JP2008520662A - 抗微生物活性を有する新規リンコマイシン誘導体 - Google Patents
抗微生物活性を有する新規リンコマイシン誘導体 Download PDFInfo
- Publication number
- JP2008520662A JP2008520662A JP2007543023A JP2007543023A JP2008520662A JP 2008520662 A JP2008520662 A JP 2008520662A JP 2007543023 A JP2007543023 A JP 2007543023A JP 2007543023 A JP2007543023 A JP 2007543023A JP 2008520662 A JP2008520662 A JP 2008520662A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- compound
- methyl
- propyl
- 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
Links
- 0 *Oc1cnccc1 Chemical compound *Oc1cnccc1 0.000 description 51
- ASHMFMVNXDZCCZ-UHFFFAOYSA-N CC(C(C(C(C(C1O)O)O)OC1SC)NC(C1NCCCCC1)=O)Cl Chemical compound CC(C(C(C(C(C1O)O)O)OC1SC)NC(C1NCCCCC1)=O)Cl ASHMFMVNXDZCCZ-UHFFFAOYSA-N 0.000 description 3
- FMSUTHHSSIGUBD-NXFPAFRJSA-N CC(C(C(C(C1O)O)OC(C)C1O)NC(C1NCC[C@@H](C)CC1)=O)Cl Chemical compound CC(C(C(C(C1O)O)OC(C)C1O)NC(C1NCC[C@@H](C)CC1)=O)Cl FMSUTHHSSIGUBD-NXFPAFRJSA-N 0.000 description 1
- RYVNVPKJFNSIKU-UHFFFAOYSA-O CC(C)C=CCC1C=C(C([NH3+])=O)NC1 Chemical compound CC(C)C=CCC1C=C(C([NH3+])=O)NC1 RYVNVPKJFNSIKU-UHFFFAOYSA-O 0.000 description 1
- CUNRZNVDRORSMX-JTGQEONSSA-N CC(C)[C@H]([C@H]([C@@H](C([C@H]1O)O)O)O[C@@H]1SC)NC([C@H]1N(CC(O2)=C(C)OC2=O)CC[C@@H](CCCF)CC1)=O Chemical compound CC(C)[C@H]([C@H]([C@@H](C([C@H]1O)O)O)O[C@@H]1SC)NC([C@H]1N(CC(O2)=C(C)OC2=O)CC[C@@H](CCCF)CC1)=O CUNRZNVDRORSMX-JTGQEONSSA-N 0.000 description 1
- HOZCWGPEQKXDMB-CDFBBLPQSA-N CC(C)[C@H]([C@H]([C@@H]([C@@H]([C@H]1O)N=O)O)O[C@@H]1SC)NC([C@H]1N(CC(O2)=C(C)OC2=O)CCC(CCCCOc2cnccc2)CC1)=O Chemical compound CC(C)[C@H]([C@H]([C@@H]([C@@H]([C@H]1O)N=O)O)O[C@@H]1SC)NC([C@H]1N(CC(O2)=C(C)OC2=O)CCC(CCCCOc2cnccc2)CC1)=O HOZCWGPEQKXDMB-CDFBBLPQSA-N 0.000 description 1
- FNRVKRVKOLBJTE-FMGLVFKBSA-N CC(C)[C@H]([C@H]([C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1SC)NC([C@H]1NCC[C@@H](CCC[n]2nncc2)CC1)=O Chemical compound CC(C)[C@H]([C@H]([C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1SC)NC([C@H]1NCC[C@@H](CCC[n]2nncc2)CC1)=O FNRVKRVKOLBJTE-FMGLVFKBSA-N 0.000 description 1
- LSZBLENMTAJLHW-JFHPZKOPSA-N CC(C)[C@H]([C@H]([C@H](C)[C@@H]([C@H]1O)O)O[C@@H]1SC)NC([C@H]1N(CC(O2)=C(C)OC2=O)CC[C@@H](CCC(F)F)CC1)=O Chemical compound CC(C)[C@H]([C@H]([C@H](C)[C@@H]([C@H]1O)O)O[C@@H]1SC)NC([C@H]1N(CC(O2)=C(C)OC2=O)CC[C@@H](CCC(F)F)CC1)=O LSZBLENMTAJLHW-JFHPZKOPSA-N 0.000 description 1
- BOIBGNGBXLTMTQ-QWRGUYRKSA-N CC([C@H]1NCC[C@@H](CCCCl)CC1)=O Chemical compound CC([C@H]1NCC[C@@H](CCCCl)CC1)=O BOIBGNGBXLTMTQ-QWRGUYRKSA-N 0.000 description 1
- XAGBNYHHDFSROW-DRRXZNNHSA-N CC1(C)O[C@H]2[C@@H](/C=[N-](/Cc3ccccc3)\O)O[C@@H]3OC(C)(C)O[C@@H]3[C@H]2O1 Chemical compound CC1(C)O[C@H]2[C@@H](/C=[N-](/Cc3ccccc3)\O)O[C@@H]3OC(C)(C)O[C@@H]3[C@H]2O1 XAGBNYHHDFSROW-DRRXZNNHSA-N 0.000 description 1
- ORNWDNROILWGON-UHFFFAOYSA-O CCCC(C1)(CNC1=C1OC1[NH3+])F Chemical compound CCCC(C1)(CNC1=C1OC1[NH3+])F ORNWDNROILWGON-UHFFFAOYSA-O 0.000 description 1
