CA2606552A1 - Crystalline forms of tiotropium bromide - Google Patents
Crystalline forms of tiotropium bromide Download PDFInfo
- Publication number
- CA2606552A1 CA2606552A1 CA002606552A CA2606552A CA2606552A1 CA 2606552 A1 CA2606552 A1 CA 2606552A1 CA 002606552 A CA002606552 A CA 002606552A CA 2606552 A CA2606552 A CA 2606552A CA 2606552 A1 CA2606552 A1 CA 2606552A1
- Authority
- CA
- Canada
- Prior art keywords
- crystalline
- tiotropium bromide
- ang
- solvate
- ray powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 title claims abstract description 221
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- 238000010586 diagram Methods 0.000 claims description 62
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- MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical compound O.[Br-].C[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 MQLXPRBEAHBZTK-SEINRUQRSA-M 0.000 claims description 32
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- 235000004279 alanine Nutrition 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
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- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 229960003589 arginine hydrochloride Drugs 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- NFCRBQADEGXVDL-UHFFFAOYSA-M cetylpyridinium chloride monohydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NFCRBQADEGXVDL-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
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- 230000008025 crystallization Effects 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940068939 glyceryl monolaurate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 229960002160 maltose Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 238000010899 nucleation Methods 0.000 description 1
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- 239000005017 polysaccharide Substances 0.000 description 1
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- 238000010926 purge Methods 0.000 description 1
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- 238000010079 rubber tapping Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- 229960004793 sucrose Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 229940074410 trehalose Drugs 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67676005P | 2005-05-02 | 2005-05-02 | |
| US60/676,760 | 2005-05-02 | ||
| PCT/EP2006/061765 WO2006117300A2 (en) | 2005-05-02 | 2006-04-21 | Crystalline forms of tiotropium bromide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2606552A1 true CA2606552A1 (en) | 2006-11-09 |
Family
ID=36617384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002606552A Abandoned CA2606552A1 (en) | 2005-05-02 | 2006-04-21 | Crystalline forms of tiotropium bromide |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20060246009A1 (https=) |
| EP (1) | EP1879888A2 (https=) |
| JP (1) | JP2008540367A (https=) |
| KR (1) | KR20080007656A (https=) |
| CN (1) | CN101203513A (https=) |
| AU (1) | AU2006243239A1 (https=) |
| BR (1) | BRPI0611091A2 (https=) |
| CA (1) | CA2606552A1 (https=) |
| IL (1) | IL187054A0 (https=) |
| MX (1) | MX2007013691A (https=) |
| RU (1) | RU2007144531A (https=) |
| WO (1) | WO2006117300A2 (https=) |
| ZA (1) | ZA200708175B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1966196A2 (en) * | 2005-12-19 | 2008-09-10 | Sicor, Inc. | Pure and stable tiotropium bromide |
| US20070167480A1 (en) * | 2005-12-19 | 2007-07-19 | Sicor Inc. | Pure and stable tiotropium bromide |
| RS52663B2 (sr) * | 2005-12-19 | 2018-05-31 | Sicor Inc | Nova kristalna forma tiotropijum bromida i proces njene pripreme |
| US9108962B2 (en) | 2005-12-19 | 2015-08-18 | Sicor, Inc. | Forms of tiotropium bromide and processes for preparation thereof |
| CN100999521B (zh) * | 2006-01-13 | 2010-12-08 | 江苏正大天晴药业股份有限公司 | 结晶性抗胆碱药噻托溴铵 |
| US20080051582A1 (en) | 2006-07-10 | 2008-02-28 | Sicor Inc. | Process for the preparation of tiotropium bromide |
| EP1923393A1 (en) * | 2006-11-17 | 2008-05-21 | Boehringer Ingelheim Pharma GmbH & Co. KG | Crystalline form of tiotropium bromide and urea |
| GB0716026D0 (en) * | 2007-08-16 | 2007-09-26 | Norton Healthcare Ltd | An inhalable medicament |
| EP2403851B1 (en) | 2009-03-06 | 2015-06-17 | Mahmut Bilgic | New crystalline forms of tiotropium bromide |
| NZ597920A (en) | 2009-08-07 | 2014-05-30 | Generics Uk Ltd | Anhydrate of tiotropium bromide |
| WO2011015883A1 (en) | 2009-08-07 | 2011-02-10 | Generics [Uk] Limited | Dichloromethane solvate of tiotropium bromide and its use |
| TR201007108A2 (tr) * | 2010-08-25 | 2012-03-21 | B�Lg�� Mahmut | Yeni tiotropyum bromür kristali ve üretim yöntemi.@ |
