RU2655727C9 - Фуропиридины в качестве ингибиторов бромодоменов - Google Patents

Info

Publication number

RU2655727C9

RU2655727C9 RU2015137103A RU2015137103A RU2655727C9 RU 2655727 C9 RU2655727 C9 RU 2655727C9 RU 2015137103 A RU2015137103 A RU 2015137103A RU 2015137103 A RU2015137103 A RU 2015137103A RU 2655727 C9 RU2655727 C9 RU 2655727C9

Authority

RU

Russia

Prior art keywords

methyl

pyridin

methylsulfonyl

piperazin

furo

Prior art date

2013-03-14

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• 102000001805 Bromodomains Human genes 0.000 title claims description 23
• 108050009021 Bromodomains Proteins 0.000 title claims description 23
• 239000003112 inhibitor Substances 0.000 title claims description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 224
• -1 -CH2NH2 Chemical group 0.000 claims abstract description 174
• 238000000034 method Methods 0.000 claims abstract description 153
• 150000003839 salts Chemical class 0.000 claims abstract description 110
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 106
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 57
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 48
• 238000011282 treatment Methods 0.000 claims abstract description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
• 201000010099 disease Diseases 0.000 claims abstract description 29
• 238000004519 manufacturing process Methods 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
• 239000003814 drug Substances 0.000 claims abstract description 26
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
• 150000002367 halogens Chemical class 0.000 claims abstract description 22
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 21
• 229910052720 vanadium Inorganic materials 0.000 claims abstract description 21
• 229940125763 bromodomain inhibitor Drugs 0.000 claims abstract description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
• 125000001424 substituent group Chemical group 0.000 claims abstract description 7
• 230000000694 effects Effects 0.000 claims abstract description 6
• 239000001301 oxygen Substances 0.000 claims abstract description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 125000002947 alkylene group Chemical group 0.000 claims description 33
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
• FYNCIYHECMWXPK-UHFFFAOYSA-N 5h-furo[3,2-c]pyridin-4-one Chemical compound O=C1NC=CC2=C1C=CO2 FYNCIYHECMWXPK-UHFFFAOYSA-N 0.000 claims description 21
• MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical compound O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• ZEXMGFHHBCQZFB-TZHYSIJRSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxetan-2-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3OCC3)=O)=C2O1 ZEXMGFHHBCQZFB-TZHYSIJRSA-N 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 5
• VVULLKQYMRSJHE-UHFFFAOYSA-N 2-(1,4-diazepan-1-ylmethyl)-7-(3,4-dimethoxyphenyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCNCCC1)=C2 VVULLKQYMRSJHE-UHFFFAOYSA-N 0.000 claims description 4
• ZGSSEXLPGQBKLO-UHFFFAOYSA-N 2-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCS(=O)(=O)CC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 ZGSSEXLPGQBKLO-UHFFFAOYSA-N 0.000 claims description 4