- LPPWJXSOBVHNFF-UHFFFAOYSA-O CCCC1CC(C([NH3+])=O)NCC1 Chemical compound CCCC1CC(C([NH3+])=O)NCC1 LPPWJXSOBVHNFF-UHFFFAOYSA-O 0.000 description 1
- KGCOBPLLOPARPO-FNCVBFRFSA-N CCC[C@H]([C@@H]([C@@H](C1)O)O)O[C@@H]1SC Chemical compound CCC[C@H]([C@@H]([C@@H](C1)O)O)O[C@@H]1SC KGCOBPLLOPARPO-FNCVBFRFSA-N 0.000 description 1
- KQAVSDDONNBMCY-QMGXLNLGSA-N CCC[C@H]([C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1SC Chemical compound CCC[C@H]([C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1SC KQAVSDDONNBMCY-QMGXLNLGSA-N 0.000 description 1
- YYKXKPGHFPITLH-IWSPIJDZSA-N CCC[C@H]([C@@H]1O)OCC[C@H]1[O]#C Chemical compound CCC[C@H]([C@@H]1O)OCC[C@H]1[O]#C YYKXKPGHFPITLH-IWSPIJDZSA-N 0.000 description 1
- URMFHFVYCDGDEC-UHFFFAOYSA-N CCOc1cccnc1 Chemical compound CCOc1cccnc1 URMFHFVYCDGDEC-UHFFFAOYSA-N 0.000 description 1
- XQYGDRRJHQZINK-ZAIAIYBWSA-N C[C@H](CC1(C2=O)OC1CC(C1OC1)C2O)O Chemical compound C[C@H](CC1(C2=O)OC1CC(C1OC1)C2O)O XQYGDRRJHQZINK-ZAIAIYBWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/992,564 US7256177B2 (en) | 2003-06-17 | 2004-11-17 | Lincomycin derivatives possessing antibacterial activity |
| US11/217,836 US7361743B2 (en) | 2004-02-11 | 2005-08-31 | Lincomycin derivatives possessing antibacterial activity |
| PCT/US2005/031615 WO2006055070A2 (en) | 2004-11-17 | 2005-09-01 | Novel lincomycin derivatives possessing antibacterial activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008520662A true JP2008520662A (ja) | 2008-06-19 |
| JP2008520662A5 JP2008520662A5 (enExample) | 2008-10-16 |
Family
ID=36407579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007543023A Pending JP2008520662A (ja) | 2004-11-17 | 2005-09-01 | 抗微生物活性を有する新規リンコマイシン誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7361743B2 (enExample) |
| EP (1) | EP1814893A2 (enExample) |
| JP (1) | JP2008520662A (enExample) |
| CA (1) | CA2587797A1 (enExample) |
| WO (1) | WO2006055070A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016540045A (ja) * | 2013-11-15 | 2016-12-22 | ザ ウィスター インスティテュート オブ アナトミー アンド バイオロジー | Ebna1阻害剤およびそれらの使用方法 |
| JP2017222611A (ja) * | 2016-06-16 | 2017-12-21 | 学校法人上智学院 | ピペリジン化合物の製造方法 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1970377A4 (en) * | 2005-12-09 | 2013-02-27 | Meiji Seika Kaisha | LINCOMYCIN DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING THIS AS AN ACTIVE SUBSTANCE |
| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| EP2166015A4 (en) * | 2007-05-31 | 2012-09-05 | Meiji Seika Kaisha | LINCOSAMIDE DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING ACTIVE SUBSTANCE |
| EP2151447A4 (en) * | 2007-05-31 | 2012-09-05 | Meiji Seika Kaisha | LINCOMYCIN DERIVATIVES AND ANTIBACTERIAL AGENTS CONTAINING SAME AS ACTIVE INGREDIENTS |
| CN102964400B (zh) * | 2012-11-20 | 2015-08-05 | 广州白云山天心制药股份有限公司 | 一种不含去氢林可霉素的盐酸林可霉素制备方法 |
