MXPA05010471A - Profarmacos inhibidores de quinasa pi-3. - Google Patents
Profarmacos inhibidores de quinasa pi-3.Info
- Publication number
- MXPA05010471A MXPA05010471A MXPA05010471A MXPA05010471A MXPA05010471A MX PA05010471 A MXPA05010471 A MX PA05010471A MX PA05010471 A MXPA05010471 A MX PA05010471A MX PA05010471 A MXPA05010471 A MX PA05010471A MX PA05010471 A MXPA05010471 A MX PA05010471A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- optionally substituted
- group
- aryl
- acid
- Prior art date
Links
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Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
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- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Rheumatology (AREA)
- Oncology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
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| US46013703P | 2003-04-03 | 2003-04-03 | |
| PCT/US2004/010399 WO2004089925A1 (en) | 2003-04-03 | 2004-04-03 | Pi-3 kinase inhibitor prodrugs |
Publications (1)
| Publication Number | Publication Date |
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| MXPA05010471A true MXPA05010471A (es) | 2006-05-25 |
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| MXPA05010471A MXPA05010471A (es) | 2003-04-03 | 2004-04-03 | Profarmacos inhibidores de quinasa pi-3. |
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| US8651113B2 (en) * | 2003-06-18 | 2014-02-18 | Swr&D Inc. | Magnetically responsive nanoparticle therapeutic constructs and methods of making and using |
| US20050043239A1 (en) * | 2003-08-14 | 2005-02-24 | Jason Douangpanya | Methods of inhibiting immune responses stimulated by an endogenous factor |
| US20050054614A1 (en) * | 2003-08-14 | 2005-03-10 | Diacovo Thomas G. | Methods of inhibiting leukocyte accumulation |
| EP2497836B1 (en) * | 2004-03-02 | 2015-01-14 | The Johns Hopkins University | Mutations of the PIK3CA gene in human cancers |
| EP1761540B1 (en) | 2004-05-13 | 2016-09-28 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
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| WO2006089106A2 (en) * | 2005-02-17 | 2006-08-24 | Icos Corporation | Phosphoinositide 3-kinase inhibitors for inhibiting leukocyte accumulation |
| EP1940386A4 (en) * | 2005-09-01 | 2010-06-23 | Beth Israel Hospital | WORDMAN'S CONJUGATES AND USES THEREOF |
| US20080139457A1 (en) * | 2005-09-16 | 2008-06-12 | Virginia Commonwealth University | Therapeutic compositions comprising chorionic gonadotropins and HMG CoA reductase inhibitors |
| NZ569086A (en) * | 2005-12-01 | 2011-07-29 | Trinity College Dublin | Compositions comprising a Toll-like receptor (TLR) agonist and an immune modulator for treating Th1-mediated conditions, such as cancer and infectious diseases |
| KR20080091829A (ko) * | 2006-02-09 | 2008-10-14 | 엔존 파마슈티컬즈, 인코포레이티드 | 유방암, 대장암, 췌장암, 난소암 및 폐암 치료용 7―에틸―10―히드록시캄포테신의 다분지형 고분자 접합체 |
| WO2007143630A2 (en) * | 2006-06-02 | 2007-12-13 | Nexgenix Pharmaceuticals | Treatment of neurofibromatosis with hsp90 inhibitors |
| US8329683B2 (en) * | 2006-06-02 | 2012-12-11 | Nexgenix Pharmaceuticals, Llc | Treatment of neurofibromatosis with radicicol and its derivatives |
| PE20090717A1 (es) * | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| EP2231152B1 (en) * | 2008-01-24 | 2014-01-01 | SignalRX Pharmaceuticals, Inc. | Thienopyranones as kinase inhibitors |
