BG107357A - Тиазолидиндионова сол за лечение hа захарен диабеt - Google Patents
Тиазолидиндионова сол за лечение hа захарен диабеt Download PDFInfo
- Publication number
- BG107357A BG107357A BG107357A BG10735702A BG107357A BG 107357 A BG107357 A BG 107357A BG 107357 A BG107357 A BG 107357A BG 10735702 A BG10735702 A BG 10735702A BG 107357 A BG107357 A BG 107357A
- Authority
- BG
- Bulgaria
- Prior art keywords
- hydrobromide
- solvate
- compound
- benzyl
- thiazolidine
- Prior art date
Links
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 37
- 238000011282 treatment Methods 0.000 title claims description 22
- 150000001467 thiazolidinediones Chemical class 0.000 title claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 112
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000012453 solvate Substances 0.000 claims abstract description 57
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 29
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 22
- KIVBYLUEMHJKKS-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione hydrobromide Chemical compound Br.O=C1CSC(=O)N1 KIVBYLUEMHJKKS-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002844 melting Methods 0.000 claims description 15
- 230000008018 melting Effects 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 14
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 12
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 238000011321 prophylaxis Methods 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- -1 N- (2-pyridyl) amino Chemical group 0.000 claims description 8
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 8
- 229940088679 drug related substance Drugs 0.000 claims description 8
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 8
- 238000002329 infrared spectrum Methods 0.000 claims description 8
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- 239000000463 material Substances 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
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- 239000003981 vehicle Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 206010022489 Insulin Resistance Diseases 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 238000001237 Raman spectrum Methods 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 6
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- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 5
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
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- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 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 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 2
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- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
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- 206010065673 Nephritic syndrome Diseases 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
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- 229920002472 Starch Polymers 0.000 claims description 2
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- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000008168 almond oil Substances 0.000 claims description 2
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims description 2
- 229940063655 aluminum stearate Drugs 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003708 ampul Substances 0.000 claims description 2
- 230000003444 anaesthetic effect Effects 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims description 2
- 239000006172 buffering agent Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
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- 238000011161 development Methods 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims description 2
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- 230000001079 digestive effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
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- 235000019634 flavors Nutrition 0.000 claims description 2
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- 150000008282 halocarbons Chemical class 0.000 claims description 2
- GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical class O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 claims description 2
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- 201000001421 hyperglycemia Diseases 0.000 claims description 2
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- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
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- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 235000010603 pastilles Nutrition 0.000 claims description 2
- 239000011049 pearl Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 230000003893 regulation of appetite Effects 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
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- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 2
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- 239000008109 sodium starch glycolate Substances 0.000 claims description 2
- 229940079832 sodium starch glycolate Drugs 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 235000010199 sorbic acid Nutrition 0.000 claims description 2
- 239000004334 sorbic acid Substances 0.000 claims description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002076 thermal analysis method Methods 0.000 claims description 2
