WO2009053947A2 - Revêtement de surface pour empêcher la lixiviation cationique - Google Patents

Revêtement de surface pour empêcher la lixiviation cationique Download PDF

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Publication number
WO2009053947A2
WO2009053947A2 PCT/IB2008/054475 IB2008054475W WO2009053947A2 WO 2009053947 A2 WO2009053947 A2 WO 2009053947A2 IB 2008054475 W IB2008054475 W IB 2008054475W WO 2009053947 A2 WO2009053947 A2 WO 2009053947A2
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WO
WIPO (PCT)
Prior art keywords
ppb
syringe
equal
cations
oil
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Application number
PCT/IB2008/054475
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English (en)
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WO2009053947A3 (fr
Inventor
Laurence Boulange
David Benjamin Montgomery
Sébastien JANVIER
Julie Haguet
Frédérique CROZET
Florestan Desmaris
Delphine Brissaud
Charlène SOULET
Estelle Appert
Jean Charles Joud
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Becton Dickinson France
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Publication of WO2009053947A2 publication Critical patent/WO2009053947A2/fr
Publication of WO2009053947A3 publication Critical patent/WO2009053947A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C26/00—Coating not provided for in groups C23C2/00 - C23C24/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
    • A61M5/178—Syringes
    • A61M5/31—Details
    • A61M5/3129—Syringe barrels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/123—Treatment by wave energy or particle radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
    • A61M5/178—Syringes
    • A61M5/31—Details
    • A61M5/3129—Syringe barrels
    • A61M2005/3131—Syringe barrels specially adapted for improving sealing or sliding
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/10—Homopolymers or copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers

Definitions

  • the invention generally relates to drug holding components of drug delivery systems implementing an injection like process for delivering a drug or drug formulation directly to a patient or through a fluid administration circuit.
  • the invention relates to pre-fillable and pre- filled components of such drug delivery systems.
  • Many drug delivery systems like syringes, pre-filled syringes, drug cartridge and needless injectors include an internal chamber for receiving a medicament and a piston, the piston being slidable within the interior chamber.
  • Such drug delivery systems are often made of glass so two problems are to be solved, the first one is to improve gliding properties in syringe barrels and the second one is to obtain a good stability of the active principles contained in such barrels.
  • the siliconization of the inner wall of the chamber allows a smooth movement or gliding of the piston within the chamber.
  • the silicone oil used for pharmaceutical applications is a polydimethylsiloxane polymer, sprayed inside the barrel.
  • silicone oil is an apolar molecule that can mostly generate hydrophobic interactions with other molecules or particles in solutions. When an emulsion with silicone oil comes in contact with proteins, it generates some changes in their structure leading to a loss of protein activity and/or a protein aggregation.
  • the aim of the invention is to create surface coatings that prevent cation leaching from glass and stabilize the silicone oil onto the syringe barrel reducing further interactions with proteins stored in the syringe barrel.
  • the current solution developed by the biotech market is a baked silicone syringe with a Flurotec stopper.
  • the baked silicone syringe displays a lower content of silicone by a factor 10 in comparison with a standard sprayed silicone.
  • the current solution is not completely satisfactory as there is some limitation in the process. Indeed, only luer syringes can be produced by using this process, secondly, there are some therapeutic proteins that can aggregate when stored in a baked silicone syringe.
  • thermal barrier coating adapted to provide a thermally insulating protective barrier on a component was patented by Rolls-Royce (US patent 4,332,618).
  • the coating was applied to the components by spraying methods and being ductile when exposed to high temperatures.
  • the coating comprises a mixture containing constituents of glass microspheres; a ceramic frit of finely divided particles of alkali silicate titanate glass; and a refractory filler material of finely divided particles (micronized mica; aluminum oxide of mullite). All of the constituents of the mixture were suspended in a high temperature resistant binder material such as potassium silicate, sodium silicate or aluminum orthophosphate.
  • Pilkington pic. proposed a coating, which acted as barrier layers to inhibit migration of alkali metal ions from a glass surface (Na leaching between 40 and 700 ng/cm 2 ). It acted as color suppressing underlayers for overlying infra-red reflecting or electrically conducting layers.
