JP2005534626A5 - - Google Patents
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- Publication number
- JP2005534626A5 JP2005534626A5 JP2003585680A JP2003585680A JP2005534626A5 JP 2005534626 A5 JP2005534626 A5 JP 2005534626A5 JP 2003585680 A JP2003585680 A JP 2003585680A JP 2003585680 A JP2003585680 A JP 2003585680A JP 2005534626 A5 JP2005534626 A5 JP 2005534626A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- alkoxy
- nitro
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 82
- 150000003839 salts Chemical class 0.000 claims 49
- 125000003545 alkoxy group Chemical group 0.000 claims 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 26
- -1 nitro, amino Chemical group 0.000 claims 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 22
- 239000000411 inducer Substances 0.000 claims 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 206010028980 Neoplasm Diseases 0.000 claims 12
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 12
- 201000011510 cancer Diseases 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 11
- 229940124597 therapeutic agent Drugs 0.000 claims 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims 8
- 229940123407 Androgen receptor antagonist Drugs 0.000 claims 6
- 239000003936 androgen receptor antagonist Substances 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 230000001939 inductive effect Effects 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 206010069921 Anti-androgen withdrawal syndrome Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 206010020112 Hirsutism Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 102000001307 androgen receptors Human genes 0.000 claims 1
- 108010080146 androgen receptors Proteins 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000008365 aqueous carrier Substances 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 230000021595 spermatogenesis Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 0 Cc(cc(C=CC(C(CC*)=C(C=C[C@](C1)C=CC(O)=C1OC)O)=O)cc1)c1O Chemical compound Cc(cc(C=CC(C(CC*)=C(C=C[C@](C1)C=CC(O)=C1OC)O)=O)cc1)c1O 0.000 description 2
- HVMUMOLHOCZBHW-UHFFFAOYSA-N BC(C(c(cc1)ccc1[N+]([O-])=O)=O)C(c(cc1)ccc1OC)=O Chemical compound BC(C(c(cc1)ccc1[N+]([O-])=O)=O)C(c(cc1)ccc1OC)=O HVMUMOLHOCZBHW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/124,642 | 2002-04-17 | ||
| US10/124,642 US6790979B2 (en) | 2002-04-17 | 2002-04-17 | Curcumin analogues and uses thereof |
| PCT/US2003/009350 WO2003088927A2 (en) | 2002-04-17 | 2003-03-27 | Novel curcumin analogues and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010012930A Division JP2010150266A (ja) | 2002-04-17 | 2010-01-25 | 新規なクルクミン類似体およびそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005534626A JP2005534626A (ja) | 2005-11-17 |
| JP2005534626A5 true JP2005534626A5 (enExample) | 2009-03-19 |
| JP5108198B2 JP5108198B2 (ja) | 2012-12-26 |
Family
ID=29248380
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003585680A Expired - Fee Related JP5108198B2 (ja) | 2002-04-17 | 2003-03-27 | 新規なクルクミン類似体およびそれらの使用 |
| JP2010012930A Pending JP2010150266A (ja) | 2002-04-17 | 2010-01-25 | 新規なクルクミン類似体およびそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010012930A Pending JP2010150266A (ja) | 2002-04-17 | 2010-01-25 | 新規なクルクミン類似体およびそれらの使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6790979B2 (enExample) |
| EP (1) | EP1494993B1 (enExample) |
| JP (2) | JP5108198B2 (enExample) |
| KR (2) | KR100984512B1 (enExample) |
| CN (1) | CN1646473B (enExample) |
| AT (1) | ATE466832T1 (enExample) |
| AU (1) | AU2003222087B8 (enExample) |
| CA (1) | CA2482002C (enExample) |
| DE (1) | DE60332445D1 (enExample) |
| DK (1) | DK1494993T3 (enExample) |
| ES (1) | ES2345930T3 (enExample) |
| MX (1) | MXPA04010180A (enExample) |
