JP2008528520A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008528520A5 JP2008528520A5 JP2007552414A JP2007552414A JP2008528520A5 JP 2008528520 A5 JP2008528520 A5 JP 2008528520A5 JP 2007552414 A JP2007552414 A JP 2007552414A JP 2007552414 A JP2007552414 A JP 2007552414A JP 2008528520 A5 JP2008528520 A5 JP 2008528520A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazin
- methyl
- phenyl
- isonicotinamide
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 44
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 238000000034 method Methods 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 210000004027 cell Anatomy 0.000 claims 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims 7
- -1 —NH 2 Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 4
- 102000004310 Ion Channels Human genes 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 230000005931 immune cell recruitment Effects 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 230000016396 cytokine production Effects 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 210000003630 histaminocyte Anatomy 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- YYXUUCUNSYYSOK-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]benzamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F YYXUUCUNSYYSOK-UHFFFAOYSA-N 0.000 claims 1
- KCAWYBSBRWESMM-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1-methyltetrazol-5-yl)phenyl]pyrazin-2-yl]benzamide Chemical compound CC1=CC=C(C=2N(N=NN=2)C)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F KCAWYBSBRWESMM-UHFFFAOYSA-N 0.000 claims 1
- BBVMNHCZWAWJEQ-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(2h-tetrazol-5-yl)phenyl]pyrazin-2-yl]benzamide Chemical compound CC1=CC=C(C=2NN=NN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F BBVMNHCZWAWJEQ-UHFFFAOYSA-N 0.000 claims 1
- HJPVCDSNKJCAEV-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrazin-2-yl]benzamide Chemical compound CC1=NOC(C=2C=C(C(C)=CC=2)C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=N1 HJPVCDSNKJCAEV-UHFFFAOYSA-N 0.000 claims 1
- BEIWPGFESKJDLT-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(furan-2-yl)-2-methoxypyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound COC1=NC=C(C=2OC=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F BEIWPGFESKJDLT-UHFFFAOYSA-N 0.000 claims 1
- CQXVINRPUOWTLF-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(furan-3-yl)-2-methoxypyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound COC1=NC=C(C2=COC=C2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F CQXVINRPUOWTLF-UHFFFAOYSA-N 0.000 claims 1
- CHKZTBGJJNQBGX-UHFFFAOYSA-N 2-methoxyethyl 3-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound COCCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 CHKZTBGJJNQBGX-UHFFFAOYSA-N 0.000 claims 1
- XMHKTCADFIIDIV-UHFFFAOYSA-N 2-methoxyethyl 3-[5-[(3,5-difluoropyridine-4-carbonyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound COCCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 XMHKTCADFIIDIV-UHFFFAOYSA-N 0.000 claims 1
- RHNXQACJZXCRKN-UHFFFAOYSA-N 2-methoxyethyl 3-chloro-4-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]benzoate Chemical compound ClC1=CC(C(=O)OCCOC)=CC=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F RHNXQACJZXCRKN-UHFFFAOYSA-N 0.000 claims 1
- YYOHZXXANNDMQI-UHFFFAOYSA-N 2-methoxyethyl 4-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OCCOC)=CC=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F YYOHZXXANNDMQI-UHFFFAOYSA-N 0.000 claims 1
- ZGIYKIFJRFYGBY-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 ZGIYKIFJRFYGBY-UHFFFAOYSA-N 0.000 claims 1
- QJJXRYGQAWGWIE-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[5-[(3,5-difluoropyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 QJJXRYGQAWGWIE-UHFFFAOYSA-N 0.000 claims 1
- DONMKKIRNMOYGP-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[5-[(3-methylpyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 DONMKKIRNMOYGP-UHFFFAOYSA-N 0.000 claims 1
- PEQJVRGQBKLFRJ-UHFFFAOYSA-N 2-methoxyethyl 4-methyl-3-[5-[(3-methylpyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 PEQJVRGQBKLFRJ-UHFFFAOYSA-N 0.000 claims 1
- BJNUJJLIKVIDBG-UHFFFAOYSA-N 3,5-difluoro-n-[5-(5-isocyano-2-methylphenyl)pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C([N+]#[C-])C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F BJNUJJLIKVIDBG-UHFFFAOYSA-N 0.000 claims 1
- IHBMLADIDFXDLH-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F IHBMLADIDFXDLH-UHFFFAOYSA-N 0.000 claims 1