| CN104897896B (zh) * | 2015-04-14 | 2016-08-24 | 北京勤邦生物技术有限公司 | 一种林可霉素的磁免疫化学发光检测试剂盒及其应用 |
| JP6771491B2 (ja) | 2015-05-14 | 2020-10-21 | ザ ウィスター インスティテュート オブ アナトミー アンド バイオロジー | Ebna1阻害剤およびその使用方法 |
| CN104829660B (zh) * | 2015-05-27 | 2018-04-10 | 重庆药友制药有限责任公司 | 一种克林霉素磷酸酯的同分异构体 |
| WO2019032941A1 (en) * | 2017-08-10 | 2019-02-14 | President And Fellows Of Harvard College | NOVEL LINCOSAMIDE ANTIBIOTICS AND CORRESPONDING USES THEREOF |
| US11566039B2 (en) | 2017-08-10 | 2023-01-31 | President And Fellows Of Harvard College | Lincosamide antibiotics and uses thereof |
| WO2019032936A1 (en) | 2017-08-10 | 2019-02-14 | President Adn Fellows Of Harvard College | LINCONSAMIDE ANTIBIOTICS AND USES THEREOF |
| TW201946919A (zh) | 2018-05-17 | 2019-12-16 | 威斯塔研究所 | Ebna1抑制劑晶形、其製備方法及其使用方法 |
| EP3608326A1 (en) | 2018-08-10 | 2020-02-12 | Irbm S.P.A. | Tricyclic inhibitors of hepatitis b virus |
| EP4511043A1 (en) * | 2022-04-20 | 2025-02-26 | President and Fellows of Harvard College | Lincosamides and uses thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004016632A2 (en) * | 2002-08-15 | 2004-02-26 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| WO2005007665A2 (en) * | 2003-06-17 | 2005-01-27 | Vicuron Pharmaceuticals Inc. | Lincomycin derivatives possessing antibacterial activity |
| WO2005012320A2 (en) * | 2003-06-17 | 2005-02-10 | Vicuron Pharmaceuticals, Inc. | Novel lincomycin derivatives possessing antimicrobial activity |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2851463A (en) | 1956-04-09 | 1958-09-09 | Upjohn Co | Desalicetin and salts, and hydrocarbon carboxylic acid esters |
| US2928844A (en) | 1958-02-24 | 1960-03-15 | Upjohn Co | Celesticetin, its salts and method of preparation |
| US3086912A (en) | 1961-07-03 | 1963-04-23 | Upjohn Co | Antibiotic lincolnensin and method of production |
| US3268556A (en) | 1964-04-13 | 1966-08-23 | Upjohn Co | Novel lincomycin derivatives |
| US3255174A (en) | 1964-04-13 | 1966-06-07 | Upjohn Co | 7-0-methyl-n-acyl-3, 4-o-isopropylidene-1-deoxy-lincosamines |
| NL128232C (enExample) | 1964-04-13 | |||
| NL146501C (enExample) | 1964-07-01 | |||
| US3764672A (en) | 1964-08-05 | 1973-10-09 | Upjohn Co | Composition and process of treatment using lincomycin derivatives |
| US3380992A (en) | 1965-06-14 | 1968-04-30 | Upjohn Co | Lincomycin derivatives and process for preparing same |
| US3282917A (en) | 1964-08-17 | 1966-11-01 | Upjohn Co | Methyl n-(1-alkyl-4-alkoxy-prolyl)-alpha-thiolincosaminide compounds and process therefor |
| US3502648A (en) | 1965-02-08 | 1970-03-24 | Upjohn Co | 7-halo-7-deoxythiolincosaminides and process for preparing the same |
| NL140527B (nl) | 1965-02-08 | 1973-12-17 | Upjohn Co | Werkwijze ter bereiding van aan lincomycine verwante verbindingen. |
| US3496163A (en) | 1965-02-08 | 1970-02-17 | Upjohn Co | 7-halo-7-deoxylincomycins and process for preparing the same |
