EP2958956A1 - Support polymere de distribution de substance naturellement cristalline et procédé d'obtention - Google Patents

Support polymere de distribution de substance naturellement cristalline et procédé d'obtention

Info

Publication number
EP2958956A1
EP2958956A1 EP14713147.8A EP14713147A EP2958956A1 EP 2958956 A1 EP2958956 A1 EP 2958956A1 EP 14713147 A EP14713147 A EP 14713147A EP 2958956 A1 EP2958956 A1 EP 2958956A1
Authority
EP
European Patent Office
Prior art keywords
polymer
support
mixture
solvent
crystalline substance
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Withdrawn
Application number
EP14713147.8A
Other languages
German (de)
English (en)
French (fr)
Inventor
Rene Chelle
Arnaud Vilbert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AB7 Innovation SAS
Original Assignee
AB7 Innovation SAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by AB7 Innovation SAS filed Critical AB7 Innovation SAS
Publication of EP2958956A1 publication Critical patent/EP2958956A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
    • A01K27/00—Leads or collars, e.g. for dogs
    • A01K27/007—Leads or collars, e.g. for dogs with insecticide-dispensing means
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • C08J3/2053—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the additives only being premixed with a liquid phase
    • 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
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers
    • 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
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers

Definitions

  • the present invention relates to the production of a naturally crystalline substance distribution support in the solubilized state without crystallization on the surface.
  • alkaloids particularly pose a problem of crystallization related to temperature and concentration conditions. This is the case, for example, for caffeine which has to be low in gelled medium in order to be applicable to the skin.
  • Some drugs are also in this case as ibuprofen which must be formulated to 5% especially in a gel for a cutaneous application.
  • the gel preserves a crystallization of the active ingredient on the skin, which would hinder its transdermal passage.
  • Said support polymer may be, without presenting an exhaustive list, in the form of necklace, bracelet, earplug, medallion or patch. This phenomenon makes it difficult to produce controlled dispensing devices of above-mentioned substances from the solid supports which are impregnated therewith.
  • the patent EP0539295 (USSEL-UCLAF - 22/10/1992) describes a Deltamethrin controlled release device incorporated in a polyvinyl chloride (PVC) vinyl polymer matrix.
  • PVC polyvinyl chloride
  • a polymer-miscible liquid plasticizer and triphenyl phosphate as a carrier for the active agent are used.
  • the asset is mixed with its vehicle which allows its intra-matrix migration to the surface of the device. But in the end, there is always recrystallization of the asset on the surface of the device.
  • This system involving a combination of two pairs that must be compatible, formed by a polymer and a plasticizer compatible on the one hand and an asset in liquid or solid form and its vehicle on the other hand, allows to incorporate and maintain said asset in a polymeric support.
  • This is a technical solution that has been widely used in many fields for the distribution of a crystalline active ingredient or a combination of crystalline active agents in a long-term controlled manner from a polymeric support.
  • EP0052411 B1 ZOECON CORPORATION - 10/04/1981
  • EP0090446 A2 International Shell Research - 15/03/1983
  • EP0436428 B1 VIRBAC LABORATORIES - 21/12/1990
  • EP0537998 B1 MCK & Co., Inc. - 14/10/1992
  • EP0539295 B1 ROUSSEL-UCLAF - 22/10/1992
  • EP0542080 B1 BAYER AG - 02/11/1992
  • EP0671123 B1 ZOBELE INDUSTRY CHIMICHE SpA - 11 / 03/1994
  • EP1022944 B1 AKZO NOBEL NV - 16/06/1998).
  • the resins and polymers used for producing the devices described in these patents are various and often of linear structure. Many of them can not be shaped without the presence of a compatible plasticizer. Because they are not able to incorporate assets in the matrices formed to deliver these assets in a controlled long-term, it is necessary to add asset vehicles to them.
  • vinyl polymers preferably polyvinyl chloride and its copolymers with vinyl acetate and vinylidene dichloride, of polypropylene, of polyamide, of polycarbonates, polystyrene, polyesters such as cellulose acetate, polylactide, cellophane and the mixture of all these polymers, polyethylene, copolymers of ethylene and vinyl acetate, polyester-based polyurethane and polyether, or copolymers of glycol ether / ester terephthalate and other thermoplastic elastomers.
