JP2012512246A5 - - Google Patents
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- Publication number
- JP2012512246A5 JP2012512246A5 JP2011542212A JP2011542212A JP2012512246A5 JP 2012512246 A5 JP2012512246 A5 JP 2012512246A5 JP 2011542212 A JP2011542212 A JP 2011542212A JP 2011542212 A JP2011542212 A JP 2011542212A JP 2012512246 A5 JP2012512246 A5 JP 2012512246A5
- Authority
- JP
- Japan
- Prior art keywords
- naphthyridin
- oxo
- phenyl
- ylamino
- benzamide
- 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
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- -1 derivatives Substances 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 5
- 102000001253 Protein Kinase Human genes 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 108060006633 protein kinase Proteins 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 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
- 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 1
- DLHUWEHGSBIDBV-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-oxo-n-[4-[(6-oxo-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-1-yl)oxy]phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=CC(OC=3C=4C=5CCCCC=5C(=O)NC=4N=CC=3)=CC=2)=CC=C1 DLHUWEHGSBIDBV-UHFFFAOYSA-N 0.000 claims 1
- LAQMEAGGZNCFDX-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]-5-(trifluoromethylsulfonyloxy)-3,6-dihydro-2H-pyridine-4-carboxylic acid Chemical compound C(C)(C)(C)OC(=O)N1CCC(=C(C1)OS(=O)(=O)C(F)(F)F)C(=O)O LAQMEAGGZNCFDX-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
- KQHDEZLGUZPPLF-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine-1,4-dicarboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C(=O)OCC)=C1B1OC(C)(C)C(C)(C)O1 KQHDEZLGUZPPLF-UHFFFAOYSA-N 0.000 claims 1
- VOAVTORWJQDFET-UHFFFAOYSA-N 1-o-tert-butyl 5-o-ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine-1,5-dicarboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CC(C(=O)OCC)=C1B1OC(C)(C)C(C)(C)O1 VOAVTORWJQDFET-UHFFFAOYSA-N 0.000 claims 1
- QBSFHOMPPMKXAV-UHFFFAOYSA-N 1-o-tert-butyl 5-o-ethyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1,5-dicarboxylate Chemical compound CCOC(=O)C1=C(OS(=O)(=O)C(F)(F)F)CCN(C(=O)OC(C)(C)C)C1 QBSFHOMPPMKXAV-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
- QZCBYZPWBXBBAC-UHFFFAOYSA-N 4-fluoro-n-[2-fluoro-4-[(6-oxo-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-1-yl)amino]phenyl]-2-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(=O)NC(C(=C1)F)=CC=C1NC1=CC=NC2=C1C(CCCC1)=C1C(=O)N2 QZCBYZPWBXBBAC-UHFFFAOYSA-N 0.000 claims 1
- KVJYAJCMRIOOQB-UHFFFAOYSA-N 4-fluoro-n-[3-fluoro-4-[(6-oxo-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-1-yl)amino]phenyl]-2-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1C(=O)NC(C=C1F)=CC=C1NC1=CC=NC2=C1C(CCCC1)=C1C(=O)N2 KVJYAJCMRIOOQB-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
- VGWCCIWNLDOJPC-UHFFFAOYSA-N 9-chloro-3,5-dihydropyrazolo[3,4-c][1,8]naphthyridin-4-one Chemical compound N1C(=O)C2=NNC=C2C2=C1N=CC=C2Cl VGWCCIWNLDOJPC-UHFFFAOYSA-N 0.000 claims 1
