ES2401192T3 - Deazapurinas útiles como inhibidores de janus cinasas - Google Patents
Deazapurinas útiles como inhibidores de janus cinasas Download PDFInfo
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- ES2401192T3 ES2401192T3 ES06815526T ES06815526T ES2401192T3 ES 2401192 T3 ES2401192 T3 ES 2401192T3 ES 06815526 T ES06815526 T ES 06815526T ES 06815526 T ES06815526 T ES 06815526T ES 2401192 T3 ES2401192 T3 ES 2401192T3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Applications Claiming Priority (3)
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| US72256105P | 2005-09-30 | 2005-09-30 | |
| US722561P | 2005-09-30 | ||
| PCT/US2006/037593 WO2007041130A2 (en) | 2005-09-30 | 2006-09-28 | Deazapurines useful as inhibitors of janus kinases |
Publications (2)
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| ES2401192T3 true ES2401192T3 (es) | 2013-04-17 |
| ES2401192T8 ES2401192T8 (es) | 2013-05-10 |
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| ES06815526T Active ES2401192T3 (es) | 2005-09-30 | 2006-09-28 | Deazapurinas útiles como inhibidores de janus cinasas |
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Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI372624B (en) * | 2004-03-30 | 2012-09-21 | Vertex Pharma | Azaindoles useful as inhibitors of jak and other protein kinases |
| WO2006127587A1 (en) * | 2005-05-20 | 2006-11-30 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| EP2270014A1 (en) | 2005-09-22 | 2011-01-05 | Incyte Corporation | Azepine inhibitors of janus kinases |
| EP2455382B1 (en) | 2005-12-13 | 2016-10-26 | Incyte Holdings Corporation | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors |
| TW200801008A (en) * | 2005-12-29 | 2008-01-01 | Abbott Lab | Protein kinase inhibitors |
| CN102532133A (zh) | 2006-01-17 | 2012-07-04 | 沃泰克斯药物股份有限公司 | 适用作詹纳斯激酶抑制剂的吖吲哚类 |
| JP2009532475A (ja) * | 2006-04-05 | 2009-09-10 | バーテックス ファーマシューティカルズ インコーポレイテッド | ヤヌスキナーゼの阻害剤として有用なデアザプリン |
| MX2009002046A (es) | 2006-08-24 | 2009-03-06 | Astrazeneca Ab | Derivados de morfolino pirimidina utiles en el tratamiento de trastornos proliferativos. |
| AU2007338754A1 (en) | 2006-12-21 | 2008-07-03 | Vertex Pharmaceuticals Incorporated | 5-cyan0-4- (pyrrolo [2, 3B] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors |
| EP2121692B1 (en) | 2006-12-22 | 2013-04-10 | Incyte Corporation | Substituted heterocycles as janus kinase inhibitors |
| CN101778825A (zh) * | 2007-03-22 | 2010-07-14 | 沃泰克斯药物股份有限公司 | 适用作詹纳斯激酶抑制剂的n-杂环类化合物 |
| EP3070090B1 (en) | 2007-06-13 | 2018-12-12 | Incyte Holdings Corporation | Use of salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h- pyrazol-1-yl)-3- cyclopentylpropanenitrile |
| CL2008001709A1 (es) | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| CN101809002B (zh) | 2007-07-09 | 2013-03-27 | 阿斯利康(瑞典)有限公司 | 用于与mtor激酶和/或pi3k相关的疾病中的吗啉代嘧啶衍生物 |
| NZ586662A (en) * | 2007-12-19 | 2012-08-31 | Vertex Pharma | PYRAZOLO[1,5-a]PYRIMIDINES USEFUL AS JANUS KINASE 2 INHIBITORS |
| DE102008005493A1 (de) * | 2008-01-22 | 2009-07-23 | Merck Patent Gmbh | 4-(Pyrrolo[2,3-c] pyridine-3-yl)-pyrimidin-2-yl-amin-derivate |
| US8158616B2 (en) | 2008-03-11 | 2012-04-17 | Incyte Corporation | Azetidine and cyclobutane derivatives as JAK inhibitors |
| EP2276750A2 (en) * | 2008-03-27 | 2011-01-26 | Auckland Uniservices Limited | Substituted pyrimidines and triazines and their use in cancer therapy |
