JP2006500379A5 - - Google Patents
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- Publication number
- JP2006500379A5 JP2006500379A5 JP2004531045A JP2004531045A JP2006500379A5 JP 2006500379 A5 JP2006500379 A5 JP 2006500379A5 JP 2004531045 A JP2004531045 A JP 2004531045A JP 2004531045 A JP2004531045 A JP 2004531045A JP 2006500379 A5 JP2006500379 A5 JP 2006500379A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- hydrogen
- composition
- cancer
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 129
- -1 aryl carboxymethyl diisocyanatohexane Chemical compound 0.000 claims 99
- 239000001257 hydrogen Substances 0.000 claims 77
- 229910052739 hydrogen Inorganic materials 0.000 claims 77
- 239000000203 mixture Substances 0.000 claims 64
- 150000001875 compounds Chemical class 0.000 claims 57
- 150000002431 hydrogen Chemical class 0.000 claims 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 33
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 30
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 206010028980 Neoplasm Diseases 0.000 claims 29
- 201000011510 cancer Diseases 0.000 claims 29
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 25
- 125000004122 cyclic group Chemical group 0.000 claims 24
- 125000004414 alkyl thio group Chemical group 0.000 claims 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 14
- 125000003277 amino group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 125000004423 acyloxy group Chemical group 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 11
- 125000004104 aryloxy group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 11
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 239000006186 oral dosage form Substances 0.000 claims 9
- 125000002252 acyl group Chemical group 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 8
- 125000005277 alkyl imino group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims 8
- 125000004467 aryl imino group Chemical group 0.000 claims 8
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims 8
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 8
- 125000004997 halocarbonyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 8
- RIFHJAODNHLCBH-UHFFFAOYSA-N methanethione Chemical group S=[CH] RIFHJAODNHLCBH-UHFFFAOYSA-N 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 8
- 125000002723 alicyclic group Chemical group 0.000 claims 7
- 239000003937 drug carrier Substances 0.000 claims 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 7
- 208000036142 Viral infection Diseases 0.000 claims 5
- 125000005910 alkyl carbonate group Chemical group 0.000 claims 5
- 239000000262 estrogen Substances 0.000 claims 5
- 230000009385 viral infection Effects 0.000 claims 5
- 206010006187 Breast cancer Diseases 0.000 claims 4
- 208000026310 Breast neoplasm Diseases 0.000 claims 4
- 206010033128 Ovarian cancer Diseases 0.000 claims 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 4
- 241000700605 Viruses Species 0.000 claims 4
- 230000001419 dependent effect Effects 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 229940011871 estrogen Drugs 0.000 claims 4
- 230000001394 metastastic effect Effects 0.000 claims 4
- 206010061289 metastatic neoplasm Diseases 0.000 claims 4
- 230000036457 multidrug resistance Effects 0.000 claims 4
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000000732 arylene group Chemical group 0.000 claims 3
- 239000002775 capsule Substances 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 238000007911 parenteral administration Methods 0.000 claims 3
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 3
