ES2964531T3 - Derivados de ftalazina como inhibidores de PARP1, PARP2 y/o tubulina útiles para el tratamiento del cáncer - Google Patents
Derivados de ftalazina como inhibidores de PARP1, PARP2 y/o tubulina útiles para el tratamiento del cáncer Download PDFInfo
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- ES2964531T3 ES2964531T3 ES17737132T ES17737132T ES2964531T3 ES 2964531 T3 ES2964531 T3 ES 2964531T3 ES 17737132 T ES17737132 T ES 17737132T ES 17737132 T ES17737132 T ES 17737132T ES 2964531 T3 ES2964531 T3 ES 2964531T3
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- ZLXGQWHDWKWNCR-UHFFFAOYSA-N ethyl N-[4-fluoro-5-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=CC=2NC(=NC=21)NC(OCC)=O)C1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)F ZLXGQWHDWKWNCR-UHFFFAOYSA-N 0.000 description 1
- WCHABVXUKRMBSC-UHFFFAOYSA-N ethyl N-[4-fluoro-6-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=CC(=CC2=C1NC(=N2)NC(OCC)=O)C1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)F WCHABVXUKRMBSC-UHFFFAOYSA-N 0.000 description 1
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- IFHIXHBKCKZGJO-UHFFFAOYSA-N ethyl N-[6-[2,3-dimethoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C=C1OC)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 IFHIXHBKCKZGJO-UHFFFAOYSA-N 0.000 description 1
- UYNBDAXGXUAUSV-UHFFFAOYSA-N ethyl N-[6-[2,4-difluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C(=C1)F)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 UYNBDAXGXUAUSV-UHFFFAOYSA-N 0.000 description 1
- FZNIVYNOIRQVPP-UHFFFAOYSA-N ethyl N-[6-[2,4-dimethoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C(=C1)OC)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 FZNIVYNOIRQVPP-UHFFFAOYSA-N 0.000 description 1
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- NCEOPDPCJWHTKY-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-3-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=CC=C1CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 NCEOPDPCJWHTKY-UHFFFAOYSA-N 0.000 description 1
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- WMQIKUVJFOFMFZ-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-5-[(5-fluoro-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=C(C=CC=C12)F)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 WMQIKUVJFOFMFZ-UHFFFAOYSA-N 0.000 description 1
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- XHHHAQGMRVCQHQ-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-5-[(7-methoxy-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)OC)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 XHHHAQGMRVCQHQ-UHFFFAOYSA-N 0.000 description 1
- MQESDNHNYHUFFB-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-5-[(7-methyl-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)C)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 MQESDNHNYHUFFB-UHFFFAOYSA-N 0.000 description 1
- IIYDPYAUQAOLQS-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-5-[(8-fluoro-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC(=C12)F)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 IIYDPYAUQAOLQS-UHFFFAOYSA-N 0.000 description 1
- LVJHCNNWVCSJBY-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-5-[[4-oxo-7-(trifluoromethoxy)-3H-phthalazin-1-yl]methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)OC(F)(F)F)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 LVJHCNNWVCSJBY-UHFFFAOYSA-N 0.000 description 1