| US3435025A (en) | 1966-03-18 | 1969-03-25 | Upjohn Co | 7-deoxylincomycin and analogs and isomers thereof and process for making the same |
| US3475407A (en) | 1967-12-22 | 1969-10-28 | Upjohn Co | Process for preparing 7(r)- and 7(s)-halolincomycins |
| US3509127A (en) | 1968-04-30 | 1970-04-28 | Upjohn Co | Isologs of lincomycins and process for preparing the same |
| US3544551A (en) | 1968-04-30 | 1970-12-01 | Upjohn Co | 7-mercapto-7-deoxylincomycins and process for preparing the same |
| US3555007A (en) | 1968-07-22 | 1971-01-12 | Upjohn Co | 7-deoxy-7-halo lincomycin d derivatives |
| US3549615A (en) | 1968-10-17 | 1970-12-22 | Upjohn Co | Lincomycin derivatives and process for producing the same |
| US3702322A (en) | 1970-04-06 | 1972-11-07 | Upjohn Co | Derivatives of lincomycin and its analogs and process |
| DE2118636A1 (de) | 1970-04-20 | 1971-11-04 | The Upjohn Co., Kalamazoo, Mich. (V.StA.) | 3-Nucleotide von Lincomycin und deren Analogen, Verfahren zu ihrer Herstellung und ihre Verwendung in therapeutischen Präparaten |
| US3692767A (en) | 1970-05-06 | 1972-09-19 | Upjohn Co | Process for making lincomycin and analogs thereof and novel compounds obtained thereby |
| US3714141A (en) | 1970-05-26 | 1973-01-30 | Upjohn Co | Process for making 7-halolincomycins |
| US3674647A (en) | 1970-10-07 | 1972-07-04 | Upjohn Co | Preparation of lincomycin analogues |
| US3715346A (en) | 1970-11-18 | 1973-02-06 | Upjohn Co | Process for the preparation of lincomycin compounds |
| US3671647A (en) | 1971-03-24 | 1972-06-20 | Upjohn Co | Lincomycin 3-nucleotides and the salts thereof |
| US3892729A (en) | 1971-06-23 | 1975-07-01 | Upjohn Co | 1{40 (Beta-hydroxyethyl)-1{40 -demethyl clindamycin 2-phosphates |
| US3787390A (en) | 1971-06-23 | 1974-01-22 | Upjohn Co | Analogs of lincomycin and process |
| US3892730A (en) | 1971-06-23 | 1975-07-01 | Upjohn Co | 1{40 -({62 -hydroxyethyl)-1{40 -demethyl clindamycin 2-acylates |
| US3856943A (en) | 1971-06-23 | 1974-12-24 | Upjohn Co | Compositions and process |
| US3915954A (en) | 1971-11-15 | 1975-10-28 | Upjohn Co | Derivatives of lincomycin and its analogs and process |
| BE793630A (fr) | 1972-01-03 | 1973-07-03 | Upjohn Co | Nouvel antibiotique de la classe des celesticetines et son procede de preparation |
| US3853843A (en) | 1972-12-13 | 1974-12-10 | Upjohn Co | Derivatives of thiolincosaminide compounds |
| US3849396A (en) | 1973-01-08 | 1974-11-19 | Upjohn Co | Lincomycin and clindamycin 1-o-ethers |
| US3870699A (en) | 1973-03-06 | 1975-03-11 | Upjohn Co | Lincomycin analogs |
| US3833475A (en) | 1973-04-23 | 1974-09-03 | Upjohn Co | Process for preparing lincomycin |
| US4271266A (en) | 1974-06-10 | 1981-06-02 | The Upjohn Manufacturing Company | Process for preparing lincomycin |
| US4031304A (en) | 1976-01-30 | 1977-06-21 | The Upjohn Company | Process for preparing lincomycin derivatives |
| US4278789A (en) | 1979-11-23 | 1981-07-14 | The Upjohn Company | Lincomycin compounds |
