CA2549304A1 - Polymethylmethacrylate bone cement containing a homogeneously distributed dye - Google Patents
Polymethylmethacrylate bone cement containing a homogeneously distributed dye Download PDFInfo
- Publication number
- CA2549304A1 CA2549304A1 CA002549304A CA2549304A CA2549304A1 CA 2549304 A1 CA2549304 A1 CA 2549304A1 CA 002549304 A CA002549304 A CA 002549304A CA 2549304 A CA2549304 A CA 2549304A CA 2549304 A1 CA2549304 A1 CA 2549304A1
- Authority
- CA
- Canada
- Prior art keywords
- dye
- liquid
- bone cement
- solubilizer
- polymethylmethacrylate bone
- 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.)
- Granted
Links
- 239000002639 bone cement Substances 0.000 title claims abstract 11
- 229920003229 poly(methyl methacrylate) Polymers 0.000 title claims abstract 11
- 239000004926 polymethyl methacrylate Substances 0.000 title claims abstract 11
- 239000007788 liquid Substances 0.000 claims abstract 17
- 239000000178 monomer Substances 0.000 claims abstract 14
- 239000002904 solvent Substances 0.000 claims abstract 12
- 239000000203 mixture Substances 0.000 claims abstract 9
- 239000007787 solid Substances 0.000 claims abstract 8
- 230000002209 hydrophobic effect Effects 0.000 claims abstract 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract 4
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims abstract 3
- 235000011837 pasties Nutrition 0.000 claims abstract 3
- 229920000193 polymethacrylate Polymers 0.000 claims abstract 2
- 239000000843 powder Substances 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 2
- -1 aliphatic alcohols Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 2
- 150000002888 oleic acid derivatives Chemical class 0.000 claims 2
- UBEIMDKGOYBUKT-FLIQGJDUSA-N 1,2,3-trilinolenoylglycerol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC UBEIMDKGOYBUKT-FLIQGJDUSA-N 0.000 claims 1
- HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 claims 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims 1
- 229930003779 Vitamin B12 Natural products 0.000 claims 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940099898 chlorophyllin Drugs 0.000 claims 1
- 235000019805 chlorophyllin Nutrition 0.000 claims 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 claims 1
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical class CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims 1
- 229940097275 indigo Drugs 0.000 claims 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 1
- 229940107698 malachite green Drugs 0.000 claims 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 claims 1
- 238000007348 radical reaction Methods 0.000 claims 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 claims 1
- 239000011715 vitamin B12 Substances 0.000 claims 1
- 235000019163 vitamin B12 Nutrition 0.000 claims 1
- 150000003722 vitamin derivatives Chemical class 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants
Abstract
A polymethylmethacrylate bone cement with a liquid monomer component and a solid component contains in the monomer liquid, for example, 0.001-1.00 mass percent of a dye or dye mixture that is insoluble or poorly soluble in methacrylic acid methylester and, for example, 0.001-2.00 mass percent of a synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer for the dye or dye mixture. The solubilizer preferably is liquid or pasty at room temperature. The monomer liquid is translucent at room temperature.
Preferably, 0.001-1.00 mass percent of a dye or dye mixture that is insoluble or poorly soluble in methacrylic acid methylester and, preferably, 0.001-2.00 mass percent of a synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer that is liquid or pasty at room temperature are homogeneously dissolved in the polymethacrylate or polymethylacrylate of the powder component.
Preferably, 0.001-1.00 mass percent of a dye or dye mixture that is insoluble or poorly soluble in methacrylic acid methylester and, preferably, 0.001-2.00 mass percent of a synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer that is liquid or pasty at room temperature are homogeneously dissolved in the polymethacrylate or polymethylacrylate of the powder component.
Claims (9)
1. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component, characterized A in that a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methylester and a synthetically produced, protein-free, hydrophobic, low molecu-lar or oligomeric solubilizer for the dye or dye mixture are dissolved in the mono-mer liquid;
B in that the monomer liquid is translucent at room temperature;
C and in that a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methylester and a synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer are homogeneously distributed in the polyme-thacrylate or polymethylacrylate of the powder component.
B in that the monomer liquid is translucent at room temperature;
C and in that a dye/dye mixture that is insoluble or poorly soluble in methacrylic acid methylester and a synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer are homogeneously distributed in the polyme-thacrylate or polymethylacrylate of the powder component.
2. Polymethylmethacrylate bone cement according to claim 1, whereby the dye/dye mixture is present at a concentration of 0.001-1.00 mass percent and the solubilizer is present at a concentration of 0.001-2.00 mass percent in the monomer liquid or, respectively, in the polymethacrylate or polymethylacrylate.
