CA2680467C - Inhibitors of histone deacetylase - Google Patents
Inhibitors of histone deacetylase Download PDFInfo
- Publication number
- CA2680467C CA2680467C CA2680467A CA2680467A CA2680467C CA 2680467 C CA2680467 C CA 2680467C CA 2680467 A CA2680467 A CA 2680467A CA 2680467 A CA2680467 A CA 2680467A CA 2680467 C CA2680467 C CA 2680467C
- Authority
- CA
- Canada
- Prior art keywords
- hydrocarbyl
- optionally substituted
- group
- compound
- alkyl
- 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.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90673307P | 2007-03-13 | 2007-03-13 | |
| US60/906,733 | 2007-03-13 | ||
| US12/043,450 US8030344B2 (en) | 2007-03-13 | 2008-03-06 | Inhibitors of histone deacetylase |
| US12/043,450 | 2008-03-06 | ||
| PCT/CA2008/000455 WO2008109994A1 (en) | 2007-03-13 | 2008-03-12 | Inhibitors of histone deacetylase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2680467A1 CA2680467A1 (en) | 2008-09-18 |
| CA2680467C true CA2680467C (en) | 2016-11-08 |
Family
ID=39758948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2680467A Expired - Fee Related CA2680467C (en) | 2007-03-13 | 2008-03-12 | Inhibitors of histone deacetylase |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8030344B2 (OSRAM) |
| EP (1) | EP2134680B1 (OSRAM) |
| JP (2) | JP2010520893A (OSRAM) |
| KR (2) | KR20150080025A (OSRAM) |
| CN (1) | CN101679239B (OSRAM) |
| CA (1) | CA2680467C (OSRAM) |
| ES (1) | ES2565243T3 (OSRAM) |
| TW (1) | TWI549676B (OSRAM) |
| WO (1) | WO2008109994A1 (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8030344B2 (en) * | 2007-03-13 | 2011-10-04 | Methylgene Inc. | Inhibitors of histone deacetylase |
| RU2501787C2 (ru) * | 2007-11-02 | 2013-12-20 | Метилджен Инк. | Ингибиторы гистондеацетилазы |
| ES2620027T3 (es) | 2008-09-03 | 2017-06-27 | Biomarin Pharmaceutical Inc. | Composiciones que incluyen derivados del ácido 6-aminohexanoico como inhibidores de HDAC |
| KR20110117194A (ko) * | 2009-02-23 | 2011-10-26 | 에프. 호프만-라 로슈 아게 | 암 치료를 위한 신규한 오르토-아미노아미드 |
| NZ599757A (en) | 2009-10-30 | 2014-08-29 | Massachusetts Inst Technology | The use of ci-994 and dinaline for the treatment of memory/cognition and anxiety disorders |
| WO2012068589A2 (en) * | 2010-11-19 | 2012-05-24 | Constellation Pharmaceuticals | Modulators of methyl modifying enzymes, compositions and uses thereof |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| CN102775368B (zh) * | 2011-05-10 | 2016-08-17 | 上海驺虞医药科技有限公司 | 一类噻唑类化合物及其制备方法和用途 |
| EP2780013A4 (en) | 2011-11-18 | 2015-07-01 | Constellation Pharmaceuticals Inc | MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF |
| US9206128B2 (en) | 2011-11-18 | 2015-12-08 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| US9085583B2 (en) | 2012-02-10 | 2015-07-21 | Constellation—Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| EP2970305B1 (en) | 2013-03-15 | 2017-02-22 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| KR20150132345A (ko) | 2013-03-15 | 2015-11-25 | 바이오마린 파머수티컬 인크. | Hdac 저해제 |
| WO2015023915A1 (en) | 2013-08-15 | 2015-02-19 | Constellation Pharmaceuticals, Inc. | Indole derivatives as modulators of methyl modifying enzymes, compositions and uses thereof |
| US9274117B2 (en) * | 2013-12-21 | 2016-03-01 | Catholic University Industry Academic | Use of SIRT7 as novel cancer therapy target and method for treating cancer using the same |
| US9636298B2 (en) | 2014-01-17 | 2017-05-02 | Methylgene Inc. | Prodrugs of compounds that enhance antifungal activity and compositions of said prodrugs |
| GB201501870D0 (en) * | 2015-02-04 | 2015-03-18 | Cancer Rec Tech Ltd | Autotaxin inhibitors |
| CA2990660A1 (en) * | 2015-07-02 | 2017-01-05 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10577350B2 (en) | 2015-08-28 | 2020-03-03 | Constellation Pharmaceuticals, Inc. | Crystalline forms of (R)-N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)ethyl)-1H-indole-3-carboxamide |
