JP2013518892A5 - - Google Patents
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- JP2013518892A5 JP2013518892A5 JP2012552070A JP2012552070A JP2013518892A5 JP 2013518892 A5 JP2013518892 A5 JP 2013518892A5 JP 2012552070 A JP2012552070 A JP 2012552070A JP 2012552070 A JP2012552070 A JP 2012552070A JP 2013518892 A5 JP2013518892 A5 JP 2013518892A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrido
- dihydro
- methyl
- phthalazin
- 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
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- 239000008194 pharmaceutical composition Substances 0.000 claims 48
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 13
- 229910052794 bromium Inorganic materials 0.000 claims 13
- 229910052801 chlorine Inorganic materials 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 229910052740 iodine Inorganic materials 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 claims 9
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 claims 8
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 claims 8
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 230000007812 deficiency Effects 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000006354 carbonyl alkylene group Chemical group 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 150000003852 triazoles Chemical class 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 206010041067 Small cell lung cancer Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 230000005782 double-strand break Effects 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 3
- 125000005367 heteroarylalkylthio group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims 3
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 3
- 230000006801 homologous recombination Effects 0.000 claims 3
- 238000002744 homologous recombination Methods 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 206010027191 meningioma Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- WGZMUTVUDVLUJL-UHFFFAOYSA-N 12-phenyl-11-pyridin-2-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C1=CC=CC=N1 WGZMUTVUDVLUJL-UHFFFAOYSA-N 0.000 claims 2
- VZYOBZPMHSMQGJ-UHFFFAOYSA-N 12-phenyl-11-pyridin-4-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2C=CC=CC=2)C1C1=CC=NC=C1 VZYOBZPMHSMQGJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- HWGQMRYQVZSGDQ-UHFFFAOYSA-N 7-fluoro-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 HWGQMRYQVZSGDQ-UHFFFAOYSA-N 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 206010014733 Endometrial cancer Diseases 0.000 claims 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 201000008395 adenosquamous carcinoma Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 230000002950 deficient Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 201000010893 malignant breast melanoma Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- SOMLCVOFFCJGNU-IRXDYDNUSA-N (11R,12S)-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SOMLCVOFFCJGNU-IRXDYDNUSA-N 0.000 claims 1
- VGCYLQAHCSEGLE-HOTGVXAUSA-N (11R,12S)-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VGCYLQAHCSEGLE-HOTGVXAUSA-N 0.000 claims 1
