JP2008526866A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008526866A5 JP2008526866A5 JP2007550457A JP2007550457A JP2008526866A5 JP 2008526866 A5 JP2008526866 A5 JP 2008526866A5 JP 2007550457 A JP2007550457 A JP 2007550457A JP 2007550457 A JP2007550457 A JP 2007550457A JP 2008526866 A5 JP2008526866 A5 JP 2008526866A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- methyl
- biphenyl
- difluoro
- isonicotinamide
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 57
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 26
- 239000000651 prodrug Substances 0.000 claims 16
- 229940002612 prodrug Drugs 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000004414 alkyl thio group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- -1 1H-tetrazolyl Chemical group 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 6
- 125000002971 oxazolyl group Chemical group 0.000 claims 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 6
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- 125000000335 thiazolyl group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 3
- PUTFMOAOKZNUSN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(2h-tetrazol-5-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2NN=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F PUTFMOAOKZNUSN-UHFFFAOYSA-N 0.000 claims 3
- 102000004310 Ion Channels Human genes 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 230000005931 immune cell recruitment Effects 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- NHEMHKBZHHLNLI-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2ON=CC=2)C)C=C1 NHEMHKBZHHLNLI-UHFFFAOYSA-N 0.000 claims 2
- XKTZWZSXRKNGGM-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C XKTZWZSXRKNGGM-UHFFFAOYSA-N 0.000 claims 2
- WIMBOLXNLFZPHG-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=NC=2)C)C=C1 WIMBOLXNLFZPHG-UHFFFAOYSA-N 0.000 claims 2
- CMXASVOPXKZDOI-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)C)C=C1 CMXASVOPXKZDOI-UHFFFAOYSA-N 0.000 claims 2
- WQTHUZBGFPUICL-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(2h-tetrazol-5-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2NN=NN=2)C)C=C1 WQTHUZBGFPUICL-UHFFFAOYSA-N 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 210000003719 b-lymphocyte Anatomy 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 230000016396 cytokine production Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- ACZGJZKDSJLKPZ-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-methyl-5-pyridin-2-ylphenyl)phenyl]benzamide Chemical compound CC1=CC=C(C=2N=CC=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F ACZGJZKDSJLKPZ-UHFFFAOYSA-N 0.000 claims 1
- RJOOCBTVZKGDSW-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-methyl-5-pyridin-3-ylphenyl)phenyl]benzamide Chemical compound CC1=CC=C(C=2C=NC=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F RJOOCBTVZKGDSW-UHFFFAOYSA-N 0.000 claims 1
- DYJBJACFGHRXMH-UHFFFAOYSA-N 2,6-difluoro-n-[4-(2-methyl-5-pyridin-4-ylphenyl)phenyl]benzamide Chemical compound CC1=CC=C(C=2C=CN=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F DYJBJACFGHRXMH-UHFFFAOYSA-N 0.000 claims 1
- YCQQPBDGYUQILO-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methoxy-5-(1,3-oxazol-2-yl)phenyl]phenyl]benzamide Chemical compound COC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F YCQQPBDGYUQILO-UHFFFAOYSA-N 0.000 claims 1
- FRIGRPXYZRZZKE-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F FRIGRPXYZRZZKE-UHFFFAOYSA-N 0.000 claims 1
- PRCNEOSMANURNW-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F PRCNEOSMANURNW-UHFFFAOYSA-N 0.000 claims 1
- ZOHBMCUPFMAUSR-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F ZOHBMCUPFMAUSR-UHFFFAOYSA-N 0.000 claims 1
