CN101003514A - 喹唑啉衍生物、其制备方法及用途 - Google Patents
喹唑啉衍生物、其制备方法及用途 Download PDFInfo
- Publication number
- CN101003514A CN101003514A CNA2006100235267A CN200610023526A CN101003514A CN 101003514 A CN101003514 A CN 101003514A CN A2006100235267 A CNA2006100235267 A CN A2006100235267A CN 200610023526 A CN200610023526 A CN 200610023526A CN 101003514 A CN101003514 A CN 101003514A
- Authority
- CN
- China
- Prior art keywords
- chloro
- quinazoline
- benzyloxy
- phenyl
- fluoro
- 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.)
- Pending
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000012453 solvate Substances 0.000 claims abstract 9
- 239000002246 antineoplastic agent Substances 0.000 claims abstract 2
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- -1 methoxy ethoxy Chemical group 0.000 claims description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004185 ester group Chemical group 0.000 claims description 15
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 11
- 125000001475 halogen functional group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 8
- 230000014509 gene expression Effects 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
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- 125000003118 aryl group Chemical group 0.000 claims description 2
- YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical class [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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- Pharmacology & Pharmacy (AREA)
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- General Chemical & Material Sciences (AREA)
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Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006100235267A CN101003514A (zh) | 2006-01-20 | 2006-01-20 | 喹唑啉衍生物、其制备方法及用途 |
| CN2006800012515A CN101103005B (zh) | 2006-01-20 | 2006-10-20 | 喹唑啉衍生物、其制备方法及用途 |
| PCT/CN2006/002786 WO2007082434A1 (en) | 2006-01-20 | 2006-10-20 | Quinazoline derivatives,preparation methods and uses thereof |
| US12/096,508 US8044063B2 (en) | 2006-01-20 | 2006-10-20 | Quinazoline derivatives useful as anti-tumor medicament |
| EP06804996.4A EP1990337B1 (en) | 2006-01-20 | 2006-10-20 | Quinazoline derivatives,preparation methods and uses thereof |
| EP10172688.3A EP2248806B1 (en) | 2006-01-20 | 2006-10-20 | Quinazoline derivatives as tyrosine kinase inhibitors |
| JP2008550608A JP5478894B2 (ja) | 2006-01-20 | 2006-10-20 | キナゾリン誘導体、その調製法および使用法 |
| US13/160,225 US8309563B2 (en) | 2006-01-20 | 2011-06-14 | Quinazoline derivatives useful as anti-tumor medicament |
| JP2012173258A JP2012214502A (ja) | 2006-01-20 | 2012-08-03 | キナゾリン誘導体、その調製法および使用法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006100235267A CN101003514A (zh) | 2006-01-20 | 2006-01-20 | 喹唑啉衍生物、其制备方法及用途 |
| PCT/CN2006/002786 WO2007082434A1 (en) | 2006-01-20 | 2006-10-20 | Quinazoline derivatives,preparation methods and uses thereof |
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| Publication Number | Publication Date |
|---|---|
| CN101003514A true CN101003514A (zh) | 2007-07-25 |
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| CNA2006100235267A Pending CN101003514A (zh) | 2006-01-20 | 2006-01-20 | 喹唑啉衍生物、其制备方法及用途 |
