ES2831322T3 - Compuestos de 2-oxo-1,2-dihidropiridin-3,5-dicarboxamida como inhibidores de bromodominios - Google Patents
Compuestos de 2-oxo-1,2-dihidropiridin-3,5-dicarboxamida como inhibidores de bromodominios Download PDFInfo
- Publication number
- ES2831322T3 ES2831322T3 ES16778310T ES16778310T ES2831322T3 ES 2831322 T3 ES2831322 T3 ES 2831322T3 ES 16778310 T ES16778310 T ES 16778310T ES 16778310 T ES16778310 T ES 16778310T ES 2831322 T3 ES2831322 T3 ES 2831322T3
- Authority
- ES
- Spain
- Prior art keywords
- oxo
- methyl
- dihydropyridine
- dicarboxamide
- benzyl
- 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.)
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- 102000001805 Bromodomains Human genes 0.000 title description 44
- 108050009021 Bromodomains Proteins 0.000 title description 43
- 239000003112 inhibitor Substances 0.000 title description 22
- CTZIPFCPXSEUIP-UHFFFAOYSA-N 2-oxo-1H-pyridine-3,5-dicarboxamide Chemical class O=C1NC=C(C=C1C(=O)N)C(=O)N CTZIPFCPXSEUIP-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 221
- 150000003839 salts Chemical class 0.000 claims abstract description 157
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 79
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
- -1 -OCHF2 Chemical group 0.000 claims abstract description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Chemical group 0.000 claims abstract description 9
- 239000011593 sulfur Chemical group 0.000 claims abstract description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 5
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 42
- 238000011282 treatment Methods 0.000 claims description 37
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 29
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 23
- 230000001154 acute effect Effects 0.000 claims description 20
- 230000001363 autoimmune Effects 0.000 claims description 13
- 230000001684 chronic effect Effects 0.000 claims description 13
- QEXKCLKKZYLBQP-UHFFFAOYSA-N CCCNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC Chemical compound CCCNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC QEXKCLKKZYLBQP-UHFFFAOYSA-N 0.000 claims description 8
- IJHWQSXLORJLJY-UHFFFAOYSA-N CNC(=O)C1=CC(=CN(CC2=CC(C)=CC=C2)C1=O)C(=O)NCCC1=CNN=C1 Chemical compound CNC(=O)C1=CC(=CN(CC2=CC(C)=CC=C2)C1=O)C(=O)NCCC1=CNN=C1 IJHWQSXLORJLJY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- UQWYBQVXLSDHKF-UHFFFAOYSA-N 5-N-ethyl-1-[[3-(2-hydroxyethoxy)phenyl]methyl]-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CCNC(=O)C1=CN(CC2=CC(OCCO)=CC=C2)C(=O)C(=C1)C(=O)NC UQWYBQVXLSDHKF-UHFFFAOYSA-N 0.000 claims description 6
- VTJNNPHFQQYQSQ-UHFFFAOYSA-N 1-benzyl-5-N-butyl-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CCCCNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC VTJNNPHFQQYQSQ-UHFFFAOYSA-N 0.000 claims description 5
- QGDKBYNQYCEMIC-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-(2-pyridin-2-ylethyl)pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=NC=CC=C1 QGDKBYNQYCEMIC-UHFFFAOYSA-N 0.000 claims description 4
- MFSZAVZIJWFJFW-UHFFFAOYSA-N 5-N-ethyl-3-N-methyl-1-[(3-methylphenyl)methyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CCNC(=O)C1=CN(CC2=CC(C)=CC=C2)C(=O)C(=C1)C(=O)NC MFSZAVZIJWFJFW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
