WO2013115739A1 - Procédé de préparation de formulations contenant du natéglinide et de l'acide lipoïque - Google Patents

Procédé de préparation de formulations contenant du natéglinide et de l'acide lipoïque Download PDF

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Publication number
WO2013115739A1
WO2013115739A1 PCT/TR2013/000048 TR2013000048W WO2013115739A1 WO 2013115739 A1 WO2013115739 A1 WO 2013115739A1 TR 2013000048 W TR2013000048 W TR 2013000048W WO 2013115739 A1 WO2013115739 A1 WO 2013115739A1
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WO
WIPO (PCT)
Prior art keywords
formulations
tablet
nateglinide
lipoic acid
alpha
Prior art date
Application number
PCT/TR2013/000048
Other languages
English (en)
Inventor
Mahmut Bilgic
Original Assignee
Mahmut Bilgic
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 Mahmut Bilgic filed Critical Mahmut Bilgic
Publication of WO2013115739A1 publication Critical patent/WO2013115739A1/fr

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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
    • A61K9/20—Pills, tablets, discs, rods
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Definitions

  • the present invention relates to a method used for production of pharmaceutical formulations comprising the meglitinide derivative agent nateglinide and alpha-lipoic acid as the active agents.
  • the meglitinide derivative agents also known as glinides, are effective on insulin secretion.
  • Nateglinide, repaglinide, mitiglinide can be given as examples to some agents belonging to this group.
  • Alpha-lipoic acid is an anti-oxidant agent.
  • the studies conducted have shown that alpha-lipoic acid prevents limb dysfunction, cardiovascular diseases, migraine, age-dependent decline in mental activities and progression of Alzheimer's disease.
  • tablet dosage forms are the most frequently used dosage forms among oral formulations.
  • physical characteristics of any kind of dosage form are directly related to resistance in storage conditions, dissolution and bioavailability of the dosage form in terms of pharmaceutical technology.
  • Tablet hardness is an important physical parameter in pharmaceutical tablet formulations and it relates to resistance of tablets against storage, carriage, coating and corrosion-breakage before use. The tablets having low hardness are more subjected to corrosion, disintegration or breakage and this causes,
  • the present invention relates to a method used in production of the formulations comprising nateglinide and alpha-lipoic acid as the active agents.
  • the production method of the present invention is composed of the steps of preparing alpha- lipoic acid and nateglinide separately and combining the formulations obtained this way.
  • a characteristic feature of the production method of the present invention is that said method is implemented by preparing alpha-lipoic acid and nateglinide separately and combining the obtained formulations.
  • alpha-lipoic acid is prepared by compacting process in the production method of the present invention.
  • Compacting process is implemented by compressing alpha- lipoic acid under a specific pressure.
  • Use of a compression force in the range of 3 kN to 50 kN in compacting process has contributed to the solution of tablet hardness problem which is tried to be solved by the present invention and optimum tablet hardness is provided in the formulations prepared by performing compacting process under this compression force without the need for any additional process.
  • a characteristic feature of the method preferred for production of the formulations of the present invention is that nateglinide is subjected to granulation process with at least one excipient in said production method.
  • the present invention relates to a method that shall be used in production of the formulations comprising nateglinide and alpha-lipoic acid as the active agents, said method is characterized by
  • the production method of the present invention is composed of the following steps:
  • the inventors have found that the most excellent mechanical tablet resistance and the most appropriate dissolution rate and therefore the highest bioavailability are obtained with the tablet formulations, wherein the two active agents are formulated by using different methods and then combined, and tablet hardness value is in the range of 3 kP to 50 kP.
