AU2009303335B2 - Activators of human pyruvate kinase - Google Patents
Activators of human pyruvate kinase Download PDFInfo
- Publication number
- AU2009303335B2 AU2009303335B2 AU2009303335A AU2009303335A AU2009303335B2 AU 2009303335 B2 AU2009303335 B2 AU 2009303335B2 AU 2009303335 A AU2009303335 A AU 2009303335A AU 2009303335 A AU2009303335 A AU 2009303335A AU 2009303335 B2 AU2009303335 B2 AU 2009303335B2
- Authority
- AU
- Australia
- Prior art keywords
- benzo
- dihydro
- dioxinyl
- difluorophenyl
- cio
- 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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Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2016216705A AU2016216705B2 (en) | 2008-10-09 | 2016-08-19 | Activators of human pyruvate kinase |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10409108P | 2008-10-09 | 2008-10-09 | |
| US61/104,091 | 2008-10-09 | ||
| PCT/US2009/060237 WO2010042867A2 (en) | 2008-10-09 | 2009-10-09 | Activators of human pyruvate kinase |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016216705A Division AU2016216705B2 (en) | 2008-10-09 | 2016-08-19 | Activators of human pyruvate kinase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009303335A1 AU2009303335A1 (en) | 2010-04-15 |
| AU2009303335B2 true AU2009303335B2 (en) | 2016-05-19 |
Family
ID=41462200
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009303335A Active AU2009303335B2 (en) | 2008-10-09 | 2009-10-09 | Activators of human pyruvate kinase |
| AU2016216705A Active AU2016216705B2 (en) | 2008-10-09 | 2016-08-19 | Activators of human pyruvate kinase |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016216705A Active AU2016216705B2 (en) | 2008-10-09 | 2016-08-19 | Activators of human pyruvate kinase |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US8841305B2 (enExample) |
| EP (2) | EP3173415B1 (enExample) |
| JP (2) | JP5632379B2 (enExample) |
| AU (2) | AU2009303335B2 (enExample) |
| CA (2) | CA2740148C (enExample) |
| ES (1) | ES2620634T3 (enExample) |
| WO (1) | WO2010042867A2 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008019139A2 (en) | 2006-08-04 | 2008-02-14 | Beth Israel Deaconess Medical Center | Inhibitors of pyruvate kinase and methods of treating disease |
| JP5632379B2 (ja) | 2008-10-09 | 2014-11-26 | アメリカ合衆国 | ヒトピルビン酸キナーゼ活性化剤 |
| EP2417123A2 (en) | 2009-04-06 | 2012-02-15 | Agios Pharmaceuticals, Inc. | Therapeutic compositions and related methods of use |
| DK2427441T3 (en) | 2009-05-04 | 2017-03-20 | Agios Pharmaceuticals Inc | PKM2 Activators for use in the treatment of cancer |
| EP2448581B1 (en) | 2009-06-29 | 2016-12-07 | Agios Pharmaceuticals, Inc. | Therapeutic compositions and related methods of use |
| CR20170071A (es) | 2009-06-29 | 2017-03-28 | Agios Pharmaceuticals Inc | Compuestos terapeuticos y composiciones |
| JP5909482B2 (ja) | 2010-03-31 | 2016-04-26 | ザ スクリプス リサーチ インスティテュート | 細胞の再プログラム |
| CA2797694A1 (en) * | 2010-04-29 | 2011-11-03 | The United States Of America, As Represented By The Secretary, Departmen T Of Health And Human Services | Activators of human pyruvate kinase |
| EP2632920A1 (en) | 2010-10-27 | 2013-09-04 | Dynamix Pharmaceuticals Ltd. | Sulfonamides for the modulation of pkm2 |
| EP2651898B1 (en) | 2010-12-17 | 2015-12-09 | Agios Pharmaceuticals, Inc. | Novel n-(4-(azetidine-1-carbonyl)phenyl)-(hetero-)arylsulfonamide derivatives as pyruvate kinase m2 (pmk2) modulators |
| WO2012088314A1 (en) * | 2010-12-21 | 2012-06-28 | Agios Pharmaceuticals, Inc. | Bicyclic pkm2 activators |
| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| ME03074B (me) | 2011-05-03 | 2019-01-20 | Agios Pharmaceuticals Inc | Akтivatori piruvat kinaze za upotrebu u terapiji |
| WO2012151440A1 (en) * | 2011-05-03 | 2012-11-08 | Agios Pharmaceuticals, Inc. | Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia |
| EP3372230B1 (en) | 2011-05-03 | 2020-08-12 | Agios Pharmaceuticals, Inc. | Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia |
| WO2013005157A1 (en) * | 2011-07-05 | 2013-01-10 | Lupin Limited | Sulfone derivatives and their use as pkm2 modulators for the treatment of cancer |
| WO2013027168A1 (en) * | 2011-08-22 | 2013-02-28 | Pfizer Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
