CN100362005C - 钌的抗癌络合物 - Google Patents
钌的抗癌络合物 Download PDFInfo
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- CN100362005C CN100362005C CNB038160005A CN03816000A CN100362005C CN 100362005 C CN100362005 C CN 100362005C CN B038160005 A CNB038160005 A CN B038160005A CN 03816000 A CN03816000 A CN 03816000A CN 100362005 C CN100362005 C CN 100362005C
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title description 9
- 229910052707 ruthenium Inorganic materials 0.000 title description 8
- 230000001093 anti-cancer Effects 0.000 title description 6
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- 230000002265 prevention Effects 0.000 claims abstract 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052736 halogen Chemical group 0.000 claims description 22
- 150000002367 halogens Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052727 yttrium Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
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- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 abstract description 7
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- 125000003118 aryl group Chemical group 0.000 description 27
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 24
- 125000003710 aryl alkyl group Chemical group 0.000 description 22
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
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- 125000001118 alkylidene group Chemical group 0.000 description 9
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- 125000000623 heterocyclic group Chemical group 0.000 description 9
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 8
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- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 7
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- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012327 Ruthenium complex Substances 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
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- 239000002126 C01EB10 - Adenosine Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 3
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910019946 S-S Inorganic materials 0.000 description 3
- 229910019939 S—S Inorganic materials 0.000 description 3
- 125000005595 acetylacetonate group Chemical group 0.000 description 3
- 229960005305 adenosine Drugs 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229940029575 guanosine Drugs 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
- 229930024421 Adenine Natural products 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZHPMMPCSVDYNIQ-UHFFFAOYSA-N O.[Na].C(C)C(=O)C(=O)C Chemical compound O.[Na].C(C)C(=O)C(=O)C ZHPMMPCSVDYNIQ-UHFFFAOYSA-N 0.000 description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 125000004450 alkenylene group Chemical group 0.000 description 2
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- 150000002475 indoles Chemical class 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
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- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 description 1
- FTDLXZYXJAJLIP-UHFFFAOYSA-N 1,4-dihydroanthracene Chemical compound C1=CC=C2C=C3CC=CCC3=CC2=C1 FTDLXZYXJAJLIP-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
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- PJWUXKNZVMEPPH-UHFFFAOYSA-N N-[2-(methylamino)ethyl]isoquinoline-5-sulfonamide Chemical group N1=CC=C2C(S(=O)(=O)NCCNC)=CC=CC2=C1 PJWUXKNZVMEPPH-UHFFFAOYSA-N 0.000 description 1
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- QYBFRILKKAVWEP-UHFFFAOYSA-L benzene;2-(2-methyl-5-nitroimidazol-1-yl)ethanol;ruthenium(2+);dichloride Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1.CC1=NC=C([N+]([O-])=O)N1CCO QYBFRILKKAVWEP-UHFFFAOYSA-L 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0215526.5 | 2002-07-05 | ||
| GBGB0215526.5A GB0215526D0 (en) | 2002-07-05 | 2002-07-05 | Anticancer compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1665826A CN1665826A (zh) | 2005-09-07 |
| CN100362005C true CN100362005C (zh) | 2008-01-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB038160005A Expired - Fee Related CN100362005C (zh) | 2002-07-05 | 2003-07-04 | 钌的抗癌络合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20060058270A1 (enExample) |
| EP (1) | EP1558620B1 (enExample) |
| JP (1) | JP2005536487A (enExample) |
| KR (1) | KR20050053589A (enExample) |
| CN (1) | CN100362005C (enExample) |
| AT (1) | ATE407937T1 (enExample) |
| AU (1) | AU2003251159B2 (enExample) |
| BR (1) | BR0312470A (enExample) |
| CA (1) | CA2491640A1 (enExample) |
| DE (1) | DE60323529D1 (enExample) |
| DK (1) | DK1558620T3 (enExample) |
| ES (1) | ES2314245T3 (enExample) |
| GB (1) | GB0215526D0 (enExample) |
| MX (1) | MXPA05000314A (enExample) |
| NO (1) | NO20050640L (enExample) |
| NZ (1) | NZ538005A (enExample) |
| PL (1) | PL373049A1 (enExample) |
| PT (1) | PT1558620E (enExample) |
| WO (1) | WO2004005304A1 (enExample) |
| ZA (1) | ZA200500908B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE303393T1 (de) * | 1999-10-27 | 2005-09-15 | Univ Court The University Of E | Halbsandwich ruthenium(ii)-verbindungen mit einem stickstoff-haltigen liganden zur krebstherapie |
