JP2008528520A5 - - Google Patents
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- 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
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- 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
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- 2006-01-25 WO PCT/US2006/002874 patent/WO2006081391A2/en not_active Ceased
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- 2006-01-25 PL PL06719652T patent/PL1848435T3/pl unknown
- 2006-01-25 NZ NZ556732A patent/NZ556732A/en not_active IP Right Cessation
- 2006-01-25 US US11/340,184 patent/US8518950B2/en not_active Expired - Fee Related
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- 2006-01-25 KR KR1020077019485A patent/KR101436161B1/ko not_active Expired - Fee Related
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-
2007
- 2007-07-22 IL IL184756A patent/IL184756A0/en active IP Right Grant
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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
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2015
- 2015-06-05 US US14/731,862 patent/US9493427B2/en not_active Expired - Fee Related
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