| WO2018075598A1 (en) | 2016-10-19 | 2018-04-26 | Constellation Pharmaceuticals, Inc. | Synthesis of inhibitors of ezh2 |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2754286A (en) | 1951-10-15 | 1956-07-10 | Du Pont | Aldehydes and their acetals |
| CH431764A (de) | 1959-05-06 | 1967-03-15 | Sandoz Ag | Verfahren zur Herstellung metallhaltiger Reaktivfarbstoffe |
| US3263924A (en) | 1963-09-13 | 1966-08-02 | Dole Valve Co | Heating and cooling zone valve |
| US4994479A (en) | 1985-04-03 | 1991-02-19 | Yamanouchi Pharmaceutical Co., Ltd. | Phenylene derivatives and anti-allergic use thereof |
| US5149797A (en) | 1990-02-15 | 1992-09-22 | The Worcester Foundation For Experimental Biology | Method of site-specific alteration of rna and production of encoded polypeptides |
| US5332750A (en) | 1991-09-04 | 1994-07-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 1,2-dihydro-2-oxopyridines |
| US5652355A (en) | 1992-07-23 | 1997-07-29 | Worcester Foundation For Experimental Biology | Hybrid oligonucleotide phosphorothioates |
| DE19510957A1 (de) | 1995-03-25 | 1996-09-26 | Huels Chemische Werke Ag | Eingedickter Bodenverfestiger, sowie diesen enthaltende verpackte Fertigmischung für Bodenbehandlungen |
| US6174905B1 (en) | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| JP4105451B2 (ja) | 1996-09-30 | 2008-06-25 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | 分化誘導剤 |
| US6794392B1 (en) | 1996-09-30 | 2004-09-21 | Schering Aktiengesellschaft | Cell differentiation inducer |
| US6034251A (en) | 1997-11-07 | 2000-03-07 | Schering Corporation | Phenyl-alkyl-imidazoles |
| US5905084A (en) * | 1997-11-14 | 1999-05-18 | Eli Lilly And Company | 5-HTIF -agonists effective in treating migraine |
| JPH11318492A (ja) | 1998-03-09 | 1999-11-24 | Aisin Seiki Co Ltd | 蛍光発生性基質を含有する組成物 |
| JPH11269146A (ja) | 1998-03-24 | 1999-10-05 | Mitsui Chem Inc | 分化誘導剤 |
| JP4405602B2 (ja) | 1998-04-16 | 2010-01-27 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | ヒストン脱アセチル化酵素阻害剤 |
| JP2000256194A (ja) | 1999-01-06 | 2000-09-19 | Mitsui Chemicals Inc | 核内レセプタ作動薬およびその効果増強剤 |
| US6653309B1 (en) | 1999-04-26 | 2003-11-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme technical field of the invention |
| JP2003500052A (ja) | 1999-05-03 | 2003-01-07 | メチルジーン インコーポレイテッド | ヒストン脱アセチル酵素の抑制 |
| JP4360660B2 (ja) | 1999-11-09 | 2009-11-11 | 三井化学株式会社 | モノアシルフェニレンジアミン誘導体の精製法 |
| US6541661B1 (en) | 1999-11-23 | 2003-04-01 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| AU2001241128A1 (en) | 2000-03-14 | 2001-09-24 | Fujisawa Pharmaceutical Co. Ltd. | Novel amide compounds |
| ATE489360T1 (de) | 2000-03-24 | 2010-12-15 | Methylgene Inc | Inhibitoren der histon-deacetylase |
| KR20040018328A (ko) | 2001-01-12 | 2004-03-03 | 메틸진, 인크. | 히스톤 디아세틸라제-4를 특이적으로 억제하는 방법 |
| US7868204B2 (en) | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US6897220B2 (en) | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| CA2465978C (en) | 2001-09-14 | 2015-04-07 | Soon Hyung Woo | Inhibitors of histone deacetylase |
| CA2473505A1 (en) * | 2002-02-07 | 2003-08-14 | Ellen M. Leahy | Novel bicyclic hydroxamates as inhibitors of histone deacetylase |
| AU2003218735B2 (en) | 2002-03-13 | 2009-03-12 | Janssen Pharmaceutica N.V. | Piperazinyl-, piperidinyl- and morpholinyl-derivatives as novel inhibitors of histone deacetylase |
| PL205531B1 (pl) | 2002-03-13 | 2010-04-30 | Janssen Pharmaceutica Nv | Pochodna karbonyloaminowa, jej zastosowanie i sposób wytwarzania oraz kompozycja farmaceutyczna |
| EA006707B1 (ru) | 2002-03-13 | 2006-02-24 | Янссен Фармацевтика Н. В. | Сульфонилпроизводные в качестве новых ингибиторов гистон-деацетилазы |
| OA12790A (en) | 2002-03-13 | 2006-07-10 | Janssen Pharmaceutica Nv | New inhibitors of histone deacetylase. |
| CN1305850C (zh) | 2002-03-13 | 2007-03-21 | 詹森药业有限公司 | 作为组蛋白脱乙酰酶新颖抑制剂的磺酰基氨基衍生物 |