- IFDBUOAQVNYTSC-UHFFFAOYSA-N ethyl N-[6-[2-fluoro-5-[[4-oxo-7-(trifluoromethyl)-3H-phthalazin-1-yl]methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)C(F)(F)F)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 IFDBUOAQVNYTSC-UHFFFAOYSA-N 0.000 description 1
- XYVWONDZKYVZLV-UHFFFAOYSA-N ethyl N-[6-[2-methoxy-3-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=CC=C1CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 XYVWONDZKYVZLV-UHFFFAOYSA-N 0.000 description 1
- SNMYDCNSOCDZTJ-UHFFFAOYSA-N ethyl N-[6-[2-methoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OCC)=O)C=C1 SNMYDCNSOCDZTJ-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 208000006178 malignant mesothelioma Diseases 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- XDEDQFYJKLYLMQ-UHFFFAOYSA-N methyl 2-[[6-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamoylamino]acetate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(=O)NCC(=O)OC)C=C1 XDEDQFYJKLYLMQ-UHFFFAOYSA-N 0.000 description 1
- MDFIQSWXMAOVCJ-UHFFFAOYSA-N methyl N,N'-bis(methylsulfonyl)carbamimidothioate Chemical compound CSC(NS(=O)(=O)C)=NS(=O)(=O)C MDFIQSWXMAOVCJ-UHFFFAOYSA-N 0.000 description 1
- KEMOYZPVUPGVDY-UHFFFAOYSA-N methyl N-[4-chloro-6-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound ClC1=CC(=CC2=C1NC(=N2)NC(OC)=O)C1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)F KEMOYZPVUPGVDY-UHFFFAOYSA-N 0.000 description 1
- VJEWHHGMVOVNJT-UHFFFAOYSA-N methyl N-[4-fluoro-5-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=CC=2NC(=NC=21)NC(OC)=O)C1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)F VJEWHHGMVOVNJT-UHFFFAOYSA-N 0.000 description 1
- HYSWMCCQQWDQQJ-UHFFFAOYSA-N methyl N-[4-fluoro-6-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=CC(=CC2=C1NC(=N2)NC(OC)=O)C1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)F HYSWMCCQQWDQQJ-UHFFFAOYSA-N 0.000 description 1
- KIKQYRZPCAKGSN-UHFFFAOYSA-N methyl N-[5-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC=C2C(=N1)N=C(N2)NC(OC)=O KIKQYRZPCAKGSN-UHFFFAOYSA-N 0.000 description 1
- BFMYFWSOJPBRLR-UHFFFAOYSA-N methyl N-[6-[2,3-difluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1F)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 BFMYFWSOJPBRLR-UHFFFAOYSA-N 0.000 description 1
- IBTQQRPXOJAXRE-UHFFFAOYSA-N methyl N-[6-[2,3-dimethoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C=C1OC)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 IBTQQRPXOJAXRE-UHFFFAOYSA-N 0.000 description 1
- LRTMYSPBTVIVHQ-UHFFFAOYSA-N methyl N-[6-[2,4-difluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C(=C1)F)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 LRTMYSPBTVIVHQ-UHFFFAOYSA-N 0.000 description 1
- GEWCABZZXVENGF-UHFFFAOYSA-N methyl N-[6-[2,4-dimethoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C(=C1)OC)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 GEWCABZZXVENGF-UHFFFAOYSA-N 0.000 description 1
- HAYLBMYMZQSXGU-UHFFFAOYSA-N methyl N-[6-[2-(2-methoxyethoxy)-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COCCOC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 HAYLBMYMZQSXGU-UHFFFAOYSA-N 0.000 description 1
- JNVIPYXVSLJYLW-UHFFFAOYSA-N methyl N-[6-[2-(difluoromethoxy)-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC(OC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)F JNVIPYXVSLJYLW-UHFFFAOYSA-N 0.000 description 1
- MQNDBQMJSMLPDQ-UHFFFAOYSA-N methyl N-[6-[2-chloro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound ClC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 MQNDBQMJSMLPDQ-UHFFFAOYSA-N 0.000 description 1