| US4310660A (en) | 1980-05-19 | 1982-01-12 | The Upjohn Company | Lincomycin compounds |
| US4309533A (en) | 1980-05-19 | 1982-01-05 | The Upjohn Company | Lincomycin compounds |
| US4293547A (en) | 1980-08-25 | 1981-10-06 | The Upjohn Company | Method of treating malaria |
| US4317903A (en) | 1981-01-26 | 1982-03-02 | The Upjohn Company | Process for the purification of lincomycin |
| US4383109A (en) | 1981-04-20 | 1983-05-10 | The Upjohn Company | Lincomycin nucleotides |
| US4464466A (en) | 1981-04-20 | 1984-08-07 | The Upjohn Company | Process of producing lincomycin nucleotides |
| US4430495A (en) | 1982-09-17 | 1984-02-07 | The Upjohn Company | Process for preparing lincomycin and clindamycin ribonucleotides |
| US4568741A (en) | 1984-05-15 | 1986-02-04 | The Upjohn Company | Synthesis of 7-halo-7-deoxylincomycins |
| CN1004002B (zh) | 1984-11-29 | 1989-04-26 | 厄普约翰公司 | 制备7-卤-7-去氧林可霉素及其类似化合物的改进方法 |
| WO1989004672A1 (en) | 1987-11-20 | 1989-06-01 | The Upjohn Company | Derivatives of lincosaminide antibiotics |
| US5182374A (en) * | 1990-03-21 | 1993-01-26 | American Cyanamid Company | Clindamycin phosphate synthesis |
| US6288234B1 (en) | 1998-06-08 | 2001-09-11 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
-
2005
- 2005-08-31 US US11/217,836 patent/US7361743B2/en not_active Expired - Fee Related
- 2005-09-01 JP JP2007543023A patent/JP2008520662A/ja active Pending
- 2005-09-01 CA CA002587797A patent/CA2587797A1/en not_active Abandoned
- 2005-09-01 WO PCT/US2005/031615 patent/WO2006055070A2/en not_active Ceased
- 2005-09-01 EP EP05794095A patent/EP1814893A2/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004016632A2 (en) * | 2002-08-15 | 2004-02-26 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| WO2005007665A2 (en) * | 2003-06-17 | 2005-01-27 | Vicuron Pharmaceuticals Inc. | Lincomycin derivatives possessing antibacterial activity |
| WO2005012320A2 (en) * | 2003-06-17 | 2005-02-10 | Vicuron Pharmaceuticals, Inc. | Novel lincomycin derivatives possessing antimicrobial activity |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016540045A (ja) * | 2013-11-15 | 2016-12-22 | ザ ウィスター インスティテュート オブ アナトミー アンド バイオロジー | Ebna1阻害剤およびそれらの使用方法 |
| US11242317B2 (en) | 2013-11-15 | 2022-02-08 | The Wistar Institute Of Anatomy And Biology | EBNA1 inhibitors and their method of use |
| US12258314B2 (en) | 2013-11-15 | 2025-03-25 | The Wistar Institute Of Anatomy And Biology | EBNA1 inhibitors and their method of use |
| JP2017222611A (ja) * | 2016-06-16 | 2017-12-21 | 学校法人上智学院 | ピペリジン化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006055070A2 (en) | 2006-05-26 |
| EP1814893A2 (en) | 2007-08-08 |
| US7361743B2 (en) | 2008-04-22 |
| US20060148722A1 (en) | 2006-07-06 |
| CA2587797A1 (en) | 2006-05-26 |
| WO2006055070A3 (en) | 2006-07-20 |
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