BRPI0519893A2 - derivados da piperidina-2, 6-diona e o seu uso como inibidores do fator de necrose tumoral - Google Patents
derivados da piperidina-2, 6-diona e o seu uso como inibidores do fator de necrose tumoralInfo
- Publication number
- BRPI0519893A2 BRPI0519893A2 BRPI0519893-3A BRPI0519893A BRPI0519893A2 BR PI0519893 A2 BRPI0519893 A2 BR PI0519893A2 BR PI0519893 A BRPI0519893 A BR PI0519893A BR PI0519893 A2 BRPI0519893 A2 BR PI0519893A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- membered
- derivatives
- piperidine
- chr
- Prior art date
Links
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 title abstract 2
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 title abstract 2
- 150000005459 piperidine-2,6-diones Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- -1 1,3-propylene, 1,4-butylene, 1,5-pentylene Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000002831 pharmacologic agent Substances 0.000 abstract 1
- 150000003053 piperidines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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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
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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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P17/10—Anti-acne agents
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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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- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- 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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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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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
- C07D401/14—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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Gastroenterology & Hepatology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
DERIVADOS DA PIPERIDINA-2, 6-DIONA E ó SEU USO COMO INIBIDORES DO FATOR DE NECROSE TUMORAL. Esta invenção dirige-se aos derivados da piperklina-2,6-diona, ou respectivos sais orgânicos e inorgânicos, métodos para sintetizar estes derivados, e a sua aplicação como ingredientes farmacologicamente activos como inibklores do TNFa segregado nas células, sendo os derivados da piperidina-2,6-diona da fórmula geral (I): (I), em que n representa 1, 2, 3, 4, 5 ou 6; R¹ representa de um a quatro dos mesmos ou diferentes substituintes seleccionados de F, CI, Br, C~ 1-4~ alquilo, OH, OC~ 1-4~ alquilo, NO~ 2~, NHC(O)C~ 1-4~ alquilo, NH~ 2~, NH(C~ 1-4~ alquilo), N(C~ 1-4~ alquilo)~ 2~; R² representa OR³, NR³R^ 4^, N(R³)COR^ 4^, O~ 2~CR^ 5^; R^ 3^ e R^ 4^ representam independentemente e em cada ocorrência H ou C~ 1-4~ alquilo; R^ 5^ representa CHR^ 6^NR^ 7^R^ 8^, CHR^ 6^NR^ 9^C(O)CHR^ 10^NR^ 7^ R^ 8^, um heterociclo W ou CHR^ 6^NR^ 9^C(O)W; R^ 6^, R^ 9^, R^ 10^ representam bdependentemente e em cada ocorrência H, ou C~ 1-4~ alquilo; R^ 7^ e R^ 8^ representam independentemente e em cada ocorrência H, C~ 1-4~ alquilo, ou e R^ 8^ conjuntamente representam 1,3-propileno, 1 ,4-butileno, 1 ,5-pentileno, ou 1 ,6-hexileno; W representa um heterociclo de quatro membros, de cinco membros, de seis membros, de sete membros ou de oito membros, saturado ou insabrado.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100132923A CN100383139C (zh) | 2005-04-07 | 2005-04-07 | 可抑制细胞释放肿瘤坏死因子的哌啶-2,6-二酮衍生物 |
| PCT/CN2005/001467 WO2006105697A1 (fr) | 2005-04-07 | 2005-09-13 | Derives piperidyl-2,6-dione utilises pour empecher les cellules de liberer un facteur de necrose des tumeurs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0519893A2 true BRPI0519893A2 (pt) | 2009-03-31 |