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- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 238000009827 uniform distribution Methods 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- MSOPDKKENJARPF-UHFFFAOYSA-N 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrobromide Chemical compound Br.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O MSOPDKKENJARPF-UHFFFAOYSA-N 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
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- 229940124597 therapeutic agent Drugs 0.000 claims 1
- OZJSJUKQPIGBBO-UHFFFAOYSA-N n-methyl-n-[2-[4-(1,3-thiazolidin-5-ylmethyl)phenoxy]ethyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1CNCS1 OZJSJUKQPIGBBO-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0014006.1A GB0014006D0 (en) | 2000-06-08 | 2000-06-08 | Novel pharmaceutical |
| PCT/GB2001/002567 WO2001094344A1 (en) | 2000-06-08 | 2001-06-08 | Thiazolidinedione salt for treatment of diabetes mellitus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG107357A true BG107357A (bg) | 2003-08-29 |
Family
ID=9893257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG107357A BG107357A (bg) | 2000-06-08 | 2002-12-05 | Тиазолидиндионова сол за лечение hа захарен диабеt |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP1296980A1 (cs) |
| JP (1) | JP2003535862A (cs) |
| KR (1) | KR20030007918A (cs) |
| CN (1) | CN1443186A (cs) |
| AP (1) | AP2002002673A0 (cs) |
| AU (1) | AU2001264078A1 (cs) |
| BG (1) | BG107357A (cs) |
| BR (1) | BR0111536A (cs) |
| CA (1) | CA2411065A1 (cs) |
| CZ (1) | CZ20023966A3 (cs) |
| DZ (1) | DZ3382A1 (cs) |
| EA (1) | EA200300005A1 (cs) |
| GB (1) | GB0014006D0 (cs) |
| HU (1) | HUP0301137A3 (cs) |
| IL (1) | IL153279A0 (cs) |
| MA (1) | MA25753A1 (cs) |
| MX (1) | MXPA02012100A (cs) |
| NO (1) | NO20025883L (cs) |
| OA (1) | OA12284A (cs) |
| PL (1) | PL360592A1 (cs) |
| SK (1) | SK17142002A3 (cs) |
| WO (1) | WO2001094344A1 (cs) |
| ZA (1) | ZA200209954B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE39384E1 (en) | 1993-09-01 | 2006-11-07 | Smithkline Beecham P.L.C. | Substituted thiazolidinedione derivatives |
| DE102005034406A1 (de) * | 2005-07-22 | 2007-02-01 | Ratiopharm Gmbh | Neue Salze von Rosiglitazon |
| EP2016076A2 (en) * | 2007-01-22 | 2009-01-21 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of rosiglitazone hydrobromide and processes for preparation thereof |
| EP1956018A1 (de) * | 2007-02-06 | 2008-08-13 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung eines Benzimidazolderivats |
| WO2010021745A2 (en) * | 2008-08-21 | 2010-02-25 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of rosiglitazone hydrobromide and processes for their preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9218830D0 (en) * | 1992-09-05 | 1992-10-21 | Smithkline Beecham Plc | Novel compounds |
-
2000
- 2000-06-08 GB GBGB0014006.1A patent/GB0014006D0/en not_active Ceased
-
2001
- 2001-06-08 WO PCT/GB2001/002567 patent/WO2001094344A1/en not_active Ceased
- 2001-06-08 BR BR0111536-7A patent/BR0111536A/pt not_active IP Right Cessation
- 2001-06-08 AU AU2001264078A patent/AU2001264078A1/en not_active Abandoned
- 2001-06-08 AP APAP/P/2002/002673A patent/AP2002002673A0/en unknown
- 2001-06-08 MX MXPA02012100A patent/MXPA02012100A/es unknown
- 2001-06-08 CZ CZ20023966A patent/CZ20023966A3/cs unknown
- 2001-06-08 EP EP01938400A patent/EP1296980A1/en not_active Withdrawn
- 2001-06-08 JP JP2002501893A patent/JP2003535862A/ja active Pending
- 2001-06-08 CA CA002411065A patent/CA2411065A1/en not_active Abandoned
- 2001-06-08 CN CN01813190A patent/CN1443186A/zh active Pending
- 2001-06-08 DZ DZ013382A patent/DZ3382A1/xx active
- 2001-06-08 HU HU0301137A patent/HUP0301137A3/hu unknown
- 2001-06-08 EA EA200300005A patent/EA200300005A1/ru unknown
- 2001-06-08 OA OA1200200370A patent/OA12284A/en unknown
- 2001-06-08 IL IL15327901A patent/IL153279A0/xx unknown
- 2001-06-08 KR KR1020027016721A patent/KR20030007918A/ko not_active Withdrawn
- 2001-06-08 PL PL36059201A patent/PL360592A1/xx not_active Application Discontinuation
- 2001-06-08 SK SK1714-2002A patent/SK17142002A3/sk not_active Application Discontinuation
-
2002
- 2002-12-04 MA MA26933A patent/MA25753A1/fr unknown
- 2002-12-05 BG BG107357A patent/BG107357A/bg unknown
- 2002-12-06 NO NO20025883A patent/NO20025883L/no not_active Application Discontinuation
- 2002-12-09 ZA ZA200209954A patent/ZA200209954B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL360592A1 (en) | 2004-09-20 |
| CA2411065A1 (en) | 2001-12-13 |
| CN1443186A (zh) | 2003-09-17 |
| AU2001264078A1 (en) | 2001-12-17 |
| CZ20023966A3 (cs) | 2003-04-16 |
| BR0111536A (pt) | 2003-07-01 |
| JP2003535862A (ja) | 2003-12-02 |
| GB0014006D0 (en) | 2000-08-02 |
| NO20025883D0 (no) | 2002-12-06 |
| EA200300005A1 (ru) | 2003-04-24 |
| DZ3382A1 (fr) | 2001-12-13 |
| MXPA02012100A (es) | 2003-04-25 |
| AP2002002673A0 (en) | 2002-12-31 |
| KR20030007918A (ko) | 2003-01-23 |
| MA25753A1 (fr) | 2003-04-01 |
| ZA200209954B (en) | 2003-10-10 |
| IL153279A0 (en) | 2003-07-06 |
| EP1296980A1 (en) | 2003-04-02 |
| WO2001094344A1 (en) | 2001-12-13 |
| HUP0301137A2 (hu) | 2003-08-28 |
| NO20025883L (no) | 2003-02-03 |
| HUP0301137A3 (en) | 2005-04-28 |
| OA12284A (en) | 2003-11-10 |
| SK17142002A3 (sk) | 2003-10-07 |
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