CA2610909A1 - Manufacturing process for tigecycline - Google Patents
Manufacturing process for tigecycline Download PDFInfo
- Publication number
- CA2610909A1 CA2610909A1 CA002610909A CA2610909A CA2610909A1 CA 2610909 A1 CA2610909 A1 CA 2610909A1 CA 002610909 A CA002610909 A CA 002610909A CA 2610909 A CA2610909 A CA 2610909A CA 2610909 A1 CA2610909 A1 CA 2610909A1
- Authority
- CA
- Canada
- Prior art keywords
- tigecycline
- solution
- water
- temperature
- oxygen level
- 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
- 229960004089 tigecycline Drugs 0.000 title claims abstract description 51
- FPZLLRFZJZRHSY-HJYUBDRYSA-N tigecycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O FPZLLRFZJZRHSY-HJYUBDRYSA-N 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 34
- 238000001990 intravenous administration Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 24
- 239000000843 powder Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 11
- 239000008380 degradant Substances 0.000 claims description 10
- 238000010828 elution Methods 0.000 claims description 4
- 238000004007 reversed phase HPLC Methods 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000001802 infusion Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 16
- 230000015556 catabolic process Effects 0.000 description 14
- 238000006731 degradation reaction Methods 0.000 description 14
- 239000008215 water for injection Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 239000008364 bulk solution Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004108 freeze drying Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 4
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
- 229940088679 drug related substance Drugs 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 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 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- IQIPCMYBFDOLBO-IRDJJEOVSA-N (4s,4as,5ar,12ar)-9-amino-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=C(N)C(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O IQIPCMYBFDOLBO-IRDJJEOVSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101000941356 Nostoc ellipsosporum Cyanovirin-N Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229960004023 minocycline Drugs 0.000 description 1
- DYKFCLLONBREIL-KVUCHLLUSA-N minocycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O DYKFCLLONBREIL-KVUCHLLUSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008227 sterile water for injection Substances 0.000 description 1
- -1 t-butylglycyl Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IVFLPPKNEWVNFG-UHFFFAOYSA-N tetracene-1-carboxamide Chemical class C1=CC=C2C=C(C=C3C(C(=O)N)=CC=CC3=C3)C3=CC2=C1 IVFLPPKNEWVNFG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69117305P | 2005-06-16 | 2005-06-16 | |
| US60/691,173 | 2005-06-16 | ||
| PCT/US2006/023613 WO2006138641A2 (en) | 2005-06-16 | 2006-06-16 | Manufacturing process for tigecycline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2610909A1 true CA2610909A1 (en) | 2006-12-28 |
Family
ID=37111782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002610909A Abandoned CA2610909A1 (en) | 2005-06-16 | 2006-06-16 | Manufacturing process for tigecycline |
Country Status (22)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2007713A2 (en) * | 2006-04-17 | 2008-12-31 | Teva Pharmaceutical Industries Ltd | Isolation of tetracycline derivatives |
| DK2016045T3 (en) * | 2006-04-24 | 2015-02-02 | Teva Pharma | TIGECYCLIN CRYSTAL FORM AND PROCEDURES FOR PREPARING IT |
| US8198470B2 (en) * | 2006-04-24 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form II of tigecycline and processes for preparation thereof |
| MX2008009520A (es) * | 2006-11-29 | 2009-02-26 | Teva Pharma | Formas cristalinas de tigeciclina y procesos de preparacion de ellas. |
| US20080234504A1 (en) * | 2006-11-30 | 2008-09-25 | Evgeny Tsiperman | Processes for preparation of 9-haloacetamidominocyclines |
| EP2114865A1 (en) * | 2007-03-01 | 2009-11-11 | Teva Pharmaceutical Industries Ltd. | Processes for purification of tigecycline |
| WO2009052152A2 (en) * | 2007-10-16 | 2009-04-23 | Wyeth | Tigecycline and methods of preparing intermediates |
| US9107929B2 (en) | 2008-05-01 | 2015-08-18 | Ranbaxy Laboratories Limited | Stable parenteral formulations of tigecycline |
| ITMI20080807A1 (it) | 2008-05-05 | 2009-11-06 | Antibioticos Spa | Procedimento per la preparazione di tigeciclina in forma amorfa |
| WO2010017273A2 (en) * | 2008-08-06 | 2010-02-11 | Wyeth | Tigecycline formulations |
| PT104350A (pt) | 2009-01-23 | 2010-07-23 | Hovione Farmaci Ncia S A | Processo de isolamento de tigeciclina |
| CA2751238A1 (en) | 2009-03-12 | 2010-10-07 | Wyeth Llc | Nitration of tetracyclines |
| CN103417498B (zh) * | 2012-05-18 | 2017-09-12 | 山东新时代药业有限公司 | 一种替加环素冻干粉针剂的制备方法 |
