JP2013518910A5 - - Google Patents
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- JP2013518910A5 JP2013518910A5 JP2012552143A JP2012552143A JP2013518910A5 JP 2013518910 A5 JP2013518910 A5 JP 2013518910A5 JP 2012552143 A JP2012552143 A JP 2012552143A JP 2012552143 A JP2012552143 A JP 2012552143A JP 2013518910 A5 JP2013518910 A5 JP 2013518910A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
- salt
- acid
- reducing reagent
- 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.)
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- 238000000034 method Methods 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 25
- 239000003153 chemical reaction reagent Substances 0.000 claims 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 8
- 229910052751 metal Inorganic materials 0.000 claims 8
- 239000002184 metal Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 6
- 230000005526 G1 to G0 transition Effects 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229910052723 transition metal Inorganic materials 0.000 claims 4
- 150000003624 transition metals Chemical class 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
- 229910052759 nickel Inorganic materials 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 229910052697 platinum Inorganic materials 0.000 claims 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 229910001507 metal halide Inorganic materials 0.000 claims 2
- 150000005309 metal halides Chemical group 0.000 claims 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 2
- 150000004681 metal hydrides Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 239000002516 radical scavenger Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- OJBNZAZUTPLWDT-UHFFFAOYSA-N 2-methyl-1,2,4-triazole-3-carbaldehyde Chemical compound CN1N=CN=C1C=O OJBNZAZUTPLWDT-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000003821 enantio-separation Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 238000004808 supercritical fluid chromatography Methods 0.000 claims 1
- 0 C[n]1ncnc1C(C(c(cc1)ccc1F)Nc1c2c(C(O*)=O)cc(F)c1)C2=O Chemical compound C[n]1ncnc1C(C(c(cc1)ccc1F)Nc1c2c(C(O*)=O)cc(F)c1)C2=O 0.000 description 14
- HWGQMRYQVZSGDQ-UHFFFAOYSA-N C[n]1ncnc1C(C(c(cc1)ccc1F)Nc1c2c3cc(F)c1)C2=NNC3=O Chemical compound C[n]1ncnc1C(C(c(cc1)ccc1F)Nc1c2c3cc(F)c1)C2=NNC3=O HWGQMRYQVZSGDQ-UHFFFAOYSA-N 0.000 description 4
- IHYDPJKFRHSULT-WTKPLQERSA-N C[n]1ncnc1/C=C(/c(c1cc(F)c2)c2[N+]([O-])=O)\OC1=O Chemical compound C[n]1ncnc1/C=C(/c(c1cc(F)c2)c2[N+]([O-])=O)\OC1=O IHYDPJKFRHSULT-WTKPLQERSA-N 0.000 description 2
- RFNLRJMPADAXDJ-LSFURLLWSA-N C[n]1ncnc1CC(c(c1cc(F)c2)c2/N=C/c(cc2)ccc2F)=NNC1=O Chemical compound C[n]1ncnc1CC(c(c1cc(F)c2)c2/N=C/c(cc2)ccc2F)=NNC1=O RFNLRJMPADAXDJ-LSFURLLWSA-N 0.000 description 2
- RUJPELCBXQXIFP-UHFFFAOYSA-N CN/C(/CC(c(c1cc(F)c2)c2N)=NNC1=O)=N\C=N Chemical compound CN/C(/CC(c(c1cc(F)c2)c2N)=NNC1=O)=N\C=N RUJPELCBXQXIFP-UHFFFAOYSA-N 0.000 description 1
- PAJDMXUECFRDFU-UHFFFAOYSA-N C[n]1ncnc1CC(c(c1cc(F)c2)c2N)=NNC1=O Chemical compound C[n]1ncnc1CC(c(c1cc(F)c2)c2N)=NNC1=O PAJDMXUECFRDFU-UHFFFAOYSA-N 0.000 description 1
- HWGQMRYQVZSGDQ-HOTGVXAUSA-N C[n]1ncnc1[C@@H]([C@H](c(cc1)ccc1F)Nc1cc(F)cc2c11)C1=NNC2=O Chemical compound C[n]1ncnc1[C@@H]([C@H](c(cc1)ccc1F)Nc1cc(F)cc2c11)C1=NNC2=O HWGQMRYQVZSGDQ-HOTGVXAUSA-N 0.000 description 1
- HWGQMRYQVZSGDQ-HZPDHXFCSA-N C[n]1ncnc1[C@H]([C@@H](c(cc1)ccc1F)Nc1c2c3cc(F)c1)C2=NNC3=O Chemical compound C[n]1ncnc1[C@H]([C@@H](c(cc1)ccc1F)Nc1c2c3cc(F)c1)C2=NNC3=O HWGQMRYQVZSGDQ-HZPDHXFCSA-N 0.000 description 1
- JBLFHMWQMPVDDL-UHFFFAOYSA-N [O-][N+](c1cc(F)cc2c1COC2=O)=O Chemical compound [O-][N+](c1cc(F)cc2c1COC2=O)=O JBLFHMWQMPVDDL-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30245710P | 2010-02-08 | 2010-02-08 | |
| US61/302,457 | 2010-02-08 | ||
| PCT/US2011/023965 WO2011097602A1 (en) | 2010-02-08 | 2011-02-08 | Processes of synthesizing dihydropyridophthalazinone derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013518910A JP2013518910A (ja) | 2013-05-23 |
| JP2013518910A5 true JP2013518910A5 (enExample) | 2014-03-27 |
| JP5735988B2 JP5735988B2 (ja) | 2015-06-17 |
Family
ID=44354222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012552143A Active JP5735988B2 (ja) | 2010-02-08 | 2011-02-08 | ジヒドロピリドフタラジノン誘導体を合成する方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US8765945B2 (enExample) |
| EP (1) | EP2533640B1 (enExample) |
| JP (1) | JP5735988B2 (enExample) |
| KR (1) | KR101826652B1 (enExample) |
| CN (1) | CN102834008B (enExample) |
| AU (1) | AU2011213584B2 (enExample) |