| KR20060023526A (ko) | 2003-04-30 | 2006-03-14 | 유니버시티 오브 코트 오브 더 유니버시티 오브 에딘버그 | 종양 치료를 위한 루테늄〔ｉｉ〕 착물 |
| GB0418643D0 (en) * | 2004-08-20 | 2004-09-22 | Univ Edinburgh | Ruthenium (II) compounds |
| GB0604602D0 (en) * | 2006-03-07 | 2006-04-19 | Univ Edinburgh | Ruthenium (II) compounds |
| WO2007128158A1 (en) | 2006-05-09 | 2007-11-15 | Ecole Polytechnique Federale De Lausanne (Epfl) | Transition metal complexes for inhibiting resistance in the treatment of cancer and metastasis |
| GB0610062D0 (en) * | 2006-05-19 | 2006-06-28 | Univ Edinburgh | Ruthenium (ll) compounds |
| DE102009053392A1 (de) * | 2009-11-14 | 2011-06-22 | Umicore AG & Co. KG, 63457 | Verfahren zur Herstellung von Ru(0) Olefin-Komplexen |
| WO2013038395A1 (en) | 2011-09-16 | 2013-03-21 | Universidade De Lisboa | Transition metal complexes for pharmaceutical applications |
| WO2013136296A2 (en) | 2012-03-14 | 2013-09-19 | Universidade De Lisboa | Water-soluble organometallic ruthenium and iron compunds presenting heteroaromatic ligands |
| CN103360428A (zh) * | 2012-04-09 | 2013-10-23 | 中国科学院化学研究所 | 抑制蛋白酪氨酸磷酸酶1b活性的含钌配合物及其制备方法和蛋白酪氨酸磷酸酶1b抑制剂 |
| CN102964385B (zh) * | 2012-11-30 | 2015-02-18 | 广西师范学院 | 一种有机金属钌化合物及其制备方法和用途 |
| US9751081B2 (en) | 2014-12-01 | 2017-09-05 | Clemson University | Self-regenerating antioxidant catalysts and methods of using the same |
| CZ310511B6 (cs) * | 2023-09-18 | 2025-09-10 | Univerzita Palackého v Olomouci | Koordinační sloučeniny osmia pro použití pro léčbu plicních nádorových onemocnění |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001030790A1 (en) * | 1999-10-27 | 2001-05-03 | The University Court, The University Of Edinburgh | Half-sandwich ruthenium (ii) compounds comprising nitrogen containing ligands for treatment of cancer |
| WO2002002572A1 (en) * | 2000-06-30 | 2002-01-10 | The University Court, The University Of Edinburgh | Ruthenium (ii) compounds for use in the therapy of cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980473A (en) * | 1985-01-18 | 1990-12-25 | The Trustees Of Columbia University In The City Of New York | Chemical probes for left-handed DNA and chiral metal complexes as Z-specific anti-tumor agents |
| DE69635874T2 (de) * | 1995-12-06 | 2006-12-14 | Japan Science And Technology Agency, Kawaguchi | Verfahren zur Herstellung von optisch aktiven Alkoholen |
-
2002
- 2002-07-05 GB GBGB0215526.5A patent/GB0215526D0/en not_active Ceased
-
2003
- 2003-07-04 JP JP2004518958A patent/JP2005536487A/ja active Pending
- 2003-07-04 EP EP03762788A patent/EP1558620B1/en not_active Expired - Lifetime
- 2003-07-04 CN CNB038160005A patent/CN100362005C/zh not_active Expired - Fee Related
- 2003-07-04 MX MXPA05000314A patent/MXPA05000314A/es active IP Right Grant
- 2003-07-04 US US10/520,239 patent/US20060058270A1/en not_active Abandoned
- 2003-07-04 AU AU2003251159A patent/AU2003251159B2/en not_active Ceased
- 2003-07-04 BR BR0312470-3A patent/BR0312470A/pt not_active IP Right Cessation
- 2003-07-04 CA CA002491640A patent/CA2491640A1/en not_active Abandoned
- 2003-07-04 WO PCT/GB2003/002879 patent/WO2004005304A1/en not_active Ceased
- 2003-07-04 DK DK03762788T patent/DK1558620T3/da active
- 2003-07-04 NZ NZ538005A patent/NZ538005A/en unknown
- 2003-07-04 AT AT03762788T patent/ATE407937T1/de not_active IP Right Cessation
- 2003-07-04 DE DE60323529T patent/DE60323529D1/de not_active Expired - Fee Related
- 2003-07-04 PL PL03373049A patent/PL373049A1/xx not_active Application Discontinuation
- 2003-07-04 PT PT03762788T patent/PT1558620E/pt unknown
- 2003-07-04 ES ES03762788T patent/ES2314245T3/es not_active Expired - Lifetime
- 2003-07-04 KR KR1020057000143A patent/KR20050053589A/ko not_active Ceased
-
2005
- 2005-02-01 ZA ZA200500908A patent/ZA200500908B/xx unknown
- 2005-02-04 NO NO20050640A patent/NO20050640L/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001030790A1 (en) * | 1999-10-27 | 2001-05-03 | The University Court, The University Of Edinburgh | Half-sandwich ruthenium (ii) compounds comprising nitrogen containing ligands for treatment of cancer |
| WO2002002572A1 (en) * | 2000-06-30 | 2002-01-10 | The University Court, The University Of Edinburgh | Ruthenium (ii) compounds for use in the therapy of cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004005304A1 (en) | 2004-01-15 |
| DE60323529D1 (de) | 2008-10-23 |
| CN1665826A (zh) | 2005-09-07 |
| BR0312470A (pt) | 2005-04-26 |
| ZA200500908B (en) | 2006-03-29 |
| DK1558620T3 (da) | 2009-01-05 |
| EP1558620B1 (en) | 2008-09-10 |
| ES2314245T3 (es) | 2009-03-16 |
| NZ538005A (en) | 2007-08-31 |
| MXPA05000314A (es) | 2005-09-20 |
| US20060058270A1 (en) | 2006-03-16 |
| PT1558620E (pt) | 2008-12-03 |
| NO20050640L (no) | 2005-03-22 |
| CA2491640A1 (en) | 2004-01-15 |
| AU2003251159B2 (en) | 2008-11-06 |
| ATE407937T1 (de) | 2008-09-15 |
| KR20050053589A (ko) | 2005-06-08 |
| GB0215526D0 (en) | 2002-08-14 |
| JP2005536487A (ja) | 2005-12-02 |
| PL373049A1 (en) | 2005-08-08 |
| AU2003251159A1 (en) | 2004-01-23 |
| EP1558620A1 (en) | 2005-08-03 |
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