment of peripheral vascular disease and related disorders |
| US7771716B2 (en) | 2001-12-07 | 2010-08-10 | Cytori Therapeutics, Inc. | Methods of using regenerative cells in the treatment of musculoskeletal disorders |
| US7816535B2 (en) * | 2006-01-25 | 2010-10-19 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| TW200806290A (en) * | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted biaryl compounds for inflammation and immune-related uses |
| US8455658B2 (en) * | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| TW200806641A (en) * | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted aromatic compounds for inflammation and immune-related uses |
| AU2007227210A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceuticals Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
| MX2009002019A (es) | 2006-08-24 | 2009-03-09 | Novartis Ag | Derivados de 2-(pirazin-2-il)-tiazol y 2-(1h-pirazol-3-il)-tiazol asi como compuestos relacionados como inhibidores de la estearoil-coa-desaturasa (scd) para el tratamiento de trastornos metabolicos, cardiovasculares, y otros. |
| CA2662574A1 (en) | 2006-09-22 | 2008-03-27 | Novartis Ag | Heterocyclic organic compounds |
| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| WO2008074835A1 (en) | 2006-12-20 | 2008-06-26 | Novartis Ag | 2-substituted 5-membered heterocycles as scd inhibitors |
| CL2008001933A1 (es) * | 2007-06-29 | 2009-09-25 | Millennium Pharm Inc | Compuestos derivados de pirimidina, inhibidores de la raf quinasa; compuestos intermediarios; procedimiento de preparacion; composicion farmaceutica; y su uso para tratar trastornos proliferativos, cardiacos, neurodegenerativos, inflamatorios, oseos, inmunologicos enfermedad viral, entre otros. |
| CA2695143A1 (en) * | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Heterocycle-aryl compounds for inflammation and immune-related uses |
| US8263641B2 (en) | 2007-09-10 | 2012-09-11 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| US8124649B2 (en) | 2008-06-30 | 2012-02-28 | Cylene Pharmaceuticals, Inc. | Oxindole compounds |
| TWI392673B (zh) | 2008-08-27 | 2013-04-11 | Calcimedica Inc | 調控細胞內鈣離子濃度之化合物 |
| US8524763B2 (en) | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| AU2009300317A1 (en) * | 2008-10-01 | 2010-04-08 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US8143269B2 (en) | 2008-10-03 | 2012-03-27 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| EP2477982A4 (en) | 2009-09-16 | 2013-04-03 | Calcimedica Inc | COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM |
| US8993612B2 (en) | 2009-10-08 | 2015-03-31 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel and methods for treatment of non-small cell lung cancer |
| US8377970B2 (en) | 2009-10-08 | 2013-02-19 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel |
| NZ599855A (en) | 2009-11-05 | 2014-06-27 | Piramal Entpr Ltd | Carboxy oxazole or thiazole compounds as dgat - 1 inhibitors useful for the treatment of obesity |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| JP6112486B2 (ja) | 2010-04-27 | 2017-04-12 | カルシメディカ，インク． | 細胞内カルシウムを調節する化合物 |
| EP2609095A4 (en) | 2010-08-27 | 2014-06-18 | Calcimedica Inc | COMPOUNDS MODULATING INTRACELLULAR CALCIUM |
| AU2011322068B2 (en) | 2010-10-30 | 2015-11-05 | Lupin Limited | Oxazoline and isoxazoline derivatives as CRAC modulators |
| WO2012112670A1 (en) * | 2011-02-16 | 2012-08-23 | Albert Einstein College Of Medicine Of Yeshiva University | Novel lipogenic inhibitors and uses thereof |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CA2871270A1 (en) | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyridine compounds as crac modulators |
| WO2013164773A1 (en) | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyrazole compounds as crac modulators |
| SG11201407919WA (en) | 2012-05-31 | 2014-12-30 | Phenex Pharmaceuticals Ag | Carboxamide or sulfonamide substituted thiazoles and related derivatives as modulators for the orphan nuclear receptor ror[gamma] |
| WO2014043715A1 (en) * | 2012-09-17 | 2014-03-20 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2014203217A1 (en) | 2013-06-21 | 2014-12-24 | Lupin Limited | Substituted heterocyclic compounds as crac modulators |
| WO2014207648A1 (en) | 2013-06-24 | 2014-12-31 | 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 |
| MX388871B (es) | 2014-06-27 | 2025-03-20 | Nogra Pharma Ltd | Moduladores del receptor arilo y metodos para elaborar y usar los mismos. |
| EP3778595B1 (en) | 2015-02-27 | 2021-08-25 | Calcimedica, Inc. | Pancreatitis treatment |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| CN108774220B (zh) * | 2018-05-27 | 2019-04-23 | 西安培华学院 | 用于治疗心肌缺血的化合物及其应用 |