- VNYPBEICPYEHMU-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3-oxazol-4-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2N=COC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VNYPBEICPYEHMU-UHFFFAOYSA-N 0.000 claims 1
- JJJUQDROKHOMAQ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2OC=NC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F JJJUQDROKHOMAQ-UHFFFAOYSA-N 0.000 claims 1
- HDILCULZLSYGHY-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1-methyltetrazol-5-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2N(N=NN=2)C)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F HDILCULZLSYGHY-UHFFFAOYSA-N 0.000 claims 1
- VMGWUJGHNODFSG-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(1h-pyrrol-2-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2NC=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VMGWUJGHNODFSG-UHFFFAOYSA-N 0.000 claims 1
- FOBDRCIFVMXTIZ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(2-methyl-1,2,4-triazol-3-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2N(N=CN=2)C)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F FOBDRCIFVMXTIZ-UHFFFAOYSA-N 0.000 claims 1
- LIODNSHJTIDZIW-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(2-methyltetrazol-5-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C2=NN(C)N=N2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F LIODNSHJTIDZIW-UHFFFAOYSA-N 0.000 claims 1
- HEYNONRWYRATQB-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(3-methyl-1,2-oxazol-5-yl)phenyl]phenyl]benzamide Chemical compound O1N=C(C)C=C1C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 HEYNONRWYRATQB-UHFFFAOYSA-N 0.000 claims 1
- GYWJWMIPARWTPX-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(4-methyl-1,3-thiazol-2-yl)phenyl]phenyl]benzamide Chemical compound CC1=CSC(C=2C=C(C(C)=CC=2)C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=N1 GYWJWMIPARWTPX-UHFFFAOYSA-N 0.000 claims 1
- DZXZUWXTRUTBAZ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)phenyl]phenyl]benzamide Chemical compound CN1C(SC)=NN=C1C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 DZXZUWXTRUTBAZ-UHFFFAOYSA-N 0.000 claims 1
- XGHSASJTYJAMBM-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(5-methyl-1h-pyrazol-3-yl)phenyl]phenyl]benzamide Chemical compound N1N=C(C)C=C1C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 XGHSASJTYJAMBM-UHFFFAOYSA-N 0.000 claims 1
- RBKOFVZSWPUDHN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(5-oxo-2h-1,2,4-oxadiazol-3-yl)phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2NC(=O)ON=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F RBKOFVZSWPUDHN-UHFFFAOYSA-N 0.000 claims 1
- ADNXESORVNANSH-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenyl]phenyl]benzamide Chemical compound CC1=CC=C(C=2SC=C(N=2)C(F)(F)F)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F ADNXESORVNANSH-UHFFFAOYSA-N 0.000 claims 1
- HXUWFCJSAZOUHC-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methoxy-5-(1,3-oxazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound COC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F HXUWFCJSAZOUHC-UHFFFAOYSA-N 0.000 claims 1
- IBXFTAMPNIFRLP-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F IBXFTAMPNIFRLP-UHFFFAOYSA-N 0.000 claims 1
- GGFLWLCIACQRTN-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F GGFLWLCIACQRTN-UHFFFAOYSA-N 0.000 claims 1
- ABHZATVUDHEZLF-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F ABHZATVUDHEZLF-UHFFFAOYSA-N 0.000 claims 1
- YGSAGYAPEBUCNA-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=NC=C1F YGSAGYAPEBUCNA-UHFFFAOYSA-N 0.000 claims 1
- GUETUBNIKSOXBL-UHFFFAOYSA-N 3,5-difluoro-n-[4-[2-methyl-5-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CN1C(SC)=NN=C1C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3F)F)=CC=2)=C1 GUETUBNIKSOXBL-UHFFFAOYSA-N 0.000 claims 1
