JP2009525285A5 - - Google Patents
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- JP2009525285A5 JP2009525285A5 JP2008552512A JP2008552512A JP2009525285A5 JP 2009525285 A5 JP2009525285 A5 JP 2009525285A5 JP 2008552512 A JP2008552512 A JP 2008552512A JP 2008552512 A JP2008552512 A JP 2008552512A JP 2009525285 A5 JP2009525285 A5 JP 2009525285A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- pyridin
- methyl
- phenyl
- 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 19
- -1 1H- pyrrolyl Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- HUKGURSOGGLRID-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F HUKGURSOGGLRID-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000005931 immune cell recruitment Effects 0.000 claims 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- SBKMPASLFIDIMS-UHFFFAOYSA-N n-[6-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]pyridin-3-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)N=C1 SBKMPASLFIDIMS-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- NWRLYMCEXWWZLA-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-[3-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]benzamide Chemical compound N=1C=C(C=2C=C(C=CC=2)C=2OC=CN=2)C(C)=CC=1NC(=O)C1=C(F)C=CC=C1F NWRLYMCEXWWZLA-UHFFFAOYSA-N 0.000 claims 1
- PPZYEZLVXHVDSH-UHFFFAOYSA-N 2,6-difluoro-n-[4-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]benzamide Chemical compound N=1C=C(C=2C=C(C=CC=2)C(F)(F)F)C(C)=CC=1NC(=O)C1=C(F)C=CC=C1F PPZYEZLVXHVDSH-UHFFFAOYSA-N 0.000 claims 1
- DECYQMUKHWDJJI-UHFFFAOYSA-N 2,6-difluoro-n-[5-(2-methyl-5-thiophen-2-ylphenyl)pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2SC=CC=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F DECYQMUKHWDJJI-UHFFFAOYSA-N 0.000 claims 1
- AXLXYUOGKRLVIH-UHFFFAOYSA-N 2,6-difluoro-n-[5-(2-methyl-5-thiophen-3-ylphenyl)pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C2=CSC=C2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F AXLXYUOGKRLVIH-UHFFFAOYSA-N 0.000 claims 1
- AFXMSIAEHKKZLP-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F AFXMSIAEHKKZLP-UHFFFAOYSA-N 0.000 claims 1
- NDWUBCJZNAEUBW-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3,4-thiadiazol-2-yl)phenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2SC=NN=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F NDWUBCJZNAEUBW-UHFFFAOYSA-N 0.000 claims 1
- GFASVRXBQQSUKC-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F GFASVRXBQQSUKC-UHFFFAOYSA-N 0.000 claims 1
- UUNLGJFURFVLBP-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2OC=NC=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F UUNLGJFURFVLBP-UHFFFAOYSA-N 0.000 claims 1
- VKCMJRXAMSLXOS-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F VKCMJRXAMSLXOS-UHFFFAOYSA-N 0.000 claims 1
- QTROTQGBZQYHBX-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(3-methyl-1,2-oxazol-5-yl)phenyl]pyridin-2-yl]benzamide Chemical compound O1N=C(C)C=C1C1=CC=C(C)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 QTROTQGBZQYHBX-UHFFFAOYSA-N 0.000 claims 1
- FSYLOFPFHBRJNF-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(furan-2-yl)-2-methylphenyl]pyridin-2-yl]benzamide Chemical compound CC1=CC=C(C=2OC=CC=2)C=C1C(C=N1)=CC=C1NC(=O)C1=C(F)C=CC=C1F FSYLOFPFHBRJNF-UHFFFAOYSA-N 0.000 claims 1
- CWUWPDDXRAXIQQ-UHFFFAOYSA-N 2,6-difluoro-n-[6-(2-methyl-5-pyridin-2-ylphenyl)pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2N=CC=CC=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F CWUWPDDXRAXIQQ-UHFFFAOYSA-N 0.000 claims 1
- LMYUUBFMCJMOLR-UHFFFAOYSA-N 2,6-difluoro-n-[6-(2-methyl-5-pyridin-3-ylphenyl)pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2C=NC=CC=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F LMYUUBFMCJMOLR-UHFFFAOYSA-N 0.000 claims 1
- NMEWXDIZTZGHPI-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2ON=CC=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F NMEWXDIZTZGHPI-UHFFFAOYSA-N 0.000 claims 1
- JOTOQEHANOQEIZ-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,3,4-oxadiazol-2-yl)phenyl]pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2OC=NN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F JOTOQEHANOQEIZ-UHFFFAOYSA-N 0.000 claims 1
- GDBAUFJPNSYWPV-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F GDBAUFJPNSYWPV-UHFFFAOYSA-N 0.000 claims 1
- CLOSKACXUFZBRR-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyridin-3-yl]benzamide;hydrochloride Chemical compound Cl.CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F CLOSKACXUFZBRR-UHFFFAOYSA-N 0.000 claims 1
- YWHOFKIZMLMQPA-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2OC=NC=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F YWHOFKIZMLMQPA-UHFFFAOYSA-N 0.000 claims 1
- HRTIYJHWFWOWGT-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyridin-3-yl]benzamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F HRTIYJHWFWOWGT-UHFFFAOYSA-N 0.000 claims 1
- DIMXDMFCZWDJBH-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyridin-3-yl]benzamide;hydrochloride Chemical compound Cl.CC1=CC=C(C=2SC=CN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F DIMXDMFCZWDJBH-UHFFFAOYSA-N 0.000 claims 1
- XRUZPDHALZTTLS-UHFFFAOYSA-N 2,6-difluoro-n-[6-[2-methyl-5-(3-methyl-1,2-oxazol-5-yl)phenyl]pyridin-3-yl]benzamide Chemical compound O1N=C(C)C=C1C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 XRUZPDHALZTTLS-UHFFFAOYSA-N 0.000 claims 1
- PXMZSZIIVMKPMX-UHFFFAOYSA-N 2,6-difluoro-n-[6-methyl-5-[3-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]benzamide Chemical compound C=1C=C(C=2C=C(C=CC=2)C=2OC=CN=2)C(C)=NC=1NC(=O)C1=C(F)C=CC=C1F PXMZSZIIVMKPMX-UHFFFAOYSA-N 0.000 claims 1
- YJZGPENRMVMIKP-UHFFFAOYSA-N 2,6-difluoro-n-[6-methyl-5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]benzamide Chemical compound C=1C=C(C=2C=C(C=CC=2)C(F)(F)F)C(C)=NC=1NC(=O)C1=C(F)C=CC=C1F YJZGPENRMVMIKP-UHFFFAOYSA-N 0.000 claims 1
- QPGVCUFOTYDIML-UHFFFAOYSA-N 2-methoxyethyl 4-chloro-3-[6-[(2,6-difluorobenzoyl)amino]pyridin-3-yl]benzoate Chemical compound COCCOC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 QPGVCUFOTYDIML-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- DFRZBDVAEKXKQC-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C DFRZBDVAEKXKQC-UHFFFAOYSA-N 0.000 claims 1
- RWVJIELCHYOVTM-UHFFFAOYSA-N 3-methyl-n-[5-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyridin-2-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(C=N1)=CC=C1NC(=O)C1=CC=NC=C1C RWVJIELCHYOVTM-UHFFFAOYSA-N 0.000 claims 1
- GVCJBMBKQOHNOI-UHFFFAOYSA-N 3-methyl-n-[6-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyridin-3-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=CC=NC=C1C GVCJBMBKQOHNOI-UHFFFAOYSA-N 0.000 claims 1
- FVTLFUPVOZVCQU-UHFFFAOYSA-N 3-methyl-n-[6-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]pyridin-3-yl]pyridine-4-carboxamide Chemical compound CC1=CC=C(C=2SC=CN=2)C=C1C(N=C1)=CC=C1NC(=O)C1=CC=NC=C1C FVTLFUPVOZVCQU-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JQNAMYQJPCVENO-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,2-oxazol-5-yl)phenyl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C=2C(=CC=C(C=2)C=2ON=CC=2)C)=C1C JQNAMYQJPCVENO-UHFFFAOYSA-N 0.000 claims 1
- HXPHZSJYBMNISB-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C1C HXPHZSJYBMNISB-UHFFFAOYSA-N 0.000 claims 1
- IYXMATXDEXCCEZ-UHFFFAOYSA-N 4-methyl-n-[5-[2-methyl-5-(1,3-oxazol-5-yl)phenyl]pyridin-2-yl]thiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=NC=2)C)=C1C IYXMATXDEXCCEZ-UHFFFAOYSA-N 0.000 claims 1
- 102000004310 Ion Channels Human genes 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 125000003545 alkoxy group Chemical group 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
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000016396 cytokine production Effects 0.000 claims 1
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- VCXCABXNVFWRFB-UHFFFAOYSA-N ethyl 3-[5-[(2,6-difluorobenzoyl)amino]pyridin-2-yl]-4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 VCXCABXNVFWRFB-UHFFFAOYSA-N 0.000 claims 1
- NRDRFIQYLSOEAF-UHFFFAOYSA-N ethyl 3-[6-[(2,6-difluorobenzoyl)amino]pyridin-3-yl]-4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 NRDRFIQYLSOEAF-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 125000005945 imidazopyridyl group Chemical group 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- NVPYSBKSCXMVNN-UHFFFAOYSA-N methyl 3-(6-benzamidopyridin-3-yl)-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C=CC=CC=3)=CC=2)=C1 NVPYSBKSCXMVNN-UHFFFAOYSA-N 0.000 claims 1