| BR (1) | BR112012019648B1 (enExample) |
| CA (1) | CA2788114C (enExample) |
| CY (1) | CY1118575T1 (enExample) |
| DK (1) | DK2533640T3 (enExample) |
| ES (1) | ES2606174T3 (enExample) |
| HU (1) | HUE030794T2 (enExample) |
| IL (1) | IL221170A (enExample) |
| MX (1) | MX340319B (enExample) |
| PL (1) | PL2533640T3 (enExample) |
| PT (1) | PT2533640T (enExample) |
| RU (1) | RU2561732C2 (enExample) |
| SG (1) | SG182784A1 (enExample) |
| SI (1) | SI2533640T1 (enExample) |
| WO (1) | WO2011097602A1 (enExample) |
| ZA (1) | ZA201205538B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2326650B9 (en) | 2008-08-06 | 2014-09-10 | BioMarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp) |
| CA2787844C (en) | 2010-02-03 | 2019-08-27 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose) polymerase (parp) for use in treatment of diseases associated with a pten deficiency |
| PL2533640T3 (pl) | 2010-02-08 | 2017-06-30 | Medivation Technologies, Inc. | Sposób syntezy pochodnych dihydropirydoftalazynonu |
| EP2630146B1 (en) | 2010-10-21 | 2020-07-01 | Medivation Technologies LLC | Crystaline (8s,9r)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1h-1,2,4-triazol-5-yl)-8,9-dihydro-2h-pyrido[4,3,2-de]phtalazin-3(7h)-one tosylate salt |
| EP3038600B1 (en) | 2013-08-27 | 2020-06-03 | Northeastern University | Nanoparticle drug delivery system and method of treating cancer and neurotrauma |
| 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 |
| JP2017523243A (ja) * | 2014-07-31 | 2017-08-17 | メディヴェイション テクノロジーズ， インコーポレーテッド | （２ｓ，３ｓ）−メチル ７−フルオロ−２−（４−フルオロフェニル）−３−（１−メチル−１ｈ−１，２，４−トリアゾール−５−イル）−４−オキソ−１，２，３，４−テトラヒドロキノリン−５−カルボキシレートの共形成剤塩、およびそれらを製造する方法 |
| CN104557917A (zh) * | 2014-12-12 | 2015-04-29 | 重庆博腾制药科技股份有限公司 | 一种5-卤代氮杂环吲哚的制备方法 |
| JP6786761B2 (ja) * | 2015-05-26 | 2020-11-18 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | Ｓｆｃによるキラル異性体の分離 |
| US9708319B1 (en) * | 2016-06-13 | 2017-07-18 | Yong Xu | Synthesis of PARP inhibitor talazoparib |
| WO2018122168A1 (en) | 2016-12-29 | 2018-07-05 | Bayer Pharma Aktiengesellschaft | Combinations of bub1 kinase and parp inhibitors |
| BR112020006371A2 (pt) | 2017-10-13 | 2020-09-29 | Merck Patent Gmbh | combinação de um inibidor de parp e um antagonista de ligação de eixo de pd-1 |
| 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 |
| WO2021181233A2 (en) | 2020-03-09 | 2021-09-16 | Pfizer Inc. | Fusion proteins and uses thereof |
| CA3201467A1 (en) | 2020-11-13 | 2022-05-19 | 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 |
| US20240180906A1 (en) | 2021-03-24 | 2024-06-06 | 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 |
| WO2025210510A1 (en) | 2024-04-04 | 2025-10-09 | Pfizer Inc. | Tmprss2-erg and rb1 as predictive biomarkers for treatment with a parp inhibitor |
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| CA2787844C (en) | 2010-02-03 | 2019-08-27 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(adp-ribose) polymerase (parp) for use in treatment of diseases associated with a pten deficiency |
| 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) |
| PL2533640T3 (pl) | 2010-02-08 | 2017-06-30 | Medivation Technologies, Inc. | Sposób syntezy pochodnych dihydropirydoftalazynonu |
| 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 |
| EP2630146B1 (en) * | 2010-10-21 | 2020-07-01 | Medivation Technologies LLC | Crystaline (8s,9r)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1h-1,2,4-triazol-5-yl)-8,9-dihydro-2h-pyrido[4,3,2-de]phtalazin-3(7h)-one tosylate salt |
| 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 |
| JP2017523243A (ja) | 2014-07-31 | 2017-08-17 | メディヴェイション テクノロジーズ， インコーポレーテッド | （２ｓ，３ｓ）−メチル ７−フルオロ−２−（４−フルオロフェニル）−３−（１−メチル−１ｈ−１，２，４−トリアゾール−５−イル）−４−オキソ−１，２，３，４−テトラヒドロキノリン−５−カルボキシレートの共形成剤塩、およびそれらを製造する方法 |
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2011
- 2011-02-08 PL PL11740513T patent/PL2533640T3/pl unknown
- 2011-02-08 AU AU2011213584A patent/AU2011213584B2/en not_active Ceased
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- 2011-02-08 CA CA2788114A patent/CA2788114C/en active Active
- 2011-02-08 US US13/023,140 patent/US8765945B2/en active Active
- 2011-02-08 PT PT117405134T patent/PT2533640T/pt unknown
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- 2011-02-08 JP JP2012552143A patent/JP5735988B2/ja active Active
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- 2011-02-08 KR KR1020127021601A patent/KR101826652B1/ko not_active Expired - Fee Related
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