- UMTZOWPWZLHANK-UPVQGACJSA-N (11R,12S)-11-[4-(azetidin-1-ylmethyl)phenyl]-12-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1[C@@H]([C@@H](N1)C=2C=CC(CN3CCC3)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 UMTZOWPWZLHANK-UPVQGACJSA-N 0.000 claims 1
- OWJGUHRNNJVRHR-OALUTQOASA-N (11R,12S)-11-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1[C@H](N1)[C@H](C=2N(N=CN=2)C)C2=NNC(=O)C3=C2C1=CC(F)=C3 OWJGUHRNNJVRHR-OALUTQOASA-N 0.000 claims 1
- LJXPYHXSPQXFKB-IRXDYDNUSA-N (11R,12S)-7-fluoro-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 LJXPYHXSPQXFKB-IRXDYDNUSA-N 0.000 claims 1
- HWGQMRYQVZSGDQ-HOTGVXAUSA-N (11R,12S)-7-fluoro-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@@H]([C@@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 HWGQMRYQVZSGDQ-HOTGVXAUSA-N 0.000 claims 1
- JMRVJHACGJMVJK-IRXDYDNUSA-N (11R,12S)-7-fluoro-12-(1-methylimidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@@H]([C@@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 JMRVJHACGJMVJK-IRXDYDNUSA-N 0.000 claims 1
- RJXIQUMBMLJTTJ-HOTGVXAUSA-N (11R,12S)-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@@H]([C@@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 RJXIQUMBMLJTTJ-HOTGVXAUSA-N 0.000 claims 1
- SOMLCVOFFCJGNU-IAGOWNOFSA-N (11S,12R)-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@H]([C@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 SOMLCVOFFCJGNU-IAGOWNOFSA-N 0.000 claims 1
- VGCYLQAHCSEGLE-HZPDHXFCSA-N (11S,12R)-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@H]([C@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 VGCYLQAHCSEGLE-HZPDHXFCSA-N 0.000 claims 1
- UMTZOWPWZLHANK-ISKFKSNPSA-N (11S,12R)-11-[4-(azetidin-1-ylmethyl)phenyl]-12-(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1[C@H]([C@H](N1)C=2C=CC(CN3CCC3)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 UMTZOWPWZLHANK-ISKFKSNPSA-N 0.000 claims 1
- OWJGUHRNNJVRHR-RTBURBONSA-N (11S,12R)-11-[4-[(dimethylamino)methyl]phenyl]-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1[C@@H](N1)[C@@H](C=2N(N=CN=2)C)C2=NNC(=O)C3=C2C1=CC(F)=C3 OWJGUHRNNJVRHR-RTBURBONSA-N 0.000 claims 1
- LJXPYHXSPQXFKB-IAGOWNOFSA-N (11S,12R)-7-fluoro-11-(4-fluorophenyl)-12-(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@H]([C@H](N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 LJXPYHXSPQXFKB-IAGOWNOFSA-N 0.000 claims 1
- JMRVJHACGJMVJK-IAGOWNOFSA-N (11S,12R)-7-fluoro-12-(1-methylimidazol-2-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1[C@H]([C@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 JMRVJHACGJMVJK-IAGOWNOFSA-N 0.000 claims 1
- RJXIQUMBMLJTTJ-HZPDHXFCSA-N (11S,12R)-7-fluoro-12-(2-methyl-1,2,4-triazol-3-yl)-11-phenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1[C@H]([C@H](N1)C=2C=CC=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 RJXIQUMBMLJTTJ-HZPDHXFCSA-N 0.000 claims 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 1
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 1