- BMWPGRUXLXUSLC-UHFFFAOYSA-N methyl N-[6-[2-ethoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound C(C)OC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 BMWPGRUXLXUSLC-UHFFFAOYSA-N 0.000 description 1
- VXQCQVLTXJMUDV-UHFFFAOYSA-N methyl N-[6-[2-fluoro-3-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=CC=C1CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 VXQCQVLTXJMUDV-UHFFFAOYSA-N 0.000 description 1
- ACKZIHJQAJKSAB-UHFFFAOYSA-N methyl N-[6-[2-fluoro-4-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)C=1C=CC2=C(NC(=N2)NC(OC)=O)C=1 ACKZIHJQAJKSAB-UHFFFAOYSA-N 0.000 description 1
- ZPSVQQSLFZYHLP-UHFFFAOYSA-N methyl N-[6-[2-fluoro-4-methoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C(=C1)OC)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 ZPSVQQSLFZYHLP-UHFFFAOYSA-N 0.000 description 1
- NVIQLRKCRFZLMN-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 NVIQLRKCRFZLMN-UHFFFAOYSA-N 0.000 description 1
- GADMCKQMSNENFG-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-3H-imidazo[4,5-c]pyridin-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(C=N1)NC(=N2)NC(OC)=O GADMCKQMSNENFG-UHFFFAOYSA-N 0.000 description 1
- WPYHMYLSVZCDCF-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(5-fluoro-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=C(C=CC=C12)F)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 WPYHMYLSVZCDCF-UHFFFAOYSA-N 0.000 description 1
- FGGKOIDRGPWPKY-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(5-methyl-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=C(C=CC=C12)C)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 FGGKOIDRGPWPKY-UHFFFAOYSA-N 0.000 description 1
- OJPCTBBWFNPFCW-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(6-fluoro-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC(=CC=C12)F)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 OJPCTBBWFNPFCW-UHFFFAOYSA-N 0.000 description 1
- IREZUAHGOYIHNV-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(6-methyl-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC(=CC=C12)C)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 IREZUAHGOYIHNV-UHFFFAOYSA-N 0.000 description 1
- KJFVZKNHKSYLPJ-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(7-fluoro-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)F)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 KJFVZKNHKSYLPJ-UHFFFAOYSA-N 0.000 description 1
- NFASPDFCWLNYRW-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(7-methoxy-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)OC)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 NFASPDFCWLNYRW-UHFFFAOYSA-N 0.000 description 1
- RMBKATFFVGAVIJ-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(7-methyl-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound C1=2C(=NNC(=O)C=2C=CC(=C1)C)CC1=CC(C2=CC=C3NC(=NC3=C2)NC(=O)OC)=C(F)C=C1 RMBKATFFVGAVIJ-UHFFFAOYSA-N 0.000 description 1
- DCOSVOCTMZJITN-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[(8-fluoro-4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC(=C12)F)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 DCOSVOCTMZJITN-UHFFFAOYSA-N 0.000 description 1
- KHXLUNFQPGNFOB-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[[4-oxo-7-(trifluoromethoxy)-3H-phthalazin-1-yl]methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)OC(F)(F)F)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 KHXLUNFQPGNFOB-UHFFFAOYSA-N 0.000 description 1
- UMVSGXQEFKRZEO-UHFFFAOYSA-N methyl N-[6-[2-fluoro-5-[[4-oxo-7-(trifluoromethyl)-3H-phthalazin-1-yl]methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)CC1=NNC(C2=CC=C(C=C12)C(F)(F)F)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 UMVSGXQEFKRZEO-UHFFFAOYSA-N 0.000 description 1
