CA2821975A1 - N-(4-(azetidine-1-carbonyl)phenyl)-(hetero-) arylsulfonamide derivatives as pyruvate kinase m2 pkm2 modulators - Google Patents
N-(4-(azetidine-1-carbonyl)phenyl)-(hetero-) arylsulfonamide derivatives as pyruvate kinase m2 pkm2 modulators Download PDFInfo
- Publication number
- CA2821975A1 CA2821975A1 CA2821975A CA2821975A CA2821975A1 CA 2821975 A1 CA2821975 A1 CA 2821975A1 CA 2821975 A CA2821975 A CA 2821975A CA 2821975 A CA2821975 A CA 2821975A CA 2821975 A1 CA2821975 A1 CA 2821975A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- optionally substituted
- alkyl
- pkm2
- mmol
- 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.)
- Abandoned
Links
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Classifications
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D215/36—Sulfur 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
- C07D401/14—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
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061424395P | 2010-12-17 | 2010-12-17 | |
| US61/424,395 | 2010-12-17 | ||
| PCT/US2011/065633 WO2012083246A1 (en) | 2010-12-17 | 2011-12-16 | Novel n- (4- (azetidine - 1 - carbonyl) phenyl) - (hetero - ) arylsulfonamide derivatives as pyruvate kinase m2 (pmk2) modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2821975A1 true CA2821975A1 (en) | 2012-06-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2821975A Abandoned CA2821975A1 (en) | 2010-12-17 | 2011-12-16 | N-(4-(azetidine-1-carbonyl)phenyl)-(hetero-) arylsulfonamide derivatives as pyruvate kinase m2 pkm2 modulators |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9221792B2 (enExample) |
| EP (1) | EP2651898B1 (enExample) |
| JP (1) | JP5837091B2 (enExample) |
| CA (1) | CA2821975A1 (enExample) |
| ES (1) | ES2564952T3 (enExample) |
| MX (1) | MX2013006900A (enExample) |
| WO (1) | WO2012083246A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR077292A1 (es) | 2009-06-29 | 2011-08-17 | Agios Pharmaceuticals Inc | Derivados de piperazin - quinolin sulfonamidas y composiciones farmaceuticas |
| 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 |
| WO2012151448A1 (en) | 2011-05-03 | 2012-11-08 | Agios Pharmaceuticals, Inc. | Pyruvate kinase activators for use in therapy |
| DK2909181T3 (da) | 2012-10-16 | 2017-11-20 | Tolero Pharmaceuticals Inc | PKM2-modulatorer og fremgangsmåder til anvendelse deraf |
| CN104822672B (zh) * | 2012-11-08 | 2018-08-28 | 安吉奥斯医药品有限公司 | 治疗性化合物和组合物以及其作为pkm2调节剂的用途 |
| WO2014139144A1 (en) * | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| KR102007135B1 (ko) | 2017-03-20 | 2019-08-02 | 포르마 세라퓨틱스 인크. | 피루베이트 키나제 (pkr) 활성화제로서의 피롤로피롤 조성물 |
| EP3852791B1 (en) | 2018-09-19 | 2024-07-03 | Novo Nordisk Health Care AG | Activating pyruvate kinase r |
| US20200129485A1 (en) | 2018-09-19 | 2020-04-30 | Forma Therapeutics, Inc. | Treating sickle cell disease with a pyruvate kinase r activating compound |