• VJSUIISNWBLXEU-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[2-(1-phenylethylamino)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C=1C=CC=CC=1C(C)NC(N=CC=1)=CC=1C(C=1O2)=CN(C)C(=O)C=1C=C2CN1CCN(S(C)(=O)=O)CC1 VJSUIISNWBLXEU-UHFFFAOYSA-N 0.000 claims description 4
• FZCIRGODGLUISW-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[5-(1-phenylethoxy)pyridin-3-yl]furo[3,2-c]pyridin-4-one Chemical compound C=1C=CC=CC=1C(C)OC(C=1)=CN=CC=1C(C=1O2)=CN(C)C(=O)C=1C=C2CN1CCN(S(C)(=O)=O)CC1 FZCIRGODGLUISW-UHFFFAOYSA-N 0.000 claims description 4
• JBFGXWICIPTWHK-GOSISDBHSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[2-[2-(2-oxopyrrolidin-1-yl)ethoxy]pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCCN4C(CCC4)=O)N=CC=3)=O)=C2O1 JBFGXWICIPTWHK-GOSISDBHSA-N 0.000 claims description 4
• UVHOTKWPYIGJOA-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-(morpholin-4-ylmethyl)furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCOCC1)=C2 UVHOTKWPYIGJOA-UHFFFAOYSA-N 0.000 claims description 4
• GAJMGOCHIMRYAH-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-(piperidin-1-ylmethyl)furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCCCC1)=C2 GAJMGOCHIMRYAH-UHFFFAOYSA-N 0.000 claims description 4
• SBTNGPOTCXTYMB-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[(3-methylmorpholin-4-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1C(COCC1)C)=C2 SBTNGPOTCXTYMB-UHFFFAOYSA-N 0.000 claims description 4
• SVUMANNVOCNDAY-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[2,3-d]pyridazin-4-one Chemical compound COC=1C=C(C=CC1OC)C1=NN(C(C2=C1OC(=C2)CN2CCN(CC2)S(=O)(=O)C)=O)C SVUMANNVOCNDAY-UHFFFAOYSA-N 0.000 claims description 4
• NQSYBFFTCCDUGQ-OAHLLOKOSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 NQSYBFFTCCDUGQ-OAHLLOKOSA-N 0.000 claims description 4
• QETXRIOCXCNBFV-MRXNPFEDSA-N 7-[2-(cyclopropylmethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCC4CC4)N=CC=3)=O)=C2O1 QETXRIOCXCNBFV-MRXNPFEDSA-N 0.000 claims description 4
• PQMREPVBNKVBFM-MRXNPFEDSA-N 7-[3-(cyclopropylmethoxy)pyridin-4-yl]-5-methyl-2-[[(2R)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C1(CC1)COC=1C=NC=CC1C=1C2=C(C(N(C1)C)=O)C=C(O2)CN2[C@@H](CN(CC2)S(=O)(=O)C)C PQMREPVBNKVBFM-MRXNPFEDSA-N 0.000 claims description 4
• ZRIWCCGYWSMJPP-UHFFFAOYSA-N 7-[3-(cyclopropylmethylamino)pyridin-4-yl]-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C1=CC=NC=C1NCC1CC1 ZRIWCCGYWSMJPP-UHFFFAOYSA-N 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• ASSGIDPIKQABBH-OAHLLOKOSA-N N-methyl-N-[4-[5-methyl-2-[[(2R)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN(C(C)=O)C1=NC=CC(=C1)C=1C2=C(C(N(C1)C)=O)C=C(O2)CN2[C@@H](CN(CC2)S(=O)(=O)C)C ASSGIDPIKQABBH-OAHLLOKOSA-N 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• QQTMSFFWDWGMFQ-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCN(CC4)S(C)(=O)=O)=CC=3C(=O)N(C)C=2)=C1 QQTMSFFWDWGMFQ-UHFFFAOYSA-N 0.000 claims description 4
• MCTBSAVNHXJNFR-CQSZACIVSA-N n-[4-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 MCTBSAVNHXJNFR-CQSZACIVSA-N 0.000 claims description 4
• XGAYYTTXMZNIOV-OAHLLOKOSA-N n-[4-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]cyclopropanecarboxamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(=O)C4CC4)N=CC=3)=O)=C2O1 XGAYYTTXMZNIOV-OAHLLOKOSA-N 0.000 claims description 4
