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 US6800655B2 (en) | 2002-08-20 | 2002-08-20 | Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents |
| US10/224,979 | 2002-08-20 | ||
| 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 |
| WO2005107747A2 (en) * | 2004-05-06 | 2005-11-17 | Bioresponse, Llc | Diindolymethane formulations for the treatment of leiomyomas |
| US20060100264A1 (en) * | 2004-11-06 | 2006-05-11 | Bjeldanes Leonard F | 3,3'-Diindolylmethane immune activating compositions |
| CA2593084C (en) | 2004-12-30 | 2014-03-18 | Bioresponse, Llc | Use of diindolylmethane-related indoles for the treatment and prevention of respiratory syncytial virus associated conditions |
| JP5475234B2 (ja) | 2005-01-21 | 2014-04-16 | アステックス・セラピューティクス・リミテッド | 医薬化合物 |
| EP1893576A4 (en) * | 2005-05-27 | 2010-03-17 | Univ Kingston | TREATMENT OF PROTEIN DISORDERING |
| 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 |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| BRPI0717753B1 (pt) | 2006-10-27 | 2022-04-12 | Bioresponse, Llc | Uso de uma composição compreendendo 50-250 mg de um ou mais indóis relacionados com dim e um ou mais agentes anti-protozoários, e, composição |
| 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 |
| MX2010011252A (es) | 2008-04-15 | 2010-11-30 | Nippon Chemiphar Co | Activador para el receptor activado por el proliferador de peroxisoma. |
| JP5550151B2 (ja) * | 2008-09-17 | 2014-07-16 | エスアールアイ インターナショナル | インドール−３−カルビノール類似体およびその感染に対する薬剤としての使用 |
| 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 |
| AU2010282399A1 (en) * | 2009-08-14 | 2012-03-01 | Cerenis Therapeutics Holding S.A. | Use of PPAR delta ligands for the treatment or prevention of inflammation or energy metabolism/production related diseases |
| 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 |
| CN103764143B (zh) * | 2011-04-01 | 2017-05-03 | 斯坦福国际咨询研究所 | 脂氧合酶抑制剂 |
| 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 |
| CA2982162C (en) | 2015-04-10 | 2023-10-10 | Bioresponse, L.L.C. | Self-emulsifying formulations of dim-related indoles |
| US10844051B2 (en) | 2015-07-22 | 2020-11-24 | The Royal Institution For The Advancement Of Learning/Mcgill University | Substituted oxazoles for the treatment of cancer |
| 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 |
| EP0266310B1 (de) * | 1986-10-28 | 2001-12-05 | Ciba SC Holding AG | Chromogene Phthalide |
| GB8713564D0 (en) | 1987-06-10 | 1987-07-15 | Kong Y C | Synthesis |
| CZ280738B6 (cs) * | 1988-02-10 | 1996-04-17 | F. Hoffmann - La Roche And Co., Aktiengesellschaft | Substituované pyrroly, jejich použití pro výrobu léčiv a léčiva na jejich bázi |
| 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 |
| EP0540468B1 (de) * | 1991-10-30 | 1996-12-04 | 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 |
| JP2002514572A (ja) | 1998-05-04 | 2002-05-21 | ツェンタリス アクチエンゲゼルシャフト | インドール誘導体および悪性疾患および病理的細胞増殖にもとづく他の疾患を治療するためのその使用 |
| WO2000002857A1 (en) * | 1998-07-08 | 2000-01-20 | Harbor Branch Oceanographic Institution, Inc. | Bis-indole derivatives and their use as antiinflammatory agents |
| IT1317925B1 (it) | 2000-11-03 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Bis-eterocicli ad attivita' antitumorale e chemosensibilizzante. |
| IT1317926B1 (it) | 2000-11-03 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Derivati triciclici dell'indolo ad attivita' antiangiogenica. |
| 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 AT AT03793096T patent/ATE411317T1/de not_active IP Right Cessation
- 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 EP EP05077401.7A patent/EP1623985B1/en not_active Expired - Lifetime
- 2003-08-15 AU AU2003263878A patent/AU2003263878A1/en not_active Abandoned
- 2003-08-15 DE DE60324155T patent/DE60324155D1/de not_active Expired - Lifetime
- 2003-08-15 CA CA2496203A patent/CA2496203C/en not_active Expired - Fee Related
- 2003-08-15 JP JP2004531045A patent/JP4764629B2/ja not_active Expired - Fee Related
-
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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