| EP3941463A1 (en) | 2019-03-22 | 2022-01-26 | Sumitomo Dainippon Pharma Oncology, Inc. | Compositions comprising pkm2 modulators and methods of treatment using the same |
| US20220378756A1 (en) | 2019-09-19 | 2022-12-01 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
| US11566030B2 (en) | 2021-02-08 | 2023-01-31 | Global Blood Therapeutics, Inc. | Substituted 2,6-dihydropyrrolo[3,4-c]pyrazoles as pyruvate kinase activators |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
| CN118510768A (zh) | 2021-12-21 | 2024-08-16 | 赛诺哈勃药业(成都)有限公司 | 含二氮杂亚基磺酰结构的化合物及其在医药上的用途 |
Family Cites Families (138)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL80569C (enExample) | 1949-07-23 | |||
| GB935538A (en) | 1959-04-06 | 1963-08-28 | Stop Motion Devices Corp | Stop-motion head for use on knitting machines |
| GB1274436A (en) | 1970-06-09 | 1972-05-17 | Wolfen Filmfab Veb | Process for the sensitization of photographic silver chloride and silver chlorobromide emulsions that may contain colour couplers |
| 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 |
| DE2948434A1 (de) | 1979-12-01 | 1981-06-11 | Hoechst Ag, 6000 Frankfurt | 1-piperidinsulfonylharnstoffe und verfahren zu ihrer herstellung |
| US4474599A (en) | 1982-07-14 | 1984-10-02 | The Dow Chemical Company | 1-(Pyridyl)-1H-1,2,3-triazole derivatives, and use as herbicidal agents |
| US4501728A (en) | 1983-01-06 | 1985-02-26 | Technology Unlimited, Inc. | Masking of liposomes from RES recognition |
| GB8325370D0 (en) | 1983-09-22 | 1983-10-26 | Fujisawa Pharmaceutical Co | Benzoxazoline and benzothiazoline derivatives |
| 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 |
| IT1196195B (it) | 1984-07-20 | 1988-11-10 | Minnesota Mining & Mfg | Copulanti formatori di colorante cian ed elementi e procedimenti fotografici |
| US5019369A (en) | 1984-10-22 | 1991-05-28 | Vestar, Inc. | Method of targeting tumors in humans |
| JPS61129129A (ja) | 1984-11-28 | 1986-06-17 | Kureha Chem Ind Co Ltd | 抗腫瘍剤 |
| FI855180A7 (fi) | 1985-01-18 | 1986-07-19 | Nissan Chemical Ind Ltd | Pyratsolisulfonamidijohdannainen, menetelmä sen valmistamiseksi ja sitä sisältävä rikkaruohomyrkky. |
| EP0246749A3 (en) | 1986-05-17 | 1988-08-31 | AgrEvo UK Limited | Triazole herbicides |
| JPS6339875A (ja) | 1986-08-05 | 1988-02-20 | Nissin Food Prod Co Ltd | ピリミジン誘導体 |
| US4837028A (en) | 1986-12-24 | 1989-06-06 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| US4775762A (en) | 1987-05-11 | 1988-10-04 | The Dow Chemical Company | Novel (1H-1,2,3-triazol-1-yl)pyridines |
| US5962490A (en) | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| DE3813886A1 (de) | 1988-04-20 | 1989-11-02 | Schering Ag | 1-triazinyl-1h-1,2,4-triazol-3- sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
| DE3813885A1 (de) | 1988-04-20 | 1989-11-02 | Schering Ag | 1-chlorpyrimidinyl-1h-1,2,4-triazol-3-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
| US5220028A (en) | 1988-10-27 | 1993-06-15 | Nissan Chemical Industries, Ltd. | Halogeno-4-methylpyrazoles |
