CA2987743A1 - Purine derivatives and their use as immunosuppressive agents - Google Patents
Purine derivatives and their use as immunosuppressive agents Download PDFInfo
- Publication number
- CA2987743A1 CA2987743A1 CA2987743A CA2987743A CA2987743A1 CA 2987743 A1 CA2987743 A1 CA 2987743A1 CA 2987743 A CA2987743 A CA 2987743A CA 2987743 A CA2987743 A CA 2987743A CA 2987743 A1 CA2987743 A1 CA 2987743A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- piperazin
- alkyl
- heterocyclic
- substituted
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0904373A GB0904373D0 (en) | 2009-03-13 | 2009-03-13 | Novel thienopyrimidines |
| GB0904353A GB0904353D0 (en) | 2009-03-13 | 2009-03-13 | Novel thiazolopyrimidines |
| GB0904373.8 | 2009-03-13 | ||
| GB0904353.0 | 2009-03-13 | ||
| GB0911022A GB0911022D0 (en) | 2009-06-26 | 2009-06-26 | Novel purines |
| GB0911022.2 | 2009-06-26 | ||
| CA2754890A CA2754890C (en) | 2009-03-13 | 2010-03-15 | Bicyclic heterocycles |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2754890A Division CA2754890C (en) | 2009-03-13 | 2010-03-15 | Bicyclic heterocycles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2987743A1 true CA2987743A1 (en) | 2010-09-16 |
Family
ID=42181129
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2987743A Abandoned CA2987743A1 (en) | 2009-03-13 | 2010-03-15 | Purine derivatives and their use as immunosuppressive agents |
| CA2754890A Expired - Fee Related CA2754890C (en) | 2009-03-13 | 2010-03-15 | Bicyclic heterocycles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2754890A Expired - Fee Related CA2754890C (en) | 2009-03-13 | 2010-03-15 | Bicyclic heterocycles |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8901132B2 (enExample) |
| EP (2) | EP2923734B1 (enExample) |
| JP (2) | JP5647998B2 (enExample) |
| CA (2) | CA2987743A1 (enExample) |
| ES (2) | ES2543216T3 (enExample) |
| WO (1) | WO2010103130A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE039815T2 (hu) | 2006-07-05 | 2019-02-28 | Fibrotech Therapeutics Pty Ltd | Gyógyhatású vegyületek |
| EP2923734B1 (en) * | 2009-03-13 | 2018-01-10 | Katholieke Universiteit Leuven, K.U. Leuven R&D | Purine analogues and their use as immunosuppressive agents |
| 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 |
| GB201012889D0 (en) * | 2010-08-02 | 2010-09-15 | Univ Leuven Kath | Antiviral activity of novel bicyclic heterocycles |
| GB201015411D0 (en) * | 2010-09-15 | 2010-10-27 | Univ Leuven Kath | Anti-cancer activity of novel bicyclic heterocycles |
| GB201114212D0 (en) | 2011-08-18 | 2011-10-05 | Ucb Pharma Sa | Therapeutic agents |
| GB201115665D0 (en) | 2011-09-09 | 2011-10-26 | Univ Leuven Kath | Autoimmune and inflammatory disorder therapy |
| US20130102601A1 (en) | 2011-10-21 | 2013-04-25 | F. Hoffmann-La Roche Ltd | Pyrimidin-4-one derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| GB201119401D0 (en) | 2011-11-10 | 2011-12-21 | Ucb Pharma Sa | Therapeutic agents |
| GB201217704D0 (en) | 2012-10-03 | 2012-11-14 | Ucb Pharma Sa | Therapeutic agents |
| HRP20181008T1 (hr) * | 2012-12-20 | 2018-08-24 | Ucb Biopharma Sprl | Terapeutski aktivni pirazolo-pirimidin derivati |
| CN103044460B (zh) * | 2013-01-30 | 2015-02-25 | 石家庄学院 | 3,5,7-三苯基-5H-噻唑并[3,2-a]嘧啶类衍生物及应用 |
| EA201591930A1 (ru) * | 2013-04-05 | 2016-02-29 | Полихем С.А. | Применение пидотимода для лечения воспалительных заболеваний кишечника |
| JP2016531870A (ja) * | 2013-09-27 | 2016-10-13 | ニンバス アイリス, インコーポレイテッド | Irak阻害剤およびその使用 |
| TWI648281B (zh) | 2013-10-17 | 2019-01-21 | 日商安斯泰來製藥股份有限公司 | 含硫二環式化合物 |
| CN104892589A (zh) * | 2014-03-07 | 2015-09-09 | 中国科学院上海药物研究所 | 一类杂环化合物、其制备方法和用途 |
| GB201410817D0 (en) | 2014-06-17 | 2014-07-30 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R & D | Therapeutic agents |
| WO2016012536A1 (en) * | 2014-07-23 | 2016-01-28 | Katholieke Universiteit Leuven | Gak modulators as antivirals |