| DE102012207707A1 (de) * | 2012-05-09 | 2013-11-28 | Deutsches Zentrum für Luft- und Raumfahrt e.V. | Minimalinvasives Instrument für die robotische Chirurgie |
| WO2014062838A2 (en) | 2012-10-16 | 2014-04-24 | Tolero Pharmaceuticals, Inc. | Pkm2 modulators and methods for their use |
| WO2014074848A1 (en) * | 2012-11-08 | 2014-05-15 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions and their use as pkm2 modulators |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| CN104370936A (zh) * | 2014-09-28 | 2015-02-25 | 苏州维泰生物技术有限公司 | 一种新型丙酮酸激酶m2激活剂及其合成方法 |
| MA44392B1 (fr) | 2015-06-11 | 2023-10-31 | Agios Pharmaceuticals Inc | Procédés d'utilisation d'activateurs de la pyruvate kinase |
| KR101713678B1 (ko) * | 2015-08-24 | 2017-03-09 | 대우제약 주식회사 | 신규 화합물 4-Ethyl-7-(2-fluoro-benzylsulfanyl)-2-methyl-1-thia-3b, 5, 6-triaza-cyclopenta[a]indene 및 이를 포함하는 항암제용 약제학적 조성물 |
| JP7332295B2 (ja) | 2016-01-25 | 2023-08-23 | スーパ-メタリクス,インコーポレイテッド. | 四ホウ化タングステンの結合材組成物及びそれらの研磨方法 |
| PT3448859T (pt) | 2017-03-20 | 2019-10-25 | Forma Therapeutics Inc | Composições de pirrolopirrole como ativadores de piruvato quinase (pkr). |
| SG11202001262QA (en) | 2017-08-15 | 2020-03-30 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in treating blood disorders |
| WO2019075367A1 (en) | 2017-10-13 | 2019-04-18 | Tolero Pharmaceuticals, Inc. | PKM2 ACTIVATORS IN COMBINATION WITH OXYGEN REACTIVE SPECIES FOR THE TREATMENT OF CANCER |
| US12233063B2 (en) | 2017-10-20 | 2025-02-25 | The Regents Of The University Of Michigan | Compositions and methods for treating eye disorders |
| US12053458B2 (en) | 2018-09-19 | 2024-08-06 | Novo Nordisk Health Care Ag | Treating sickle cell disease with a pyruvate kinase R activating compound |
| ES2989438T3 (es) * | 2018-09-19 | 2024-11-26 | Novo Nordisk Healthcare Ag | Activación de la piruvato cinasa R |
| SG11202108744WA (en) * | 2019-02-13 | 2021-09-29 | Agios Pharmaceuticals Inc | Thieno[3,2-b] pyrrole[3,2-d]pyridazinone derivatives and their use as pkm2 derivatives for the treatment of cancer, obesity and diabetes related disorders |
| WO2020198077A1 (en) | 2019-03-22 | 2020-10-01 | Sumitomo Dainippon Pharma Oncology, Inc. | Compositions comprising pkm2 modulators and methods of treatment using the same |
| CN110483504B (zh) * | 2019-08-02 | 2022-04-26 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-萘基)咪唑[1,2-a]吡啶-3-醛的新方法 |
| CN114615977B (zh) | 2019-09-19 | 2025-01-14 | 诺沃挪第克健康护理股份公司 | 丙酮酸激酶r(pkr)活化组合物 |
| DE102019129527A1 (de) | 2019-10-31 | 2021-05-06 | Forschungszentrum Jülich GmbH | Inhibitoren für Bromodomänen |
| US20230062100A1 (en) | 2019-11-28 | 2023-03-02 | Bayer Aktiengesellschaft | Substituted aminoquinolones as dgkalpha inhibitors for immune activation |
| WO2021105117A1 (en) | 2019-11-28 | 2021-06-03 | Bayer Aktiengesellschaft | Substituted aminoquinolones as dgkalpha inhibitors for immune activation |
| US12337005B2 (en) | 2020-05-26 | 2025-06-24 | University Of Iowa Research Foundation | Methods of treating thrombosis |
| EP4185293A4 (en) * | 2020-07-21 | 2025-01-15 | The Regents of The University of Michigan | COMPOSITIONS AND METHODS FOR ACTIVATING PYRUVATE KINASE |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
| CA3231728A1 (en) * | 2021-09-30 | 2023-04-06 | Sitryx Therapeutics Limited | Novel compounds |
| CN118434720A (zh) * | 2021-12-22 | 2024-08-02 | 西特瑞治疗有限公司 | 作为丙酮酸激酶调节剂的酞嗪衍生物 |
| CN115010721B (zh) * | 2022-03-14 | 2023-06-13 | 五邑大学 | 一种荧光探针及其制备方法和应用 |
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| US4593102A (en) * | 1984-04-10 | 1986-06-03 | A. H. Robins Company, Inc. | N-[(amino)alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulfur linked substitution in the 2, 3 or 4-position |
| WO1993013072A1 (en) * | 1991-12-20 | 1993-07-08 | Italfarmaco S.P.A. | 5-isoquinolinesulfonamide derivatives as protein kinase inhibiting agents |
| WO2002095063A1 (en) * | 2001-05-23 | 2002-11-28 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Pyruvate-kinase as a novel target molecule |
| WO2003106381A2 (en) * | 2002-06-12 | 2003-12-24 | Exelixis, Inc. | Human adam-10 inhibitors |
