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 |
|---|---|---|---|---|
| EP3484876A1 (en) * | 2016-07-14 | 2019-05-22 | 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 |
| KR101798840B1 (ko) | 2017-05-17 | 2017-11-17 | 주식회사 레고켐 바이오사이언스 | 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물 |
| US10961242B2 (en) | 2017-05-17 | 2021-03-30 | Legochem Biosciences, Inc. | Compounds as autotaxin inhibitors and pharmaceutical compositions comprising the same |
| WO2018228934A1 (en) * | 2017-06-12 | 2018-12-20 | 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 |
| US10702488B2 (en) * | 2017-12-19 | 2020-07-07 | Theriac Biomedical Inc. | PPAR-γ activators, HDAC inhibitors and their therapeutical usages |
| US11497723B1 (en) * | 2017-12-19 | 2022-11-15 | Tony Antakly | PPAR-gamma activators, HDAC inhibitors and their therapeutical usages |
| WO2019133445A1 (en) * | 2017-12-28 | 2019-07-04 | Inception Ibd, Inc. | Aminothiazoles as inhibitors of vanin-1 |
| ES2932557T3 (es) | 2018-08-28 | 2023-01-20 | Boehringer Ingelheim Int | Compuestos heteroaromáticos como inhibidores de vanina |
| WO2020102575A1 (en) * | 2018-11-16 | 2020-05-22 | Inception Ibd, Inc. | Heterocyclic aminothiazoles and uses thereof |
| KR20210099092A (ko) | 2018-12-03 | 2021-08-11 | 베링거 인겔하임 인터내셔날 게엠베하 | 바닌 억제제로서의 헤테로방향족 화합물 |
| TWI838430B (zh) * | 2018-12-03 | 2024-04-11 | 德商百靈佳殷格翰國際股份有限公司 | 作為vanin抑制劑之雜芳族化合物 |
| HUE070992T2 (hu) * | 2018-12-03 | 2025-07-28 | Boehringer Ingelheim Int | Heteroaromás vegyületek mint vanin gátlók |
| WO2021092341A1 (en) * | 2019-11-07 | 2021-05-14 | Increvet, Inc. | 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 |
| WO2022127909A1 (zh) * | 2020-12-17 | 2022-06-23 | 上海美悦生物科技发展有限公司 | 一种嘧啶甲酰胺类化合物及其应用 |
| 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 |
| WO2000001389A1 (en) | 1998-07-06 | 2000-01-13 | 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 |
| NZ534582A (en) | 2002-02-27 | 2006-03-31 | Pfizer Prod Inc | ACC inhibitors |
| KR100869616B1 (ko) | 2004-05-12 | 2008-11-21 | 화이자 프로덕츠 인코포레이티드 | 프롤린 유도체 및 그의 다이펩티딜 펩티다제－ｉｖ저해제로서의 용도 |
| JP5190448B2 (ja) | 2006-04-20 | 2013-04-24 | ファイザー・プロダクツ・インク | グルコキナーゼ仲介疾患を予防および治療するための縮合フェニルアミド複素環化合物 |
| WO2008063888A2 (en) * | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| EA200900613A1 (ru) | 2006-11-29 | 2009-10-30 | Пфайзер Продактс Инк. | Спирокетоновые ингибиторы ацетил-коа-карбоксилаз |
| 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 |
| US20110009443A1 (en) | 2008-05-28 | 2011-01-13 | Kevin Daniel Freeman-Cook | Pyrazolospiroketone Acetyl-Coa Carboxylase Inhibitors |
| WO2009144554A1 (en) | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Pyrazolospiroketone acetyl-c0a carboxylase inhibitors |
| EP2318370A1 (en) | 2008-07-29 | 2011-05-11 | Pfizer Inc. | Fluorinated heteroaryls |
| MY155418A (en) | 2008-08-28 | 2015-10-15 | Pfizer | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
| WO2010086820A1 (en) | 2009-02-02 | 2010-08-05 | Pfizer Inc. | 4-amino-5-oxo-7, 8-dihydropyrimido [5,4-f] [1,4] oxazepin-6 (5h) -yl) phenyl derivatives, pharmaceutical compositions and uses thereof |
| US20110319379A1 (en) | 2009-03-11 | 2011-12-29 | Corbett Jeffrey W | Substituted Indazole Amides And Their Use As Glucokinase Activators |
| MY151246A (en) | 2009-03-11 | 2014-04-30 | Pfizer | Benzofuranyl derivatives |
| WO2010106457A2 (en) | 2009-03-20 | 2010-09-23 | Pfizer Inc. | 3-oxa-7-azabicyclo[3.3.1]nonanes |
| CA2759843A1 (en) | 2009-05-08 | 2010-11-10 | Pfizer Inc. | Gpr 119 modulators |
| WO2010128414A1 (en) | 2009-05-08 | 2010-11-11 | 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 |
| TWI525090B (zh) | 2010-04-27 | 2016-03-11 | Mitsubishi Tanabe Pharma Corp | Novel amide derivatives and their use as pharmaceuticals |
| AU2012255275B2 (en) | 2011-05-17 | 2016-01-28 | Plexxikon Inc. | Kinase modulation and indications therefor |
| US20140155419A1 (en) | 2011-07-29 | 2014-06-05 | Erkan Baloglu | Compounds and methods |
| SG10201701101YA (en) | 2012-04-02 | 2017-04-27 | Cytokinetics Inc | Methods for improving diaphragm function |
| EP2900633A1 (en) | 2012-09-25 | 2015-08-05 | Merck Patent GmbH | Alpha hydroxy amides |
-
2016
- 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 JP JP2017561653A patent/JP2018516254A/ja active Pending
- 2016-05-16 EP EP16724127.2A patent/EP3303303A1/en not_active Withdrawn
- 2016-05-16 US US15/574,625 patent/US10308615B2/en active Active
-
2019
- 2019-04-10 US US16/380,256 patent/US20190292157A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018516254A5 (https=) | ||
| RU2008141509A (ru) | Mglur5 модуляторы 1 | |
| JP2010513304A5 (https=) | ||
| JP2014531465A5 (https=) | ||
| 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 | |
| JP2020526547A5 (https=) | ||
| HRP20141190T1 (hr) | Disupstituirani derivati piridina kao antikancerogena sredstva | |
| RU2015143517A (ru) | Пиразолсодержащие соединения и их применения | |
| JP2008507564A5 (https=) | ||
| JP2013527173A5 (https=) | ||
| JP2008525502A5 (https=) | ||
| JP2018535999A5 (https=) | ||
| AR064302A1 (es) | Arilpirazoles sustitudos | |
| HRP20140593T1 (hr) | Derivati 1,3-disupstituiranih imidazolidin-2-ona kao cyp 17-inhibitori | |
| RU2010125220A (ru) | Ненуклеозидные ингибиторы обратной транскриптазы | |
| JP2013528591A5 (https=) | ||
| HRP20200098T1 (hr) | Spirociklični spojevi kao inhibitori triptofan hidroksilaze |