| WO2009108704A1 (en) * | 2008-02-25 | 2009-09-03 | Semafore Pharmaceuticals, Inc. | O-alkylated pi-3 kinase inhibitor prodrug combination |
| DE102008001855A1 (de) * | 2008-05-19 | 2009-11-26 | Evonik Degussa Gmbh | Zweikomponenten-Zusammensetzung zur Herstellung von flexiblen Polyurethan-Gelcoats |
| EP2303288A4 (en) | 2008-05-22 | 2015-04-22 | Univ Ramot | CONJUGATES OF A POLYMER, A BISPHOSPHONATE AND AN ANTI-ANGIOGENESE MEDIUM AND ITS USE IN THE TREATMENT AND CONTROL OF ILLNESSES RELATED TO BONE |
| US8524691B2 (en) | 2008-08-13 | 2013-09-03 | The Medicines Company | Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
| KR20160091440A (ko) | 2008-11-13 | 2016-08-02 | 길리아드 칼리스토가 엘엘씨 | 혈액 종양에 대한 요법 |
| US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
| WO2010107632A1 (en) | 2009-03-17 | 2010-09-23 | Woodway Usa, Inc. | Power generating manually operated treadmill |
| CA2756347A1 (en) | 2009-03-24 | 2010-09-30 | Gilead Calistoga Llc | Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use |
| SG175259A1 (en) | 2009-04-20 | 2011-11-28 | Gilead Calistoga Llc | Methods of treatment for solid tumors |
| ES3031438T3 (en) | 2009-06-25 | 2025-07-08 | Alkermes Pharma Ireland Ltd | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| CA2937222C (en) | 2009-06-25 | 2019-06-04 | Alkermes Pharma Ireland Limited | Prodrugs of nh-acidic compounds |
| AU2010276160A1 (en) | 2009-07-21 | 2012-02-09 | Gilead Calistoga Llc | Treatment of liver disorders with PI3K inhibitors |
| US8314934B2 (en) | 2009-09-01 | 2012-11-20 | Alltech Associates, Inc. | Methods and apparatus for analyzing samples and collecting sample fractions |
| SG10201500895XA (en) * | 2009-11-05 | 2015-04-29 | Rhizen Pharmaceuticals Sa | Chromen-4-one Derivatives As Kinase Modulators |
| WO2011163594A2 (en) | 2010-06-24 | 2011-12-29 | Alkermes, Inc. | Prodrugs of nh-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives |
| EP2655377B1 (en) | 2010-12-20 | 2016-03-30 | Glenmark Pharmaceuticals S.A. | 2-amino-4-arylthiazole compounds as trpa1 antagonists |
| US9034867B2 (en) | 2011-03-18 | 2015-05-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising sorbitan esters |
| US9359376B2 (en) * | 2011-04-08 | 2016-06-07 | Sphaera Pharma Pte. Ltd | Substituted methylformyl reagents and method of using same to modify physicochemical and/or pharmacokinetic properties of compounds |
| US8889657B2 (en) * | 2011-08-31 | 2014-11-18 | Mallinckrodt Llc | Nanoparticle PEG modification with H-phosphonates |
| WO2013088255A1 (en) | 2011-12-15 | 2013-06-20 | Alkermes Pharma Ireland Limited | Prodrugs of secondary amine compounds |
| BRPI1107182B1 (pt) * | 2011-12-29 | 2022-03-08 | Fundação De Amparo À Pesquisa Do Estado De Minas Gerais - Fapemig | Composições farmacêuticas contendo ang-(1-7) ou outro agonista do receptor mas em combinação com inibidores de pi3k/akt para tratamento terapêutico anticâncer |
| EP2822598A4 (en) | 2012-03-05 | 2016-04-13 | Univ Ramot | POLYMERS WITH THEREOF CONJUGATED THERAPEUTIC ACTIVE SUBSTANCES, METHOD FOR THE PREPARATION THEREOF AND USES THEREOF |
| EA025407B1 (ru) | 2012-03-05 | 2016-12-30 | Джилид Калистога Ллс | Полиморфная форма i (s)-2-(1-(9h-пурин-6-иламино)пропил)-5-фтор-3-фенилхиназолин-4(3h)-она |
