HRP20030674A2 - Pharmaceutical dosage forms of epothilones for oral administration - Google Patents
Pharmaceutical dosage forms of epothilones for oral administration Download PDFInfo
- Publication number
- HRP20030674A2 HRP20030674A2 HR20030674A HRP20030674A HRP20030674A2 HR P20030674 A2 HRP20030674 A2 HR P20030674A2 HR 20030674 A HR20030674 A HR 20030674A HR P20030674 A HRP20030674 A HR P20030674A HR P20030674 A2 HRP20030674 A2 HR P20030674A2
- Authority
- HR
- Croatia
- Prior art keywords
- pharmaceutically acceptable
- alkyl
- group
- buffer
- epothilone
- Prior art date
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- 229930013356 epothilone Natural products 0.000 title claims description 166
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 title claims description 84
- 239000002552 dosage form Substances 0.000 title description 39
- 239000000872 buffer Substances 0.000 claims description 110
- 239000002253 acid Substances 0.000 claims description 107
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 93
- 239000007788 liquid Substances 0.000 claims description 89
- 150000003883 epothilone derivatives Chemical class 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 77
- 239000000651 prodrug Substances 0.000 claims description 70
- 229940002612 prodrug Drugs 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 64
- 239000012453 solvate Substances 0.000 claims description 64
- 239000006186 oral dosage form Substances 0.000 claims description 60
- 230000003472 neutralizing effect Effects 0.000 claims description 59
- 239000000243 solution Substances 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 48
- -1 clathrates Chemical class 0.000 claims description 45
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 38
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000003107 substituted aryl group Chemical group 0.000 claims description 31
- 238000006386 neutralization reaction Methods 0.000 claims description 30
- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 26
- 150000004677 hydrates Chemical class 0.000 claims description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 239000008363 phosphate buffer Substances 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 101100495913 Arabidopsis thaliana CHR17 gene Proteins 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 229960004543 anhydrous citric acid Drugs 0.000 claims description 7
- 239000007979 citrate buffer Substances 0.000 claims description 7
- 102200033028 rs587777512 Human genes 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 229940075564 anhydrous dibasic sodium phosphate Drugs 0.000 claims description 6
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- 229960000999 sodium citrate dihydrate Drugs 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 3
- PLICJOZBQFYDQQ-UHFFFAOYSA-N C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.P(=O)(O)(O)O Chemical compound C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.P(=O)(O)(O)O PLICJOZBQFYDQQ-UHFFFAOYSA-N 0.000 claims 2
- 229940061607 dibasic sodium phosphate Drugs 0.000 claims 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims 1
- 239000001509 sodium citrate Substances 0.000 claims 1
- 229960001790 sodium citrate Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 143
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- 239000003814 drug Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 12
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- 231100000252 nontoxic Toxicity 0.000 description 9
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- 229940100692 oral suspension Drugs 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
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- 238000002474 experimental method Methods 0.000 description 8
