JP2015500212A5 - - Google Patents
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- Publication number
- JP2015500212A5 JP2015500212A5 JP2014543747A JP2014543747A JP2015500212A5 JP 2015500212 A5 JP2015500212 A5 JP 2015500212A5 JP 2014543747 A JP2014543747 A JP 2014543747A JP 2014543747 A JP2014543747 A JP 2014543747A JP 2015500212 A5 JP2015500212 A5 JP 2015500212A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- phthalazin
- fluoro
- piperazine
- phenoxy
- 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.)
- Granted
Links
- -1 chloro, fluoro, bromo, iodo Chemical group 0.000 claims 37
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- QNKQLZIDPHLSLX-UHFFFAOYSA-N 4-[3-[4-(1-aminocyclopropanecarbonyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CCN1C(=O)C1(N)CC1 QNKQLZIDPHLSLX-UHFFFAOYSA-N 0.000 claims 2
- TVWIYKCKCUIDFX-UHFFFAOYSA-N 4-[3-[4-(2,2-dimethylpropanoyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C(C)(C)C)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F TVWIYKCKCUIDFX-UHFFFAOYSA-N 0.000 claims 2
- IJSAVXZCXLCXRP-UHFFFAOYSA-N 4-[3-[4-(2-ethylbutanoyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C(CC)CC)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F IJSAVXZCXLCXRP-UHFFFAOYSA-N 0.000 claims 2
- PGOSXGKZYJLWAN-UHFFFAOYSA-N 4-[3-[4-[1-(dimethylamino)cyclobutanecarbonyl]piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CCN1C(=O)C1(N(C)C)CCC1 PGOSXGKZYJLWAN-UHFFFAOYSA-N 0.000 claims 2
- XDVCDFIVFSEAIF-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(2-nitrobenzoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CC1 XDVCDFIVFSEAIF-UHFFFAOYSA-N 0.000 claims 2
- BCFBHNMOIFYWBS-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(piperidine-1-carbonyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)N1CCCCC1 BCFBHNMOIFYWBS-UHFFFAOYSA-N 0.000 claims 2
- PHEJNKZPYQUXHV-UHFFFAOYSA-N 4-[4-fluoro-3-[4-[1-(methylamino)cyclobutanecarbonyl]piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CCN1C(=O)C1(NC)CCC1 PHEJNKZPYQUXHV-UHFFFAOYSA-N 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- TUWZZXGAUMSUOB-UHFFFAOYSA-N benzyl piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)OCC1=CC=CC=C1 TUWZZXGAUMSUOB-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- IDXLYJQVIRPLDQ-UHFFFAOYSA-N 2-[4-[2-fluoro-5-[(4-oxo-3h-phthalazin-1-yl)oxy]benzoyl]piperazine-1-carbonyl]benzonitrile Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1C#N IDXLYJQVIRPLDQ-UHFFFAOYSA-N 0.000 claims 1
- ZQTXNSWUYNTEBB-UHFFFAOYSA-N 2-[4-fluoro-3-[4-(2-methoxyacetyl)piperazine-1-carbonyl]phenoxy]phthalazin-1-one Chemical compound FC1=C(C=C(ON2C(C3=CC=CC=C3C=N2)=O)C=C1)C(=O)N1CCN(CC1)C(COC)=O ZQTXNSWUYNTEBB-UHFFFAOYSA-N 0.000 claims 1
- WAQCRMFLOXJEPH-UHFFFAOYSA-N 2-[4-fluoro-3-[4-(2-methyl-1,3-thiazole-4-carbonyl)piperazine-1-carbonyl]phenoxy]phthalazin-1-one Chemical compound FC1=C(C=C(ON2C(C3=CC=CC=C3C=N2)=O)C=C1)C(=O)N1CCN(CC1)C(=O)C=1N=C(SC=1)C WAQCRMFLOXJEPH-UHFFFAOYSA-N 0.000 claims 1