  • tablet formulations to be obtained by the production method of the present invention comprise nateglinide and alpha lipoic acid as the active agents and at least one pharmaceutically acceptable excipient and tablet hardness value is in the range of 3 kP to 50 kP.
  • tablette formulations to be obtained by the production method of the present invention comprise nateglinide and alpha- lipoic acid as the active agents and at least one pharmaceutically acceptable excipient and tablet hardness value is in the range of 4 kP to 40 kP.
  • tablette formulations to be obtained by the production method of the present invention comprise nateglinide and alpha- lipoic acid as the active agents and at least one pharmaceutically acceptable excipient and tablet hardness value is in the range of 5 kP to 30 kP.
  • the method for preparation of the formulations of the present invention comprises formulating the active agent with the suitable excipient composition and compressing said formulation in tablet form under a suitable compression force.
  • a characteristic feature of the tablet formulations of the present invention is that said formulations comprise a meglinitide derivative agent and alpha-lipoic acid as the active agents and at least one pharmaceutically acceptable excipient and tablet compression force used for compressing said formulations in tablet form is in the range of 3 kN to 50 kN.
  • a characteristic feature of the tablet formulations of the present invention is that said formulations comprise a meglinitide derivative agent and alpha-lipoic acid as the active agents and at least one pharmaceutically acceptable excipient and tablet compression force used for compressing said formulations in tablet form is in the range of 4 kN to 45 kN.
  • tablet formulations of the present invention comprise a meglinitide derivative agent and alpha-lipoic acid as the active agents and at least one pharmaceutically acceptable excipient and tablet compression force used for compressing said formulations in tablet form is in the range of 5 kN to 40 kN.
  • Nateglinide comprised in the pharmaceutical formulations to be obtained by the production method of the present invention can be structurally in the form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers; and/or in amorphous, crystalline forms or a combination thereof in terms of polymorphic structure or combinations thereof.
  • Alpha-lipoic acid comprised in the pharmaceutical formulations to be obtained by the production method of the present invention can be in the form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers; and/or in any of the polymorphic forms such as amorphous, crystalline forms or combinations thereof.
  • the pharmaceutical formulations comprising nateglinide and alpha lipoic acid to be obtained by the production method of the present invention can be prepared in any dosage forms of tablet, effervescent tablet, effervescent granule, effervescent dry powder, film coated tablet, enterically coated tablet, dry powder, granule, capsule, prolonged release tablet, modified release tablet, delayed release tablet, orodispersible tablet, chewable tablet.
  • the pharmaceutical formulations comprising nateglinide and alpha lipoic acid can be combined together in one of the abovementioned dosage forms though in the case that nateglinide and alpha-lipoic acid are stored in different dosage forms, said formulations can also be in any of these dosage forms.
  • the formulations comprising the combination of the present invention can be in any abovementioned dosage forms or combinations thereof or in a treatment package comprising this combination.
  • the present invention relates to pharmaceutical formulations comprising pharmaceutically effective amounts of nateglinide and alpha-lipoic acid and at least one pharmaceutically acceptable excipient and production method thereof.
  • the pharmaceutical formulations comprising nateglinide and alpha-lipoic acid to be obtained by the production method of the present invention can comprise various excipients in addition to the active agents nateglinide and alpha-lipoic acid.