• GCELDXCALWQMOW-OAHLLOKOSA-N n-[4-[5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)CC)=CC(C=2C=3OC(CN4[C@@H](CN(CC4)S(C)(=O)=O)C)=CC=3C(=O)N(C)C=2)=C1 GCELDXCALWQMOW-OAHLLOKOSA-N 0.000 claims description 4
• XZBPCZMBXNAIQV-UHFFFAOYSA-N 2-[(3,3-difluoropiperidin-1-yl)methyl]-5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CC(F)(F)CCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 XZBPCZMBXNAIQV-UHFFFAOYSA-N 0.000 claims description 3
• LJYRYWKCKYKAET-GOSISDBHSA-N 5-methyl-2-[(1r)-1-(4-methylsulfonylpiperazin-1-yl)ethyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound N1([C@H](C)C=2OC3=C(C(N(C)C=C3C=3C=C(OCC4CCOCC4)N=CC=3)=O)C=2)CCN(S(C)(=O)=O)CC1 LJYRYWKCKYKAET-GOSISDBHSA-N 0.000 claims description 3
• YYLOVEDYTPNZLM-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-(3-phenylmethoxyphenyl)furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 YYLOVEDYTPNZLM-UHFFFAOYSA-N 0.000 claims description 3
• LXQMPGUFEUSBHM-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[2,3-d]pyridazin-4-one Chemical compound CN1N=C(C2=C(C1=O)C=C(O2)CN2CCN(CC2)S(=O)(=O)C)C2=CC(=NC=C2)OCC2CCOCC2 LXQMPGUFEUSBHM-UHFFFAOYSA-N 0.000 claims description 3
• ORGIADDXKMFHEG-UHFFFAOYSA-N 5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 ORGIADDXKMFHEG-UHFFFAOYSA-N 0.000 claims description 3
• LJYRYWKCKYKAET-UHFFFAOYSA-N 5-methyl-2-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C=1C(C(N(C)C=C2C=3C=C(OCC4CCOCC4)N=CC=3)=O)=C2OC=1C(C)N1CCN(S(C)(=O)=O)CC1 LJYRYWKCKYKAET-UHFFFAOYSA-N 0.000 claims description 3
• CZTJIXVUZMIAJF-LJQANCHMSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[2-(2-pyrrolidin-1-ylethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCCN4CCCC4)N=CC=3)=O)=C2O1 CZTJIXVUZMIAJF-LJQANCHMSA-N 0.000 claims description 3
• LDNCGMMSYNRWBO-MRXNPFEDSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxetan-3-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3COC3)=O)=C2O1 LDNCGMMSYNRWBO-MRXNPFEDSA-N 0.000 claims description 3
• UGUGLNIFVYATCV-UHFFFAOYSA-N 5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]-2-(1,4-oxazepan-4-ylmethyl)furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCOCCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1OCC1CCOCC1 UGUGLNIFVYATCV-UHFFFAOYSA-N 0.000 claims description 3
• KIWPYLUFZAGLGZ-MRXNPFEDSA-N 7-[2-(2-methoxyethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=NC(OCCOC)=CC(C=2C=3OC(CN4[C@@H](CN(CC4)S(C)(=O)=O)C)=CC=3C(=O)N(C)C=2)=C1 KIWPYLUFZAGLGZ-MRXNPFEDSA-N 0.000 claims description 3
• DDNKKCFLCRCHDR-MRXNPFEDSA-N 7-[3-(cyclopropylmethylamino)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)NCC3CC3)=O)=C2O1 DDNKKCFLCRCHDR-MRXNPFEDSA-N 0.000 claims description 3
• NNADKDPXRPINPF-AAFJCEBUSA-N 7-[3-[(2,2-difluorocyclopropyl)methoxy]pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3C(C3)(F)F)=O)=C2O1 NNADKDPXRPINPF-AAFJCEBUSA-N 0.000 claims description 3
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
• JJTCJPMDVVZKFT-UHFFFAOYSA-N n-[4-[2-[(3,3-difluoropiperidin-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CC(F)(F)CCC4)=CC=3C(=O)N(C)C=2)=C1 JJTCJPMDVVZKFT-UHFFFAOYSA-N 0.000 claims description 3