Family
ID=37063089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0519893-3A BRPI0519893A2 (pt) | 2005-04-07 | 2005-09-13 | derivados da piperidina-2, 6-diona e o seu uso como inibidores do fator de necrose tumoral |
Country Status (11)
| Country | Link |
|---|---|
| US (5) | US8637545B2 (pt) |
| EP (1) | EP1867649B1 (pt) |
| JP (1) | JP5059745B2 (pt) |
| KR (1) | KR20080004485A (pt) |
| CN (1) | CN100383139C (pt) |
| AU (1) | AU2005330099A1 (pt) |
| BR (1) | BRPI0519893A2 (pt) |
| CA (1) | CA2604021A1 (pt) |
| ES (1) | ES2401281T3 (pt) |
| WO (1) | WO2006105697A1 (pt) |
| ZA (1) | ZA200709122B (pt) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100488959C (zh) * | 2003-03-27 | 2009-05-20 | 天津和美生物技术有限公司 | 水溶性的酞胺哌啶酮衍生物 |
| EP1940775A2 (en) | 2005-08-11 | 2008-07-09 | University of Massachusetts | Methods and compositions for the efficient delivery of therapeutic agents to cells and animals |
| CN101186612B (zh) * | 2006-11-15 | 2012-10-03 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的吡咯啉衍生物及其制备和应用 |
| CN101186611B (zh) | 2006-11-15 | 2011-05-18 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的吡咯啉-2-酮衍生物及其制备和应用 |
| US20110060010A1 (en) * | 2008-03-13 | 2011-03-10 | Tianjin Hemay Bio-Tech Co., Ltd | Salts of 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione and derivatives thereof, or polymorphs of salts, process for preparing same and use thereof |
| PT2358697E (pt) | 2008-10-29 | 2016-02-03 | Celgene Corp | Compostos de isoindolina para utilização no tratamento do cancro |
| CN108059635B (zh) | 2009-05-14 | 2021-10-01 | 天津合美医药科技有限公司 | 噻吩衍生物 |
| GB201311888D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201311891D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| RU2738833C9 (ru) * | 2014-04-14 | 2022-02-28 | Арвинас, Оперэйшнз, Инк. | Имидные модуляторы протеолиза и способы их применения |
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| WO2018095377A1 (zh) | 2016-11-24 | 2018-05-31 | 天津和美生物技术有限公司 | 哌啶-2,6-二酮衍生物以及溃疡性结肠炎的治疗 |
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| KR20250117470A (ko) | 2016-12-23 | 2025-08-04 | 아비나스 오퍼레이션스, 인코포레이티드 | 급속 진행성 섬유육종 폴리펩티드의 표적화 분해를 위한 화합물 및 방법 |
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| CR20220630A (es) | 2020-05-09 | 2023-01-23 | Arvinas Operations Inc | Métodos para fabricar un compuesto bifuncional, formas ultrapuras del compuesto bifuncional y formas de dosificación que comprenden el mismo |
| WO2022047145A1 (en) | 2020-08-28 | 2022-03-03 | Arvinas Operations, Inc. | Rapidly accelerating fibrosarcoma protein degrading compounds and associated methods of use |
| WO2022056368A1 (en) | 2020-09-14 | 2022-03-17 | Arvinas Operations, Inc. | Crystalline forms of a compound for the targeted degradation of estrogen receptor |
| CN112358465B (zh) * | 2020-10-27 | 2022-04-29 | 东莞东阳光科研发有限公司 | 一种化合物及其组成的电解液、锂离子电池 |
| KR20230171979A (ko) | 2021-04-16 | 2023-12-21 | 아비나스 오퍼레이션스, 인코포레이티드 | Bcl6 단백질 분해의 조절제 및 관련 사용 방법 |
| US20250066325A1 (en) * | 2021-11-04 | 2025-02-27 | The Brigham And Women's Hospital, Inc. | Directed degron molecules and applications thereof |
| WO2024054591A1 (en) | 2022-09-07 | 2024-03-14 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (raf) degrading compounds and associated methods of use |
| US12448399B2 (en) | 2023-01-26 | 2025-10-21 | Arvinas Operations, Inc. | Cereblon-based KRAS degrading PROTACs and uses related thereto |
| TW202535392A (zh) | 2023-12-08 | 2025-09-16 | 美商亞文納營運公司 | 使用雄性素受體降解劑治療脊髓延髓性肌肉萎縮 |
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| US4163058A (en) * | 1977-04-22 | 1979-07-31 | Interx Research Corporation | Derivatives of 5,5-diphenylhydantoin exhibiting enhanced solubility and the therapeutic use thereof |