  • the pharmaceutical formulations comprising nateglinide and alpha-lipoic acid to be obtained by the production method of the present invention comprise at least one excipient selected from a group comprising disintegrant, diluent, lubricant, glidant, binder, effervescent couple comprising at least one acidic agent and at least one basic agent, colouring agent, pH regulating agent, surfactant, stabilizing agent, sweetener and/or taste regulating agent, flavouring agent in addition to the active agents.
  • the disintegrant that can be used in the pharmaceutical formulations to be obtained by the production method of the present invention can be selected from a group comprising carboxymethyl cellulose, carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, croscarmellose sodium, croscarmellose sodium, crospovidone, hydroxypropyl cellulose, microcrystalline cellulose, methylcellulose, chitosan, starch, sodium starch glycolate.
  • the diluent that can be used in the pharmaceutical formulations to be obtained by the production method of the present invention can be selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, maltitol, maltodextrin, maltose, mannitol, simethicone, sorbitol, starch, sodium chloride, sucrose, talc, xylitol.
  • the lubricant that can be used in the pharmaceutical formulations to be obtained by the production method of the present invention can be selected from a group comprising calcium stearate, magnesium stearate, polyethylene glycol, sodium benzoate, potassium benzoate, sodium lauryl sulphate, talc, stearic acid, zinc stearate.
  • the glidant that can be used in the pharmaceutical formulations to be obtained by the production method of the present invention can be selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, magnesium trisilicate, talc.
  • the binder that can be used in the pharmaceutical formulations to be obtained by the production method of the present invention can be selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methyl cellulose, povidone, starch.
  • the pharmaceutical formulations to be obtained by the production method of the present invention can comprise nateglinide in the range of 0.1 to 99% by weight, preferably in the range of 1 to 98% by weight, more preferably in the range of 5 to 95% by weight, for instance in the range of 5, 10, 15, 20, 25, 30 % to 35, 40, 45, 50, 55, 60, 65, 70, 80, 90 % by weight.
  • the pharmaceutical formulations to be obtained by the production method of the present invention can comprise alpha-lipoic acid in the range of 0.1 to 99% by weight, preferably in the range of 1 to 98% by weight, more preferably in the range of 5 to 95% by weight, for instance in the range of 5, 10, 15, 20, 25, 30% to 35, 40, 45, 50, 55, 60, 65, 70, 80, 90% by weight.
  • the pharmaceutical formulations to be obtained by the production method of the present invention can comprise nateglinide in the range of 0.01 mg to 500 mg, preferably in the range of 0.1 mg to 300 mg, more preferably in the range of 0.5 mg to 250 mg.
  • the pharmaceutical formulations to be obtained by the production method of the present invention can comprise alpha-lipoic acid in the range of 100 mg to 1500 mg, preferably in the range of 150 mg to 1200 mg, more preferably in the range of 200 mg to 1000 mg.
  • the pharmaceutical formulations comprising nateglinide and alpha-lipoic acid to be obtained by a production method of the present invention can optionally comprise a third active agent in addition to nateglinide and alpha-lipoic acid.
  • the third active agent can be selected from antacid, anticholinergic, antispasmodic, antiemetic, antidiabetic, antipropulsive, antiallergic, antidiarrheal, antiobesity, antithrombotic, antifibrinolytic, antianemic, antihypertensive, antifungal, antipruritic, antipsoriatic, antibiotic, antiseptic, antiacne, antibacterial, antimycotic, antiviral, antineoplastic, antiarrhythmic, antiadrenergic, antiepileptic, anti- parkinson, antiprotozoal, anthelmintic, anti-inflammatory, diuretic, laxative, sulphonamide, imidazole, corticosteroid,
