RU2262506C2 - Таксаны, фармацевтические композиции, способ ингибирования - Google Patents
Таксаны, фармацевтические композиции, способ ингибирования Download PDFInfo
- Publication number
- RU2262506C2 RU2262506C2 RU2001129501/04A RU2001129501A RU2262506C2 RU 2262506 C2 RU2262506 C2 RU 2262506C2 RU 2001129501/04 A RU2001129501/04 A RU 2001129501/04A RU 2001129501 A RU2001129501 A RU 2001129501A RU 2262506 C2 RU2262506 C2 RU 2262506C2
- Authority
- RU
- Russia
- Prior art keywords
- coo
- furyl
- thienyl
- pyridyl
- coox
- Prior art date
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- 229940123237 Taxane Drugs 0.000 title claims abstract description 58
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 21
- 230000005764 inhibitory process Effects 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 74
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 58
- 230000000259 anti-tumor effect Effects 0.000 claims abstract description 42
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims abstract 25
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- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 3
- -1 isobutenyl Chemical group 0.000 claims description 126
- 125000002541 furyl group Chemical group 0.000 claims description 57
- 125000001544 thienyl group Chemical group 0.000 claims description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 47
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 46
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 26
- 125000000468 ketone group Chemical group 0.000 claims description 17
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 9
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 9
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- 239000012188 paraffin wax Substances 0.000 description 1
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- 229940049954 penicillin Drugs 0.000 description 1
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- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
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- 230000000069 prophylactic effect Effects 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
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- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003641 trioses Chemical class 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/75—Aerosol containers not provided for in groups B65D83/16 - B65D83/74
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17978200P | 2000-02-02 | 2000-02-02 | |
| US60/179782 | 2000-02-02 | ||
| US60/179,792 | 2000-02-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2001129501A RU2001129501A (ru) | 2003-07-10 |
| RU2262506C2 true RU2262506C2 (ru) | 2005-10-20 |
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|---|---|---|---|
| RU2001129501/04A RU2262506C2 (ru) | 2000-02-02 | 2001-02-02 | Таксаны, фармацевтические композиции, способ ингибирования |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1165553B1 (enExample) |
| JP (1) | JP2003522172A (enExample) |
| CN (1) | CN1380882A (enExample) |
| AT (1) | ATE432928T1 (enExample) |
| AU (1) | AU782150B2 (enExample) |
| BG (1) | BG64889B1 (enExample) |
| BR (1) | BR0104354A (enExample) |
| CA (1) | CA2368274C (enExample) |
| CZ (1) | CZ20013430A3 (enExample) |
| DE (1) | DE60138853D1 (enExample) |
| GE (1) | GEP20043323B (enExample) |
| HU (1) | HUP0600302A2 (enExample) |
| IL (1) | IL145638A (enExample) |
| MX (1) | MXPA01009905A (enExample) |
| NO (1) | NO327910B1 (enExample) |
| NZ (1) | NZ514382A (enExample) |
| PL (1) | PL202957B1 (enExample) |
| RO (1) | RO121270B1 (enExample) |
| RU (1) | RU2262506C2 (enExample) |
| SK (1) | SK13692001A3 (enExample) |
| TR (1) | TR200102858T1 (enExample) |
| TW (1) | TWI299732B (enExample) |
| UA (1) | UA75039C2 (enExample) |
| WO (1) | WO2001057032A1 (enExample) |
| ZA (1) | ZA200108055B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6649632B2 (en) | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
| CA2354471A1 (en) * | 2001-07-31 | 2003-01-31 | Florida State University Research Foundation, Inc. | C10 ester substituted taxanes |
| SG129990A1 (en) * | 2001-08-01 | 2007-03-20 | Univ Florida State Res Found | C10 ester substituted taxanes |
| SV2006002010A (es) | 2004-02-13 | 2006-08-23 | Univ Florida State Res Found | Taxanos sustituidos con esteres de ciclopentilo en c10 |
| WO2006088767A2 (en) * | 2005-02-14 | 2006-08-24 | Florida State University Research Foundation, Inc. | C10 cyclopropyl ester substituted taxane compositions |
| US8242166B2 (en) | 2008-03-31 | 2012-08-14 | Florida State University Research Foundation, Inc. | C(10) ethyl ester and C(10) cyclopropyl ester substituted taxanes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2137764C1 (ru) * | 1993-03-26 | 1999-09-20 | Дзе Рисерч Фаундейшн оф Дзе Стейт Юниверсити оф Нью-Йорк | Производные таксана, способ их получения, фармацевтическая композиция и способ лечения |
