ZA200204858B - Process for the preparation of sodium salts of statins. - Google Patents
Process for the preparation of sodium salts of statins. Download PDFInfo
- Publication number
- ZA200204858B ZA200204858B ZA200204858A ZA200204858A ZA200204858B ZA 200204858 B ZA200204858 B ZA 200204858B ZA 200204858 A ZA200204858 A ZA 200204858A ZA 200204858 A ZA200204858 A ZA 200204858A ZA 200204858 B ZA200204858 B ZA 200204858B
- Authority
- ZA
- South Africa
- Prior art keywords
- statins
- solvent
- sodium
- sodium salts
- ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 title claims description 21
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 title claims description 21
- 159000000000 sodium salts Chemical class 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 150000001261 hydroxy acids Chemical group 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002596 lactones Chemical group 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims description 6
- 239000012296 anti-solvent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims 1
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 12
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 12
- VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 description 11
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 10
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 9
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 8
- 229960004844 lovastatin Drugs 0.000 description 8
- 229960002965 pravastatin Drugs 0.000 description 8
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 241000894007 species Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PDBXRGUGLTUAAD-ABPOPGQRSA-M sodium;(3r)-7-[(1s,2s,8s,8ar)-2-methyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3-hydroxyheptanoate Chemical class [Na+].C1=C[C@H](C)[C@H](CCCC[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)CCC=C21 PDBXRGUGLTUAAD-ABPOPGQRSA-M 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 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 1
- 241000228143 Penicillium Species 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 229950009116 mevastatin Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- LXZBFUBRYYVRQJ-AXHZAXLDSA-M sodium;(3r,5r)-7-[(1s,2s,6r,8s,8ar)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C=C21 LXZBFUBRYYVRQJ-AXHZAXLDSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1546DE1999 IN191580B (xx) | 1999-12-17 | 1999-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200204858B true ZA200204858B (en) | 2004-02-04 |
Family
ID=11092726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200204858A ZA200204858B (en) | 1999-12-17 | 2002-06-18 | Process for the preparation of sodium salts of statins. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6756507B2 (xx) |
| EP (1) | EP1265841A4 (xx) |
| JP (1) | JP2004510689A (xx) |
| AU (1) | AU777962B2 (xx) |
| BG (1) | BG106918A (xx) |
| BR (1) | BR0016400A (xx) |
| CA (1) | CA2394464A1 (xx) |
| CZ (1) | CZ20022271A3 (xx) |
| HU (1) | HUP0301771A2 (xx) |
| IL (1) | IL150245A0 (xx) |
| IN (1) | IN191580B (xx) |
| MX (1) | MXPA02005893A (xx) |
| NZ (1) | NZ519434A (xx) |
| PL (1) | PL364462A1 (xx) |
| RU (1) | RU2246481C2 (xx) |
| SK (1) | SK9572002A3 (xx) |
| UA (1) | UA72572C2 (xx) |
| WO (1) | WO2001044144A2 (xx) |
| ZA (1) | ZA200204858B (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP9902352A1 (hu) * | 1999-07-12 | 2000-09-28 | Gyógyszerkutató Intézet Kft. | Eljárás pravasztatin mikrobiológiai előállítására |
| NL1017548C2 (nl) * | 2001-03-09 | 2002-09-10 | Synthon Bv | Een lactonisatie proces. |