| JP6219918B2 (ja) | 2012-03-19 | 2017-10-25 | アルカームス ファーマ アイルランド リミテッド | グリセロールエステルを含む医薬組成物 |
| WO2013142205A1 (en) | 2012-03-19 | 2013-09-26 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| WO2013142198A1 (en) | 2012-03-19 | 2013-09-26 | Alkermes Pharma Ireland Limited | Pharmaaceutical compositions comprising fatty acid esters |
| EP3718536A1 (en) | 2012-09-19 | 2020-10-07 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| WO2014068070A1 (en) | 2012-10-31 | 2014-05-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preventing antiphospholipid syndrome (aps) |
| RU2015143437A (ru) | 2013-03-15 | 2017-04-27 | Дженентек, Инк. | Способы лечения рака и предотвращения устойчивости к лекарственным препаратам для лечения рака |
| EP2986295A4 (en) * | 2013-04-17 | 2016-11-09 | Biopharma Works | PROCESS FOR PAIN TREATMENT |
| EP2986294A4 (en) | 2013-04-17 | 2016-11-16 | Biopharma Works | PROCESS FOR PAIN TREATMENT |
| NZ720867A (en) | 2013-12-20 | 2018-01-26 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
| WO2015095605A1 (en) | 2013-12-20 | 2015-06-25 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (s) -2-(9h-purin-6-ylamino) propyl) -5-fluoro-3-phenylquinazolin-4 (3h) -one |
| EP4019518A1 (en) | 2014-02-28 | 2022-06-29 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| US11066649B2 (en) | 2014-03-19 | 2021-07-20 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Method for inducing human cholangiocyte differentiation |
| EP3119399A4 (en) | 2014-03-20 | 2017-09-27 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| JP6455995B2 (ja) | 2014-06-13 | 2019-01-23 | ギリアード サイエンシーズ， インコーポレイテッド | ホスファチジルイノシトール３−キナーゼ阻害剤 |
| CN117164657A (zh) | 2014-08-12 | 2023-12-05 | 莫纳什大学 | 定向淋巴的前药 |
| WO2016065142A2 (en) | 2014-10-22 | 2016-04-28 | The Johns Hopkins University | New scaffolds and multifunctional intermediates for imaging psma and cancer therapy |
| KR102754019B1 (ko) | 2014-10-29 | 2025-01-14 | 바이시클러드 리미티드 | Mt1-mmp에 특이적인 바이사이클릭 펩타이드 리간드 |
| ES2930585T3 (es) | 2015-02-27 | 2022-12-19 | Nimbus Lakshmi Inc | Inhibidores de TYK2 y usos de los mismos |
| WO2017004134A1 (en) | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| KR102651945B1 (ko) * | 2015-07-07 | 2024-03-26 | 파이브 일레븐 파마 인크. | Hbed-비스포스포네이트, 이의 방사성금속 접합체 및 이의 진단치료제로서의 용도 |
| JP6802263B2 (ja) | 2015-09-02 | 2020-12-16 | ニンバス ラクシュミ， インコーポレイテッド | Ｔｙｋ２阻害剤およびその使用 |
| EP3347340A4 (en) | 2015-09-08 | 2019-01-23 | Monash University | LYMPHENLEITUNGSPRODRUGS |
| US10683308B2 (en) | 2015-09-11 | 2020-06-16 | Navitor Pharmaceuticals, Inc. | Rapamycin analogs and uses thereof |
| WO2017062504A1 (en) | 2015-10-06 | 2017-04-13 | Woodway Usa, Inc. | Manual treadmill and methods of operating the same |
| AU2016342027B2 (en) | 2015-10-23 | 2021-05-13 | Navitor Pharmaceuticals, Inc. | Modulators of Sestrin-GATOR2 interaction and uses thereof |
| US11548910B2 (en) | 2015-11-17 | 2023-01-10 | Nissan Chemical Corporation | Oligonucleotide production method |
| EP3389664A4 (en) | 2015-12-14 | 2020-01-08 | Raze Therapeutics Inc. | MTHFD2 CAFFEINE INHIBITORS AND USE THEREOF |
| PT3426243T (pt) | 2016-03-09 | 2021-08-19 | Raze Therapeutics Inc | Inibidores de 3-fosfoglicerato desidrogenase e utilizações dos mesmos |
| EP3426244B1 (en) | 2016-03-09 | 2023-06-07 | Raze Therapeutics, Inc. | 3-phosphoglycerate dehydrogenase inhibitors and uses thereof |