- NMPQFYMAMREFNS-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F NMPQFYMAMREFNS-UHFFFAOYSA-N 0.000 claims 1
- FEUMTZNEZOBMOK-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F FEUMTZNEZOBMOK-UHFFFAOYSA-N 0.000 claims 1
- WPCGQXNFVBKJKW-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F WPCGQXNFVBKJKW-UHFFFAOYSA-N 0.000 claims 1
- QCEDPLCXHVYYHI-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(1,3-oxazol-4-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2N=COC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F QCEDPLCXHVYYHI-UHFFFAOYSA-N 0.000 claims 1
- PJPOZVMUALBLIM-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F PJPOZVMUALBLIM-UHFFFAOYSA-N 0.000 claims 1
- MLZFLMBXBPPYEA-UHFFFAOYSA-N 3-fluoro-n-[4-[2-methyl-5-(2-methyl-1,2,4-triazol-3-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2N(N=CN=2)C)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1F MLZFLMBXBPPYEA-UHFFFAOYSA-N 0.000 claims 1
- CEIRNGJBZOTXOK-UHFFFAOYSA-N 3-methyl-n-[4-(2-methyl-5-pyridin-3-ylphenyl)phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2C=NC=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C CEIRNGJBZOTXOK-UHFFFAOYSA-N 0.000 claims 1
- GONHYCZCLJNREV-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C GONHYCZCLJNREV-UHFFFAOYSA-N 0.000 claims 1
- ZNMMURJWVGDXBJ-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 ZNMMURJWVGDXBJ-UHFFFAOYSA-N 0.000 claims 1
- RWWRLUIPEDCHLY-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-4-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2N=COC=2)C)C=C1 RWWRLUIPEDCHLY-UHFFFAOYSA-N 0.000 claims 1
- AOUOIIJWWFSLCP-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(1-methyltetrazol-5-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2N(N=NN=2)C)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C AOUOIIJWWFSLCP-UHFFFAOYSA-N 0.000 claims 1
- AXNLDNHUWVCRPF-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(3-methyl-1,2-oxazol-5-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound O1N=C(C)C=C1C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 AXNLDNHUWVCRPF-UHFFFAOYSA-N 0.000 claims 1
- FOHRUTIEUZNDIQ-UHFFFAOYSA-N 3-methyl-n-[4-[2-methyl-5-(4-methyl-1,3-thiazol-2-yl)phenyl]phenyl]pyridine-4-carboxamide Chemical compound CC1=CSC(C=2C=C(C(C)=CC=2)C=2C=CC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=N1 FOHRUTIEUZNDIQ-UHFFFAOYSA-N 0.000 claims 1
- WOUMRZCHSWVQTK-UHFFFAOYSA-N 4-methyl-n-[4-(2-methyl-5-pyridin-2-ylphenyl)phenyl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2N=CC=CC=2)C)=C1C WOUMRZCHSWVQTK-UHFFFAOYSA-N 0.000 claims 1
- CLGKUTCVDXQFFI-UHFFFAOYSA-N 4-methyl-n-[4-(2-methyl-5-pyridin-3-ylphenyl)phenyl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2C=NC=CC=2)C)=C1C CLGKUTCVDXQFFI-UHFFFAOYSA-N 0.000 claims 1
- CLQLZLCGPUHVLW-UHFFFAOYSA-N 4-methyl-n-[4-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]phenyl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2ON=CC=2)C)=C1C CLQLZLCGPUHVLW-UHFFFAOYSA-N 0.000 claims 1
- PTTPWZUIZKXKGY-UHFFFAOYSA-N 4-methyl-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]phenyl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2SC=CN=2)C)=C1C PTTPWZUIZKXKGY-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 150000001408 amides Chemical class 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 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
- 230000003834 intracellular effect Effects 0.000 claims 1
- JKAOBMCPBFAEQR-UHFFFAOYSA-N methyl 3-[4-[(2,6-difluorobenzoyl)amino]phenyl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 JKAOBMCPBFAEQR-UHFFFAOYSA-N 0.000 claims 1
