ES2550101T3 - Inhibidores de proteína quinasa de benzonaftiridinona tricíclica modificada con anillo C y su uso - Google Patents

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Publication number

ES2550101T3

ES2550101T3 ES09765193.9T ES09765193T ES2550101T3 ES 2550101 T3 ES2550101 T3 ES 2550101T3 ES 09765193 T ES09765193 T ES 09765193T ES 2550101 T3 ES2550101 T3 ES 2550101T3

Authority

ES

Spain

Prior art keywords

naphthyridin

aryl

phenyl

oxo

ylamino

Prior art date

2008-12-17

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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• 239000003909 protein kinase inhibitor Substances 0.000 title description 7
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 5
• MMQLBTDCVNCJBE-UHFFFAOYSA-N 1h-benzo[b][1,8]naphthyridin-2-one Chemical compound C1=CC=C2N=C(NC(=O)C=C3)C3=CC2=C1 MMQLBTDCVNCJBE-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 138
• 150000003839 salts Chemical class 0.000 claims abstract description 73
• 239000000203 mixture Substances 0.000 claims abstract description 50
• 125000003118 aryl group Chemical group 0.000 claims abstract description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 28
• 239000012453 solvate Substances 0.000 claims abstract description 23
• 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 13
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
• 125000001475 halogen functional group Chemical group 0.000 claims abstract description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
• 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
• -1 6-oxo-5,6,7,8,9,10-hexahydrobenzo [c] [1,8] naphthyridin-1-ylamino Chemical group 0.000 claims description 162
• 238000011282 treatment Methods 0.000 claims description 36
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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• WVRGHMFRCUZEJB-UHFFFAOYSA-N 1-(4-aminophenoxy)-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C1=CC(N)=CC=C1OC1=CC=NC2=C1C(CCCC1)=C1C(=O)N2 WVRGHMFRCUZEJB-UHFFFAOYSA-N 0.000 claims 2
• KTCNGKASVZVXHT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CNC1 KTCNGKASVZVXHT-UHFFFAOYSA-N 0.000 claims 1
• NRRYULIIACYLDV-UHFFFAOYSA-N 1-(3,4-dihydro-2h-1,4-benzoxazin-7-yloxy)-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C1CCCC2=C1C1=C(OC=3C=C4OCCNC4=CC=3)C=CN=C1NC2=O NRRYULIIACYLDV-UHFFFAOYSA-N 0.000 claims 1
• AGIJDZPJJJSYEC-UHFFFAOYSA-N 1-(3-phenylmethoxyanilino)-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C=12C=3CCCCC=3C(=O)NC2=NC=CC=1NC(C=1)=CC=CC=1OCC1=CC=CC=C1 AGIJDZPJJJSYEC-UHFFFAOYSA-N 0.000 claims 1
• DJHCEZMMYXJWCS-UHFFFAOYSA-N 1-[(5-chloro-1,3-benzodioxol-4-yl)amino]-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C1CCCC2=C1C(=O)NC1=C2C(NC2=C3OCOC3=CC=C2Cl)=CC=N1 DJHCEZMMYXJWCS-UHFFFAOYSA-N 0.000 claims 1
• WOXAGWCPBCMTSR-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-methylphenyl)pyrazol-3-yl]-3-[4-[(6-oxo-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-1-yl)oxy]phenyl]urea Chemical compound CC1=CC=CC(N2C(=CC(=N2)C(C)(C)C)NC(=O)NC=2C=CC(OC=3C=4C=5CCCCC=5C(=O)NC=4N=CC=3)=CC=2)=C1 WOXAGWCPBCMTSR-UHFFFAOYSA-N 0.000 claims 1
• RSIUBFJHQIJBIQ-UHFFFAOYSA-N 1-[[4-[1-(4-fluorophenyl)-2-oxopyridine-3-carbonyl]-2,3-dihydro-1,4-benzoxazin-7-yl]oxy]-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)N2C3=CC=C(OC=4C=5C=6CCCCC=6C(=O)NC=5N=CC=4)C=C3OCC2)=CC=C1 RSIUBFJHQIJBIQ-UHFFFAOYSA-N 0.000 claims 1