| CN102149695B (zh) * | 2008-07-09 | 2015-02-04 | 日产化学工业株式会社 | 异*唑啉取代的苯甲酰胺化合物的制造方法 |
| GB2465405A (en) * | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| JP5775070B2 (ja) | 2009-05-22 | 2015-09-09 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | ヤヌスキナーゼ阻害剤としてのピラゾール−４−イル−ピロロ［２，３−ｄ］ピリミジンおよびピロール−３−イル−ピロロ［２，３−ｄ］ピリミジンのＮ−（ヘテロ）アリール−ピロリジン誘導体 |
| SG176111A1 (en) | 2009-05-22 | 2011-12-29 | Incyte Corp | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]octane- or heptane-nitrile as jak inhibitors |
| RS57869B1 (sr) | 2009-06-17 | 2018-12-31 | Vertex Pharma | Inhibitori replikacije virusa gripa |
| US20120219596A1 (en) | 2009-07-30 | 2012-08-30 | Wendelin Stark | Injectable formulation for treatment and protection of patients having an inflammatory reaction or an ischemia-reperfusion event |
| AR078012A1 (es) | 2009-09-01 | 2011-10-05 | Incyte Corp | Derivados heterociclicos de las pirazol-4-il- pirrolo (2,3-d) pirimidinas como inhibidores de la quinasa janus |
| KR101921850B1 (ko) | 2009-10-09 | 2018-11-23 | 인사이트 홀딩스 코포레이션 | 3-（4-（7Ｈ-피롤로〔2,3-ｄ〕피리미딘-4-일）-1Ｈ-피라졸-1-일）-3-사이클로펜틸프로판니트릴의 하이드록실, 케토 및 글루쿠로나이드 유도체 |
| CA2776028C (en) * | 2009-10-15 | 2015-12-01 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidine compounds |
| UA109775C2 (xx) * | 2009-10-29 | 2015-10-12 | N-вмісні гетероарильні похідні як інгібітори jak3-кінази | |
| ES2461967T3 (es) * | 2009-12-18 | 2014-05-21 | Pfizer Inc. | Compuestos de pirrolo[2,3-d]pirimidina |
| JP2013518112A (ja) * | 2010-01-27 | 2013-05-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | ピラゾロピリジンキナーゼ阻害剤 |
| EP2528917B1 (en) * | 2010-01-27 | 2016-10-19 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridines useful for the treatment of autoimmune, inflammatory or (hyper)proliferative diseases |
| PT3354652T (pt) | 2010-03-10 | 2020-07-20 | Incyte Holdings Corp | Derivados de piperidin-4-ilazetidina como inibidores de jak1 |
| RS54824B1 (sr) | 2010-05-21 | 2016-10-31 | Incyte Holdings Corp | Topikalna formulacija za inhibiciju jak-a |
| SA111320519B1 (ar) | 2010-06-11 | 2014-07-02 | Astrazeneca Ab | مركبات بيريميدينيل للاستخدام كمثبطات atr |
| CA2818542A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| WO2012068440A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| AU2011343642A1 (en) | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| MX2013006840A (es) * | 2010-12-16 | 2014-01-31 | Vertex Pharma | Inhibidores de la replicacion de los virus de la influenza. |
| CA2827673C (en) | 2011-02-18 | 2020-10-27 | Novartis Pharma Ag | Mtor/jak inhibitor combination therapy |
| MY165963A (en) | 2011-06-20 | 2018-05-18 | Incyte Holdings Corp | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| EP2741747A1 (en) | 2011-08-10 | 2014-06-18 | Novartis Pharma AG | JAK P13K/mTOR COMBINATION THERAPY |
| 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 |
| EP2788000B1 (en) * | 2011-12-06 | 2018-05-30 | Merck Sharp & Dohme Corp. | Pyrrolopyrimidines as janus kinase inhibitors |
| TW201406761A (zh) | 2012-05-18 | 2014-02-16 | Incyte Corp | 做爲ｊａｋ抑制劑之哌啶基環丁基取代之吡咯并吡啶及吡咯并嘧啶衍生物 |
| WO2014013014A1 (en) | 2012-07-18 | 2014-01-23 | Fundació Privada Centre De Regulació Genòmica (Crg) | Jak inhibitors for activation of epidermal stem cell populations |
| CN113384546A (zh) | 2012-11-15 | 2021-09-14 | 因赛特公司 | 鲁索利替尼的缓释剂型 |
| WO2014138168A1 (en) | 2013-03-06 | 2014-09-12 | Incyte Corporation | Processes and intermediates for making a jak inhibitor |