- UBOIEMIWOMLCGZ-UHFFFAOYSA-N 9-chloro-5h-furo[3,2-c][1,8]naphthyridin-4-one Chemical compound C1=2C(Cl)=CC=NC=2NC(=O)C2=C1OC=C2 UBOIEMIWOMLCGZ-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 102000004000 Aurora Kinase A Human genes 0.000 claims 1
- 108090000461 Aurora Kinase A Proteins 0.000 claims 1
- 102000004228 Aurora kinase B Human genes 0.000 claims 1
- 108090000749 Aurora kinase B Proteins 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000005590 Choroidal Neovascularization Diseases 0.000 claims 1
- 206010060823 Choroidal neovascularisation Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- SVEPOXKKJPLVLF-UHFFFAOYSA-N Fc1ccc(C(=O)Nc2ccc(Nc3ccnc4[nH]c(=O)c5CN(Cc6ccccc6)CCc5c34)cc2)c(c1)C(F)(F)F Chemical compound Fc1ccc(C(=O)Nc2ccc(Nc3ccnc4[nH]c(=O)c5CN(Cc6ccccc6)CCc5c34)cc2)c(c1)C(F)(F)F SVEPOXKKJPLVLF-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 101150081525 LIMK1 gene Proteins 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000005441 aurora Substances 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- TWIPINIEXIHZMO-UHFFFAOYSA-N ethyl 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(B2OC(C)(C)C(C)(C)O2)CCN1CC1=CC=CC=C1 TWIPINIEXIHZMO-UHFFFAOYSA-N 0.000 claims 1
- RGFUCKMAZMCXNU-UHFFFAOYSA-N ethyl 1-benzyl-4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(OS(=O)(=O)C(F)(F)F)CCN1CC1=CC=CC=C1 RGFUCKMAZMCXNU-UHFFFAOYSA-N 0.000 claims 1
- DUQUMTYYZAUNHP-UHFFFAOYSA-N ethyl 1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine-4-carboxylate Chemical compound C1CC(C(=O)OCC)=C(B2OC(C)(C)C(C)(C)O2)CN1CC1=CC=CC=C1 DUQUMTYYZAUNHP-UHFFFAOYSA-N 0.000 claims 1
- WDKZZEZCLYEOEB-UHFFFAOYSA-N ethyl 1-benzyl-5-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-4-carboxylate Chemical compound C1CC(C(=O)OCC)=C(OS(=O)(=O)C(F)(F)F)CN1CC1=CC=CC=C1 WDKZZEZCLYEOEB-UHFFFAOYSA-N 0.000 claims 1
- LRAWEULWMCQGQZ-UHFFFAOYSA-N ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexene-1-carboxylate Chemical compound C1CCCC(C(=O)OCC)=C1B1OC(C)(C)C(C)(C)O1 LRAWEULWMCQGQZ-UHFFFAOYSA-N 0.000 claims 1
- VWIUHGUFSGOXDX-UHFFFAOYSA-N ethyl 2-(trifluoromethylsulfonyloxy)cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C(OS(=O)(=O)C(F)(F)F)CCCC1 VWIUHGUFSGOXDX-UHFFFAOYSA-N 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 1
- HAAGMUVDMARGDH-UHFFFAOYSA-N n-[4-[(3-benzyl-5-oxo-1,2,4,6-tetrahydropyrido[3,4-c][1,8]naphthyridin-10-yl)amino]phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1)=CC=C1NC(C=1C=2CC3)=CC=NC=1NC(=O)C=2CN3CC1=CC=CC=C1 HAAGMUVDMARGDH-UHFFFAOYSA-N 0.000 claims 1
- VYEGWHUFVBJVGI-UHFFFAOYSA-N n-[4-[(4-oxo-3,5-dihydropyrazolo[3,4-c][1,8]naphthyridin-9-yl)amino]phenyl]benzamide Chemical compound C=1C=C(NC=2C=3C4=CNN=C4C(=O)NC=3N=CC=2)C=CC=1NC(=O)C1=CC=CC=C1 VYEGWHUFVBJVGI-UHFFFAOYSA-N 0.000 claims 1
- ZXPJJIWBIVGQSO-UHFFFAOYSA-N n-[4-[(4-oxo-5h-furo[3,2-c][1,8]naphthyridin-9-yl)amino]phenyl]benzamide Chemical compound C=1C=C(NC=2C=3C=4OC=CC=4C(=O)NC=3N=CC=2)C=CC=1NC(=O)C1=CC=CC=C1 ZXPJJIWBIVGQSO-UHFFFAOYSA-N 0.000 claims 1