| US4709042A (en) * | 1986-09-19 | 1987-11-24 | E. I. Du Pont De Nemours & Co., (Inc.) | Process for the preparation of 2-(1-hydroxyalkyl)-5,5-diphenylhydantoin |
| AU1531492A (en) * | 1991-02-14 | 1992-09-15 | Rockefeller University, The | Method for controlling abnormal concentration tnf alpha in human tissues |
| US5635517B1 (en) * | 1996-07-24 | 1999-06-29 | Celgene Corp | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
| HU228769B1 (en) * | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
| TR200101502T2 (tr) * | 1998-03-16 | 2002-06-21 | Celgene Corporation | 2-(2,6-dioksopiperidin-3-il) izoindolin türevleri, bunların hazırlanması ve enflamatuar sitokinlerin inhibitörleri olarak kullanımı |
| US7320991B2 (en) * | 2001-02-27 | 2008-01-22 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services, National Institutes Of Health | Analogs of thalidomide as potential angiogenesis inhibitors |
| ES2172474B1 (es) * | 2001-03-01 | 2004-01-16 | Fundacion Universitaria San Pa | Derivados de glutarimida como agentes terapeuticos. |
| US20050129616A1 (en) * | 2001-05-25 | 2005-06-16 | Human Genome Sciences, Inc. | Antibodies that immunospecifically bind to TRAIL receptors |
| CN100488959C (zh) * | 2003-03-27 | 2009-05-20 | 天津和美生物技术有限公司 | 水溶性的酞胺哌啶酮衍生物 |
| US7973057B2 (en) * | 2003-09-17 | 2011-07-05 | The United States Of America As Represented By The Department Of Health And Human Services | Thalidomide analogs |
| TWI466675B (zh) * | 2011-09-16 | 2015-01-01 | Univ China Medical | 用於抑制發炎之醫藥組合物 |
-
2005
- 2005-04-07 CN CNB2005100132923A patent/CN100383139C/zh not_active Expired - Lifetime
- 2005-09-13 KR KR1020077022834A patent/KR20080004485A/ko not_active Withdrawn
- 2005-09-13 EP EP05785096A patent/EP1867649B1/en not_active Expired - Lifetime
- 2005-09-13 ES ES05785096T patent/ES2401281T3/es not_active Expired - Lifetime
- 2005-09-13 JP JP2008504603A patent/JP5059745B2/ja not_active Expired - Lifetime
- 2005-09-13 WO PCT/CN2005/001467 patent/WO2006105697A1/zh not_active Ceased
- 2005-09-13 CA CA002604021A patent/CA2604021A1/en not_active Abandoned
- 2005-09-13 BR BRPI0519893-3A patent/BRPI0519893A2/pt not_active IP Right Cessation
- 2005-09-13 AU AU2005330099A patent/AU2005330099A1/en not_active Abandoned
-
2007
- 2007-10-07 US US11/868,502 patent/US8637545B2/en active Active
- 2007-10-23 ZA ZA200709122A patent/ZA200709122B/xx unknown
-
2013
- 2013-12-18 US US14/133,335 patent/US9085563B2/en not_active Expired - Lifetime
-
2015
- 2015-06-16 US US14/740,487 patent/US9669015B2/en not_active Expired - Lifetime
-
2017
- 2017-05-02 US US15/585,123 patent/US10166222B2/en not_active Expired - Lifetime
-
2018
- 2018-11-20 US US16/195,966 patent/US10406147B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006105697A1 (fr) | 2006-10-12 |
| CN100383139C (zh) | 2008-04-23 |
| JP2008534631A (ja) | 2008-08-28 |
| CA2604021A1 (en) | 2006-10-12 |
| US20150272940A1 (en) | 2015-10-01 |
| US9669015B2 (en) | 2017-06-06 |
| EP1867649B1 (en) | 2012-12-12 |
| US10406147B2 (en) | 2019-09-10 |
| US20190247383A1 (en) | 2019-08-15 |
| ZA200709122B (en) | 2008-12-31 |
| ES2401281T3 (es) | 2013-04-18 |
| US10166222B2 (en) | 2019-01-01 |
| US20180050025A1 (en) | 2018-02-22 |
| US8637545B2 (en) | 2014-01-28 |
| CN1844118A (zh) | 2006-10-11 |
| AU2005330099A1 (en) | 2006-10-12 |
| JP5059745B2 (ja) | 2012-10-31 |
| US20140179737A1 (en) | 2014-06-26 |
| EP1867649A4 (en) | 2009-02-18 |
| US9085563B2 (en) | 2015-07-21 |
| US20080051432A1 (en) | 2008-02-28 |
| EP1867649A1 (en) | 2007-12-19 |
| KR20080004485A (ko) | 2008-01-09 |
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