• ZXWWZGRGUXBCPW-UHFFFAOYSA-N 1-chloro-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C1CCCC2=C1C(=O)NC1=C2C(Cl)=CC=N1 ZXWWZGRGUXBCPW-UHFFFAOYSA-N 0.000 claims 1
• VYDLSGISEVNDKY-UHFFFAOYSA-N 1-quinolin-7-yloxy-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-6-one Chemical compound C1CCCC2=C1C1=C(OC=3C=C4N=CC=CC4=CC=3)C=CN=C1NC2=O VYDLSGISEVNDKY-UHFFFAOYSA-N 0.000 claims 1
• CBQGQPAZGVWOOH-UHFFFAOYSA-N 2-bromo-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound C12=CC=CN=C2NC(=O)C2=C1OC(Br)=C2 CBQGQPAZGVWOOH-UHFFFAOYSA-N 0.000 claims 1
• KVSQFHQIORLIBZ-UHFFFAOYSA-N 2-fluoro-n-[4-[(6-oxo-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-1-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC=C(C(F)(F)F)C(F)=C1C(=O)NC(C=C1)=CC=C1NC1=CC=NC2=C1C(CCCC1)=C1C(=O)N2 KVSQFHQIORLIBZ-UHFFFAOYSA-N 0.000 claims 1
• SSJNXTGCPUCMAN-UHFFFAOYSA-N 3,4-difluoro-n-[4-[(5-oxo-2,3,4,6-tetrahydro-1h-pyrido[3,4-c][1,8]naphthyridin-10-yl)amino]phenyl]benzamide Chemical compound C1=C(F)C(F)=CC=C1C(=O)NC(C=C1)=CC=C1NC1=CC=NC2=C1C(CCNC1)=C1C(=O)N2 SSJNXTGCPUCMAN-UHFFFAOYSA-N 0.000 claims 1
• XNWCQJLBPFOABL-UHFFFAOYSA-N 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1,5-dicarboxylic acid Chemical compound OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=C(C(O)=O)C1 XNWCQJLBPFOABL-UHFFFAOYSA-N 0.000 claims 1
• LSALKUPDTIXZJU-UHFFFAOYSA-N 4-fluoro-n-[4-[(5-oxo-2,3,4,6-tetrahydro-1h-pyrido[3,4-c][1,8]naphthyridin-10-yl)amino]phenyl]-2-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(=O)NC(C=C1)=CC=C1NC1=CC=NC2=C1C(CCNC1)=C1C(=O)N2 LSALKUPDTIXZJU-UHFFFAOYSA-N 0.000 claims 1
• DMLGTGVDUXJRNS-UHFFFAOYSA-N 5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound O=C1NC2=NC=CC=C2C2=C1C=CO2 DMLGTGVDUXJRNS-UHFFFAOYSA-N 0.000 claims 1
• IJYXPNAXRVDKHS-UHFFFAOYSA-N 5h-thieno[3,2-c][1,8]naphthyridin-4-one Chemical compound O=C1NC2=NC=CC=C2C2=C1C=CS2 IJYXPNAXRVDKHS-UHFFFAOYSA-N 0.000 claims 1
• XGAUPBFYMFAJIS-UHFFFAOYSA-N 9-(3-chloroanilino)-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound ClC1=CC=CC(NC=2C=3C=4OC=CC=4C(=O)NC=3N=CC=2)=C1 XGAUPBFYMFAJIS-UHFFFAOYSA-N 0.000 claims 1
• MCSXIEVZQSGRJD-UHFFFAOYSA-N 9-(3-methoxyanilino)-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound COC1=CC=CC(NC=2C=3C=4OC=CC=4C(=O)NC=3N=CC=2)=C1 MCSXIEVZQSGRJD-UHFFFAOYSA-N 0.000 claims 1
• WJTJBXCCDALTRN-UHFFFAOYSA-N 9-(4-chloroanilino)-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound C1=CC(Cl)=CC=C1NC1=CC=NC2=C1C(OC=C1)=C1C(=O)N2 WJTJBXCCDALTRN-UHFFFAOYSA-N 0.000 claims 1
• IGXYKNFZOKAVJY-UHFFFAOYSA-N 9-(4-methoxyanilino)-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC2=C1C(OC=C1)=C1C(=O)N2 IGXYKNFZOKAVJY-UHFFFAOYSA-N 0.000 claims 1
• RXERALKQELAEBI-UHFFFAOYSA-N 9-anilino-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound C=12C=3OC=CC=3C(=O)NC2=NC=CC=1NC1=CC=CC=C1 RXERALKQELAEBI-UHFFFAOYSA-N 0.000 claims 1
• CLFYTABSRQFXOA-UHFFFAOYSA-N 9-chloro-2-trityl-5h-pyrazolo[3,4-c][1,8]naphthyridin-4-one Chemical compound C1=C2C=3C(Cl)=CC=NC=3NC(=O)C2=NN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CLFYTABSRQFXOA-UHFFFAOYSA-N 0.000 claims 1
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