- IALBWLASERSJLF-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,2-thiazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SN=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F IALBWLASERSJLF-UHFFFAOYSA-N 0.000 claims 1
- ITWBUUTWLBWJOP-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F ITWBUUTWLBWJOP-UHFFFAOYSA-N 0.000 claims 1
- VHHGAXWJHCUVJQ-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F VHHGAXWJHCUVJQ-UHFFFAOYSA-N 0.000 claims 1
- UKUYLVHLZIZSCJ-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F UKUYLVHLZIZSCJ-UHFFFAOYSA-N 0.000 claims 1
- LUGOMEQOCGHHDW-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F LUGOMEQOCGHHDW-UHFFFAOYSA-N 0.000 claims 1
- NVCDQOBUHBAKRX-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F NVCDQOBUHBAKRX-UHFFFAOYSA-N 0.000 claims 1
- ZSXSBWDCOYVCGQ-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3-thiazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F ZSXSBWDCOYVCGQ-UHFFFAOYSA-N 0.000 claims 1
- CDARSDXYVPDRAM-UHFFFAOYSA-N 3,5-difluoro-n-[5-[5-(furan-3-yl)-2-methoxypyridin-3-yl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound COC1=NC=C(C2=COC=C2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F CDARSDXYVPDRAM-UHFFFAOYSA-N 0.000 claims 1
- XRCAPFMEPYLVBJ-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F XRCAPFMEPYLVBJ-UHFFFAOYSA-N 0.000 claims 1
- AIDNWEOXWIPESQ-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,2-thiazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SN=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F AIDNWEOXWIPESQ-UHFFFAOYSA-N 0.000 claims 1
- OSFYIWJMPZABDR-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F OSFYIWJMPZABDR-UHFFFAOYSA-N 0.000 claims 1
- VTBPHMRYILWULV-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F VTBPHMRYILWULV-UHFFFAOYSA-N 0.000 claims 1
- YFNIBJIEOJFYQV-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F YFNIBJIEOJFYQV-UHFFFAOYSA-N 0.000 claims 1
- WUWAHDZJURZTMM-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F WUWAHDZJURZTMM-UHFFFAOYSA-N 0.000 claims 1
- ZGCHYXBABCBFSB-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3-thiazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F ZGCHYXBABCBFSB-UHFFFAOYSA-N 0.000 claims 1
- XEQJGCAHVWCSHU-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(trifluoromethyl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C(F)(F)F)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F XEQJGCAHVWCSHU-UHFFFAOYSA-N 0.000 claims 1
- NHXKMXIANJAUSG-UHFFFAOYSA-N 3-fluoro-n-[5-[5-(furan-2-yl)-2-methoxypyridin-3-yl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound COC1=NC=C(C=2OC=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F NHXKMXIANJAUSG-UHFFFAOYSA-N 0.000 claims 1
- NEVAEBJRMIDVGH-UHFFFAOYSA-N 3-fluoro-n-[5-[5-(furan-3-yl)-2-methoxypyridin-3-yl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound COC1=NC=C(C2=COC=C2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F NEVAEBJRMIDVGH-UHFFFAOYSA-N 0.000 claims 1
- HHFXRDRGAYKEBN-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C HHFXRDRGAYKEBN-UHFFFAOYSA-N 0.000 claims 1
- BTLWWBBVNXMTOL-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,2-thiazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SN=CC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C BTLWWBBVNXMTOL-UHFFFAOYSA-N 0.000 claims 1
- HOOWLONMQYJDFK-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C HOOWLONMQYJDFK-UHFFFAOYSA-N 0.000 claims 1
- OHEZEXJHXFSSFX-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C OHEZEXJHXFSSFX-UHFFFAOYSA-N 0.000 claims 1
- DDCBZERPLDXCOU-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C DDCBZERPLDXCOU-UHFFFAOYSA-N 0.000 claims 1
- KQHJWAGVUFXANB-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C KQHJWAGVUFXANB-UHFFFAOYSA-N 0.000 claims 1
- INFQOYPPLPAYTN-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C INFQOYPPLPAYTN-UHFFFAOYSA-N 0.000 claims 1
- JDSQOHCXVZLDNV-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-thiazol-5-yl)phenyl]pyrazin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NC=2)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C JDSQOHCXVZLDNV-UHFFFAOYSA-N 0.000 claims 1
- LBBPJNSNUZHORQ-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2ON=CC=2)C)=C1C LBBPJNSNUZHORQ-UHFFFAOYSA-N 0.000 claims 1
- SBMGPILILLNRDG-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,2-thiazol-5-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2SN=CC=2)C)=C1C SBMGPILILLNRDG-UHFFFAOYSA-N 0.000 claims 1
- FIFBSXMJHYVVIC-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2OC=NN=2)C)=C1C FIFBSXMJHYVVIC-UHFFFAOYSA-N 0.000 claims 1
- FXHAKTGZEDGTMH-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2SC=NN=2)C)=C1C FXHAKTGZEDGTMH-UHFFFAOYSA-N 0.000 claims 1