- UUROVLXVZCQYKJ-UHFFFAOYSA-N methyl 3-[4-[(3,5-difluoropyridine-4-carbonyl)amino]phenyl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3F)F)=CC=2)=C1 UUROVLXVZCQYKJ-UHFFFAOYSA-N 0.000 claims 1
- NOBHVWOAQXWKFL-UHFFFAOYSA-N methyl 3-[4-[(3-fluoropyridine-4-carbonyl)amino]phenyl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)=C1 NOBHVWOAQXWKFL-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ZJYHCSIDRMVJCH-UHFFFAOYSA-N n-[4-(2-methoxy-5-thiophen-2-ylphenyl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(C=2SC=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C ZJYHCSIDRMVJCH-UHFFFAOYSA-N 0.000 claims 1
- REPOWMBMZCESPG-UHFFFAOYSA-N n-[4-(5-chloro-2-methoxypyridin-3-yl)phenyl]-2,6-difluorobenzamide Chemical compound COC1=NC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F REPOWMBMZCESPG-UHFFFAOYSA-N 0.000 claims 1
- FFQDNYZYQQTJCY-UHFFFAOYSA-N n-[4-(5-chloro-2-methoxypyridin-3-yl)phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C FFQDNYZYQQTJCY-UHFFFAOYSA-N 0.000 claims 1
- BVDBPRBGCAMVIK-UHFFFAOYSA-N n-[4-[2-(dimethylamino)-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound CN(C)C1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C BVDBPRBGCAMVIK-UHFFFAOYSA-N 0.000 claims 1
- BIIGGBDTMAWGEQ-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=C1 BIIGGBDTMAWGEQ-UHFFFAOYSA-N 0.000 claims 1
- VJEMLWSCIVANKS-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=C1 VJEMLWSCIVANKS-UHFFFAOYSA-N 0.000 claims 1
- DOIRCJTXASVGPW-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=C1 DOIRCJTXASVGPW-UHFFFAOYSA-N 0.000 claims 1
- FBPZZKCLQCACGD-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)C=C1 FBPZZKCLQCACGD-UHFFFAOYSA-N 0.000 claims 1
- RRPPHAPIBOIGBN-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)C=C1 RRPPHAPIBOIGBN-UHFFFAOYSA-N 0.000 claims 1
- CDXPRTPWAIUPGS-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)C=C1 CDXPRTPWAIUPGS-UHFFFAOYSA-N 0.000 claims 1
- JOMGPQQJXLLZEM-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)C=C1 JOMGPQQJXLLZEM-UHFFFAOYSA-N 0.000 claims 1
- KOKVANSMRRJMMS-UHFFFAOYSA-N n-[4-[2-methoxy-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C KOKVANSMRRJMMS-UHFFFAOYSA-N 0.000 claims 1
- SOOVPSRHNUYTBZ-UHFFFAOYSA-N n-[4-[2-methoxy-5-(1,3-oxazol-5-yl)phenyl]phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound COC1=CC=C(C=2OC=NC=2)C=C1C(C=C1)=CC=C1NC(=O)C=1SN=NC=1C SOOVPSRHNUYTBZ-UHFFFAOYSA-N 0.000 claims 1
- OSZIQZHRROTGTD-UHFFFAOYSA-N n-[4-[5-(5-amino-1,3,4-thiadiazol-2-yl)-2-methylphenyl]phenyl]-2,6-difluorobenzamide Chemical compound CC1=CC=C(C=2SC(N)=NN=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F OSZIQZHRROTGTD-UHFFFAOYSA-N 0.000 claims 1
- GEXVQFXUKFJYCI-UHFFFAOYSA-N n-[4-[5-(furan-2-yl)-2-methoxyphenyl]phenyl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(C=2OC=CC=2)C=C1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1C GEXVQFXUKFJYCI-UHFFFAOYSA-N 0.000 claims 1
- PKVFLLHAPLTWRZ-UHFFFAOYSA-N n-[4-[5-[5-(dimethylamino)-1,3,4-thiadiazol-2-yl]-2-methylphenyl]phenyl]-2,6-difluoro-n-methylbenzamide Chemical compound S1C(N(C)C)=NN=C1C1=CC=C(C)C(C=2C=CC(=CC=2)N(C)C(=O)C=2C(=CC=CC=2F)F)=C1 PKVFLLHAPLTWRZ-UHFFFAOYSA-N 0.000 claims 1
- BZUOMZUMVYMSMW-UHFFFAOYSA-N n-[4-[5-[5-(dimethylamino)-1,3,4-thiadiazol-2-yl]-2-methylphenyl]phenyl]-2,6-difluorobenzamide Chemical compound S1C(N(C)C)=NN=C1C1=CC=C(C)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 BZUOMZUMVYMSMW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 0 *C1C=CC(*)=CC1c(cc1)ccc1I* Chemical compound *C1C=CC(*)=CC1c(cc1)ccc1I* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64217905P | 2005-01-07 | 2005-01-07 | |
| US60/642,179 | 2005-01-07 | ||
| US70784505P | 2005-08-12 | 2005-08-12 | |
| US60/707,845 | 2005-08-12 | ||