- YUNMCHVYEFMZIE-UHFFFAOYSA-N 2-[4-fluoro-3-[4-(5-methyl-1,2-oxazole-4-carbonyl)piperazine-1-carbonyl]phenoxy]phthalazin-1-one Chemical compound FC1=C(C=C(ON2C(C3=CC=CC=C3C=N2)=O)C=C1)C(=O)N1CCN(CC1)C(=O)C=1C=NOC=1C YUNMCHVYEFMZIE-UHFFFAOYSA-N 0.000 claims 1
- MUWUCBFFVDRMOQ-UHFFFAOYSA-N 2-phenoxyphthalazin-1-one Chemical compound O(C1=CC=CC=C1)N1C(C2=CC=CC=C2C=N1)=O MUWUCBFFVDRMOQ-UHFFFAOYSA-N 0.000 claims 1
- MCVFOGMCFOGZNE-UHFFFAOYSA-N 3-[4-[2-fluoro-5-[(4-oxo-3h-phthalazin-1-yl)oxy]benzoyl]piperazine-1-carbonyl]benzonitrile Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CC(C#N)=C1 MCVFOGMCFOGZNE-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- OXZAGDCIHSWPSQ-UHFFFAOYSA-N 4-[3-(4-acetylpiperazine-1-carbonyl)-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F OXZAGDCIHSWPSQ-UHFFFAOYSA-N 0.000 claims 1
- RSJQQCASEGSQDI-UHFFFAOYSA-N 4-[3-(4-benzoylpiperazine-1-carbonyl)-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 RSJQQCASEGSQDI-UHFFFAOYSA-N 0.000 claims 1
- LITWQHBVWSJKPY-UHFFFAOYSA-N 4-[3-(4-benzoylpiperazine-1-carbonyl)-4-fluorophenoxy]-5-chloro-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=C(Cl)C=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 LITWQHBVWSJKPY-UHFFFAOYSA-N 0.000 claims 1
- FEOUWECRHACLNJ-UHFFFAOYSA-N 4-[3-(4-benzoylpiperazine-1-carbonyl)-4-fluorophenoxy]-5-nitro-2h-phthalazin-1-one Chemical compound [O-][N+](=O)C1=CC=CC(C(NN=2)=O)=C1C=2OC(C=1)=CC=C(F)C=1C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 FEOUWECRHACLNJ-UHFFFAOYSA-N 0.000 claims 1
- QGDDDEOCEHOXKJ-UHFFFAOYSA-N 4-[3-(4-tert-butylpiperazine-1-carbonyl)-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(C)(C)C)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F QGDDDEOCEHOXKJ-UHFFFAOYSA-N 0.000 claims 1
- ZJSQULBIGVRLSV-UHFFFAOYSA-N 4-[3-[4-(1-aminocyclobutanecarbonyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CCN1C(=O)C1(N)CCC1 ZJSQULBIGVRLSV-UHFFFAOYSA-N 0.000 claims 1
- UFVPUCUXFUEIDV-UHFFFAOYSA-N 4-[3-[4-(2-cyclopentylacetyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)CC1CCCC1 UFVPUCUXFUEIDV-UHFFFAOYSA-N 0.000 claims 1
- RWQBQENZPPMPPI-UHFFFAOYSA-N 4-[3-[4-(2-cyclopropylacetyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)CC1CC1 RWQBQENZPPMPPI-UHFFFAOYSA-N 0.000 claims 1
- SKGRPBVRUGLOSF-UHFFFAOYSA-N 4-[3-[4-(2-ethoxyacetyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)COCC)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F SKGRPBVRUGLOSF-UHFFFAOYSA-N 0.000 claims 1
- QJQDIQKTDSBMOB-UHFFFAOYSA-N 4-[3-[4-(4,4-difluorocyclohexanecarbonyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2H-phthalazin-1-one Chemical compound Fc1ccc(Oc2n[nH]c(=O)c3ccccc23)cc1C(=O)N1CCN(CC1)C(=O)C1CCC(F)(F)CC1 QJQDIQKTDSBMOB-UHFFFAOYSA-N 0.000 claims 1
- SSVOKXAGBNLVLQ-UHFFFAOYSA-N 4-[3-[4-(4,4-difluoropiperidine-1-carbonyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)N1CCC(F)(F)CC1 SSVOKXAGBNLVLQ-UHFFFAOYSA-N 0.000 claims 1
- IWLJMCXJVVOBBW-UHFFFAOYSA-N 4-[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1CC1 IWLJMCXJVVOBBW-UHFFFAOYSA-N 0.000 claims 1
