EP1513501A2 - Einfache und multiple emulsionen zur dekontamination eines organismus oder von flächen - Google Patents

Einfache und multiple emulsionen zur dekontamination eines organismus oder von flächen

Info

Publication number
EP1513501A2
EP1513501A2 EP03756050A EP03756050A EP1513501A2 EP 1513501 A2 EP1513501 A2 EP 1513501A2 EP 03756050 A EP03756050 A EP 03756050A EP 03756050 A EP03756050 A EP 03756050A EP 1513501 A2 EP1513501 A2 EP 1513501A2
Authority
EP
European Patent Office
Prior art keywords
approximately
aqueous phase
organic phase
extractant
mass
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Withdrawn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
EP03756050A
Other languages
English (en)
French (fr)
Inventor
Elise Mona-Lydia Dobin-Assouly
Jean-Louis Grossiord
Dominique Nicole Michèle PAREAU
Monique Anne Seiller-Boutin
Moncef Rec. STAMBOULI (J116)
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.)
Centre National de la Recherche Scientifique CNRS
Universite Paris Sud
Ecole Centrale de Paris ECP
Original Assignee
Centre National de la Recherche Scientifique CNRS
Universite Paris Sud
Ecole Centrale de Paris ECP
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 Centre National de la Recherche Scientifique CNRS, Universite Paris Sud, Ecole Centrale de Paris ECP filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP1513501A2 publication Critical patent/EP1513501A2/de
Withdrawn legal-status Critical Current