- REMQVVQBQSAYFB-UHFFFAOYSA-N CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CN=CN1 Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CN=CN1 REMQVVQBQSAYFB-UHFFFAOYSA-N 0.000 claims description 4
- WDDWXBIKJCMWSY-UHFFFAOYSA-N CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCCC1=NC=CN1 Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCCC1=NC=CN1 WDDWXBIKJCMWSY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- SXANHRXGPZULMS-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-(3,3,3-trifluoropropyl)pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC(F)(F)F SXANHRXGPZULMS-UHFFFAOYSA-N 0.000 claims description 3
- SQUQXKBBDZDFFU-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-[2-(1H-pyrazol-4-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)c1cc(cn(Cc2ccccc2)c1=O)C(=O)NCCc1cn[nH]c1 SQUQXKBBDZDFFU-UHFFFAOYSA-N 0.000 claims description 3
- JEQGAHKBIFRHMQ-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-(3-methylbutyl)-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC(C)C JEQGAHKBIFRHMQ-UHFFFAOYSA-N 0.000 claims description 3
- MQKOZRUIYLFGEB-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-[4-(methylamino)-4-oxobutyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)CCCNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC MQKOZRUIYLFGEB-UHFFFAOYSA-N 0.000 claims description 3
- XFWIXXZNFMSKTP-UHFFFAOYSA-N 1-benzyl-5-N-ethyl-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CCNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC XFWIXXZNFMSKTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- FWZRBPUVQUGTAC-UHFFFAOYSA-N 1-(1H-indol-4-ylmethyl)-3-N-methyl-2-oxo-5-N-[2-(1H-pyrazol-4-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)c1cc(cn(Cc2cccc3[nH]ccc23)c1=O)C(=O)NCCc1cn[nH]c1 FWZRBPUVQUGTAC-UHFFFAOYSA-N 0.000 claims description 2
- DUWSWYMITSIPFJ-UHFFFAOYSA-N 1-[(2-fluoro-3-methylphenyl)methyl]-3-N-methyl-2-oxo-5-N-[2-(1H-pyrazol-4-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=C(F)C(C)=CC=C2)C1=O)C(=O)NCCC1=CNN=C1 DUWSWYMITSIPFJ-UHFFFAOYSA-N 0.000 claims description 2
- LULWCVIDODKXLB-UHFFFAOYSA-N 1-[(2-fluoro-3-methylphenyl)methyl]-5-N-[2-(1H-imidazol-5-yl)ethyl]-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=C(F)C(C)=CC=C2)C1=O)C(=O)NCCC1=CNC=N1 LULWCVIDODKXLB-UHFFFAOYSA-N 0.000 claims description 2
- YRHZKYRURGBODZ-UHFFFAOYSA-N 1-[(3-cyanophenyl)methyl]-3-N,5-N-dimethyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CN(CC2=CC(=CC=C2)C#N)C(=O)C(=C1)C(=O)NC YRHZKYRURGBODZ-UHFFFAOYSA-N 0.000 claims description 2
- ZGVHEXSCYYPCJW-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-3-N-methyl-2-oxo-5-N-[2-(1H-pyrazol-4-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC(OC)=CC=C2)C1=O)C(=O)NCCC1=CNN=C1 ZGVHEXSCYYPCJW-UHFFFAOYSA-N 0.000 claims description 2
- VVYUMAQGZVLGMK-UHFFFAOYSA-N 1-[[3-(2-hydroxyethoxy)phenyl]methyl]-3-N-methyl-2-oxo-5-N-[2-(1H-pyrazol-4-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC(OCCO)=CC=C2)C1=O)C(=O)NCCC1=CNN=C1 VVYUMAQGZVLGMK-UHFFFAOYSA-N 0.000 claims description 2
- ZUHGYWQWGMWHPJ-UHFFFAOYSA-N 1-[[3-(2-hydroxyethoxy)phenyl]methyl]-5-N-[2-(1H-imidazol-5-yl)ethyl]-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC(OCCO)=CC=C2)C1=O)C(=O)NCCC1=CNC=N1 ZUHGYWQWGMWHPJ-UHFFFAOYSA-N 0.000 claims description 2
- DANLNXYNIAMHCE-UHFFFAOYSA-N 1-benzyl-3-N,5-N-dimethyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC DANLNXYNIAMHCE-UHFFFAOYSA-N 0.000 claims description 2