- BEOIOZJKEGJJAN-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C1C BEOIOZJKEGJJAN-UHFFFAOYSA-N 0.000 claims 1
- INHNRAQPUMAMCI-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2OC=NC=2)C)=C1C INHNRAQPUMAMCI-UHFFFAOYSA-N 0.000 claims 1
- PIMDINSOPQTKBI-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2SC=CN=2)C)=C1C PIMDINSOPQTKBI-UHFFFAOYSA-N 0.000 claims 1
- OFGGCPRFABHKAX-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3-thiazol-5-yl)phenyl]pyrazin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2SC=NC=2)C)=C1C OFGGCPRFABHKAX-UHFFFAOYSA-N 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
- 230000004663 cell proliferation Effects 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- RGIWWXRNXJSDPU-UHFFFAOYSA-N ethyl 3-[5-[(3,5-difluoropyridine-4-carbonyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 RGIWWXRNXJSDPU-UHFFFAOYSA-N 0.000 claims 1
- YTLHGOHQTISUJA-UHFFFAOYSA-N ethyl 3-chloro-4-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]benzoate Chemical compound ClC1=CC(C(=O)OCC)=CC=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F YTLHGOHQTISUJA-UHFFFAOYSA-N 0.000 claims 1
- QDRRYKJFIPXLCA-UHFFFAOYSA-N ethyl 4-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OCC)=CC=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F QDRRYKJFIPXLCA-UHFFFAOYSA-N 0.000 claims 1
- BOBCRRHYNXVUTD-UHFFFAOYSA-N ethyl 4-chloro-3-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 BOBCRRHYNXVUTD-UHFFFAOYSA-N 0.000 claims 1
- ZPBHGCRHCBZCCA-UHFFFAOYSA-N ethyl 4-chloro-3-[5-[(3,5-difluoropyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 ZPBHGCRHCBZCCA-UHFFFAOYSA-N 0.000 claims 1
- DOXJHWTZSKWGDO-UHFFFAOYSA-N ethyl 4-chloro-3-[5-[(3-methylpyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 DOXJHWTZSKWGDO-UHFFFAOYSA-N 0.000 claims 1
- RKPVVYXRBCGBPA-UHFFFAOYSA-N ethyl 4-methyl-3-[5-[(3-methylpyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 RKPVVYXRBCGBPA-UHFFFAOYSA-N 0.000 claims 1
- 210000002865 immune cell Anatomy 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- ICVBQGSFGNUIFB-UHFFFAOYSA-N methyl 3-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 ICVBQGSFGNUIFB-UHFFFAOYSA-N 0.000 claims 1
- PBNIKOVTSHCMEA-UHFFFAOYSA-N methyl 3-[5-[(3,5-difluoropyridine-4-carbonyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 PBNIKOVTSHCMEA-UHFFFAOYSA-N 0.000 claims 1
- KJLXJYDBCNLZCS-UHFFFAOYSA-N methyl 3-[5-[(3-fluoropyridine-4-carbonyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)F)=NC=2)=C1 KJLXJYDBCNLZCS-UHFFFAOYSA-N 0.000 claims 1
- PWHNDEKZPDWABW-UHFFFAOYSA-N methyl 3-chloro-4-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]benzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F PWHNDEKZPDWABW-UHFFFAOYSA-N 0.000 claims 1
- SIERIJXTFJRETQ-UHFFFAOYSA-N methyl 4-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F SIERIJXTFJRETQ-UHFFFAOYSA-N 0.000 claims 1
- GBENQNIEWSKRHI-UHFFFAOYSA-N methyl 4-chloro-3-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 GBENQNIEWSKRHI-UHFFFAOYSA-N 0.000 claims 1
- PYJIBZPTTNLGHX-UHFFFAOYSA-N methyl 4-chloro-3-[5-[(3,5-difluoropyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 PYJIBZPTTNLGHX-UHFFFAOYSA-N 0.000 claims 1
- PYOSBBDTDBFRED-UHFFFAOYSA-N methyl 4-chloro-3-[5-[(3-methylpyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 PYOSBBDTDBFRED-UHFFFAOYSA-N 0.000 claims 1
- GXJLCVCHLMKXGP-UHFFFAOYSA-N methyl 4-methyl-3-[5-[(3-methylpyridine-4-carbonyl)amino]pyrazin-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 GXJLCVCHLMKXGP-UHFFFAOYSA-N 0.000 claims 1
- IRGKZXZDXBPAQE-UHFFFAOYSA-N n-[2-[2-chloro-5-(trifluoromethyl)phenyl]pyrimidin-5-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)N=C1 IRGKZXZDXBPAQE-UHFFFAOYSA-N 0.000 claims 1
- GVIGMZXZQAQUBR-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound COC1=CC=C(OC)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 GVIGMZXZQAQUBR-UHFFFAOYSA-N 0.000 claims 1
- XIAFHSZQLGDOJU-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound COC1=CC=C(OC)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3F)F)=NC=2)=C1 XIAFHSZQLGDOJU-UHFFFAOYSA-N 0.000 claims 1
- UXAFENFGRLRBGT-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound COC1=CC=C(OC)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)F)=NC=2)=C1 UXAFENFGRLRBGT-UHFFFAOYSA-N 0.000 claims 1
- NGGHKQILRPJRDW-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound COC1=CC=C(OC)C(C=2N=CC(NC(=O)C=3C(=CN=CC=3)C)=NC=2)=C1 NGGHKQILRPJRDW-UHFFFAOYSA-N 0.000 claims 1