• HZGGLQPIMIBGMU-UHFFFAOYSA-N n-[4-[2-[(3-fluoropiperidin-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CC(F)CCC4)=CC=3C(=O)N(C)C=2)=C1 HZGGLQPIMIBGMU-UHFFFAOYSA-N 0.000 claims description 3
• SKWUKCZJCFEDGL-UHFFFAOYSA-N 2-(1,4-diazepan-1-ylmethyl)-5-methyl-7-[2-(pyridin-2-ylmethylamino)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCNCCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=NC=1NCC1=CC=CC=N1 SKWUKCZJCFEDGL-UHFFFAOYSA-N 0.000 claims description 2
• WUQUNDCQNMGOJS-UHFFFAOYSA-N 2-[(2-aminoethylamino)methyl]-7-(3,4-dimethoxyphenyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CNCCN)=C2 WUQUNDCQNMGOJS-UHFFFAOYSA-N 0.000 claims description 2
• DDBJXQIYRNMXCR-UHFFFAOYSA-N 2-[(3-fluoropiperidin-1-yl)methyl]-7-(4-methoxyphenyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CC(F)CCC1)=C2 DDBJXQIYRNMXCR-UHFFFAOYSA-N 0.000 claims description 2
• KNDSMZOBNSXMJT-UHFFFAOYSA-N 2-[(4-acetyl-2-methylpiperazin-1-yl)methyl]-5-methyl-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.CC1CN(C(C)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(OCC4CCOCC4)N=CC=3)=O)=C2O1 KNDSMZOBNSXMJT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• XGYILSHXIHSUOO-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-4-[5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]benzoic acid Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C1=CC=C(C(O)=O)C=C1OCC1CC1 XGYILSHXIHSUOO-UHFFFAOYSA-N 0.000 claims description 2
• PBNOUWNDUBZSPQ-UHFFFAOYSA-N 5-methyl-2-[(2-methylpiperazin-1-yl)methyl]-7-[2-(oxan-4-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.CC1CNCCN1CC1=CC(C(N(C)C=C2C=3C=C(OCC4CCOCC4)N=CC=3)=O)=C2O1 PBNOUWNDUBZSPQ-UHFFFAOYSA-N 0.000 claims description 2
• YRTOQQVSMZLXDL-UHFFFAOYSA-N 5-methyl-2-[(4-methyl-1,4-diazepan-1-yl)methyl]-7-[3-(pyridin-2-ylmethylamino)phenyl]furo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.C1CN(C)CCCN1CC1=CC(C(N(C)C=C2C=3C=C(NCC=4N=CC=CC=4)C=CC=3)=O)=C2O1 YRTOQQVSMZLXDL-UHFFFAOYSA-N 0.000 claims description 2
• ANZGHRYXXJSLFU-MRXNPFEDSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-(3-propan-2-yloxypyridin-4-yl)furo[3,2-c]pyridin-4-one Chemical compound CC(C)OC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 ANZGHRYXXJSLFU-MRXNPFEDSA-N 0.000 claims description 2
• ZYZMKDLDCHNQEM-OAHLLOKOSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxetan-3-yloxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC3COC3)=O)=C2O1 ZYZMKDLDCHNQEM-OAHLLOKOSA-N 0.000 claims description 2
• YNJHUYQGNUPNCE-QNSVNVJESA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxolan-2-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3OCCC3)=O)=C2O1 YNJHUYQGNUPNCE-QNSVNVJESA-N 0.000 claims description 2
• AEVIANLNHWLUML-QNSVNVJESA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxolan-3-ylmethoxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3COCC3)=O)=C2O1 AEVIANLNHWLUML-QNSVNVJESA-N 0.000 claims description 2
• XIMCNZHZTMYTKK-TZHYSIJRSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-(oxolan-3-yloxy)pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC3COCC3)=O)=C2O1 XIMCNZHZTMYTKK-TZHYSIJRSA-N 0.000 claims description 2