| TR201101897A2 (tr) * | 2011-02-28 | 2012-09-21 | Bi̇lgi̇ç Mahmut | Tiotropyum bromür içeren kristal madde |
| CZ304368B6 (cs) * | 2011-11-28 | 2014-04-02 | Zentiva, K.S. | Směsný solvát tiotropium bromidu a způsob jeho přípravy |
| CN103130798B (zh) * | 2011-11-30 | 2015-12-02 | 连云港润众制药有限公司 | 噻托溴铵的结晶 |
| GB201200525D0 (en) | 2011-12-19 | 2012-02-29 | Teva Branded Pharmaceutical Prod R & D Inc | An inhalable medicament |
| PT106142B (pt) | 2012-02-10 | 2014-07-18 | Hovione Farmaci Ncia S A | Processo para a preparação de brometo de tiotrópio |
| EP2897955B1 (en) * | 2012-09-11 | 2019-11-06 | Bilgic, Mahmut | New tiotropium bromide crystalline form |
| UA115888C2 (uk) * | 2012-11-05 | 2018-01-10 | Зентіва, К.С. | Стабілізація сольватів тіотропію |
| EP2789611A1 (en) * | 2013-04-08 | 2014-10-15 | Cerbios-Pharma S.A. | A crystalline form of tiotropium bromide |
| CN104341413A (zh) * | 2013-07-29 | 2015-02-11 | 天津金耀集团有限公司 | 一种无水噻托溴铵的新晶型 |
| CN104341412A (zh) * | 2013-07-29 | 2015-02-11 | 天津金耀集团有限公司 | 一种无水噻托溴铵结晶的制备方法 |
| EP2913332A1 (en) | 2014-02-27 | 2015-09-02 | Euticals S.P.A. | Crystalline form of tiotropium bromide with lactose |
| US10034866B2 (en) | 2014-06-19 | 2018-07-31 | Teva Branded Pharmaceutical Products R&D, Inc. | Inhalable medicament comprising tiotropium |
| WO2017138896A1 (en) | 2016-02-11 | 2017-08-17 | Sima Patent Ve Lisanslama Hizmetleri Ltd. Şti | Crystalline form of tiotropium bromide anhydrate |
| PT115583B (pt) * | 2019-06-17 | 2022-05-02 | Hovione Farm S A | Processo contínuo para a preparação de medicamentos anticolinérgicos |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931041C2 (de) * | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| CN100519558C (zh) * | 2000-10-12 | 2009-07-29 | 贝林格尔英格海姆法玛两合公司 | 结晶单水合物、其制备方法及其在制备药物组合中的用途 |
| DE10064816A1 (de) * | 2000-12-22 | 2002-06-27 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung eines Anticholinergikums |
| US6608055B2 (en) * | 2001-06-22 | 2003-08-19 | Boehringer Ingelheim Pharma Kg | Crystalline anticholinergic, processes for preparing it and its use for preparing a pharmaceutical composition |
| CZ302786B6 (cs) * | 2001-06-22 | 2011-11-09 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Krystalický bezvodý tiotropiumbromid, zpusob jeho výroby a jeho použití pro výrobu léciva pro lécbu asthmatu |
| DE10212264A1 (de) * | 2002-03-20 | 2003-10-02 | Boehringer Ingelheim Pharma | Kristallines Mikronisat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung eines Arzneimittels |
| US7244415B2 (en) * | 2002-03-28 | 2007-07-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | HFA suspension formulations of an anhydrate |
| DE10214264A1 (de) * | 2002-03-28 | 2003-10-16 | Boehringer Ingelheim Pharma | HFA-Suspensionsformulierungen eines Anhydrats |
| MXPA05006383A (es) * | 2002-12-16 | 2005-08-29 | Boehringer Ingelheim Pharma | Formulaciones de soluciones de hidrofluorocarburo que contienen tiotropio. |
| ES2338563T3 (es) * | 2003-11-03 | 2010-05-10 | Boehringer Ingelheim International Gmbh | Nuevo anhidrato cristalino con efecto anticolinergico. |
-
2006
- 2006-04-21 JP JP2008509409A patent/JP2008540367A/ja active Pending
- 2006-04-21 MX MX2007013691A patent/MX2007013691A/es not_active Application Discontinuation
- 2006-04-21 CA CA002606552A patent/CA2606552A1/en not_active Abandoned
- 2006-04-21 KR KR1020077028066A patent/KR20080007656A/ko not_active Withdrawn
- 2006-04-21 EP EP06763053A patent/EP1879888A2/en not_active Withdrawn
- 2006-04-21 RU RU2007144531/04A patent/RU2007144531A/ru not_active Application Discontinuation
- 2006-04-21 CN CNA2006800139215A patent/CN101203513A/zh active Pending
- 2006-04-21 BR BRPI0611091-6A patent/BRPI0611091A2/pt not_active IP Right Cessation
- 2006-04-21 WO PCT/EP2006/061765 patent/WO2006117300A2/en not_active Ceased
- 2006-04-21 AU AU2006243239A patent/AU2006243239A1/en not_active Abandoned
- 2006-05-01 US US11/381,079 patent/US20060246009A1/en not_active Abandoned
-
2007
- 2007-09-25 ZA ZA200708175A patent/ZA200708175B/xx unknown
- 2007-10-31 IL IL187054A patent/IL187054A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1879888A2 (en) | 2008-01-23 |
| WO2006117300A3 (en) | 2007-04-26 |
| KR20080007656A (ko) | 2008-01-22 |
| WO2006117300A2 (en) | 2006-11-09 |
| JP2008540367A (ja) | 2008-11-20 |
| IL187054A0 (en) | 2008-02-09 |
| ZA200708175B (en) | 2008-09-25 |
| RU2007144531A (ru) | 2009-06-10 |
| BRPI0611091A2 (pt) | 2010-08-03 |
| US20060246009A1 (en) | 2006-11-02 |
| CN101203513A (zh) | 2008-06-18 |
| AU2006243239A1 (en) | 2006-11-09 |
| MX2007013691A (es) | 2008-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |