JP2018516254A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018516254A5 JP2018516254A5 JP2017561653A JP2017561653A JP2018516254A5 JP 2018516254 A5 JP2018516254 A5 JP 2018516254A5 JP 2017561653 A JP2017561653 A JP 2017561653A JP 2017561653 A JP2017561653 A JP 2017561653A JP 2018516254 A5 JP2018516254 A5 JP 2018516254A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- amino
- methanone
- phenyl
- benzonitrile
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 7
- -1 substituted Chemical class 0.000 claims 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- BZSFQWGXVZJHHW-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 BZSFQWGXVZJHHW-UHFFFAOYSA-N 0.000 claims 2
- LOGKQBGLVHZLCP-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidin-5-yl]methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NC1(CC1)C=1C=NC=NC=1 LOGKQBGLVHZLCP-UHFFFAOYSA-N 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- PWNZBAASKKTHKD-UHFFFAOYSA-N 3-[2-(pyridin-3-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=CC(=CC=C1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 PWNZBAASKKTHKD-UHFFFAOYSA-N 0.000 claims 2
- XFKDYJQBTISPOS-UHFFFAOYSA-N 3-[2-[(1-pyrazin-2-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=C(C=NC=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 XFKDYJQBTISPOS-UHFFFAOYSA-N 0.000 claims 2
- WLHYMEAMROQEIV-UHFFFAOYSA-N 3-[2-[(1-pyridin-3-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=CC(=CC=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 WLHYMEAMROQEIV-UHFFFAOYSA-N 0.000 claims 2
- OJUWWGHSEBTYGS-UHFFFAOYSA-N 3-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=CN=CC(=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 OJUWWGHSEBTYGS-UHFFFAOYSA-N 0.000 claims 2
- DRIOAXWEHSGQOM-UHFFFAOYSA-N 4-[[[5-[3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzamide Chemical compound FC(C=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=CC=1)(F)F DRIOAXWEHSGQOM-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- VMVMHPUREDQQQA-UHFFFAOYSA-N [2-(pyrazin-2-ylmethylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=C(C=NC=C1)CNC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F VMVMHPUREDQQQA-UHFFFAOYSA-N 0.000 claims 2
- IKEXSEJPRXVFPJ-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CC(=CC=C1)CNC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F IKEXSEJPRXVFPJ-UHFFFAOYSA-N 0.000 claims 2
- SNFIKXRRDPWTPT-UHFFFAOYSA-N [2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CN=CC(=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F SNFIKXRRDPWTPT-UHFFFAOYSA-N 0.000 claims 2
- KBMLPTBEXTYAKP-UHFFFAOYSA-N [2-[(6-methylpyridin-3-yl)methylamino]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound CC1=CC=C(C=N1)CNC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F KBMLPTBEXTYAKP-UHFFFAOYSA-N 0.000 claims 2
- OIUSSRUDUJXLNH-UHFFFAOYSA-N [4-fluoro-3-(trifluoromethyl)phenyl]-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound FC1=C(C=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1)C(F)(F)F OIUSSRUDUJXLNH-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- ZWFJYOCQOFGMLS-UHFFFAOYSA-N (1-methylindazol-5-yl)-[2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CN1N=CC2=CC(=CC=C12)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 ZWFJYOCQOFGMLS-UHFFFAOYSA-N 0.000 claims 1
- YHZVLKDGFBOZDR-UHFFFAOYSA-N (1-methylindazol-6-yl)-[2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CN1N=CC2=CC=C(C=C12)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 YHZVLKDGFBOZDR-UHFFFAOYSA-N 0.000 claims 1
- BAXFOZTZZUBQPS-UHFFFAOYSA-N (1-methylpyrazol-4-yl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CN1N=CC(=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 BAXFOZTZZUBQPS-UHFFFAOYSA-N 0.000 claims 1
- QLEBCZCOYOABML-UHFFFAOYSA-N (2-chlorophenyl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound ClC1=C(C=CC=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 QLEBCZCOYOABML-UHFFFAOYSA-N 0.000 claims 1
- LHRALRNRTFSAFD-UHFFFAOYSA-N (2-fluorophenyl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound FC1=C(C=CC=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 LHRALRNRTFSAFD-UHFFFAOYSA-N 0.000 claims 1
- UDAOFNIBKHOPKM-UHFFFAOYSA-N (2-methylquinolin-6-yl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CC1=NC2=CC=C(C=C2C=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 UDAOFNIBKHOPKM-UHFFFAOYSA-N 0.000 claims 1
- XVYVPEHJMUKZQA-UHFFFAOYSA-N (2-phenylmethoxypyrimidin-5-yl)-[3-(trifluoromethyl)phenyl]methanone Chemical compound C(C1=CC=CC=C1)OC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F XVYVPEHJMUKZQA-UHFFFAOYSA-N 0.000 claims 1
- YAAFHHBHGRNDAU-UHFFFAOYSA-N (3,4-difluorophenyl)-[2-(2-phenylpropan-2-ylamino)pyrimidin-5-yl]methanone Chemical compound FC=1C=C(C=CC=1F)C(=O)C=1C=NC(=NC=1)NC(C)(C)C1=CC=CC=C1 YAAFHHBHGRNDAU-UHFFFAOYSA-N 0.000 claims 1
- ORQAFBOXRPVLAZ-UHFFFAOYSA-N (3,4-difluorophenyl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound FC=1C=C(C=CC=1F)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 ORQAFBOXRPVLAZ-UHFFFAOYSA-N 0.000 claims 1
- CBOTVXQGQFTLFC-UHFFFAOYSA-N (3,4-difluorophenyl)-[2-[(4-methoxyphenyl)methylamino]pyrimidin-5-yl]methanone Chemical compound FC=1C=C(C=CC=1F)C(=O)C=1C=NC(=NC=1)NCC1=CC=C(C=C1)OC CBOTVXQGQFTLFC-UHFFFAOYSA-N 0.000 claims 1
- CNHIYUMHLCGGJZ-UHFFFAOYSA-N (3-chlorophenyl)-[2-(2-phenylpropan-2-ylamino)pyrimidin-5-yl]methanone Chemical compound ClC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NC(C)(C)C1=CC=CC=C1 CNHIYUMHLCGGJZ-UHFFFAOYSA-N 0.000 claims 1
- JYVRZPMQHRABJZ-UHFFFAOYSA-N (3-chlorophenyl)-[2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]methanone Chemical compound ClC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC1=CC=C(C=C1)F JYVRZPMQHRABJZ-UHFFFAOYSA-N 0.000 claims 1
- HMEYDDDTXFFUAO-UHFFFAOYSA-N (3-methoxyphenyl)-[2-(1-pyrimidin-5-ylethylamino)pyrimidin-5-yl]methanone Chemical compound COC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NC(C)C=1C=NC=NC=1 HMEYDDDTXFFUAO-UHFFFAOYSA-N 0.000 claims 1
- XSXULTISXSMVTK-UHFFFAOYSA-N (3-methoxyphenyl)-[2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound COC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 XSXULTISXSMVTK-UHFFFAOYSA-N 0.000 claims 1
- XISOVJXHGTWKNR-UHFFFAOYSA-N (3-methoxyphenyl)-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidin-5-yl]methanone Chemical compound COC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NC1(CC1)C=1C=NC=NC=1 XISOVJXHGTWKNR-UHFFFAOYSA-N 0.000 claims 1
- PANWWXYCRZFFGW-UHFFFAOYSA-N (3-methylphenyl)-[2-(pyridin-2-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC1=NC=CC=C1 PANWWXYCRZFFGW-UHFFFAOYSA-N 0.000 claims 1
- QUFWCLLJSUHQDF-UHFFFAOYSA-N (3-methylphenyl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 QUFWCLLJSUHQDF-UHFFFAOYSA-N 0.000 claims 1
- UIPITXGFIQSTPQ-UHFFFAOYSA-N (3-methylphenyl)-[2-(pyridin-4-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CC=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC1=CC=NC=C1 UIPITXGFIQSTPQ-UHFFFAOYSA-N 0.000 claims 1
- FANUUQWWWRVXJE-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(pyridazin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC=1N=NC=CC=1 FANUUQWWWRVXJE-UHFFFAOYSA-N 0.000 claims 1
- JWHGWYIWZYOKIO-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 JWHGWYIWZYOKIO-UHFFFAOYSA-N 0.000 claims 1
- MSGNIYYOSFJXLG-UHFFFAOYSA-N (4-chlorophenyl)-[2-[(4-chlorophenyl)methylamino]pyrimidin-5-yl]methanone Chemical compound ClC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC=C(C=C2)Cl)C=C1 MSGNIYYOSFJXLG-UHFFFAOYSA-N 0.000 claims 1
- XOUQPSKQOSPKCW-UHFFFAOYSA-N (4-chlorophenyl)-[2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]methanone Chemical compound ClC1=CC=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC1=CC=C(C=C1)F XOUQPSKQOSPKCW-UHFFFAOYSA-N 0.000 claims 1
- ZDZUFAZHYMTHTQ-UHFFFAOYSA-N (4-chlorophenyl)-[2-[(4-methoxyphenyl)methylamino]pyrimidin-5-yl]methanone Chemical compound ClC1=CC=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC1=CC=C(C=C1)OC ZDZUFAZHYMTHTQ-UHFFFAOYSA-N 0.000 claims 1
- DLCJOHIRSZSWQF-UHFFFAOYSA-N (4-methoxyphenyl)-[2-(1-pyrimidin-5-ylethylamino)pyrimidin-5-yl]methanone Chemical compound COC1=CC=C(C=C1)C(=O)C=1C=NC(=NC=1)NC(C)C=1C=NC=NC=1 DLCJOHIRSZSWQF-UHFFFAOYSA-N 0.000 claims 1
- VCZLEUKDNDNGIU-UHFFFAOYSA-N (4-methoxyphenyl)-[2-(pyridin-2-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound COC1=CC=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC1=NC=CC=C1 VCZLEUKDNDNGIU-UHFFFAOYSA-N 0.000 claims 1
- TYPBKMBMCQJTKB-UHFFFAOYSA-N (4-methoxyphenyl)-[2-[(4-methoxyphenyl)methylamino]pyrimidin-5-yl]methanone Chemical compound COC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC=C(C=C2)OC)C=C1 TYPBKMBMCQJTKB-UHFFFAOYSA-N 0.000 claims 1
- CCGPEEMOCCWEIQ-UHFFFAOYSA-N (4-methoxyphenyl)-[2-[[4-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound COC1=CC=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC1=CC=C(C=C1)OC(F)(F)F CCGPEEMOCCWEIQ-UHFFFAOYSA-N 0.000 claims 1
- BVAPXLVKROWRGH-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-yl-[2-(2-phenylpropan-2-ylamino)pyrimidin-5-yl]methanone Chemical compound O1CCOC2=C1C=CC(=C2)C(=O)C=1C=NC(=NC=1)NC(C)(C)C1=CC=CC=C1 BVAPXLVKROWRGH-UHFFFAOYSA-N 0.000 claims 1
- KOOBRGTZZSEBQT-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-yl-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound O1CCOC2=C1C=CC(=C2)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 KOOBRGTZZSEBQT-UHFFFAOYSA-N 0.000 claims 1
- DLEUPGNCBIMSNI-UHFFFAOYSA-N 2-[3-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]phenyl]acetic acid Chemical compound N1=CN=CC(=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C=CC=1)CC(=O)O DLEUPGNCBIMSNI-UHFFFAOYSA-N 0.000 claims 1
- MVXLTJGGEMJHMN-UHFFFAOYSA-N 2-chloro-5-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound ClC1=C(C#N)C=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 MVXLTJGGEMJHMN-UHFFFAOYSA-N 0.000 claims 1
- UKDHZARBWOVIGP-UHFFFAOYSA-N 2-fluoro-5-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound FC1=C(C#N)C=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 UKDHZARBWOVIGP-UHFFFAOYSA-N 0.000 claims 1
- HMMYJWHQXJQCAB-UHFFFAOYSA-N 2-methoxy-5-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound COC1=C(C#N)C=C(C=C1)C(=O)C=1C=NC(=NC=1)NC1(CC1)C=1C=NC=NC=1 HMMYJWHQXJQCAB-UHFFFAOYSA-N 0.000 claims 1
- KZQKRSJPAVTXSD-UHFFFAOYSA-N 2-methyl-5-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound CC1=C(C#N)C=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 KZQKRSJPAVTXSD-UHFFFAOYSA-N 0.000 claims 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 claims 1
- QALUXDRBPVQKBM-UHFFFAOYSA-N 3-[2-(1-pyridin-3-ylethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=CC(=CC=C1)C(C)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 QALUXDRBPVQKBM-UHFFFAOYSA-N 0.000 claims 1
- VCAAYIIGVCSPBP-UHFFFAOYSA-N 3-[2-(2-phenylpropan-2-ylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound C1(=CC=CC=C1)C(C)(C)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 VCAAYIIGVCSPBP-UHFFFAOYSA-N 0.000 claims 1
- RXWGCAHYHQFVJH-UHFFFAOYSA-N 3-[2-(benzylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 RXWGCAHYHQFVJH-UHFFFAOYSA-N 0.000 claims 1
- FBLFEBHRISBQGZ-UHFFFAOYSA-N 3-[2-(oxan-4-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound O1CCC(CC1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 FBLFEBHRISBQGZ-UHFFFAOYSA-N 0.000 claims 1
- RQPBVAQLTFXMCV-UHFFFAOYSA-N 3-[2-(pyrazin-2-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=C(C=NC=C1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 RQPBVAQLTFXMCV-UHFFFAOYSA-N 0.000 claims 1
- MBYRMDHWCNWXMC-UHFFFAOYSA-N 3-[2-(pyridazin-3-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=NC(=CC=C1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 MBYRMDHWCNWXMC-UHFFFAOYSA-N 0.000 claims 1
- TUIMGCPMHJOPAF-UHFFFAOYSA-N 3-[2-(pyridazin-4-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=NC=C(C=C1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 TUIMGCPMHJOPAF-UHFFFAOYSA-N 0.000 claims 1
- HHMQWTNSTPXMDJ-UHFFFAOYSA-N 3-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzamide Chemical compound N1=CN=CC(=C1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C(=O)N)C=CC=1 HHMQWTNSTPXMDJ-UHFFFAOYSA-N 0.000 claims 1
- CRPAGROPHFVERB-UHFFFAOYSA-N 3-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound N1=CN=CC(=C1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 CRPAGROPHFVERB-UHFFFAOYSA-N 0.000 claims 1
- IPJPYVMHSGTJNY-UHFFFAOYSA-N 3-[2-[(1-methylpiperidin-4-yl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound CN1CCC(CC1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 IPJPYVMHSGTJNY-UHFFFAOYSA-N 0.000 claims 1
- AFWPPKALCNDYNE-UHFFFAOYSA-N 3-[2-[(1-phenylcyclobutyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound C1(=CC=CC=C1)C1(CCC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 AFWPPKALCNDYNE-UHFFFAOYSA-N 0.000 claims 1
- JEKMZYUDLRSXLF-UHFFFAOYSA-N 3-[2-[(1-phenylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound C1(=CC=CC=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 JEKMZYUDLRSXLF-UHFFFAOYSA-N 0.000 claims 1
- TYMRHSNFPSODQA-UHFFFAOYSA-N 3-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzamide Chemical compound N1=CN=CC(=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C(=O)N)C=CC=1 TYMRHSNFPSODQA-UHFFFAOYSA-N 0.000 claims 1
- QRKHMZJCJHRXSZ-UHFFFAOYSA-N 3-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzoic acid Chemical compound N1=CN=CC(=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C(=O)O)C=CC=1 QRKHMZJCJHRXSZ-UHFFFAOYSA-N 0.000 claims 1
- YFRGVARABLQVSA-UHFFFAOYSA-N 3-[2-[(2,4-difluorophenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound FC1=C(CNC2=NC=C(C=N2)C(=O)C=2C=C(C#N)C=CC=2)C=CC(=C1)F YFRGVARABLQVSA-UHFFFAOYSA-N 0.000 claims 1
- CFPRRUQQGKJWRH-UHFFFAOYSA-N 3-[2-[(2-aminopyrimidin-5-yl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound NC1=NC=C(C=N1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 CFPRRUQQGKJWRH-UHFFFAOYSA-N 0.000 claims 1
- OCMGSBSWBHCTCX-UHFFFAOYSA-N 3-[2-[(2-chlorophenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound ClC1=C(CNC2=NC=C(C=N2)C(=O)C=2C=C(C#N)C=CC=2)C=CC=C1 OCMGSBSWBHCTCX-UHFFFAOYSA-N 0.000 claims 1
- ONQKZFFGUGEAGJ-UHFFFAOYSA-N 3-[2-[(2-oxopiperidin-4-yl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound C1CNC(=O)CC1CNC2=NC=C(C=N2)C(=O)C3=CC=CC(=C3)C#N ONQKZFFGUGEAGJ-UHFFFAOYSA-N 0.000 claims 1
- VTBSCCAXSPGIKU-UHFFFAOYSA-N 3-[2-[(4-chlorophenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound ClC1=CC=C(CNC2=NC=C(C=N2)C(=O)C=2C=C(C#N)C=CC=2)C=C1 VTBSCCAXSPGIKU-UHFFFAOYSA-N 0.000 claims 1
- YBGJSFVYOWNROI-UHFFFAOYSA-N 3-[2-[(4-fluorophenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C=2C=C(C#N)C=CC=2)C=C1 YBGJSFVYOWNROI-UHFFFAOYSA-N 0.000 claims 1
- UMNNAOFLQQEAEW-UHFFFAOYSA-N 3-[2-[(4-hydroxycyclohexyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound OC1CCC(CC1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 UMNNAOFLQQEAEW-UHFFFAOYSA-N 0.000 claims 1
- SGQUNVZKFBFQRP-UHFFFAOYSA-N 3-[2-[(4-methoxyphenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound COC1=CC=C(CNC2=NC=C(C=N2)C(=O)C=2C=C(C#N)C=CC=2)C=C1 SGQUNVZKFBFQRP-UHFFFAOYSA-N 0.000 claims 1
- WLCDMHVLPWGHRP-UHFFFAOYSA-N 3-[2-[(6-aminopyridin-3-yl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound NC1=CC=C(C=N1)CNC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 WLCDMHVLPWGHRP-UHFFFAOYSA-N 0.000 claims 1
- MZYPHHZFXMWMOY-UHFFFAOYSA-N 3-[2-[[1-(5-aminopyrazin-2-yl)cyclopropyl]amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound NC=1N=CC(=NC=1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 MZYPHHZFXMWMOY-UHFFFAOYSA-N 0.000 claims 1
- LMBXIVRNMGOMKN-UHFFFAOYSA-N 3-[2-[[1-(6-oxo-1H-pyridin-3-yl)cyclopropyl]amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound OC1=CC=C(C=N1)C1(CC1)NC1=NC=C(C=N1)C(=O)C=1C=C(C#N)C=CC=1 LMBXIVRNMGOMKN-UHFFFAOYSA-N 0.000 claims 1
- WDDUDDZQQJPJLR-UHFFFAOYSA-N 3-[[(5-benzoylpyrimidin-2-yl)amino]methyl]benzonitrile Chemical compound C(C1=CC=CC=C1)(=O)C=1C=NC(=NC=1)NCC=1C=C(C#N)C=CC=1 WDDUDDZQQJPJLR-UHFFFAOYSA-N 0.000 claims 1
- SXUGNMTVRLBTRZ-UHFFFAOYSA-N 3-[[[5-(3-chlorobenzoyl)pyrimidin-2-yl]amino]methyl]benzamide Chemical compound ClC=1C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=C(C(=O)N)C=CC=2)C=CC=1 SXUGNMTVRLBTRZ-UHFFFAOYSA-N 0.000 claims 1
- WRQBVXLNJOLICB-UHFFFAOYSA-N 3-[[[5-(3-chlorobenzoyl)pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound ClC=1C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=C(C#N)C=CC=2)C=CC=1 WRQBVXLNJOLICB-UHFFFAOYSA-N 0.000 claims 1
- KJCNGRIFMDTUSO-UHFFFAOYSA-N 3-[[[5-(3-cyanobenzoyl)pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound C(#N)C=1C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=C(C#N)C=CC=2)C=CC=1 KJCNGRIFMDTUSO-UHFFFAOYSA-N 0.000 claims 1
- JQPOQROYCHAQQM-UHFFFAOYSA-N 3-[[[5-(4-methoxybenzoyl)pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound COC1=CC=C(C(=O)C=2C=NC(=NC=2)NCC=2C=C(C#N)C=CC=2)C=C1 JQPOQROYCHAQQM-UHFFFAOYSA-N 0.000 claims 1
- SXZCWPNJVJNMGU-UHFFFAOYSA-N 3-[[[5-[3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound FC(C=1C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=C(C#N)C=CC=2)C=CC=1)(F)F SXZCWPNJVJNMGU-UHFFFAOYSA-N 0.000 claims 1
- HWTRLXNZNISZEI-UHFFFAOYSA-N 3-chloro-5-[2-[(1-pyrimidin-5-ylcyclopropyl)amino]pyrimidine-5-carbonyl]benzonitrile Chemical compound ClC=1C=C(C#N)C=C(C=1)C(=O)C=1C=NC(=NC=1)NC1(CC1)C=1C=NC=NC=1 HWTRLXNZNISZEI-UHFFFAOYSA-N 0.000 claims 1
- DUOUWMVOBCMKQX-UHFFFAOYSA-N 3-fluoro-5-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound FC=1C=C(C#N)C=C(C=1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 DUOUWMVOBCMKQX-UHFFFAOYSA-N 0.000 claims 1
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims 1
- PZMCWUVNRFWFRE-ZDUSSCGKSA-N 4-[(1S)-1-[[5-(3-cyanobenzoyl)pyrimidin-2-yl]amino]ethyl]benzamide Chemical compound C[C@@H](C1=CC=C(C=C1)C(=O)N)NC2=NC=C(C=N2)C(=O)C3=CC=CC(=C3)C#N PZMCWUVNRFWFRE-ZDUSSCGKSA-N 0.000 claims 1
- PZMCWUVNRFWFRE-UHFFFAOYSA-N 4-[1-[[5-(3-cyanobenzoyl)pyrimidin-2-yl]amino]ethyl]benzamide Chemical compound C(#N)C=1C=C(C(=O)C=2C=NC(=NC=2)NC(C)C2=CC=C(C(=O)N)C=C2)C=CC=1 PZMCWUVNRFWFRE-UHFFFAOYSA-N 0.000 claims 1
- SKXZDUFCQPZRIZ-UHFFFAOYSA-N 4-[1-[[5-(4-methoxybenzoyl)pyrimidin-2-yl]amino]ethyl]benzamide Chemical compound COC1=CC=C(C(=O)C=2C=NC(=NC=2)NC(C)C2=CC=C(C(=O)N)C=C2)C=C1 SKXZDUFCQPZRIZ-UHFFFAOYSA-N 0.000 claims 1
- DRGLKFFYXQYJQR-UHFFFAOYSA-N 4-[2-[(4-fluorophenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC=C(C#N)C=C2)C=C1 DRGLKFFYXQYJQR-UHFFFAOYSA-N 0.000 claims 1
- RMYLCDCVATXICT-UHFFFAOYSA-N 4-[2-[(4-methoxyphenyl)methylamino]pyrimidine-5-carbonyl]benzonitrile Chemical compound COC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC=C(C#N)C=C2)C=C1 RMYLCDCVATXICT-UHFFFAOYSA-N 0.000 claims 1
- WSKZADREHBRCGQ-UHFFFAOYSA-N 4-[[(5-benzoylpyrimidin-2-yl)amino]methyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)C=1C=NC(=NC=1)NCC1=CC=C(C(=O)N)C=C1 WSKZADREHBRCGQ-UHFFFAOYSA-N 0.000 claims 1
- XBSUTFHKOASQBP-UHFFFAOYSA-N 4-[[[5-(3,4-difluorobenzoyl)pyrimidin-2-yl]amino]methyl]benzamide Chemical compound FC=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=CC=1F XBSUTFHKOASQBP-UHFFFAOYSA-N 0.000 claims 1
- QTTBGULQMQUIRD-UHFFFAOYSA-N 4-[[[5-(3,4-difluorobenzoyl)pyrimidin-2-yl]amino]methyl]benzoic acid Chemical compound FC=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)O)C=C2)C=CC=1F QTTBGULQMQUIRD-UHFFFAOYSA-N 0.000 claims 1
- JQOJNZLNKPEAHE-UHFFFAOYSA-N 4-[[[5-(3-cyanobenzoyl)pyrimidin-2-yl]amino]methyl]benzamide Chemical compound C(#N)C=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=CC=1 JQOJNZLNKPEAHE-UHFFFAOYSA-N 0.000 claims 1
- OXWMTLNRSGLBII-UHFFFAOYSA-N 4-[[[5-(3-methylbenzoyl)pyrimidin-2-yl]amino]methyl]benzamide Chemical compound CC=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=CC=1 OXWMTLNRSGLBII-UHFFFAOYSA-N 0.000 claims 1
- RCZZILFGRYAMBX-UHFFFAOYSA-N 4-[[[5-(3-methylbenzoyl)pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound CC=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C#N)C=C2)C=CC=1 RCZZILFGRYAMBX-UHFFFAOYSA-N 0.000 claims 1
- BSEGSCITAQVKLM-UHFFFAOYSA-N 4-[[[5-(3-methylsulfonylbenzoyl)pyrimidin-2-yl]amino]methyl]benzamide Chemical compound CS(=O)(=O)C=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=CC=1 BSEGSCITAQVKLM-UHFFFAOYSA-N 0.000 claims 1
- MDVMDFSDEZBTKJ-UHFFFAOYSA-N 4-[[[5-(3-methylsulfonylbenzoyl)pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound CS(=O)(=O)C=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C#N)C=C2)C=CC=1 MDVMDFSDEZBTKJ-UHFFFAOYSA-N 0.000 claims 1
- VLBZIPPOMAWXBD-UHFFFAOYSA-N 4-[[[5-(4-methoxybenzoyl)pyrimidin-2-yl]amino]methyl]benzamide Chemical compound COC1=CC=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=C1 VLBZIPPOMAWXBD-UHFFFAOYSA-N 0.000 claims 1
- IHXSXSSBAOUAGN-UHFFFAOYSA-N 4-[[[5-[3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound FC(C=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C#N)C=C2)C=CC=1)(F)F IHXSXSSBAOUAGN-UHFFFAOYSA-N 0.000 claims 1
- FLSKYAXJLPVWJU-UHFFFAOYSA-N 4-[[[5-[3-fluoro-5-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzamide Chemical compound FC=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=C(C=1)C(F)(F)F FLSKYAXJLPVWJU-UHFFFAOYSA-N 0.000 claims 1
- YSOPXWSDSFPTSH-UHFFFAOYSA-N 4-[[[5-[3-fluoro-5-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound FC=1C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C#N)C=C2)C=C(C=1)C(F)(F)F YSOPXWSDSFPTSH-UHFFFAOYSA-N 0.000 claims 1
- NVNHTTXXPAZLEE-UHFFFAOYSA-N 4-[[[5-[4-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound FC(C1=CC=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C#N)C=C2)C=C1)(F)F NVNHTTXXPAZLEE-UHFFFAOYSA-N 0.000 claims 1
- QYFWURBFRXMLNV-UHFFFAOYSA-N 4-[[[5-[4-fluoro-3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzamide Chemical compound FC1=C(C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)N)C=C2)C=C1)C(F)(F)F QYFWURBFRXMLNV-UHFFFAOYSA-N 0.000 claims 1
- NZXIAIOQULVVBP-UHFFFAOYSA-N 4-[[[5-[4-fluoro-3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzoic acid Chemical compound FC1=C(C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C(=O)O)C=C2)C=C1)C(F)(F)F NZXIAIOQULVVBP-UHFFFAOYSA-N 0.000 claims 1
- FDGVFOFDAOWJTD-UHFFFAOYSA-N 4-[[[5-[4-fluoro-3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]benzonitrile Chemical compound FC1=C(C=C(C(=O)C=2C=NC(=NC=2)NCC2=CC=C(C#N)C=C2)C=C1)C(F)(F)F FDGVFOFDAOWJTD-UHFFFAOYSA-N 0.000 claims 1
- TZTGMVKYCTVYTH-UHFFFAOYSA-N 4-fluoro-3-[2-(pyrimidin-5-ylmethylamino)pyrimidine-5-carbonyl]benzonitrile Chemical compound FC1=C(C=C(C#N)C=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 TZTGMVKYCTVYTH-UHFFFAOYSA-N 0.000 claims 1
- YFWUFOXBKOMRIL-UHFFFAOYSA-N 5-[1-[[5-(3-cyanobenzoyl)pyrimidin-2-yl]amino]cyclopropyl]pyridine-2-carboxamide Chemical compound C(#N)C=1C=C(C(=O)C=2C=NC(=NC=2)NC2(CC2)C=2C=CC(=NC=2)C(=O)N)C=CC=1 YFWUFOXBKOMRIL-UHFFFAOYSA-N 0.000 claims 1
- PMVDKOONVSTTIP-UHFFFAOYSA-N 5-[[(5-benzoylpyrimidin-2-yl)amino]methyl]pyridine-2-carboxamide Chemical compound C(C1=CC=CC=C1)(=O)C=1C=NC(=NC=1)NCC=1C=CC(=NC=1)C(=O)N PMVDKOONVSTTIP-UHFFFAOYSA-N 0.000 claims 1
- MOHVVJJMUQEZOI-UHFFFAOYSA-N 5-[[[5-(3-cyanobenzoyl)pyrimidin-2-yl]amino]methyl]pyridine-2-carboxamide Chemical compound C(#N)C=1C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=CC(=NC=2)C(=O)N)C=CC=1 MOHVVJJMUQEZOI-UHFFFAOYSA-N 0.000 claims 1
- WRYLDMHFUGEWOM-UHFFFAOYSA-N 5-[[[5-[3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]pyridine-2-carboxamide Chemical compound FC(C=1C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=CC(=NC=2)C(=O)N)C=CC=1)(F)F WRYLDMHFUGEWOM-UHFFFAOYSA-N 0.000 claims 1
- VFFJWNKFXGALME-UHFFFAOYSA-N 5-[[[5-[4-fluoro-3-(trifluoromethyl)benzoyl]pyrimidin-2-yl]amino]methyl]pyridine-2-carboxamide Chemical compound FC1=C(C=C(C(=O)C=2C=NC(=NC=2)NCC=2C=CC(=NC=2)C(=O)N)C=C1)C(F)(F)F VFFJWNKFXGALME-UHFFFAOYSA-N 0.000 claims 1
- FBFMBUPCEFDKRK-UHFFFAOYSA-N CC(C)(NC1=NC=C(C=N1)C(=O)C1=CC=CC(=C1)C(F)(F)F)C1=CN=NC=C1 Chemical compound CC(C)(NC1=NC=C(C=N1)C(=O)C1=CC=CC(=C1)C(F)(F)F)C1=CN=NC=C1 FBFMBUPCEFDKRK-UHFFFAOYSA-N 0.000 claims 1
- LWVHFGDDLLLYSL-UHFFFAOYSA-N CC(NC1=NC=C(C=N1)C(=O)C1=CC2=C(OCCO2)C=C1)C1=CN=CN=C1 Chemical compound CC(NC1=NC=C(C=N1)C(=O)C1=CC2=C(OCCO2)C=C1)C1=CN=CN=C1 LWVHFGDDLLLYSL-UHFFFAOYSA-N 0.000 claims 1
- JIHLPMCCFKNUBK-UHFFFAOYSA-N COC1=CC=CC(=C1)C(=O)C1=CN=C(CC2=CC=C(C=C2)N2CCN(C)CC2)N=C1 Chemical compound COC1=CC=CC(=C1)C(=O)C1=CN=C(CC2=CC=C(C=C2)N2CCN(C)CC2)N=C1 JIHLPMCCFKNUBK-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- NCQWGFRCCRQCAG-UHFFFAOYSA-N O=C(C1=CC=C2OCCOC2=C1)C1=CN=C(NCC2=CC=C(C=C2)C#N)N=C1 Chemical compound O=C(C1=CC=C2OCCOC2=C1)C1=CN=C(NCC2=CC=C(C=C2)C#N)N=C1 NCQWGFRCCRQCAG-UHFFFAOYSA-N 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- VPQSHZNXENRMQC-UHFFFAOYSA-N [2-(2-phenylpropan-2-ylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound C1(=CC=CC=C1)C(C)(C)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F VPQSHZNXENRMQC-UHFFFAOYSA-N 0.000 claims 1
- GECGLKMFQPIFMN-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC2=C(OCCO2)C=C1 GECGLKMFQPIFMN-UHFFFAOYSA-N 0.000 claims 1
- XKPCCSMSKOVQSN-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-(3-chlorophenyl)methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)Cl XKPCCSMSKOVQSN-UHFFFAOYSA-N 0.000 claims 1
- RCWGERSORXKHOL-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-(3-methylphenyl)methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C RCWGERSORXKHOL-UHFFFAOYSA-N 0.000 claims 1
- GVUOTURVJMPSER-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-(4-methoxyphenyl)methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC=C(C=C1)OC GVUOTURVJMPSER-UHFFFAOYSA-N 0.000 claims 1
- MXQHAKSHCGMWAU-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F MXQHAKSHCGMWAU-UHFFFAOYSA-N 0.000 claims 1