- REGZAFBKNVQTID-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-(2-pyridin-3-ylethyl)pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CC=CN=C1 REGZAFBKNVQTID-UHFFFAOYSA-N 0.000 claims description 2
- UFIXPEWDAIVQGG-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-(2-pyridin-4-ylethyl)pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CC=NC=C1 UFIXPEWDAIVQGG-UHFFFAOYSA-N 0.000 claims description 2
- LXCKAASCJJIWBC-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-[2-(1,3-thiazol-4-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CSC=N1 LXCKAASCJJIWBC-UHFFFAOYSA-N 0.000 claims description 2
- QKNHGOMHDHQWQZ-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-[2-(1H-pyrazol-5-yl)ethyl]pyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CC=NN1 QKNHGOMHDHQWQZ-UHFFFAOYSA-N 0.000 claims description 2
- AHAQFZBVHBOHFW-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-propan-2-ylpyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NC(C)C AHAQFZBVHBOHFW-UHFFFAOYSA-N 0.000 claims description 2
- FYNTXIKCFMTBOR-UHFFFAOYSA-N 1-benzyl-3-N-methyl-2-oxo-5-N-pyridazin-4-ylpyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NC1=CN=NC=C1 FYNTXIKCFMTBOR-UHFFFAOYSA-N 0.000 claims description 2
- RIMDTGWDSDEJGW-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-(2-methylpropyl)-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCC(C)C RIMDTGWDSDEJGW-UHFFFAOYSA-N 0.000 claims description 2
- JVHVTBGUMLAESI-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-(2-methylsulfonylethyl)-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCS(C)(=O)=O JVHVTBGUMLAESI-UHFFFAOYSA-N 0.000 claims description 2
- FWQIQTSLUWALKI-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-(3-methylsulfonylpropyl)-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCCS(C)(=O)=O FWQIQTSLUWALKI-UHFFFAOYSA-N 0.000 claims description 2
- GDIQCISRJSUFQR-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-[2-(1,2-oxazol-4-yl)ethyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC1=CON=C1 GDIQCISRJSUFQR-UHFFFAOYSA-N 0.000 claims description 2
- GPPNORSDYVXVGS-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-[2-(1-methylpyrazol-4-yl)ethyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)c1cc(cn(Cc2ccccc2)c1=O)C(=O)NCCc1cnn(C)c1 GPPNORSDYVXVGS-UHFFFAOYSA-N 0.000 claims description 2
- XSUFXEMEOBUCEQ-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-[2-(4-methyl-1,2,4-triazol-3-yl)ethyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)c1cc(cn(Cc2ccccc2)c1=O)C(=O)NCCc1nncn1C XSUFXEMEOBUCEQ-UHFFFAOYSA-N 0.000 claims description 2
- GHQMXKIALCCWIQ-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)c1cc(cn(Cc2ccccc2)c1=O)C(=O)NCCc1scnc1C GHQMXKIALCCWIQ-UHFFFAOYSA-N 0.000 claims description 2
- PKSWJRINFNVFHE-UHFFFAOYSA-N 1-benzyl-3-N-methyl-5-N-[3-(methylamino)-3-oxopropyl]-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)CCNC(=O)C1=CN(CC2=CC=CC=C2)C(=O)C(=C1)C(=O)NC PKSWJRINFNVFHE-UHFFFAOYSA-N 0.000 claims description 2
- CRWAKZZBHIGVID-UHFFFAOYSA-N 1-benzyl-5-N-(2-cyanoethyl)-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCC#N CRWAKZZBHIGVID-UHFFFAOYSA-N 0.000 claims description 2
- CCJIIOFOFBMUCK-UHFFFAOYSA-N 1-benzyl-5-N-(2-hydroxyethyl)-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCO CCJIIOFOFBMUCK-UHFFFAOYSA-N 0.000 claims description 2