• XIMCNZHZTMYTKK-IAGOWNOFSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-[(3r)-oxolan-3-yl]oxypyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)O[C@H]3COCC3)=O)=C2O1 XIMCNZHZTMYTKK-IAGOWNOFSA-N 0.000 claims description 2
• XIMCNZHZTMYTKK-SJORKVTESA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-[(3s)-oxolan-3-yl]oxypyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)O[C@@H]3COCC3)=O)=C2O1 XIMCNZHZTMYTKK-SJORKVTESA-N 0.000 claims description 2
• GPNARNKKVSQDKQ-GOSISDBHSA-N 5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-[3-[2-(2-oxopyrrolidin-1-yl)ethoxy]pyridin-4-yl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCCN3C(CCC3)=O)=O)=C2O1 GPNARNKKVSQDKQ-GOSISDBHSA-N 0.000 claims description 2
• HVJNEUPSYMMECJ-CYBMUJFWSA-N 7-(2-aminopyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(N)N=CC=3)=O)=C2O1 HVJNEUPSYMMECJ-CYBMUJFWSA-N 0.000 claims description 2
• VPGFVXUZUMEVBI-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1CCN(CC1)S(C)(=O)=O)=C2 VPGFVXUZUMEVBI-UHFFFAOYSA-N 0.000 claims description 2
• WWQFFZOCZFZRSP-OAHLLOKOSA-N 7-(3-cyclopropyloxypyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OC3CC3)=O)=C2O1 WWQFFZOCZFZRSP-OAHLLOKOSA-N 0.000 claims description 2
• YADJSPPQXGQMCB-OAHLLOKOSA-N 7-(3-ethoxypyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound CCOC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 YADJSPPQXGQMCB-OAHLLOKOSA-N 0.000 claims description 2
• PSNZFFGOHFCPKC-CYBMUJFWSA-N 7-(3-hydroxypyridin-4-yl)-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)O)=O)=C2O1 PSNZFFGOHFCPKC-CYBMUJFWSA-N 0.000 claims description 2
• SJNJBIGYYCYNFE-MRXNPFEDSA-N 7-[2-(cyclopropylmethylamino)pyridin-3-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=NC=CC=3)NCC3CC3)=O)=C2O1 SJNJBIGYYCYNFE-MRXNPFEDSA-N 0.000 claims description 2
• KXDRQTINKBLAEK-TZHYSIJRSA-N 7-[3-(1-methoxypropan-2-yloxy)pyridin-4-yl]-5-methyl-2-[[(2R)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound COCC(C)OC=1C=NC=CC1C=1C2=C(C(N(C1)C)=O)C=C(O2)CN2[C@@H](CN(CC2)S(=O)(=O)C)C KXDRQTINKBLAEK-TZHYSIJRSA-N 0.000 claims description 2
• XDBXEJKUSHELKX-CQSZACIVSA-N 7-[3-(2,2-difluoroethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC(F)F)=O)=C2O1 XDBXEJKUSHELKX-CQSZACIVSA-N 0.000 claims description 2
• DOVCDUXMNSLCHD-OAHLLOKOSA-N 7-[3-(2-fluoroethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCCF)=O)=C2O1 DOVCDUXMNSLCHD-OAHLLOKOSA-N 0.000 claims description 2
• PEZPDAJVRQMYEJ-OAHLLOKOSA-N 7-[3-(2-hydroxyethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCCO)=O)=C2O1 PEZPDAJVRQMYEJ-OAHLLOKOSA-N 0.000 claims description 2
• HODLGFLRFMOVJV-MRXNPFEDSA-N 7-[3-(2-methoxyethoxy)pyridin-4-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound COCCOC1=CN=CC=C1C1=CN(C)C(=O)C2=C1OC(CN1[C@@H](CN(CC1)S(C)(=O)=O)C)=C2 HODLGFLRFMOVJV-MRXNPFEDSA-N 0.000 claims description 2
• AHCHFHKAQDTGRP-UHFFFAOYSA-N 7-[3-(benzylamino)phenyl]-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C(C=1)=CC=CC=1NCC1=CC=CC=C1 AHCHFHKAQDTGRP-UHFFFAOYSA-N 0.000 claims description 2
• JQMULURWMSIZFQ-MRXNPFEDSA-N 7-[3-(cyclopropylmethoxy)pyridin-2-yl]-5-methyl-2-[[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]furo[3,2-c]pyridin-4-one Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1CC1=CC(C(N(C)C=C2C=3C(=CC=CN=3)OCC3CC3)=O)=C2O1 JQMULURWMSIZFQ-MRXNPFEDSA-N 0.000 claims description 2