- DZWVGXKLZPKLKS-UHFFFAOYSA-N 4-[3-[4-[1-(dimethylamino)cyclopropanecarbonyl]piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CCN1C(=O)C1(N(C)C)CC1 DZWVGXKLZPKLKS-UHFFFAOYSA-N 0.000 claims 1
- YGXNDLBTQGMPOV-UHFFFAOYSA-N 4-[3-[4-[3-(dimethylamino)benzoyl]piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound CN(C)C1=CC=CC(C(=O)N2CCN(CC2)C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)=C1 YGXNDLBTQGMPOV-UHFFFAOYSA-N 0.000 claims 1
- NDEWUMPGCMVIOL-UHFFFAOYSA-N 4-[3-[4-[4-(dimethylamino)benzoyl]piperazine-1-carbonyl]-4-fluorophenoxy]-2h-phthalazin-1-one Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CC1 NDEWUMPGCMVIOL-UHFFFAOYSA-N 0.000 claims 1
- ZSHQAWHQMUOABD-UHFFFAOYSA-N 4-[4-[2-fluoro-5-[(4-oxo-3h-phthalazin-1-yl)oxy]benzoyl]piperazine-1-carbonyl]benzonitrile Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 ZSHQAWHQMUOABD-UHFFFAOYSA-N 0.000 claims 1
- YJMHEEGVFDLUFN-UHFFFAOYSA-N 4-[4-fluoro-3-(4-methylpiperazine-1-carbonyl)phenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F YJMHEEGVFDLUFN-UHFFFAOYSA-N 0.000 claims 1
- PXYIFDVNUHAHEH-UHFFFAOYSA-N 4-[4-fluoro-3-(4-prop-2-enoylpiperazine-1-carbonyl)phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N1CCN(C(=O)C=C)CC1 PXYIFDVNUHAHEH-UHFFFAOYSA-N 0.000 claims 1
- PWJANPHHJVLKFB-UHFFFAOYSA-N 4-[4-fluoro-3-(piperazine-1-carbonyl)phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N1CCNCC1 PWJANPHHJVLKFB-UHFFFAOYSA-N 0.000 claims 1
- LDYIPKQZQAIRTD-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(1,3-thiazole-4-carbonyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1=CSC=N1 LDYIPKQZQAIRTD-UHFFFAOYSA-N 0.000 claims 1
- XMXROHYJWCZPPL-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(2,2,2-trifluoroacetyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N1CCN(C(=O)C(F)(F)F)CC1 XMXROHYJWCZPPL-UHFFFAOYSA-N 0.000 claims 1
- NGRBLFZCOQNFEU-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(2-hydroxyethyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1CN(CCO)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F NGRBLFZCOQNFEU-UHFFFAOYSA-N 0.000 claims 1
- VODHOJPJFWVPHK-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(2-hydroxypropanoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C(O)C)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F VODHOJPJFWVPHK-UHFFFAOYSA-N 0.000 claims 1
- MVYFDNKSMQLYJP-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC(OC=2C3=CC=CC=C3C(=O)NN=2)=CC=C1F MVYFDNKSMQLYJP-UHFFFAOYSA-N 0.000 claims 1
- ZNXUITMOKZZDLO-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(3,3,3-trifluoropropanoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N1CCN(C(=O)CC(F)(F)F)CC1 ZNXUITMOKZZDLO-UHFFFAOYSA-N 0.000 claims 1
- DSBUUJLGVNOCFI-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(3-nitrobenzoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)N2CCN(CC2)C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)=C1 DSBUUJLGVNOCFI-UHFFFAOYSA-N 0.000 claims 1
- GXQGLXCMWVOQCQ-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-fluorobenzoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1=CC(F)=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CC1 GXQGLXCMWVOQCQ-UHFFFAOYSA-N 0.000 claims 1