- GHDBNUNFHGFZLW-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)pyrazin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound COC1=CC=C(OC)C(C=2N=CC(NC(=O)C3=C(N=NS3)C)=NC=2)=C1 GHDBNUNFHGFZLW-UHFFFAOYSA-N 0.000 claims 1
- NJNCMALVIPPPER-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)pyrazin-2-yl]cyclohexanecarboxamide Chemical compound COC1=CC=C(OC)C(C=2N=CC(NC(=O)C3CCCCC3)=NC=2)=C1 NJNCMALVIPPPER-UHFFFAOYSA-N 0.000 claims 1
- RUGQZWUSCYZRJA-UHFFFAOYSA-N n-[5-(5-bromo-2-methoxypyridin-3-yl)pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound COC1=NC=C(Br)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F RUGQZWUSCYZRJA-UHFFFAOYSA-N 0.000 claims 1
- BBRVDACCEBOPKC-UHFFFAOYSA-N n-[5-(5-bromo-2-methoxypyridin-3-yl)pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound COC1=NC=C(Br)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F BBRVDACCEBOPKC-UHFFFAOYSA-N 0.000 claims 1
- RNIDJDQEFXWWDD-UHFFFAOYSA-N n-[5-(5-bromo-2-methoxypyridin-3-yl)pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound COC1=NC=C(Br)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F RNIDJDQEFXWWDD-UHFFFAOYSA-N 0.000 claims 1
- WJOQNFYBDSCGCP-UHFFFAOYSA-N n-[5-(5-bromo-2-methoxypyridin-3-yl)pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound COC1=NC=C(Br)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C WJOQNFYBDSCGCP-UHFFFAOYSA-N 0.000 claims 1
- JVHDAGXXHGXPAG-UHFFFAOYSA-N n-[5-(5-carbamoyl-2-methylphenyl)pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound CC1=CC=C(C(N)=O)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F JVHDAGXXHGXPAG-UHFFFAOYSA-N 0.000 claims 1
- IHLABQMULAEWCA-UHFFFAOYSA-N n-[5-(5-carbamoyl-2-methylphenyl)pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F IHLABQMULAEWCA-UHFFFAOYSA-N 0.000 claims 1
- XFKGBNBUCFSRGN-UHFFFAOYSA-N n-[5-(5-carbamoyl-2-methylphenyl)pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F XFKGBNBUCFSRGN-UHFFFAOYSA-N 0.000 claims 1
- XRMHAIFPCFZOEP-UHFFFAOYSA-N n-[5-(5-carbamoyl-2-methylphenyl)pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C XRMHAIFPCFZOEP-UHFFFAOYSA-N 0.000 claims 1
- YLUZVSLUTGIGEA-UHFFFAOYSA-N n-[5-(5-chloro-2-methoxypyridin-3-yl)pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound COC1=NC=C(Cl)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F YLUZVSLUTGIGEA-UHFFFAOYSA-N 0.000 claims 1
- JBZBXVUQCQASMI-UHFFFAOYSA-N n-[5-(5-chloro-2-methoxypyridin-3-yl)pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F JBZBXVUQCQASMI-UHFFFAOYSA-N 0.000 claims 1
- WYYFLJPFDJDBPN-UHFFFAOYSA-N n-[5-(5-chloro-2-methoxypyridin-3-yl)pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F WYYFLJPFDJDBPN-UHFFFAOYSA-N 0.000 claims 1
- NVALBNAOBBMXCX-UHFFFAOYSA-N n-[5-(5-chloro-2-methoxypyridin-3-yl)pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C NVALBNAOBBMXCX-UHFFFAOYSA-N 0.000 claims 1
- KXDCKTJYSBOUAY-UHFFFAOYSA-N n-[5-(5-cyano-2-methylphenyl)pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound CC1=CC=C(C#N)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1F KXDCKTJYSBOUAY-UHFFFAOYSA-N 0.000 claims 1
- ABRIWKLJWXTFSC-UHFFFAOYSA-N n-[5-(5-cyano-2-methylphenyl)pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CC=C(C#N)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C ABRIWKLJWXTFSC-UHFFFAOYSA-N 0.000 claims 1
- TUKJNCWLTGNUNP-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2ON=CC=2)Cl)C=N1 TUKJNCWLTGNUNP-UHFFFAOYSA-N 0.000 claims 1
- ITLWLOZNXBPJIL-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2ON=CC=2)Cl)C=N1 ITLWLOZNXBPJIL-UHFFFAOYSA-N 0.000 claims 1
- FKXADVXDMQSUHR-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2ON=CC=2)Cl)C=N1 FKXADVXDMQSUHR-UHFFFAOYSA-N 0.000 claims 1
- UWCCHRQVKIDEJF-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,2-oxazol-5-yl)phenyl]pyrazin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2ON=CC=2)Cl)=C1C UWCCHRQVKIDEJF-UHFFFAOYSA-N 0.000 claims 1
- CULNCXUQQPBSBN-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=NN=2)Cl)C=N1 CULNCXUQQPBSBN-UHFFFAOYSA-N 0.000 claims 1
- JKSCIODTHZZWFR-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=NN=2)Cl)C=N1 JKSCIODTHZZWFR-UHFFFAOYSA-N 0.000 claims 1
- XGSGSQNTWZOKAF-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=NN=2)Cl)C=N1 XGSGSQNTWZOKAF-UHFFFAOYSA-N 0.000 claims 1
- PQWUFBUVHLCDNZ-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3,4-oxadiazol-2-yl)phenyl]pyrazin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2OC=NN=2)Cl)=C1C PQWUFBUVHLCDNZ-UHFFFAOYSA-N 0.000 claims 1
- FIVBUSCGIFWYCQ-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=N1 FIVBUSCGIFWYCQ-UHFFFAOYSA-N 0.000 claims 1
- MLNAJVMZNYVCGF-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=N1 MLNAJVMZNYVCGF-UHFFFAOYSA-N 0.000 claims 1