• KJJPOVWFRRYSDR-UHFFFAOYSA-N 7-[3-(cyclopropylmethoxy)pyridin-4-yl]-2-(1,4-diazepan-1-ylmethyl)-5-methylfuro[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCNCCC3)=CC=2C(=O)N(C)C=C1C1=CC=NC=C1OCC1CC1 KJJPOVWFRRYSDR-UHFFFAOYSA-N 0.000 claims description 2
• FWKQTJUDPNLEAU-UHFFFAOYSA-N 7-[3-(cyclopropylmethoxy)pyridin-4-yl]-5-methyl-2-[(3-oxopiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CC(=O)NCC3)=CC=2C(=O)N(C)C=C1C1=CC=NC=C1OCC1CC1 FWKQTJUDPNLEAU-UHFFFAOYSA-N 0.000 claims description 2
• UVZIUZRPYGJNTP-UHFFFAOYSA-N 7-[3-(cyclopropylmethoxy)pyridin-4-yl]-5-methyl-2-[(4-methyl-1,4-diazepan-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1CN(C)CCCN1CC1=CC(C(N(C)C=C2C=3C(=CN=CC=3)OCC3CC3)=O)=C2O1 UVZIUZRPYGJNTP-UHFFFAOYSA-N 0.000 claims description 2
• UASRHQJXKWCMPH-UHFFFAOYSA-N 7-[4-(aminomethyl)phenyl]-5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]furo[3,2-c]pyridin-4-one Chemical compound C1=2OC(CN3CCN(CC3)S(C)(=O)=O)=CC=2C(=O)N(C)C=C1C1=CC=C(CN)C=C1 UASRHQJXKWCMPH-UHFFFAOYSA-N 0.000 claims description 2
• MCTBSAVNHXJNFR-QEHVYQFBSA-N N-[4-[2-[[(2R)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]-4-oxo-5-(trideuteriomethyl)furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C(N1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN1[C@@H](CN(CC1)S(=O)(=O)C)C)=O)([2H])([2H])[2H] MCTBSAVNHXJNFR-QEHVYQFBSA-N 0.000 claims description 2
• OOQYLEGNEHNVMN-HNNXBMFYSA-N N-[4-[2-[[(3S)-3-hydroxypiperidin-1-yl]methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound O[C@@H]1CN(CCC1)CC1=CC=2C(N(C=C(C2O1)C1=CC(=NC=C1)NC(C)=O)C)=O OOQYLEGNEHNVMN-HNNXBMFYSA-N 0.000 claims description 2
• JDRXGWUWTKFBKZ-UHFFFAOYSA-N N-[4-[5-methyl-2-[(2-methyl-1,1-dioxo-1,4-thiazinan-4-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN2CC(S(CC2)(=O)=O)C)=O JDRXGWUWTKFBKZ-UHFFFAOYSA-N 0.000 claims description 2
• LZCSTAWDCKXCNX-UHFFFAOYSA-N N-[4-[5-methyl-2-[(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN2C(CS(CC2)(=O)=O)C)=O LZCSTAWDCKXCNX-UHFFFAOYSA-N 0.000 claims description 2
• VEZZKWPSOSEKHF-GFCCVEGCSA-N N-[4-[5-methyl-2-[[(2R)-2-methyl-3-oxopiperazin-1-yl]methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN2[C@@H](C(NCC2)=O)C)=O VEZZKWPSOSEKHF-GFCCVEGCSA-N 0.000 claims description 2
• VIEMHNLMWWTWLK-UHFFFAOYSA-N N-[4-[5-methyl-4-oxo-2-(piperidin-1-ylmethyl)furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN2CCCCC2)=O VIEMHNLMWWTWLK-UHFFFAOYSA-N 0.000 claims description 2
• FHHSGVDZBHZKPZ-UHFFFAOYSA-N N-[4-[5-methyl-4-oxo-2-(pyrrolidin-1-ylmethyl)furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN1CCCC1)=O FHHSGVDZBHZKPZ-UHFFFAOYSA-N 0.000 claims description 2
• CLRTZYXNNZFTBH-UHFFFAOYSA-N N-[4-[5-methyl-4-oxo-2-[(3-oxo-1,4-diazepan-1-yl)methyl]furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN2CC(NCCC2)=O)=O CLRTZYXNNZFTBH-UHFFFAOYSA-N 0.000 claims description 2
• HWDLZOJLWICZPS-UHFFFAOYSA-N N-[4-[5-methyl-4-oxo-2-[(5-oxo-1,4-diazepan-1-yl)methyl]furo[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CN1C(C2=C(C(=C1)C1=CC(=NC=C1)NC(C)=O)OC(=C2)CN2CCNC(CC2)=O)=O HWDLZOJLWICZPS-UHFFFAOYSA-N 0.000 claims description 2