- DCHZFESTRBTTRY-UHFFFAOYSA-N n-[4-[(5-oxo-2,3,4,6-tetrahydro-1h-pyrido[3,4-c][1,8]naphthyridin-10-yl)amino]phenyl]benzamide Chemical compound C=1C=C(NC=2C=3C=4CCNCC=4C(=O)NC=3N=CC=2)C=CC=1NC(=O)C1=CC=CC=C1 DCHZFESTRBTTRY-UHFFFAOYSA-N 0.000 claims 1
- UWGKXHNAXBGYKC-UHFFFAOYSA-N n-[4-[(6-oxo-7,8,9,10-tetrahydro-5h-benzo[c][1,8]naphthyridin-1-yl)amino]phenyl]benzamide Chemical compound C=1C=C(NC=2C=3C=4CCCCC=4C(=O)NC=3N=CC=2)C=CC=1NC(=O)C1=CC=CC=C1 UWGKXHNAXBGYKC-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- FTWDQGAMMJBIQA-UHFFFAOYSA-N tert-butyl 10-chloro-5-oxo-1,2,4,6-tetrahydropyrido[3,4-c][1,8]naphthyridine-3-carboxylate Chemical compound O=C1NC2=NC=CC(Cl)=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 FTWDQGAMMJBIQA-UHFFFAOYSA-N 0.000 claims 1
- UINFXYIFKAOPOF-UHFFFAOYSA-N tert-butyl 10-chloro-5-oxo-1,3,4,6-tetrahydropyrido[4,3-c][1,8]naphthyridine-2-carboxylate Chemical compound C12=C(Cl)C=CN=C2NC(=O)C2=C1CN(C(=O)OC(C)(C)C)CC2 UINFXYIFKAOPOF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 230000005740 tumor formation Effects 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20196108P | 2008-12-17 | 2008-12-17 | |
| US61/201,961 | 2008-12-17 | ||
| PCT/US2009/066319 WO2010077530A1 (en) | 2008-12-17 | 2009-12-02 | C-ring modified tricyclic benzonaphthiridinone protein kinase inhibitors and use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015121956A Division JP6378138B2 (ja) | 2008-12-17 | 2015-06-17 | Ｃ環修飾型三環式ベンゾナフチリジノン・タンパク質キナーゼ阻害薬及びこれらの使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012512246A JP2012512246A (ja) | 2012-05-31 |
| JP2012512246A5 true JP2012512246A5 (https=) | 2013-01-24 |
Family
ID=41786024
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542212A Pending JP2012512246A (ja) | 2008-12-17 | 2009-12-02 | Ｃ環修飾型三環式ベンゾナフチリジノン・タンパク質キナーゼ阻害薬及びこれらの使用 |
| JP2015121956A Expired - Fee Related JP6378138B2 (ja) | 2008-12-17 | 2015-06-17 | Ｃ環修飾型三環式ベンゾナフチリジノン・タンパク質キナーゼ阻害薬及びこれらの使用 |
Family Applications After (1)
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| JP2015121956A Expired - Fee Related JP6378138B2 (ja) | 2008-12-17 | 2015-06-17 | Ｃ環修飾型三環式ベンゾナフチリジノン・タンパク質キナーゼ阻害薬及びこれらの使用 |
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| US (1) | US9938268B2 (https=) |
| EP (1) | EP2367821B1 (https=) |
| JP (2) | JP2012512246A (https=) |
| AU (1) | AU2009333653B2 (https=) |
| CA (1) | CA2745071C (https=) |
| ES (1) | ES2550101T3 (https=) |
| IL (1) | IL213588A0 (https=) |
| WO (1) | WO2010077530A1 (https=) |
Families Citing this family (4)
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|---|---|---|---|---|
| TWI551600B (zh) | 2011-09-30 | 2016-10-01 | Ｃ＆Ｃ新藥研究所 | 新穎雜環衍生物及其用途 |
| EA030003B1 (ru) | 2012-12-21 | 2018-06-29 | Джилид Сайэнс, Инк. | Полициклическое карбамоилпиридоновое соединение и его фармацевтическое применение для лечения вич-инфекции |
| TWI695003B (zh) * | 2014-12-23 | 2020-06-01 | 美商基利科學股份有限公司 | 多環胺甲醯基吡啶酮化合物及其醫藥用途 |
| CN115611896A (zh) * | 2021-07-16 | 2023-01-17 | 中国药科大学 | 含四氢萘啶酮或四氢吡啶并嘧啶酮骨架的化合物及其制备方法与制药用途 |