  • the coating was deposited by pyrolysis of a gaseous mixture of a silane, an unsaturated hydrocarbon and an oxygen-containing gas other than carbon dioxide which does not react with the silane at room temperature on a hot glass surface at a temperature of 600 0 C to 750 0 C (US patent 4,995,89 3 and US 5,165,972).
  • the hollow glass body had an interior coating preferably composed by oxides such as SiO2, AI2O3, TiO2. There was a predetermined coating thickness according to the required chemical resistance or working conditions for forming the glass body.
  • the coating is advantageously provided by means of a PICVD process (US patent 6,200,658 B1 ).
  • PPG Industries patented amorphous metal oxide barrier layers of titanium oxide, zirconium oxide and zinc/tin oxide that acted as alkali metal ion barrier layers at thicknesses below 18 nm.
  • the amorphous metal oxide barrier layers are most effective when the density of the layer is equal to or greater than 75% of the crystalline density.
  • the barrier layers prevent migration of alkali metal ions such as sodium ions from glass substrates into a medium e.g. electrolyte of a photochromic cell, liquid material of a liquid crystal display device contacting the glass surface and a photocatalytic coating.
  • the properties of the medium, particularly electroconductive metal oxide coatings, are susceptible to deterioration by the presence of sodium ions migrating from the glass (US patent 6,352,755 B1 ).
  • Becton Dickinson proposed a method to reduce high breakout and sustaining forces between slidable surfaces.
  • a film of lubricant applied at least to one of the surfaces was then subjected to an ionizing plasma.
  • the invention includes articles having slidable surfaces of low breakout and sustaining forces. This treatment was applied on silicone oils (US patents 4,767,414 & 4,822,632).
  • Becton Dickinson also protected a method for preparing stable coatings of a silicone lubricant on a low surface energy polymeric surface. It included plasma treatment of the surface in an atmosphere of a siloxane monomer.
  • a layer of polysiloxane was deposited on the low energy surface to give a polysiloxane surface.
  • a film of a polysiloxane lubricant having a surface tension substantially the same as or less than the surface energy of the polysiloxane surface was applied to the polysiloxane layer (US 4,844,986).
  • Becton Dickinson also developed a multi component system.
  • a first crosslinked basement lubricant was coated onto a syringe barrel.
  • a second lubricant was coated over the crosslinked lubricant.
  • a low viscosity prebasement lubricant was evenly coated onto the inside surface of the syringe barrel and then crosslinked by a plasma to a viscous liquid or substantially solid basement lubricant.
  • a second surface lubricant is then applied over the basement lubricant (US patent 5,338,312).
  • NovoNordisk proposed a coating system for articles where plastic materials slide against flexible rubber materials.
  • the coating system was a silicone oil based coating having a viscosity of at least 200,000 centistokes.
  • the coating comprises in a preferred embodiment a silicone oil based block or graft copolymer, or segmented copolymer.
  • Such an article was preferably a medical article, such as a container or an injection cylinder and a stopper.
  • the coatings were particularly useful for coating containers for storage and administration of liquid protein solutions, such as insulin formulations (US 6,482,509 B2).
  • One aspect of the present invention comprises a method to prepare a syringe comprising the steps of: a. creating an homogeneous and continuous inner oil layer inside a syringe, b. exposing said inner oil layer to an oxidative plasma gas, said oil being a non reactive oil.
  • the method according to the invention further comprises before the step of creating said inner oil layer a preliminary step of oxidative plasma.
  • the method according to the invention comprises a step of sterilization.
  • non reactive oil is silicon oil.
  • the silicon oil is chosen amongst the alkyl polysiloxane.
  • the alkylpolysiloxane are chosen in the group comprising polydimethylsiloxane, polydiethylesiloxane and polydipropylsiloxane.
  • the oil has a viscosity from preferably around 100O cSt.
  • the homogeneous and continuous oil layer is 0,5 to 1 ,5 ⁇ m
  • the oxidative plasma gas is oxygen, or an oxygen containing gas.
