UA77671C2 - Crystalline form of omeprazole - Google Patents
Crystalline form of omeprazole Download PDFInfo
- Publication number
- UA77671C2 UA77671C2 UA2003109492A UA2003109492A UA77671C2 UA 77671 C2 UA77671 C2 UA 77671C2 UA 2003109492 A UA2003109492 A UA 2003109492A UA 2003109492 A UA2003109492 A UA 2003109492A UA 77671 C2 UA77671 C2 UA 77671C2
- Authority
- UA
- Ukraine
- Prior art keywords
- omeprazole
- strong
- differs
- acetone
- weak
- Prior art date
Links
- 229960000381 omeprazole Drugs 0.000 title claims abstract description 139
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 title claims abstract description 138
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 239000013543 active substance Substances 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 10
- 230000000717 retained effect Effects 0.000 claims description 10
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 8
- 238000002441 X-ray diffraction Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 3
- 239000000945 filler Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 abstract description 12
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 239000012535 impurity Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000001802 infusion Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000007857 degradation product Substances 0.000 description 3
- 238000012430 stability testing Methods 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 230000009858 acid secretion Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 229960003943 hypromellose Drugs 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229940126409 proton pump inhibitor Drugs 0.000 description 2
- 239000000612 proton pump inhibitor Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- -1 their shape Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- 108091006112 ATPases Proteins 0.000 description 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 1
- 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 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000001711 oxyntic cell Anatomy 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001055 reflectance spectroscopy Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200100111A SI20875A (sl) | 2001-04-25 | 2001-04-25 | Kristalna oblika omeprazola |
| PCT/IB2002/001350 WO2002085889A1 (en) | 2001-04-25 | 2002-04-24 | Crystalline form of omeprazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77671C2 true UA77671C2 (en) | 2007-01-15 |
Family
ID=20432882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003109492A UA77671C2 (en) | 2001-04-25 | 2002-04-24 | Crystalline form of omeprazole |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US20040122056A1 (hu) |
| EP (1) | EP1390360B1 (hu) |
| JP (1) | JP4455815B2 (hu) |
| KR (1) | KR20030094358A (hu) |
| CN (1) | CN1531533B (hu) |
| AT (1) | ATE346063T1 (hu) |
| AU (1) | AU2002307892B2 (hu) |
| BG (1) | BG108287A (hu) |
| BR (1) | BR0209103A (hu) |
| CA (1) | CA2445251C (hu) |
| CZ (1) | CZ20032911A3 (hu) |
| DE (1) | DE60216273T2 (hu) |
| HR (1) | HRP20030853B1 (hu) |
| HU (1) | HUP0303928A2 (hu) |
| IL (1) | IL158561A0 (hu) |
| MX (1) | MXPA03009789A (hu) |
| NO (1) | NO20034715L (hu) |
| NZ (1) | NZ528917A (hu) |
| PL (1) | PL366471A1 (hu) |
| RS (1) | RS50880B (hu) |
| RU (1) | RU2286991C2 (hu) |
| SI (2) | SI20875A (hu) |
| SK (1) | SK13192003A3 (hu) |
| UA (1) | UA77671C2 (hu) |
| WO (1) | WO2002085889A1 (hu) |
| ZA (1) | ZA200307988B (hu) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8815916B2 (en) | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| ES2246149B1 (es) * | 2004-07-02 | 2007-06-01 | Esteve Quimica, S.A. | Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion. |
| EP1904064A4 (en) * | 2005-07-07 | 2009-12-02 | Reddys Lab Ltd Dr | OMEPRAZOLE OF FORM B |
| EP1988163B1 (en) * | 2006-02-22 | 2012-06-27 | International Institute of Cancer Immunology, Inc. | Hla-a*3303-restricted wt1 peptide and pharmaceutical composition comprising the same |
| WO2008067037A2 (en) | 2006-10-05 | 2008-06-05 | Santarus, Inc. | Novel formulations of proton pump inhibitors and methods of using these formulations |