| US20070032418A1 (en) * | 2003-02-25 | 2007-02-08 | Ambion, Inc | Small-molecule inhibitors of angiogenin and rnases and in vivo and in vitro methods of using same |
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| US3998828A (en) * | 1975-01-31 | 1976-12-21 | Pfizer Inc. | 4-[2-(1,3-Dialkyl-1,2,3,4-tetra-hydropyrimidine-2,4-dione-5-carboxamido)ethyl]-1-piperidine sulfonamide |
| US4235871A (en) | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
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| ATE380818T1 (de) * | 2002-03-28 | 2007-12-15 | Lilly Co Eli | Piperazine-substituierte aryl-benzodiazepinen und ihre verwendung als dopaminrezeptor-antagonisten zur behandlung von psychose |
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| WO2008019139A2 (en) * | 2006-08-04 | 2008-02-14 | Beth Israel Deaconess Medical Center | Inhibitors of pyruvate kinase and methods of treating disease |
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| WO2009025781A1 (en) * | 2007-08-16 | 2009-02-26 | Beth Israel Deaconess Medical Center | Activators of pyruvate kinase m2 and methods of treating disease |
| US8642660B2 (en) * | 2007-12-21 | 2014-02-04 | The University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| JP5632379B2 (ja) | 2008-10-09 | 2014-11-26 | アメリカ合衆国 | ヒトピルビン酸キナーゼ活性化剤 |
| EP2575815A4 (en) * | 2010-06-04 | 2013-12-25 | Albany Molecular Res Inc | GLYCIN TRANSPORTER 1 INHIBITORS, METHODS OF MAKING THE SAME, AND USES THEREOF |
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2009
- 2009-10-09 JP JP2011531221A patent/JP5632379B2/ja active Active
- 2009-10-09 US US13/123,297 patent/US8841305B2/en active Active
- 2009-10-09 CA CA2740148A patent/CA2740148C/en active Active
- 2009-10-09 EP EP16207004.9A patent/EP3173415B1/en not_active Not-in-force
- 2009-10-09 EP EP09740795.1A patent/EP2344453B1/en active Active
- 2009-10-09 CA CA3041868A patent/CA3041868C/en active Active
- 2009-10-09 WO PCT/US2009/060237 patent/WO2010042867A2/en not_active Ceased
- 2009-10-09 AU AU2009303335A patent/AU2009303335B2/en active Active
- 2009-10-09 ES ES09740795.1T patent/ES2620634T3/es active Active
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2012
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2014
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- 2014-12-19 US US14/576,333 patent/US9290512B2/en active Active
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2016
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4593102A (en) * | 1984-04-10 | 1986-06-03 | A. H. Robins Company, Inc. | N-[(amino)alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulfur linked substitution in the 2, 3 or 4-position |
| WO1993013072A1 (en) * | 1991-12-20 | 1993-07-08 | Italfarmaco S.P.A. | 5-isoquinolinesulfonamide derivatives as protein kinase inhibiting agents |
| WO2002095063A1 (en) * | 2001-05-23 | 2002-11-28 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Pyruvate-kinase as a novel target molecule |
| WO2003106381A2 (en) * | 2002-06-12 | 2003-12-24 | Exelixis, Inc. | Human adam-10 inhibitors |
| US20070032418A1 (en) * | 2003-02-25 | 2007-02-08 | Ambion, Inc | Small-molecule inhibitors of angiogenin and rnases and in vivo and in vitro methods of using same |
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| US20150105395A1 (en) | 2015-04-16 |
| AU2009303335A1 (en) | 2010-04-15 |
| JP2015078188A (ja) | 2015-04-23 |
| JP5632379B2 (ja) | 2014-11-26 |
| WO2010042867A2 (en) | 2010-04-15 |
| US20160199370A1 (en) | 2016-07-14 |
| EP3173415A3 (en) | 2017-08-23 |
| JP5960770B2 (ja) | 2016-08-02 |
| US8937067B2 (en) | 2015-01-20 |
| JP2012505247A (ja) | 2012-03-01 |
| US9707230B2 (en) | 2017-07-18 |
| WO2010042867A3 (en) | 2010-08-05 |
| US20110195958A1 (en) | 2011-08-11 |
| EP2344453B1 (en) | 2016-12-28 |
| ES2620634T3 (es) | 2017-06-29 |
| US9290512B2 (en) | 2016-03-22 |
| AU2016216705B2 (en) | 2018-04-26 |
| US20120245141A1 (en) | 2012-09-27 |
| EP3173415B1 (en) | 2019-06-05 |
| CA3041868A1 (en) | 2010-04-15 |
| AU2016216705A1 (en) | 2016-09-08 |
| EP3173415A2 (en) | 2017-05-31 |
| US8841305B2 (en) | 2014-09-23 |
| CA2740148C (en) | 2019-06-18 |
| CA2740148A1 (en) | 2010-04-15 |
| EP2344453A2 (en) | 2011-07-20 |
| CA3041868C (en) | 2023-03-07 |
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