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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| US10583137B2 (en) | 2015-12-02 | 2020-03-10 | The Scripps Research Institute | Triazole DAGLα inhibitors |
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| KR102798358B1 (ko) | 2018-05-24 | 2025-04-23 | 노파르티스 아게 | 자동 약물 전달 디바이스 |
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| US10793554B2 (en) | 2018-10-29 | 2020-10-06 | Forma Therapeutics, Inc. | Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone |
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2012
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- 2012-12-03 JP JP2014543747A patent/JP5820081B2/ja active Active
- 2012-12-03 CA CA2857405A patent/CA2857405C/en active Active
- 2012-12-03 WO PCT/CN2012/001611 patent/WO2013078771A1/zh not_active Ceased
- 2012-12-03 EP EP12852659.7A patent/EP2799435B1/en active Active
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2015
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