JP2002521428A5 - - Google Patents
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- Publication number
- JP2002521428A5 JP2002521428A5 JP2000561989A JP2000561989A JP2002521428A5 JP 2002521428 A5 JP2002521428 A5 JP 2002521428A5 JP 2000561989 A JP2000561989 A JP 2000561989A JP 2000561989 A JP2000561989 A JP 2000561989A JP 2002521428 A5 JP2002521428 A5 JP 2002521428A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- carnitine
- anticancer agent
- pharmaceutically acceptable
- compound
- 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
- 239000008194 pharmaceutical composition Substances 0.000 description 34
- 239000002246 antineoplastic agent Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 14
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 12
- 229930012538 Paclitaxel Natural products 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229960001592 paclitaxel Drugs 0.000 description 10
- 108010006654 Bleomycin Proteins 0.000 description 9
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 description 9
- 229960001561 bleomycin Drugs 0.000 description 9
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical group N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 6
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 5
- 229960004562 carboplatin Drugs 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 5
- 229960004528 vincristine Drugs 0.000 description 5
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 5
- UFAHZIUFPNSHSL-MRVPVSSYSA-N O-propanoyl-L-carnitine Chemical compound CCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C UFAHZIUFPNSHSL-MRVPVSSYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- -1 alkanoyl L-carnitine Chemical compound 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 229960004203 carnitine Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 125000002456 taxol group Chemical group 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- NDVRKEKNSBMTAX-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;phosphoric acid Chemical compound OP(O)(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O NDVRKEKNSBMTAX-BTVCFUMJSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 208000004852 Lung Injury Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- QWYFHHGCZUCMBN-SECBINFHSA-N O-butanoyl-L-carnitine Chemical compound CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C QWYFHHGCZUCMBN-SECBINFHSA-N 0.000 description 1
- VSNFQQXVMPSASB-SNVBAGLBSA-N O-valeroyl-L-carnitine Chemical compound CCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C VSNFQQXVMPSASB-SNVBAGLBSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010069363 Traumatic lung injury Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- IGQBPDJNUXPEMT-SNVBAGLBSA-N isovaleryl-L-carnitine Chemical compound CC(C)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C IGQBPDJNUXPEMT-SNVBAGLBSA-N 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 208000004235 neutropenia Diseases 0.000 description 1
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98RM000511 IT1302121B1 (it) | 1998-07-30 | 1998-07-30 | Associazione ad attivita' antineoplastica sostanzialmente priva deglieffetti tossici o collaterali causati dai farmaci antineoplastici |
| ITRM98A000511 | 1998-07-30 | ||
| IT1999RM000206 IT1306124B1 (it) | 1999-04-07 | 1999-04-07 | Uso di alcanoil l-carnitine nella preparazione di medicamenti adattivita' antitumorale. |