| WO2017162536A1 (en) | 2016-03-21 | 2017-09-28 | H. Lundbeck A/S | Vortioxetine prodrugs |
| WO2017175022A1 (en) | 2016-04-07 | 2017-10-12 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for inhibiting mast cell degranulation |
| WO2017177230A1 (en) | 2016-04-08 | 2017-10-12 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| CA3027500A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| JP7054529B2 (ja) | 2016-06-21 | 2022-04-14 | エックス４ ファーマシューティカルズ， インコーポレイテッド | Ｃｘｃｒ４阻害剤およびその使用 |
| WO2017223229A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| EP3478375B2 (en) | 2016-07-01 | 2024-05-22 | Woodway USA, Inc. | Motorized treadmill with motor braking mechanism and methods of operating same |
| US10072032B2 (en) * | 2016-09-19 | 2018-09-11 | Afton Chemical Corporation | AminoBisPhosphonate antiwear additives |
| CN115448916B (zh) | 2016-10-14 | 2026-04-28 | 武田药品工业株式会社 | Tyk2抑制剂及其用途 |
| JP7082120B2 (ja) | 2016-10-21 | 2022-06-07 | ニンバス ラクシュミ， インコーポレイテッド | Ｔｙｋ２阻害剤およびその使用 |
| WO2018089499A1 (en) | 2016-11-08 | 2018-05-17 | Navitor Pharmaceuticals, Inc. | PHENYL AMINO PIPERIDINE mTORC INHIBITORS AND USES THEREOF |
| AU2017368050A1 (en) | 2016-11-29 | 2019-06-20 | Puretech Lyt, Inc. | Exosomes for delivery of therapeutic agents |
| US11091451B2 (en) | 2016-12-05 | 2021-08-17 | Raze Therapeutics, Inc. | SHMT inhibitors and uses thereof |
| US11730819B2 (en) | 2016-12-23 | 2023-08-22 | Bicycletx Limited | Peptide derivatives having novel linkage structures |
| WO2018127699A1 (en) | 2017-01-06 | 2018-07-12 | Bicyclerd Limited | Compounds for treating cancer |
| EP3573619A4 (en) | 2017-01-27 | 2020-10-28 | SignalRX Pharmaceuticals, Inc. | THIENOPYRANONES AND FURANOPYRANONES AS KINASE, BROMODOMAIN AND CHECKPOINT INHIBITORS |
| TWI868528B (zh) | 2017-03-08 | 2025-01-01 | 日商武田藥品工業股份有限公司 | Ｔｙｋ２抑制劑之生產方法 |
| EP3375778A1 (en) | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aryl-piperidine derivatives |
| EP3375784A1 (en) | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aza-dihydro-acridone derivatives |
| WO2018191146A1 (en) | 2017-04-10 | 2018-10-18 | Navitor Pharmaceuticals, Inc. | Heteroaryl rheb inhibitors and uses thereof |
| US20200138964A1 (en) * | 2017-04-25 | 2020-05-07 | Seikagaku Corporation | Tertiary amine compound or imine compound-polymer conjugate and production method therefor |
| TWI776886B (zh) | 2017-04-26 | 2022-09-11 | 美商奈維特製藥公司 | Sestrin-gator2交互作用之調節劑及其用途 |
| US10857196B2 (en) | 2017-04-27 | 2020-12-08 | Bicycletx Limited | Bicyclic peptide ligands and uses thereof |
| HUE059057T2 (hu) | 2017-05-04 | 2022-10-28 | Bayer Cropscience Ag | 2-{[2-(feniloximetil)piridin-5-il]oxi}-etánamin-származékok és rokon vegyületek mint peszticidek, például növényvédelemre |
| CN108929329B (zh) * | 2017-05-24 | 2020-12-11 | 中国医学科学院药物研究所 | 2-氮杂环-5-三氟甲基-8-硝基苯并(硫代)吡喃-4-酮类化合物 |
| CN111032678A (zh) | 2017-06-26 | 2020-04-17 | 拜西克尔德有限公司 | 具有可检测部分的双环肽配体和其用途 |
| WO2019023468A1 (en) | 2017-07-28 | 2019-01-31 | Nimbus Lakshmi, Inc. | TYK2 INHIBITORS AND USES THEREOF |
| ES2926195T3 (es) | 2017-08-04 | 2022-10-24 | Bicycletx Ltd | Ligandos peptídicos bicíclicos específicos de CD137 |
| EP3668550A1 (en) | 2017-08-14 | 2020-06-24 | Bicyclerd Limited | Bicyclic peptide ligand prr-a conjugates and uses thereof |
