JP2008528519A5 - - Google Patents
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- JP2008528519A5 JP2008528519A5 JP2007552413A JP2007552413A JP2008528519A5 JP 2008528519 A5 JP2008528519 A5 JP 2008528519A5 JP 2007552413 A JP2007552413 A JP 2007552413A JP 2007552413 A JP2007552413 A JP 2007552413A JP 2008528519 A5 JP2008528519 A5 JP 2008528519A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- methyl
- thiophen
- phenyl
- pyridin
- 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 34
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000005843 halogen group Chemical group 0.000 claims 21
- -1 3,5-difluoro-pyridin-4-ylcarbamoyl Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 9
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 9
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 7
- 230000002401 inhibitory effect Effects 0.000 claims 7
- 210000004027 cell Anatomy 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 238000000338 in vitro Methods 0.000 claims 5
- 102000004310 Ion Channels Human genes 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 230000005931 immune cell recruitment Effects 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- SCRHWKOZSWUPKR-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1C SCRHWKOZSWUPKR-UHFFFAOYSA-N 0.000 claims 2
- SZUVFRSOGIBPNO-UHFFFAOYSA-N 5-(5-carbamoyl-2-methylphenyl)-n-(2,6-difluorophenyl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 SZUVFRSOGIBPNO-UHFFFAOYSA-N 0.000 claims 2
- 108090000695 Cytokines Proteins 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 210000003719 b-lymphocyte Anatomy 0.000 claims 2
- 210000003630 histaminocyte Anatomy 0.000 claims 2
- ACGGWEQWSHHHPS-UHFFFAOYSA-N methyl 3-chloro-4-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]benzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 ACGGWEQWSHHHPS-UHFFFAOYSA-N 0.000 claims 2
- BAEBBDIFQSEKMY-UHFFFAOYSA-N methyl 4-methyl-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 BAEBBDIFQSEKMY-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- DFFBRMLHLXNTBV-UHFFFAOYSA-N propyl 4-chloro-3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 DFFBRMLHLXNTBV-UHFFFAOYSA-N 0.000 claims 2
- RMTLHQQETULZDK-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]thiophen-2-yl]benzamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(S1)=CC=C1NC(=O)C1=C(F)C=CC=C1F RMTLHQQETULZDK-UHFFFAOYSA-N 0.000 claims 1
- UELRFSJDXDLMOI-UHFFFAOYSA-N 2,6-difluoro-n-[5-[3-(trifluoromethyl)phenyl]thiophen-2-yl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C=C(C=CC=2)C(F)(F)F)S1 UELRFSJDXDLMOI-UHFFFAOYSA-N 0.000 claims 1
- MDHWZJUMDNYPNM-UHFFFAOYSA-N 2-methoxyethyl 3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]-4-methylbenzoate Chemical compound COCCOC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 MDHWZJUMDNYPNM-UHFFFAOYSA-N 0.000 claims 1
- HPOVNSVWDXOZEN-UHFFFAOYSA-N 2-methoxyethyl 3-[5-[(3,5-difluoropyridin-4-yl)carbamoyl]thiophen-2-yl]-4-methylbenzoate Chemical compound COCCOC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2F)F)=C1 HPOVNSVWDXOZEN-UHFFFAOYSA-N 0.000 claims 1