| ITRM99A000206 | 1999-04-07 | ||
| IT99A000206 | 1999-04-07 | ||
| IT98A000511 | 1999-04-07 | ||
| PCT/IT1999/000242 WO2000006134A2 (en) | 1998-07-30 | 1999-07-27 | Use of l-carnitine and its alkanoyl derivatives in the preparation of medicaments with anticancer activity |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010181377A Division JP2010254717A (ja) | 1998-07-30 | 2010-08-13 | Ｌ−カルニチンおよびそのアルカノイル誘導体の、抗癌作用を有する医薬品の製造のための使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002521428A JP2002521428A (ja) | 2002-07-16 |
| JP2002521428A5 true JP2002521428A5 (enExample) | 2006-09-14 |
| JP4703851B2 JP4703851B2 (ja) | 2011-06-15 |
Family
ID=26332128
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000561989A Expired - Fee Related JP4703851B2 (ja) | 1998-07-30 | 1999-07-27 | Ｌ−カルニチンおよびそのアルカノイル誘導体の、抗癌作用を有する医薬品の製造のための使用 |
| JP2010181377A Pending JP2010254717A (ja) | 1998-07-30 | 2010-08-13 | Ｌ−カルニチンおよびそのアルカノイル誘導体の、抗癌作用を有する医薬品の製造のための使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010181377A Pending JP2010254717A (ja) | 1998-07-30 | 2010-08-13 | Ｌ−カルニチンおよびそのアルカノイル誘導体の、抗癌作用を有する医薬品の製造のための使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (5) | US6610699B2 (enExample) |
| EP (1) | EP1100589B1 (enExample) |
| JP (2) | JP4703851B2 (enExample) |
| KR (1) | KR100645980B1 (enExample) |
| AT (1) | ATE287278T1 (enExample) |
| AU (1) | AU764807B2 (enExample) |
| CA (1) | CA2338638C (enExample) |
| DE (1) | DE69923322T2 (enExample) |
| ES (1) | ES2235499T3 (enExample) |
| PT (1) | PT1100589E (enExample) |
| WO (1) | WO2000006134A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9803448D0 (en) | 1998-02-18 | 1998-04-15 | Pharma Mar Sa | Pharmaceutical formulation |
| US20030199535A1 (en) * | 1998-07-30 | 2003-10-23 | Claudio Cavazza | Method for preventing and/or treating peripheral neuropathies induced by the administration of an anticancer agent |
| IT1302289B1 (it) * | 1998-09-30 | 2000-09-05 | Univ Catania | Composizioni farmaceutiche ad attivita' antineoplastica |
| US20070037777A1 (en) * | 2005-08-12 | 2007-02-15 | Immunopath Profile, Inc. | Lipid-containing compositions and methods of using them |
| DE19959546A1 (de) * | 1999-12-09 | 2001-06-21 | Rhone Poulenc Rorer Gmbh | Pharmazeutische Zubereitung zur Behandlung von Tumorerkrankungen |
| UA76718C2 (uk) | 2000-06-30 | 2006-09-15 | Фарма Мар, С.А. | Протипухлинні похідні аплідину |
| BR0114604A (pt) * | 2000-10-12 | 2003-10-14 | Pharma Mar Sa | Tratamento de cnceres |
| AU2002336206B2 (en) * | 2001-10-19 | 2007-11-29 | Pharma Mar, S.A. | Use of aplidine for the treatment of pancreatic cancer |
| ITRM20020306A1 (it) | 2002-05-31 | 2003-12-01 | Sigma Tau Ind Farmaceuti | Esteri in posizione 20 di camptotecine. |
| WO2004080477A1 (en) | 2003-03-12 | 2004-09-23 | Dana-Farber Cancer Institute, Inc. | Aplidine for multiple myeloma treatment |
| US8314144B2 (en) * | 2004-02-12 | 2012-11-20 | Defiante Farmaceutica, S.A. | Compounds having antitumor activity |
| US20050215640A1 (en) | 2004-03-26 | 2005-09-29 | Baxter Jeffrey H | HMB compositions and uses thereof |
| US20050232911A1 (en) * | 2004-04-19 | 2005-10-20 | Schreiber Brian D | Prevention and treatment of metabolic abnormalities associated with excess intramyocellular lipid |