| EP2086543A2 (en) | 2006-10-27 | 2009-08-12 | The Curators of the University of Missouri | Compositions comprising at least one acid labile proton pump inhibiting agents, optionally other pharmaceutically active agents and methods of using same |
| WO2008092939A2 (en) | 2007-01-31 | 2008-08-07 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for the preparation of optically pure omeprazole via salt formation with a chiral amine or treatment with an entiomer converting enzyme and chromatographic separation |
| WO2010134099A1 (en) | 2009-05-21 | 2010-11-25 | Cadila Healthcare Limited | One pot process for preparing omeprazole and related compounds |
| CN102786513A (zh) * | 2011-05-18 | 2012-11-21 | 中国医学科学院药物研究所 | 奥美拉唑晶e型物质及制备方法与在药品和保健品中应用 |
| CN102351846B (zh) * | 2011-09-07 | 2012-08-22 | 周晓东 | 一种新的奥美拉唑钠化合物及其药物组合物 |
| KR101459088B1 (ko) * | 2012-08-02 | 2014-12-02 | 대화제약 주식회사 | 알-라베프라졸, 이의 금속염의 제조방법 |
| WO2023079094A1 (en) * | 2021-11-05 | 2023-05-11 | Cinclus Pharma Holding AB (publ) | Polymorphs of the hydrochloride salt of linaprazan glurate |
| WO2024075017A1 (en) | 2022-10-04 | 2024-04-11 | Zabirnyk Arsenii | Inhibition of aortic valve calcification |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| IE67187B1 (en) * | 1990-06-15 | 1996-03-06 | Merck & Co Inc | A crystallization method to improve crystal structure and size |
| SE510666C2 (sv) * | 1996-12-20 | 1999-06-14 | Astra Ab | Nya Kristallmodifikationer |
| SI20019A (sl) * | 1998-07-13 | 2000-02-29 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Izboljšan postopek sinteze 5-metoksi -2-/(4-metoksi-3,5-dimetil-2-piridil)metil/ sulfinil-1H-benzimidazola |
| US6166213A (en) * | 1998-08-11 | 2000-12-26 | Merck & Co., Inc. | Omeprazole process and compositions thereof |
| UA72748C2 (en) * | 1998-11-10 | 2005-04-15 | Astrazeneca Ab | A novel crystalline form of omeprazole |
| AUPQ841800A0 (en) * | 2000-06-28 | 2000-07-20 | Biomolecular Research Institute Limited | Truncated egf receptor |
| US6627646B2 (en) * | 2001-07-17 | 2003-09-30 | Sepracor Inc. | Norastemizole polymorphs |
-
2001
- 2001-04-25 SI SI200100111A patent/SI20875A/sl not_active IP Right Cessation
-
2002
- 2002-04-24 IL IL15856102A patent/IL158561A0/xx unknown
- 2002-04-24 EP EP02764081A patent/EP1390360B1/en not_active Expired - Lifetime
- 2002-04-24 CN CN028089553A patent/CN1531533B/zh not_active Expired - Lifetime
- 2002-04-24 RU RU2003133213/04A patent/RU2286991C2/ru active
- 2002-04-24 SI SI200230491T patent/SI1390360T1/sl unknown
- 2002-04-24 UA UA2003109492A patent/UA77671C2/uk unknown
- 2002-04-24 AU AU2002307892A patent/AU2002307892B2/en not_active Expired
- 2002-04-24 NZ NZ528917A patent/NZ528917A/en unknown
- 2002-04-24 SK SK1319-2003A patent/SK13192003A3/sk unknown
- 2002-04-24 HU HU0303928A patent/HUP0303928A2/hu unknown
- 2002-04-24 PL PL02366471A patent/PL366471A1/xx not_active Application Discontinuation
- 2002-04-24 US US10/475,239 patent/US20040122056A1/en not_active Abandoned
- 2002-04-24 KR KR10-2003-7013767A patent/KR20030094358A/ko not_active Application Discontinuation
- 2002-04-24 RS YUP-840/03A patent/RS50880B/sr unknown
- 2002-04-24 MX MXPA03009789A patent/MXPA03009789A/es active IP Right Grant
- 2002-04-24 WO PCT/IB2002/001350 patent/WO2002085889A1/en active IP Right Grant
- 2002-04-24 DE DE60216273T patent/DE60216273T2/de not_active Expired - Lifetime
- 2002-04-24 CZ CZ20032911A patent/CZ20032911A3/cs unknown
- 2002-04-24 JP JP2002583416A patent/JP4455815B2/ja not_active Expired - Lifetime
- 2002-04-24 AT AT02764081T patent/ATE346063T1/de active
- 2002-04-24 CA CA2445251A patent/CA2445251C/en not_active Expired - Lifetime
- 2002-04-24 BR BR0209103-8A patent/BR0209103A/pt not_active Application Discontinuation
-
2003
- 2003-10-14 ZA ZA200307988A patent/ZA200307988B/xx unknown
- 2003-10-20 HR HR20030853A patent/HRP20030853B1/xx not_active IP Right Cessation
- 2003-10-21 NO NO20034715A patent/NO20034715L/no not_active Application Discontinuation
- 2003-10-24 BG BG108287A patent/BG108287A/bg unknown
-
2005
- 2005-10-12 US US11/248,461 patent/US7553856B2/en not_active Expired - Lifetime
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