- XJKYXJZNGKCQAZ-UHFFFAOYSA-N 2-methoxyethyl 3-chloro-4-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]benzoate Chemical compound ClC1=CC(C(=O)OCCOC)=CC=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 XJKYXJZNGKCQAZ-UHFFFAOYSA-N 0.000 claims 1
- OIAGDNSHPPQUJO-UHFFFAOYSA-N 2-methoxyethyl 4-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OCCOC)=CC=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 OIAGDNSHPPQUJO-UHFFFAOYSA-N 0.000 claims 1
- ZAHFPKWOQJHYTI-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 ZAHFPKWOQJHYTI-UHFFFAOYSA-N 0.000 claims 1
- TZGJAIZYYKTUAY-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[5-[(3,5-difluoropyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2F)F)=C1 TZGJAIZYYKTUAY-UHFFFAOYSA-N 0.000 claims 1
- OLTLNUWCRQNFDV-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 OLTLNUWCRQNFDV-UHFFFAOYSA-N 0.000 claims 1
- XCRYJKQSYMEMPM-UHFFFAOYSA-N 2-methoxyethyl 4-methyl-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 XCRYJKQSYMEMPM-UHFFFAOYSA-N 0.000 claims 1
- YKVCQIOABFYYHR-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(S1)=CC=C1NC(=O)C1=C(F)C=NC=C1F YKVCQIOABFYYHR-UHFFFAOYSA-N 0.000 claims 1
- HYJANQFYIOQISJ-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(S1)=CC=C1NC(=O)C1=C(F)C=NC=C1F HYJANQFYIOQISJ-UHFFFAOYSA-N 0.000 claims 1
- FWPVEECGGXZVAM-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(S1)=CC=C1NC(=O)C1=C(F)C=NC=C1F FWPVEECGGXZVAM-UHFFFAOYSA-N 0.000 claims 1
- JNNKPLGLXGSHAC-UHFFFAOYSA-N 3,5-difluoro-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(S1)=CC=C1NC(=O)C1=C(F)C=NC=C1F JNNKPLGLXGSHAC-UHFFFAOYSA-N 0.000 claims 1
- NTSOTTUZKUTNQU-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1F NTSOTTUZKUTNQU-UHFFFAOYSA-N 0.000 claims 1
- PTEJNWGOBSKDCI-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1F PTEJNWGOBSKDCI-UHFFFAOYSA-N 0.000 claims 1
- NQVOKZGDLMVMOE-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1F NQVOKZGDLMVMOE-UHFFFAOYSA-N 0.000 claims 1
- SCHJWFVIHDUIDE-UHFFFAOYSA-N 3-fluoro-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1F SCHJWFVIHDUIDE-UHFFFAOYSA-N 0.000 claims 1
- HMTVKTCKCSRNSG-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1C HMTVKTCKCSRNSG-UHFFFAOYSA-N 0.000 claims 1
- JSLGZZWANSGFFA-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]thiophen-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(S1)=CC=C1NC(=O)C1=CC=NC=C1C JSLGZZWANSGFFA-UHFFFAOYSA-N 0.000 claims 1
- RLCIPEANWMGUII-UHFFFAOYSA-N 5-(5-bromo-2-methoxypyridin-3-yl)-n-(2,6-difluorophenyl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Br)C=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 RLCIPEANWMGUII-UHFFFAOYSA-N 0.000 claims 1
- CNPMNPDDRZQEHW-UHFFFAOYSA-N 5-(5-bromo-2-methoxypyridin-3-yl)-n-(3,5-difluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Br)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2F)F)S1 CNPMNPDDRZQEHW-UHFFFAOYSA-N 0.000 claims 1
- GRKXGTHICDNIBR-UHFFFAOYSA-N 5-(5-bromo-2-methoxypyridin-3-yl)-n-(3-fluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Br)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)F)S1 GRKXGTHICDNIBR-UHFFFAOYSA-N 0.000 claims 1
- ICGNIEKBYLVFFF-UHFFFAOYSA-N 5-(5-bromo-2-methoxypyridin-3-yl)-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Br)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)C)S1 ICGNIEKBYLVFFF-UHFFFAOYSA-N 0.000 claims 1