- LTDMXYJCXCTKLZ-UHFFFAOYSA-N 1-benzyl-5-N-(2-methoxyethyl)-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCOC LTDMXYJCXCTKLZ-UHFFFAOYSA-N 0.000 claims description 2
- MVEWQBUZCZGKRP-UHFFFAOYSA-N 1-benzyl-5-N-(2-methoxypropyl)-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCC(C)OC MVEWQBUZCZGKRP-UHFFFAOYSA-N 0.000 claims description 2
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- KODXULLKFXZKHH-UHFFFAOYSA-N 1-benzyl-5-N-[3-(dimethylamino)propyl]-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCCN(C)C KODXULLKFXZKHH-UHFFFAOYSA-N 0.000 claims description 2
- FMACSLBHAZPXFU-UHFFFAOYSA-N 5-N-(3-aminopropyl)-1-benzyl-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=CC=CC=C2)C1=O)C(=O)NCCCN FMACSLBHAZPXFU-UHFFFAOYSA-N 0.000 claims description 2
- XIFYHEHHBPJHCX-UHFFFAOYSA-N 5-N-[2-(1H-imidazol-5-yl)ethyl]-1-(1H-indol-4-ylmethyl)-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CNC(=O)C1=CC(=CN(CC2=C3C=CNC3=CC=C2)C1=O)C(=O)NCCC1=CNC=N1 XIFYHEHHBPJHCX-UHFFFAOYSA-N 0.000 claims description 2
- KSAAVHPPBIBSDJ-UHFFFAOYSA-N 5-N-ethyl-1-(1H-indol-4-ylmethyl)-3-N-methyl-2-oxopyridine-3,5-dicarboxamide Chemical compound CCNC(=O)c1cc(C(=O)NC)c(=O)n(Cc2cccc3[nH]ccc23)c1 KSAAVHPPBIBSDJ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562237002P | 2015-10-05 | 2015-10-05 | |
| PCT/EP2016/073532 WO2017060180A1 (en) | 2015-10-05 | 2016-10-03 | 2-oxo-1,2-dihydropyridine-3,5-dicarboxamide compounds as bromodomain inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2831322T3 true ES2831322T3 (es) | 2021-06-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16778310T Active ES2831322T3 (es) | 2015-10-05 | 2016-10-03 | Compuestos de 2-oxo-1,2-dihidropiridin-3,5-dicarboxamida como inhibidores de bromodominios |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10471050B2 (enExample) |
| EP (1) | EP3359531B1 (enExample) |
| JP (1) | JP6832923B2 (enExample) |
| KR (1) | KR20180059551A (enExample) |
| CN (1) | CN108290866B (enExample) |
| AU (1) | AU2016334637A1 (enExample) |
| BR (1) | BR112018006545A2 (enExample) |
| CA (1) | CA2999379A1 (enExample) |
| ES (1) | ES2831322T3 (enExample) |
| RU (1) | RU2018114705A (enExample) |
| WO (1) | WO2017060180A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2016315360B2 (en) | 2015-09-02 | 2019-09-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Pyridinone dicarboxamide for use as bromodomain inhibitors |
| US10370356B2 (en) | 2015-09-22 | 2019-08-06 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pyridinone dicarboxamide for use as bromodomain inhibitors |
| RU2018114705A (ru) | 2015-10-05 | 2019-11-07 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Соединения 2-оксо-1,2-дигидропиридин-3,5-дикарбоксамида в качестве ингибиторов бромодомена |
| ES2840848T3 (es) | 2016-04-07 | 2021-07-07 | Glaxosmithkline Ip No 2 Ltd | Derivados de piridilo como inhibidores de bromodominio |
| BR112018073524A2 (pt) * | 2016-05-24 | 2019-05-28 | Glaxosmithkline Ip No 2 Ltd | composto, composição farmacêutica, combinação, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, método de tratamento de uma doença ou condição. |
| GB201703282D0 (en) * | 2017-03-01 | 2017-04-12 | Glaxosmithkline Intellectual Property (No 2) Ltd | Compounds |
