JP5525447B2 - Parp阻害剤としてのキノリノン誘導体 - Google Patents
Parp阻害剤としてのキノリノン誘導体 Download PDFInfo
- Publication number
- JP5525447B2 JP5525447B2 JP2010530433A JP2010530433A JP5525447B2 JP 5525447 B2 JP5525447 B2 JP 5525447B2 JP 2010530433 A JP2010530433 A JP 2010530433A JP 2010530433 A JP2010530433 A JP 2010530433A JP 5525447 B2 JP5525447 B2 JP 5525447B2
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- Prior art keywords
- alkyl
- hydrogen
- alkyloxy
- compound
- formula
- 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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- 0 CC1CCN(*)CC1 Chemical compound CC1CCN(*)CC1 0.000 description 14
- PVOAHINGSUIXLS-UHFFFAOYSA-N CN1CCNCC1 Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N C1NCCOC1 Chemical compound C1NCCOC1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N Cc1c[nH]c2ccccc12 Chemical compound Cc1c[nH]c2ccccc12 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N Cc1cnccn1 Chemical compound Cc1cnccn1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
- WKSGRDILLRKDQD-UHFFFAOYSA-N Cc1n[n-]c2c1cccc2 Chemical compound Cc1n[n-]c2c1cccc2 WKSGRDILLRKDQD-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- AIDS & HIV (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07119417.9 | 2007-10-26 | ||
| EP07119417 | 2007-10-26 | ||
| PCT/EP2008/064243 WO2009053373A1 (en) | 2007-10-26 | 2008-10-22 | Quinolinone derivatives as parp inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011500758A JP2011500758A (ja) | 2011-01-06 |
| JP2011500758A5 JP2011500758A5 (enExample) | 2011-12-08 |
| JP5525447B2 true JP5525447B2 (ja) | 2014-06-18 |
Family
ID=39345428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010530433A Expired - Fee Related JP5525447B2 (ja) | 2007-10-26 | 2008-10-22 | Parp阻害剤としてのキノリノン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8404713B2 (enExample) |
| EP (1) | EP2215075B1 (enExample) |
| JP (1) | JP5525447B2 (enExample) |
| ES (1) | ES2448870T3 (enExample) |
| PL (1) | PL2215075T3 (enExample) |
| WO (1) | WO2009053373A1 (enExample) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| CA2872883A1 (en) * | 2012-05-09 | 2013-11-14 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| WO2014085486A2 (en) | 2012-11-30 | 2014-06-05 | Waters Technologies Corporation | Methods and apparatus for the analysis of vitamin d metabolites |
| EP2970177A1 (en) | 2013-03-15 | 2016-01-20 | Pfizer Inc. | Indole compounds that activate ampk |
| BR112017003658B1 (pt) * | 2014-08-28 | 2022-12-06 | Asceneuron Sa | Composto, mistura, método para inibição de uma glicosidase, e, composição farmacêutica |
| ES2870203T3 (es) * | 2015-06-09 | 2021-10-26 | Onconic Therapeutics Inc | Compuesto derivado tricíclico, método para prepararlo y composición farmacéutica que comprende el mismo |