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- HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
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- 238000011160 research Methods 0.000 description 7
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- 238000003860 storage Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
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- 235000011187 glycerol Nutrition 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
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- 231100000041 toxicology testing Toxicity 0.000 description 6
- 239000008215 water for injection Substances 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
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- QXRSDHAAWVKZLJ-OXZHEXMSSA-N Epothilone B Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C QXRSDHAAWVKZLJ-OXZHEXMSSA-N 0.000 description 3
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| PCT/US2002/002518 WO2002058701A1 (en) | 2001-01-25 | 2002-01-25 | Pharmaceutical dosage forms of epothilones for oral administration |
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| HR20030674A HRP20030674A2 (en) | 2001-01-25 | 2003-08-25 | Pharmaceutical dosage forms of epothilones for oral administration |
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| CA2273083C (en) * | 1996-12-03 | 2012-09-18 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
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| US20050043376A1 (en) * | 1996-12-03 | 2005-02-24 | Danishefsky Samuel J. | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| US6780620B1 (en) * | 1998-12-23 | 2004-08-24 | Bristol-Myers Squibb Company | Microbial transformation method for the preparation of an epothilone |
| US6824879B2 (en) | 1999-06-10 | 2004-11-30 | Honeywell International Inc. | Spin-on-glass anti-reflective coatings for photolithography |
| CA2374944A1 (en) | 1999-06-10 | 2000-12-21 | Nigel Hacker | Spin-on-glass anti-reflective coatings for photolithography |
| US8618085B2 (en) * | 2000-04-28 | 2013-12-31 | Koasn Biosciences Incorporated | Therapeutic formulations of desoxyepothilones |
| WO2002058699A1 (en) | 2001-01-25 | 2002-08-01 | Bristol-Myers Squibb Company | Pharmaceutical forms of epothilones for oral administration |
| RU2003126171A (ru) * | 2001-01-25 | 2005-02-27 | Бристол-Маерс Сквибб Компани (Us) | Парентеральный состав, содержащий аналоги эпотилона |
| MXPA03007394A (es) | 2001-02-20 | 2003-12-04 | Bristol Myers Squibb Co | Tratamiento de tumores refractarios mediante uso de derivados de epotilona. |
| EP1383490B1 (en) * | 2001-03-14 | 2012-04-25 | Bristol-Myers Squibb Company | Combination of an epothilone analog and chemotherapeutic agents for the treatment of proliferative diseases |
| WO2003044600A1 (en) | 2001-11-15 | 2003-05-30 | Honeywell International Inc. | Spin-on anti-reflective coatings for photolithography |
| AU2003218107A1 (en) * | 2002-03-12 | 2003-09-29 | Bristol-Myers Squibb Company | C12-cyano epothilone derivatives |
| TW200403994A (en) * | 2002-04-04 | 2004-03-16 | Bristol Myers Squibb Co | Oral administration of EPOTHILONES |
| TW200400191A (en) * | 2002-05-15 | 2004-01-01 | Bristol Myers Squibb Co | Pharmaceutical compositions and methods of using C-21 modified epothilone derivatives |
| ATE350383T1 (de) | 2002-08-23 | 2007-01-15 | Sloan Kettering Inst Cancer | Synthese von epothilonen, zwischenprodukte dafür, analoga und deren verwendungen |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US7649006B2 (en) | 2002-08-23 | 2010-01-19 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| EP1551425A4 (en) * | 2002-10-09 | 2006-09-20 | Kosan Biosciences Inc | THERAPEUTIC FORMULATIONS |
| US7390503B1 (en) | 2003-08-22 | 2008-06-24 | Barr Laboratories, Inc. | Ondansetron orally disintegrating tablets |