- ZVASRUFHGODWNV-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-fluorobenzoyl)piperazine-1-carbonyl]phenoxy]-5-nitro-2h-phthalazin-1-one Chemical compound [O-][N+](=O)C1=CC=CC(C(NN=2)=O)=C1C=2OC(C=1)=CC=C(F)C=1C(=O)N(CC1)CCN1C(=O)C1=CC=C(F)C=C1 ZVASRUFHGODWNV-UHFFFAOYSA-N 0.000 claims 1
- JYULXMCNNAMJSH-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-fluorophenyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1=CC(F)=CC=C1N1CCN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CC1 JYULXMCNNAMJSH-UHFFFAOYSA-N 0.000 claims 1
- STZWABPGYDHYHM-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-fluorophenyl)piperazine-1-carbonyl]phenoxy]-5-nitro-2h-phthalazin-1-one Chemical compound [O-][N+](=O)C1=CC=CC(C(NN=2)=O)=C1C=2OC(C=1)=CC=C(F)C=1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 STZWABPGYDHYHM-UHFFFAOYSA-N 0.000 claims 1
- JTZDUKTYNORBQE-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-nitrobenzoyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)CC1 JTZDUKTYNORBQE-UHFFFAOYSA-N 0.000 claims 1
- MYMOJTQDIFCGBT-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-nitrobenzoyl)piperazine-1-carbonyl]phenoxy]-5-nitro-2h-phthalazin-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)N1CCN(C(=O)C=2C(=CC=C(OC=3C4=C([N+]([O-])=O)C=CC=C4C(=O)NN=3)C=2)F)CC1 MYMOJTQDIFCGBT-UHFFFAOYSA-N 0.000 claims 1
- AWJBJIJKZWTVPH-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(4-oxocyclohexanecarbonyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound FC1=CC=C(OC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(CC1)CCN1C(=O)C1CCC(=O)CC1 AWJBJIJKZWTVPH-UHFFFAOYSA-N 0.000 claims 1
- DSBVAGDGCREERF-UHFFFAOYSA-N 4-[4-fluoro-3-[4-(5-methyl-1,2-oxazole-3-carbonyl)piperazine-1-carbonyl]phenoxy]-2h-phthalazin-1-one Chemical compound O1C(C)=CC(C(=O)N2CCN(CC2)C(=O)C=2C(=CC=C(OC=3C4=CC=CC=C4C(=O)NN=3)C=2)F)=N1 DSBVAGDGCREERF-UHFFFAOYSA-N 0.000 claims 1
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| CN105017140B (zh) * | 2014-04-28 | 2017-12-29 | 复旦大学 | 邻氨基苯甲酰胺化合物及其制备方法和用途 |
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| CN105777651A (zh) * | 2015-01-13 | 2016-07-20 | 江苏豪森药业集团有限公司 | 聚腺苷酸二磷酸核糖转移酶抑制剂的晶型及其制备方法和医药用途 |
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| US10583137B2 (en) | 2015-12-02 | 2020-03-10 | The Scripps Research Institute | Triazole DAGLα inhibitors |
| CN107955001A (zh) * | 2016-10-14 | 2018-04-24 | 上海汇伦生命科技有限公司 | 抗肿瘤杂环并咪唑类化合物的药用盐 |
| CN106946792B (zh) * | 2017-03-29 | 2019-07-26 | 深圳市坤健创新药物研究院 | 一种酞嗪酮的异羟肟酸衍生物及其制备方法与应用 |
| US10927105B1 (en) | 2017-05-23 | 2021-02-23 | Lundbeck La Jolla Research Center, Inc. | Pyrazole MAGL inhibitors |
| AU2018271876B2 (en) | 2017-05-23 | 2021-10-21 | H. Lundbeck A/S. | Pyrazole MAGL inhibitors |
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| CN107082764B (zh) * | 2017-05-23 | 2018-11-02 | 上海锐聚恩新药研发有限公司 | 一类多羟基酞嗪酮化合物、其制备方法及应用 |
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| EP1633724B1 (en) * | 2003-03-12 | 2011-05-04 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0305681D0 (en) | 2003-03-12 | 2003-04-16 | Kudos Pharm Ltd | Phthalazinone derivatives |