- HLMLLKFCRNXDCU-UHFFFAOYSA-N 10-ethyl-11,12-diphenyl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C=12C3=NNC(=O)C2=CC=CC=1N(CC)C(C=1C=CC=CC=1)C3C1=CC=CC=C1 HLMLLKFCRNXDCU-UHFFFAOYSA-N 0.000 claims 1
- OVSNPTZKZPHLSC-UHFFFAOYSA-N 11,12-bis(1-methylimidazol-2-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1C=CN=C1C(N1)C(C=2N(C=CN=2)C)C2=NNC(=O)C3=C2C1=CC=C3 OVSNPTZKZPHLSC-UHFFFAOYSA-N 0.000 claims 1
- XCTHABQHPYGJGY-UHFFFAOYSA-N 11,12-bis(4-fluorophenyl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(F)=CC=C1C(N1)C(C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 XCTHABQHPYGJGY-UHFFFAOYSA-N 0.000 claims 1
- ALFPJVGIQSAMIR-UHFFFAOYSA-N 11,12-bis[3-(methylaminomethyl)phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CNCC1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=C(CNC)C=CC=2)=C1 ALFPJVGIQSAMIR-UHFFFAOYSA-N 0.000 claims 1
- HGZOJDBSTWKIKE-UHFFFAOYSA-N 11,12-bis[3-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN(C)CC1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=C(CN(C)C)C=CC=2)=C1 HGZOJDBSTWKIKE-UHFFFAOYSA-N 0.000 claims 1
- UWMAULNVNHANQX-UHFFFAOYSA-N 11,12-bis[3-[4-(2-methylpropanoyl)piperazine-1-carbonyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1CN(C(=O)C(C)C)CCN1C(=O)C1=CC=CC(C2C(C=3C4=C(C(NN=3)=O)C=CC=C4N2)C=2C=C(C=CC=2)C(=O)N2CCN(CC2)C(=O)C(C)C)=C1 UWMAULNVNHANQX-UHFFFAOYSA-N 0.000 claims 1
- UMCZUCYEMNNRPS-UHFFFAOYSA-N 11,12-bis[4-[(dimethylamino)methyl]phenyl]-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC=C3 UMCZUCYEMNNRPS-UHFFFAOYSA-N 0.000 claims 1
- PVKRHCUUSZTERO-UHFFFAOYSA-N 11,12-bis[4-[(dimethylamino)methyl]phenyl]-7-fluoro-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound C1=CC(CN(C)C)=CC=C1C(N1)C(C=2C=CC(CN(C)C)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 PVKRHCUUSZTERO-UHFFFAOYSA-N 0.000 claims 1
- ULPMFQRNYGWKAD-UHFFFAOYSA-N 11,12-dipyridin-2-yl-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound N1C(C2=3)=CC=CC=3C(=O)NN=C2C(C=2N=CC=CC=2)C1C1=CC=CC=N1 ULPMFQRNYGWKAD-UHFFFAOYSA-N 0.000 claims 1
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| CN104478875B (zh) | 2008-08-06 | 2017-04-12 | 麦迪韦逊科技有限公司 | 聚(adp‑核糖)聚合酶(parp)的二氢吡啶并酞嗪酮抑制剂 |
| EP2531033A4 (en) | 2010-02-03 | 2013-07-31 | Biomarin Pharm Inc | POLY (ADP-RIBOSE) POLYMERASE (PARP) DIHYDROPYRIDOPHTHALAZINE HEMMER FOR USE IN THE TREATMENT OF PTEN-LACK ASSOCIATED DISEASES |
| KR101826652B1 (ko) * | 2010-02-08 | 2018-02-07 | 메디베이션 테크놀로지즈, 인크. | 디히드로피리도프탈라지논 유도체의 합성 방법 |
| KR20190120458A (ko) | 2010-10-21 | 2019-10-23 | 메디베이션 테크놀로지즈 엘엘씨 | 결정질의 (8s,9r)-5-플루오로-8-(4-플루오로페닐)-9-(1-메틸-1h-1,2,4-트리아졸-5-일)-8,9-디하이드로-2h-피리도[4,3,2-de]프탈라진-3(7h)-온 토실레이트 염 |
| WO2013028495A1 (en) * | 2011-08-19 | 2013-02-28 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly (adp-ribose) polymerase (parp) for the treatment of multiple myeloma |
| EP3265560B1 (en) | 2015-03-02 | 2021-12-08 | Sinai Health System | Homologous recombination factors |
| CN104945406B (zh) * | 2015-05-25 | 2017-10-10 | 苏州康润医药有限公司 | 氮杂非那烯‑3‑酮的衍生物、其制备方法及其作为parp抑制剂的应用 |
| US9957267B2 (en) | 2015-07-01 | 2018-05-01 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| SG11201803462PA (en) * | 2015-10-26 | 2018-05-30 | Medivation Tech Llc | Treatment of small cell lung cancer with a parp inhibitor |