| CN2006800012515A Active CN101103005B (zh) | 2006-01-20 | 2006-10-20 | 喹唑啉衍生物、其制备方法及用途 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006800012515A Active CN101103005B (zh) | 2006-01-20 | 2006-10-20 | 喹唑啉衍生物、其制备方法及用途 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8044063B2 (enExample) |
| EP (2) | EP1990337B1 (enExample) |
| JP (2) | JP5478894B2 (enExample) |
| CN (2) | CN101003514A (enExample) |
| WO (1) | WO2007082434A1 (enExample) |
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| WO2009012702A1 (fr) * | 2007-07-20 | 2009-01-29 | Shanghai Allist Pharmaceutical., Inc. | Utilisation d'un dérivé de 4-aniline quinazoline pour la préparation de médicaments |
| CN101857617A (zh) * | 2010-04-28 | 2010-10-13 | 中国海洋大学 | 喹唑啉类糖衍生物及其制备方法和应用 |
| CN101899011A (zh) * | 2009-05-26 | 2010-12-01 | 北京大学 | 氨基二硫代甲酸酯类化合物、其制备方法和应用 |
| WO2011095053A1 (zh) * | 2010-02-08 | 2011-08-11 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物及其制备方法和应用 |
| CN102153544A (zh) * | 2010-02-12 | 2011-08-17 | 上海阳帆医药科技有限公司 | 一类新型酪氨酸激酶抑制剂的制备及用途 |
| CN101357905B (zh) * | 2007-08-01 | 2012-06-20 | 江苏艾力斯生物医药有限公司 | 4-[3-氯-4-(3-氟-苄氧基)-苯胺基]-6-取代胺基-喹唑啉衍生物的制备方法 |
| CN102659764A (zh) * | 2012-04-16 | 2012-09-12 | 中国科学院广州生物医药与健康研究院 | 酪氨酸激酶不可逆抑制剂及其制备方法和用途 |
| CN102702116A (zh) * | 2012-06-13 | 2012-10-03 | 华南理工大学 | 4-(3-氯-4-甲氧基苯胺基)-6-(3-胺基苯基)喹唑啉类化合物或其药学上可接受的盐和制备方法与应用 |
| US8507010B2 (en) | 2008-05-21 | 2013-08-13 | Shanghai Allist Pharmaceuticals, Inc. | Compositions comprising quinazoline derivatives |
| CN103382183A (zh) * | 2008-03-25 | 2013-11-06 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物多晶型物及其制法和应用 |
| CN105384745A (zh) * | 2015-07-27 | 2016-03-09 | 北京师范大学 | 冠醚环状的喹唑啉类化合物及其制备方法和在制备肿瘤治疗与显像药物中的应用 |
| US9725439B2 (en) | 2013-09-28 | 2017-08-08 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Quinazoline derivative and preparation method therefor |
| US10231973B2 (en) | 2015-03-20 | 2019-03-19 | Chai Tai Tianqing Pharmaceutical Group Co., Ltd. | Salts of quinazoline derivative and method for preparing the same |
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| CN101003514A (zh) * | 2006-01-20 | 2007-07-25 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物、其制备方法及用途 |
| CN101245050A (zh) * | 2007-02-14 | 2008-08-20 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物的盐 |
| UY31137A1 (es) * | 2007-06-14 | 2009-01-05 | Smithkline Beecham Corp | Derivados de quinazolina como inhibidores de la pi3 quinasa |
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| WO2010104406A1 (en) | 2009-03-11 | 2010-09-16 | Auckland Uniservices Limited | Prodrug forms of kinase inhibitors and their use in therapy |
| JP5925680B2 (ja) * | 2009-09-02 | 2016-05-25 | オークランド ユニサーヴィスィズ リミテッド | キナーゼインヒビター、そのプロドラッグ型および治療におけるそれらの使用 |
| CN101857618B (zh) * | 2010-06-13 | 2015-11-25 | 中国海洋大学 | 作为蛋白酪氨酸激酶抑制剂的一系列喹唑啉糖衍生物，其制备方法和应用 |
| CN102898386B (zh) | 2011-07-27 | 2015-07-29 | 上海医药集团股份有限公司 | 喹唑啉衍生物、其制备方法、中间体、组合物及其应用 |
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| WO2014177038A1 (en) | 2013-04-28 | 2014-11-06 | Sunshine Lake Pharma Co., Ltd. | Aminoquinazoline derivatives and their salts and methods of use thereof |