  • the oxidative plasma is generated under atmospheric pressure or vacuum.
  • the oxidative plasma is generated by microwaves, audio frequencies, radio-frequencies, low frequencies, DC glow discharge, Corona discharge or arc discharge.
  • the syringe is glass based, such as borosilicate
  • the ionizing plasma was done by using an oxidative gas such as air but pure oxygen or other oxidative gases can also be used.
  • the method can be applied or used on on Luer syringes and for syringes in polymers.
  • the silicone oil used for pharmaceutical applications is a polydimethylsiloxane polymer. This polymer is directly exposed to a plasma gas after spraying inside the barrel. The plasma is done in a chamber by adding an oxidative gas such as air or oxygen or a mixture of oxygen with an inert gas assuring a barrier effect whereas an outer layer can assure the gliding effect.
  • the inner layer is an effective barrier against monovalent, divalent, thvalent and tetravalent cations extracted from glass.
  • Another aspect of the invention is the use of a non-reactive oil exposed to an oxidative plasma treatment as a surface coating of a syringe barrel to be filled with a pharmaceutical preparation, to inhibit leaching of chemical species from syringe raw material into the said pharmaceutical preparation.
  • the chemical species are cations.
  • Another aspect of the invention is to provide a syringe to be filled with a pharmaceutical preparation, characterized in that the barrier effect for all the cation elements is inferior or equal to 250 ng/cm 2 , preferably inferior or equal to 200 ng/cm 2 , more preferably inferior or equal to 150 ng/cm 2
  • cation is inferior or equal to 150 ng/cm 2 , preferably inferior or equal to 100 ng/cm 2 , more preferably inferior or equal to 90 ng/cm 2
  • the effect achieved by the method of the invention is of long duration and syringes retain the advantages of good gliding properties and leaching inhibition of chemical species.
  • the homogeneous and continuous inner oil layer is created inside a syringe.
  • Application of said continuous inner layer may be accomplished by any suitable method, such as, for example dipping, brushing spraying and the like.
  • the oil layer may be applied in a pure form or in water emulsion with surfactant.
  • the non reactive oil chosen amongst the alkylpolysiloxane in some embodiments is a polydimethyl siloxane, such as DOW CORNINGS360 ® polydimethylsiloxane or NuSiL ® polydimethylsiloxane having a viscosity ranging from about 100 to about 1 ,000,000 cst.
  • the syringe is exposed to an oxidative plasma gas.
  • the plasma treatment may be carried out in any plasma generator as for example those described in US3847652 or French patent applications 08FR51900 or 08FR51901.
  • the best embodiment is a Hypak ® syringe formed by an inner layer obtained by CVD technology and an outer layer composed by a sprayed silicone with a viscosity of 1000 cSt plasma treated using an ionizing gas (oxygen) for 15 sec.
  • Example 1 Barrier effect of the coatings against cations coming from glass
  • Si Silicon (Si) is present in the glass as SiO2 and constitutes the basis of the glass,
  • Sodium (Na) is present in the glass as Na2 ⁇ and lowers the melting temperature
  • Boron (B) is present in the glass as B 2 O 3 and used to get a better thermal resistance
  • Aluminum (Al) is present in the glass as AI 2 O 3 in order to get better mechanical properties
  • Magnesium (Mg) is present in the glass as MgO and used to lower the melting temperature.
  • Sodium is analyzed by Flamme - Atomic Absorption Spectrometry (Flamme-AAS), using an air/acetylene flamme, a sodium hallow cathode and a detection at 589nm. An external calibration was performed between 0.3 and 2.0 ppm. Solutions of three syringes were pooled together for analysis.
  • Flamme-AAS Flamme - Atomic Absorption Spectrometry
  • Method 2 for Boron, Aluminum and Magnesium Nitric acid extracts using ultrasonic bath. A rigid needle shield was placed on the syringes, which are filled with 1 mL of 1 % nitric acid, stoppered with a Flurotec® plunger stopper and placed for 2 hours in an ultrasonic bath at room temperature. Boron, Aluminum, Magnesium were analyzed by ICP/MS in one single method, using an argon plasma and a mass spectrometer for the detection, with the specific masses of 11 for Boron, 27 for Aluminum and 24 for Magnesium. An external calibration was performed using one single level at 10ppb for all elements and a check at 5ppb for all elemnts. The calibration was validated between 1 and 10 ppb for Boron, 2 and 10 ppb for Aluminum and 4 and 10 ppb for Magnesium. Solutions of four syringes are pooled together for analysis.