- ZZNOORNVLCYZKC-UHFFFAOYSA-N methyl 3-[5-[(2,6-difluorobenzoyl)amino]pyridin-2-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 ZZNOORNVLCYZKC-UHFFFAOYSA-N 0.000 claims 1
- JPJHHRSRUNCLIC-UHFFFAOYSA-N methyl 3-[6-[(2,6-difluorobenzoyl)amino]pyridin-3-yl]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 JPJHHRSRUNCLIC-UHFFFAOYSA-N 0.000 claims 1
- PMVUKTOGYNHOCP-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(2,6-difluorobenzoyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 PMVUKTOGYNHOCP-UHFFFAOYSA-N 0.000 claims 1
- OVVKGXGJVOEFKO-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(2-methylbenzoyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3)C)=CC=2)=C1 OVVKGXGJVOEFKO-UHFFFAOYSA-N 0.000 claims 1
- MONSMYXYRROOLM-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(2-methylpyrazole-3-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3N(N=CC=3)C)=CC=2)=C1 MONSMYXYRROOLM-UHFFFAOYSA-N 0.000 claims 1
- PWGFEFJUORGBNN-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(3-chloropyridine-4-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CN=CC=3)Cl)=CC=2)=C1 PWGFEFJUORGBNN-UHFFFAOYSA-N 0.000 claims 1
- VIZUGRMYZZKELJ-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(3-fluoropyridine-4-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CN=CC=3)F)=CC=2)=C1 VIZUGRMYZZKELJ-UHFFFAOYSA-N 0.000 claims 1
- JNQZFAQLBXIJMV-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(3-methylpyridine-4-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CN=CC=3)C)=CC=2)=C1 JNQZFAQLBXIJMV-UHFFFAOYSA-N 0.000 claims 1
- NXLSRFDUTSDIRS-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(4-fluoro-1,2-thiazole-5-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(C=NS3)F)=CC=2)=C1 NXLSRFDUTSDIRS-UHFFFAOYSA-N 0.000 claims 1
- QSBOIJNFSPYSFK-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(4-methyl-1,2-thiazole-5-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(C=NS3)C)=CC=2)=C1 QSBOIJNFSPYSFK-UHFFFAOYSA-N 0.000 claims 1
- LKNDFABBDHYNEP-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(4-methyl-1,3-oxazole-5-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(N=CO3)C)=CC=2)=C1 LKNDFABBDHYNEP-UHFFFAOYSA-N 0.000 claims 1
- POILPMPGOFDIBJ-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(4-methyl-1,3-thiazole-5-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(N=CS3)C)=CC=2)=C1 POILPMPGOFDIBJ-UHFFFAOYSA-N 0.000 claims 1
- BDNCMUFNBFWVPT-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(4-methyloxadiazole-5-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(N=NO3)C)=CC=2)=C1 BDNCMUFNBFWVPT-UHFFFAOYSA-N 0.000 claims 1
- HGWVNXUNRDPTPZ-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(4-methylthiadiazole-5-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(N=NS3)C)=CC=2)=C1 HGWVNXUNRDPTPZ-UHFFFAOYSA-N 0.000 claims 1
- PNVXQZPEXYZIDB-UHFFFAOYSA-N methyl 4-chloro-3-[6-[(5-methyl-2h-triazole-4-carbonyl)amino]pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3=C(N=NN3)C)=CC=2)=C1 PNVXQZPEXYZIDB-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- BCBUQGAHIXDSRR-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3,4-oxadiazol-2-yl)phenyl]pyridin-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=NN=2)Cl)C=N1 BCBUQGAHIXDSRR-UHFFFAOYSA-N 0.000 claims 1
- YFKOUVPVUCHLRB-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)C=N1 YFKOUVPVUCHLRB-UHFFFAOYSA-N 0.000 claims 1
- HIQSJMONWYATQC-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyridin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)=C1C HIQSJMONWYATQC-UHFFFAOYSA-N 0.000 claims 1
- MUHGILOXUDSEMX-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]pyridin-2-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)C=N1 MUHGILOXUDSEMX-UHFFFAOYSA-N 0.000 claims 1
- YYJYEZBUXSUCCB-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]pyridin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)C=N1 YYJYEZBUXSUCCB-UHFFFAOYSA-N 0.000 claims 1