  • the pharmaceutical formulations comprising nateglinide and alpha-lipoic acid to be obtained by the production method of the present invention comprise preferably an anti-diabetic agent; an agent selected from a group comprising meglinitide, thiazolidinedione, sulfonylurea, peptide analogue, biguanide, organosulfur compound, more preferably voglibose, acarbose, miglitol, nateglinide, repaglinide, rosiglitazone, pioglitazone, rivoglitazone, troglitazone, rosiglitazone maleate, pioglitazone hydrochloride, tolbutamide, acetohexamide, glibenclamide, chlorpropamide, clopamide, glibornuride, glipizide, gliquidone, glyburide, glimepiride, gliclazide, vildaglipt
  • the pharmaceutical formulation or formulations obtained can be formed into any abovementioned dosage forms.
  • the tablets obtained can be treated with film coating agents, for instance sugar based coating agents, water soluble film coating agents, enteric coating agents, delayed release coating agents or coating formulations comprising a combination thereof.
  • Saccharose can be used singly or optionally with any of the agents such as talc, calcium, carbonate, calcium phosphate, gelatine, gum arabic, polyvinylpyrrolidone and pullulan or a combination thereof as the sugar based coating agent.
  • the water-soluble film coating agent can be selected from cellulose derivatives such as hydroxypropyl cellulose, hydroxypropyl methylcellulose, hydroxyethyl cellulose, methyl hydroxyethyl cellulose and sodium carboxymethyl cellulose; synthetic polymers such as polyvinyl acetal diethyl aminoacetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone and polysaccharides such as pullulan or combinations thereof.
  • cellulose derivatives such as hydroxypropyl cellulose, hydroxypropyl methylcellulose, hydroxyethyl cellulose, methyl hydroxyethyl cellulose and sodium carboxymethyl cellulose
  • synthetic polymers such as polyvinyl acetal diethyl aminoacetate, aminoalkyl methacrylate copolymers and polyvinylpyrrolidone and polysaccharides such as pullulan or combinations thereof.
  • the enteric coating agents can be selected from cellulose derivatives such as hydroxypropyl methyl cellulose phthalate, hydroxypropyl methylcellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate phthalate; acrylic acid derivatives such as methacrylic acid copolymer L, methacrylic acid copolymer LD and methacrylic acid copolymer S and natural substances such as shellac or combinations thereof.
  • cellulose derivatives such as hydroxypropyl methyl cellulose phthalate, hydroxypropyl methylcellulose acetate succinate, carboxymethyl ethyl cellulose, cellulose acetate phthalate
  • acrylic acid derivatives such as methacrylic acid copolymer L, methacrylic acid copolymer LD and methacrylic acid copolymer S and natural substances such as shellac or combinations thereof.
  • the delayed release coating agents can be selected from cellulose derivatives such as ethyl cellulose; acrylic acid derivatives such as aminoalkyl methacrylate copolymer RS, ethyl acrylate-methyl methacrylate copolymer emulsion or combinations thereof.
  • the pharmaceutical formulation to be obtained by the production method of the present invention can be used in the treatment of type 2 diabetes.
  • EXAMPLE 1 The pharmaceutical formulations comprising the combination of nateglinide and alpha-lipoic acid
  • the granulation solution is prepared by mixing nateglinide and the diluent, it is granulated with the granulation solution comprising the binder and the solvent, the granules are dried and sieved,
  • Alpha-lipoic acid is loaded to compacting machine and it is sieved after the compacting process, then it is mixed with the lubricant,
  • the mixture comprising nateglinide and the mixtures comprising alpha-lipoic acid are loaded to tablet compression machine separately and tablet compression is performed, The tablets obtained are coated with the coating agents.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne un procédé utilisé pour la préparation de formulations pharmaceutiques contenant des agents dérivés du méglitinide, et de l'acide alpha-lipoïque.
PCT/TR2013/000048 2012-01-31 2013-01-31 Procédé de préparation de formulations contenant du natéglinide et de l'acide lipoïque WO2013115739A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201201096 2012-01-31
TR2012/01096 2012-01-31