• YRQQWYMPNSIIKV-UHFFFAOYSA-N n-[3-[2-(1,4-diazepan-1-ylmethyl)-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]phenyl]pyridine-2-carboxamide Chemical compound C1=2OC(CN3CCNCCC3)=CC=2C(=O)N(C)C=C1C(C=1)=CC=CC=1NC(=O)C1=CC=CC=N1 YRQQWYMPNSIIKV-UHFFFAOYSA-N 0.000 claims description 2
• LZWGKFBQHOAHDG-UHFFFAOYSA-N n-[3-[5-methyl-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=3OC(CN4CCN(CC4)S(C)(=O)=O)=CC=3C(=O)N(C)C=2)=C1 LZWGKFBQHOAHDG-UHFFFAOYSA-N 0.000 claims description 2
• KFCNMDRHLRAMNQ-UHFFFAOYSA-N n-[4-[2-(1,4-diazepan-1-ylmethyl)-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCNCCC4)=CC=3C(=O)N(C)C=2)=C1 KFCNMDRHLRAMNQ-UHFFFAOYSA-N 0.000 claims description 2
• XTOTWTFKZUQJLA-UHFFFAOYSA-N n-[4-[2-[(1,1-dioxo-1,4-thiazepan-4-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCS(=O)(=O)CCC4)=CC=3C(=O)N(C)C=2)=C1 XTOTWTFKZUQJLA-UHFFFAOYSA-N 0.000 claims description 2
• ILVPZAMRMNQVAM-UHFFFAOYSA-N n-[4-[2-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCS(=O)(=O)CC4)=CC=3C(=O)N(C)C=2)=C1 ILVPZAMRMNQVAM-UHFFFAOYSA-N 0.000 claims description 2
• APPVCTWDFGBJAV-UHFFFAOYSA-N n-[4-[2-[(4-acetyl-1,4-diazepan-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCN(CCC4)C(C)=O)=CC=3C(=O)N(C)C=2)=C1 APPVCTWDFGBJAV-UHFFFAOYSA-N 0.000 claims description 2
• KDISANMPGPVFGK-UHFFFAOYSA-N n-[4-[2-[(4-acetyl-2-methylpiperazin-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CC1CN(C(C)=O)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 KDISANMPGPVFGK-UHFFFAOYSA-N 0.000 claims description 2
• XNHPRIVDYPNHBX-UHFFFAOYSA-N n-[4-[2-[(4-ethyl-2-methylpiperazin-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound CC1CN(CC)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 XNHPRIVDYPNHBX-UHFFFAOYSA-N 0.000 claims description 2
• ZHRIXCXEBILGLO-UHFFFAOYSA-N n-[4-[2-[(4-ethyl-3-oxopiperazin-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1C(=O)N(CC)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 ZHRIXCXEBILGLO-UHFFFAOYSA-N 0.000 claims description 2
• GKHIVWDNYHDTJU-UHFFFAOYSA-N n-[4-[2-[(4-ethylpiperazin-1-yl)methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1CN(CC)CCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 GKHIVWDNYHDTJU-UHFFFAOYSA-N 0.000 claims description 2
• FBIMSDPPUYQICZ-UHFFFAOYSA-N n-[4-[2-[[4-(methanesulfonamido)piperidin-1-yl]methyl]-5-methyl-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCC(CC4)NS(C)(=O)=O)=CC=3C(=O)N(C)C=2)=C1 FBIMSDPPUYQICZ-UHFFFAOYSA-N 0.000 claims description 2
• QMFHZGJMBIPJOD-UHFFFAOYSA-N n-[4-[5-methyl-2-(1,4-oxazepan-4-ylmethyl)-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCOCCC4)=CC=3C(=O)N(C)C=2)=C1 QMFHZGJMBIPJOD-UHFFFAOYSA-N 0.000 claims description 2
• NVTGUABYRAQKCI-UHFFFAOYSA-N n-[4-[5-methyl-2-(morpholin-4-ylmethyl)-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C=2C=3OC(CN4CCOCC4)=CC=3C(=O)N(C)C=2)=C1 NVTGUABYRAQKCI-UHFFFAOYSA-N 0.000 claims description 2
• ACAJTXVTNBDQFS-UHFFFAOYSA-N n-[4-[5-methyl-2-[(4-methyl-1,4-diazepan-1-yl)methyl]-4-oxofuro[3,2-c]pyridin-7-yl]pyridin-2-yl]acetamide Chemical compound C1CN(C)CCCN1CC1=CC(C(N(C)C=C2C=3C=C(NC(C)=O)N=CC=3)=O)=C2O1 ACAJTXVTNBDQFS-UHFFFAOYSA-N 0.000 claims description 2
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