| CA2969974C (en) | 2014-12-15 | 2020-08-04 | The Regents Of The University Of Michigan | Small molecule inhibitors of egfr and pi3k |
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| WO2022033410A1 (zh) * | 2020-08-10 | 2022-02-17 | 上海和誉生物医药科技有限公司 | 一种egfr抑制剂及其制备方法和应用 |
| US11673876B2 (en) | 2020-12-22 | 2023-06-13 | Mekanistic Therapeutics Llc | Substituted aminobenzyl heteroaryl compounds as EGFR and/or PI3K inhibitors |
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| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| GB9510757D0 (en) * | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| TW321649B (enExample) | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
| EP1110953B1 (en) * | 1995-03-30 | 2009-10-28 | Pfizer Products Inc. | Quinazoline derivatives |
| GB9508538D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| RO121900B1 (ro) | 1996-04-12 | 2008-07-30 | Warner-Lambert Company | Compuşi inhibitori, ireversibili, ai tirozin kinazelor, compoziţie farmaceutică care îi conţine şi utilizarea acestora |
| ZA986732B (en) * | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| GB9800569D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
| GB9800575D0 (en) * | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
| TW533204B (en) | 1998-07-30 | 2003-05-21 | Wyeth Corp | A process for preparing substituted quinazoline derivatives |
| ATE377597T1 (de) * | 1999-07-09 | 2007-11-15 | Glaxo Group Ltd | Anilinochinazoline als protein-tyrosin- kinasehemmer |
| WO2001021596A1 (en) * | 1999-09-21 | 2001-03-29 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| HUP0204413A3 (en) | 1999-09-21 | 2003-07-28 | Astrazeneca Ab | Quinazoline compounds, their preparation, their use and pharmaceutical compositions containing them |
| GB9925958D0 (en) | 1999-11-02 | 1999-12-29 | Bundred Nigel J | Therapeutic use |
| US20070123537A1 (en) * | 2003-10-06 | 2007-05-31 | Gpc Biotech Ag | Quinazoline derivatives for the treatment of herpesviral infections |
| EP1682123A1 (en) * | 2003-11-07 | 2006-07-26 | SmithKline Beecham (Cork) Limited | Cancer treatment method |
| WO2005097134A2 (en) * | 2004-03-31 | 2005-10-20 | The Scripps Research Institute | Quinazoline based protein kinase inhibitors |
| KR100735639B1 (ko) | 2004-12-29 | 2007-07-04 | 한미약품 주식회사 | 암세포 성장 억제 효과를 갖는 퀴나졸린 유도체 및 이의제조방법 |
| CN101163684B (zh) * | 2005-02-23 | 2012-08-29 | 盐野义制药株式会社 | 具有酪氨酸激酶抑制作用的喹唑啉衍生物 |
| CN101003514A (zh) * | 2006-01-20 | 2007-07-25 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物、其制备方法及用途 |
-
2006
- 2006-01-20 CN CNA2006100235267A patent/CN101003514A/zh active Pending
- 2006-10-20 JP JP2008550608A patent/JP5478894B2/ja active Active
- 2006-10-20 EP EP06804996.4A patent/EP1990337B1/en active Active
- 2006-10-20 US US12/096,508 patent/US8044063B2/en active Active
- 2006-10-20 WO PCT/CN2006/002786 patent/WO2007082434A1/zh not_active Ceased
- 2006-10-20 EP EP10172688.3A patent/EP2248806B1/en active Active
- 2006-10-20 CN CN2006800012515A patent/CN101103005B/zh active Active
-
2011
- 2011-06-14 US US13/160,225 patent/US8309563B2/en active Active
-
2012
- 2012-08-03 JP JP2012173258A patent/JP2012214502A/ja not_active Withdrawn