- HDQZPHBCASKWMW-UHFFFAOYSA-N 5-(5-carbamoyl-2-methylphenyl)-n-(3,5-difluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2F)F)S1 HDQZPHBCASKWMW-UHFFFAOYSA-N 0.000 claims 1
- YLNLHLZSKRNCJH-UHFFFAOYSA-N 5-(5-carbamoyl-2-methylphenyl)-n-(3-fluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)F)S1 YLNLHLZSKRNCJH-UHFFFAOYSA-N 0.000 claims 1
- GNYSHBLOQSPQCW-UHFFFAOYSA-N 5-(5-carbamoyl-2-methylphenyl)-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C(N)=O)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)C)S1 GNYSHBLOQSPQCW-UHFFFAOYSA-N 0.000 claims 1
- XXRNWZQWAGYWQG-UHFFFAOYSA-N 5-(5-chloro-2-methoxypyridin-3-yl)-n-(2,6-difluorophenyl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 XXRNWZQWAGYWQG-UHFFFAOYSA-N 0.000 claims 1
- JRUGWMFEMJFCEK-UHFFFAOYSA-N 5-(5-chloro-2-methoxypyridin-3-yl)-n-(3,5-difluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2F)F)S1 JRUGWMFEMJFCEK-UHFFFAOYSA-N 0.000 claims 1
- ZDLMXOGDJFFDLU-UHFFFAOYSA-N 5-(5-chloro-2-methoxypyridin-3-yl)-n-(3-fluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)F)S1 ZDLMXOGDJFFDLU-UHFFFAOYSA-N 0.000 claims 1
- SBKWIGZHNKHPNS-UHFFFAOYSA-N 5-(5-chloro-2-methoxypyridin-3-yl)-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(Cl)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)C)S1 SBKWIGZHNKHPNS-UHFFFAOYSA-N 0.000 claims 1
- PCKSUQPUEASMEU-UHFFFAOYSA-N 5-(5-cyano-2-methylphenyl)-n-(3,5-difluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C#N)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2F)F)S1 PCKSUQPUEASMEU-UHFFFAOYSA-N 0.000 claims 1
- AYBBZFKTQHXGRA-UHFFFAOYSA-N 5-(5-cyano-2-methylphenyl)-n-(3-fluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C#N)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)F)S1 AYBBZFKTQHXGRA-UHFFFAOYSA-N 0.000 claims 1
- RKWCKMRWRMBMHD-UHFFFAOYSA-N 5-(5-cyano-2-methylphenyl)-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CC=C(C#N)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)C)S1 RKWCKMRWRMBMHD-UHFFFAOYSA-N 0.000 claims 1
- ZYPDOLOIVUQBHA-UHFFFAOYSA-N 5-[2-chloro-5-(trifluoromethyl)phenyl]-n-(2,6-difluorophenyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC(F)=C1NC(=O)C1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S1 ZYPDOLOIVUQBHA-UHFFFAOYSA-N 0.000 claims 1
- GZQRIUNYAKGDOX-UHFFFAOYSA-N 5-[2-chloro-5-(trifluoromethyl)phenyl]-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CN=CC=C1NC(=O)C1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S1 GZQRIUNYAKGDOX-UHFFFAOYSA-N 0.000 claims 1
- XBWNZVFKRWKSBP-UHFFFAOYSA-N 5-[2-ethyl-5-(trifluoromethyl)phenyl]-n-(3-fluoropyridin-4-yl)thiophene-2-carboxamide Chemical compound CCC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)F)S1 XBWNZVFKRWKSBP-UHFFFAOYSA-N 0.000 claims 1
- JYQDNGRDKIYQQC-UHFFFAOYSA-N 5-[2-ethyl-5-(trifluoromethyl)phenyl]-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CCC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2)C)S1 JYQDNGRDKIYQQC-UHFFFAOYSA-N 0.000 claims 1
- OKDINCQPRYXHSL-UHFFFAOYSA-N 5-[5-(furan-2-yl)-2-methoxypyridin-3-yl]-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(C=2OC=CC=2)C=C1C(S1)=CC=C1C(=O)NC1=CC=NC=C1C OKDINCQPRYXHSL-UHFFFAOYSA-N 0.000 claims 1