Publications (1)

Publication Number Publication Date
WO2013115739A1 true WO2013115739A1 (fr) 2013-08-08

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PCT/TR2013/000048 WO2013115739A1 (fr) 2012-01-31 2013-01-31 Procédé de préparation de formulations contenant du natéglinide et de l'acide lipoïque
PCT/TR2013/000049 WO2013115740A1 (fr) 2012-01-31 2013-01-31 Combinaison synergique contenant un dérivé de méglitinide et de l'acide lipoïque

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PCT/TR2013/000049 WO2013115740A1 (fr) 2012-01-31 2013-01-31 Combinaison synergique contenant un dérivé de méglitinide et de l'acide lipoïque

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EP (1) EP2809316A1 (fr)
WO (2) WO2013115739A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11986460B2 (en) 2018-11-26 2024-05-21 The Procter & Gamble Company Solid pharmaceutical preparation containing lipoic acid and use thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140127296A1 (en) * 2012-11-05 2014-05-08 Kenneth John Tibbs Pharmaceutical preparation and method for treatment of diabetes
CN109864974A (zh) * 2017-12-01 2019-06-11 王辉 马来酸罗格列酮分散片及其制备方法

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WO2002072146A2 (fr) * 2001-03-12 2002-09-19 Novartis Ag Combinaison de composes organiques
EP1283054A1 (fr) * 2000-03-17 2003-02-12 Ajinomoto Co., Inc. Medicaments permettant de traiter les complications du diabete et des neuropathies et utilisation de ces medicaments
EP1334721A1 (fr) * 2000-10-24 2003-08-13 Ajinomoto Co., Inc. Preparations de medicament contenant du nateglinide
WO2005020979A1 (fr) * 2003-09-03 2005-03-10 Ranbaxy Laboratories Limited Procede de preparation de compositions pharmaceutiques a base de nateglinide
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WO2009085223A1 (fr) * 2007-12-20 2009-07-09 Indigene Pharmaceuticals, Inc. Combinaison de r-(+)-lipoate de metformine et d'agents antihyperglycémiques pour le traitement de l'hyperglycémie diabétique et des complications diabétiques
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US6271254B1 (en) * 1989-11-09 2001-08-07 Asta Pharma Aktiengesellschaft Pharmaceutical compositions containing R-α-lipoic acid or S-α-lipoic acid as active ingredient
EP1283054A1 (fr) * 2000-03-17 2003-02-12 Ajinomoto Co., Inc. Medicaments permettant de traiter les complications du diabete et des neuropathies et utilisation de ces medicaments
EP1334721A1 (fr) * 2000-10-24 2003-08-13 Ajinomoto Co., Inc. Preparations de medicament contenant du nateglinide
WO2002072146A2 (fr) * 2001-03-12 2002-09-19 Novartis Ag Combinaison de composes organiques
US20060127475A1 (en) * 2003-08-08 2006-06-15 Ajinomoto Co., Inc. Nateglinide-containing preparation
WO2005020979A1 (fr) * 2003-09-03 2005-03-10 Ranbaxy Laboratories Limited Procede de preparation de compositions pharmaceutiques a base de nateglinide
WO2009085223A1 (fr) * 2007-12-20 2009-07-09 Indigene Pharmaceuticals, Inc. Combinaison de r-(+)-lipoate de metformine et d'agents antihyperglycémiques pour le traitement de l'hyperglycémie diabétique et des complications diabétiques
EP2386552A1 (fr) * 2010-05-11 2011-11-16 CBB Net S.A. Procédé de préparation de sels d'acides (R) a-lipoïques, leur formulation et utilisation pour les compositions pharmaceutiques, sous forme de comprimés les contenant

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SINGH U ET AL: "Alpha-lipoic acid supplementation and diabetes", NUTRITION REVIEWS, ALLEN PRESS, LAWRENCE, KS, US, vol. 66, no. 11, 1 November 2008 (2008-11-01), pages 646 - 657, XP002551024, ISSN: 0029-6643, [retrieved on 20081027], DOI: 10.1111/J.1753-4887.2008.00118.X *
SONG K-H ET AL: "alpha-Lipoic acid prevents diabetes mellitus in diabetes-prone obese rats", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, ACADEMIC PRESS INC. ORLANDO, FL, US, vol. 326, no. 1, 31 December 2004 (2004-12-31), pages 197 - 202, XP004672568, ISSN: 0006-291X, DOI: 10.1016/J.BBRC.2004.10.213 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11986460B2 (en) 2018-11-26 2024-05-21 The Procter & Gamble Company Solid pharmaceutical preparation containing lipoic acid and use thereof

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EP2809316A1 (fr) 2014-12-10
WO2013115740A1 (fr) 2013-08-08

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