- VWWDEHZFEKPAOG-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=N1 VWWDEHZFEKPAOG-UHFFFAOYSA-N 0.000 claims 1
- FOQVIWYXUWOMGL-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)=C1C FOQVIWYXUWOMGL-UHFFFAOYSA-N 0.000 claims 1
- BXOKTMWVAACAQR-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=NC=2)Cl)C=N1 BXOKTMWVAACAQR-UHFFFAOYSA-N 0.000 claims 1
- ALYITEDONVOBBB-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=NC=2)Cl)C=N1 ALYITEDONVOBBB-UHFFFAOYSA-N 0.000 claims 1
- JDJZLHGGZWXSHQ-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=NC=2)Cl)C=N1 JDJZLHGGZWXSHQ-UHFFFAOYSA-N 0.000 claims 1
- OGSRUYNYHLMIJA-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-5-yl)phenyl]pyrazin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C=2OC=NC=2)Cl)=C1C OGSRUYNYHLMIJA-UHFFFAOYSA-N 0.000 claims 1
- WEGNVAKDOVUFCR-UHFFFAOYSA-N n-[5-[2-chloro-5-(furan-2-yl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C=2OC=CC=2)Cl)C=N1 WEGNVAKDOVUFCR-UHFFFAOYSA-N 0.000 claims 1
- VWGRWSIIKLXSHD-UHFFFAOYSA-N n-[5-[2-chloro-5-(furan-3-yl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C2=COC=C2)Cl)C=N1 VWGRWSIIKLXSHD-UHFFFAOYSA-N 0.000 claims 1
- LWJKSVUJZBEXCH-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 LWJKSVUJZBEXCH-UHFFFAOYSA-N 0.000 claims 1
- PGWKNMGHSOTPEW-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-2,6-difluorobenzamide;hydrochloride Chemical compound Cl.FC1=CC=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 PGWKNMGHSOTPEW-UHFFFAOYSA-N 0.000 claims 1
- BIVRMTFFHALQHW-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-2-methylpyridine-3-carboxamide Chemical compound CC1=NC=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 BIVRMTFFHALQHW-UHFFFAOYSA-N 0.000 claims 1
- JIJDXRHJPPFBJD-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound FC1=CN=CC(F)=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 JIJDXRHJPPFBJD-UHFFFAOYSA-N 0.000 claims 1
- PSHUELISKRPXOH-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 PSHUELISKRPXOH-UHFFFAOYSA-N 0.000 claims 1
- GSBMEFMHQICUJZ-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 GSBMEFMHQICUJZ-UHFFFAOYSA-N 0.000 claims 1
- QMYNCBJMWOATIX-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=NC=2)C=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1C QMYNCBJMWOATIX-UHFFFAOYSA-N 0.000 claims 1
- DMBATDAMTYWLBI-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrazin-2-yl]cyclohexanecarboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2N=CC(NC(=O)C3CCCCC3)=NC=2)=C1 DMBATDAMTYWLBI-UHFFFAOYSA-N 0.000 claims 1
- XGKQDCMTIUYHED-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyrimidin-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=NC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 XGKQDCMTIUYHED-UHFFFAOYSA-N 0.000 claims 1
- YWONVDTWOGEDAY-UHFFFAOYSA-N n-[5-[2-ethyl-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-2,6-difluorobenzamide Chemical compound CCC1=CC=C(C(F)(F)F)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F YWONVDTWOGEDAY-UHFFFAOYSA-N 0.000 claims 1
- MUESZNKDTSRMAB-UHFFFAOYSA-N n-[5-[2-ethyl-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-3,5-difluoropyridine-4-carboxamide Chemical compound CCC1=CC=C(C(F)(F)F)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=NC=C1F MUESZNKDTSRMAB-UHFFFAOYSA-N 0.000 claims 1
- HAPUZKXLJCYPNP-UHFFFAOYSA-N n-[5-[2-ethyl-5-(trifluoromethyl)phenyl]pyrazin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CCC1=CC=C(C(F)(F)F)C=C1C(N=C1)=CN=C1NC(=O)C1=CC=NC=C1C HAPUZKXLJCYPNP-UHFFFAOYSA-N 0.000 claims 1
- IRBHWLHFKLKVEN-UHFFFAOYSA-N n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyrazin-2-yl]cyclohexanecarboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CN=C1NC(=O)C1CCCCC1 IRBHWLHFKLKVEN-UHFFFAOYSA-N 0.000 claims 1
- KUMDOBBOTLNOGL-UHFFFAOYSA-N n-[6-[2-chloro-5-(trifluoromethyl)phenyl]pyridazin-3-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)N=N1 KUMDOBBOTLNOGL-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- ZEMKJAPQSNQUAP-UHFFFAOYSA-N propyl 3-[5-[(2,6-difluorobenzoyl)amino]pyrazin-2-yl]-4-methylbenzoate Chemical compound CCCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 ZEMKJAPQSNQUAP-UHFFFAOYSA-N 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64668305P | 2005-01-25 | 2005-01-25 | |
| US60/646,683 | 2005-01-25 | ||
| PCT/US2006/002874 WO2006081391A2 (en) | 2005-01-25 | 2006-01-25 | Compounds for inflammation and immune-related uses |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012230254A Division JP2013047247A (ja) | 2005-01-25 | 2012-10-17 | 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 |