- 239000000376 reactant Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- VFTRKSBEFQDZKX-UHFFFAOYSA-N 3,3'-diindolylmethane Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4NC=3)=CNC2=C1 VFTRKSBEFQDZKX-UHFFFAOYSA-N 0.000 claims 2
- ZKVDBXMUQNGUBG-UHFFFAOYSA-N 5,7-dihydroindolo[2,3-b]carbazol-6-ol Chemical group N1C2=CC=CC=C2C2=C1C(O)=C(NC=1C3=CC=CC=1)C3=C2 ZKVDBXMUQNGUBG-UHFFFAOYSA-N 0.000 claims 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 241000701806 Human papillomavirus Species 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010038997 Retroviral infections Diseases 0.000 claims 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 201000010881 cervical cancer Diseases 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 125000001979 organolithium group Chemical group 0.000 claims 2
- 201000004228 ovarian endometrial cancer Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 206010046766 uterine cancer Diseases 0.000 claims 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 229940093768 3,3'-diindolylmethane Drugs 0.000 claims 1
- 235000010045 3,3'-diindolylmethane Nutrition 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical group [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 0 *c1c(c2c(*)c(*)c(*)c(*)c2[n]2*)c2c(*)c2c1c(c(*)c(*)c(*)c1*)c1[n]2* Chemical compound *c1c(c2c(*)c(*)c(*)c(*)c2[n]2*)c2c(*)c2c1c(c(*)c(*)c(*)c1*)c1[n]2* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/224,979 | 2002-08-20 | ||
| US10/224,979 US6800655B2 (en) | 2002-08-20 | 2002-08-20 | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
| PCT/US2003/025772 WO2004018475A2 (en) | 2002-08-20 | 2003-08-15 | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005305080A Division JP4699171B2 (ja) | 2002-08-20 | 2005-10-19 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
| JP2010139927A Division JP5599236B2 (ja) | 2002-08-20 | 2010-06-18 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006500379A JP2006500379A (ja) | 2006-01-05 |
| JP2006500379A5 true JP2006500379A5 (https=) | 2006-07-13 |
| JP4764629B2 JP4764629B2 (ja) | 2011-09-07 |
Family
ID=31946289
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004531045A Expired - Fee Related JP4764629B2 (ja) | 2002-08-20 | 2003-08-15 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
| JP2005305080A Expired - Fee Related JP4699171B2 (ja) | 2002-08-20 | 2005-10-19 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
| JP2010139927A Expired - Fee Related JP5599236B2 (ja) | 2002-08-20 | 2010-06-18 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005305080A Expired - Fee Related JP4699171B2 (ja) | 2002-08-20 | 2005-10-19 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
| JP2010139927A Expired - Fee Related JP5599236B2 (ja) | 2002-08-20 | 2010-06-18 | 化学療法薬および化学防御薬としてのインドール−３−カルビノール代謝物の類似物 |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US6800655B2 (https=) |
| EP (2) | EP1530572B1 (https=) |
| JP (3) | JP4764629B2 (https=) |
| AT (1) | ATE411317T1 (https=) |
| AU (1) | AU2003263878A1 (https=) |
| CA (1) | CA2496203C (https=) |
| DE (1) | DE60324155D1 (https=) |
| WO (1) | WO2004018475A2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6800655B2 (en) * | 2002-08-20 | 2004-10-05 | Sri International | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
| BRPI0510717B8 (pt) * | 2004-05-06 | 2021-05-25 | Bioresponse Llc | uso de 3,3' diindolilmetano (dim) ou 2-(indol-3-ilmetil)-3,3´-diindolilmetano (ltr) |
| US20060100264A1 (en) * | 2004-11-06 | 2006-05-11 | Bjeldanes Leonard F | 3,3'-Diindolylmethane immune activating compositions |