| WO2019034866A1 (en) | 2017-08-14 | 2019-02-21 | Bicyclerd Limited | BICYCLIC PEPTIDE LIGANDS CONJUGATES AND USES THEREOF |
| WO2019046491A1 (en) | 2017-08-29 | 2019-03-07 | Ariya Therapeutics, Inc. | LIPIDIC PRODRUGS DIRECTING TO THE LYMPHATIC SYSTEM |
| US11883497B2 (en) | 2017-08-29 | 2024-01-30 | Puretech Lyt, Inc. | Lymphatic system-directing lipid prodrugs |
| JP7366031B2 (ja) | 2017-09-22 | 2023-10-20 | カイメラ セラピューティクス， インコーポレイテッド | タンパク質分解剤およびそれらの使用 |
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| US11304954B2 (en) | 2017-12-19 | 2022-04-19 | Puretech Lyt, Inc. | Lipid prodrugs of mycophenolic acid and uses thereof |
| GB201721265D0 (en) | 2017-12-19 | 2018-01-31 | Bicyclerd Ltd | Bicyclic peptide ligands specific for EphA2 |
| TWI825046B (zh) | 2017-12-19 | 2023-12-11 | 英商拜西可泰克斯有限公司 | Epha2特用之雙環胜肽配位基 |
| US11608345B1 (en) | 2017-12-19 | 2023-03-21 | Puretech Lyt, Inc. | Lipid prodrugs of rapamycin and its analogs and uses thereof |
| WO2019126378A1 (en) | 2017-12-19 | 2019-06-27 | Ariya Therapeutics, Inc. | Lipid prodrugs of mycophenolic acid and uses thereof |
| CN108003188A (zh) * | 2017-12-25 | 2018-05-08 | 长春吉大天元化学技术股份有限公司 | 一种烷基磷酸酯类化合物的新型纯化方法 |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| US11512080B2 (en) | 2018-01-12 | 2022-11-29 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| EP3737666A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | PROTEIN DEGRADATION AGENTS AND ASSOCIATED USES |
| JP7377207B2 (ja) | 2018-01-29 | 2023-11-09 | メルク パテント ゲーエムベーハー | Ｇｃｎ２阻害剤およびその使用 |
| EP4616913A3 (en) | 2018-01-29 | 2025-12-10 | Merck Patent GmbH | Gcn2 inhibitors and uses thereof |
| US10596165B2 (en) | 2018-02-12 | 2020-03-24 | resTORbio, Inc. | Combination therapies |
| AU2019224659A1 (en) | 2018-02-23 | 2020-10-15 | Bicycletx Limited | Multimeric bicyclic peptide ligands |
| EP3759086A1 (en) | 2018-02-27 | 2021-01-06 | Artax Biopharma Inc. | Chromene derivatives as inhibitors of tcr-nck interaction |
| CA3092335A1 (en) | 2018-03-05 | 2019-09-12 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| HUE067936T2 (hu) | 2018-04-24 | 2024-11-28 | Merck Patent Gmbh | Proliferáció-gátló vegyületek és alkalmazásuk |
| WO2019209757A1 (en) | 2018-04-24 | 2019-10-31 | Vertex Pharmaceuticals Incorporated | Pteridinone compounds and uses thereof |
| IL314362A (en) | 2018-06-15 | 2024-09-01 | Janssen Pharmaceutica Nv | Rapamycin analogs and their uses |
| US11180531B2 (en) | 2018-06-22 | 2021-11-23 | Bicycletx Limited | Bicyclic peptide ligands specific for Nectin-4 |
| GB201810316D0 (en) | 2018-06-22 | 2018-08-08 | Bicyclerd Ltd | Peptide ligands for binding to EphA2 |
| EP3817822A4 (en) | 2018-07-06 | 2022-07-27 | Kymera Therapeutics, Inc. | PROTEIN DEGRADANTS AND USES THEREOF |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| EP3827006A4 (en) | 2018-07-23 | 2022-04-06 | Signalrx Pharmaceuticals, Inc. | SINGLE-MOLECULE COMPOUNDS WITH MULTI-TARGET INHIBITION OF BTK AND OTHER PROTEINS AND METHODS OF USE THEREOF |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| JPWO2020050378A1 (ja) * | 2018-09-06 | 2021-08-30 | 生化学工業株式会社 | 第３級アミン化合物又はイミン化合物を結合させた、ポリマーコンジュゲートとその製造方法 |
| EP3846793B1 (en) | 2018-09-07 | 2024-01-24 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| CA3115088A1 (en) | 2018-10-15 | 2020-04-23 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| US10919937B2 (en) | 2018-10-23 | 2021-02-16 | Bicycletx Limited | Bicyclic peptide ligands and uses thereof |