| CN110382468B (zh) * | 2017-02-25 | 2023-03-24 | 苏州开拓药业股份有限公司 | 具有聚(adp-核糖)聚合酶(parp)抑制活性的二氢吡啶并二氮杂萘酮化合物及其用途 |
| EP3658560A4 (en) | 2017-07-25 | 2021-01-06 | Crinetics Pharmaceuticals, Inc. | SOMATOSTAT IN MODULATORS AND USES THEREOF |
| CA3078806A1 (en) | 2017-10-13 | 2019-04-18 | Merck Patent Gmbh | Combination of a parp inhibitor and a pd-1 axis binding antagonist |
| TW201938165A (zh) | 2017-12-18 | 2019-10-01 | 美商輝瑞股份有限公司 | 治療癌症的方法及組合療法 |
| US20210355223A1 (en) | 2018-11-05 | 2021-11-18 | Pfizer Inc. | Combinations for Treating Cancer |
| US20220388980A1 (en) * | 2019-10-01 | 2022-12-08 | Drexel University | Quinoline inhibitors of rad52 and methods of use |
| EP4118105A2 (en) | 2020-03-09 | 2023-01-18 | Pfizer Inc. | Cd80-fc fusion protein and uses thereof |
| JP7796032B2 (ja) * | 2020-03-11 | 2026-01-08 | パーデュー・リサーチ・ファウンデーション | 免疫調節活性を持つ化合物およびその治療的使用 |
| AU2021318572A1 (en) * | 2020-07-31 | 2023-02-16 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Indolo heptamyl oxime analog crystal as PARP inhibitor and method for preparing same |
| US20230414522A1 (en) | 2020-11-13 | 2023-12-28 | Pfizer Inc. | Talazoparib soft gelatin capsule dosage form |
| EP4256088A1 (en) | 2020-12-07 | 2023-10-11 | Pfizer Inc. | Methods of identifying a tumor that is sensitive to treatment with talazoparib and methods of treatment thereof |
| WO2022200982A1 (en) | 2021-03-24 | 2022-09-29 | Pfizer Inc. | Combination of talazoparib and an anti-androgen for the treatment of ddr gene mutated metastatic castration-sensitive prostate cancer |
| WO2023131894A1 (en) | 2022-01-08 | 2023-07-13 | Pfizer Inc. | Genomic loss of heterozygosity as a predictive biomarker for treatment with talazoparib and methods of treatment thereof |
| TWI883565B (zh) | 2022-10-02 | 2025-05-11 | 美商輝瑞大藥廠 | 用於治療轉移性去勢抵抗性前列腺癌之他拉唑帕尼及恩雜魯胺之組合 |
| TW202425976A (zh) | 2022-12-17 | 2024-07-01 | 美商輝瑞大藥廠 | 用於治療轉移性去勢抵抗性前列腺癌之他拉唑帕尼及恩雜魯胺之組合 |
| TW202600137A (zh) | 2024-04-04 | 2026-01-01 | 美商輝瑞股份有限公司 | 於使用ｐａｒｐ抑制劑的治療作為預測性生物標記之ｔｍｐｒｓｓ２－ｅｒｇ和ｒｂｉ及使用ｐａｒｐ抑制劑之治療方法 |
| WO2026078615A1 (en) | 2024-10-09 | 2026-04-16 | Pfizer Inc. | Combination of talazoparib and enzalutamide in the treatment of metastatic castration-resistant prostate cancer |
| WO2026078619A1 (en) | 2024-10-09 | 2026-04-16 | Pfizer Inc. | Combination of talazoparib and enzalutamide in the treatment of metastatic castration-resistant prostate cancer |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415504A (en) | 1981-09-21 | 1983-11-15 | Tanabe Seiyaku Co., Ltd. | p-Hydroxyphenylglycine.α-phenylethanesulfonate, process for production thereof and utilization thereof in resolution of p-hydroxyphenylglycine |
| JPS58225065A (ja) | 1982-06-21 | 1983-12-27 | Nippon Shinyaku Co Ltd | ２−キノロン誘導体 |
| US5328905A (en) | 1987-07-20 | 1994-07-12 | Duphar International Research B.V. | 8,9-anellated-1,2,3,4-tetrahydro-β-carboline derivatives |
| GB9505538D0 (en) | 1995-03-18 | 1995-05-03 | Ciba Geigy Ag | New compounds |