|---|---|
| JP2008528520A JP2008528520A (ja) | 2008-07-31 |
| JP2008528520A5 true JP2008528520A5 (enExample) | 2009-03-26 |
| JP5307402B2 JP5307402B2 (ja) | 2013-10-02 |
Family
ID=36741062
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007552414A Expired - Fee Related JP5307402B2 (ja) | 2005-01-25 | 2006-01-25 | 炎症及び免疫に関連する用途に用いる化合物 |
| JP2012230254A Pending JP2013047247A (ja) | 2005-01-25 | 2012-10-17 | 炎症及び免疫に関連する用途に用いる化合物 |
| JP2014177307A Pending JP2014221840A (ja) | 2005-01-25 | 2014-09-01 | 炎症及び免疫に関連する用途に用いる化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012230254A Pending JP2013047247A (ja) | 2005-01-25 | 2012-10-17 | 炎症及び免疫に関連する用途に用いる化合物 |
| JP2014177307A Pending JP2014221840A (ja) | 2005-01-25 | 2014-09-01 | 炎症及び免疫に関連する用途に用いる化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US8518950B2 (enExample) |
| EP (1) | EP1848435B1 (enExample) |
| JP (3) | JP5307402B2 (enExample) |
| KR (1) | KR101436161B1 (enExample) |
| CN (1) | CN101163478B (enExample) |
| AU (1) | AU2006208045B2 (enExample) |
| BR (1) | BRPI0607308A2 (enExample) |
| CA (1) | CA2595855C (enExample) |
| ES (1) | ES2567853T3 (enExample) |
| IL (1) | IL184756A0 (enExample) |
| MX (1) | MX2007008957A (enExample) |
| NZ (2) | NZ556732A (enExample) |
| PL (1) | PL1848435T3 (enExample) |
| TW (1) | TWI422376B (enExample) |
| WO (1) | WO2006081391A2 (enExample) |
| ZA (1) | ZA200707125B (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006208045B2 (en) | 2005-01-25 | 2012-08-30 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| WO2006081389A1 (en) * | 2005-01-25 | 2006-08-03 | Synta Pharmaceuticals Corp. | Thiophene 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 |
| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
| CA2640090A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| CA2645434A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceutical Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| EP2086326B1 (en) * | 2006-11-13 | 2014-01-08 | Synta Pharmaceuticals Corp. | Cyclohexenyl-aryl compounds for inflammation and immune-related uses |
| ES2440267T3 (es) * | 2007-08-01 | 2014-01-28 | Synta Pharmaceuticals Corporation | Compuestos de heterociclo-arilo para la inflamación y usos inmunorrelacionados |
| EP2185514A4 (en) * | 2007-08-01 | 2011-05-18 | Synta Pharmaceuticals Corp | VINYL-ARYL DERIVATIVES FOR INFLAMMATORY AND IMMUNE DISORDERS |
| CA2696349A1 (en) | 2007-08-15 | 2009-02-19 | President And Fellows Of Harvard College | Heterocyclic inhibitors of necroptosis |
| RU2465272C2 (ru) | 2007-09-10 | 2012-10-27 | КалсиМедика, Инк. | Соединения, моделирующие внутриклеточный кальций |
| WO2009076454A2 (en) | 2007-12-12 | 2009-06-18 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CA2734500A1 (en) | 2008-08-27 | 2010-03-11 | Calcimedica Inc. | Compounds that modulate intracellular calcium |
| US8524763B2 (en) | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| 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 |
| MX2012002591A (es) | 2009-09-03 | 2012-04-02 | Allergan Inc | Compuestos como moduladores de tirosina cinasas. |
| US9340555B2 (en) | 2009-09-03 | 2016-05-17 | Allergan, Inc. | Compounds as tyrosine kinase modulators |
| US8618307B2 (en) | 2009-09-16 | 2013-12-31 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN102803502B (zh) * | 2009-09-29 | 2019-06-04 | 宾夕法尼亚大学理事会 | 用于诊断和治疗脑炎或癫痫的方法 |
| 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 |
| 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 |
| CN103180316A (zh) | 2010-08-27 | 2013-06-26 | 钙医学公司 | 调节细胞内钙的化合物 |
| AP3341A (en) | 2010-10-30 | 2015-07-31 | Lupin Ltd | Oxazoline and isoxazoline derivatives as crac modulators |
| AR086113A1 (es) * | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| EP2704701B1 (en) * | 2011-05-03 | 2018-01-03 | PRCL Research Inc. | Compounds for inflammation and immune-related uses |
| WO2012170931A2 (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 |
| US9527859B2 (en) | 2012-04-13 | 2016-12-27 | Mitsubishi Tanabe Pharma Corporation | Amidopyridine derivative and use thereof |
| AU2013255441B2 (en) | 2012-05-02 | 2017-11-09 | Lupin Limited | Substituted pyrazole compounds as CRAC modulators |
| EP2844655A1 (en) | 2012-05-02 | 2015-03-11 | Lupin Limited | Substituted pyridine compounds as crac modulators |
| US20150344407A1 (en) * | 2012-08-21 | 2015-12-03 | The Board Of Regents Of The University Of Texas System | Fendiline derivatives and methods of use thereof |
| WO2014059333A1 (en) | 2012-10-12 | 2014-04-17 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2014145022A1 (en) | 2013-03-15 | 2014-09-18 | President And Fellows Of Harvard College | Hybrid necroptosis inhibitors |