| KR910021381A (ko) | 1990-02-20 | 1991-12-20 | 모리 히데오 | 4-3급 부틸이미다졸 유도체, 및 이의 제조방법 및 용도 |
| CA2036148A1 (en) | 1990-06-29 | 1991-12-30 | Hiroki Tomioka | A 1-phenylimidazole derivative and its production and use |
| DK0565593T3 (da) | 1990-12-31 | 1999-09-27 | Monsanto Co | Reducering af pesticidinteraktion i afgrøder |
| US5252590A (en) | 1991-06-28 | 1993-10-12 | Sumitomo Chemical Company, Limited | 1-pyridylimidazole derivative |
| IT1252567B (it) | 1991-12-20 | 1995-06-19 | Italfarmaco Spa | Derivati di 5-isochinolinsolfonammidi inibitori delle protein-chinasi |
| JPH0625177A (ja) | 1992-07-09 | 1994-02-01 | Nissan Chem Ind Ltd | ピラゾール誘導体及び除草剤 |
| JP3409165B2 (ja) | 1993-04-28 | 2003-05-26 | 株式会社林原生物化学研究所 | 養毛剤とその製造方法 |
| JP3719612B2 (ja) | 1993-06-14 | 2005-11-24 | 塩野義製薬株式会社 | ヘテロ環を含有する尿素誘導体 |
| JP3545461B2 (ja) * | 1993-09-10 | 2004-07-21 | エーザイ株式会社 | 二環式ヘテロ環含有スルホンアミド誘導体 |
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| WO1996022287A1 (en) | 1995-01-20 | 1996-07-25 | G.D. Searle & Co. | Bis-sulfonamide hydroxyethylamino retroviral protease inhibitors |
| IL117580A0 (en) | 1995-03-29 | 1996-07-23 | Merck & Co Inc | Inhibitors of farnesyl-protein transferase and pharmaceutical compositions containing them |
| FR2735127B1 (fr) | 1995-06-09 | 1997-08-22 | Pf Medicament | Nouvelles piperazines heteroaromatiques utiles comme medicaments. |
| ES2100129B1 (es) | 1995-10-11 | 1998-02-16 | Medichem Sa | Nuevos compuestos aminopiridinicos policiclicos inhibidores de acetilcolinesterasa, procedimiento para su preparacion y su utilizacion. |
| DE19541146A1 (de) | 1995-10-25 | 1997-04-30 | Schering Ag | Imidazolderivate und deren Verwendung als Stickstoffmonoxid-Synthase-Inhibitoren |
| FR2744449B1 (fr) | 1996-02-02 | 1998-04-24 | Pf Medicament | Nouvelles piperazines aromatiques derivees de cycloazanes substitues, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
| JP2000504336A (ja) | 1996-02-02 | 2000-04-11 | ゼネカ・リミテッド | 薬学製剤として有用なヘテロ環式化合物 |
| GB9602166D0 (en) | 1996-02-02 | 1996-04-03 | Zeneca Ltd | Aminoheterocyclic derivatives |
| JP2000510866A (ja) | 1996-05-20 | 2000-08-22 | ダーウィン・ディスカバリー・リミテッド | Tnfとpde―ivのインヒビターとしてのキノリンスルホンアミド |
| DE19629335A1 (de) | 1996-07-20 | 1998-01-22 | Golden Records Ass Internation | Karte aus Kunststoff |
| US6020357A (en) | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| DE19702988A1 (de) | 1997-01-28 | 1998-07-30 | Hoechst Ag | Isoxazol- und Crotonsäureamidderivate und deren Verwendung als Arzneimittel und Diagnostika |
| CA2280515A1 (en) | 1997-03-11 | 1998-09-17 | E.I. Du Pont De Nemours And Company | Heteroaryl azole herbicides |
| US7863444B2 (en) | 1997-03-19 | 2011-01-04 | Abbott Laboratories | 4-aminopyrrolopyrimidines as kinase inhibitors |
| DE19743435A1 (de) | 1997-10-01 | 1999-04-08 | Merck Patent Gmbh | Benzamidinderivate |
| US6106849A (en) | 1998-01-21 | 2000-08-22 | Dragoco Gerberding & Co. Ag | Water soluble dry foam personal care product |
