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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- ARYYJPZZAXETBK-FQEVSTJZSA-N FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)N(CC1=CC=NC=C1)C Chemical compound FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)N(CC1=CC=NC=C1)C ARYYJPZZAXETBK-FQEVSTJZSA-N 0.000 claims 1
- VHHWGQUFEYBJGI-FQEVSTJZSA-N FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)N(CC1=NC=CC=C1)C Chemical compound FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)N(CC1=NC=CC=C1)C VHHWGQUFEYBJGI-FQEVSTJZSA-N 0.000 claims 1
- DPFGBRGRDQYZLB-FQEVSTJZSA-N FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)N(CC=1C=NC=CC1)C Chemical compound FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)N(CC=1C=NC=CC1)C DPFGBRGRDQYZLB-FQEVSTJZSA-N 0.000 claims 1
- VIBFYTPXQPVJIJ-INIZCTEOSA-N FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)NC1=NC=CC=N1 Chemical compound FC1=C(C=C(CC2=NNC(C3=CC=CC=C23)=O)C=C1)C(=O)N1C[C@H](CC1)NC1=NC=CC=N1 VIBFYTPXQPVJIJ-INIZCTEOSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
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- SKUVJTCGUGKHKD-UHFFFAOYSA-N N1(CCC1)CC1CN(C1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F Chemical compound N1(CCC1)CC1CN(C1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F SKUVJTCGUGKHKD-UHFFFAOYSA-N 0.000 claims 1
- NMKURCNRNJLZQC-MRXNPFEDSA-N N1(CCC1)[C@H]1CN(CC1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F Chemical compound N1(CCC1)[C@H]1CN(CC1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F NMKURCNRNJLZQC-MRXNPFEDSA-N 0.000 claims 1
- VTTFHGJVTCQWLY-QGZVFWFLSA-N N1(CCCC1)[C@H]1CN(CC1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F Chemical compound N1(CCCC1)[C@H]1CN(CC1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F VTTFHGJVTCQWLY-QGZVFWFLSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical group C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005394 methallyl group Chemical group 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- YNBQAYKYNYRCCA-UHFFFAOYSA-N venadaparib Chemical compound C1(CC1)NCC1CN(C1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F YNBQAYKYNYRCCA-UHFFFAOYSA-N 0.000 claims 1
- YASSUAIJFUESOY-UHFFFAOYSA-N CN(C1)CC1(F)F Chemical compound CN(C1)CC1(F)F YASSUAIJFUESOY-UHFFFAOYSA-N 0.000 description 1
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- RXYPXQSKLGGKOL-UHFFFAOYSA-N CN1CCN(C)CC1 Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
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| KR20130110170 | 2013-09-13 | ||
| KR10-2013-0110170 | 2013-09-13 | ||
| KR10-2014-0120152 | 2014-09-11 | ||
| KR1020140120152A KR101670126B1 (ko) | 2013-09-13 | 2014-09-11 | 신규 프탈라지논 유도체 및 그 제조방법 |
| PCT/KR2014/008523 WO2015037939A1 (en) | 2013-09-13 | 2014-09-12 | A novel phtalazinone derivatives and manufacturing process thereof |
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Families Citing this family (13)
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| KR101670126B1 (ko) * | 2013-09-13 | 2016-10-27 | 일동제약(주) | 신규 프탈라지논 유도체 및 그 제조방법 |
| US11542282B2 (en) | 2018-02-28 | 2023-01-03 | The Trustees Of The University Of Pennsylvania | Low affinity poly(AD-ribose) polymerase 1 dependent cytotoxic agents |
| BR112022021321A2 (pt) * | 2020-04-21 | 2022-12-20 | Idience Co Ltd | Formas cristalinas do composto de ftalazinona. |
| US12060345B2 (en) | 2020-04-21 | 2024-08-13 | Idience Co., Ltd. | Process for preparing a phthalazinone derivative and intermediates thereof |
| EP4148046A4 (en) * | 2020-05-08 | 2024-07-24 | Txinno Bioscience Inc. | NEW PHTHALAZINE DERIVATIVE WITH ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE INHIBITING 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 |
| KR20220125183A (ko) | 2021-03-04 | 2022-09-14 | 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 |
| WO2023144626A1 (en) * | 2022-01-25 | 2023-08-03 | Idience Co., Ltd. | Pharmaceutical composition including phthalazinone derivative for co-administration with anticancer drug |
| 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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| GB2384776C (en) | 2000-10-30 | 2006-02-03 | Kudos Pharm Ltd | Phthalazinone derivatives |
| ES2357057T3 (es) | 2002-04-30 | 2011-04-15 | Kudos Pharmaceuticals Limited | Derivados de ftalazinona. |
| US7449464B2 (en) | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| KR101146806B1 (ko) | 2003-03-12 | 2012-05-22 | 메이브릿지 리미티드 | 프탈라지논 유도체 |
| 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) |
| GB0610680D0 (en) | 2006-05-31 | 2006-07-12 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| SI2698062T1 (sl) | 2006-12-28 | 2015-12-31 | Abbvie Inc. | Inhibitorji poli (ADP-riboza) polimeraze |
| CN101030723A (zh) | 2007-04-04 | 2007-09-05 | 钟志华 | 电磁变相发动机 |
| ES2524787T3 (es) | 2007-11-15 | 2014-12-12 | Msd Italia S.R.L. | Derivados de piridazinona como inhibidores de PARP |
| UY31603A1 (es) * | 2008-01-23 | 2009-08-31 | Derivados de ftalazinona | |
| GB0804755D0 (en) | 2008-03-14 | 2008-04-16 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2598491B1 (en) | 2010-07-27 | 2015-09-02 | 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 |
| ES2590682T3 (es) * | 2010-12-02 | 2016-11-23 | Shanghai De Novo Pharmatech Co Ltd. | Derivados heterocíclicos, procesos de preparación y usos médicos de los mismos |
| 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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