| PCT/US2006/000296 WO2006083477A2 (en) | 2005-01-07 | 2006-01-06 | Compounds for inflammation and immune-related uses |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012100291A Division JP2012176959A (ja) | 2005-01-07 | 2012-04-25 | 炎症及び免疫に関連する用途に用いる化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008526866A JP2008526866A (ja) | 2008-07-24 |
| JP2008526866A5 true JP2008526866A5 (https=) | 2009-02-19 |
| JP5184891B2 JP5184891B2 (ja) | 2013-04-17 |
Family
ID=36777716
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007550457A Expired - Fee Related JP5184891B2 (ja) | 2005-01-07 | 2006-01-06 | 炎症及び免疫に関連する用途に用いる化合物 |
| JP2012100291A Pending JP2012176959A (ja) | 2005-01-07 | 2012-04-25 | 炎症及び免疫に関連する用途に用いる化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012100291A Pending JP2012176959A (ja) | 2005-01-07 | 2012-04-25 | 炎症及び免疫に関連する用途に用いる化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8202999B2 (https=) |
| EP (1) | EP1846372B1 (https=) |
| JP (2) | JP5184891B2 (https=) |
| KR (2) | KR20140018997A (https=) |
| AU (1) | AU2006211646B2 (https=) |
| BR (1) | BRPI0606476A2 (https=) |
| CA (1) | CA2593550A1 (https=) |
| IL (1) | IL184445A0 (https=) |
| MX (1) | MX2007008290A (https=) |
| NZ (1) | NZ556546A (https=) |
| TW (1) | TWI441819B (https=) |
| WO (1) | WO2006083477A2 (https=) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1846388A4 (en) * | 2005-01-25 | 2011-12-07 | Synta Pharmaceuticals Corp | THIOPHEN COMPOUNDS FOR IGNITIONS AND THE IMMUNE SYSTEM APPLICATIONS |
| PL1848435T3 (pl) | 2005-01-25 | 2016-08-31 | Synta Pharmaceuticals Corp | Związki przeciwko zapaleniom i zastosowania związane z odpornością |
| EP1940786B1 (en) * | 2005-09-16 | 2010-08-18 | Arrow Therapeutics Limited | Biphenyl derivatives and their use in treating hepatitis c |
| CA2628074C (en) | 2005-10-25 | 2014-01-14 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivative |
| 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 |
| TW200806641A (en) * | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted aromatic compounds for inflammation and immune-related uses |
| US20070254926A1 (en) * | 2006-01-31 | 2007-11-01 | Jun Jiang | Pyridylphenyl 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 |
| WO2008021849A2 (en) | 2006-08-09 | 2008-02-21 | Smithkline Beecham Corporation | Novel compounds as antagonists or inverse agonists at opioid receptors |
| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| US20080207641A1 (en) * | 2006-11-13 | 2008-08-28 | Synta Pharmaceuticals Corp. | Cyclohexenyl-aryl compounds for inflammation and immune-related uses |
| JP5383484B2 (ja) * | 2007-04-24 | 2014-01-08 | 塩野義製薬株式会社 | 環式基で置換されたアミノジヒドロチアジン誘導体 |
| US8653067B2 (en) * | 2007-04-24 | 2014-02-18 | Shionogi & Co., Ltd. | Pharmaceutical composition for treating Alzheimer's disease |
| CA2695148A1 (en) * | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Pyridine compounds for inflammation and immune-related uses |
| WO2009017831A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Vinyl-aryl derivatives for inflammation and immune-related uses |
| US8263641B2 (en) | 2007-09-10 | 2012-09-11 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2222638A2 (en) * | 2007-11-21 | 2010-09-01 | Decode Genetics EHF | Biaryl pde4 inhibitors for treating inflammation |
| JP2011504505A (ja) | 2007-11-21 | 2011-02-10 | デコード ジェネティクス イーエイチエフ | 肺および心血管障害を治療するためのビアリールｐｄｅ４抑制剤 |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8063152B2 (en) * | 2008-03-17 | 2011-11-22 | The Goodyear Tire & Rubber Company | Boron containing functionalizing agent |
| KR101324426B1 (ko) * | 2008-06-13 | 2013-10-31 | 시오노기세야쿠 가부시키가이샤 | β 세크레타제 저해 작용을 갖는 황 함유 복소환 유도체 |
| 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 |
| AU2009300318A1 (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 |