| NZ (1) | NZ535773A (enExample) |
| WO (1) | WO2003088927A2 (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7355081B2 (en) * | 2002-04-17 | 2008-04-08 | The University Of North Carolina At Chapel Hill | Curcumin analogues and uses thereof |
| US6790979B2 (en) * | 2002-04-17 | 2004-09-14 | University Of North Carolina At Chapel Hill | Curcumin analogues and uses thereof |
| AU2002314566A1 (en) * | 2002-06-17 | 2003-12-31 | Ho-Jeong Kwon | Novel curcumin derivatives |
| WO2004037269A1 (en) * | 2002-10-23 | 2004-05-06 | Pantarhei Bioscience B.V. | Pharmaceutical compositions comprising estetrol derivatives for use in cancer therapy |
| DK1624878T3 (da) * | 2003-05-22 | 2007-01-08 | Pantarhei Bioscience Bv | Anvendelse af præparater som omfatter en östrogen komponent til behandling og forebyggelse af muskel-skelet-smerte |
| US20050049299A1 (en) * | 2003-08-26 | 2005-03-03 | Aggarwal Bharat B. | Selective inhibitors of stat-3 activation and uses thereof |
| EP1692317A4 (en) * | 2003-12-12 | 2007-12-19 | Univ Rochester | Non-androgen dependent roles for androgen receptor and non-androgen related inhibitors of androgen receptor |
| JP2007526913A (ja) * | 2004-01-28 | 2007-09-20 | アンドロサイエンス コーポレイション | ステロイド依存性の遺伝子活性化経路の異なる段階を標的とする阻害剤の組み合わせによる抗アンドロゲン活性の増強およびその使用 |
| US20060084704A1 (en) * | 2004-01-28 | 2006-04-20 | Charles Shih | Methods and compositions for enhancing degradation of nuclear receptor transcription factors and uses thereof |
| EP2305352A1 (en) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | 5-alpha-reductase inhibitors for use in the treatment of men with metabolic and anthropometric disorders |
| CA2578159A1 (en) * | 2004-09-02 | 2006-03-16 | Androscience Corporation | Methods and compositions for enhancing degradation of nuclear receptor transcription factors and uses thereof |
| JP5063351B2 (ja) * | 2004-09-17 | 2012-10-31 | エグゼリクシス， インコーポレイテッド | ピラゾールキナーゼモジュレーターおよび使用方法 |
| FR2880276A1 (fr) * | 2005-01-05 | 2006-07-07 | Lefebvre Dominique Caparros | Utilisation des anti-androgenes dans le traitement des comportements agressifs ou impulsifs induits par des maladies du systeme nerveux central |
| CA2654467A1 (en) * | 2006-05-19 | 2007-11-29 | University Of Rochester | Prostate epithelial androgen receptor suppresses prostate growth and tumor invasion |
| US7507864B2 (en) * | 2006-08-01 | 2009-03-24 | Salisbury University | Method for the synthesis of curcumin analogues |
| EP2813145A1 (en) * | 2006-10-12 | 2014-12-17 | Research Foundation Of The City University Of New York | Novel curcumin and tetrahydrocurcumin derivatives |
| JP2010515685A (ja) * | 2007-01-08 | 2010-05-13 | アンドロサイエンス コーポレーション | （置換フェニル）−プロペナール部分を伴う化合物、その誘導体、生物学的活性およびその使用 |
| US9000222B2 (en) | 2007-01-08 | 2015-04-07 | Androscience Corporation | Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| US8710272B2 (en) | 2007-01-08 | 2014-04-29 | Androscience Corporation | Compounds with (1 E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| CN102432447B (zh) * | 2007-01-22 | 2014-01-08 | 温州医学院生物与天然药物开发中心有限公司 | 含环戊酮的姜黄素单羰基结构类似物及其用途 |
| CN102381951B (zh) * | 2007-01-22 | 2013-09-04 | 温州医学院生物与天然药物开发中心有限公司 | 含环己酮的姜黄素单羰基结构类似物及其用途 |
| CN101003470B (zh) * | 2007-01-22 | 2011-11-02 | 温州医学院生物与天然药物开发中心有限公司 | 姜黄素单羰基结构类似物及其用途 |
| ES2562205T3 (es) * | 2007-04-17 | 2016-03-03 | Codman & Shurtleff, Inc. | Hibrídos de curcumina resveratrol |
| US8383865B2 (en) * | 2007-04-17 | 2013-02-26 | Codman & Shurtleff, Inc. | Curcumin derivatives |
| CN101820765A (zh) * | 2007-07-31 | 2010-09-01 | 安德鲁科技有限公司 | 包含雄激素受体降解(ard)增强剂的组合物和预防性或治疗性治疗皮肤病与脱发的方法 |
| CN101255119B (zh) * | 2008-01-07 | 2014-05-21 | 沈阳药科大学 | 四氢姜黄素衍生物及盐类 |
| US20090282496A1 (en) * | 2008-04-04 | 2009-11-12 | University Of Rochester Medical Center | Androgen Receptor Related Methods for Treating Bladder Cancer |