| EP3419976B1 (en) | 2016-02-25 | 2021-04-07 | Asceneuron SA | Acid addition salts of piperazine derivatives |
| EP3585783A2 (en) | 2016-02-25 | 2020-01-01 | Asceneuron SA | Sulfoximine glycosidase inhibitors |
| US11612599B2 (en) | 2016-02-25 | 2023-03-28 | Asceneuron Sa | Glycosidase inhibitors |
| AU2017222964B2 (en) | 2016-02-25 | 2020-01-02 | Asceneuron S. A. | Glycosidase inhibitors |
| MX2019010085A (es) | 2017-02-24 | 2019-11-21 | Asceneuron S A | Inhibidores de la glicosidasa de sulfoximina. |
| EP3672959A1 (en) | 2017-08-24 | 2020-07-01 | Asceneuron SA | Linear glycosidase inhibitors |
| EP3672958B1 (en) | 2017-08-24 | 2023-08-02 | Asceneuron SA | Annulated glycosidase inhibitors |
| US12016852B2 (en) | 2018-08-22 | 2024-06-25 | Asceneuron Sa | Pyrrolidine glycosidase inhibitors |
| US11731972B2 (en) | 2018-08-22 | 2023-08-22 | Asceneuron Sa | Spiro compounds as glycosidase inhibitors |
| EP3841093B1 (en) | 2018-08-22 | 2023-06-21 | Asceneuron SA | Succinate and fumarate acid addition salts of piperazine derivatives useful as glycosidase inhibitors |
| WO2020039028A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Tetrahydro-benzoazepine glycosidase inhibitors |
| US20220143042A1 (en) | 2019-02-22 | 2022-05-12 | Asceneuron Sa | Fused glycosidase inhibitors |
| HUE071067T2 (hu) * | 2019-07-19 | 2025-07-28 | Astrazeneca Ab | PARP1 inhibitorok |
| DK4003358T3 (da) * | 2019-07-26 | 2026-01-26 | Health Research Inc | Behandling af cancere med p53-mangel |
| US11795158B2 (en) | 2020-06-25 | 2023-10-24 | Astrazeneca Ab | Chemical compounds |
| MX2023012039A (es) * | 2021-04-12 | 2024-03-05 | Impact Therapeutics Shanghai Inc | Compuestos bicíclicos fusionados sustituidos como inhibidores de parp y uso de estos. |
| CA3216373A1 (en) | 2021-04-19 | 2022-10-27 | Lynnie TRZOSS | Parp1 inhibitors and uses thereof |
| AU2022261011A1 (en) * | 2021-04-22 | 2023-11-16 | Wigen Biomedicine Technology (shanghai) Co., Ltd. | Parp inhibitor containing piperazine structure, preparation method therefor and pharmaceutical use thereof |
| WO2022223025A1 (zh) * | 2021-04-23 | 2022-10-27 | 上海翰森生物医药科技有限公司 | 杂环类衍生物抑制剂、其制备方法和应用 |
| CN115702156A (zh) * | 2021-04-23 | 2023-02-14 | 南京明德新药研发有限公司 | 吡啶酰胺类化合物 |
| CN115232121B (zh) * | 2021-04-23 | 2023-08-29 | 成都百裕制药股份有限公司 | 吡啶衍生物及其在医药上的应用 |
| WO2022222966A1 (zh) * | 2021-04-23 | 2022-10-27 | 成都百裕制药股份有限公司 | 一种选择性parp1抑制剂及其应用 |
| US20240287094A1 (en) * | 2021-05-24 | 2024-08-29 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Nitrogen-containing heterocyclic compound, preparation method therefor, and application thereof in medicines |
| CN115403595A (zh) * | 2021-05-27 | 2022-11-29 | 江苏恒瑞医药股份有限公司 | 含氮杂环类化合物、其制备方法及其在医药上的应用 |