- VUGMLTJJQRZQJW-UHFFFAOYSA-N methyl N-[6-[2-methoxy-3-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=CC=C1CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 VUGMLTJJQRZQJW-UHFFFAOYSA-N 0.000 description 1
- SQCFQLVICCODFZ-UHFFFAOYSA-N methyl N-[6-[2-methoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 SQCFQLVICCODFZ-UHFFFAOYSA-N 0.000 description 1
- KALDDRFSNHQNCA-UHFFFAOYSA-N methyl N-[6-[2-methyl-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound CC1=C(C=C(C=C1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 KALDDRFSNHQNCA-UHFFFAOYSA-N 0.000 description 1
- ZOHILDIKKKZXBW-UHFFFAOYSA-N methyl N-[6-[3-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC=1C=C(C=C(C=1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 ZOHILDIKKKZXBW-UHFFFAOYSA-N 0.000 description 1
- CJRVXDQJXKVLFW-UHFFFAOYSA-N methyl N-[6-[3-methoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC=1C=C(C=C(C=1)CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1 CJRVXDQJXKVLFW-UHFFFAOYSA-N 0.000 description 1
- VENZJEZUOIWLQU-UHFFFAOYSA-N methyl N-[6-[4-fluoro-2-methoxy-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=CC(=C(C=C1CC1=NNC(C2=CC=CC=C12)=O)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)OC VENZJEZUOIWLQU-UHFFFAOYSA-N 0.000 description 1
- PVOTWJKCAAOLSB-UHFFFAOYSA-N methyl N-[6-[4-fluoro-3-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C(C=C(C=C1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)CC1=NNC(C2=CC=CC=C12)=O PVOTWJKCAAOLSB-UHFFFAOYSA-N 0.000 description 1
- GNGGKUSZRCTVDS-UHFFFAOYSA-N methyl N-[6-[4-methoxy-3-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC1=C(C=C(C=C1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)CC1=NNC(C2=CC=CC=C12)=O GNGGKUSZRCTVDS-UHFFFAOYSA-N 0.000 description 1
- LUMOFIFKADGVJU-UHFFFAOYSA-N methyl N-[6-[5-[(4-oxo-3H-phthalazin-1-yl)methyl]-2-(trifluoromethoxy)phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound C1=C(CC=2C3=CC=CC=C3C(=O)NN=2)C=C(C2=CC=C3NC(=NC3=C2)NC(=O)OC)C(OC(F)(F)F)=C1 LUMOFIFKADGVJU-UHFFFAOYSA-N 0.000 description 1
- UQIFKXKLBPEQSC-UHFFFAOYSA-N methyl N-[6-[5-[(4-oxo-3H-phthalazin-1-yl)methyl]-2-(trifluoromethyl)phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound O=C1NN=C(C2=CC=CC=C12)CC=1C=CC(=C(C=1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)C(F)(F)F UQIFKXKLBPEQSC-UHFFFAOYSA-N 0.000 description 1
- IHNRINCYMNAWAX-UHFFFAOYSA-N methyl N-[6-[5-[(4-oxo-3H-phthalazin-1-yl)methyl]furan-3-yl]-1H-benzimidazol-2-yl]carbamate Chemical compound O=C1NN=C(C2=CC=CC=C12)CC1=CC(=CO1)C=1C=CC2=C(NC(=N2)NC(OC)=O)C=1 IHNRINCYMNAWAX-UHFFFAOYSA-N 0.000 description 1
- RHGBVZKXPWKLOJ-UHFFFAOYSA-N methyl N-[6-[5-[(5,8-difluoro-4-oxo-3H-phthalazin-1-yl)methyl]-2-fluorophenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC1=C2C(NN=C(C2=C(C=C1)F)CC=1C=CC(=C(C=1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)F)=O RHGBVZKXPWKLOJ-UHFFFAOYSA-N 0.000 description 1
- QCPWWTAKNUSHSZ-UHFFFAOYSA-N methyl N-[6-[5-[(6,7-difluoro-4-oxo-3H-phthalazin-1-yl)methyl]-2-fluorophenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC=1C=C2C(NN=C(C2=CC=1F)CC=1C=CC(=C(C=1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)F)=O QCPWWTAKNUSHSZ-UHFFFAOYSA-N 0.000 description 1
- FDEPTELWJKXFCO-UHFFFAOYSA-N methyl N-[6-[5-[(6,7-dimethoxy-4-oxo-3H-phthalazin-1-yl)methyl]-2-fluorophenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC=1C=C2C(NN=C(C2=CC=1OC)CC=1C=CC(=C(C=1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)F)=O FDEPTELWJKXFCO-UHFFFAOYSA-N 0.000 description 1