| JP5481739B2 (ja) * | 2008-05-30 | 2014-04-23 | 国立大学法人東京工業大学 | アルツハイマー病治療薬 |
| CN101434525B (zh) * | 2008-06-05 | 2012-07-04 | 福建医科大学 | 4-(4-羟基-3-甲氧基苯甲基)姜黄素及其用于制备抗肿瘤药物的应用 |
| US7985776B2 (en) * | 2008-06-27 | 2011-07-26 | Codman & Shurtleff, Inc. | Iontophoretic delivery of curcumin and curcumin analogs for the treatment of Alzheimer's Disease |
| WO2010033580A2 (en) | 2008-09-19 | 2010-03-25 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Curcumin conjugates for treating and preventing cancers |
| US20100286585A1 (en) * | 2009-01-26 | 2010-11-11 | Codman & Shurtleff, Inc. | Shunt Delivery of Curcumin |
| US7723515B1 (en) * | 2009-01-26 | 2010-05-25 | Codman & Shurtleff, Inc. | Methylene blue—curcumin analog for the treatment of alzheimer's disease |
| CN101805285B (zh) * | 2009-02-13 | 2012-02-22 | 南华大学 | 含烟酸姜黄素酯衍生物及其制造方法和用途 |
| US9187406B2 (en) | 2009-05-15 | 2015-11-17 | The Research Foundation Of State University Of New York | Curcumin analogues as zinc chelators and their uses |
| CN101570515B (zh) * | 2009-06-12 | 2011-10-19 | 乐山师范学院 | 姜黄素取代嘧啶类衍生物及其制备方法与用途 |
| CN102091060A (zh) * | 2009-12-10 | 2011-06-15 | 温州医学院 | 治疗或预防糖皮质激素介导的性腺功能减退性功能障碍和/或不育的药物及其应用 |
| WO2011116066A1 (en) | 2010-03-17 | 2011-09-22 | Concert Pharmaceuticals, Inc. | Derivatives of dimethylcurcumin |
| CN102126938B (zh) * | 2010-12-15 | 2013-03-27 | 厦门大学 | 一种姜黄素类似物及其制备方法和应用 |
| EP3323816B1 (en) | 2011-04-11 | 2019-07-03 | Green Tech Co., Ltd. | Novel pyrazole derivative |
| WO2013076275A1 (en) * | 2011-11-23 | 2013-05-30 | The Provost, Fellows, Foundation Scholars, & The Other Members Of Board, Of The College Of The Holy & Undiv.Trinity Of Queen Elizabeth Near Dublin | Androgen receptor ligands |
| CN102649750B (zh) * | 2012-04-11 | 2014-01-22 | 福建医科大学 | 姜黄素水杨酰单酯及其合成方法以及其在抗肿瘤、抗炎方面的应用 |
| SG11201408387YA (en) * | 2012-06-18 | 2015-01-29 | Androscience Corp | Compounds with (1e, 6e)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disstituted-hepa-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| EP2866795A4 (en) | 2012-06-29 | 2016-01-27 | Univ New York State Res Found | POLYENOLZIN BINDER FOR THE ACTIVE PROMOTION OF THE INACTIVATION OF CANCER STRAIN CELLS AND FOR THE POTENTIATING OF CYTOTOXIC ANTITUMOROUS SUBSTANCES |
| US20160008297A1 (en) * | 2012-08-23 | 2016-01-14 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Compounds for preventing, reducing and/or alleviating itchy skin condition(s) |
| EP2907805B1 (en) * | 2012-10-10 | 2020-07-22 | Green Tech Co., Ltd. | Novel pyrazole derivative |
| CN103159644B (zh) * | 2013-04-08 | 2015-04-15 | 唐山师范学院 | 类姜黄素缩芳香胺希夫碱衍生物及其在制备抗菌药物的应用 |
| CN103222970B (zh) * | 2013-04-10 | 2019-03-26 | 温州医科大学 | 不对称单羰基姜黄素类似物在制备抗肿瘤药物中的应用 |
| CN103254051B (zh) * | 2013-05-28 | 2015-08-12 | 常州大学 | 一种二烷基姜黄素的制备方法 |
| JP6369751B2 (ja) * | 2014-09-05 | 2018-08-08 | 二村 芳弘 | ケラチン産生作用を呈するクルクミン誘導体及びその製造方法 |
| US9907786B2 (en) | 2014-10-21 | 2018-03-06 | Ions Pharmaceutical S.À R.L. | Therapeutic compositions containing harmine and isovanillin components, and methods of use thereof |
| US10092550B2 (en) | 2014-10-21 | 2018-10-09 | Ions Pharmaceutical S.À R.L. | Therapeutic compositions containing curcumin, harmine, and isovanillin components, and methods of use thereof |
| US20160106687A1 (en) | 2014-10-21 | 2016-04-21 | Life Plus, LLC | Human therapeutic agents |
| CN104557496B (zh) * | 2015-01-21 | 2018-03-16 | 温州医科大学 | 单羰基类化合物、组合物及在制备药物中的应用 |
| US11135318B2 (en) | 2016-06-29 | 2021-10-05 | The General Hospital Corporation | Half-curcuminoids as amyloid-beta PET imaging agents |
| US10300000B2 (en) | 2016-09-12 | 2019-05-28 | The Research Foundation For The State University Of New York | Inhibition of melanogenesis by chemically modified curcumins |