3. Polymethylmethacrylate bone cement according to claim 1, whereby the solubilizer is liquid or pasty at room temperature.
4. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to any one of the claims 1-3, characterized in that the dye/dye mixture and the synthetically produced, protein-free, hydrophobic, low molecular or oligomeric solubilizer form soluble adducts with the dye/dye mixture in the monomer liquid.
5. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to any one of the claims 1-4, characterized in that oleic acid esters and/or elaidic acid esters and/or linoleic acid esters and/or linolenic acid esters of the aliphatic alcohols with 1 to 22 carbon atoms or oligomers of these oleic acid esters are used as solubilizer.
6 6. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to any one of the claims 1-5, characterized in that methacrylic acid esters or acrylic acid esters of the aliphatic alcohols with 4 to 16 carbon atoms or oligomers of these methacrylic acid esters or acrylic acid esters with a molecular mass of less than 3,000 g/mol are used as solubilizers.
7. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to any one of the claims 1-6, characterized in that glycerine trioleate, glycerine trilinolate, glycerine trilinolenate, and glycerine trielaidinate are used as solubilizer.
8. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to any one of the claims 1-7, characterized in that the solubilizer contains double bonds that can be polymerized by radical reaction.
9. Polymethylmethacrylate bone cement with a liquid monomer component and a solid component according to any one of the claims 1-8, characterized in that chlorophyllin, indigo, malachite green, crystal violet, copper phthalocyanine, cobalt phthalocyanine, vitamin B12, and derivatives thereof are used as dyes.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005029218.6 | 2005-06-22 | ||
| DE102005029218 | 2005-06-22 | ||
| DE102005033210.2 | 2005-07-13 | ||
| DE102005033210A DE102005033210B4 (en) | 2005-06-22 | 2005-07-13 | Polymethylmethacrylate bone cement |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2549304A1 true CA2549304A1 (en) | 2006-12-22 |
| CA2549304C CA2549304C (en) | 2010-05-25 |
Family
ID=37400899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2549304A Expired - Fee Related CA2549304C (en) | 2005-06-22 | 2006-06-02 | Polymethylmethacrylate bone cement containing a homogeneously distributed dye |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7655706B2 (en) |
| EP (1) | EP1736179B1 (en) |
| JP (1) | JP4886381B2 (en) |
| AT (1) | ATE531398T1 (en) |
| AU (1) | AU2006202509B2 (en) |
| BR (1) | BRPI0602320B8 (en) |
| CA (1) | CA2549304C (en) |
| DE (1) | DE102005033210B4 (en) |
| DK (1) | DK1736179T3 (en) |
| ES (1) | ES2374830T3 (en) |
| PL (1) | PL1736179T3 (en) |
| PT (1) | PT1736179E (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111905150A (en) * | 2020-08-10 | 2020-11-10 | 中国人民解放军总医院第一医学中心 | Bone cement with color development function |
| CN114053477A (en) * | 2020-08-03 | 2022-02-18 | 首都医科大学附属北京朝阳医院 | Anti-myeloma nano bone cement and preparation method and application thereof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005032110B3 (en) * | 2005-07-07 | 2006-08-17 | Heraeus Kulzer Gmbh | Colored polymethyl-methacrylate cement to anchor endoprostheses in orthopoedic surgery incorporates a mixture of one or more dyes |
| US8415406B2 (en) * | 2005-07-22 | 2013-04-09 | Howmedica Osteonics Corp. | Setting time indicator for acrylic bone cement |
| US20070021526A1 (en) * | 2005-07-22 | 2007-01-25 | Howmedica Osteonics Corp. | Setting time indicator for acrylic bone cement |
| DE102007050762B3 (en) * | 2007-10-22 | 2009-05-07 | Heraeus Medical Gmbh | Paste polymethyl methacrylate bone cement and its use |
| US8133436B2 (en) * | 2008-08-05 | 2012-03-13 | Howmedica Osteonics Corp. | Polyethylene cross-linked with an anthocyanin |
| CN105246517B (en) * | 2013-04-08 | 2018-06-12 | 伊诺西亚公司 | For the increased acrylic cement of sclerotin |