- ZBWYIUFYKIJVSX-UHFFFAOYSA-N n-[5-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]pyridin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)=C1C ZBWYIUFYKIJVSX-UHFFFAOYSA-N 0.000 claims 1
- RJKJOLTUDYXIOB-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]-4-methylpyridin-2-yl]-2,6-difluorobenzamide Chemical compound N=1C=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C(C)=CC=1NC(=O)C1=C(F)C=CC=C1F RJKJOLTUDYXIOB-UHFFFAOYSA-N 0.000 claims 1
- DWMOXGJVPXQFEV-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]-6-methylpyridin-2-yl]-2,6-difluorobenzamide Chemical compound C=1C=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C(C)=NC=1NC(=O)C1=C(F)C=CC=C1F DWMOXGJVPXQFEV-UHFFFAOYSA-N 0.000 claims 1
- ZSRKPIVYJAAJLH-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyridin-2-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)C=N1 ZSRKPIVYJAAJLH-UHFFFAOYSA-N 0.000 claims 1
- ZSDHPTIXDDQFJZ-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyridin-2-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 ZSDHPTIXDDQFJZ-UHFFFAOYSA-N 0.000 claims 1
- UZHIPMFSDLICEF-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyridin-2-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=N1 UZHIPMFSDLICEF-UHFFFAOYSA-N 0.000 claims 1
- QHDJCQMCUAFTJE-UHFFFAOYSA-N n-[5-[2-chloro-5-(trifluoromethyl)phenyl]pyridin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2N=CC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1C QHDJCQMCUAFTJE-UHFFFAOYSA-N 0.000 claims 1
- RHKBALATTMMDIE-UHFFFAOYSA-N n-[5-[2-methoxy-5-(1,3-oxazol-5-yl)phenyl]pyridin-2-yl]-4-methylthiadiazole-5-carboxamide Chemical compound COC1=CC=C(C=2OC=NC=2)C=C1C(C=N1)=CC=C1NC(=O)C=1SN=NC=1C RHKBALATTMMDIE-UHFFFAOYSA-N 0.000 claims 1
- YEJSTDZSZXYVEO-UHFFFAOYSA-N n-[6-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyridin-3-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)N=C1 YEJSTDZSZXYVEO-UHFFFAOYSA-N 0.000 claims 1
- OLKOFYQDUSHFFU-UHFFFAOYSA-N n-[6-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]pyridin-3-yl]-2,6-difluorobenzamide;hydrochloride Chemical compound Cl.FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)Cl)N=C1 OLKOFYQDUSHFFU-UHFFFAOYSA-N 0.000 claims 1
- WQUKFVBMUDKEKA-UHFFFAOYSA-N n-[6-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]pyridin-3-yl]-2,6-difluorobenzamide;hydrochloride Chemical compound Cl.FC1=CC=CC(F)=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)N=C1 WQUKFVBMUDKEKA-UHFFFAOYSA-N 0.000 claims 1
- HVNRRCFINXZRFF-UHFFFAOYSA-N n-[6-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]pyridin-3-yl]-3-methylpyridine-4-carboxamide Chemical compound CC1=CN=CC=C1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2SC=CN=2)Cl)N=C1 HVNRRCFINXZRFF-UHFFFAOYSA-N 0.000 claims 1
- VUEMPTLOPXVARE-UHFFFAOYSA-N n-[6-[2-chloro-5-(trifluoromethyl)phenyl]pyridin-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=C1 VUEMPTLOPXVARE-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- ZYWCXXQEIBOVLJ-UHFFFAOYSA-N propyl 4-chloro-3-[6-[(2,6-difluorobenzoyl)amino]pyridin-3-yl]benzoate Chemical compound CCCOC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 ZYWCXXQEIBOVLJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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-
2007
- 2007-01-31 US US11/701,170 patent/US20070254926A1/en not_active Abandoned
- 2007-01-31 TW TW096103468A patent/TW200800188A/zh unknown
- 2007-01-31 WO PCT/US2007/002790 patent/WO2007089904A2/en not_active Ceased
- 2007-01-31 DK DK07762655.4T patent/DK1984338T3/da active
- 2007-01-31 CA CA002640049A patent/CA2640049A1/en not_active Abandoned
- 2007-01-31 AU AU2007211276A patent/AU2007211276B2/en not_active Ceased
- 2007-01-31 EP EP07762655.4A patent/EP1984338B8/en active Active
- 2007-01-31 JP JP2008552512A patent/JP5430944B2/ja not_active Expired - Fee Related
- 2007-01-31 ES ES07762655T patent/ES2403368T3/es active Active
- 2007-01-31 PL PL07762655T patent/PL1984338T3/pl unknown
-
2010
- 2010-03-29 US US12/749,317 patent/US8710083B2/en not_active Expired - Fee Related
-
2014
- 2014-03-12 US US14/206,059 patent/US20140187586A1/en not_active Abandoned
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