CA2711384C - Cytostatic 7-deazapurine nucleosides - Google Patents
Cytostatic 7-deazapurine nucleosides Download PDFInfo
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- CA2711384C CA2711384C CA2711384A CA2711384A CA2711384C CA 2711384 C CA2711384 C CA 2711384C CA 2711384 A CA2711384 A CA 2711384A CA 2711384 A CA2711384 A CA 2711384A CA 2711384 C CA2711384 C CA 2711384C
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02J—CIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
- H02J7/00—Circuit arrangements for charging or depolarising batteries or for supplying loads from batteries
- H02J7/00032—Circuit arrangements for charging or depolarising batteries or for supplying loads from batteries characterised by data exchange
- H02J7/00036—Charger exchanging data with battery
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02J—CIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
- H02J7/00—Circuit arrangements for charging or depolarising batteries or for supplying loads from batteries
- H02J7/00047—Circuit arrangements for charging or depolarising batteries or for supplying loads from batteries with provisions for charging different types of batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Power Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2224708P | 2008-01-18 | 2008-01-18 | |
| US61/022,247 | 2008-01-18 | ||
| PCT/CZ2009/000004 WO2009089804A1 (en) | 2008-01-18 | 2009-01-15 | Novel cytostatic 7-deazapurine nucleosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2711384A1 CA2711384A1 (en) | 2009-07-23 |
| CA2711384C true CA2711384C (en) | 2016-07-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2711384A Active CA2711384C (en) | 2008-01-18 | 2009-01-15 | Cytostatic 7-deazapurine nucleosides |
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|---|---|
| US (1) | US8093226B2 (enExample) |
| EP (2) | EP3133080B1 (enExample) |
| JP (2) | JP5485172B2 (enExample) |
| CN (1) | CN101977923B (enExample) |
| AU (1) | AU2009204568B2 (enExample) |
| CA (1) | CA2711384C (enExample) |
| CY (2) | CY1118104T1 (enExample) |
| DK (2) | DK3133080T3 (enExample) |
| ES (2) | ES2598503T3 (enExample) |
| HR (2) | HRP20161344T1 (enExample) |
| HU (2) | HUE041598T2 (enExample) |
| LT (2) | LT2231689T (enExample) |
| NZ (1) | NZ586610A (enExample) |
| PL (2) | PL2231689T3 (enExample) |
| PT (2) | PT3133080T (enExample) |
| SI (2) | SI3133080T1 (enExample) |
| TR (1) | TR201815961T4 (enExample) |
| WO (1) | WO2009089804A1 (enExample) |
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| DK3184526T3 (en) | 2005-12-13 | 2019-01-14 | Incyte Holdings Corp | PYRROLO [2,3-D] PYRIMIDINE DERIVATIVES AS A JANUS-KINASE INHIBITOR |
| EP2740731B1 (en) | 2007-06-13 | 2016-03-23 | Incyte Holdings Corporation | Crystalline salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| CL2009001884A1 (es) * | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| EP2421879B1 (en) * | 2009-04-22 | 2013-09-04 | Institute Of Organic Chemistry And Biochemistry As CR, V.V.I. | Novel 7-deazapurine nucleosides for therapeutic uses |
| ES2487542T3 (es) * | 2009-05-22 | 2014-08-21 | Incyte Corporation | Derivados de N-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo[2,3-d]pirimidinas y pirrol-3-il-pirrolo[2,3-d]pirimidinas como inhibidores de cinasas Janus |
| WO2010135621A1 (en) * | 2009-05-22 | 2010-11-25 | Incyte Corporation | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]octane- or heptane-nitrile as jak inhibitors |
| WO2011028685A1 (en) | 2009-09-01 | 2011-03-10 | Incyte Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| SMT201800137T1 (it) | 2010-03-10 | 2018-07-17 | Incyte Holdings Corp | Derivati di piperidin-4-il azetidina come inibitori di jak1 |
| PH12012502296B1 (en) | 2010-05-21 | 2017-10-06 | Incyte Holdings Corp | Topical formulation for a jak inhibitor |
| CN103221048A (zh) * | 2010-11-18 | 2013-07-24 | 卡斯纳莱拉创新药物私人有限公司 | 取代的4-(硒吩-2(或3)-基氨基)嘧啶化合物及其使用方法 |
| ES2536415T3 (es) | 2010-11-19 | 2015-05-25 | Incyte Corporation | Pirrolopiridinas y pirrolopirimidinas sustituidas heterocíclicas como inhibidores de JAK |