  • vinyl polymers preferably polyvinyl chloride and its copolymers with vinyl acetate and vinylidene dichloride, of polypropylene, of polyamide, of polycarbonates, polystyrene, polyesters such as cellulose acetate, polylactide, cellophane and the mixture of all these polymers, polyethylene, copolymers of ethylene and vinyl acetate, polyester-based polyurethane and polyether, or copolymers of glyco
  • plasticizers intended for the functional adaptation of the physical characteristics of the polymers, are chosen from phosphoric acid esters, phthalic esters commonly called phthalates, adipic acids, etc. Phthalates are substances currently banned or in the process of being banned for many applications because of their level of toxicity. Other plasticizers migrate into the matrix and thus present a risk of passage on the skin and even through the skin.
  • Asset vehicles have the function of storing the asset and promoting its migration within the polymer matrix in which said vehicles are incorporated. This requires that there is good compatibility between the vehicle and the polymer matrix.
  • Asset vehicles are generally selected from mineral fillers, such as triphenyl phosphate. It should be noted that certain charges can weaken or modify the physical characteristics of the polymer matrix.
  • the polymer matrix in the form of microspheres, is a copolymer of polyvinyl alcohol and ethylene which must be anionic. This last characteristic is obtained by the addition of buffered sulfonate, phosphonate or carboxylate groups.
  • the process claimed in this application is complex to achieve, which is a major drawback because it increases the cost of the product. It can also cause environmental problems.
  • the method of the present invention overcomes the disadvantages of the prior art. It makes it possible to achieve more simply the incorporation without vehicle of naturally crystalline substances in a polymer support whose matrix is shaped, without plasticizer. It is based on the active polymer technology developed by the applicant and embodied inter alia by the patent FR 2 901 72 B1 (8/01/2006) entitled "Method of cold loading of an active ingredient in a polymer matrix".
  • solvent mixture refers to the mixture of a solvent with a cosolvent which makes it possible to obtain complete and permanent solubilization of the naturally crystalline substance.
  • naturally crystalline substance means a naturally crystalline active agent or a mixture of several naturally crystalline active agents or a mixture of at least one naturally crystalline active agent with at least one naturally noncrystalline active agent.
  • polymer blend refers to the combination of at least two polymers in a defined ratio to form a polymer matrix for obtaining a polymer support according to conventional techniques of plastics.
  • An object of the invention is a method for the non-carrier loading of naturally crystalline substance solubilized by a solvent mixture in a lipophilic medium in a mixture of granulated polymer intended to form, without plasticizer, a polymeric support of controlled distribution of long duration in the state stable solubilized of said substance without crystallization on the surface of said support.
  • the process is characterized in that the solubilized state of the naturally crystalline substance is surprisingly obtained by using a solvent mixture composed of an oxygenated solvent of dibasic fatty acid esters. which is associated with an oxygenated methylenic cosolvent.
  • the solvent is a mixture of dibasic esters of methylenic fatty acids. It has the advantage of being an oxygenated solvent with low vapor pressure, so virtually non-volatile. Its efficiency Solvent naturally occurring substances is effective from the temperature of 45 ° C.
  • the cosolvent is an oxygenated methylenic solvent which is dimethylisosorbide (DMI) which is a non-toxic "green” solvent.
  • DMI dimethylisosorbide
  • Its dissolving effectiveness of naturally crystalline substances is effective even at room temperature. It has a drawback which is its high cost which can limit its use in large quantities.
  • a good emollient it is chosen in the present invention, at a limited rate, to associate with the solvent character that control of a possible transdermal passage of solubilized assets.
  • the solvent mixture makes it possible to unexpectedly increase the concentration threshold of naturally crystalline substances for better dissolution. This is for example a maximum of 20% by weight of cold solution of Deltamethrin, without recrystallization in the active solution even at low temperature. Caffeine is stably dissolved in said solvent mixture at 6% by weight of solution and Propoxur at 56%, still by weight of solution.