| WO2000012077A1 (en) | 1998-09-01 | 2000-03-09 | Bristol-Myers Squibb Company | Potassium channel inhibitors and method |
| DE19841985A1 (de) | 1998-09-03 | 2000-03-09 | Schering Ag | Dialkylsulfonsäure- und Dialkylcarbonsäure-Derivate |
| CN1326457A (zh) | 1998-09-18 | 2001-12-12 | 巴斯福股份公司 | 作为激酶抑制剂的4-氨基吡咯并嘧啶 |
| US6211182B1 (en) | 1999-03-08 | 2001-04-03 | Schering Corporation | Imidazole compounds substituted with a six or seven membered heterocyclic ring containing two nitrogen atoms |
| US6492408B1 (en) | 1999-07-21 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Small molecules useful in the treatment of inflammatory disease |
| JP2003509412A (ja) | 1999-09-17 | 2003-03-11 | シーオーアール セラピューティクス インコーポレイテッド | Xa因子阻害剤 |
| EP1216228B1 (en) | 1999-09-17 | 2008-10-29 | Millennium Pharmaceuticals, Inc. | BENZAMIDES AND RELATED INHIBITORS OF FACTOR Xa |
| AU2001245353A1 (en) | 2000-02-29 | 2001-09-12 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| US20010037689A1 (en) | 2000-03-08 | 2001-11-08 | Krouth Terrance F. | Hydraulic actuator piston measurement apparatus and method |
| FR2817349B1 (fr) | 2000-11-28 | 2003-06-20 | Centre Nat Rech Scient | Nouveau procede de criblage de modulateurs de la transcription bacterienne |
| JP2002193710A (ja) | 2000-12-25 | 2002-07-10 | Kumiai Chem Ind Co Ltd | ピリミジン又はトリアジン誘導体及び農園芸用殺菌剤 |
| DE10164711A1 (de) | 2001-03-13 | 2002-10-17 | Schebo Biotech Ag | Verwendung von Zuckerphosphaten, Zuckerphosphatanalogen, Aminosäuren und/oder Aminosäureanalogen zur Modulation des Glycolyse-Enzym-Komplexes, des Malat Aspartat Shuttles und/oder der Transaminasen |
| EP1389194A2 (en) | 2001-04-27 | 2004-02-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of bace |
| WO2002089793A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| US20040152648A1 (en) | 2001-05-23 | 2004-08-05 | Axel Ullrich | Pyruvate-kinase as a novel target molecule |
| US6967212B2 (en) | 2001-05-30 | 2005-11-22 | Bristol-Myers Squibb Company | Substituted azole acid derivatives useful as antidiabetic and antiobesity agents and method |
| US7144883B2 (en) | 2001-06-11 | 2006-12-05 | Biovitrum Ab | Bicyclic sulfonamide compounds |
| JP4083397B2 (ja) | 2001-06-18 | 2008-04-30 | 株式会社ルネサステクノロジ | 半導体集積回路装置 |
| RU2283839C2 (ru) | 2001-08-15 | 2006-09-20 | Е.И.Дюпон Де Немур Энд Компани | Ортозамещенные ариламиды, способ борьбы с насекомыми, композиция для борьбы с насекомыми, промежуточное соединение |
| JP2003081937A (ja) | 2001-09-07 | 2003-03-19 | Bayer Ag | ベンゼンスルホンアミド誘導体 |
| US7169788B2 (en) | 2001-10-30 | 2007-01-30 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| EP1472248A1 (en) | 2002-01-17 | 2004-11-03 | Eli Lilly And Company | Modulators of acetylcholine receptors |
| WO2003073999A2 (en) | 2002-03-01 | 2003-09-12 | Pintex Pharmaceuticals, Inc. | Pini-modulating compounds and methods of use thereof |
| WO2003076400A1 (en) | 2002-03-13 | 2003-09-18 | Janssen Pharmaceutica N.V. | New inhibitors of histone deacetylase |