| UY36390A (es) | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen |
| EA201790806A1 (ru) | 2014-11-05 | 2017-11-30 | Флексус Байосайенсиз, Инк. | Иммунорегулирующие средства |
| GB201517263D0 (en) | 2015-09-30 | 2015-11-11 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven | Therapeutic agents |
| GB201521767D0 (en) | 2015-12-10 | 2016-01-27 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R&D | Therapeutic agents |
| WO2018144620A1 (en) | 2017-02-03 | 2018-08-09 | Shire Human Genetic Therapies, Inc. | Anti-fibrotic compounds |
| CN112752761B (zh) | 2018-08-21 | 2024-03-29 | 杏林制药株式会社 | 双环杂芳族环衍生物 |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US2512572A (en) | 1950-06-20 | Substituted pteridines and method | ||
| BE791242A (fr) * | 1971-11-11 | 1973-05-10 | Thomae Gmbh Dr K | Nouvelles thiazolo(5,4-d)pyrimidines |
| US4127118B1 (en) | 1977-03-16 | 1995-12-19 | Alvaro Latorre | Method of effecting and enhancing an erection |
| ZA857647B (en) * | 1984-10-12 | 1986-05-28 | Warner Lambert Co | Purine derivatives |
| US5057517A (en) * | 1987-07-20 | 1991-10-15 | Merck & Co., Inc. | Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents |
| IL87149A (en) * | 1987-07-20 | 1994-05-30 | Merck & Co Inc | 6-Piperazinyl derivatives of purine and its 3- and 9-deaza isosteres, their preparation and pharmaceutical compositions containing them |
| GB9221220D0 (en) | 1992-10-09 | 1992-11-25 | Sandoz Ag | Organic componds |
| US5780462A (en) | 1995-12-27 | 1998-07-14 | American Home Products Corporation | Water soluble rapamycin esters |
| JP2001097979A (ja) * | 1999-07-28 | 2001-04-10 | Takeda Chem Ind Ltd | 縮合複素環化合物、その製造法および用途 |
| US6331547B1 (en) | 1999-08-18 | 2001-12-18 | American Home Products Corporation | Water soluble SDZ RAD esters |
| WO2001058906A1 (en) | 2000-02-11 | 2001-08-16 | Astrazeneca Ab | Pyrimidine compounds and their use as modulators of chemokine receptor activity |
| US6440991B1 (en) | 2000-10-02 | 2002-08-27 | Wyeth | Ethers of 7-desmethlrapamycin |
| JP2004028376A (ja) | 2002-06-21 | 2004-01-29 | Hino Motors Ltd | Egrクーラ |
| EP1556140A4 (en) * | 2002-10-15 | 2006-04-19 | Synta Pharmaceuticals Corp | NEW COMPOUNDS |
| RU2328498C9 (ru) * | 2002-12-04 | 2008-12-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Соединения с конденсированным 1,3-дигидроимидазольным циклом |
| ES2217956B1 (es) * | 2003-01-23 | 2006-04-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| CA2528848C (en) | 2003-06-11 | 2012-09-04 | Xention Discovery Limited | Thienopyrimidine derivatives as potassium channel inhibitors |
| DE10348023A1 (de) * | 2003-10-15 | 2005-05-19 | Imtm Gmbh | Neue Alanyl-Aminopeptidasen-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| EP1731523A4 (en) | 2004-04-01 | 2009-08-12 | Takeda Pharmaceutical | THIAZOLOPYRIMIDINDERIVAT |
| GB0407723D0 (en) * | 2004-04-05 | 2004-05-12 | Novartis Ag | Organic compounds |
| US7576080B2 (en) | 2004-12-23 | 2009-08-18 | Memory Pharmaceuticals Corporation | Certain thienopyrimidine derivatives as phosphodiesterase 10 inhibitors |
| FR2880626B1 (fr) * | 2005-01-13 | 2008-04-18 | Aventis Pharma Sa | Derives de la purine, compositions les contenant et utilisation |
| EP1844052A1 (en) * | 2005-01-26 | 2007-10-17 | Pharmacia & Upjohn Company LLC | Thieno[2,3-d]pyrimidine compounds as inhibitors of adp-mediated platelets aggregation |
| WO2007004688A1 (ja) | 2005-07-01 | 2007-01-11 | Nippon Chemiphar Co., Ltd. | キサンチンオキシダーゼ阻害剤 |
| GB0526246D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| US20080108611A1 (en) | 2006-01-19 | 2008-05-08 | Battista Kathleen A | Substituted thienopyrimidine kinase inhibitors |
| KR100846988B1 (ko) | 2006-03-06 | 2008-07-16 | 제일약품주식회사 | 신규한 티에노피리미딘 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 함유하는 약학조성물 |
| WO2007127183A1 (en) * | 2006-04-26 | 2007-11-08 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them |