| US9725463B2 (en) | 2013-06-21 | 2017-08-08 | Lupin Limited | Substituted heterocyclic compounds as CRAC modulators |
| EP3013810A1 (en) | 2013-06-24 | 2016-05-04 | Lupin Limited | Chromane and chromene derivatives and their use as crac modulators |
| WO2016057338A1 (en) | 2014-10-06 | 2016-04-14 | Takeda Pharmaceutical Company Limited | Heteroarylamide inhibitors of tbk1 |
| TWI771269B (zh) | 2015-02-27 | 2022-07-21 | 美商鈣系醫藥公司 | 胰腺炎治療 |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| JP2022508468A (ja) | 2018-09-14 | 2022-01-19 | ルヒゼン ファーマスティカルズ アクツィエンゲゼルシャフト | Ｃｒａｃ阻害剤およびコルチコステロイドを含む組成物ならびにそれらの使用方法 |
| WO2021009332A1 (en) * | 2019-07-18 | 2021-01-21 | Enyo Pharma | Method for decreasing adverse-effects of interferon |
| CN114206850B (zh) | 2019-09-25 | 2024-01-26 | 辰欣药业股份有限公司 | 作为crac抑制剂的2h-苯并吡喃衍生物 |
| AR120896A1 (es) * | 2019-12-25 | 2022-03-30 | Astellas Pharma Inc | COMPUESTO DE PIRIDAZINIL-TIAZOLCARBOXAMIDA COMO INHIBIDORES DE DGKz |
| US12486274B2 (en) | 2020-01-13 | 2025-12-02 | Verge Analytics, Inc. | Substituted pyrazolo-pyrimidines and uses thereof |
| CA3172249A1 (en) | 2020-03-20 | 2021-09-23 | Calcimedica, Inc. | Methods and compositions for treating acute lung injury and acute respiratory distress syndrome |
| JP7791898B2 (ja) | 2020-11-13 | 2025-12-24 | カルシメディカ，インク． | Ｃｒａｃチャネル阻害剤の合成の改善 |
| WO2022114164A1 (ja) * | 2020-11-30 | 2022-06-02 | アステラス製薬株式会社 | ヘテロアリールカルボキシアミド化合物 |
| WO2022179577A1 (zh) * | 2021-02-25 | 2022-09-01 | 南京明德新药研发有限公司 | 一种环丙基取代的苯并呋喃类化合物的晶型及其制备方法 |
Family Cites Families (51)
| 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 |
| US5591767A (en) | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| US6274171B1 (en) | 1996-03-25 | 2001-08-14 | American Home Products Corporation | Extended release formulation of venlafaxine hydrochloride |
| MA26473A1 (fr) * | 1997-03-01 | 2004-12-20 | Glaxo Group Ltd | Composes pharmacologiquement actifs. |
| JP4385414B2 (ja) | 1997-10-13 | 2009-12-16 | アステラス製薬株式会社 | アミド若しくはアミン誘導体 |
| TWI279402B (en) * | 1999-08-20 | 2007-04-21 | Banyu Pharma Co Ltd | Spiro compounds having NPY antagonistic activities and agents containing the same |
| US6462053B1 (en) * | 1999-08-20 | 2002-10-08 | Banyu Pharmaceutical Co., Ltd. | Spiro compounds |
| US6803372B2 (en) | 1999-08-20 | 2004-10-12 | Banyu Pharmaceutical Co., Ltd. | Spiro compounds |
| JP3553560B2 (ja) * | 1999-08-20 | 2004-08-11 | 萬有製薬株式会社 | 新規スピロ化合物 |
| WO2001037826A1 (en) * | 1999-11-26 | 2001-05-31 | Shionogi & Co., Ltd. | Npyy5 antagonists |
| JP4083422B2 (ja) | 2000-12-22 | 2008-04-30 | 石原産業株式会社 | アニリン誘導体またはその塩ならびにそれらを含有するサイトカイン産生抑制剤 |
| US6924291B2 (en) | 2001-01-23 | 2005-08-02 | Merck & Co., Inc. | Process for making spiro isobenzofuranone compounds |
| 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 |
| AU2002358390A1 (en) | 2001-12-18 | 2003-06-30 | Astrazeneca Ab | Novel compounds |
| US7189851B2 (en) * | 2002-03-06 | 2007-03-13 | Smithkline Beecham Corporation | Condensed heterocyclic compounds as calcitonin agonists |
| AU2003253925A1 (en) | 2002-07-18 | 2004-02-09 | Banyu Pharmaceutical Co., Ltd. | Combination therapy for the treatment of obesity |
| EP1553089B1 (en) * | 2002-07-30 | 2009-09-30 | Banyu Pharmaceutical Co., Ltd. | Antagonist of melanin-concentrating hormone receptor comprising benzimidazole derivative as active ingredient |
| US20040110802A1 (en) * | 2002-08-23 | 2004-06-10 | Atli Thorarensen | Antibacterial benzoic acid derivatives |
| US6657024B1 (en) | 2002-09-03 | 2003-12-02 | Fina Technology, Inc. | Polymerization catalyst system using n-butylmethyldimethoxysilane for preparation of polypropylene film grade resins |
| US20060100245A1 (en) * | 2002-12-19 | 2006-05-11 | Neurogen Corporation | Substituted biphenyl-4-carboxylic acid arylamide analogues |
| WO2004089919A1 (ja) | 2003-04-02 | 2004-10-21 | Banyu Pharmaceutical Co., Ltd. | シクロヘキサンカルボキサミド誘導体 |
| US20070099884A1 (en) * | 2003-06-06 | 2007-05-03 | Erondu Ngozi E | Combination therapy for the treatment of diabetes |
| US20060148721A1 (en) | 2003-06-06 | 2006-07-06 | Erondu Ngozi E | Combination therapy for the treatment of dyslipidemia |
| EP1644365A2 (en) | 2003-07-02 | 2006-04-12 | Biofocus Discovery Ltd | Pyrazine and pyridine derivatives as rho kinase inhibitors |
| NZ545447A (en) | 2003-07-23 | 2010-03-26 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| CN1838958A (zh) | 2003-08-22 | 2006-09-27 | 贝林格尔·英格海姆药物公司 | 治疗慢性阻塞性肺病和肺动脉高血压的方法 |
| WO2005090340A1 (ja) * | 2004-03-22 | 2005-09-29 | Banyu Pharmaceutical Co., Ltd. | ピペリジン－１－カルボキサミド誘導体 |