| ATE497762T1 (de) * | 2004-12-30 | 2011-02-15 | Bioresponse Llc | Verwendung von diindolylmethan-verwandten indolen zur behandlung und prävention von erkrankungen im zusammenhang mit dem respiratory syncytial virus |
| CN101146532B (zh) | 2005-01-21 | 2012-05-09 | 阿斯泰克斯治疗有限公司 | 药物化合物 |
| CA2609980C (en) * | 2005-05-27 | 2015-10-13 | Queen's University At Kingston | Treatment of protein folding disorders |
| CN1807413B (zh) * | 2005-09-28 | 2010-05-05 | 中国医学科学院医药生物技术研究所 | 咔唑磺酰胺衍生物及其制备方法 |
| CN101466687B (zh) | 2006-04-18 | 2012-04-11 | 日本化学医药株式会社 | 过氧化物酶体增殖剂激活受体δ的激活剂 |
| EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8586621B2 (en) * | 2006-10-27 | 2013-11-19 | Michael A. Zeligs | Anti-parasitic methods and compositions utilizing diindolylmethane-related indoles |
| WO2008144263A1 (en) * | 2007-05-18 | 2008-11-27 | The Ohio State University Research Foundation | Potent indole-3-carbinol-derived antitumor agents |
| US20100292316A1 (en) * | 2007-07-18 | 2010-11-18 | Research Development Foundation | Improved therapeutic methods and compositions comprising chroman ring compounds |
| EP2277874B1 (en) * | 2008-04-15 | 2018-06-27 | Nippon Chemiphar Co., Ltd. | Activator for peroxisome proliferator-activated receptor |
| WO2010033198A2 (en) * | 2008-09-17 | 2010-03-25 | Sri International | Analogs of indole-3-carbinol and their use as agents against infection |
| KR101477613B1 (ko) * | 2009-03-31 | 2014-12-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
| WO2010118339A2 (en) * | 2009-04-09 | 2010-10-14 | University Of Kansas | Formulations of indole-3-carbinol derived antitumor agents with increased oral bioavailability |
| CN102724978A (zh) * | 2009-08-14 | 2012-10-10 | 塞伦尼斯治疗公司 | 用于治疗或预防炎症或能量代谢/产生相关疾病的PPARδ配体的用途 |
| US8153680B2 (en) * | 2009-08-25 | 2012-04-10 | The Ohio State University Research Foundation | Alkyl indole-3-carbinol-derived antitumor agents |
| DE102009052428A1 (de) * | 2009-11-10 | 2011-05-12 | Merck Patent Gmbh | Verbindung für elektronische Vorrichtungen |
| AU2011248175A1 (en) * | 2010-05-06 | 2012-10-25 | Merck Sharp & Dohme Corp. | Aza-Indole derivatives useful as modulators of FAAH |
| CA2827214C (en) | 2011-04-01 | 2017-07-18 | Sri International | Lipoxygenase inhibitors |
| WO2015042170A1 (en) | 2013-09-17 | 2015-03-26 | Wayne State University | Compositions and uses of combinations of dim-related indoles and selected anti-androgen compounds |
| CN104030964B (zh) * | 2014-06-05 | 2016-06-29 | 天津科技大学 | 双吲哚类化合物及合成方法 |
| US9969686B2 (en) * | 2014-08-05 | 2018-05-15 | Wisconsin Alumni Research Foundation | Synthesis of diindolylmethanes and indolo[3,2-b]carbazoles, compounds formed thereby, and pharmaceutical compositions containing them |
| EP3280398B1 (en) | 2015-04-10 | 2026-02-25 | Bioresponse LLC | Self-emulsifying formulations of dim-related indoles |
| CA3030582A1 (en) | 2015-07-22 | 2017-01-26 | The Royal Institution For The Advancement Of Learning/Mcgill University | Compounds and uses thereof in the treatment of cancers and other medical conditions |
| CN105218552B (zh) * | 2015-09-30 | 2018-02-27 | 中国人民解放军军事医学科学院野战输血研究所 | 一种取代苯基二氢吲哚咔唑衍生物及其制备方法与应用 |
| CN110698654B (zh) * | 2018-07-10 | 2021-04-02 | 中国科学院长春应用化学研究所 | 基于三聚吲哚的超支化共轭聚电解质及其制备方法和用途 |
| WO2026010962A1 (en) | 2024-07-01 | 2026-01-08 | Otsuka America Pharmaceutical, Inc. | 3-pyrrolidine-indole derivative compounds useful for the treatment of disorders and methods related thereto |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1282451B (de) | 1965-09-01 | 1968-11-07 | Kalle Ag | Lichtempfindliche Schicht und Verfahren zur Herstellung fixierter Bilder |