| SI2172205T1 (sl) * | 2003-08-26 | 2014-10-30 | Shire Biopharmaceuticals Holdings Ireland Limited | Farmacevtska formulacija obsegajoča lantanove spojine |
| US20050171167A1 (en) * | 2003-11-04 | 2005-08-04 | Haby Thomas A. | Process and formulation containing epothilones and analogs thereof |
| ES2393674T3 (es) * | 2003-11-14 | 2012-12-27 | Brigham And Women's Hospital, Inc. | Métodos para modular la inmunidad |
| US8053159B2 (en) | 2003-11-18 | 2011-11-08 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
| US20090004277A1 (en) * | 2004-05-18 | 2009-01-01 | Franchini Miriam K | Nanoparticle dispersion containing lactam compound |
| US7244765B2 (en) * | 2004-06-25 | 2007-07-17 | Cytokine Pharmasciences, Inc | Guanylhydrazone salts, compositions, processes of making and methods of using |
| US20060069136A1 (en) * | 2004-09-24 | 2006-03-30 | Ulrich Klar | Use of Epothilones in the treatment of bone metastasis |
| KR20070084325A (ko) * | 2004-11-18 | 2007-08-24 | 브리스톨-마이어스 스큅 컴퍼니 | 익사베필론을 포함하는 장용성 코팅된 비드 및 그의 제조방법 |
| EP1824458A1 (en) * | 2004-11-18 | 2007-08-29 | Bristol-Myers Squibb Company | Enteric coated bead comprising epothilone or an epothilone analog, and preparation and administration thereof |
| AR057325A1 (es) * | 2005-05-25 | 2007-11-28 | Progenics Pharm Inc | Sintesis de (s)-n-metilnaltrexona, composiciones farmaceuticas y usos |
| US8158152B2 (en) * | 2005-11-18 | 2012-04-17 | Scidose Llc | Lyophilization process and products obtained thereby |
| US8642246B2 (en) | 2007-02-26 | 2014-02-04 | Honeywell International Inc. | Compositions, coatings and films for tri-layer patterning applications and methods of preparation thereof |
| BRPI0911482A2 (pt) | 2008-04-24 | 2017-08-29 | Bristol Myers Squibb Co | Uso de epotilona d no tratamento de doenças associadas a tau incluindo doenças de alzheimer |
| US8557877B2 (en) | 2009-06-10 | 2013-10-15 | Honeywell International Inc. | Anti-reflective coatings for optically transparent substrates |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| US8864898B2 (en) | 2011-05-31 | 2014-10-21 | Honeywell International Inc. | Coating formulations for optical elements |
| CN102276433B (zh) * | 2011-06-30 | 2016-04-20 | 南昌大学 | 木豆素c及其衍生物及其在制备抗癌药物中的应用 |
| WO2016167892A1 (en) | 2015-04-13 | 2016-10-20 | Honeywell International Inc. | Polysiloxane formulations and coatings for optoelectronic applications |
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| DE4138042C2 (de) | 1991-11-19 | 1993-10-14 | Biotechnolog Forschung Gmbh | Epothilone, deren Herstellungsverfahren sowie diese Verbindungen enthaltende Mittel |
| DE19542986A1 (de) | 1995-11-17 | 1997-05-22 | Biotechnolog Forschung Gmbh | Epothilon-Derivate und deren Verwendung |
| PT1186606E (pt) | 1995-11-17 | 2004-08-31 | Biotechnolog Forschung Mbh Gbf | Derivados do epotilone sua preparacao e utilizacao |
| DE19639456A1 (de) | 1996-09-25 | 1998-03-26 | Biotechnolog Forschung Gmbh | Epothilon-Derivate, Herstellung und Mittel |
| AU735900B2 (en) * | 1996-03-12 | 2001-07-19 | Pg-Txl Company, L.P. | Water soluble paclitaxel prodrugs |
| US6441025B2 (en) * | 1996-03-12 | 2002-08-27 | Pg-Txl Company, L.P. | Water soluble paclitaxel derivatives |
| NZ334821A (en) | 1996-08-30 | 2000-12-22 | Novartis Ag | Method for producing epothilones |
| DE19645361A1 (de) | 1996-08-30 | 1998-04-30 | Ciba Geigy Ag | Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B, Teil II |
| DE19645362A1 (de) | 1996-10-28 | 1998-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von Epothilon A und B und Derivaten |
| DE19636343C1 (de) * | 1996-08-30 | 1997-10-23 | Schering Ag | Zwischenprodukte innerhalb der Totalsynthese von Epothilon A und B |
| DK1367057T3 (da) | 1996-11-18 | 2009-01-19 | Biotechnolog Forschung Gmbh | Epothiloner E og F |