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| JPS4961198A (https=) * | 1972-10-14 | 1974-06-13 | ||
| US4680298A (en) * | 1983-05-31 | 1987-07-14 | Schering Corporation | Tricyclic anti-allergy and use as anti-inflammatory agents |
| US4596809A (en) * | 1985-03-25 | 1986-06-24 | Schering Corporation | Substituted 1,8-naphthyridinones, useful as anti-allergic agents |
| DE3786036T2 (de) * | 1986-04-11 | 1993-09-09 | Schering Corp | Arylsubstituierte naphthyridin- und pyridopyrazin-derivate. |
| CA1309658C (en) * | 1986-12-05 | 1992-11-03 | David J. Blythin | Pharmaceutical compositions for treatment of hyperproliferate skin disease |
| ATE143661T1 (de) * | 1990-06-01 | 1996-10-15 | Kyowa Hakko Kogyo Kk | Imidazonaphthyridinderivate |
| JPH0961198A (ja) * | 1995-08-25 | 1997-03-07 | Nippon Seiki Co Ltd | 計器装置 |
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| US6291455B1 (en) | 1996-03-05 | 2001-09-18 | Zeneca Limited | 4-anilinoquinazoline derivatives |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| IL153484A0 (en) | 2000-07-07 | 2003-07-06 | Angiogene Pharm Ltd | Colchinol derivatives as angiogenesis inhibitors |
| CN1255392C (zh) | 2000-07-07 | 2006-05-10 | 安吉奥金尼药品有限公司 | 作为血管生成抑制剂的秋水仙醇衍生物 |
| MXPA03004832A (es) | 2000-12-01 | 2004-05-04 | Guilford Pharm Inc | Compuestos y sus usos. |
| AU2003272175A1 (en) | 2002-10-21 | 2004-05-04 | Aprea Ab | Reactivation of wild type p53 in human tumour cells by a low molecular weight compound |
| WO2005118583A1 (en) * | 2004-05-28 | 2005-12-15 | Millennium Pharmaceuticals, Inc. | 2, 5-dihydro-pyrazolo`4, 3-c!quinolin-4-ones as chk-1 inhibitors |
| EP1910365A4 (en) * | 2005-07-22 | 2009-07-15 | Merck & Co Inc | INHIBITORS OF CHECKPOINT KINASES |
| JP2010500961A (ja) | 2006-08-02 | 2010-01-14 | 武田薬品工業株式会社 | α−カルボリン誘導体およびその製造方法 |
| US7956064B2 (en) | 2006-09-01 | 2011-06-07 | Cylene Pharmaceuticals, Inc. | Fused tricyclic compounds as serine-threonine protein kinase and PARP modulators |
| ES2401550T3 (es) * | 2008-02-28 | 2013-04-22 | Merck Patent Gmbh | Inhibidores de proteína cinasa y uso de los mismos |
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2009
- 2009-12-02 JP JP2011542212A patent/JP2012512246A/ja active Pending
- 2009-12-02 WO PCT/US2009/066319 patent/WO2010077530A1/en not_active Ceased
- 2009-12-02 ES ES09765193.9T patent/ES2550101T3/es active Active
- 2009-12-02 AU AU2009333653A patent/AU2009333653B2/en not_active Ceased
- 2009-12-02 CA CA2745071A patent/CA2745071C/en not_active Expired - Fee Related
- 2009-12-02 US US13/140,090 patent/US9938268B2/en not_active Expired - Fee Related
- 2009-12-02 EP EP09765193.9A patent/EP2367821B1/en not_active Not-in-force
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2011
- 2011-06-16 IL IL213588A patent/IL213588A0/en unknown
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2015
- 2015-06-17 JP JP2015121956A patent/JP6378138B2/ja not_active Expired - Fee Related
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