| CN102186841A (zh) * | 2008-10-22 | 2011-09-14 | 盐野义制药株式会社 | 具有bace1抑制活性的2-氨基嘧啶-4-酮及2-氨基吡啶衍生物 |
| EP2477982A4 (en) | 2009-09-16 | 2013-04-03 | Calcimedica Inc | COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM |
| US8377970B2 (en) * | 2009-10-08 | 2013-02-19 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel |
| 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 |
| MX2012006491A (es) | 2009-12-11 | 2012-07-03 | Shionogi & Co | Derivados de oxazina. |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | 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 |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2609095A4 (en) | 2010-08-27 | 2014-06-18 | Calcimedica Inc | COMPOUNDS MODULATING INTRACELLULAR CALCIUM |
| JP5816630B2 (ja) | 2010-10-29 | 2015-11-18 | 塩野義製薬株式会社 | ナフチリジン誘導体 |
| EP2634188A4 (en) | 2010-10-29 | 2014-05-07 | Shionogi & Co | FUSIONED AMINODIHYDROPYRIMIDINE DERIVATIVE |
| AU2011322068B2 (en) | 2010-10-30 | 2015-11-05 | Lupin Limited | Oxazoline and isoxazoline derivatives as CRAC modulators |
| US8883779B2 (en) | 2011-04-26 | 2014-11-11 | Shinogi & Co., Ltd. | Oxazine derivatives and a pharmaceutical composition for inhibiting BACE1 containing them |
| CA2834928C (en) | 2011-05-03 | 2017-10-17 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| KR101373705B1 (ko) * | 2011-08-05 | 2014-03-14 | 동국대학교 산학협력단 | 신규한 바이페닐 유도체 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 포함하는 염증성 질환 또는 자가면역질환의 예방 또는 치료용 약학적 조성물 |
| CA2848229C (en) | 2011-09-16 | 2019-08-27 | Fovea Pharmaceuticals | Aniline derivatives, their preparation and their therapeutic application |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2771069A4 (en) * | 2011-10-27 | 2015-08-26 | Mayo Foundation | INHIBITION OF G-PROTEIN-COUPLED RECEPTOR-6-KINASE POLYPEPTIDE |
| WO2013164773A1 (en) | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyrazole compounds as crac modulators |
| CA2871270A1 (en) | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyridine compounds as crac modulators |
| AR091654A1 (es) * | 2012-07-02 | 2015-02-18 | Biogen Idec Inc | COMPUESTOS QUE CONTIENEN BIARILO COMO AGONISTAS INVERSOS DE RECEPTORES ROR-g |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2912035A4 (en) | 2012-10-24 | 2016-06-15 | Shionogi & Co | DERIVATIVES OF DIHYDROOXAZINE OR OXAZEPINE HAVING BACE1 INHIBITING ACTIVITY |
| TR201302590A2 (tr) * | 2013-03-04 | 2014-09-22 | S Gueniz Kuecuekguezel | Diflunisalden hareketle yeni bileşiklerin sentezi. |
| 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 |
| AP2016009099A0 (en) * | 2013-11-01 | 2016-03-31 | Novartis Ag | Aminoheteroaryl benzamides as kinase inhibitors |
| WO2015090579A1 (en) * | 2013-12-18 | 2015-06-25 | Grünenthal GmbH | Pyrazolyl-based carboxamides iv |
| EP3134399A4 (en) | 2014-04-21 | 2017-12-27 | Mayo Foundation for Medical Education and Research | Small molecule inhibitors of g protein coupled receptor 6 kinases polypeptides |
| EP3778595B1 (en) | 2015-02-27 | 2021-08-25 | Calcimedica, Inc. | Pancreatitis treatment |
| KR101796390B1 (ko) | 2015-07-24 | 2017-11-09 | 동국대학교 산학협력단 | Blt 저해 활성을 갖는 신규 화합물 및 이를 유효성분으로 포함하는 염증성 질환 예방 또는 치료용 조성물 |
| WO2017018751A1 (ko) * | 2015-07-24 | 2017-02-02 | 동국대학교 산학협력단 | Blt 저해 활성을 갖는 신규 화합물 및 이를 유효성분으로 포함하는 염증성 질환 예방 또는 치료용 조성물 |
| KR20180035894A (ko) | 2015-08-03 | 2018-04-06 | 콰드리가 바이오사이언시스 인코포레이티드 | 화학치료제로서의 베타-치환된 베타-아미노산 및 유사체 및 이들의 용도 |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| AU2017264192B2 (en) * | 2016-05-10 | 2023-08-03 | National University Corporation Tokyo Medical And Dental University | Expression inhibitor of inflammation promoting factors, screening method for active ingredient thereof, expression cassette useful for said method, diagnostic agent and diagnosis method |