- RXFWYHAJEPHAHE-UHFFFAOYSA-N methyl N-[6-[5-[(6,8-dimethoxy-4-oxo-3H-phthalazin-1-yl)methyl]-2-fluorophenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound COC=1C=C2C(NN=C(C2=C(C=1)OC)CC=1C=CC(=C(C=1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)F)=O RXFWYHAJEPHAHE-UHFFFAOYSA-N 0.000 description 1
- FGKXNERJPPJOCC-UHFFFAOYSA-N methyl N-[6-[5-[(7-chloro-4-oxo-3H-phthalazin-1-yl)methyl]-2-fluorophenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound ClC1=CC=C2C(NN=C(C2=C1)CC=1C=CC(=C(C=1)C1=CC2=C(NC(=N2)NC(OC)=O)C=C1)F)=O FGKXNERJPPJOCC-UHFFFAOYSA-N 0.000 description 1
- BXGWVVVTJNVYCT-UHFFFAOYSA-N methyl N-[6-fluoro-5-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]phenyl]-1H-benzimidazol-2-yl]carbamate Chemical compound FC=1C(=CC2=C(NC(=N2)NC(OC)=O)C=1)C1=C(C=CC(=C1)CC1=NNC(C2=CC=CC=C12)=O)F BXGWVVVTJNVYCT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
- AQHIFTQCTDCFMD-UHFFFAOYSA-N methyl n,n'-bis(ethylcarbamoyl)carbamimidothioate Chemical compound CCNC(=O)N\C(SC)=N\C(=O)NCC AQHIFTQCTDCFMD-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 231100000782 microtubule inhibitor Toxicity 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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| US201662354449P | 2016-06-24 | 2016-06-24 | |
| US201662426095P | 2016-11-23 | 2016-11-23 | |
| PCT/US2017/039119 WO2017223516A1 (en) | 2016-06-24 | 2017-06-23 | Phthalazine derivatives as inhibitors of parp1, parp2 and/or tubulin useful for the treatment of cancer |
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| ES2964531T3 true ES2964531T3 (es) | 2024-04-08 |
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| EP3298005B1 (en) | 2015-05-21 | 2024-01-24 | The Regents of The University of California | Anti-cancer compounds |
| EP3383852A4 (en) * | 2015-11-30 | 2019-08-28 | Children's Medical Center Corporation | COMPOUNDS FOR THE TREATMENT OF PROLIFERATIVE DISEASES |
| EP3475272B1 (en) | 2016-06-24 | 2023-09-13 | The Regents of The University of California | Phthalazine derivatives as inhibitors of parp1, parp2 and/or tubulin useful for the treatment of cancer |
| JP7372253B2 (ja) * | 2018-04-05 | 2023-10-31 | ノビガ・リサーチ・エービー | 癌の治療における使用のためのチューブリン重合阻害剤とポリ（ａｄｐ－リボース）ポリメラーゼ（ｐａｒｐ）阻害剤との新規組合せ |
| CN112574122B (zh) * | 2019-09-27 | 2024-05-31 | 上海天慈国际药业有限公司 | 一种奥拉帕尼关键中间体的制备方法 |
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| US3401171A (en) | 1966-03-11 | 1968-09-10 | Smithkline Corp | 2-amidobenzimidazoles |
| SU1019810A1 (ru) | 1981-07-28 | 1991-04-07 | Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского | Метиловый эфир 5(6)-[1-(2Н)-фталазинонил-4]-1Н-бензимидазолил-2-карбаминовой кислоты, обладающий антигельминтной активностью |
| SU1218649A1 (ru) | 1984-09-19 | 1991-04-30 | Институт медицинской паразитологии и тропической медицины им.Е.И.Марциновского | Способ получени метилового эфира 5(6)-[1(2Н)-фталазинонил-4-]-1Н-бензимидазолил-2-карбаминовой кислоты формулы |
| JP2002502844A (ja) | 1998-02-03 | 2002-01-29 | ベーリンガー インゲルハイム ファルマ コマンディトゲゼルシャフト | ５員複素環縮合ベンゾ誘導体、その調製及び医薬品としてのそれらの使用 |
| KR20010101675A (ko) | 1999-01-26 | 2001-11-14 | 우에노 도시오 | 2ｈ-프탈라진-1-온 유도체 및 그 유도체를 유효 성분으로하는 약제 |
| DE19907813A1 (de) | 1999-02-24 | 2000-08-31 | Boehringer Ingelheim Pharma | Substituierte bicyclische Heterocyclen, deren Herstellung und deren Verwendung als Arzneimittel |
| HU228960B1 (hu) | 2000-10-30 | 2013-07-29 | Kudos Pharm Ltd | Ftalazinon-származékok |