| US8778992B2 (en) | 2005-12-19 | 2014-07-15 | Abbott Laboratories | Method of using beta-hydroxy-beta-methylbutyrate to treat allergies and asthma |
| ITMI20070817A1 (it) | 2007-04-19 | 2008-10-20 | Farmacetika Ltd | Composizione farmaceutica comprendente l-carnitina ed un agente antagonista dei recettori adenosinici di membrana, loro derivati e/o sali farmaceuticamente accettabili, e uso degli stessi nella preparazione di farmaci con effetto non tossico di inibi |
| CN101790377A (zh) * | 2007-08-31 | 2010-07-28 | 国立大学法人九州大学 | 抗癌剂导致的末梢神经障碍的预防或减轻剂 |
| EA201170732A1 (ru) * | 2008-12-01 | 2011-12-30 | Сигма-Тау Индустрие Фармасьютике Риуните С.П.А. | Применение алканоил l-карнитина в комбинации с химиотерапевтическими средствами для лечения новообразований |
| CN102060722B (zh) * | 2009-05-01 | 2014-06-11 | 常州高新技术产业开发区三维工业技术研究所有限公司 | 一种含砷化合物及其制备方法和用途 |
| TWI580363B (zh) | 2010-01-29 | 2017-05-01 | 亞培公司 | 包含鈣ｈｍｂ的營養乳劑 |
| US9693577B2 (en) | 2010-01-29 | 2017-07-04 | Abbott Laboratories | Method of preparing a nutritional powder comprising spray dried HMB |
| WO2011094548A1 (en) | 2010-01-29 | 2011-08-04 | Abbott Laboratories | Aseptically packaged nutritional liquids comprising hmb |
| TWI526161B (zh) | 2010-06-10 | 2016-03-21 | 亞培公司 | 包含鈣ｈｍｂ及可溶性蛋白質之實質上透明營養液 |
| DE102011008016A1 (de) * | 2011-01-06 | 2012-07-12 | Johannes F. Coy | Schokoladenmasse |
| WO2014004902A2 (en) * | 2012-06-27 | 2014-01-03 | Amazentis Sa | Enhancing autophagy or increasing longevity by administration of urolithins or precursors thereof |
| ITPZ20130005A1 (it) * | 2013-07-05 | 2015-01-06 | Teodosio Antonio Ferrara | Metabolismo energetico e omeostasi |
| RU2554776C1 (ru) * | 2013-12-16 | 2015-06-27 | Федеральное государственное бюджетное учреждение "Дальневосточный научный центр физиологии и патологии дыхания" СО РАМН | Средство для коррекции нарушений в легочной ткани при цитостатическом воздействии |
| BR112017022666A8 (pt) | 2015-04-20 | 2022-10-18 | Tolero Pharmaceuticals Inc | Preparando resposta à alvocidib por perfilamento mitocondrial |
| EP4086264B1 (en) | 2015-05-18 | 2023-10-25 | Sumitomo Pharma Oncology, Inc. | Alvocidib prodrugs having increased bioavailability |
| CA2993659A1 (en) | 2015-08-03 | 2017-02-09 | Tolero Pharmaceuticals, Inc. | Combination therapies for treatment of cancer |
| KR101732483B1 (ko) * | 2016-07-06 | 2017-05-24 | 한국 한의학 연구원 | 연교 추출물을 유효성분으로 함유하는 말초신경병증 예방, 개선 또는 치료용 조성물 |
| US11279694B2 (en) | 2016-11-18 | 2022-03-22 | Sumitomo Dainippon Pharma Oncology, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
| JP7196160B2 (ja) | 2017-09-12 | 2022-12-26 | スミトモ ファーマ オンコロジー， インコーポレイテッド | Ｍｃｌ－１阻害剤アルボシジブを用いた、ｂｃｌ－２阻害剤に対して非感受性である癌の治療レジメン |
| CA3119807A1 (en) | 2018-12-04 | 2020-06-11 | Sumitomo Dainippon Pharma Oncology, Inc. | Cdk9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
| US11793802B2 (en) | 2019-03-20 | 2023-10-24 | Sumitomo Pharma Oncology, Inc. | Treatment of acute myeloid leukemia (AML) with venetoclax failure |
| CN115177608B (zh) * | 2022-07-26 | 2023-12-05 | 南方医科大学南方医院 | 长链酰基肉碱类化合物在制备预防和/或治疗肝癌的药物中的应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713370A (en) * | 1972-11-06 | 1987-12-15 | Felice Stephen L De | Carnitine and its use in reducing cardiac toxicity and as a synergist with cytostats |
| US4267163A (en) * | 1972-11-06 | 1981-05-12 | Biocarn Limited | Carnitine and its use in reducing cardiac toxicity |