| WO2014145576A2 (en) | 2013-03-15 | 2014-09-18 | Northwestern University | Substituted pyrrolo(2,3-d)pyrimidines for the treatment of cancer |
| SG10201801069QA (en) | 2013-08-07 | 2018-03-28 | Incyte Corp | Sustained release dosage forms for a jak1 inhibitor |
| HRP20181272T1 (hr) | 2013-11-13 | 2018-10-05 | Vertex Pharmaceuticals Incorporated | Postupci priprave inhibitora replikacije virusa influence |
| RS59144B1 (sr) | 2013-11-13 | 2019-09-30 | Vertex Pharma | Inhibitori replikacije virusa influence |
| US9498467B2 (en) | 2014-05-30 | 2016-11-22 | Incyte Corporation | Treatment of chronic neutrophilic leukemia (CNL) and atypical chronic myeloid leukemia (aCML) by inhibitors of JAK1 |
| AR101196A1 (es) | 2014-07-16 | 2016-11-30 | Gruenenthal Gmbh | Compuestos de pirimidina sustituidos |
| AR101197A1 (es) * | 2014-07-16 | 2016-11-30 | Gruenenthal Gmbh | Pirimidinas 2,5-sustituidas |
| AR101198A1 (es) | 2014-07-16 | 2016-11-30 | Gruenenthal Gmbh | Pirimidinas 2,5-sustituidas como inhibidores de pde4b |
| TWI679205B (zh) | 2014-09-02 | 2019-12-11 | 日商日本新藥股份有限公司 | 吡唑并噻唑化合物及醫藥 |
| HUE053595T2 (hu) * | 2014-09-08 | 2021-07-28 | Janssen Sciences Ireland Unlimited Co | Pirrolopirimidinek influenzavírus-fertõzésnél történõ alkalmazásra |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| JP6857617B2 (ja) | 2015-05-13 | 2021-04-14 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤 |
| KR20180087290A (ko) | 2015-11-27 | 2018-08-01 | 얀센 사이언시즈 아일랜드 유씨 | 인플루엔자 바이러스 감염에서 사용하기 위한 복소환식 인돌 |
| WO2017125506A1 (en) | 2016-01-20 | 2017-07-27 | Janssen Sciences Ireland Uc | Aryl substituted pyrimidines for use in influenza virus infection |
| WO2017133669A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | 5, 7-diazaindole and 5, 7-diazaindazole derivatives and their use in the treatment, amelioration or prevention of influenza |
| TWI712604B (zh) | 2016-03-01 | 2020-12-11 | 日商日本新藥股份有限公司 | 具jak抑制作用之化合物之結晶 |
| CN109311882B (zh) * | 2016-05-04 | 2022-02-11 | Bci制药公司 | 作为蛋白激酶抑制剂的腺嘌呤衍生物 |
| JP6978097B2 (ja) * | 2016-07-26 | 2021-12-08 | スーヂョウ ロングバイオテック ファーマシューティカルズ カンパニー リミテッドSuzhou Longbiotech Pharmaceuticals Co., Ltd. | Ｊａｋ阻害剤としての複素環化合物、該化合物の塩類および治療への使用 |
| WO2018041989A1 (en) | 2016-09-02 | 2018-03-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing and treating refractory celiac disease type 2 |
| EA039344B1 (ru) * | 2017-01-19 | 2022-01-17 | Сучжоу Лонгбайотек Фармасьютикалз Ко., Лтд. | Гетероциклическое соединение в качестве ингибитора jak и его соли и терапевтическое применение |
| US10927118B2 (en) * | 2017-03-02 | 2021-02-23 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication and uses thereof |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| EA202091830A1 (ru) | 2018-01-30 | 2020-12-29 | Инсайт Корпорейшн | Способы и промежуточные соединения для получения ингибитора jak |
| MD3773593T2 (ro) | 2018-03-30 | 2024-10-31 | Incyte Corp | Tratament hidradenitei supurative utilizând inhibitori ai JAK |
| CN109293640B (zh) * | 2018-10-31 | 2020-05-19 | 青岛清原化合物有限公司 | 一种取代的含氮杂芳环甲酰胺衍生物及其除草组合物和用途 |
| JP2022527972A (ja) | 2019-04-02 | 2022-06-07 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 前悪性病変を有する患者において癌を予測及び予防する方法 |
| US20220202820A1 (en) | 2019-04-16 | 2022-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of jak inhibitors for the treatment of painful conditions involving nav1.7 channels |
| JP7617030B2 (ja) | 2019-05-08 | 2025-01-17 | ビマラン バイオサイエンシーズ，インク． | Ｊａｋ阻害剤 |
| KR20220051351A (ko) | 2019-08-08 | 2022-04-26 | 비말란 바이오사이언스즈, 인크. | Jak 억제제 |