| AU2003269476A1 (en) * | 2003-08-26 | 2005-03-10 | Biocon Limited | Process for the preparation of 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-((2s)-2-methyl-1-oxobutoxy)-, (beta r,delta r,1s,2s,6s,8s,8ar)-1-naphthaleneheptanoic acid, sodium salt. |
| DE602004017784D1 (de) * | 2004-03-30 | 2008-12-24 | Lupin Ltd | Verbessertes verfahren zur herstellung von 4-hydroxypyran-2-onderivaten |
| RU2585233C2 (ru) * | 2013-12-27 | 2016-05-27 | Открытое акционерное общество "Красфарма" | Промышленный способ получения компактина |
| CN114031496A (zh) * | 2021-11-30 | 2022-02-11 | 广东蓝宝制药有限公司 | 一种高纯度普伐他汀1,1,3,3-四甲基丁胺的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK149080C (da) * | 1980-06-06 | 1986-07-28 | Sankyo Co | Fremgangsmaade til fremstilling af derivater af ml-236b-carboxylsyre |
| US4432996A (en) * | 1980-11-17 | 1984-02-21 | Merck & Co., Inc. | Hypocholesterolemic fermentation products and process of preparation |
| JPS5815968A (ja) * | 1981-07-21 | 1983-01-29 | Sankyo Co Ltd | Ｍｌ−２３６ｂ誘導体およびその製法 |
| IT1255716B (it) * | 1992-10-05 | 1995-11-10 | Procedimento per la preparazione di antibiotici beta-lattamici sterili | |
| IT1292132B1 (it) * | 1997-06-11 | 1999-01-25 | Synteco S R L | Procedimento per la preparazione di diacereina |
| NZ503982A (en) * | 1997-12-12 | 2002-03-28 | Warner Lambert Co | Statin-carboxyalkylether combinations useful for treating vascular disorders and diabetes mellitus |
-
1999
- 1999-12-17 IN IN1546DE1999 patent/IN191580B/en unknown
-
2000
- 2000-12-14 US US10/149,625 patent/US6756507B2/en not_active Expired - Fee Related
- 2000-12-14 WO PCT/IB2000/001873 patent/WO2001044144A2/en not_active Application Discontinuation
- 2000-12-14 BR BR0016400-3A patent/BR0016400A/pt not_active IP Right Cessation
- 2000-12-14 NZ NZ519434A patent/NZ519434A/en unknown
- 2000-12-14 PL PL00364462A patent/PL364462A1/xx not_active Application Discontinuation
- 2000-12-14 EP EP00981529A patent/EP1265841A4/en not_active Withdrawn
- 2000-12-14 AU AU18762/01A patent/AU777962B2/en not_active Ceased
- 2000-12-14 CZ CZ20022271A patent/CZ20022271A3/cs unknown
- 2000-12-14 HU HU0301771A patent/HUP0301771A2/hu unknown
- 2000-12-14 MX MXPA02005893A patent/MXPA02005893A/es active IP Right Grant
- 2000-12-14 RU RU2002119211/04A patent/RU2246481C2/ru not_active IP Right Cessation
- 2000-12-14 CA CA002394464A patent/CA2394464A1/en not_active Abandoned
- 2000-12-14 IL IL15024500A patent/IL150245A0/xx unknown
- 2000-12-14 SK SK957-2002A patent/SK9572002A3/sk unknown
- 2000-12-14 UA UA2002075856A patent/UA72572C2/uk unknown
- 2000-12-14 JP JP2001545234A patent/JP2004510689A/ja active Pending
-
2002
- 2002-06-18 ZA ZA200204858A patent/ZA200204858B/en unknown
- 2002-07-12 BG BG106918A patent/BG106918A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG106918A (en) | 2003-04-30 |
| EP1265841A4 (en) | 2007-09-05 |
| IN191580B (xx) | 2003-12-06 |
| HUP0301771A2 (hu) | 2003-09-29 |
| BR0016400A (pt) | 2003-12-30 |
| WO2001044144A3 (en) | 2001-11-15 |
| WO2001044144A2 (en) | 2001-06-21 |
| US6756507B2 (en) | 2004-06-29 |
| NZ519434A (en) | 2003-10-31 |
| RU2002119211A (ru) | 2004-01-10 |
| US20030050502A1 (en) | 2003-03-13 |
| RU2246481C2 (ru) | 2005-02-20 |
| EP1265841A2 (en) | 2002-12-18 |
| CA2394464A1 (en) | 2001-06-21 |
| UA72572C2 (en) | 2005-03-15 |
| MXPA02005893A (es) | 2003-02-27 |
| AU777962B2 (en) | 2004-11-04 |
| JP2004510689A (ja) | 2004-04-08 |
| IL150245A0 (en) | 2002-12-01 |
| AU1876201A (en) | 2001-06-25 |
| PL364462A1 (en) | 2004-12-13 |
| SK9572002A3 (en) | 2002-12-03 |
| CZ20022271A3 (cs) | 2002-11-13 |
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