EP1916996A2 - Realisation d'une solution d'oxaliplatine et contenant et jeu de contenants avec cette solution - Google Patents
Realisation d'une solution d'oxaliplatine et contenant et jeu de contenants avec cette solutionInfo
- Publication number
- EP1916996A2 EP1916996A2 EP06776798A EP06776798A EP1916996A2 EP 1916996 A2 EP1916996 A2 EP 1916996A2 EP 06776798 A EP06776798 A EP 06776798A EP 06776798 A EP06776798 A EP 06776798A EP 1916996 A2 EP1916996 A2 EP 1916996A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oxaliplatin
- acid
- solution
- concentration
- container
- 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.)
- Withdrawn
Links
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 title claims abstract description 79
- 229960001756 oxaliplatin Drugs 0.000 title claims abstract description 79
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 239000000203 mixture Substances 0.000 title description 3
- 239000000243 solution Substances 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 32
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003708 ampul Substances 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 235000019846 buffering salt Nutrition 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims 1
- 238000007865 diluting Methods 0.000 abstract 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- SYPAAUOZTIBVHX-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O SYPAAUOZTIBVHX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-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
- 238000009472 formulation Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- A61K9/0012—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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
-
- 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
- A61K31/28—Compounds containing heavy metals
- A61K31/282—Platinum compounds
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
Definitions
- EP 0 943 331 B1 describes a stable oxaliplatin solution with oxalic acid or an oxalic acid salt as buffer.
- the solution can be filled into an ampoule, glass vial (page 8, line 10), infusion bag or syringe. Disadvantage of this formulation is a certain toxicity of oxalic acid.
- WO 03/047 587 discloses a stable oxaliplatin solution in suitable containers (page 12, line 28) with lactic acid or a lactic acid salt as buffer.
- the present invention relates to the use of an acid to increase the solubility of oxaliplatin in an aqueous solution.
- the invention relates to a process for the preparation of an aqueous oxaliplatin solution in which oxaliplatinol is dissolved in water by adding an acid to an oxaliplatin concentration which increases over an acid-free aqueous oxaliplatin solution, in particular under otherwise identical conditions is.
- the present invention relates to a process for the preparation of a solution consisting of oxaliplatin, an acid and water, in which oxaliplatin is dissolved in water by adding an acid to an oxaliplatin concentration which is elevated over an acid-free aqueous oxaliplatin solution.
- oxaliplatin in the method of the present invention, can be dissolved in water by adding the acid to the highest oxaliplatin saturation concentration achievable with this acid.
- an oxaliplatin concentration which is in the range which is determined on the one hand by the saturation concentration of an acid-free aqueous oxaliplatin solution and on the other hand by the highest saturation concentration in the presence of the acid is defined and the acid is added until the predetermined concentration is reached.
- the solution is free from carbohydrate such as e.g. Lactose, glucose, maltose, fructose, galactose or dextrans (e.g., 10-70).
- carbohydrate such as e.g. Lactose, glucose, maltose, fructose, galactose or dextrans (e.g., 10-70).
- the solution is free of polyethylene glycol, e.g. Polyethylene glycol 200, 300, 400 and 600 added.
- an integer or half-integer (integer plus 1) oxaliplatin concentration of a customary concentration unit of measure preferably the unit of measure mg / ml or molar.
- an inorganic and / or organic acid can be used in the process according to the invention.
- At least one inorganic acid can be used from the group formed by sulfuric acid, nitric acid and phosphoric acid.
- sulfuric acid is used.
- At least one organic acid may be used from the group formed by citric acid, succinic acid, ascorbic acid, oxalic acid, lactic acid and malonic acid.
- Citric acid is preferably used.
- a buffering salt Furthermore, in the method according to the invention, it is additionally possible to use a buffering salt. Furthermore, in the method according to the invention, a pH of 1 to 7 and in particular 1.5 to 4 can be set.
- the container can be closed under an inert gas.
- a vial, a screw-cap bottle or an ampoule can be provided as a container.
- a vial as a bottle, which is designed as a single-dose or multi-dose container.
- Another embodiment of the invention relates to a container of aqueous oxaliplatin solution obtainable by the process according to the invention.
- Another embodiment of the invention relates to a container having an acidic oxaliplatin aqueous solution of an oxaliplatin concentration which is elevated relative to an acid-free oxaliplatin aqueous solution.
- a further embodiment of the invention relates to a container with an acidic aqueous oxaliplatin solution with the highest oxaliplatin saturation concentration, which is achievable with the aid of this acid, or with the highest for the acid characteristic oxaliplatin saturation concentration.
- a further embodiment of the invention relates to a container with an acidic aqueous oxaliplatin solution having an integer or half integer (integer plus M) oxaliplatin concentration of a conventional concentration unit, preferably the unit mg oxaliplatin / ml solution or mg oxaliplatin / mg solution or molar.