| WO2014167575A2 (en) | 2013-03-26 | 2014-10-16 | Astron Research Limited | Stable tigecycline composition |
| IN2013MU01127A (cg-RX-API-DMAC7.html) | 2013-03-26 | 2015-05-01 | Astron Res Ltd | |
| CN103202814A (zh) * | 2013-04-23 | 2013-07-17 | 成都百裕科技制药有限公司 | 一种注射用替加环素的制备方法 |
| CN105924367B (zh) * | 2016-04-18 | 2017-12-29 | 镇江高海生物药业有限公司 | 多西环素一水物的有关物质及其分析检测方法 |
| WO2019147755A1 (en) * | 2018-01-26 | 2019-08-01 | AL Pharma, Inc. | Manufacturing and packaging of a sterile drug product |
| CN108653216B (zh) * | 2018-05-28 | 2020-12-18 | 福安药业集团湖北人民制药有限公司 | 注射用替加环素 |
| WO2021063468A1 (en) | 2019-10-02 | 2021-04-08 | Anfarm Hellas S.A. | Stable parenteral pharmaceutical composition containing tigecycline and process for the preparation thereof |
| CN116531322A (zh) * | 2023-06-27 | 2023-08-04 | 遂成药业股份有限公司 | 一种高稳定性呋塞米注射液及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026248A (en) * | 1959-09-11 | 1962-03-20 | Pfizer & Co C | Thioglycerol and formaldehyde sulfoxylate stabilized tetracycline antibiotics in polyhydric alcohol solvents |
| US5494903A (en) | 1991-10-04 | 1996-02-27 | American Cyanamid Company | 7-substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines |
| US5284963A (en) | 1992-08-13 | 1994-02-08 | American Cyanamid Company | Method of producing 7-(substituted)-9-[(substituted glycyl)-amidol]-6-demethyl-6-deoxytetra-cyclines |
| US6660267B1 (en) * | 1992-12-21 | 2003-12-09 | Promega Corporation | Prevention and treatment of sepsis |
| US5675030A (en) | 1994-11-16 | 1997-10-07 | American Cyanamid Company | Method for selective extracting a 7-(hydrogen or substituted amino)-9- (substituted glycyl) amido!-6-demethyl-6-deoxytetracycline compound |
| WO2003099217A2 (en) * | 2002-05-23 | 2003-12-04 | Activbiotics, Inc. | Methods of treating bacterial infections and diseases associated therewith |
| KR20070069182A (ko) * | 2004-10-28 | 2007-07-02 | 와이어쓰 | 티게시클린 및 디곡신의 공동투여 |
| WO2006099258A1 (en) * | 2005-03-14 | 2006-09-21 | Wyeth | Tigecycline compositions and methods of preparation |
| AR057034A1 (es) | 2005-05-27 | 2007-11-14 | Wyeth Corp | Metodos para purificar tigeciclina |
-
2006
- 2006-06-15 PE PE2006000670A patent/PE20070072A1/es not_active Application Discontinuation
- 2006-06-15 AR ARP060102533A patent/AR055336A1/es unknown
- 2006-06-16 KR KR1020087001124A patent/KR20080024201A/ko not_active Withdrawn
- 2006-06-16 AU AU2006261636A patent/AU2006261636A1/en not_active Abandoned
- 2006-06-16 TW TW095121834A patent/TW200716203A/zh unknown
- 2006-06-16 JP JP2008517178A patent/JP2008543871A/ja active Pending
- 2006-06-16 CA CA002610909A patent/CA2610909A1/en not_active Abandoned
- 2006-06-16 WO PCT/US2006/023613 patent/WO2006138641A2/en not_active Ceased
- 2006-06-16 CN CNA2006800213849A patent/CN101198315A/zh active Pending
- 2006-06-16 EP EP06773424A patent/EP1898884A2/en not_active Withdrawn
- 2006-06-16 SV SV2006002575A patent/SV2007002575A/es unknown
- 2006-06-16 US US11/455,144 patent/US7705168B2/en not_active Expired - Fee Related
- 2006-06-16 BR BRPI0612228-0A patent/BRPI0612228A2/pt not_active IP Right Cessation
- 2006-06-16 PA PA20068680201A patent/PA8680201A1/es unknown
- 2006-06-16 RU RU2007145595/15A patent/RU2007145595A/ru not_active Application Discontinuation
- 2006-06-16 GT GT200600259A patent/GT200600259A/es unknown
- 2006-06-16 MX MX2007015960A patent/MX2007015960A/es unknown
-
2007
- 2007-12-05 NO NO20076264A patent/NO20076264L/no not_active Application Discontinuation
- 2007-12-06 IL IL187979A patent/IL187979A0/en unknown
- 2007-12-12 EC EC2007008005A patent/ECSP078005A/es unknown
- 2007-12-14 ZA ZA200710906A patent/ZA200710906B/xx unknown
- 2007-12-14 CR CR9594A patent/CR9594A/es unknown
-
2009
- 2009-06-05 JP JP2009136753A patent/JP2009191083A/ja not_active Withdrawn
- 2009-11-05 JP JP2009254475A patent/JP2010024252A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AR055336A1 (es) | 2007-08-22 |
| US20070026080A1 (en) | 2007-02-01 |
| RU2007145595A (ru) | 2009-07-27 |
| KR20080024201A (ko) | 2008-03-17 |
| PE20070072A1 (es) | 2007-02-25 |
| CN101198315A (zh) | 2008-06-11 |
| BRPI0612228A2 (pt) | 2011-03-29 |
| ZA200710906B (en) | 2009-03-25 |
| JP2008543871A (ja) | 2008-12-04 |
| WO2006138641A3 (en) | 2007-05-18 |
| MX2007015960A (es) | 2008-03-06 |
| ECSP078005A (es) | 2008-01-23 |
| JP2010024252A (ja) | 2010-02-04 |
| CR9594A (es) | 2008-03-07 |
| AU2006261636A1 (en) | 2006-12-28 |
| US7705168B2 (en) | 2010-04-27 |
| SV2007002575A (es) | 2007-01-03 |
| TW200716203A (en) | 2007-05-01 |
| EP1898884A2 (en) | 2008-03-19 |
| PA8680201A1 (es) | 2007-01-17 |
| WO2006138641A2 (en) | 2006-12-28 |
| IL187979A0 (en) | 2008-03-20 |
| GT200600259A (es) | 2007-05-08 |
| NO20076264L (no) | 2008-03-10 |
| JP2009191083A (ja) | 2009-08-27 |
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