- HPEQTWLDAHPQCW-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-[3-fluoro-5-(trifluoromethyl)phenyl]methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC(=C1)C(F)(F)F)F HPEQTWLDAHPQCW-UHFFFAOYSA-N 0.000 claims 1
- VITJKLYMJCCHPO-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-[4-fluoro-3-(trifluoromethyl)phenyl]methanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC(=C(C=C1)F)C(F)(F)F VITJKLYMJCCHPO-UHFFFAOYSA-N 0.000 claims 1
- ODGMQVWKYQSDEM-UHFFFAOYSA-N [2-(benzylamino)pyrimidin-5-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=N1)C(=O)C1=CC=CC=C1 ODGMQVWKYQSDEM-UHFFFAOYSA-N 0.000 claims 1
- LQQDGXXWEHQEBS-UHFFFAOYSA-N [2-(pyridazin-3-ylmethylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=NC(=CC=C1)CNC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F LQQDGXXWEHQEBS-UHFFFAOYSA-N 0.000 claims 1
- MIEWHLOKPSRHGI-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound N1=CC(=CC=C1)CNC1=NC=C(C=N1)C(=O)C1=CC=C(C=C1)C(F)(F)F MIEWHLOKPSRHGI-UHFFFAOYSA-N 0.000 claims 1
- XXQGGYNRNJTVTN-UHFFFAOYSA-N [2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]-thiophen-2-ylmethanone Chemical compound N1=CC(=CC=C1)CNC1=NC=C(C=N1)C(=O)C=1SC=CC=1 XXQGGYNRNJTVTN-UHFFFAOYSA-N 0.000 claims 1
- SXGWZYNWYKBEQW-UHFFFAOYSA-N [2-(pyridin-4-ylmethylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CC=C(C=C1)CNC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F SXGWZYNWYKBEQW-UHFFFAOYSA-N 0.000 claims 1
- JJZHBSNPHMHROG-UHFFFAOYSA-N [2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]-[2-(trifluoromethyl)pyridin-4-yl]methanone Chemical compound N1=CN=CC(=C1)CNC1=NC=C(C=N1)C(=O)C1=CC(=NC=C1)C(F)(F)F JJZHBSNPHMHROG-UHFFFAOYSA-N 0.000 claims 1
- YXUQMWCGELHLOO-UHFFFAOYSA-N [2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CN=CC(=C1)CNC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F YXUQMWCGELHLOO-UHFFFAOYSA-N 0.000 claims 1
- XLWPFMGAVDXEOQ-UHFFFAOYSA-N [2-[(1-phenylcyclopropyl)amino]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound C1(=CC=CC=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F XLWPFMGAVDXEOQ-UHFFFAOYSA-N 0.000 claims 1
- GNFHKQQNWAUXGW-UHFFFAOYSA-N [2-[(1-pyridin-3-ylcyclopropyl)amino]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CC(=CC=C1)C1(CC1)NC1=NC=C(C=N1)C(=O)C1=CC(=CC=C1)C(F)(F)F GNFHKQQNWAUXGW-UHFFFAOYSA-N 0.000 claims 1
- VUDGJFDRSIQTLT-UHFFFAOYSA-N [2-[(2,4-difluorophenyl)methoxy]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC1=C(COC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=CC(=C1)F VUDGJFDRSIQTLT-UHFFFAOYSA-N 0.000 claims 1
- XCZWFRIANCZGOF-UHFFFAOYSA-N [2-[(2-fluorophenyl)methylamino]pyrimidin-5-yl]-phenylmethanone Chemical compound FC1=C(CNC2=NC=C(C=N2)C(=O)C2=CC=CC=C2)C=CC=C1 XCZWFRIANCZGOF-UHFFFAOYSA-N 0.000 claims 1
- WGBJVICIIKJPDI-UHFFFAOYSA-N [2-[(4-chloro-2-fluorophenyl)methylamino]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound ClC1=CC(=C(CNC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=C1)F WGBJVICIIKJPDI-UHFFFAOYSA-N 0.000 claims 1
- NJQIBJFYXOGCJT-UHFFFAOYSA-N [2-[(4-chlorophenyl)methoxy]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound ClC1=CC=C(COC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=C1 NJQIBJFYXOGCJT-UHFFFAOYSA-N 0.000 claims 1
- PINFLIZHILCPDD-UHFFFAOYSA-N [2-[(4-fluorophenyl)methoxy]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC1=CC=C(COC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=C1 PINFLIZHILCPDD-UHFFFAOYSA-N 0.000 claims 1
- VBHKWOOAFZYOCX-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]-(3-methoxyphenyl)methanone Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)OC)C=C1 VBHKWOOAFZYOCX-UHFFFAOYSA-N 0.000 claims 1
- AOIAZXAIBOFFCK-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]-(3-methylsulfonylphenyl)methanone Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)S(=O)(=O)C)C=C1 AOIAZXAIBOFFCK-UHFFFAOYSA-N 0.000 claims 1
- QVVMWNWZHCZLNC-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]-[3-fluoro-5-(trifluoromethyl)phenyl]methanone Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC(=CC(=C2)C(F)(F)F)F)C=C1 QVVMWNWZHCZLNC-UHFFFAOYSA-N 0.000 claims 1
- KBWVRCWYQSUQSY-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1 KBWVRCWYQSUQSY-UHFFFAOYSA-N 0.000 claims 1
- WOIDWAIDFQIOGK-UHFFFAOYSA-N [2-[(4-fluorophenyl)methylamino]pyrimidin-5-yl]-[4-fluoro-3-(trifluoromethyl)phenyl]methanone Chemical compound FC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC(=C(C=C2)F)C(F)(F)F)C=C1 WOIDWAIDFQIOGK-UHFFFAOYSA-N 0.000 claims 1
- IRVDTYYSNPLUEA-UHFFFAOYSA-N [2-[(4-methoxyphenyl)methoxy]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound COC1=CC=C(COC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=C1 IRVDTYYSNPLUEA-UHFFFAOYSA-N 0.000 claims 1
- IFUFEYZEFCQDGE-UHFFFAOYSA-N [2-[(4-methoxyphenyl)methylamino]pyrimidin-5-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound COC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1 IFUFEYZEFCQDGE-UHFFFAOYSA-N 0.000 claims 1
- SDRFJZQBHHBCFI-UHFFFAOYSA-N [2-[[4-(trifluoromethoxy)phenyl]methoxy]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(OC1=CC=C(COC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=C1)(F)F SDRFJZQBHHBCFI-UHFFFAOYSA-N 0.000 claims 1
