ZA200107313B - Water soluble transplatinum complexes with anti-cancer activity and method of using same. - Google Patents
Water soluble transplatinum complexes with anti-cancer activity and method of using same. Download PDFInfo
- Publication number
- ZA200107313B ZA200107313B ZA200107313A ZA200107313A ZA200107313B ZA 200107313 B ZA200107313 B ZA 200107313B ZA 200107313 A ZA200107313 A ZA 200107313A ZA 200107313 A ZA200107313 A ZA 200107313A ZA 200107313 B ZA200107313 B ZA 200107313B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- trans
- group
- nitrogen atom
- planar
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 10
- 230000001093 anti-cancer Effects 0.000 title description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 9
- 229960004316 cisplatin Drugs 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- ORAKNQSHWMHCEY-UHFFFAOYSA-N methyl 2-pyridin-2-ylacetate Chemical compound COC(=O)CC1=CC=CC=N1 ORAKNQSHWMHCEY-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 1
- 150000001251 acridines Chemical class 0.000 claims 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 150000002537 isoquinolines Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000002916 oxazoles Chemical class 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000003248 quinolines Chemical class 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 230000001472 cytotoxic effect Effects 0.000 description 5
- 230000003013 cytotoxicity Effects 0.000 description 5
- 231100000135 cytotoxicity Toxicity 0.000 description 5
- BSJGASKRWFKGMV-UHFFFAOYSA-L ammonia dichloroplatinum(2+) Chemical compound N.N.Cl[Pt+2]Cl BSJGASKRWFKGMV-UHFFFAOYSA-L 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 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 4
- 239000013522 chelant Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 101100522123 Caenorhabditis elegans ptc-1 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229960004562 carboplatin Drugs 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005556 structure-activity relationship Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- MQVISALTZUNQSK-UHFFFAOYSA-N 2-pyridin-2-ylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=N1 MQVISALTZUNQSK-UHFFFAOYSA-N 0.000 description 1
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-L cyclobutane-1,1-dicarboxylate(2-) Chemical compound [O-]C(=O)C1(C([O-])=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-L 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- -1 suitable elixirs Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- 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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/263,222 US6001872A (en) | 1999-03-05 | 1999-03-05 | Water soluble transplatinum complexes with anti-cancer activity and method of using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200107313B true ZA200107313B (en) | 2002-06-11 |
Family
ID=23000879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200107313A ZA200107313B (en) | 1999-03-05 | 2001-09-04 | Water soluble transplatinum complexes with anti-cancer activity and method of using same. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6001872A (fr) |
| EP (1) | EP1158974A4 (fr) |
| JP (1) | JP2002538116A (fr) |
| KR (1) | KR20010102495A (fr) |
| AU (1) | AU763823B2 (fr) |
| BR (1) | BR0009246A (fr) |
| CA (1) | CA2366048A1 (fr) |
| CZ (1) | CZ20013181A3 (fr) |
| EA (1) | EA004589B1 (fr) |
| MX (1) | MXPA01008991A (fr) |
| WO (1) | WO2000051600A1 (fr) |
| ZA (1) | ZA200107313B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6001872A (en) * | 1999-03-05 | 1999-12-14 | Virginia Commonwealth University | Water soluble transplatinum complexes with anti-cancer activity and method of using same |
| KR100314720B1 (ko) * | 1999-03-26 | 2001-11-26 | 박호군 | 포스파젠 삼합체에 도입된 백금 착물, 그의 제조방법 및 그를 유효성분으로 하는 항암제 |
| ES2257178B1 (es) * | 2004-09-30 | 2007-08-16 | Universidad Autonoma De Madrid | Compuestos de platino de formula trans-(ptc12(isopropilamina)(4-(hidroximetil)-piridina)) y trans-(ptc12(isopropilamina)(3-hidroximetil)-piridina y su aplicacion como farmaco antitumoral. |
| US12023341B2 (en) | 2020-04-20 | 2024-07-02 | Wake Forest University | Platinum-acridine compounds and methods of treating cancers |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5562925A (en) * | 1970-04-20 | 1996-10-08 | Research Corporation Tech. Inc. | Anti-tumor method |
| US5107007A (en) * | 1989-09-01 | 1992-04-21 | The University Of Vermont And State Agricultural College | Bis-platinum complexes as chemotherapeutic agents |
| US5770591A (en) * | 1986-07-25 | 1998-06-23 | The University Of Vermont And State Agricultural College | Bis-platinum complexes as chemotherapeutic agents |
| US5026694A (en) * | 1987-04-13 | 1991-06-25 | The British Columbia Cancer Foundation | Platinum complexes with one radiosensitizing ligand |
| US4996337A (en) * | 1987-06-23 | 1991-02-26 | American Cyanamid Company | Synthesis of cisplatin analogs |
| US4937358A (en) * | 1987-06-23 | 1990-06-26 | American Cyanamid Company | Synthesis of cisplatin analogs |
| JPH08176176A (ja) * | 1994-12-26 | 1996-07-09 | Ss Pharmaceut Co Ltd | 白金錯体及びこれを含有する悪性腫瘍治療剤 |
| GB9502799D0 (en) * | 1995-02-14 | 1995-04-05 | Johnson Matthey Plc | Improvements in platinum complexes |
| US6001872A (en) * | 1999-03-05 | 1999-12-14 | Virginia Commonwealth University | Water soluble transplatinum complexes with anti-cancer activity and method of using same |
-
1999
- 1999-03-05 US US09/263,222 patent/US6001872A/en not_active Expired - Fee Related
-
2000
- 2000-03-02 JP JP2000602068A patent/JP2002538116A/ja active Pending
- 2000-03-02 CZ CZ20013181A patent/CZ20013181A3/cs unknown
- 2000-03-02 KR KR1020017011259A patent/KR20010102495A/ko not_active Application Discontinuation
- 2000-03-02 WO PCT/US2000/005383 patent/WO2000051600A1/fr not_active Application Discontinuation
- 2000-03-02 AU AU38628/00A patent/AU763823B2/en not_active Ceased
- 2000-03-02 BR BR0009246-0A patent/BR0009246A/pt not_active IP Right Cessation
- 2000-03-02 EP EP00917695A patent/EP1158974A4/fr not_active Withdrawn
- 2000-03-02 CA CA002366048A patent/CA2366048A1/fr not_active Abandoned
- 2000-03-02 EA EA200100940A patent/EA004589B1/ru not_active IP Right Cessation
- 2000-03-02 MX MXPA01008991A patent/MXPA01008991A/es unknown
-
2001
- 2001-09-04 ZA ZA200107313A patent/ZA200107313B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA01008991A (es) | 2002-09-18 |
| EP1158974A1 (fr) | 2001-12-05 |
| CZ20013181A3 (cs) | 2002-01-16 |
| AU3862800A (en) | 2000-09-21 |
| AU763823B2 (en) | 2003-07-31 |
| EP1158974A4 (fr) | 2002-06-05 |
| BR0009246A (pt) | 2002-01-22 |
| WO2000051600A1 (fr) | 2000-09-08 |
| JP2002538116A (ja) | 2002-11-12 |
| EA200100940A1 (ru) | 2002-04-25 |
| EA004589B1 (ru) | 2004-06-24 |
| CA2366048A1 (fr) | 2000-09-08 |
| US6001872A (en) | 1999-12-14 |
| KR20010102495A (ko) | 2001-11-15 |
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