- FDQOESXHIHKIGV-UHFFFAOYSA-N 5-[5-(furan-3-yl)-2-methoxypyridin-3-yl]-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound COC1=NC=C(C2=COC=C2)C=C1C(S1)=CC=C1C(=O)NC1=CC=NC=C1C FDQOESXHIHKIGV-UHFFFAOYSA-N 0.000 claims 1
- VSBQYZXBNQEHLV-UHFFFAOYSA-N ClC1(C(C=CC=C1)C1=CC=C(S1)NC(C1=C(C=NC=C1)C)=O)C=1OC=NN1 Chemical compound ClC1(C(C=CC=C1)C1=CC=C(S1)NC(C1=C(C=NC=C1)C)=O)C=1OC=NN1 VSBQYZXBNQEHLV-UHFFFAOYSA-N 0.000 claims 1
- 102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 claims 1
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 claims 1
- 206010061598 Immunodeficiency Diseases 0.000 claims 1
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 1
- 108090000176 Interleukin-13 Proteins 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- 108090000978 Interleukin-4 Proteins 0.000 claims 1
- 108010002616 Interleukin-5 Proteins 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
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000016396 cytokine production Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- VTTVLIMPVVYGMM-UHFFFAOYSA-N ethyl 3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]-4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 VTTVLIMPVVYGMM-UHFFFAOYSA-N 0.000 claims 1
- VADOEKDINFXHTJ-UHFFFAOYSA-N ethyl 4-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OCC)=CC=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 VADOEKDINFXHTJ-UHFFFAOYSA-N 0.000 claims 1
- IYNWLRQDGPVPGP-UHFFFAOYSA-N ethyl 4-chloro-3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 IYNWLRQDGPVPGP-UHFFFAOYSA-N 0.000 claims 1
- ZSNNOVGLLCRCKD-UHFFFAOYSA-N ethyl 4-chloro-3-[5-[(3,5-difluoropyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2F)F)=C1 ZSNNOVGLLCRCKD-UHFFFAOYSA-N 0.000 claims 1
- DEJAQEQQWYEFPN-UHFFFAOYSA-N ethyl 4-chloro-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 DEJAQEQQWYEFPN-UHFFFAOYSA-N 0.000 claims 1
- HXFXAPUMGFSCQK-UHFFFAOYSA-N ethyl 4-methyl-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 HXFXAPUMGFSCQK-UHFFFAOYSA-N 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000007813 immunodeficiency Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- GQZXIYHNNGWDGX-UHFFFAOYSA-N methyl 3-[5-[(2,6-difluorobenzoyl)amino]thiophen-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2SC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 GQZXIYHNNGWDGX-UHFFFAOYSA-N 0.000 claims 1
- CYEJEUFHAKJVMF-UHFFFAOYSA-N methyl 3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 CYEJEUFHAKJVMF-UHFFFAOYSA-N 0.000 claims 1
- ORUKKECDBDGFIM-UHFFFAOYSA-N methyl 3-[5-[(3,5-difluoropyridin-4-yl)carbamoyl]thiophen-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2F)F)=C1 ORUKKECDBDGFIM-UHFFFAOYSA-N 0.000 claims 1
- REQQGAUMSBGJPI-UHFFFAOYSA-N methyl 4-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 REQQGAUMSBGJPI-UHFFFAOYSA-N 0.000 claims 1
- QFLYFAOOVUOQHD-UHFFFAOYSA-N methyl 4-chloro-3-[5-[(2,6-difluorophenyl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=C1 QFLYFAOOVUOQHD-UHFFFAOYSA-N 0.000 claims 1
- CQMXPXDTNXHFFE-UHFFFAOYSA-N methyl 4-chloro-3-[5-[(3,5-difluoropyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2F)F)=C1 CQMXPXDTNXHFFE-UHFFFAOYSA-N 0.000 claims 1