| CN106800547B (zh) * | 2017-01-03 | 2019-07-23 | 中国人民解放军第二军医大学 | 一种双取代芳基类化合物及其应用 |
| US20190358138A1 (en) * | 2017-02-15 | 2019-11-28 | Conopco, Inc., D/B/A Unilever | A personal care composition |
| WO2018204422A1 (en) | 2017-05-01 | 2018-11-08 | Spg Therapeutics, Inc. | Tripartite androgen receptor eliminators, methods and uses thereof |
| JP7332167B2 (ja) * | 2018-07-28 | 2023-08-23 | スージョウ・ファルマヴァン・カンパニー・リミテッド | 抗炎症性腸疾患の作用を有する医薬、その調製方法および使用 |
| JP2022553173A (ja) * | 2019-10-15 | 2022-12-22 | サミ－サビンサ グループ リミテッド | 代謝症候群の治療管理のためのクルクミノイド組成物 |
| US12129265B2 (en) | 2020-07-21 | 2024-10-29 | Ankh Life Sciences Limited | Therapeutic agents and uses thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07165724A (ja) * | 1993-12-13 | 1995-06-27 | Nkk Corp | ピラゾール誘導体及び血液凝固阻害剤 |
| IL112205A0 (en) * | 1994-01-06 | 1995-03-15 | Res Dev Foundation | Curcumin, analogues of curcumin and novel uses thereof |
| US5565491A (en) * | 1994-01-31 | 1996-10-15 | Bristol-Myers Squibb Company | Use of phosphotyrosine phospatase inhibitors for controlling cellular proliferation |
| US5679864A (en) * | 1995-11-03 | 1997-10-21 | Gene Print Inc. | Process for the synthesis of curcumin-related compounds |
| WO1999022728A1 (en) * | 1997-10-31 | 1999-05-14 | Arch Development Corporation | Methods and compositions for regulation of 5-alpha reductase activity |
| JP2000258904A (ja) * | 1999-03-04 | 2000-09-22 | Fujifilm Olin Co Ltd | ネガ型化学増幅系感光性組成物 |
| US6673843B2 (en) * | 1999-06-30 | 2004-01-06 | Emory University | Curcumin and curcuminoid inhibition of angiogenesis |
| WO2001030335A2 (en) | 1999-10-22 | 2001-05-03 | The Board Of Trustees Of The University Of Illinois | Pharmaceutical compositions useful in the prevention and treatment of beta-amyloid protein-induced disease |
| US6664272B2 (en) | 1999-12-03 | 2003-12-16 | Emory University | Curcumin analogs with anti-tumor and anti-angiogenic properties |
| US6790979B2 (en) * | 2002-04-17 | 2004-09-14 | University Of North Carolina At Chapel Hill | Curcumin analogues and uses thereof |
| DE60328517D1 (de) * | 2002-12-06 | 2009-09-03 | Dsm Ip Assets Bv | Neue verwendung von lycopin zur behandlung von erkrankungen im zusammenhang mit androgenwirkung |
| WO2004080396A2 (en) * | 2003-03-07 | 2004-09-23 | The University Of Texas Md Anderson Cancer Center | Liposomal curcumin for treatment of cancer |
-
2002
- 2002-04-17 US US10/124,642 patent/US6790979B2/en not_active Expired - Lifetime
-
2003
- 2003-03-27 WO PCT/US2003/009350 patent/WO2003088927A2/en not_active Ceased
- 2003-03-27 CN CN038086506A patent/CN1646473B/zh not_active Expired - Fee Related
- 2003-03-27 MX MXPA04010180A patent/MXPA04010180A/es active IP Right Grant
- 2003-03-27 DK DK03718072.6T patent/DK1494993T3/da active
- 2003-03-27 EP EP03718072A patent/EP1494993B1/en not_active Expired - Lifetime
- 2003-03-27 JP JP2003585680A patent/JP5108198B2/ja not_active Expired - Fee Related
- 2003-03-27 KR KR1020047016357A patent/KR100984512B1/ko not_active Expired - Fee Related
- 2003-03-27 NZ NZ535773A patent/NZ535773A/en not_active IP Right Cessation
- 2003-03-27 KR KR1020097018211A patent/KR101025226B1/ko not_active Expired - Fee Related
- 2003-03-27 AU AU2003222087A patent/AU2003222087B8/en not_active Revoked
- 2003-03-27 DE DE60332445T patent/DE60332445D1/de not_active Expired - Lifetime
- 2003-03-27 AT AT03718072T patent/ATE466832T1/de not_active IP Right Cessation
- 2003-03-27 ES ES03718072T patent/ES2345930T3/es not_active Expired - Lifetime
- 2003-03-27 CA CA2482002A patent/CA2482002C/en not_active Expired - Lifetime
-
2010
- 2010-01-25 JP JP2010012930A patent/JP2010150266A/ja active Pending
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