| ID19155A (id) | 1996-12-13 | 1998-06-18 | Tanabe Seiyaku Co | Turunan-turunan piridin, pembuatannya dan intermediet untuk pembuatannya |
| DE19727410A1 (de) | 1997-06-27 | 1999-01-07 | Hoechst Schering Agrevo Gmbh | 3-(5-Tetrazolylcarbonyl)-2-chinolone und diese enthaltende nutzpflanzenschützende Mittel |
| US6514983B1 (en) | 1997-09-03 | 2003-02-04 | Guilford Pharmaceuticals Inc. | Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage |
| TW430656B (en) | 1997-12-03 | 2001-04-21 | Dainippon Ink & Chemicals | Quinolinone derivative, method for preparing the same, and anti-allergic agent |
| AU9298798A (en) | 1998-05-15 | 1999-12-06 | Guilford Pharmaceuticals Inc. | Fused tricyclic compounds which inhibit parp activity |
| DE19921567A1 (de) | 1999-05-11 | 2000-11-16 | Basf Ag | Verwendung von Phthalazine-Derivaten |
| JP2001302669A (ja) * | 2000-04-18 | 2001-10-31 | Meiji Seika Kaisha Ltd | 三環性フタラジノン誘導体 |
| JP2002284699A (ja) | 2001-03-28 | 2002-10-03 | Sumitomo Pharmaceut Co Ltd | 視細胞変性疾患治療剤 |
| AR036081A1 (es) | 2001-06-07 | 2004-08-11 | Smithkline Beecham Corp | Compuesto de 1,2-dihidroquinolina, su uso para preparar una composicion farmaceutica, metodos para prepararlo y compuestos del acido 2-aminobenzoico n-alquilado de utilidad como intermediarios en dichos metodos |
| SE0102315D0 (sv) | 2001-06-28 | 2001-06-28 | Astrazeneca Ab | Compounds |
| AU2003211381B9 (en) | 2002-02-19 | 2009-07-30 | Ono Pharmaceutical Co., Ltd. | Fused pyridazine derivative compounds and drugs containing the compounds as the active ingredient |
| EP1340819A1 (en) | 2002-02-28 | 2003-09-03 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Microsatellite markers |
| GB0221443D0 (en) | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
| EP1400244A1 (en) | 2002-09-17 | 2004-03-24 | Warner-Lambert Company LLC | New spirocondensed quinazolinones and their use as phosphodiesterase inhibitors |
| JPWO2004043959A1 (ja) | 2002-11-12 | 2006-03-09 | 持田製薬株式会社 | 新規ｐａｒｐ阻害剤 |
| PL1633724T3 (pl) | 2003-03-12 | 2011-10-31 | Kudos Pharm Ltd | Pochodne ftalazynonu |
| ES2396334T3 (es) | 2003-05-28 | 2013-02-20 | Eisai Inc. | Compuestos, métodos y composiciones farmacéuticas para la inhibición de PARP |
| WO2005080356A1 (en) | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
| GB0612971D0 (en) * | 2006-06-30 | 2006-08-09 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| CA2684105C (en) | 2007-05-03 | 2011-09-06 | Pfizer Limited | Pyridine derivatives |
| WO2009024190A1 (en) | 2007-08-22 | 2009-02-26 | 4Sc Ag | Indolopyridines as inhibitors of the kinesin spindle protein (eg5 ) |
| WO2009099736A2 (en) | 2008-02-06 | 2009-08-13 | Lead Therapeutics, Inc. | Benzoxazole carboxamide inhibitors of poly(adp-ribose)polymerase (parp) |
| CN104478875B (zh) | 2008-08-06 | 2017-04-12 | 麦迪韦逊科技有限公司 | 聚(adp‑核糖)聚合酶(parp)的二氢吡啶并酞嗪酮抑制剂 |
| KR20110053424A (ko) | 2008-08-12 | 2011-05-23 | 베링거 인겔하임 인터내셔날 게엠베하 | 사이클로알킬-치환된 피페라진 화합물의 제조 방법 |
| EP2531033A4 (en) | 2010-02-03 | 2013-07-31 | Biomarin Pharm Inc | POLY (ADP-RIBOSE) POLYMERASE (PARP) DIHYDROPYRIDOPHTHALAZINE HEMMER FOR USE IN THE TREATMENT OF PTEN-LACK ASSOCIATED DISEASES |