| EP0534709B1 (en) * | 1991-09-23 | 2003-01-15 | Florida State University | Substituted taxanes as antitumour agents |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5243045A (en) * | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
| IL108443A0 (en) * | 1993-01-29 | 1994-04-12 | Univ Florida State | C7 taxane derivatives and pharmaceutical compositions containing them |
| CA2158863C (en) * | 1993-03-22 | 2006-12-19 | Robert A. Holton | Taxanes having a pyridyl substituted side-chain |
| EP0690711B1 (en) * | 1993-03-22 | 2000-08-16 | Florida State University | Taxanes having an amino substituted side-chain |
| PT1228759E (pt) * | 1993-03-22 | 2005-04-29 | Univ Florida State | Composicoes farmaceuticas contendo um taxano possuindo uma cadeia lateral substituida com furilo ou tienilo |
| US6100411A (en) * | 1994-10-28 | 2000-08-08 | The Research Foundation Of State University Of New York | Taxoid anti-tumor agents and pharmaceutical compositions thereof |
| WO1996013495A1 (en) * | 1994-10-28 | 1996-05-09 | The Research Foundation Of State University Of New York | Taxoid derivatives, their preparation and their use as antitumor agents |
| CA2255615C (en) * | 1996-05-22 | 2006-08-29 | Neuromedica, Inc. | Compositions comprising conjugates of cis-docosahexaenoic acid and docetaxel |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| AU758418B2 (en) * | 1997-12-19 | 2003-03-20 | Kabushiki Kaisha Yakult Honsha | Taxane derivatives |
| JP2003026673A (ja) * | 1999-03-05 | 2003-01-29 | Asahi Kasei Corp | 骨形成促進剤 |
-
2001
- 2001-02-02 RO ROA200101083A patent/RO121270B1/ro unknown
- 2001-02-02 CA CA002368274A patent/CA2368274C/en not_active Expired - Fee Related
- 2001-02-02 HU HU0600302A patent/HUP0600302A2/hu unknown
- 2001-02-02 CN CN01800568A patent/CN1380882A/zh active Pending
- 2001-02-02 SK SK1369-2001A patent/SK13692001A3/sk unknown
- 2001-02-02 IL IL145638A patent/IL145638A/en not_active IP Right Cessation
- 2001-02-02 PL PL351380A patent/PL202957B1/pl not_active IP Right Cessation
- 2001-02-02 JP JP2001557864A patent/JP2003522172A/ja active Pending
- 2001-02-02 GE GE4523A patent/GEP20043323B/en unknown
- 2001-02-02 WO PCT/US2001/003623 patent/WO2001057032A1/en not_active Ceased
- 2001-02-02 CZ CZ20013430A patent/CZ20013430A3/cs unknown
- 2001-02-02 NZ NZ514382A patent/NZ514382A/en unknown
- 2001-02-02 UA UA2001106733A patent/UA75039C2/uk unknown
- 2001-02-02 AT AT01906971T patent/ATE432928T1/de not_active IP Right Cessation
- 2001-02-02 DE DE60138853T patent/DE60138853D1/de not_active Expired - Lifetime
- 2001-02-02 EP EP01906971A patent/EP1165553B1/en not_active Expired - Lifetime
- 2001-02-02 MX MXPA01009905A patent/MXPA01009905A/es active IP Right Grant
- 2001-02-02 RU RU2001129501/04A patent/RU2262506C2/ru active
- 2001-02-02 AU AU34809/01A patent/AU782150B2/en not_active Ceased
- 2001-02-02 BR BR0104354-4A patent/BR0104354A/pt not_active IP Right Cessation
- 2001-02-02 TR TR2001/02858T patent/TR200102858T1/xx unknown
- 2001-03-27 TW TW090102238A patent/TWI299732B/zh not_active IP Right Cessation
- 2001-10-01 NO NO20014754A patent/NO327910B1/no not_active IP Right Cessation
- 2001-10-01 ZA ZA200108055A patent/ZA200108055B/en unknown
- 2001-10-01 BG BG105965A patent/BG64889B1/bg unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0534709B1 (en) * | 1991-09-23 | 2003-01-15 | Florida State University | Substituted taxanes as antitumour agents |
| RU2137764C1 (ru) * | 1993-03-26 | 1999-09-20 | Дзе Рисерч Фаундейшн оф Дзе Стейт Юниверсити оф Нью-Йорк | Производные таксана, способ их получения, фармацевтическая композиция и способ лечения |
Non-Patent Citations (1)
| Title |
|---|
| W0 9732578, 12.09.1997. * |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0600302A2 (en) | 2006-07-28 |
| TR200102858T1 (tr) | 2002-12-23 |
| PL351380A1 (en) | 2003-04-07 |
| ATE432928T1 (de) | 2009-06-15 |
| BG64889B1 (bg) | 2006-08-31 |
| IL145638A (en) | 2011-05-31 |
| IL145638A0 (en) | 2002-06-30 |
| GEP20043323B (en) | 2004-02-10 |
| AU3480901A (en) | 2001-08-14 |
| SK13692001A3 (sk) | 2002-07-02 |
| NZ514382A (en) | 2004-05-28 |
| JP2003522172A (ja) | 2003-07-22 |
| TWI299732B (en) | 2008-08-11 |
| EP1165553B1 (en) | 2009-06-03 |
| RO121270B1 (ro) | 2007-02-28 |
| PL202957B1 (pl) | 2009-08-31 |
| CZ20013430A3 (cs) | 2002-04-17 |
| BR0104354A (pt) | 2002-01-02 |
| EP1165553A1 (en) | 2002-01-02 |
| NO20014754D0 (no) | 2001-10-01 |
| AU782150B2 (en) | 2005-07-07 |
| BG105965A (en) | 2002-07-31 |
| UA75039C2 (en) | 2006-03-15 |
| NO327910B1 (no) | 2009-10-19 |
| NO20014754L (no) | 2001-11-29 |
| CN1380882A (zh) | 2002-11-20 |
| ZA200108055B (en) | 2003-12-01 |
| CA2368274C (en) | 2009-10-13 |
| CA2368274A1 (en) | 2001-08-09 |
| MXPA01009905A (es) | 2003-08-20 |
| DE60138853D1 (de) | 2009-07-16 |
| WO2001057032A1 (en) | 2001-08-09 |
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