- ZFDQTVYRHIFLOP-UHFFFAOYSA-N [2-[[4-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(OC1=CC=C(CNC2=NC=C(C=N2)C(=O)C2=CC(=CC=C2)C(F)(F)F)C=C1)(F)F ZFDQTVYRHIFLOP-UHFFFAOYSA-N 0.000 claims 1
- IRXNLGLTTUFJNZ-UHFFFAOYSA-N [3-fluoro-5-(trifluoromethyl)phenyl]-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 IRXNLGLTTUFJNZ-UHFFFAOYSA-N 0.000 claims 1
- OFXOTNYKPLUQRW-UHFFFAOYSA-N [4-fluoro-3-(trifluoromethyl)phenyl]-[2-(pyridin-2-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound FC1=C(C=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC1=NC=CC=C1)C(F)(F)F OFXOTNYKPLUQRW-UHFFFAOYSA-N 0.000 claims 1
- UHFDCKARLZDPRW-UHFFFAOYSA-N [4-fluoro-3-(trifluoromethyl)phenyl]-[2-(pyridin-4-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound FC1=C(C=C(C=C1)C(=O)C=1C=NC(=NC=1)NCC1=CC=NC=C1)C(F)(F)F UHFDCKARLZDPRW-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004452 carbocyclyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- ZLVXUGVMIDVPCM-UHFFFAOYSA-N phenyl-[2-(2-phenylpropan-2-ylamino)pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NC(C)(C)C1=CC=CC=C1 ZLVXUGVMIDVPCM-UHFFFAOYSA-N 0.000 claims 1
- NHRXWINZCGSXFX-UHFFFAOYSA-N phenyl-[2-(pyrazin-2-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NCC1=NC=CN=C1 NHRXWINZCGSXFX-UHFFFAOYSA-N 0.000 claims 1
- IBMIDUVNTDPVAD-UHFFFAOYSA-N phenyl-[2-(pyridazin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NCC=1N=NC=CC=1 IBMIDUVNTDPVAD-UHFFFAOYSA-N 0.000 claims 1
- GPZIOKLXQPNWCJ-UHFFFAOYSA-N phenyl-[2-(pyridin-3-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=CC=1 GPZIOKLXQPNWCJ-UHFFFAOYSA-N 0.000 claims 1
- NJQZXBYAOQGCID-UHFFFAOYSA-N phenyl-[2-(pyrimidin-5-ylmethylamino)pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NCC=1C=NC=NC=1 NJQZXBYAOQGCID-UHFFFAOYSA-N 0.000 claims 1
- WLMTYCICQXGBQR-UHFFFAOYSA-N phenyl-[2-[(1-phenylcyclopropyl)amino]pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NC1(CC1)C1=CC=CC=C1 WLMTYCICQXGBQR-UHFFFAOYSA-N 0.000 claims 1
- BRAFADNLUOELAK-UHFFFAOYSA-N phenyl-[2-[(1-pyridin-3-ylcyclopropyl)amino]pyrimidin-5-yl]methanone Chemical compound C1(=CC=CC=C1)C(=O)C=1C=NC(=NC=1)NC1(CC1)C=1C=NC=CC=1 BRAFADNLUOELAK-UHFFFAOYSA-N 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562167962P | 2015-05-29 | 2015-05-29 | |
| US62/167,962 | 2015-05-29 | ||
| US201562195005P | 2015-07-21 | 2015-07-21 | |
| US62/195,005 | 2015-07-21 | ||
| PCT/IB2016/052825 WO2016193844A1 (en) | 2015-05-29 | 2016-05-16 | Novel heterocyclic compounds as inhibitors of vanin-1 enzyme |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018516254A JP2018516254A (ja) | 2018-06-21 |
| JP2018516254A5 true JP2018516254A5 (https=) | 2019-05-23 |
Family
ID=56026933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017561653A Pending JP2018516254A (ja) | 2015-05-29 | 2016-05-16 | バニン１酵素の阻害薬としての新規なヘテロ環化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US10308615B2 (https=) |
| EP (1) | EP3303303A1 (https=) |
| JP (1) | JP2018516254A (https=) |
| CA (1) | CA2987179C (https=) |
| WO (1) | WO2016193844A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018011681A1 (en) * | 2016-07-14 | 2018-01-18 | Pfizer Inc. | Novel pyrimidine carboxamides as inhibitors of vanin-1 enzyme |
| WO2018119142A1 (en) | 2016-12-21 | 2018-06-28 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| US10961242B2 (en) | 2017-05-17 | 2021-03-30 | Legochem Biosciences, Inc. | Compounds as autotaxin inhibitors and pharmaceutical compositions comprising the same |
| KR101798840B1 (ko) | 2017-05-17 | 2017-11-17 | 주식회사 레고켐 바이오사이언스 | 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물 |
| AU2018285131B2 (en) * | 2017-06-12 | 2021-11-11 | Boehringer Ingelheim International Gmbh | Heteroaromatic compounds as Vanin inhibitors |
| US11723929B2 (en) | 2017-06-13 | 2023-08-15 | The Regents Of The University Of California | Methods of improving cell-based therapy |
| US11497723B1 (en) * | 2017-12-19 | 2022-11-15 | Tony Antakly | PPAR-gamma activators, HDAC inhibitors and their therapeutical usages |
| US10702488B2 (en) * | 2017-12-19 | 2020-07-07 | Theriac Biomedical Inc. | PPAR-γ activators, HDAC inhibitors and their therapeutical usages |
| WO2019133445A1 (en) * | 2017-12-28 | 2019-07-04 | Inception Ibd, Inc. | Aminothiazoles as inhibitors of vanin-1 |
| AU2019326933B2 (en) * | 2018-08-28 | 2024-12-05 | Boehringer Ingelheim International Gmbh | Heteroaromatic compounds as Vanin inhibitors |
| WO2020102575A1 (en) * | 2018-11-16 | 2020-05-22 | Inception Ibd, Inc. | Heterocyclic aminothiazoles and uses thereof |
| AU2019392524B2 (en) * | 2018-12-03 | 2025-05-08 | Boehringer Ingelheim International Gmbh | Heteroaromatic compounds as vanin inhibitors |
| US12358910B2 (en) | 2018-12-03 | 2025-07-15 | Boehringer Ingelheim International Gmbh | Heteroaromatic compounds as Vanin inhibitors |
| EA202191476A1 (ru) * | 2018-12-03 | 2021-10-26 | Бёрингер Ингельхайм Интернациональ Гмбх | Гетероароматические соединения в качестве ингибиторов ванина |
| CA3156136A1 (en) * | 2019-11-07 | 2021-05-14 | Michael Hadd | Sodium-glucose linked transporter inhibitors for the management of chronic kidney disease, hypertension, and heart failure in companion animals |