| US7151102B2 (en) | 2000-10-30 | 2006-12-19 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| AR042956A1 (es) | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| EP1633724B1 (en) | 2003-03-12 | 2011-05-04 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| WO2005112932A2 (en) | 2004-05-07 | 2005-12-01 | Exelixis, Inc. | Raf modulators and methods of use |
| WO2006124874A2 (en) | 2005-05-12 | 2006-11-23 | Kalypsys, Inc. | Inhibitors of b-raf kinase |
| CN101291928A (zh) * | 2005-10-19 | 2008-10-22 | 库多斯药物有限公司 | 4-杂芳甲基取代的酞嗪酮衍生物 |
| UY30639A1 (es) | 2006-10-17 | 2008-05-31 | Kudos Pharm Ltd | Derivados sustituidos de 2h-ftalazin-1-ona, sus formas cristalinas, proceso de preparacion y aplicaciones |
| US20080280910A1 (en) * | 2007-03-22 | 2008-11-13 | Keith Allan Menear | Phthalazinone derivatives |
| JP5492183B2 (ja) * | 2008-03-27 | 2014-05-14 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｐａｒｐおよびチューブリン重合阻害剤としてのテトラヒドロフェナントリジノンおよびテトラヒドロシクロペンタキノリノン |
| CA3012137A1 (en) | 2010-01-29 | 2011-08-04 | Metanomics Gmbh | Means and methods for diagnosing heart failure in a subject |
| CN102372706A (zh) | 2010-08-09 | 2012-03-14 | 江苏恒瑞医药股份有限公司 | 酞嗪酮类衍生物、其制备方法及其在医药上的应用 |
| CA2875025C (en) | 2011-05-31 | 2021-08-03 | Newgen Therapeutics, Inc. | Tricyclic inhibitors of poly(adp-ribose)polymerase |
| KR101546743B1 (ko) * | 2012-01-16 | 2015-08-24 | 한국과학기술원 | 인돌 유도체 화합물, 이를 포함하는 Ａｂｌ 키나제 저해제 조성물 및 이상세포 성장 질환의 예방 및 치료용 약학 조성물 |
| AU2013368842B2 (en) * | 2012-12-31 | 2015-11-12 | Cadila Healthcare Limited | Substituted phthalazin-1 (2H)-one derivatives as selective inhibitors of poly (ADP-ribose) polymerase-1 |
| TWI527811B (zh) | 2013-05-09 | 2016-04-01 | 吉李德科學股份有限公司 | 作爲溴結構域抑制劑的苯並咪唑衍生物 |
| EP3475272B1 (en) * | 2016-06-24 | 2023-09-13 | The Regents of The University of California | Phthalazine derivatives as inhibitors of parp1, parp2 and/or tubulin useful for the treatment of cancer |
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- 2017-06-23 PT PT177371325T patent/PT3475272T/pt unknown
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- 2017-06-23 PL PL17737132.5T patent/PL3475272T3/pl unknown
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- 2017-06-23 WO PCT/US2017/039119 patent/WO2017223516A1/en not_active Ceased
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| ZA201808562B (en) | 2023-12-20 |
| JP7033588B2 (ja) | 2022-03-10 |
| US11072600B2 (en) | 2021-07-27 |
| EP3475272B1 (en) | 2023-09-13 |
| SG11201811393WA (en) | 2019-01-30 |
| WO2017223516A1 (en) | 2017-12-28 |
| IL263917B (en) | 2022-07-01 |
| BR112018076821A2 (pt) | 2019-04-02 |
| KR102494294B1 (ko) | 2023-01-31 |
| US10640493B2 (en) | 2020-05-05 |
| MX2018015893A (es) | 2019-08-01 |
| AU2017280334A1 (en) | 2019-01-17 |
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| HUE066216T2 (hu) | 2024-07-28 |
| JP2022037004A (ja) | 2022-03-08 |
| US20190352283A1 (en) | 2019-11-21 |
| US20220402894A1 (en) | 2022-12-22 |
| MX387726B (es) | 2025-03-18 |
| US12145925B2 (en) | 2024-11-19 |
| JP2019522681A (ja) | 2019-08-15 |
| ZA202301066B (en) | 2024-05-30 |
| CN109843874A (zh) | 2019-06-04 |
| CA3029004A1 (en) | 2017-12-28 |
| PL3475272T3 (pl) | 2024-04-29 |
| CN109843874B (zh) | 2022-05-27 |
| EP3475272A1 (en) | 2019-05-01 |
| PT3475272T (pt) | 2023-12-15 |
| US20190337928A1 (en) | 2019-11-07 |
| MX2021013641A (es) | 2022-01-06 |
| KR20190033534A (ko) | 2019-03-29 |
| AU2017280334B2 (en) | 2021-07-29 |
| AU2017280334C1 (en) | 2022-10-20 |
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