- a further embodiment of the invention relates to a set of or containers according to the invention each having an acidic oxaliplatin aqueous solution having an integer or integer (integer plus M) oxaliplatin concentration of a conventional concentration unit, preferably mg oxaliplatin / ml Solution or mg oxaliplatin / mg solution or molar.
- an embodiment of the invention relates to a set of or containers according to the invention each having an acidic aqueous oxaliplatin solution with an integer or half integer (integer plus M) oxaliplatin concentration of a conventional concentration unit, preferably the unit mg oxaliplatin / ml Solution or mg oxaliplatin / mg solution or molar, whereby the oxaliplatin concentration of at least one container deviates from the concentration of the other container (s).
- the present invention further comprises the solutions prepared according to one of the described methods.
- 5 examples are used to tabulate the increased oxaliplatin solubility in the presence of acid.
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne un procédé pour réaliser une solution aqueuse d'oxaliplatine, selon lequel de d'oxaliplatine est dissoute dans de l'eau par ajout d'un acide jusqu'à l'obtention d'une concentration d'oxaliplatine supérieure à celle d'une solution aqueuse d'oxaliplatine sans acide. La présente invention porte également sur un contenant et un jeu de contenants avec cette solution.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005038347A DE102005038347A1 (de) | 2005-08-11 | 2005-08-11 | Herstellung einer Oxaliplatin-Lösung und Behälter sowie Behälter-Set mit der Lösung |
| PCT/EP2006/007982 WO2007017291A2 (fr) | 2005-08-11 | 2006-08-11 | Realisation d'une solution d'oxaliplatine et contenant et jeu de contenants avec cette solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1916996A2 true EP1916996A2 (fr) | 2008-05-07 |
Family
ID=37179055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06776798A Withdrawn EP1916996A2 (fr) | 2005-08-11 | 2006-08-11 | Realisation d'une solution d'oxaliplatine et contenant et jeu de contenants avec cette solution |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20100140131A1 (fr) |
| EP (1) | EP1916996A2 (fr) |
| DE (1) | DE102005038347A1 (fr) |
| WO (1) | WO2007017291A2 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5929607B2 (ja) * | 2012-08-06 | 2016-06-08 | ニプロ株式会社 | オキサリプラチン製剤 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004052877A1 (de) * | 2004-11-02 | 2006-05-04 | Ebewe Pharma Ges.M.B.H. Nfg.Kg | Stabile wässrige Formulierungen eines Platin Derivats |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9804013D0 (en) * | 1998-02-25 | 1998-04-22 | Sanofi Sa | Formulations |
| US7012072B2 (en) * | 2000-12-12 | 2006-03-14 | Debiopharm S.A. | Pharmaceutical oxaliplatinum preparation for parenteral administration and method for obtaining same |
| CA2357955C (fr) * | 2001-09-28 | 2008-11-18 | Itf Technologies Optiques Inc./Itf Optical Technologies Inc. | Depolariseur tout fibre optique |
| US6476068B1 (en) * | 2001-12-06 | 2002-11-05 | Pharmacia Italia, S.P.A. | Platinum derivative pharmaceutical formulations |
| DE10314377A1 (de) * | 2003-03-28 | 2004-10-07 | Stada Arzneimittel Ag | Gebrauchsfertige Oxaliplatin-Lösungen |
| WO2005020980A1 (fr) * | 2003-08-28 | 2005-03-10 | Mayne Pharma Pty Ltd | Formulations d'oxaliplatine contenant de l'acide |
| US20060063833A1 (en) * | 2004-09-22 | 2006-03-23 | Edgar Schridde | Ready-to-use oxaliplatin solutions |
| DE102004063764A1 (de) * | 2004-12-29 | 2006-07-13 | Hexal Ag | Kunststoff-Flasche für Oxaliplatin |
-
2005
- 2005-08-11 DE DE102005038347A patent/DE102005038347A1/de not_active Withdrawn
-
2006
- 2006-08-11 EP EP06776798A patent/EP1916996A2/fr not_active Withdrawn
- 2006-08-11 US US12/063,531 patent/US20100140131A1/en not_active Abandoned
- 2006-08-11 WO PCT/EP2006/007982 patent/WO2007017291A2/fr not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004052877A1 (de) * | 2004-11-02 | 2006-05-04 | Ebewe Pharma Ges.M.B.H. Nfg.Kg | Stabile wässrige Formulierungen eines Platin Derivats |
Also Published As
| Publication number | Publication date |
|---|---|
| US20100140131A1 (en) | 2010-06-10 |
| WO2007017291A2 (fr) | 2007-02-15 |
| DE102005038347A1 (de) | 2007-02-15 |
| WO2007017291A3 (fr) | 2007-05-24 |
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Legal Events
| Date | Code | Title | Description |
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| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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| 17P | Request for examination filed |
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| 17Q | First examination report despatched |
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| DAX | Request for extension of the european patent (deleted) | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
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| 18D | Application deemed to be withdrawn |
Effective date: 20120301 |