| CN101448844B (zh) | 2006-05-18 | 2012-07-25 | 霍夫曼-拉罗奇有限公司 | 作为腺苷a2b受体拮抗剂的噻唑并嘧啶/吡啶脲衍生物 |
| WO2008005303A2 (en) * | 2006-06-30 | 2008-01-10 | Janssen Pharmaceutica N.V. | Thiazolopyrimidine modulators of trpv1 |
| DE602007009998D1 (de) | 2006-08-08 | 2010-12-02 | Millennium Pharm Inc | Heteroarylverbindungen als hemmer der e1-aktivierenden enzyme |
| WO2008057402A2 (en) | 2006-11-02 | 2008-05-15 | Cytovia, Inc. | N-aryl-isoxazolopyrimidin-4-amines and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| BRPI0622030A2 (pt) | 2006-11-16 | 2014-04-22 | Pharmacopeia Llc | Derivados de purina 7-substituída, para imunossupressão |
| WO2008059368A2 (en) | 2006-11-17 | 2008-05-22 | Pfizer Products Inc. | Fused 2-amino pyrimidine compounds and their use for the treatment of cancer |
| CA2671845C (en) * | 2006-12-07 | 2015-03-24 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| KR20090101281A (ko) | 2007-01-23 | 2009-09-24 | 팔라우 파르마 에스에이 | 퓨린 유도체 |
| WO2008094737A2 (en) | 2007-01-26 | 2008-08-07 | Irm Llc | Purine compounds and compositions as kinase inhibitors for the treatment of plasmodium related diseases |
| WO2008135232A1 (en) | 2007-05-02 | 2008-11-13 | Riccardo Cortese | Use and compositions of purine derivatives for the treatment of proliferative disorders |
| CN101679456B (zh) * | 2007-06-12 | 2012-09-05 | 霍夫曼-拉罗奇有限公司 | 噻唑并嘧啶类和它们作为磷脂酰肌醇3-激酶的抑制剂的应用 |
| CN101784548B (zh) | 2007-06-29 | 2013-07-17 | 吉里德科学公司 | 嘌呤衍生物及其作为toll样受体7的调节剂的用途 |
| WO2009013545A2 (en) * | 2007-07-26 | 2009-01-29 | Astrazeneca Ab | Chemical compounds |
| WO2009027732A1 (en) * | 2007-08-24 | 2009-03-05 | Astrazeneca Ab | 5-6-bicyclic heteroaromatic compounds with antibacterial activity |
| ES2399774T3 (es) * | 2007-09-24 | 2013-04-03 | Genentech, Inc. | Compuestos de tiazolopirimidina inhibidores de PI3K y métodos de uso |
| UA104010C2 (en) * | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| EP2923734B1 (en) * | 2009-03-13 | 2018-01-10 | Katholieke Universiteit Leuven, K.U. Leuven R&D | Purine analogues and their use as immunosuppressive agents |
| AR080711A1 (es) * | 2010-03-31 | 2012-05-02 | Lilly Co Eli | Compuesto de piperazin-purina composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento o prevencion del dolor |
-
2010
- 2010-03-15 EP EP15162142.2A patent/EP2923734B1/en not_active Not-in-force
- 2010-03-15 US US13/255,429 patent/US8901132B2/en not_active Expired - Fee Related
- 2010-03-15 ES ES10711871.3T patent/ES2543216T3/es active Active
- 2010-03-15 CA CA2987743A patent/CA2987743A1/en not_active Abandoned
- 2010-03-15 EP EP20100711871 patent/EP2405973B1/en active Active
- 2010-03-15 WO PCT/EP2010/053318 patent/WO2010103130A2/en not_active Ceased
- 2010-03-15 ES ES15162142.2T patent/ES2665277T3/es active Active
- 2010-03-15 CA CA2754890A patent/CA2754890C/en not_active Expired - Fee Related
- 2010-03-15 JP JP2011553476A patent/JP5647998B2/ja not_active Expired - Fee Related
-
2014
- 2014-10-20 US US14/518,480 patent/US9221822B2/en not_active Expired - Fee Related
- 2014-11-10 JP JP2014228403A patent/JP6021880B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2405973A2 (en) | 2012-01-18 |
| US8901132B2 (en) | 2014-12-02 |
| ES2665277T3 (es) | 2018-04-25 |
| EP2923734A1 (en) | 2015-09-30 |
| US20120046278A1 (en) | 2012-02-23 |
| CA2754890C (en) | 2018-01-16 |
| CA2754890A1 (en) | 2010-09-16 |
| JP2012520269A (ja) | 2012-09-06 |
| JP5647998B2 (ja) | 2015-01-07 |
| EP2923734B1 (en) | 2018-01-10 |
| JP2015028088A (ja) | 2015-02-12 |
| EP2405973B1 (en) | 2015-04-22 |
| US20150038494A1 (en) | 2015-02-05 |
| ES2543216T3 (es) | 2015-08-17 |
| WO2010103130A2 (en) | 2010-09-16 |
| US9221822B2 (en) | 2015-12-29 |
| WO2010103130A3 (en) | 2010-12-23 |
| JP6021880B2 (ja) | 2016-11-09 |
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| FZDE | Discontinued |
Effective date: 20221007 |