JP2016534143A5 - - Google Patents
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- Publication number
- JP2016534143A5 JP2016534143A5 JP2016542643A JP2016542643A JP2016534143A5 JP 2016534143 A5 JP2016534143 A5 JP 2016534143A5 JP 2016542643 A JP2016542643 A JP 2016542643A JP 2016542643 A JP2016542643 A JP 2016542643A JP 2016534143 A5 JP2016534143 A5 JP 2016534143A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- phthalazin
- azetidine
- fluoro
- amino
- 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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- -1 methylene, carbonyl Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 230000003287 optical effect Effects 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- QRHLIWLOPSLNCU-UHFFFAOYSA-N 2h-phthalazin-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NN=CC2=C1 QRHLIWLOPSLNCU-UHFFFAOYSA-N 0.000 claims 2
- 108700020463 BRCA1 Proteins 0.000 claims 2
- 102000036365 BRCA1 Human genes 0.000 claims 2
- 101150072950 BRCA1 gene Proteins 0.000 claims 2
- 108700020462 BRCA2 Proteins 0.000 claims 2
- 102000052609 BRCA2 Human genes 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 101150008921 Brca2 gene Proteins 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- 101001077417 Gallus gallus Potassium voltage-gated channel subfamily H member 6 Proteins 0.000 claims 2
- 101001010792 Homo sapiens Transcriptional regulator ERG Proteins 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- QOTLMGGHCCVDEJ-UHFFFAOYSA-N N1(CCC1)C1CN(C1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F Chemical compound N1(CCC1)C1CN(C1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F QOTLMGGHCCVDEJ-UHFFFAOYSA-N 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 102100022807 Potassium voltage-gated channel subfamily H member 2 Human genes 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000004927 fusion Effects 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 230000009395 genetic defect Effects 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- OOGCIODHIGNQIQ-UHFFFAOYSA-N 4-[[4-fluoro-3-[3-[[1-(trifluoromethyl)cyclopropyl]amino]azetidine-1-carbonyl]phenyl]methyl]-2h-phthalazin-1-one Chemical compound FC1=CC=C(CC=2C3=CC=CC=C3C(=O)NN=2)C=C1C(=O)N(C1)CC1NC1(C(F)(F)F)CC1 OOGCIODHIGNQIQ-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
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| PCT/KR2014/008523 WO2015037939A1 (en) | 2013-09-13 | 2014-09-12 | A novel phtalazinone derivatives and manufacturing process thereof |
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| KR101670126B1 (ko) * | 2013-09-13 | 2016-10-27 | 일동제약(주) | 신규 프탈라지논 유도체 및 그 제조방법 |
| CA3129516A1 (en) * | 2018-02-28 | 2019-09-06 | The Trustees Of The University Of Pennsylvania | Low affinity poly(ad-ribose) polymerase 1 dependent cytotoxic agents |
| KR102913343B1 (ko) * | 2020-04-21 | 2026-01-15 | 아이디언스 주식회사 | 프탈라지논 화합물의 결정형 |
| WO2021214502A1 (en) * | 2020-04-21 | 2021-10-28 | Idience Co., Ltd. | Process for preparing a phthalazinone derivative and intermediates thereof |
| US20230159469A1 (en) * | 2020-05-08 | 2023-05-25 | Txinno Bioscience Inc. | Novel phthalazine derivative having ectonucloeotide pyrophosphatase/phosphodieste rase inhibitory activity, and use thereof |
| US12059419B2 (en) * | 2020-10-16 | 2024-08-13 | Idience Co., Ltd. | Pharmaceutical composition comprising phthalazinone derivatives |
| US20230391752A1 (en) * | 2020-10-22 | 2023-12-07 | Chulalongkorn University | Pyrrolidine-3-carboxamide derivatives and related uses |
| KR102977180B1 (ko) * | 2021-03-04 | 2026-06-15 | 아이디언스 주식회사 | Parp 억제제에 내성을 가진 환자군의 암 치료제로서의 프탈라지논 유도체의 항암제 용도 |
| WO2022186649A1 (ko) * | 2021-03-04 | 2022-09-09 | 아이디언스 주식회사 | Parp 억제제에 내성을 가진 환자군의 암 치료제로서의 프탈라지논 유도체의 항암제 용도 |
| TW202313040A (zh) * | 2021-06-02 | 2023-04-01 | 南韓商愛迪恩斯股份有限公司 | 以酞嗪酮衍生物治療病症的方法 |
| EP4469051A4 (en) * | 2022-01-25 | 2025-12-17 | Idience Co Ltd | Pharmaceutical composition with phthalazine derivative for simultaneous administration with an anticancer agent |
| WO2024025389A1 (ko) * | 2022-07-29 | 2024-02-01 | 아이디언스 주식회사 | 프탈라지논 유도체의 중간체의 제조방법 |
| CN117229260B (zh) * | 2023-11-13 | 2024-02-27 | 中国药科大学 | DNA聚合酶θ与聚ADP核糖聚合酶1双靶点抑制剂及其制备方法和医药用途 |
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| HU228960B1 (hu) | 2000-10-30 | 2013-07-29 | Kudos Pharm Ltd | Ftalazinon-származékok |
| DE60335359D1 (de) | 2002-04-30 | 2011-01-27 | Kudos Pharm Ltd | Phthalazinonderivate |
| PL1633724T3 (pl) * | 2003-03-12 | 2011-10-31 | Kudos Pharm Ltd | Pochodne ftalazynonu |
| US7449464B2 (en) | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0610680D0 (en) | 2006-05-31 | 2006-07-12 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| JP5271897B2 (ja) | 2006-05-31 | 2013-08-21 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・エルレ・エルレ | ポリ（ＡＤＰ−リボース）ポリメラーゼ（ＰＡＲＰ）の阻害剤としての、ピロロ［１，２−ａ］ピラジン−１（２Ｈ）−オン及びピロロ［１，２−ｄ］［１，２，４］トリアジン−１（２Ｈ）−オン誘導体 |
| MX347085B (es) | 2006-12-28 | 2017-04-06 | Abbott Laboratories * | Inhibidores de la poli (adp-ribosa) polimerasa. |
| CN101030723A (zh) | 2007-04-04 | 2007-09-05 | 钟志华 | 电磁变相发动机 |
| JP5758630B2 (ja) | 2007-11-15 | 2015-08-05 | エンメエッセディ・イタリア・エッセ・エッレ・エッレ | Ｐａｒｐ阻害剤としてのピリダジノン誘導体 |
| 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. |
| GB0804755D0 (en) | 2008-03-14 | 2008-04-16 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| 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 |
| 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 |
| CN102372716A (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 |
| CN102372698A (zh) | 2010-08-10 | 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 |
| EP2646428B1 (en) | 2010-12-02 | 2016-06-01 | Shanghai De Novo Pharmatech Co Ltd. | Heterocyclic derivatives, preparation processes and medical uses thereof |
| 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 |
| KR101670126B1 (ko) * | 2013-09-13 | 2016-10-27 | 일동제약(주) | 신규 프탈라지논 유도체 및 그 제조방법 |
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