| BR112022005608A2 (pt) * | 2019-09-25 | 2022-09-06 | Vimalan Biosciences Inc | Inibidores de jak |
| CN114761013A (zh) | 2019-09-27 | 2022-07-15 | 迪斯克医药公司 | 治疗骨髓纤维化和相关病症的方法 |
| WO2021231798A1 (en) | 2020-05-13 | 2021-11-18 | Disc Medicine, Inc. | Anti-hemojuvelin (hjv) antibodies for treating myelofibrosis |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| EP4526469A1 (en) | 2022-05-16 | 2025-03-26 | Institut National de la Santé et de la Recherche Médicale | Methods for assessing the exhaustion of hematopoietic stems cells induced by chronic inflammation |
Family Cites Families (10)
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|---|---|---|---|---|
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| DK0970084T3 (da) * | 1997-03-19 | 2003-09-29 | Abbott Gmbh & Co Kg | Pyrrolo[2,3-d]pyrimidiner og deres anvendelse som inhibitorer for tyrosinkinase |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| BR9911365A (pt) | 1998-06-19 | 2001-03-13 | Pfizer Prod Inc | Compostos pirrolo[2,3-d]pirimidina |
| GB0308466D0 (en) * | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| AR045595A1 (es) * | 2003-09-04 | 2005-11-02 | Vertex Pharma | Composiciones utiles como inhibidores de proteinas quinasas |
| WO2005061519A1 (en) * | 2003-12-19 | 2005-07-07 | Takeda San Diego, Inc. | Kinase inhibitors |
| WO2005067546A2 (en) * | 2004-01-13 | 2005-07-28 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
-
2006
- 2006-09-28 ZA ZA200802685A patent/ZA200802685B/xx unknown
- 2006-09-28 NZ NZ567133A patent/NZ567133A/xx not_active IP Right Cessation
- 2006-09-28 ES ES06815526T patent/ES2401192T3/es active Active
- 2006-09-28 SG SG200902181-7A patent/SG151327A1/en unknown
- 2006-09-28 CA CA002623032A patent/CA2623032A1/en not_active Abandoned
- 2006-09-28 WO PCT/US2006/037593 patent/WO2007041130A2/en not_active Ceased
- 2006-09-28 AU AU2006297351A patent/AU2006297351A1/en not_active Abandoned
- 2006-09-28 KR KR1020087010531A patent/KR20080063809A/ko not_active Ceased
- 2006-09-28 RU RU2008117151/04A patent/RU2008117151A/ru not_active Application Discontinuation
- 2006-09-28 CN CN200680039592A patent/CN101801971A/zh active Pending
- 2006-09-28 EP EP06815526A patent/EP1931674B1/en active Active
- 2006-09-28 EP EP12175875A patent/EP2532667A1/en not_active Withdrawn
- 2006-09-28 US US11/528,779 patent/US8580802B2/en not_active Expired - Fee Related
- 2006-09-28 JP JP2008533551A patent/JP2009513571A/ja active Pending
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2008
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- 2008-04-29 NO NO20082026A patent/NO20082026L/no not_active Application Discontinuation
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| US20070207995A1 (en) | 2007-09-06 |
| EP1931674A2 (en) | 2008-06-18 |
| CN101801971A (zh) | 2010-08-11 |
| SG151327A1 (en) | 2009-04-30 |
| NZ567133A (en) | 2011-07-29 |
| AU2006297351A1 (en) | 2007-04-12 |
| IL190249A0 (en) | 2008-11-03 |
| EP1931674B1 (en) | 2012-12-12 |
| ES2401192T8 (es) | 2013-05-10 |
| JP2009513571A (ja) | 2009-04-02 |
| EP2532667A1 (en) | 2012-12-12 |
| NO20082026L (no) | 2008-06-25 |
| ZA200802685B (en) | 2009-10-28 |
| RU2008117151A (ru) | 2009-11-10 |
| US8580802B2 (en) | 2013-11-12 |
| CA2623032A1 (en) | 2007-04-12 |
| KR20080063809A (ko) | 2008-07-07 |
| WO2007041130A3 (en) | 2010-01-21 |
| WO2007041130A2 (en) | 2007-04-12 |
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