| JP7644002B2 (ja) | 2018-10-24 | 2025-03-11 | ナビター ファーマシューティカルズ， インコーポレイテッド | 多形化合物およびその使用 |
| CN113271938A (zh) | 2018-11-30 | 2021-08-17 | 林伯士拉克许米公司 | Tyk2抑制剂和其用途 |
| JP7623943B2 (ja) | 2018-11-30 | 2025-01-29 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| GB201820325D0 (en) | 2018-12-13 | 2019-01-30 | Bicyclerd Ltd | Bicyclic peptide ligands specific for psma |
| GB201820288D0 (en) | 2018-12-13 | 2019-01-30 | Bicycle Tx Ltd | Bicycle peptide ligaands specific for MT1-MMP |
| GB201820295D0 (en) | 2018-12-13 | 2019-01-30 | Bicyclerd Ltd | Bicyclic peptide ligands specific for MT1-MMP |
| EP3670659A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Biomarkers, and uses in treatment of viral infections, inflammations, or cancer |
| CN113474045A (zh) | 2018-12-21 | 2021-10-01 | 拜斯科技术开发有限公司 | Pd-l1特异性的双环肽配体 |
| US12551567B2 (en) | 2018-12-21 | 2026-02-17 | Bicyclerd Limited | Bicyclic peptide ligands specific for PD-L1 |
| AU2020212001A1 (en) | 2019-01-23 | 2021-07-22 | Takeda Pharmaceutical Company Limited | TYK2 inhibitors and uses thereof |
| WO2020165600A1 (en) | 2019-02-14 | 2020-08-20 | Bicycletx Limited | Bicyclic peptide ligand sting conjugates and uses thereof |
| USD930089S1 (en) | 2019-03-12 | 2021-09-07 | Woodway Usa, Inc. | Treadmill |
| JP2022528887A (ja) | 2019-04-02 | 2022-06-16 | バイスクルテクス・リミテッド | バイシクルトキシンコンジュゲートおよびその使用 |
| US11485750B1 (en) | 2019-04-05 | 2022-11-01 | Kymera Therapeutics, Inc. | STAT degraders and uses thereof |
| WO2020243423A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| WO2020251971A1 (en) | 2019-06-10 | 2020-12-17 | Kymera Therapeutics, Inc. | Smarca degraders and uses thereof |
| WO2020251972A1 (en) | 2019-06-10 | 2020-12-17 | Kymera Therapeutics, Inc. | Smarca degraders and uses thereof |
| BR112021026517A2 (pt) | 2019-06-28 | 2022-05-10 | Kymera Therapeutics Inc | Degradadores de irak e usos dos mesmos |
| WO2021011868A1 (en) | 2019-07-17 | 2021-01-21 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| TWI860386B (zh) | 2019-07-30 | 2024-11-01 | 英商拜西可泰克斯有限公司 | 異質雙環肽複合物 |
| CN115038688A (zh) | 2019-09-11 | 2022-09-09 | 文森雷生物科学股份有限公司 | Usp30抑制剂及其用途 |
| PH12022550605A1 (en) | 2019-09-13 | 2023-09-25 | Nimbus Saturn Inc | Hpk1 antagonists and uses thereof |
| EP4051259A4 (en) | 2019-11-01 | 2023-11-22 | Navitor Pharmaceuticals, Inc. | METHOD OF TREATMENT USING A MMOC1 MODULATOR |
| BR112022010754A2 (pt) | 2019-12-05 | 2022-08-23 | Anakuria Therapeutics Inc | Análogos de rapamicina e usos dos mesmos |
| EP4072591A4 (en) | 2019-12-10 | 2024-06-05 | Kymera Therapeutics, Inc. | IRAQ DEGRADER AND USES THEREOF |
| JP2023509366A (ja) | 2019-12-17 | 2023-03-08 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| US12569485B2 (en) | 2019-12-23 | 2026-03-10 | Kymera Therapeutics, Inc. | SMARCA inhibitors and uses thereof |
| CN115297931A (zh) | 2019-12-23 | 2022-11-04 | 凯麦拉医疗公司 | Smarca降解剂和其用途 |
| AU2021217172A1 (en) | 2020-02-05 | 2022-09-22 | Monash University | Lipid prodrugs of neurosteroids |
| MX2022010944A (es) | 2020-03-03 | 2022-11-09 | Pic Therapeutics Inc | Inhibidores del factor de iniciacion de traduccion eucariotica 4e (eif4e) y sus usos. |