| US4636820A (en) | 1980-03-06 | 1987-01-13 | The Hilton-Davis Chemical | Compositions, process and systems |
| ES2167303T3 (es) * | 1986-10-28 | 2002-05-16 | Ciba Sc Holding Ag | Ftalidas cromogenas. |
| GB8713564D0 (en) | 1987-06-10 | 1987-07-15 | Kong Y C | Synthesis |
| NZ227850A (en) * | 1988-02-10 | 1991-11-26 | Hoffmann La Roche | Indole substituted pyrrole derivatives; preparatory process and medicaments for use against inflammatory immunological, bronchopulmonary or vascular disorders |
| US5086171A (en) | 1989-03-08 | 1992-02-04 | Appleton Papers Inc. | Bis-(indolyl)ethylenes |
| US5116978A (en) | 1989-03-08 | 1992-05-26 | Appleton Papers Inc. | Process for bis(indolyl)ethylene synthesis |
| JP3038064B2 (ja) | 1991-10-07 | 2000-05-08 | 日清製粉株式会社 | インドール誘導体およびこれを有効成分とする抗潰瘍薬 |
| DE59207620D1 (de) | 1991-10-30 | 1997-01-16 | Ciba Geigy Ag | NIR-Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5206377A (en) * | 1991-12-05 | 1993-04-27 | Whitby Research, Inc. | Compounds useful as antiproliferative agents |
| US5407102A (en) * | 1994-02-15 | 1995-04-18 | Freudinger; Mark J. | Apparatus for dispensing a quantity of flowable material |
| US5948808A (en) * | 1997-03-07 | 1999-09-07 | The Texas A&M University System | Indole-3-carbinol, diindolylmethane and substituted analogs as antiestrogens |
| US5843607A (en) * | 1997-10-02 | 1998-12-01 | Xerox Corporation | Indolocarbazole photoconductors |
| US5942340A (en) | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
| HUP0102563A3 (en) | 1998-05-04 | 2003-04-28 | Zentaris Gmbh | Indole derivatives and their use in the treatment of malignant and other diseases caused by pathological cell proliferation |
| ATE277010T1 (de) | 1998-07-08 | 2004-10-15 | Harbor Branch Oceanographic | Bis-indolederivate und ihre verwendung als entzündungshemmende mittel |
| IT1317926B1 (it) | 2000-11-03 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati triciclici dell'indolo ad attivita' antiangiogenica. |
| IT1317925B1 (it) | 2000-11-03 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Bis-eterocicli ad attivita' antitumorale e chemosensibilizzante. |
| JP2003346530A (ja) | 2002-05-23 | 2003-12-05 | Nippon Sheet Glass Co Ltd | 面状光源装置および画像読み取り装置 |
| US6800655B2 (en) * | 2002-08-20 | 2004-10-05 | Sri International | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
-
2002
- 2002-08-20 US US10/224,979 patent/US6800655B2/en not_active Expired - Lifetime
-
2003
- 2003-08-15 CA CA2496203A patent/CA2496203C/en not_active Expired - Fee Related
- 2003-08-15 WO PCT/US2003/025772 patent/WO2004018475A2/en not_active Ceased
- 2003-08-15 EP EP03793096A patent/EP1530572B1/en not_active Expired - Lifetime
- 2003-08-15 AU AU2003263878A patent/AU2003263878A1/en not_active Abandoned
- 2003-08-15 JP JP2004531045A patent/JP4764629B2/ja not_active Expired - Fee Related
- 2003-08-15 DE DE60324155T patent/DE60324155D1/de not_active Expired - Lifetime
- 2003-08-15 AT AT03793096T patent/ATE411317T1/de not_active IP Right Cessation
- 2003-08-15 EP EP05077401.7A patent/EP1623985B1/en not_active Expired - Lifetime
-
2004
- 2004-02-03 US US10/772,036 patent/US7078427B2/en not_active Expired - Lifetime
-
2005
- 2005-10-19 JP JP2005305080A patent/JP4699171B2/ja not_active Expired - Fee Related
-
2006
- 2006-02-07 US US11/350,232 patent/US7429610B2/en not_active Expired - Lifetime
-
2008
- 2008-09-05 US US12/205,532 patent/US7666897B2/en not_active Expired - Fee Related
-
2010
- 2010-06-18 JP JP2010139927A patent/JP5599236B2/ja not_active Expired - Fee Related
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