| KR102715821B1 (ko) | 2017-11-09 | 2024-10-10 | 고쿠리츠 다이가쿠호우징 도쿄이카시카다이가쿠 | 암 촉진 인자 발현 억제제, 그 유효 성분의 스크리닝 방법, 그 방법에 유용한 발현 카세트, 진단약, 및 진단 방법 |
| US10766900B2 (en) * | 2017-12-29 | 2020-09-08 | Formosa Laboratories, Inc. | Baricitinib intermediate, method for forming Baricitinib intermediate, and method for preparing Baricitinib or pharmaceutically acceptable salt thereof |
| 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 |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536809A (en) * | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) * | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3845770A (en) * | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) * | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) * | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| IE58110B1 (en) * | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US5073543A (en) * | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
| IT1229203B (it) * | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
| US5120548A (en) * | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
| US5733566A (en) * | 1990-05-15 | 1998-03-31 | Alkermes Controlled Therapeutics Inc. Ii | Controlled release of antiparasitic agents in animals |
| US5580578A (en) * | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| GB2273930A (en) | 1992-12-30 | 1994-07-06 | Glaxo Group Ltd | Benzanilide derivatives |
| US5591767A (en) * | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| GB2276161A (en) | 1993-03-17 | 1994-09-21 | Glaxo Group Ltd | Aniline and benzanilide derivatives |
| GB2276163A (en) | 1993-03-17 | 1994-09-21 | Glaxo Group Ltd | Pyridine compounds. |
| IT1270594B (it) * | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| WO1997023212A1 (en) | 1995-12-21 | 1997-07-03 | The Du Pont Merck Pharmaceutical Company | ISOXAZOLINE, ISOTHIAZOLINE AND PYRAZOLINE FACTOR Xa INHIBITORS |
| US6274171B1 (en) | 1996-03-25 | 2001-08-14 | American Home Products Corporation | Extended release formulation of venlafaxine hydrochloride |
| AU730224B2 (en) | 1996-12-23 | 2001-03-01 | Du Pont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| US6187797B1 (en) * | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
| US6020357A (en) * | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| DE69720773T2 (de) | 1996-12-23 | 2004-01-29 | Bristol Myers Squibb Pharma Co | SAUERSTOFF ODER SCHWEFEL ENTHALTENDE 5-GLIEDRIGE HETEROAROMATISHE DERIVATIVE ALS FACTOR Xa HEMMER |
| SK174699A3 (en) | 1997-06-19 | 2000-08-14 | Du Pont Pharm Co | Inhibitors of factor xa with a neutral p1 specificity group |
| US6060491A (en) * | 1997-06-19 | 2000-05-09 | Dupont Pharmaceuticals | 6-membered aromatics as factor Xa inhibitors |
| CA2293824A1 (en) | 1997-06-19 | 1998-12-23 | Mimi Lifen Quan | (amidino)6-membered aromatics as factor xa inhibitors |
| US6339099B1 (en) * | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| EP1042299A1 (en) | 1997-12-22 | 2000-10-11 | Du Pont Pharmaceuticals Company | Nitrogen containing heteroaromatics with ortho-substituted p1's as factor xa inhibitors |
| NZ511674A (en) | 1998-12-23 | 2003-11-28 | Du Pont Pharm Co | Nitrogen containing heterobicycles as factor Xa inhibitors |
| WO2000047553A2 (en) | 1999-02-11 | 2000-08-17 | Cor Therapeutics Inc. | ALKENYL AND ALKYNYL COMPOUNDS AS INHIBITORS OF FACTOR Xa |
| CN1346292A (zh) | 1999-03-11 | 2002-04-24 | 杜邦药品公司 | 凝血因子Xa抑制剂与阿司匹林、组织纤溶酶原激活物(TPA)、GPⅡb/Ⅲa拮抗剂、低分子量肝素或肝素联合用于治疗血栓形成 |
| ES2316383T3 (es) | 1999-09-17 | 2009-04-16 | Millennium Pharmaceuticals, Inc. | Benzamidas e inhibidores relacionados del factor xa. |
| CZ2002959A3 (cs) | 1999-09-17 | 2002-07-17 | Millennium Pharmaceuticals, Inc. | Inhibitory faktoru Xa |