| HU227948B1 (en) | 2003-04-30 | 2012-07-30 | Pecsi Tudomanyegyetem | Quinazoline derivatives and their use for the preparation of pharmaceutical compositions inhibiting parp enzyme |
| WO2005023246A1 (en) | 2003-09-04 | 2005-03-17 | Aventis Pharmaceuticals Inc. | Substituted indoles as inhibitors of poly (adp-ribose) polymerase (parp) |
| CN1905864B (zh) | 2003-12-01 | 2011-04-06 | 库多斯药物有限公司 | 用于治疗癌症的dna损伤修复抑制剂 |
| EP1684736B1 (en) | 2003-12-01 | 2011-08-24 | Kudos Pharmaceuticals Limited | Dna damage repair inhibitors for treatment of cancer |
| BRPI0416532A (pt) | 2003-12-05 | 2007-01-09 | Janssen Pharmaceutica Nv | 2-quinolinonas e 2-quinoxalinonas substituìdas por 6 como inibidores da poli(adp-ribose) polimerase |
| WO2006003148A1 (en) | 2004-06-30 | 2006-01-12 | Janssen Pharmaceutica N.V. | Quinazolinedione derivatives as parp inhibitors |
| GB0419072D0 (en) * | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
| MX2007002318A (es) | 2004-08-26 | 2007-04-17 | Kudos Pharm Ltd | Derivados de ftalazinona substituidos con 4-heteroarilmetilo. |
| KR100876520B1 (ko) | 2004-09-22 | 2008-12-31 | 화이자 인코포레이티드 | 폴리(ａｄｐ-리보오스) 폴리머라제 억제제의 제조 방법 |
| GB0521373D0 (en) | 2005-10-20 | 2005-11-30 | Kudos Pharm Ltd | Pthalazinone derivatives |
| AU2007266840B2 (en) | 2006-05-31 | 2012-09-20 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Pyrrolo[1,2-A]pyrazin-1(2H)-one and pyrrolo[1,2-D][1,2,4]triazin-1(2H)-one derivatives as inhibitors of poly(ADP-ribose)polymerase(PARP) |
| GB0615809D0 (en) | 2006-08-09 | 2006-09-20 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| AR070221A1 (es) * | 2008-01-23 | 2010-03-25 | Astrazeneca Ab | Derivados de ftalazinona inhibidores de polimerasas, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar tumores cancerigenos,lesiones isquemicas y otras enfermedades asociadas. |
| WO2011130478A1 (en) * | 2010-04-16 | 2011-10-20 | Abbott Laboratories | Phthalazin-(2h)-one inhibitors of kinases |
| WO2012014221A1 (en) | 2010-07-27 | 2012-02-02 | Cadila Healthcare Limited | Substituted 4-(4-fluoro-3-(piperazine-1- carbonyl)benzyl)phthalazin-1(2h)-one derivatives as poly (adp-ribose) polymerase- 1 inhibitors |
| CN102485721B (zh) | 2010-12-03 | 2015-12-09 | 曹亚 | 取代的2,3-二氮杂萘酮化合物及其用途 |
| CN103130723B (zh) * | 2011-11-30 | 2015-01-14 | 成都地奥制药集团有限公司 | 一种多聚(adp-核糖)聚合酶抑制剂 |
| CN102898377B (zh) * | 2012-02-14 | 2016-01-20 | 南京圣和药业股份有限公司 | 一类酞嗪酮衍生物及其用途 |
-
2012
- 2012-11-30 CN CN201210504537.2A patent/CN103130723B/zh active Active
- 2012-12-03 EP EP12852659.7A patent/EP2799435B1/en active Active
- 2012-12-03 JP JP2014543747A patent/JP5820081B2/ja active Active
- 2012-12-03 US US14/361,698 patent/US9187430B2/en active Active
- 2012-12-03 WO PCT/CN2012/001611 patent/WO2013078771A1/zh not_active Ceased
- 2012-12-03 CA CA2857405A patent/CA2857405C/en active Active
-
2015
- 2015-08-13 US US14/826,181 patent/US9718787B2/en active Active
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