| KR101872329B1 (en) * | 2016-07-07 | 2018-06-28 | 국민대학교산학협력단 | Random number generator for supporting multi entropy pool |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2842839C3 (en) * | 1978-10-02 | 1986-11-13 | NATEC Institut für naturwissenschaftlich-technische Dienste GmbH, 2000 Hamburg | Self-hardening compound based on polymethyl methacrylate and its use |
| DE2905878A1 (en) * | 1979-02-16 | 1980-08-28 | Merck Patent Gmbh | IMPLANTATION MATERIALS AND METHOD FOR THEIR PRODUCTION |
| FR2516796B1 (en) * | 1981-11-20 | 1986-06-06 | Altulor Sa | COMPOSITIONS FOR SURGICAL CEMENT BASED ON AT LEAST ONE ACRYLIC MONOMER AND AT LEAST ONE ACRYLIC POLYMER |
| DE3245956A1 (en) * | 1982-12-11 | 1984-06-14 | Beiersdorf Ag, 2000 Hamburg | SURGICAL MATERIAL |
| ATE50503T1 (en) * | 1985-06-20 | 1990-03-15 | Ceraver | CEMENT FOR ANCHORING BONE PROSTHESES. |
| US5258420A (en) * | 1987-07-30 | 1993-11-02 | Pfizer Hospital Products Group, Inc. | Bone cement for sustained release of substances |
| US6743438B2 (en) * | 1993-10-26 | 2004-06-01 | Pbh, Inc. | Colored contact lenses and method of making same |
| DE4433201A1 (en) * | 1994-09-17 | 1996-03-21 | Merck Patent Gmbh | Process for the production of active ingredient-containing bone cements |
| DE4435680A1 (en) * | 1994-10-06 | 1996-04-11 | Merck Patent Gmbh | Porous bone substitute materials |
| AU5973496A (en) * | 1995-06-06 | 1996-12-24 | Merck & Co., Inc. | Bisphosphonate cement composition to prevent aseptic loosening of orthopedic implant devices |
| DE19641775A1 (en) * | 1996-08-22 | 1998-02-26 | Merck Patent Gmbh | Process for the production of active ingredient-containing bone cements |
| AU747407B2 (en) * | 1998-04-14 | 2002-05-16 | Bioagency Ag | Use of organophosphoric compounds for the therapeutic and preventative treatment of infections |
| US20060062825A1 (en) * | 2004-04-19 | 2006-03-23 | Maria Maccecchini | Method of implanting a sterile, active agent-coated material and composition made according to same |
| DE102005032110B3 (en) * | 2005-07-07 | 2006-08-17 | Heraeus Kulzer Gmbh | Colored polymethyl-methacrylate cement to anchor endoprostheses in orthopoedic surgery incorporates a mixture of one or more dyes |
-
2005
- 2005-07-13 DE DE102005033210A patent/DE102005033210B4/en not_active Expired - Fee Related
-
2006
- 2006-06-02 CA CA2549304A patent/CA2549304C/en not_active Expired - Fee Related
- 2006-06-03 DK DK06011580.5T patent/DK1736179T3/en active
- 2006-06-03 PT PT06011580T patent/PT1736179E/en unknown
- 2006-06-03 AT AT06011580T patent/ATE531398T1/en active
- 2006-06-03 PL PL06011580T patent/PL1736179T3/en unknown
- 2006-06-03 EP EP06011580A patent/EP1736179B1/en not_active Not-in-force
- 2006-06-03 ES ES06011580T patent/ES2374830T3/en active Active
- 2006-06-06 US US11/447,807 patent/US7655706B2/en active Active
- 2006-06-15 AU AU2006202509A patent/AU2006202509B2/en not_active Ceased
- 2006-06-21 BR BRPI0602320A patent/BRPI0602320B8/en not_active IP Right Cessation
- 2006-06-22 JP JP2006173045A patent/JP4886381B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114053477A (en) * | 2020-08-03 | 2022-02-18 | 首都医科大学附属北京朝阳医院 | Anti-myeloma nano bone cement and preparation method and application thereof |
| CN111905150A (en) * | 2020-08-10 | 2020-11-10 | 中国人民解放军总医院第一医学中心 | Bone cement with color development function |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2549304C (en) | 2010-05-25 |
| EP1736179B1 (en) | 2011-11-02 |
| US7655706B2 (en) | 2010-02-02 |
| BRPI0602320B1 (en) | 2018-04-03 |
| ATE531398T1 (en) | 2011-11-15 |
| EP1736179A2 (en) | 2006-12-27 |
| JP4886381B2 (en) | 2012-02-29 |
| DK1736179T3 (en) | 2012-01-23 |
| DE102005033210B4 (en) | 2008-04-30 |
| ES2374830T3 (en) | 2012-02-22 |
| BRPI0602320B8 (en) | 2021-06-22 |
| AU2006202509A1 (en) | 2007-01-11 |
| DE102005033210A1 (en) | 2007-01-04 |
| AU2006202509B2 (en) | 2008-06-05 |
| PL1736179T3 (en) | 2012-03-30 |
| PT1736179E (en) | 2012-01-12 |
| JP2007000636A (en) | 2007-01-11 |
| BRPI0602320A (en) | 2007-02-21 |
| EP1736179A3 (en) | 2010-01-13 |
| US20060293407A1 (en) | 2006-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20220602 |