| US6720317B1 (en) * | 1999-09-17 | 2004-04-13 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| US6844367B1 (en) * | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| US6632815B2 (en) * | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| US6329527B1 (en) | 1999-10-21 | 2001-12-11 | Bristol-Myers Squibb Pharma Company | Synthesis of 1,3,5-trisubstituted pyrazoles |
| EP1226123A1 (en) | 1999-11-03 | 2002-07-31 | Du Pont Pharmaceuticals Company | Cyano compounds as factor xa inhibitors |
| JP2003523356A (ja) | 2000-01-29 | 2003-08-05 | エルジー シーアイ リミテッド | アリール−アミジンを持つＸａ因子阻害剤とその誘導体、及びそれらのプロドラッグ |
| DE10008329A1 (de) | 2000-02-23 | 2001-08-30 | Merck Patent Gmbh | Aminosulfonylbiphenylderivate |
| WO2001064642A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| EP1285651B1 (en) | 2000-04-28 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonists |
| WO2002000647A1 (en) * | 2000-06-23 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Heteroaryl-phenyl substituted factor xa inhibitors |
| DE10035144A1 (de) | 2000-07-19 | 2002-01-31 | Merck Patent Gmbh | Cyclische Aminosäurederivate |
| US7283874B2 (en) | 2000-10-16 | 2007-10-16 | Remon Medical Technologies Ltd. | Acoustically powered implantable stimulating device |
| GB0106586D0 (en) | 2001-03-16 | 2001-05-09 | Smithkline Beecham Plc | Novel compounds |
| US7074801B1 (en) | 2001-04-26 | 2006-07-11 | Eisai Co., Ltd. | Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof |
| WO2003005025A1 (en) | 2001-07-03 | 2003-01-16 | Biovitrum Ab | Methods for identifying compounds modulating the activity of ppar-gamma |
| GB0124932D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124928D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| AU2003254177A1 (en) | 2002-07-31 | 2004-02-16 | Smithkline Beecham Corporation | Substituted benzanilides as modulators of the ccr5 receptor |
| US20040029920A1 (en) | 2002-08-06 | 2004-02-12 | Kuduk Scott D. | 2-(biarylalkyl)amino-3-(heterocyclylcarbonylamino)-pyridine derivatives |
| WO2004056774A2 (en) | 2002-12-19 | 2004-07-08 | Neurogen Corporation | Substituted biphenyl-4-carboxylic acid arylamide analogues as capsaicin receptor modulators |
| TWI376370B (en) * | 2003-07-23 | 2012-11-11 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| GB0325031D0 (en) | 2003-10-27 | 2003-12-03 | Novartis Ag | Organic compounds |
| CA2558585C (en) | 2004-02-27 | 2010-10-12 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders |
| TW200619191A (en) | 2004-10-27 | 2006-06-16 | Sankyo Co | Phenyl compounds with more than 2 substitutes |
-
2006
- 2006-01-06 KR KR1020137034625A patent/KR20140018997A/ko not_active Ceased
- 2006-01-06 MX MX2007008290A patent/MX2007008290A/es active IP Right Grant
- 2006-01-06 AU AU2006211646A patent/AU2006211646B2/en not_active Ceased
- 2006-01-06 JP JP2007550457A patent/JP5184891B2/ja not_active Expired - Fee Related
- 2006-01-06 WO PCT/US2006/000296 patent/WO2006083477A2/en not_active Ceased
- 2006-01-06 KR KR1020077017923A patent/KR20070107022A/ko not_active Ceased
- 2006-01-06 NZ NZ556546A patent/NZ556546A/en not_active IP Right Cessation
- 2006-01-06 EP EP06733619.8A patent/EP1846372B1/en not_active Expired - Lifetime
- 2006-01-06 US US11/326,872 patent/US8202999B2/en not_active Expired - Fee Related
- 2006-01-06 TW TW095100558A patent/TWI441819B/zh not_active IP Right Cessation
- 2006-01-06 CA CA002593550A patent/CA2593550A1/en not_active Abandoned
- 2006-01-06 BR BRPI0606476-0A patent/BRPI0606476A2/pt not_active IP Right Cessation
-
2007
- 2007-07-05 IL IL184445A patent/IL184445A0/en unknown
-
2012
- 2012-04-25 JP JP2012100291A patent/JP2012176959A/ja active Pending
- 2012-05-14 US US13/470,772 patent/US8592486B2/en not_active Expired - Fee Related
-
2013
- 2013-10-15 US US14/053,896 patent/US20140039009A1/en not_active Abandoned