| IT1169460B (it) * | 1982-09-13 | 1987-05-27 | Sigma Tau Ind Farmaceuti | Metodo e composizione per il trattamento di tumori |
| US4599352A (en) * | 1984-03-01 | 1986-07-08 | The United States Of America As Represented By The Department Of Health And Human Services | Antineoplastic platinum (IV) complexes and compositions |
| IT1196564B (it) * | 1986-08-04 | 1988-11-16 | Sigma Tau Ind Farmaceuti | Impiego di acetil l-carnitina nel trattamento terapeutico delle neuropatie periferiche |
| US4936823A (en) * | 1988-05-04 | 1990-06-26 | Triangle Research And Development Corp. | Transendoscopic implant capsule |
| IT1235153B (it) * | 1988-11-15 | 1992-06-22 | Sigma Tau Ind Farmaceuti | Uso dell'acetil l-carnitina nel trattamento terapeutico della cataratta e composizioni farmaceutiche utili in tale trattamento |
| US5639737A (en) * | 1991-11-04 | 1997-06-17 | Co Enzyme Technology Ltd. | Method and compositions for treating malignant tumors and inhibiting growth and metastases of malignant tumors |
| FR2697752B1 (fr) * | 1992-11-10 | 1995-04-14 | Rhone Poulenc Rorer Sa | Compositions antitumorales contenant des dérivés du taxane. |
| FR2727117A1 (fr) * | 1994-11-18 | 1996-05-24 | Geffard Michel | Utilisation de conjugues de la polylysine pour la preparation de medicaments utiles dans le traitement des maladies neurodegeneratives et des affections degeneratives a caractere autoimmun |
| IT1275434B (it) * | 1995-05-19 | 1997-08-07 | Farmila Farma Milano | Composizioni farmaceutiche e/o dietetiche ad attivita' antiossidante |
| IT1277898B1 (it) * | 1995-08-03 | 1997-11-12 | Mendes Srl | Uso di amminoacidi basici, di acil derivati di amminoacidi basici e di loro sali farmaceuticamente accettabili per la profilassi di malattie |
| IT1283951B1 (it) * | 1996-03-15 | 1998-05-07 | Mendes Srl | Uso della acetil l-carnitina o dei suoi sali farmacologicamente accettabili per il trattamento terapeutico o la profilassi di |
| DE19733305A1 (de) * | 1997-08-01 | 1999-02-04 | Asta Medica Ag | Pharmazeutische Zusammensetzung enthaltend Ifosfamid und Carnitin |
-
1999
- 1999-07-27 JP JP2000561989A patent/JP4703851B2/ja not_active Expired - Fee Related
- 1999-07-27 KR KR1020017001228A patent/KR100645980B1/ko not_active Expired - Fee Related
- 1999-07-27 WO PCT/IT1999/000242 patent/WO2000006134A2/en not_active Ceased
- 1999-07-27 EP EP99936973A patent/EP1100589B1/en not_active Expired - Lifetime
- 1999-07-27 AT AT99936973T patent/ATE287278T1/de active
- 1999-07-27 PT PT99936973T patent/PT1100589E/pt unknown
- 1999-07-27 ES ES99936973T patent/ES2235499T3/es not_active Expired - Lifetime
- 1999-07-27 AU AU51935/99A patent/AU764807B2/en not_active Ceased
- 1999-07-27 DE DE69923322T patent/DE69923322T2/de not_active Expired - Lifetime
- 1999-07-27 CA CA002338638A patent/CA2338638C/en not_active Expired - Fee Related
-
2001
- 2001-01-26 US US09/769,488 patent/US6610699B2/en not_active Expired - Fee Related
-
2006
- 2006-04-20 US US11/407,351 patent/US20060258744A1/en not_active Abandoned
-
2008
- 2008-04-09 US US12/078,991 patent/US20080194683A1/en not_active Abandoned
-
2009
- 2009-01-26 US US12/320,430 patent/US20090143464A1/en not_active Abandoned
- 2009-01-26 US US12/320,422 patent/US20090137619A1/en not_active Abandoned
-
2010
- 2010-08-13 JP JP2010181377A patent/JP2010254717A/ja active Pending
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