| KR20040090978A (ko) | 2002-03-13 | 2004-10-27 | 얀센 파마슈티카 엔.브이. | 히스톤 디아세틸라제의 신규한 저해제로서의 설포닐-유도체 |
| EP1501514B1 (en) | 2002-05-03 | 2012-12-19 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| GB0215775D0 (en) | 2002-07-06 | 2002-08-14 | Astex Technology Ltd | Pharmaceutical compounds |
| CA2494962C (en) | 2002-08-09 | 2011-06-14 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| CA2501228A1 (en) | 2002-10-24 | 2004-05-06 | Sterix Limited | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 and type 2 |
| WO2004073619A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| WO2004074438A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| 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 |
| JP4629657B2 (ja) | 2003-04-11 | 2011-02-09 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | 11β−ヒドロキシステロイドデヒドロゲナーゼ1型化活性化合物 |
| EP1635832A2 (en) | 2003-06-06 | 2006-03-22 | Merck & Co., Inc. | Combination therapy for the treatment of diabetes |
| US6818631B1 (en) | 2003-08-15 | 2004-11-16 | Nippon Soda Co. Ltd. | Fungicidal pyrimidine derivatives |
| US20080051414A1 (en) | 2003-10-14 | 2008-02-28 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Protein Kinase Inhibitors |
| US20050170316A1 (en) | 2004-01-29 | 2005-08-04 | Russell Bruce M. | Toothbrush for detecting the presence of plaque |
| WO2005074946A1 (en) | 2004-02-10 | 2005-08-18 | Adenobio N.V. | Stable and active complexes of adenosine and adenosine phosphates with aminoalcohols for the treatment of pulmonary artery hypertension, cardiac failure and other diseases |
| CA2556589A1 (en) | 2004-02-24 | 2005-09-01 | Bioaxone Therapeutique Inc. | 4-substituted piperidine derivatives |
| US7588779B2 (en) | 2004-05-28 | 2009-09-15 | Andrx Labs, Llc | Pharmaceutical formulation containing a biguanide and an angiotensin antagonist |
| GB0412526D0 (en) | 2004-06-05 | 2004-07-14 | Leuven K U Res & Dev | Type 2 diabetes |
| CA2577309C (en) | 2004-06-24 | 2013-10-22 | Temple University - Of The Commonwealth System Of Higher Education | Alpha, beta-unsaturated sulfones, sulfoxides, sulfonimides, sulfinimides, acylsulfonamides and acylsulfinamides and therapeutic uses thereof |
| TW200606152A (en) | 2004-07-02 | 2006-02-16 | Tanabe Seiyaku Co | Piperidine compound and process for preparing the same |
| FR2872704B1 (fr) | 2004-07-12 | 2007-11-02 | Laurent Schwartz | Pluritherapie contre le cancer |
| EP2316458A1 (en) | 2004-09-20 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| JP2008514590A (ja) * | 2004-09-24 | 2008-05-08 | アストラゼネカ・アクチエボラーグ | ベンゾイミダゾール誘導体、それを含む組成物、その製造方法及びその使用 |
| WO2006038594A1 (ja) | 2004-10-04 | 2006-04-13 | Ono Pharmaceutical Co., Ltd. | N型カルシウムチャネル阻害薬 |
| US20070249625A1 (en) | 2004-10-20 | 2007-10-25 | Jakob Busch-Petersen | Il-8 Receptor Antagonists |
| WO2006052546A2 (en) | 2004-11-04 | 2006-05-18 | Neurogen Corporation | Pyrazolylmethyl heteroaryl derivatives |
| SE0402762D0 (sv) | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