| CN100451001C (zh) | 2002-03-14 | 2009-01-14 | 日本曹达株式会社 | 酚性化合物及使用酚性化合物的记录材料 |
| TWI319387B (en) | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| GB0209715D0 (en) * | 2002-04-27 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| US20040072770A1 (en) | 2002-07-03 | 2004-04-15 | Besterman Jeffrey M. | Methods for specifically inhibiting histone deacetylase-7 and 8 |
| KR20050074487A (ko) | 2002-10-17 | 2005-07-18 | 메틸진, 인크. | 히스톤 데아세틸라아제의 억제제 |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| AR043633A1 (es) | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
| WO2005030705A1 (en) | 2003-09-24 | 2005-04-07 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7253204B2 (en) | 2004-03-26 | 2007-08-07 | Methylgene Inc. | Inhibitors of histone deacetylase |
| WO2005092899A1 (en) | 2004-03-26 | 2005-10-06 | Methylgene Inc. | Inhibitors of histone deacetylase |
| CA2581356A1 (en) | 2004-09-22 | 2006-03-22 | Methylgene Inc. | Histone deacetylase whole cell enzyme assay |
| EP1824831A2 (en) * | 2004-12-16 | 2007-08-29 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| JP4853824B2 (ja) * | 2005-01-20 | 2012-01-11 | アステラス製薬株式会社 | キノロン誘導体を有効成分とする医薬組成物 |
| AU2006240258A1 (en) * | 2005-04-20 | 2006-11-02 | Merck Sharp & Dohme Corp. | Benzothiophene derivatives |
| JP2008540574A (ja) | 2005-05-11 | 2008-11-20 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| US8138198B2 (en) * | 2005-05-18 | 2012-03-20 | Angibaud Patrick Rene | Substituted aminopropenyl piperidine or morpholine derivatives as novel inhibitors of histone deacetylase |
| CN101263121A (zh) * | 2005-07-14 | 2008-09-10 | 塔克达圣地亚哥公司 | 组蛋白脱乙酰基酶抑制剂 |
| AU2006312084A1 (en) * | 2005-11-03 | 2007-05-18 | Merck Sharp & Dohme Corp. | Substituted nicotinamide compounds |
| AR057579A1 (es) * | 2005-11-23 | 2007-12-05 | Merck & Co Inc | Compuestos espirociclicos como inhibidores de histona de acetilasa (hdac) |
| EP1976835A2 (en) | 2006-01-13 | 2008-10-08 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| JP5554988B2 (ja) | 2006-04-07 | 2014-07-23 | メチルジーン インコーポレイテッド | ヒストンデアセチラーゼの阻害剤 |
| US8030344B2 (en) * | 2007-03-13 | 2011-10-04 | Methylgene Inc. | Inhibitors of histone deacetylase |
-
2008
- 2008-03-06 US US12/043,450 patent/US8030344B2/en active Active
- 2008-03-12 CN CN200880015207.9A patent/CN101679239B/zh not_active Expired - Fee Related
- 2008-03-12 WO PCT/CA2008/000455 patent/WO2008109994A1/en not_active Ceased
- 2008-03-12 CA CA2680467A patent/CA2680467C/en not_active Expired - Fee Related
- 2008-03-12 ES ES08733559.2T patent/ES2565243T3/es active Active
- 2008-03-12 KR KR1020157016812A patent/KR20150080025A/ko not_active Ceased
- 2008-03-12 EP EP08733559.2A patent/EP2134680B1/en active Active
- 2008-03-12 KR KR1020097021343A patent/KR101678611B1/ko active Active
- 2008-03-12 JP JP2009552982A patent/JP2010520893A/ja active Pending
- 2008-03-12 TW TW097108730A patent/TWI549676B/zh active
-
2011
- 2011-05-11 US US13/105,151 patent/US8354445B2/en not_active Expired - Fee Related
-
2014
- 2014-02-12 JP JP2014024898A patent/JP5885311B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2565243T3 (es) | 2016-04-01 |
| HK1142597A1 (en) | 2010-12-10 |
| KR101678611B1 (ko) | 2016-11-22 |
| CN101679239A (zh) | 2010-03-24 |
| KR20090119004A (ko) | 2009-11-18 |
| US20110212965A1 (en) | 2011-09-01 |
| CA2680467A1 (en) | 2008-09-18 |
| WO2008109994A1 (en) | 2008-09-18 |
| KR20150080025A (ko) | 2015-07-08 |
| US20080227826A1 (en) | 2008-09-18 |
| JP2014159417A (ja) | 2014-09-04 |
| TW200848015A (en) | 2008-12-16 |
| EP2134680A1 (en) | 2009-12-23 |
| US8354445B2 (en) | 2013-01-15 |
| JP2010520893A (ja) | 2010-06-17 |
| JP5885311B2 (ja) | 2016-03-15 |
| US8030344B2 (en) | 2011-10-04 |
| EP2134680B1 (en) | 2016-01-13 |
| CN101679239B (zh) | 2014-12-10 |
| TWI549676B (zh) | 2016-09-21 |
| EP2134680A4 (en) | 2012-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130215 |
|
| MKLA | Lapsed |
Effective date: 20210312 |