| IL296451B2 (en) | 2020-03-19 | 2026-05-01 | Kymera Therapeutics Inc | MDM2 joints and their uses |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| WO2021247897A1 (en) | 2020-06-03 | 2021-12-09 | Kymera Therapeutics, Inc. | Deuterated irak degraders and uses thereof |
| CA3189761A1 (en) | 2020-08-03 | 2022-02-10 | Gemma Mudd | Peptide-based linkers |
| KR20230074721A (ko) | 2020-08-17 | 2023-05-31 | 바이사이클티엑스 리미티드 | Nectin-4에 특이적인 이환 콘쥬게이트 및 이의 용도 |
| JP2023546996A (ja) | 2020-10-23 | 2023-11-08 | ニンバス クロソー， インコーポレイテッド | Ｃｔｐｓ１阻害剤およびその使用 |
| WO2022120353A1 (en) | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| IL303376A (en) | 2020-12-02 | 2023-08-01 | Ikena Oncology Inc | Tead inhibitors and uses thereof |
| EP4259144A4 (en) | 2020-12-09 | 2025-08-20 | Kymera Therapeutics Inc | SMARCA DEGRADING AGENTS AND THEIR USES |
| WO2022147465A1 (en) | 2020-12-30 | 2022-07-07 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| JP2024506858A (ja) | 2021-02-02 | 2024-02-15 | リミナル・バイオサイエンシーズ・リミテッド | Ｇｐｒ８４アンタゴニストおよびその使用 |
| KR20230153387A (ko) | 2021-02-02 | 2023-11-06 | 리미널 바이오사이언시스 리미티드 | Gpr84 길항제 및 이의 용도 |
| WO2022174253A1 (en) | 2021-02-12 | 2022-08-18 | Nimbus Saturn, Inc. | Hpk1 antagonists and uses thereof |
| TW202245788A (zh) | 2021-02-15 | 2022-12-01 | 美商凱麥拉醫療公司 | Irak4降解劑及其用途 |
| CN116867494A (zh) | 2021-02-15 | 2023-10-10 | 凯麦拉医疗公司 | Irak4降解剂和其用途 |
| CN117295737A (zh) | 2021-03-05 | 2023-12-26 | 林伯士萨顿公司 | Hpk1拮抗剂和其用途 |
| WO2022213062A1 (en) | 2021-03-29 | 2022-10-06 | Nimbus Saturn, Inc. | Hpk1 antagonists and uses thereof |
| EP4319756A4 (en) | 2021-04-09 | 2025-02-26 | Nimbus Clio, Inc. | CBL-B MODULATORS AND USES THEREOF |
| WO2022221866A1 (en) | 2021-04-16 | 2022-10-20 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| TW202315621A (zh) | 2021-08-25 | 2023-04-16 | 美商皮克醫療公司 | Ｅｉｆ４ｅ抑制劑及其用途 |
| JP2024532276A (ja) | 2021-08-25 | 2024-09-05 | ピク セラピューティクス， インコーポレイテッド | ｅＩＦ４Ｅ阻害剤及びその使用 |
| EP4422635A4 (en) | 2021-10-29 | 2025-11-26 | Kymera Therapeutics Inc | IRAQ4 DEGRADATION AGENTS AND THEIR SYNTHESIS |
| WO2023114984A1 (en) | 2021-12-17 | 2023-06-22 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| IL314437A (en) | 2022-01-31 | 2024-09-01 | Kymera Therapeutics Inc | IRAK joints and their uses |
| WO2023173053A1 (en) | 2022-03-10 | 2023-09-14 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| WO2023173057A1 (en) | 2022-03-10 | 2023-09-14 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| WO2023211889A1 (en) | 2022-04-25 | 2023-11-02 | Ikena Oncology, Inc. | Polymorphic compounds and uses thereof |
| KR20250040894A (ko) | 2022-05-25 | 2025-03-25 | 이케나 온콜로지, 인코포레이티드 | Mek 억제제 및 이의 용도 |
| JP2025527248A (ja) | 2022-08-02 | 2025-08-20 | リミナル・バイオサイエンシーズ・リミテッド | 置換ピリドンｇｐｒ８４アンタゴニスト及びその使用 |
| JP2025527247A (ja) | 2022-08-02 | 2025-08-20 | リミナル・バイオサイエンシーズ・リミテッド | アリール－トリアゾリル及び関連するｇｐｒ８４アンタゴニストならびにそれらの使用 |
| JP2025527250A (ja) | 2022-08-02 | 2025-08-20 | リミナル・バイオサイエンシーズ・リミテッド | ヘテロアリールカルボキサミド及び関連するｇｐｒ８４アンタゴニストならびにそれらの使用 |
| TW202430148A (zh) | 2022-11-22 | 2024-08-01 | 美商皮克醫療公司 | ｅＩＦ４Ｅ抑制劑及其用途 |
| EP4615455A2 (en) | 2023-06-23 | 2025-09-17 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| AU2024344754A1 (en) | 2023-09-21 | 2026-04-02 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors for use in the treatment of inflammatory bowel disease |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3937719A (en) * | 1975-01-06 | 1976-02-10 | American Home Products Corporation | (4-oxo-4h-1-benzopyran-2-yl)-oxamic acid, salts and esters anti-allergic agents |