| WO2006055880A2 (en) | 2004-11-16 | 2006-05-26 | Genzyme Corporation | Diagnostic pkm2 methods and compositions |
| JP2008526723A (ja) | 2004-12-30 | 2008-07-24 | アステックス、セラピューティックス、リミテッド | Cdk、gsk及びオーロラキナーゼの活性を調節するピラゾール誘導体 |
| WO2006087543A1 (en) | 2005-02-18 | 2006-08-24 | Astrazeneca Ab | Antibacterial piperidine derivatives |
| SI1879877T1 (sl) | 2005-05-03 | 2013-02-28 | Ranbaxy Laboratories Limited | Protimikrobna sredstva |
| DE112006002052A5 (de) | 2005-05-18 | 2008-05-08 | Forschungsverbund Berlin E.V. | Nicht-Peptidische Inhibitoren der AKAP-PKA-Wechselwirkung |
| GB0513702D0 (en) | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
| JP2009501705A (ja) | 2005-07-05 | 2009-01-22 | アストラゼネカ・アクチエボラーグ | 新規化合物、その製造方法、中間体、医薬組成物、並びにアルツハイマー病、認知障害、統合失調症に伴う認識機能障害、肥満及びパーキンソン病のような5−ht6介在疾患の治療におけるそれらの使用 |
| EA015937B1 (ru) | 2005-08-26 | 2011-12-30 | Мерк Сероно С.А. | Производные пиразина и их применение в качестве ингибиторов pi3k |
| FI20055644A0 (fi) | 2005-12-02 | 2005-12-02 | Nokia Corp | Ryhmäviestintä |
| JP2009521444A (ja) | 2005-12-22 | 2009-06-04 | メルク エンド カムパニー インコーポレーテッド | カルシウムチャンネルブロッカーとなる置換ピペリジン |
| BRPI0706654A2 (pt) | 2006-01-20 | 2011-04-05 | Smithkline Beecham Corp | composição farmacêutica, método para tratar condições ou distìrbios em um mamìfero, uso de um composto, e, composto |
| JP2007238458A (ja) | 2006-03-06 | 2007-09-20 | D Western Therapeutics Institute Inc | 新規なイソキノリン誘導体及びこれを含有する医薬 |
| US20090054453A1 (en) | 2006-03-17 | 2009-02-26 | Lilian Alcaraz | Novel Tetralins as 5-HT6 Modulators |
| MX2008012064A (es) | 2006-03-23 | 2008-12-17 | Amgen Inc | Compuestos de amida 1-fenilsulfonil-diaza-heterociclica y sus usos como moduladores de hidroxiesteroide deshidrogenadas. |
| US8877791B2 (en) | 2006-08-04 | 2014-11-04 | Beth Israel Deaconess Medical Center, Inc. | Inhibitors of pyruvate kinase and methods of treating disease |
| US20090247499A1 (en) | 2006-08-21 | 2009-10-01 | Fletcher Joan M | Sulfonylated piperazines as cannabinoid-1 receptor modulators |
| WO2008026658A1 (ja) | 2006-09-01 | 2008-03-06 | Otsuka Chemical Co., Ltd. | N-ピリジルピペリジン化合物、その製造方法及び有害生物防除剤 |
| ES2435430T3 (es) | 2006-10-16 | 2013-12-19 | Thesan Pharmaceuticals, Inc. | Pirazolil tienopiridinas terapéuticas |
| EP2086329B1 (en) | 2006-10-26 | 2014-07-23 | The Arizona Board of Regents on behalf of the University of Arizona | Aquaporin modulators and methods of using them for the treatment of edema and fluid imbalance |
| HUP0600810A3 (en) | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New sulfonamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
| CA2913963A1 (en) | 2006-12-08 | 2008-06-19 | Millenium Pharmaceuticals, Inc. | Unit dose formulations and methods of treating thrombosis with an oral factor xa inhibitor |
| US7897776B2 (en) | 2007-04-23 | 2011-03-01 | Salutria Pharmaceuticals Llc | Sulfonamide containing compounds for treatment of inflammatory disorders |
| MX2010000690A (es) | 2007-07-18 | 2010-06-25 | Janssen Pharmaceutica Nv | Sulfonamidas como moduladores de trpm8. |