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101347433B (zh) * | 2007-07-20 | 2012-05-02 | 江苏艾力斯生物医药有限公司 | 4-苯胺喹唑啉衍生物的制药用途 |
| WO2009012702A1 (fr) * | 2007-07-20 | 2009-01-29 | Shanghai Allist Pharmaceutical., Inc. | Utilisation d'un dérivé de 4-aniline quinazoline pour la préparation de médicaments |
| CN101357905B (zh) * | 2007-08-01 | 2012-06-20 | 江苏艾力斯生物医药有限公司 | 4-[3-氯-4-(3-氟-苄氧基)-苯胺基]-6-取代胺基-喹唑啉衍生物的制备方法 |
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| CN103420925B (zh) * | 2008-03-25 | 2014-11-12 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物多晶型物及其制法和应用 |
| CN103382183B (zh) * | 2008-03-25 | 2014-11-12 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物多晶型物及其制法和应用 |
| CN102007104B (zh) * | 2008-03-25 | 2014-02-19 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物多晶型物及其制法和应用 |
| CN103420925A (zh) * | 2008-03-25 | 2013-12-04 | 上海艾力斯医药科技有限公司 | 4-苯胺喹唑啉衍生物多晶型物及其制法和应用 |
| US8507010B2 (en) | 2008-05-21 | 2013-08-13 | Shanghai Allist Pharmaceuticals, Inc. | Compositions comprising quinazoline derivatives |
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| CN101899011B (zh) * | 2009-05-26 | 2013-01-16 | 北京大学 | 氨基二硫代甲酸酯类化合物、其制备方法和应用 |
| CN102812010A (zh) * | 2010-02-08 | 2012-12-05 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物及其制备方法和应用 |
| WO2011095053A1 (zh) * | 2010-02-08 | 2011-08-11 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物及其制备方法和应用 |
| CN102812010B (zh) * | 2010-02-08 | 2015-09-30 | 上海艾力斯医药科技有限公司 | 喹唑啉衍生物及其制备方法和应用 |
| CN102153544A (zh) * | 2010-02-12 | 2011-08-17 | 上海阳帆医药科技有限公司 | 一类新型酪氨酸激酶抑制剂的制备及用途 |
| CN102153544B (zh) * | 2010-02-12 | 2015-04-29 | 上海阳帆医药科技有限公司 | 一类酪氨酸激酶抑制剂的制备及用途 |
| CN101857617A (zh) * | 2010-04-28 | 2010-10-13 | 中国海洋大学 | 喹唑啉类糖衍生物及其制备方法和应用 |
| CN102659764A (zh) * | 2012-04-16 | 2012-09-12 | 中国科学院广州生物医药与健康研究院 | 酪氨酸激酶不可逆抑制剂及其制备方法和用途 |
| CN102702116A (zh) * | 2012-06-13 | 2012-10-03 | 华南理工大学 | 4-(3-氯-4-甲氧基苯胺基)-6-(3-胺基苯基)喹唑啉类化合物或其药学上可接受的盐和制备方法与应用 |
| CN102702116B (zh) * | 2012-06-13 | 2014-12-31 | 华南理工大学 | 4-(3-氯-4-甲氧基苯胺基)-6-(3-胺基苯基)喹唑啉类化合物或其药学上可接受的盐和制备方法与应用 |
| US9725439B2 (en) | 2013-09-28 | 2017-08-08 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Quinazoline derivative and preparation method therefor |
| CN105555782B (zh) * | 2013-09-28 | 2017-11-10 | 正大天晴药业集团股份有限公司 | 喹唑啉衍生物及其制备方法 |
| US10231973B2 (en) | 2015-03-20 | 2019-03-19 | Chai Tai Tianqing Pharmaceutical Group Co., Ltd. | Salts of quinazoline derivative and method for preparing the same |
| CN105384745A (zh) * | 2015-07-27 | 2016-03-09 | 北京师范大学 | 冠醚环状的喹唑啉类化合物及其制备方法和在制备肿瘤治疗与显像药物中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2248806A3 (en) | 2011-02-23 |
| EP2248806B1 (en) | 2013-04-24 |
| WO2007082434A1 (en) | 2007-07-26 |
| US20080300248A1 (en) | 2008-12-04 |
| JP2009525956A (ja) | 2009-07-16 |
| EP1990337A1 (en) | 2008-11-12 |
| JP2012214502A (ja) | 2012-11-08 |
| US8044063B2 (en) | 2011-10-25 |
| CN101103005A (zh) | 2008-01-09 |
| US8309563B2 (en) | 2012-11-13 |
| EP1990337B1 (en) | 2013-05-08 |
| US20110245246A1 (en) | 2011-10-06 |
| EP1990337A4 (en) | 2009-07-22 |
| EP2248806A2 (en) | 2010-11-10 |
| CN101103005B (zh) | 2011-05-04 |
| JP5478894B2 (ja) | 2014-04-23 |
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