  • Method 3 for Silicium Purified water extracts using autoclave plus 24 hour agitation: A rigid needle shield was placed on the syringes, which were filled with 1 mL of deionized water and stoppered with unsiliconized parylene coated plunger stoppers and autoclaved for 1 hour at 121 O. They w ere then agitated for 24 hours before analysis.
  • Silicium was analyzed by ICP/MS using an argon plasma and a mass spectrometer for the detection, with the specific mass of 28 for silicium. Silicium extracted from the glass as well as silicium extracted from the coatings (referred as to C1 to C6 and P1 to P5) were quantified together. An external calibration was performed between 10 and 35 ppb. Solution from a single syringe was diluted in 1 % nitric acid to reach the range of the calibration curve. [0067] For all the cation elements, the barrier effect measured by analytical tools was then expressed in ng/cm 2 .
  • A1 bis C2+P2 0.8 ppm 15% 80
  • A1 C1 +P2 5 ppb 25% 0.5
  • A2 P2 5 ppb 1 1% 0.5
  • A1 bis C2+P2 4ppb 0% 0.4
  • C1 provide a filter effect against divalent magnesium cation. It corresponds to a CVD process using pure HMDSO. The presence of oxygen in the reaction chamber decreases the filter effect against Mg 2+ .
  • PTS systems are efficient barriers for divalent cations and bilayers can improve the filter effect against divalent magnesium cation compared to solid coatings alone.
  • A1 C1 +P2 23ppb 25% 2.3
  • A1 bis C2+P2 10ppb 0% 1.0
  • A2 P2 30 ppb 0% 3.0
  • A1 bis C2+P2 20 ppb 0% 2.0
  • Silicium quantified by ICP/MS can come from both the glass or the coating : polymerized HMDSO by CVD or silicone (DC360 10OOcSt - PDMS) oil.
  • Silicon element quantified by ICP/MS can come from both the glass or the coating : polymerized HMDSO by CVD or silicone (DC360 100OcSt - PDMS) oil.
  • the secondary structure content are based on the following structures deposited in the Protein Databank (http://www.rcsb.org/pdb/), Protein references are given in bracket and given for a monomer
  • Insulin is a polypeptide hormone that regulates glucose metabolism.
  • Bovine Serum Albumin is a serum albumin that is used to stabilize some enzymes and plays a role in transport of low hydrosoluble proteins.
  • the protein stability was studied at 37O and the h ydrodynamic diameter of the protein (nm) was measured by Dynamic Light Scattering (DLS). The measurements were made with a He Ne laser 633 nm at 173° in order to verify the presence of aggregates and to minimize the effects of dust contamination.
  • Each native protein has a specific hydrodynamic diameter that is typically less than 20 nm.
  • a study of the kinetics was performed at 37°C and the hydrodynamic diameter was measured after 7, 15 and 30 days. When proteins formed aggregates, large hydrodynamic diameters were measured.
  • A1 C1 +P2 Peak 2 260 15 320 38 215 45
  • Bilayer A2 P2 Peak 2 260 15 260 35 710 19
  • A1 bis C2+P2 Peak 2 260 15 580 32 490 43
  • Peak 1 corresponds to the hydrodynamic diameter of the native protein and peaks 2 to the protein aggregates. For each peak the diameter (nm) and the percentage of light intensity is mentioned.
  • A1 C1+P2 Peak 2 280 76 600 45 110 53
  • Bilayer A2 P2 Peak 2 280 76 720 40 490 52
  • A1 bis C2+P2 Peak 2 280 76 580 41 310 61
  • Peak 1 Percentage of native protein (Insulin) after stabilization (days) at 37O obtained by DLS. Peak 1 corresponds to the hydrodynamic diameter of the native protein and peaks 2 to the protein aggregates. For each peak the diameter (nm) and the percentage of light intensity is mentioned.