| US6515016B2 (en) | 1996-12-02 | 2003-02-04 | Angiotech Pharmaceuticals, Inc. | Composition and methods of paclitaxel for treating psoriasis |
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| US6204388B1 (en) | 1996-12-03 | 2001-03-20 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
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| DE19821954A1 (de) | 1997-05-15 | 1998-11-19 | Biotechnolog Forschung Gmbh | Verfahren zur Herstellung eines Epothilon-Derivats |
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| US6211412B1 (en) | 1999-03-29 | 2001-04-03 | The University Of Kansas | Synthesis of epothilones |
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-
2002
- 2002-01-22 WO PCT/US2002/001693 patent/WO2002058699A1/en not_active Application Discontinuation
- 2002-01-22 NZ NZ526871A patent/NZ526871A/en unknown
- 2002-01-25 UY UY27138A patent/UY27138A1/es not_active Application Discontinuation
- 2002-01-25 AR ARP020100288A patent/AR035078A1/es unknown
- 2002-01-25 SK SK921-2003A patent/SK9212003A3/sk unknown
- 2002-01-25 BR BR0206695-5A patent/BR0206695A/pt not_active IP Right Cessation
- 2002-01-25 IL IL15675902A patent/IL156759A0/xx unknown
- 2002-01-25 PL PL02368636A patent/PL368636A1/xx not_active Application Discontinuation
- 2002-01-25 RU RU2003126174/15A patent/RU2291695C2/ru not_active IP Right Cessation
- 2002-01-25 JP JP2002559035A patent/JP2004528287A/ja not_active Withdrawn
- 2002-01-25 TW TW091101287A patent/TWI250017B/zh not_active IP Right Cessation
- 2002-01-25 EP EP02723073A patent/EP1361877A1/en not_active Withdrawn
- 2002-01-25 HU HU0303800A patent/HUP0303800A3/hu unknown
- 2002-01-25 US US10/057,390 patent/US6576651B2/en not_active Ceased
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- 2002-01-25 WO PCT/US2002/002518 patent/WO2002058701A1/en not_active Application Discontinuation
- 2002-01-25 KR KR10-2003-7009781A patent/KR20040025888A/ko not_active Application Discontinuation
- 2002-01-25 CA CA002434584A patent/CA2434584A1/en not_active Abandoned
- 2002-01-25 EE EEP200300329A patent/EE200300329A/xx unknown
- 2002-01-25 CZ CZ20032023A patent/CZ20032023A3/cs unknown
- 2002-01-25 YU YU58103A patent/YU58103A/sh unknown
- 2002-01-25 CN CNB028069927A patent/CN1268336C/zh not_active Expired - Fee Related
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2003
- 2003-07-24 BG BG108027A patent/BG108027A/bg unknown
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- 2003-07-24 NO NO20033343A patent/NO20033343L/no not_active Application Discontinuation
- 2003-08-25 HR HR20030674A patent/HRP20030674A2/hr not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| BR0206695A (pt) | 2004-04-20 |
| HUP0303800A3 (en) | 2005-02-28 |
| EP1361877A1 (en) | 2003-11-19 |
| YU58103A (sh) | 2006-03-03 |
| UY27138A1 (es) | 2002-08-30 |
| HUP0303800A2 (hu) | 2004-03-29 |
| TWI250017B (en) | 2006-03-01 |
| NO20033343D0 (no) | 2003-07-24 |
| IS6892A (is) | 2003-07-24 |
| CA2434584A1 (en) | 2002-08-01 |
| US6576651B2 (en) | 2003-06-10 |
| MXPA03006476A (es) | 2003-09-22 |
| AR035078A1 (es) | 2004-04-14 |
| WO2002058701A1 (en) | 2002-08-01 |
| RU2003126174A (ru) | 2005-02-27 |
| NZ526871A (en) | 2006-01-27 |
| PL368636A1 (en) | 2005-04-04 |
| US20020177615A1 (en) | 2002-11-28 |
| PE20020853A1 (es) | 2002-09-27 |
| JP2004528287A (ja) | 2004-09-16 |
| EE200300329A (et) | 2003-10-15 |
| CN1498106A (zh) | 2004-05-19 |
| SK9212003A3 (en) | 2004-11-03 |
| NO20033343L (no) | 2003-09-24 |
| KR20040025888A (ko) | 2004-03-26 |
| AU2002253880B2 (en) | 2006-11-09 |
| USRE40387E1 (en) | 2008-06-17 |
| RU2291695C2 (ru) | 2007-01-20 |
| CN1268336C (zh) | 2006-08-09 |
| IL156759A0 (en) | 2004-02-08 |
| BG108027A (bg) | 2004-12-30 |
| CZ20032023A3 (cs) | 2005-03-16 |
| WO2002058699A1 (en) | 2002-08-01 |
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