| SG190839A1 (en) | 2010-11-19 | 2013-07-31 | Incyte Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| WO2012177606A1 (en) | 2011-06-20 | 2012-12-27 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| WO2013173720A1 (en) | 2012-05-18 | 2013-11-21 | Incyte Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| PE20151157A1 (es) | 2012-11-15 | 2015-08-19 | Incyte Corp | Formas de dosificacion de ruxolitinib de liberacion sostenida |
| LT3489239T (lt) | 2013-03-06 | 2022-03-10 | Incyte Holdings Corporation | Jak inhibitoriaus gamybos būdai ir tarpiniai junginiai |
| UA120499C2 (uk) | 2013-08-07 | 2019-12-26 | Інсайт Корпорейшн | Лікування захворювань із застосуванням лікарських форм з уповільненим вивільненням для інгібітора jak1 |
| WO2015184305A1 (en) | 2014-05-30 | 2015-12-03 | Incyte Corporation | TREATMENT OF CHRONIC NEUTROPHILIC LEUKEMIA (CNL) AND ATYPICAL CHRONIC MYELOID LEUKEMIA (aCML) BY INHIBITORS OF JAK1 |
| WO2018001393A1 (en) | 2016-06-29 | 2018-01-04 | Ustav Organicke Chemie A Biochemie Av Cr, V.V.I. | Substituted thienopyrrolopyrimidine ribonucleosides for therapeutic use |
| CZ307334B6 (cs) | 2016-08-02 | 2018-06-13 | Ăšstav organickĂ© chemie a biochemie AV ÄŚR, v.v.i. | Substituované heteropentadieno-pyrrolopyrimidinové ribonukleosidy pro terapeutické použití |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| IL276302B2 (en) | 2018-01-30 | 2023-11-01 | Incyte Corp | Procedures for preparing [1-(3-fluoro-2-(trifluoromethyl(isonicotinyl}piperidine-4-one) |
| CZ308104B6 (cs) | 2018-03-12 | 2020-01-08 | Ăšstav organickĂ© chemie a biochemie AV ÄŚR, v. v. i. | Pyridinopyrrolopyrimidinové ribonukleosidy pro terapeutické použití |
| SMT202400306T1 (it) | 2018-03-30 | 2024-09-16 | Incyte Corp | Trattamento dell'idrosadenite suppurativa utilizzando inibitori di jak. |
| EP3952874A4 (en) * | 2019-04-05 | 2022-12-28 | Prelude Therapeutics, Incorporated | SELECTIVE INHIBITORS OF PROTEIN ARGININE METHYLTRANSFERASE 5 |
| JP7354246B2 (ja) * | 2019-06-18 | 2023-10-02 | 大鵬薬品工業株式会社 | ピロロピリミジン骨格を有する新規なリン酸エステル化合物又はその薬学的に許容可能な塩 |
| WO2021164848A1 (en) * | 2020-02-17 | 2021-08-26 | Katholieke Universiteit Leuven | Novel 6-substituted 7-deazapurines and corresponding nucleosides as medicaments |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| CN112190590A (zh) * | 2020-11-06 | 2021-01-08 | 牡丹江医学院 | 一种治疗动脉粥样硬化的硒核苷及其药物组合物 |
Family Cites Families (11)
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| JPS50125033A (enExample) * | 1974-03-19 | 1975-10-01 | ||
| IL108523A0 (en) * | 1993-02-03 | 1994-05-30 | Gensia Inc | Pharmaceutical compositions containing adenosine kinase inhibitors for preventing or treating conditions involving inflammatory responses and pain |
| JPH10158293A (ja) * | 1996-08-08 | 1998-06-16 | Rikagaku Kenkyusho | ３’−デオキシリボヌクレオチド誘導体 |
| JP3318579B2 (ja) * | 1997-07-07 | 2002-08-26 | 理化学研究所 | Ｄｎａの塩基配列決定方法 |
| JP3489991B2 (ja) * | 1997-07-07 | 2004-01-26 | 理化学研究所 | ３’−デオキシリボヌクレオチド誘導体 |
| CZ9901996A3 (cs) * | 1999-06-04 | 2001-01-17 | Ústav organické chemie a biochemie AV ČR | Nové 6-fenylpurinové 9-ß-D-ribonukleosidy s antineoplastickým účinkem, jejich použití k přípravě farmaceutických preparátů a farmaceutické přípravky, které je obsahují |
| WO2003051899A1 (en) * | 2001-12-17 | 2003-06-26 | Ribapharm Inc. | Deazapurine nucleoside libraries and compounds |
| KR20060123707A (ko) * | 2003-08-27 | 2006-12-04 | 바이오타, 인코포레이티드 | 치료제로서의 신규 트리시클릭 뉴클레오시드 또는뉴클레오티드 |
| WO2006065335A2 (en) | 2004-10-21 | 2006-06-22 | Merck & Co., Inc. | Fluorinated pyrrolo[2,3-d]pyrimidine nucleosides for the treatment of rna-dependent rna viral infection |
| CN101043893A (zh) * | 2004-10-21 | 2007-09-26 | 默克公司 | 治疗RNA－依赖性RNA病毒感染的氟化吡咯并[2,3－d]嘧啶核苷 |
| WO2006116557A1 (en) * | 2005-04-25 | 2006-11-02 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
-
2009
- 2009-01-15 PT PT16174985T patent/PT3133080T/pt unknown
- 2009-01-15 HR HRP20161344TT patent/HRP20161344T1/hr unknown
- 2009-01-15 LT LTEP09702842.7T patent/LT2231689T/lt unknown
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