  • Said solvent mixture according to the invention advantageously leads to a reduction in the order of 30% to 50% of the amount of asset to be incorporated in the support compared to the previous devices while allowing to achieve at least the same results of active efficiency, otherwise better results.
  • This advantageous characteristic is provided by the solubilized state of the asset and the emollient nature of the cosolvent.
  • the oxygenated solvent of dibasic esters of methylenic fatty acids according to the invention does not provide these advantages.
  • the oxygenated methylenic solvent chosen cosolvent, taken alone also did not achieve the objectives.
  • the ratio of the two components of the solvent mixture in the solvent / cosolvent order which makes it possible to achieve the objectives according to the invention varies between 38/62 and 90/10, preferably between 45/55 and 75/25.
  • the solubilized naturally crystalline substances can be pyrethroid group insecticides and pesticides (eg Deltamethrin), formamidines (eg Amitraz) and carbamates (eg Propoxur) or a mixture of these, or cosmetics of the group of alkaloids (Ex. Caffeine), or drugs (Ex Ibuprofen).
  • At least one vegetable oil chosen from coconut oil, sweet almond oil, lemon is supplied to the solution of naturally crystalline substance. macadamia oil or any other vegetable oil accepted in cosmetics or pharmacy.
  • thermoplastic polymers used in the context of the invention are chosen from polyolefins and polyurethane elastomers.
  • the state of permanent noncrystallization at the surface of the polymer support for dispensing naturally crystalline substances is only ensured when said substances are solubilized in a solvent mixture composed of an oxygenated solvent of dibasic esters of methylenic fatty acids. and an oxygenated methylenic cosolvent to form an active lipophilic solution by adding vegetable oil, which active lipophilic solution is incorporated into a polymer mixture composed of a polyether block amide (PEBA) and a thermoplastic polyurethane elastomer (TPU) .
  • PEBA polyether block amide
  • TPU thermoplastic polyurethane elastomer
  • PEBA taken by itself, does not make it possible to permanently ensure the non-crystallization on the surface of the device of the naturally crystalline substance incorporated therein in the solubilized state. Similarly the TPU taken alone, also does not achieve this objective of the invention.
  • this objective according to the invention is achieved when the ratio of the polymer mixture in the order PEBA / TPU varies between 80/20 and 40/60, preferably between 55/45 and 45/55.
  • technical adjuvants may be provided for the shaping of the support, for example dyes and / or structural polymers intended for the adaptation of mechanical characteristics such as flexibility of said support according to its destination, as well as other adjuvants not interfering with the state of non-permanent crystallization on the surface of said support.
  • Said support can be shaped as a collar, a medallion, a pet earplate, a bracelet, a patch, a wafer, a polymer block or any other asset distribution device. It is shaped by any of the techniques of plastics known to those skilled in the art.
  • the support has the capacity to store between 0.25% and 20% by weight of naturally crystalline substance depending on the nature of said substance and the destination of said support.
  • the method of loading without a vehicle of naturally crystalline substance solubilized by a solvent mixture in a lipophilic medium in a mixture of granulated polymers intended to form, without plasticizer, a polymer support of long-term controlled distribution of said substance to the stable solubilized state said method ensuring non-permanent crystallization on the surface of said support is carried out as follows: a) Preparation of the solvent mixture composed of an oxygenated solvent of dibasic esters of methylenic fatty acids and an oxygenated methylene cosolvent ;
  • PEBA polyether block amide
  • TPU thermoplastic polyurethane elastomer
  • the carrier naturally crystalline substance in the solubilized state obtained by the process of the invention is necessarily placed in a protective packaging in a sealed package and preferably individually for storage prior to use.
  • Oxygen solvent dibasic esters of methylenic fatty acids marketed by DOW HALTERMANN under the trademark ESTASOL ® .
  • DMI dimethyl isosorbide
  • PEBA Granules amide block polyether polymers
  • thermoplastic polyurethane polymer (TPU) based GAZECHIM ether sold by under the trademark PEARLTHANE ® D15N70.
  • Step 1 Preparation of the active solution by:
  • Step 2 Incorporation of active solution in the granulated polymer PEBAX ® 2533 SA 01 J PEARLTHANE® D15N70
  • the horizontal mixer DRAIS of 20L is preheated to 95 ° C;
  • Step 3 Formatting by injection molding medallion intended to be attached to a collar