| US20110190266A1 (en) | 2010-02-04 | 2011-08-04 | Daniel Chu | 5,6,6a,7,8,9-HEXAHYDRO-2H-PYRIDOPHTHALAZINONE INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE (PARP) |
| KR101826652B1 (ko) | 2010-02-08 | 2018-02-07 | 메디베이션 테크놀로지즈, 인크. | 디히드로피리도프탈라지논 유도체의 합성 방법 |
| WO2011130661A1 (en) | 2010-04-16 | 2011-10-20 | Biomarin Pharmaceutical Inc. | Methods of using dihydropyridophthalazinone inhibitors of poly (adp-ribose)polymerase (parp) |
| WO2011140009A1 (en) | 2010-05-04 | 2011-11-10 | Biomarin Pharmaceutical Inc. | Methods of using semi-synthetic glycopeptides as antibacterial agents |
| KR20190120458A (ko) | 2010-10-21 | 2019-10-23 | 메디베이션 테크놀로지즈 엘엘씨 | 결정질의 (8s,9r)-5-플루오로-8-(4-플루오로페닐)-9-(1-메틸-1h-1,2,4-트리아졸-5-일)-8,9-디하이드로-2h-피리도[4,3,2-de]프탈라진-3(7h)-온 토실레이트 염 |
| WO2012166151A1 (en) | 2011-06-03 | 2012-12-06 | Biomarin Pharmaceutical Inc. | Use of dihydropyridophthalazinone inhibitors of poly (adp-ribose) polymerase (parp) in the treatment of myelodysplastic syndrome (mds) and acute myeloid leukaemia (aml) |
| WO2013028495A1 (en) | 2011-08-19 | 2013-02-28 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly (adp-ribose) polymerase (parp) for the treatment of multiple myeloma |
| US20130053365A1 (en) * | 2011-08-30 | 2013-02-28 | Biomarin Pharmaceutical, Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp) |
| CN105916846A (zh) | 2013-11-07 | 2016-08-31 | 麦迪韦逊科技有限公司 | 用于合成经保护的n-烷基三唑甲醛的三唑中间体 |
| EA201790290A1 (ru) | 2014-07-31 | 2017-07-31 | Медивэйшн Текнолоджиз, Инк. | Формерные соли (2s,3s)-метил 7-фтор-2-(4-фторфенил)-3-(1-метил-1h-1,2,4-триазол-5-ил)-4-оксо-1,2,3,4-тетрагидрохинолин-5-карбоксилата и способы их получения |
-
2011
- 2011-02-03 EP EP11740322.0A patent/EP2531033A4/en not_active Withdrawn
- 2011-02-03 WO PCT/US2011/023532 patent/WO2011097334A1/en not_active Ceased
- 2011-02-03 CN CN201710081268.6A patent/CN106943406A/zh active Pending
- 2011-02-03 AU AU2011212928A patent/AU2011212928B2/en not_active Ceased
- 2011-02-03 US US13/020,619 patent/US8541403B2/en not_active Expired - Fee Related
- 2011-02-03 JP JP2012552070A patent/JP5883397B2/ja not_active Expired - Fee Related
- 2011-02-03 CN CN201180017703XA patent/CN102869258A/zh active Pending
- 2011-02-03 CA CA2787844A patent/CA2787844C/en not_active Expired - Fee Related
-
2013
- 2013-08-21 US US13/972,166 patent/US9018201B2/en not_active Expired - Fee Related
-
2015
- 2015-03-27 US US14/671,944 patent/US20150209363A1/en not_active Abandoned
-
2016
- 2016-02-05 JP JP2016020358A patent/JP2016128492A/ja not_active Withdrawn
- 2016-09-22 AU AU2016231573A patent/AU2016231573A1/en not_active Abandoned
-
2017
- 2017-06-20 JP JP2017120148A patent/JP2017197565A/ja active Pending
-
2018
- 2018-07-20 AU AU2018206826A patent/AU2018206826A1/en not_active Abandoned
- 2018-08-03 US US16/054,899 patent/US10493078B2/en not_active Expired - Fee Related
- 2018-09-27 JP JP2018182009A patent/JP2019011356A/ja not_active Withdrawn
-
2020
- 2020-07-09 JP JP2020118694A patent/JP2020176136A/ja active Pending
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