  • Tests were performed to determine the necessary forces to move a piston inside a treated or untreated syringe barrel. These tests were performed using a LLOYD-CB190 tensile testing machine dynamometer using NEXYGEN operating software, according to two test protocols outlined briefly below.
  • Activation Gliding Force (AGF) tests were applied on containers filled with 1 ml_ of demineralised water and each plugged with one piston. Each container-piston system was tested 24 times in order to ensure the reproducibility and to validate the results. To prepare the 24 syringes for a system, and particularly to insert the piston in the container, a SPV machine was used.
  • the friction force S is the force required, under dynamic conditions, to move the piston in the container.
  • the friction force S is measured half way of the piston travel. In order to measure the friction force S, the barrel was filled with water,
  • the friction force F is the force required, again in dynamic mode, to move the piston when it reaches the end of its travel in the container. Just like the friction force S, the friction force F is measured with a container initially filled with water.
  • A1 C1 +P2 3.2 ( ⁇ 0.6) 4.6 ( ⁇ 0.2) 4.6 ( ⁇ 0.3)
  • Bi layer A2 P2 2.9 ( ⁇ 0.2) 4.5 ( ⁇ 0.2) 4.6 ( ⁇ 0.2)
  • the friction force in the static mode was the lowest on the reference R2 and after 5s of plasma treatment (typically less than 2.5 N on P1 ), intermediary after 15 s of treatment (3.5N on P2) and reached 6N after 30s of treatment on P3.
  • the sustainable force was less than 5N for the reference R2 or after 5 or 15 s of plasma treatment on P1 and P2 whereas it grew up to 5.1 N or more than 6N after 30s of treatment on P3, P4 and P5.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • Metallurgy (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Anesthesiology (AREA)
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  • Heart & Thoracic Surgery (AREA)
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  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Infusion, Injection, And Reservoir Apparatuses (AREA)

Abstract

La présente invention a pour objet une seringue destinée à être remplie avec une préparation pharmaceutique, caractérisée en ce que l'effet barrière pour tous les éléments cationiques est inférieur ou égal à 250 ng/cm2, de préférence inférieur ou égal à 200 ng/cm2, de manière davantage préférée inférieur ou égal à 150 ng/cm2. La présente invention concerne également un procédé pour préparer une telle seringue comprenant les étapes consistant à : • créer une couche huileuse interne homogène et continue à l'intérieur d'une seringue, • exposer ladite couche huileuse interne à un gaz plasma oxydant, ladite huile étant une huile non réactive.
PCT/IB2008/054475 2007-10-22 2008-08-20 Revêtement de surface pour empêcher la lixiviation cationique WO2009053947A2 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US99992107P 2007-10-22 2007-10-22
US60/999,921 2007-10-22
US99997507P 2007-10-23 2007-10-23
US60/999,975 2007-10-23
US17007P 2007-10-24 2007-10-24
US61/000,170 2007-10-24

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WO2009053947A2 true WO2009053947A2 (fr) 2009-04-30
WO2009053947A3 WO2009053947A3 (fr) 2009-07-09

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FR2962139A1 (fr) * 2010-07-02 2012-01-06 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide.
FR2962136A1 (fr) * 2010-07-02 2012-01-06 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide.
WO2012001328A3 (fr) * 2010-07-02 2012-03-29 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide
WO2012001326A3 (fr) * 2010-07-02 2012-03-29 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide
US8512796B2 (en) 2009-05-13 2013-08-20 Si02 Medical Products, Inc. Vessel inspection apparatus and methods
WO2013178647A1 (fr) * 2012-05-29 2013-12-05 Becton Dickinson France Revêtement lubrifiant et dispositif d'injection médical comprenant un tel revêtement
US8802603B2 (en) 2010-06-17 2014-08-12 Becton, Dickinson And Company Medical components having coated surfaces exhibiting low friction and low reactivity
US20140341883A1 (en) * 2013-04-24 2014-11-20 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
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