  • the steel mold mounted on said press has four indentations in the form of a medallion.
  • the temperature diagram of the barrel, from the hopper to the nozzle is as follows: 105 ° C, 125 ° C, 125 ° C, 25%.
  • Deltamethrin medallions obtained weigh about 10 g and contain 2.4% Deltamethrin, 40% less than the devices of the prior art. They have an oval main body with a tongue on one side and carrying a loop on the other.
  • Deltamethrin medallions obtained are packaged and stored at room temperature for 12 months. It is noted that there is no recrystallization of Deltamethrin on the surface of the medallion, proof that Deltamethrin remained in the solubilized state.
  • the medallion is fixed and mounted on a dog collar by placing it in close contact either with the coat or directly with the skin of the animal.
  • Said medallion can effectively fight against ectoparasites of all kinds for a long period of up to several months.
  • olive oil is known to determine the amount of solubilized non-volatile active ingredient released in a lipophilic composition.
  • the choice of olive oil is is justified by the fact that its composition is similar to the structure of the lipid layer of the animal epidermis.
  • this experimental model makes it possible to quantify the amount of Deltamethrin released from the Deltamethrin medallion obtained according to the process according to the invention as well as from a commercial necklace, SCALIBOR ® with Deltamethrin.
  • Three medallions loaded with 4% of Deltamethrin and weighing each about 10 g are placed in a crystallizer of 120 mm diameter into which 200 ml of olive oil are introduced.
  • the medium is stirred at 250 rpm using a magnetic bar placed in each crystallizer.
  • a standard solution of 40 mg / l of Deltamethrin, the purity of which is known, is carried out under the same conditions using olive oil.
  • the amount of Deltamethrin released is determined by High Pressure Liquid Chromatography (HPLC).
  • HPLC High Pressure Liquid Chromatography
  • a PROVIDER ICS ® chromatograph equipped with a model 2250 pump and a PRONTOSIL® 120-5-C18 column with dimensions of 250 mm x 3.0 mm is available.
  • Samples are taken at times T0, T1, T2, T3, T7, T10, T17, T31, T45, T59, and T73. The unit of time is in day. After each sample, each sample is analyzed by HPLC to determine the amount of Deltamethrin released into the olive oil.
  • EXAMPLE 3 Preparation of a caffeine patch to fight against orange peel in humans.
  • caffeine Because of its hydrophilic property, it is well known that caffeine is generally formulated in cream or in gel. Moreover, the largest number of existing caffeine products on the market are creams.
  • the preparation of a caffeine patch according to the invention takes place in three stages.
  • the preparation of the active solution passes through the solubilization of caffeine in the solvent mixture in an oxygen solvent ratio of dibasic esters of methylenic fatty acids / oxygenated methylenic solvent of 3/5.
  • the mixture is stirred for 20 minutes until the active solution becomes clear. Said active solution is stable, ie the caffeine does not recrystallize.
  • Step 2 Incorporation of the active solution. in the PEBAX ® / PEARLTHANE ® D15N70 polymer blend at a ratio of 1/2
  • the active solution is allowed to become incorporated in the polymer granules until they become dry and not sticky, for at least 15 minutes;
  • the lipophilic caffeine-loaded polymer granules thus obtained are recovered.
  • Step 3 Patch shaping to be applied on the thighs.
  • the same material as in example 1 is available.
  • the mounted molds have four parallelogram-shaped impressions 7 cm long by 4 cm wide and 2 mm deep. .
  • the injection temperature diagram from the hopper to the nozzle, is as follows: 105 ° C, 125 ° C, 125 ° C, 25%.
  • the patches with 0.6% caffeine slimming effect obtained are very flexible.
  • the MULTIFLEX G00A41 provides these patches the essential flexibility. They can be applied directly on the skin at the thighs to fight against orange peel. Said patches may be associated with a panty for a more intimate application against the skin.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Medicinal Chemistry (AREA)
  • Toxicology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Animal Husbandry (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)
EP14713147.8A 2013-02-15 2014-02-10 Support polymere de distribution de substance naturellement cristalline et procédé d'obtention Withdrawn EP2958956A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1300330A FR3002232B1 (fr) 2013-02-15 2013-02-15 Support polymere de distribution de substance naturellement cristalline et procede d'obtention
PCT/FR2014/000032 WO2014125175A1 (fr) 2013-02-15 2014-02-10 Support polymere de distribution de substance naturellement cristalline et procédé d'obtention