- ORYPORMNFULBEL-UHFFFAOYSA-N methyl 4-chloro-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 ORYPORMNFULBEL-UHFFFAOYSA-N 0.000 claims 1
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- LBHGTPYMPASOAI-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-methyl-5-(trifluoromethyl)phenyl]thiophene-2-carboxamide Chemical compound CC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(=O)NC=2C(=CC=CC=2F)F)S1 LBHGTPYMPASOAI-UHFFFAOYSA-N 0.000 claims 1
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- LZQCXRBGAIZPSU-UHFFFAOYSA-N n-(3,5-difluoropyridin-4-yl)-5-[2-ethyl-5-(trifluoromethyl)phenyl]thiophene-2-carboxamide Chemical compound CCC1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(=O)NC=2C(=CN=CC=2F)F)S1 LZQCXRBGAIZPSU-UHFFFAOYSA-N 0.000 claims 1
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- DASXDCLBRXVGGF-UHFFFAOYSA-N n-(3,5-difluoropyridin-4-yl)-5-[5-(furan-2-yl)-2-methoxypyridin-3-yl]thiophene-2-carboxamide Chemical compound COC1=NC=C(C=2OC=CC=2)C=C1C(S1)=CC=C1C(=O)NC1=C(F)C=NC=C1F DASXDCLBRXVGGF-UHFFFAOYSA-N 0.000 claims 1
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- DUKQNODGMHRAAR-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-5-[5-(furan-2-yl)-2-methoxypyridin-3-yl]thiophene-2-carboxamide Chemical compound COC1=NC=C(C=2OC=CC=2)C=C1C(S1)=CC=C1C(=O)NC1=CC=NC=C1F DUKQNODGMHRAAR-UHFFFAOYSA-N 0.000 claims 1
- DTLUVEHGHFVLKK-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-5-[5-(furan-3-yl)-2-methoxypyridin-3-yl]thiophene-2-carboxamide Chemical compound COC1=NC=C(C2=COC=C2)C=C1C(S1)=CC=C1C(=O)NC1=CC=NC=C1F DTLUVEHGHFVLKK-UHFFFAOYSA-N 0.000 claims 1
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- ZVFJVCLFOLOFQU-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]thiophen-2-yl]-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)S1 ZVFJVCLFOLOFQU-UHFFFAOYSA-N 0.000 claims 1
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- SCXRCDWGJSDYGZ-UHFFFAOYSA-N propyl 4-chloro-3-[5-[(3,5-difluoropyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2F)F)=C1 SCXRCDWGJSDYGZ-UHFFFAOYSA-N 0.000 claims 1
- JVMLBUUWXUFVHQ-UHFFFAOYSA-N propyl 4-chloro-3-[5-[(3-methylpyridin-4-yl)carbamoyl]thiophen-2-yl]benzoate Chemical compound CCCOC(=O)C1=CC=C(Cl)C(C=2SC(=CC=2)C(=O)NC=2C(=CN=CC=2)C)=C1 JVMLBUUWXUFVHQ-UHFFFAOYSA-N 0.000 claims 1
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| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
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-
2006
- 2006-01-25 TW TW095102770A patent/TWI444187B/zh not_active IP Right Cessation
- 2006-01-25 WO PCT/US2006/002872 patent/WO2006081389A1/en not_active Ceased
- 2006-01-25 CA CA2595000A patent/CA2595000C/en not_active Expired - Fee Related
- 2006-01-25 US US11/340,292 patent/US8802721B2/en not_active Expired - Fee Related
- 2006-01-25 AU AU2006208043A patent/AU2006208043B2/en not_active Ceased
- 2006-01-25 EP EP06719650A patent/EP1846388A4/en not_active Withdrawn
- 2006-01-25 JP JP2007552413A patent/JP5221147B2/ja not_active Expired - Fee Related
-
2013
- 2013-01-11 JP JP2013003649A patent/JP2013064019A/ja active Pending
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