| WO2022081716A1 (en) * | 2020-10-13 | 2022-04-21 | Accubit LLC - Biotechnology | Methods of treating iga nephropathy with thiol-containing molecules |
| US20240124479A1 (en) * | 2020-12-17 | 2024-04-18 | Shanghai Meiyue Biotech Development Co. Ltd | Pyrimidine carboxamide compound and use thereof |
| CN120247898A (zh) * | 2025-03-31 | 2025-07-04 | 大连医科大学附属第二医院 | 一种噻吩甲酰胺类化合物及其用途 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| HUP0104634A3 (en) | 1998-07-06 | 2002-11-28 | Bristol Myers Squibb Co | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| MY125533A (en) | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
| CN1642599A (zh) | 2002-02-27 | 2005-07-20 | 辉瑞产品公司 | Acc抑制剂 |
| PL1753748T3 (pl) | 2004-05-12 | 2010-01-29 | Pfizer Prod Inc | Pochodne proliny i ich zastosowanie jako inhibitorów peptydazy dipeptylowej IV |
| EP2010520B1 (en) | 2006-04-20 | 2012-09-12 | Pfizer Products Inc. | Heterobicyclic amides for the prevention and treatment of glucokinase-mediated diseases |
| WO2008063888A2 (en) * | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| BRPI0721053A2 (pt) | 2006-11-29 | 2014-07-29 | Pfizer Prod Inc | INIBIDORES DE ESPIROCETONA ACETIL-CoA CARBOXILASE |
| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| WO2009143018A2 (en) * | 2008-05-19 | 2009-11-26 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| JP5435592B2 (ja) | 2008-05-28 | 2014-03-05 | ファイザー・インク | ピラゾロスピロケトンアセチルＣｏＡカルボキシラーゼ阻害剤 |
| WO2009144555A1 (en) | 2008-05-28 | 2009-12-03 | Pfizer Inc. | Pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| JP2011529483A (ja) | 2008-07-29 | 2011-12-08 | ファイザー・インク | フッ素化ヘテロアリール |
| AU2009286380B2 (en) | 2008-08-28 | 2011-09-15 | Pfizer Inc. | Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives |
| TW201038580A (en) | 2009-02-02 | 2010-11-01 | Pfizer | 4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl derivatives |
| CA2754685A1 (en) | 2009-03-11 | 2010-09-16 | Pfizer Inc. | Substituted indazole amides |
| EP2604604A1 (en) | 2009-03-11 | 2013-06-19 | Pfizer Inc | Benzofuranyl derivatives used as glucokinase inhibitors |
| WO2010106457A2 (en) | 2009-03-20 | 2010-09-23 | Pfizer Inc. | 3-oxa-7-azabicyclo[3.3.1]nonanes |
| US20120052130A1 (en) | 2009-05-08 | 2012-03-01 | Pfizer Inc. | Gpr 119 modulators |
| CA2759843A1 (en) | 2009-05-08 | 2010-11-10 | Pfizer Inc. | Gpr 119 modulators |
| NZ596467A (en) | 2009-06-05 | 2014-01-31 | Pfizer | L- ( piperidin-4-yl) -pyrazole derivatives as gpr 119 modulators |
| WO2011005611A1 (en) | 2009-07-09 | 2011-01-13 | Merck Sharp & Dohme Corp. | Neuromedin u receptor agonists and uses thereof |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081331A1 (es) * | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| ES2653966T3 (es) * | 2010-04-27 | 2018-02-09 | Mitsubishi Tanabe Pharma Corporation | Nuevo derivado de amida y su uso como medicina |
| JP6113151B2 (ja) | 2011-05-17 | 2017-04-12 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節およびその適応症 |
| EP2736329A4 (en) | 2011-07-29 | 2015-03-25 | Tempero Pharmaceuticals Inc | COMPOUNDS AND METHODS |
| KR20160046693A (ko) | 2012-04-02 | 2016-04-29 | 싸이토키네틱스, 인코포레이티드 | 횡격막 기능을 향상시키는 방법들 |
| CA2885778A1 (en) | 2012-09-25 | 2014-04-03 | Mathilde Muzerelle | Alpha hydroxy amides |
-
2016
- 2016-05-16 US US15/574,625 patent/US10308615B2/en active Active
- 2016-05-16 WO PCT/IB2016/052825 patent/WO2016193844A1/en not_active Ceased
- 2016-05-16 CA CA2987179A patent/CA2987179C/en not_active Expired - Fee Related
- 2016-05-16 EP EP16724127.2A patent/EP3303303A1/en not_active Withdrawn
- 2016-05-16 JP JP2017561653A patent/JP2018516254A/ja active Pending
-
2019
- 2019-04-10 US US16/380,256 patent/US20190292157A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018516254A5 (https=) | ||
| HRP20220096T1 (hr) | Inhibitori lizin specifične demetilaze-1 | |
| RU2008141509A (ru) | Mglur5 модуляторы 1 | |
| JP2010513304A5 (https=) | ||
| JP2014531465A5 (https=) | ||
| HRP20110939T1 (hr) | Supstituirani benzimidazoli kao inhibitori kinaze | |
| RU2482111C2 (ru) | Соединения, обладающие противораковой активностью | |
| RU2009125620A (ru) | Органические соединения | |
| JP2009519967A5 (https=) | ||
| ME00427B (me) | N-supstituisani hidroksipiramidinon karboksamidni inhibitori hiv integraze | |
| RU2010110640A (ru) | Соединения и композиции 5-(4-(галогеналкокси)фенил)пиримидин-2-амина в качестве ингибиторов киназ | |
| HRP20180546T1 (hr) | Supstituirani benzilindazoli za uporabu kao inhibitori bub1 kinaze za liječenje hiperproliferativnih bolesti | |
| JP2005516934A5 (https=) | ||
| JP2019524705A5 (https=) | ||
| RU2014153626A (ru) | Пиридиноновые и пиридазиноновые производные | |
| JP2016519096A5 (https=) | ||
| JP2020526547A5 (https=) | ||
| HRP20141190T1 (hr) | Disupstituirani derivati piridina kao antikancerogena sredstva | |
| RU2015143517A (ru) | Пиразолсодержащие соединения и их применения | |
| JP2008507564A5 (https=) | ||
| JP2013527173A5 (https=) | ||
| JP2008525502A5 (https=) | ||
| AR064302A1 (es) | Arilpirazoles sustitudos | |
| HRP20140593T1 (hr) | Derivati 1,3-disupstituiranih imidazolidin-2-ona kao cyp 17-inhibitori | |
| RU2010125220A (ru) | Ненуклеозидные ингибиторы обратной транскриптазы |