| WO2020053834A1 (en) | 2018-09-14 | 2020-03-19 | Rhizen Pharmaceuticals Sa | Compositions comprising a crac inhibitor and a corticosteroid and methods of use thereof |
| TWI885039B (zh) | 2020-01-13 | 2025-06-01 | 美商邊際分析公司 | 經取代吡唑并嘧啶及其用途 |
| JP2023528537A (ja) | 2020-03-20 | 2023-07-04 | カルシメディカ，インク． | 急性肺傷害及び急性呼吸窮迫症候群を処置するための方法及び組成物 |
| CA3198798A1 (en) | 2020-11-13 | 2022-05-19 | Kenneth Stauderman | Improved synthesis of crac channel inhibitors |
| CN118084860A (zh) * | 2024-02-06 | 2024-05-28 | 中国药科大学 | 芳酰胺类化合物及其药物组合物和应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2852503A (en) * | 1953-12-31 | 1958-09-16 | American Cyanamid Co | 2, 5-bis (p-aminophenyl) furan azo derivatives |
| CH484918A (de) * | 1965-10-28 | 1970-01-31 | Ciba Geigy | Verfahren zur Herstellung heterocyclischer, Aethylendoppelbindungen enthaltender Verbindungen |
| DE3021599A1 (de) * | 1980-06-09 | 1981-12-24 | Hoechst Ag, 6000 Frankfurt | 2-(halogenmethyl-phenyl)-4-halogenoxazol-derivate, ein verfahren zu ihrer herstellung und sie enthaltende strahlungsempfindliche massen |
| US6420403B1 (en) * | 1998-10-29 | 2002-07-16 | Edwin J. Iwanowicz | Inhibitors of IMPDH enzyme |
| CA2348267A1 (en) * | 1998-10-29 | 2000-05-11 | Henry H. Gu | Novel inhibitors of impdh enzyme |
| AU2002248432A1 (en) * | 2001-02-14 | 2002-08-28 | Sankyo Company, Limited | Oxazole derivatives, their preparation and their use as cytokine inhibitors |
| WO2003051876A1 (en) * | 2001-12-14 | 2003-06-26 | Japan Tobacco Inc. | Pyrazolopyridine derivatives and medicinal use thereof |
| GB0218147D0 (en) * | 2002-08-05 | 2002-09-11 | Oxford Glycosciences Uk Ltd | Novel compounds |
| KR100874292B1 (ko) * | 2002-11-18 | 2008-12-18 | 케모센트릭스 | 아릴 술폰아마이드 |
| US20060111351A1 (en) * | 2002-11-18 | 2006-05-25 | Solomon Ungashe | Aryl sulfonamides |
| US7420055B2 (en) * | 2002-11-18 | 2008-09-02 | Chemocentryx, Inc. | Aryl sulfonamides |
| TWI376370B (en) * | 2003-07-23 | 2012-11-11 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| US6984652B2 (en) * | 2003-09-05 | 2006-01-10 | Warner-Lambert Company Llc | Gyrase inhibitors |
| MXPA06003949A (es) * | 2003-10-07 | 2006-06-27 | Renovis Inc | Compuestos amida como ligandos del canal de ion y su uso. |
| US7514450B2 (en) * | 2004-05-19 | 2009-04-07 | Neurosearch A/S | Azabicyclic aryl derivatives |
| TW200806290A (en) * | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted biaryl compounds for inflammation and immune-related uses |
| US7816535B2 (en) * | 2006-01-25 | 2010-10-19 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| TW200806641A (en) * | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted aromatic compounds for inflammation and immune-related uses |
| US8455658B2 (en) * | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
-
2007
- 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 AU AU2007208227A patent/AU2007208227A1/en not_active Abandoned
- 2007-01-25 TW TW096102797A patent/TWI417096B/zh not_active IP Right Cessation
- 2007-01-25 US US11/698,982 patent/US20070275960A1/en not_active Abandoned
- 2007-01-25 EP EP07762437A patent/EP1983831A4/en not_active Withdrawn
- 2007-01-25 JP JP2008552424A patent/JP2009524678A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009524678A5 (https=) | ||
| JP2008526866A5 (https=) | ||
| JP2008528520A5 (https=) | ||
| ES2560627T3 (es) | Compuestos y procedimientos para la inhibición de HDAC | |
| JP2009525285A5 (https=) | ||
| US8354398B2 (en) | Substituted isoxazole compounds | |
| JP5184891B2 (ja) | 炎症及び免疫に関連する用途に用いる化合物 | |
| AU2007208225B2 (en) | Thiazole and thiadiazole compounds for inflammation and immune-related uses | |
| JP2009524683A5 (https=) | ||
| JP5225076B2 (ja) | チアゾール環を含むカルボン酸誘導体の医薬用途 | |
| JP2010504913A5 (https=) | ||
| ES2405054T3 (es) | Derivados de pirazol-1,2,4-oxadiazol como agonistas de esfingosina-1-fosfato | |
| CA2542609A1 (en) | Novel indazole derivatives | |
| CA2684105A1 (en) | Pyridine derivatives | |
| JP2007523905A5 (https=) | ||
| JP2006517572A5 (https=) | ||
| US20040248950A1 (en) | Apo ai expression accelerating agent | |
| JP2002524463A5 (https=) | ||
| JP2009529059A5 (https=) | ||
| SK49999A3 (en) | Oxadiazole derivatives, process for their preparation and their use as medicaments | |
| AU2005295778A1 (en) | Compounds for nonsense suppression, and methods for their use | |
| JP2009525984A5 (https=) | ||
| CA2639913A1 (en) | Phenyl and pyridyl compounds for inflammation and immune-related uses | |
| ES2525298T3 (es) | Compuestos heterocíclicos como agonistas del S1P1 para el tratamiento de enfermedades autoinmunes y vasculares | |
| JP2014513122A5 (https=) |