| KR20070057965A (ko) | 2004-09-21 | 2007-06-07 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| JP4988591B2 (ja) | 2004-12-17 | 2012-08-01 | イーライ リリー アンド カンパニー | 新規なｍｃｈ受容体アンタゴニスト |
| WO2006083477A2 (en) | 2005-01-07 | 2006-08-10 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| WO2006081389A1 (en) | 2005-01-25 | 2006-08-03 | Synta Pharmaceuticals Corp. | Thiophene compounds for inflammation and immune-related uses |
| AU2006208045B2 (en) | 2005-01-25 | 2012-08-30 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| ES2270715B1 (es) | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| PT2404919E (pt) * | 2005-11-08 | 2013-10-22 | Vertex Pharma | Composto heterocíclico útil como um modulador de transportadores de cassete de ligação a atp |
| JP2009518442A (ja) | 2005-12-05 | 2009-05-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 可溶性エポキシド加水分解酵素インヒビターとして有益な置換ピラゾール化合物 |
| WO2007089335A2 (en) | 2005-12-29 | 2007-08-09 | Lexicon Pharmaceutical Inc. | Multicyclic amino acid derivatives and methods of their use |
| WO2007084456A2 (en) | 2006-01-13 | 2007-07-26 | Vanderbilt University | System and methods of deep brain stimulation for post-operation patients |
| PE20071241A1 (es) * | 2006-01-17 | 2008-01-14 | Schering Corp | Compuestos derivados de hidantoina para el tratamiento de trastornos inflamatorios |
| CA2645434A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceutical Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
-
2006
- 2006-01-25 AU AU2006208045A patent/AU2006208045B2/en not_active Ceased
- 2006-01-25 ZA ZA200707125A patent/ZA200707125B/xx unknown
- 2006-01-25 BR BRPI0607308-5A patent/BRPI0607308A2/pt not_active IP Right Cessation
- 2006-01-25 TW TW095102767A patent/TWI422376B/zh not_active IP Right Cessation
- 2006-01-25 NZ NZ556732A patent/NZ556732A/en not_active IP Right Cessation
- 2006-01-25 NZ NZ590359A patent/NZ590359A/xx not_active IP Right Cessation
- 2006-01-25 WO PCT/US2006/002874 patent/WO2006081391A2/en not_active Ceased
- 2006-01-25 CA CA2595855A patent/CA2595855C/en not_active Expired - Fee Related
- 2006-01-25 KR KR1020077019485A patent/KR101436161B1/ko not_active Expired - Fee Related
- 2006-01-25 EP EP06719652.7A patent/EP1848435B1/en not_active Expired - Lifetime
- 2006-01-25 MX MX2007008957A patent/MX2007008957A/es active IP Right Grant
- 2006-01-25 ES ES06719652.7T patent/ES2567853T3/es not_active Expired - Lifetime
- 2006-01-25 CN CN2006800031821A patent/CN101163478B/zh not_active Expired - Fee Related
- 2006-01-25 PL PL06719652T patent/PL1848435T3/pl unknown
- 2006-01-25 US US11/340,184 patent/US8518950B2/en not_active Expired - Fee Related
- 2006-01-25 JP JP2007552414A patent/JP5307402B2/ja not_active Expired - Fee Related
-
2007
- 2007-07-22 IL IL184756A patent/IL184756A0/en active IP Right Grant
-
2012
- 2012-10-17 JP JP2012230254A patent/JP2013047247A/ja active Pending
-
2013
- 2013-07-23 US US13/948,541 patent/US9090570B2/en not_active Expired - Fee Related
-
2014
- 2014-09-01 JP JP2014177307A patent/JP2014221840A/ja active Pending
-
2015
- 2015-06-05 US US14/731,862 patent/US9493427B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009524678A5 (enExample) | ||
| US8354398B2 (en) | Substituted isoxazole compounds | |
| ES2547877T3 (es) | Compuestos diaril-oxadiazol | |
| JP2008526866A5 (enExample) | ||
| JP2008528519A5 (enExample) | ||
| RU2012132692A (ru) | Новые ингибиторы s-нитрозоглутатионредуктазы | |
| EP2595969B1 (en) | Substituted 3-phenyl-1,2,4-oxadiazole compounds | |
| JP2009519965A5 (enExample) | ||
| US8178548B2 (en) | Anti-infective agents and uses thereof | |
| JP2002524463A5 (enExample) | ||
| ES2525298T3 (es) | Compuestos heterocíclicos como agonistas del S1P1 para el tratamiento de enfermedades autoinmunes y vasculares | |
| ZA200403137B (en) | Dibenzylamine compound and medicinal use thereof | |
| JP2002536445A5 (enExample) | ||
| JP2004520292A5 (enExample) | ||
| JP2009525285A5 (enExample) | ||
| CN117045653A (zh) | 与毒性醛相关的疾病和治疗 | |
| CA2648036A1 (en) | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor | |
| CN103102348B (zh) | 噁二唑类化合物及其制备方法、药物组合物及其用途 | |
| CA2683738A1 (en) | Indanone derivatives that inhibit prolyl hydroxylase | |
| JP2005525371A5 (enExample) | ||
| CA2513092A1 (en) | Compounds for the treatment of metabolic disorders | |
| ES2548258T3 (es) | Compuestos de oxadiazol sustituidos y su uso como agonistas de S1P1 | |
| JPWO2006137509A1 (ja) | Ｐｐａｒ調節剤を含有する医薬組成物 | |
| JP2009540009A5 (enExample) | ||
| CA2521621A1 (en) | Compounds for the treatment of metabolic disorders |