| JOP20190192A1 (ar) | 2017-03-01 | 2019-08-08 | Glaxosmithkline Ip No 2 Ltd | مشتقات بيرازول بوصفها مثبطات برومودومين |
| GB201814167D0 (en) | 2018-08-31 | 2018-10-17 | Glaxosmithkline Ip No 2 Ltd | Compounds |
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| BR0116539A (pt) | 2000-12-28 | 2003-09-23 | Shionogi & Co | Derivados de piridona tendo uma atividade de ligação para o receptor 2 do tipo canabinóide |
| US20050101590A1 (en) * | 2002-02-19 | 2005-05-12 | Kiyoshi Yasui | Antipruritics |
| WO2004033446A1 (en) | 2002-10-09 | 2004-04-22 | Danter Wayne R | Protein tyrosine kinase inhibitors |
| EP1433788A1 (en) | 2002-12-23 | 2004-06-30 | Aventis Pharma Deutschland GmbH | Pyrazole-derivatives as factor Xa inhibitors |
| GB0919434D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| PE20150953A1 (es) | 2012-11-08 | 2015-06-20 | Bristol Myers Squibb Co | Compuestos de piridilo sustituidos con heteroarilo utiles como moduladores de cinasa |
| CA2895905A1 (en) | 2012-12-21 | 2014-06-26 | Zenith Epigenetics Corp. | Novel heterocyclic compounds as bromodomain inhibitors |
| EP3027604B1 (en) | 2013-07-31 | 2019-02-20 | Zenith Epigenetics Ltd. | Novel quinazolinones as bromodomain inhibitors |
| AU2016315360B2 (en) | 2015-09-02 | 2019-09-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Pyridinone dicarboxamide for use as bromodomain inhibitors |
| RU2018114705A (ru) | 2015-10-05 | 2019-11-07 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Соединения 2-оксо-1,2-дигидропиридин-3,5-дикарбоксамида в качестве ингибиторов бромодомена |
| ES2840848T3 (es) | 2016-04-07 | 2021-07-07 | Glaxosmithkline Ip No 2 Ltd | Derivados de piridilo como inhibidores de bromodominio |
| BR112018073524A2 (pt) | 2016-05-24 | 2019-05-28 | Glaxosmithkline Ip No 2 Ltd | composto, composição farmacêutica, combinação, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, método de tratamento de uma doença ou condição. |
-
2016
- 2016-10-03 RU RU2018114705A patent/RU2018114705A/ru not_active Application Discontinuation
- 2016-10-03 KR KR1020187012923A patent/KR20180059551A/ko not_active Withdrawn
- 2016-10-03 JP JP2018517320A patent/JP6832923B2/ja not_active Expired - Fee Related
- 2016-10-03 CA CA2999379A patent/CA2999379A1/en not_active Abandoned
- 2016-10-03 AU AU2016334637A patent/AU2016334637A1/en not_active Abandoned
- 2016-10-03 BR BR112018006545A patent/BR112018006545A2/pt active Search and Examination
- 2016-10-03 US US15/766,222 patent/US10471050B2/en not_active Expired - Fee Related
- 2016-10-03 WO PCT/EP2016/073532 patent/WO2017060180A1/en not_active Ceased
- 2016-10-03 CN CN201680071214.5A patent/CN108290866B/zh not_active Expired - Fee Related
- 2016-10-03 EP EP16778310.9A patent/EP3359531B1/en active Active
- 2016-10-03 ES ES16778310T patent/ES2831322T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180059551A (ko) | 2018-06-04 |
| AU2016334637A1 (en) | 2018-04-12 |
| JP2018529737A (ja) | 2018-10-11 |
| US20180280368A1 (en) | 2018-10-04 |
| US10471050B2 (en) | 2019-11-12 |
| CA2999379A1 (en) | 2017-04-13 |
| CN108290866A (zh) | 2018-07-17 |
| BR112018006545A2 (pt) | 2018-10-16 |
| EP3359531A1 (en) | 2018-08-15 |
| WO2017060180A1 (en) | 2017-04-13 |
| EP3359531B1 (en) | 2020-08-19 |
| CN108290866B (zh) | 2020-12-18 |
| RU2018114705A (ru) | 2019-11-07 |
| JP6832923B2 (ja) | 2021-02-24 |
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