| SG183049A1 (en) | 2007-07-20 | 2012-08-30 | Nerviano Medical Sciences Srl | Substituted indazole derivatives active as kinase inhibitors |
| US8552050B2 (en) | 2007-08-16 | 2013-10-08 | Beth Israel Deaconess Medical Center | Activators of pyruvate kinase M2 and methods of treating disease |
| KR20100101580A (ko) | 2007-10-26 | 2010-09-17 | 신젠타 파티서페이션즈 아게 | 신규한 이미다졸 유도체 |
| EP2053045A1 (en) | 2007-10-26 | 2009-04-29 | Syngenta Participations AG | Novel imidazole derivatives |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| ES2620634T3 (es) | 2008-10-09 | 2017-06-29 | The U.S.A. As Represented By The Secretary, Department Of Health And Human Services | Activadores de piruvato quinasa humana |
| JP6067226B2 (ja) * | 2009-03-13 | 2017-01-25 | アジオス ファーマシューティカルズ, インコーポレイテッド | 細胞増殖関連疾患のための方法および組成物 |
| CN102448951B (zh) | 2009-04-06 | 2017-05-10 | 安吉奥斯医药品有限公司 | 丙酮酸激酶m2调节剂、治疗组合物和相关使用方法 |
| EP2427441B1 (en) | 2009-05-04 | 2016-12-14 | Agios Pharmaceuticals, Inc. | Pkm2 activators for use in the treatment of cancer |
| WO2010130638A1 (en) | 2009-05-14 | 2010-11-18 | Evotec Ag | Sulfonamide compounds, pharmaceutical compositions and uses thereof |
| AR077292A1 (es) | 2009-06-29 | 2011-08-17 | Agios Pharmaceuticals Inc | Derivados de piperazin - quinolin sulfonamidas y composiciones farmaceuticas |
| EP2477625A4 (en) | 2009-09-14 | 2012-10-24 | Phusis Therapeutics Inc | PHARMACEUTICAL COMPOSITIONS AND FORMULATIONS COMPRISING PLECKSTRINE HOMOLOGY DOMAIN INHIBITORS AND METHODS OF USE |
| CN105153188B (zh) | 2009-10-22 | 2018-06-01 | 法博太科制药有限公司 | 抗纤维化剂的稠环类似物 |
| JP5967827B2 (ja) | 2009-12-09 | 2016-08-10 | アジオス ファーマシューティカルズ, インコーポレイテッド | Idh変異体をもつことを特徴とする癌治療用の治療的活性化合物 |
| JP2013525438A (ja) | 2010-04-29 | 2013-06-20 | アメリカ合衆国 | ヒトピルビン酸キナーゼ活性剤 |
| CA2801074A1 (en) | 2010-06-04 | 2011-12-08 | Albany Molecular Research, Inc. | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| 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 |
-
2011
- 2011-12-16 EP EP11808773.3A patent/EP2651898B1/en not_active Not-in-force
- 2011-12-16 MX MX2013006900A patent/MX2013006900A/es active IP Right Grant
- 2011-12-16 WO PCT/US2011/065633 patent/WO2012083246A1/en not_active Ceased
- 2011-12-16 US US13/994,398 patent/US9221792B2/en not_active Expired - Fee Related
- 2011-12-16 CA CA2821975A patent/CA2821975A1/en not_active Abandoned
- 2011-12-16 JP JP2013544848A patent/JP5837091B2/ja not_active Expired - Fee Related
- 2011-12-16 ES ES11808773.3T patent/ES2564952T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2651898B1 (en) | 2015-12-09 |
| WO2012083246A1 (en) | 2012-06-21 |
| HK1190405A1 (zh) | 2014-07-04 |
| JP5837091B2 (ja) | 2015-12-24 |
| US9221792B2 (en) | 2015-12-29 |
| US20140073625A1 (en) | 2014-03-13 |
| EP2651898A1 (en) | 2013-10-23 |
| ES2564952T3 (es) | 2016-03-30 |
| MX2013006900A (es) | 2013-10-17 |
| JP2013545823A (ja) | 2013-12-26 |
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