Publications (1)

Publication Number Publication Date
EP2958956A1 true EP2958956A1 (fr) 2015-12-30

Family

ID=48613694

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14713147.8A Withdrawn EP2958956A1 (fr) 2013-02-15 2014-02-10 Support polymere de distribution de substance naturellement cristalline et procédé d'obtention

Country Status (8)

Country Link
US (1) US9669100B2 (es)
EP (1) EP2958956A1 (es)
BR (1) BR112015019533A2 (es)
CA (1) CA2899669A1 (es)
CL (1) CL2015002264A1 (es)
FR (1) FR3002232B1 (es)
MX (1) MX2015010420A (es)
WO (1) WO2014125175A1 (es)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9988809B2 (en) 2016-10-06 2018-06-05 Technologie 2000 Inc. Construction block anchoring system
US10202755B2 (en) 2016-10-06 2019-02-12 Technologie 2000 Inc. Construction block anchoring system

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Publication number Priority date Publication date Assignee Title
US4348321A (en) 1980-11-14 1982-09-07 Zoecon Corporation Recrystallization of phosmet
CA1185173A (en) 1982-03-25 1985-04-09 Johannes T. Bouman Slow release pesticidal composition and control device, its preparation and its use
FR2656526B1 (fr) * 1990-01-02 1994-10-28 Virbac Sa Laboratoires Dispositif a liberation controlee et procede de preparation.
US5411737A (en) 1991-10-15 1995-05-02 Merck & Co., Inc. Slow release syneresing polymeric drug delivery device
MX9206034A (es) * 1991-10-24 1993-05-01 Roussel Uclaf Sistema para el control de plagas.
DE4137273A1 (de) 1991-11-13 1993-05-19 Bayer Ag Wirkstoffhaltige formkoerper auf basis thermoplastisch verarbeitbarer elastomerer polyether-blockamide, verfahren zu ihrer herstellung und verwendung zur kontrolle von schaedlingen
EP0671123B1 (en) * 1994-03-11 2000-06-14 ZOBELE INDUSTRIE CHIMICHE S.p.A. Insecticide formulation with solid support
FR2746261B1 (fr) 1996-03-19 1998-05-07 Virbac Sa Composition insecticide et procede de preparation
EP0885563A1 (en) 1997-06-18 1998-12-23 Hoechst Roussel Vet S.A. Repellent pest control system
US20080305176A1 (en) * 2006-01-24 2008-12-11 Biocompatibles Uk Limited Process For Loading Polymer Particles With Drug
FR2901172B1 (fr) 2006-05-18 2010-10-08 Ab7 Ind Procede de chargement a froid d'un actif dans une matrice. polymere
EP2377399A1 (de) 2010-04-15 2011-10-19 Bayer Cropscience AG Insektizidhaltiges Polymermaterial

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
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See also references of WO2014125175A1 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9988809B2 (en) 2016-10-06 2018-06-05 Technologie 2000 Inc. Construction block anchoring system
US10202755B2 (en) 2016-10-06 2019-02-12 Technologie 2000 Inc. Construction block anchoring system

Also Published As

Publication number Publication date
MX2015010420A (es) 2016-05-05
BR112015019533A2 (pt) 2017-07-18
CL2015002264A1 (es) 2016-02-19
WO2014125175A1 (fr) 2014-08-21
US20150374829A1 (en) 2015-12-31
FR3002232A1 (fr) 2014-08-22
FR3002232B1 (fr) 2015-03-27
CA2899669A1 (fr) 2014-08-21
US9669100B2 (en) 2017-06-06

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