| WO2023036285A1 (zh) * | 2021-09-09 | 2023-03-16 | 南京奥利墨斯医药科技有限公司 | 一种杂芳环类化合物及其应用 |
| WO2023046034A1 (zh) * | 2021-09-22 | 2023-03-30 | 明慧医药(杭州)有限公司 | 一种含氮杂环化合物、其制备方法、其中间体及其应用 |
| WO2023046149A1 (zh) * | 2021-09-26 | 2023-03-30 | 张文燕 | 喹喔啉类化合物及其医药用途 |
| US20240400586A1 (en) * | 2021-09-30 | 2024-12-05 | Haisco Pharmaceutical Group Co., Ltd. | Heteroaryl derivative parp inhibitor and use thereof |
| CN118043322A (zh) * | 2021-09-30 | 2024-05-14 | 西藏海思科制药有限公司 | 含氮杂环衍生物parp抑制剂及其用途 |
| EP4410791A4 (en) * | 2021-09-30 | 2025-10-22 | Xizang Haisco Pharmaceutical Co Ltd | BICYCLIC DERIVATIVE PARP INHIBITOR AND ITS USE |
| CR20240144A (es) | 2021-10-01 | 2024-05-24 | Xinthera Inc | Inhibidores de parp1 de azetidina y pirrolidina y usos de estos |
| CA3235698A1 (en) * | 2021-10-22 | 2023-04-27 | Yao Li | Parp-1 degradation agent and use thereof |
| JP7762306B2 (ja) * | 2021-11-19 | 2025-10-29 | 康百達(四川)生物医薬科技有限公司 | 選択的parp1阻害剤およびその用途 |
| JP7804371B2 (ja) * | 2021-12-17 | 2026-01-22 | キーセラ(スーチョウ)バイオ-ファーマスーティカルズ カンパニー,リミテッド | Parp阻害剤、それを含む医薬組成物及びそれらの使用 |
| CN118434725B (zh) * | 2022-01-20 | 2026-01-02 | 微境生物医药科技(上海)有限公司 | 吡啶酰胺类parp抑制剂、及其制备方法和医药用途 |
| AU2023209820B2 (en) * | 2022-01-21 | 2024-10-10 | Xinthera, Inc. | Parp1 inhibitors and uses thereof |
| EP4469449A4 (en) * | 2022-01-27 | 2026-02-25 | Xinthera Inc | PARP1 INHIBITORS AND THEIR USES |
| CA3249318A1 (en) * | 2022-01-28 | 2023-08-03 | Xinthera, Inc. | PARP1 INHIBITORS AND THEIR USES |
| KR20240161147A (ko) | 2022-03-14 | 2024-11-12 | 슬랩 파마슈티컬스 엘엘씨 | 다중 사이클릭 화합물 |
| EP4514795A4 (en) * | 2022-04-28 | 2025-12-31 | Ningbo Newbay Tech Development Co Ltd | COMPOUNDS USED AS PARP1 INHIBITORS |
| CA3250945A1 (en) | 2022-04-28 | 2023-11-02 | Xinthera, Inc. | TRICYCLIC PARP1 INHIBITORS AND THEIR USES |
| WO2023207284A1 (en) * | 2022-04-28 | 2023-11-02 | Ningbo Newbay Technology Development Co., Ltd | Piperazine derivatives as parp1 inhibitiors |
| AU2023275808A1 (en) * | 2022-05-25 | 2024-12-12 | Xizang Haisco Pharmaceutical Co., Ltd. | Bicyclic derivative parp inhibitor and use thereof |
| EP4534533A4 (en) * | 2022-06-02 | 2026-04-29 | Chengdu Easton Biopharmaceuticals Co Ltd | AZAQUINOLINONE DERIVATIVE, ITS PREPARATION PROCESS AND ITS USE |
| WO2024041608A1 (zh) * | 2022-08-24 | 2024-02-29 | 四川海思科制药有限公司 | 一种杂芳基衍生物parp抑制剂的晶体形式及其用途 |
| CN119677736A (zh) * | 2022-08-24 | 2025-03-21 | 四川海思科制药有限公司 | 一种杂芳基衍生物parp抑制剂药学上可接受的盐及其用途 |
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| JP2011500758A (ja) | 2011-01-06 |
| ES2448870T3 (es) | 2014-03-17 |
| US8404713B2 (en) | 2013-03-26 |
| EP2215075A1 (en) | 2010-08-11 |
| PL2215075T3 (pl) | 2014-04-30 |
| WO2009053373A1 (en) | 2009-04-30 |
| US20100222348A1 (en) | 2010-09-02 |
| EP2215075B1 (en) | 2013-12-11 |
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