| US5116954A (en) * | 1988-04-06 | 1992-05-26 | Lipha, Lyonnaise Industrielle Pharmaceutique | Pharmaceutically useful flavonoic compounds containing at least one substituent on the benzopyranone ring moiety |
| GB8914020D0 (en) * | 1989-06-19 | 1989-08-09 | Antisoma Ltd | Synthetic peptides for use in thrombus detection |
| EP0525123B1 (en) * | 1990-06-20 | 1997-09-17 | PHARMACIA & UPJOHN COMPANY | Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones |
| JP2918746B2 (ja) * | 1991-12-18 | 1999-07-12 | 富士写真フイルム株式会社 | ペプチド誘導体およびその用途 |
| US5985856A (en) | 1997-12-31 | 1999-11-16 | University Of Kansas | Water soluble prodrugs of secondary and tertiary amine containing drugs and methods of making thereof |
| JP2000169372A (ja) * | 1998-09-29 | 2000-06-20 | Takeda Chem Ind Ltd | 抗真菌薬組成物 |
| EP1857443B1 (en) * | 2000-01-24 | 2012-03-28 | AstraZeneca AB | Therapeutic morpholino-substituted compounds |
| AU1494702A (en) * | 2000-11-21 | 2002-06-03 | Leo Pharma As | Cyanoguanidine prodrugs |
| GB0119865D0 (en) * | 2001-08-14 | 2001-10-10 | Cancer Res Campaign Tech | DNA-PK inhibitors |
-
2004
- 2004-04-03 JP JP2006509693A patent/JP2006523237A/ja active Pending
- 2004-04-03 SG SG200716544-2A patent/SG160211A1/en unknown
- 2004-04-03 CN CNA2004800092262A patent/CN1826331A/zh active Pending
- 2004-04-03 EA EA200501563A patent/EA012240B1/ru not_active IP Right Cessation
- 2004-04-03 AU AU2004228668A patent/AU2004228668B2/en not_active Expired - Fee Related
- 2004-04-03 EP EP04758869A patent/EP1611119A1/en not_active Withdrawn
- 2004-04-03 BR BRPI0409063-2A patent/BRPI0409063A/pt not_active IP Right Cessation
- 2004-04-03 NZ NZ542475A patent/NZ542475A/en not_active IP Right Cessation
- 2004-04-03 KR KR1020057018781A patent/KR20070087266A/ko not_active Ceased
- 2004-04-03 MX MXPA05010471A patent/MXPA05010471A/es unknown
- 2004-04-03 WO PCT/US2004/010399 patent/WO2004089925A1/en not_active Ceased
- 2004-04-03 CA CA002518916A patent/CA2518916A1/en not_active Abandoned
- 2004-04-05 US US10/818,145 patent/US6949537B2/en not_active Expired - Fee Related
-
2005
- 2005-04-20 US US11/111,201 patent/US7396828B2/en not_active Expired - Fee Related
- 2005-09-30 ZA ZA200507954A patent/ZA200507954B/en unknown
-
2007
- 2007-12-21 US US11/962,612 patent/US7662977B2/en not_active Expired - Fee Related
-
2010
- 2010-10-20 JP JP2010235985A patent/JP2011057686A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SG160211A1 (en) | 2010-04-29 |
| BRPI0409063A (pt) | 2006-03-28 |
| CN1826331A (zh) | 2006-08-30 |
| ZA200507954B (en) | 2007-02-28 |
| US7396828B2 (en) | 2008-07-08 |
| JP2006523237A (ja) | 2006-10-12 |
| EA200501563A1 (ru) | 2006-06-30 |
| NZ542475A (en) | 2009-04-30 |
| US6949537B2 (en) | 2005-09-27 |
| WO2004089925A1 (en) | 2004-10-21 |
| AU2004228668A1 (en) | 2004-10-21 |
| AU2004228668B2 (en) | 2011-10-27 |
| US20050203173A1 (en) | 2005-09-15 |
| US20080188423A1 (en) | 2008-08-07 |
| EA012240B1 (ru) | 2009-08-28 |
| EP1611119A1 (en) | 2006-01-04 |
| US7662977B2 (en) | 2010-02-16 |
| CA2518916A1 (en) | 2004-10-21 |
| JP2011057686A (ja) | 2011-03-24 |
| KR20070087266A (ko) | 2007-08-28 |
| US20040242631A1 (en) | 2004-12-02 |
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