Links

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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/113—Multiple emulsions, e.g. oil-in-water-in-oil
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the subject of the invention is new simple water-in-oil emulsions, or multiple water-in-oil-in-water emulsions, and their use for detoxifying the body or surfaces.
  • Acute intoxication represents, at the start of this millennium, one of the main causes of hospitalization in developed countries and death of individuals under the age of thirty in developing countries.
  • the invention makes it possible to provide an original and effective alternative in the essential treatments intended for industrial, military emergencies, hospital, domestic and environmental.
  • the invention aims to allow the treatment of oral poisoning which originates from the ingestion of pharmaceutical and non-pharmaceutical products, but also skin intoxication of domestic, industrial or military origin.
  • the present invention aims to use very stable emulsions due to the presence in these emulsions of polymeric surfactants.
  • the present invention relates to the use of single or multiple emulsions comprising in their organic phase one or more extracting compounds capable, when said emulsions are brought into contact with a medium, also designated external medium, either biological such as gastric liquid, skin or blood, either artificial or metallic or plastic surfaces, to extract from said medium specific toxic molecules capable of binding to said or said extractants, for the preparation of pharmaceutical compositions intended for the prevention or treatment of intoxication by oral, topical or parenteral, or for detoxifying surfaces by simple application to the aforementioned surfaces.
  • a medium also designated external medium, either biological such as gastric liquid, skin or blood, either artificial or metallic or plastic surfaces
  • the present invention relates to the use as mentioned above, of simple water in oil emulsions, or multiple water in hujle in water emulsions, the internal aqueous phase of which comprises one or more de-extracting compounds, trapping the toxic molecules extracted from the external medium .
  • extracting compound is meant a molecule which will react chemically with the complex formed by the toxic molecule and the extractant, which on the one hand makes it possible to regenerate the extractant, and on the other hand, to trap the molecule toxic.
  • the present invention also relates to the abovementioned use, characterized in that the extractant is chosen from:
  • - amino derivatives such as primary, secondary or tertiary amines or quaternary ammonium salts, comprising one or more carbon chains each comprising around 1 to 18 carbon atoms, in particular trioctylamine or trilaurylamine, when the toxic molecule to be eliminated has an acid or anionic character,
  • organic acids such as organophosphorus acids, thiophosphorus acids, carboxylic acids, comprising one or more carbon chains each comprising from approximately 1 to 18 carbon atoms, when the toxic molecule to be eliminated has a basic or cationic character
  • the solvating molecules such as alcohols, organophosphates, phosphine oxides, organosulfides or sulfoxides, comprising one or more carbon chains each comprising about 1 to 18 carbon atoms, when the toxic molecule to be eliminated has a neutral character.
  • molecule having an acid character designates in the broad sense a - Lewis acid (electron acceptor) such as a weak acid, in particular acetic acid, lactic acid, citric acid, acetylsalicylic acid or hydrocyanic acid.
  • a - Lewis acid electron acceptor
  • molecule having an anionic character designates an aqueous anion such as for example cyanide, fluoride or chloride ions, or anionic metal complexes such as for example FeC-U " or AuCLf-
  • molecule having a basic character designates in the broad sense a Lewis base (electron donor) having for example a nitrogen atom (protonable) such as Toxin, urea, ammonia, quinine or amphetamines, or having a sulfur atom (protonable) such as for example the sulfide ion or the sulfite ion.
  • molecule having a cationic character designates an aqueous cation such as for example the ammonium ion or the metal cations.
  • molecule having a neutral character designates a molecule having no marked electron exchange properties, such as for example alcohols (ethanol), ketones, ethers, paracetamol, etc.
  • a preferred organophosphorus acid, among the extractants, is di-2-ethylhexylphosphoric acid.
  • octanol or decanol are preferably used as extractants.
  • the present invention relates to the use as defined above, characterized in that the deextractant is chosen from: - bases such as NaOH, KOH, Na 2 CO 3 , when the toxic molecule to be eliminated has an acid or anionic character,
  • oxidoreductive or complexing character such as chromium (VI) salts, thiourea, ethylene diamine tetracetic acid, chlorinated or fluorinated derivatives, ascorbic acid, when the toxic molecule to be eliminated has a neutral character.
  • compounds with an oxidoreducing or complexing character designates compounds capable of reducing or oxidizing the toxic agent or of forming with it a lipophobic complex.
  • the invention relates to the use of simple water-in-oil emulsions comprising:
  • One or more extractants as defined above, the mass fraction of the extractant (s) relative to the organic phase being between approximately 0.1 and approximately 20%,
  • One or more ether-bonded lipophilic surfactants such as al-kyldimethicone copolyols, or amine-bonded surfactants such as long chain condensed polyamines, or sorbitan or glycol esters, the mass fraction of the lipophilic surfactant (s) relative to the organic phase being between approximately 0.5 and approximately 20%,
  • hydrocarbons such as liquid paraffins, perhydrosqualene or silicones or synthetic esters
  • an internal aqueous phase containing one or more deextractants as defined above, and optionally an additive such as an electrolyte or a sugar, the mass ratio of the internal aqueous phase relative to the emulsion being between approximately 1 and about 80%, preferably between about 20% and about 70%.
  • the invention relates to the use of multiple water-in-oil-in-water emulsions comprising: an external aqueous phase containing one or more hydrophilic surfactants with ether bond such as copolymers of ethylene oxide and propylene oxide, oxyethylenated fatty alcohols, or hydrophilic surfactants with ester bond such as polyoxyethylenated sorbitan esters , the mass fraction of these surfactants relative to the external aqueous phase being between approximately 0.1 and approximately 10%.
  • hydrophilic surfactants with ether bond such as copolymers of ethylene oxide and propylene oxide, oxyethylenated fatty alcohols, or hydrophilic surfactants with ester bond such as polyoxyethylenated sorbitan esters
  • One or more extractants as defined above, the mass fraction of the extractant (s) relative to the organic phase being between approximately 0.1 and approximately 20%,
  • one or more lipophilic surfactants with ether bond such as alkyldimethicone copolyols, or with amino bond such as condensed polyamines with long chains, or sorbitan or glycol esters, the mass fraction of the lipophilic surfactant (s) relative to the phase organic being between approximately 0.5 and approximately 20%,
  • hydrocarbons such as liquid paraffins, perhydrosqualene or silicones or synthetic esters
  • the invention relates to the use as mentioned above, of single or multiple emulsions, for the detoxification of acid molecules, such as acetylsalicylic acid, characterized in that the extractant is a tertiary amine, in particular trioctylamine or trilaurylamine, and in that the deextractant is sodium hydroxide NaOH.
  • the invention relates to the use as mentioned above, of simple water-in-oil emulsions, for the detoxification of acid molecules, such as acetylsalicylic acid, comprising:
  • Cetyldimethicone copolyol as lipophilic surfactant at a rate of approximately 1 to approximately 10% by mass relative to the external organic phase
  • an internal aqueous phase containing, as deextractant, sodium hydroxide, at a concentration such that the pH is greater than or equal to 13, the mass ratio between the aqueous phase and the total emulsion being between approximately 10% and approximately 70%, and preferably equal to about 50%.
  • the invention relates to the use as mentioned above, of multiple water-in-oil-in-water emulsions, for the detoxification of acid molecules, such as acetylsalicylic acid, comprising:
  • Cetyldimethicone copolyol as lipophilic surfactant at a rate of approximately 1 to approximately 10% by mass relative to the total mass of the organic phase,
  • an internal aqueous phase containing, assupplementaryextractant, soda, at a concentration such that the pH is greater than or equal to 13, and magnesium sulfate, from about 2 to about 6% 'by weight relative to the total mass of the internal aqueous phase, the mass ratio between the internal aqueous phase and the organic phase being between approximately 25% and approximately 200%, and preferably equal to approximately 100%, and the mass ratio between the phase external aqueous and the primary single emulsion being between approximately 10% and approximately 90%, and preferably equal to approximately 25%.
  • the invention relates to the use as mentioned above, of single or multiple emulsions, for the detoxification of -composites of very weak acid-base character, such as paracetamol, characterized in that the extractant used is a long-chain alcohol, in particular octanol, and in that the deextractant is NaOH.
  • the invention relates to the use as mentioned above, of simple water in oil emulsions comprising:
  • a polyamine condensed on succinic acid substituted with a polyisobutene chain such as ECA 4360, as lipophilic surfactant, in a proportion of approximately 1 to approximately 10% by mass relative to the external organic phase ,
  • an internal aqueous phase containing, as a de-extractant, sodium hydroxide at a concentration such that the pH is greater than 13, the mass ratio between the aqueous phase and the total emulsion being between approximately 10% and approximately 70%, and preferably equal to about 50%.
  • the invention relates to the use as mentioned above, of single or multiple emulsions, for the detoxification of compounds such as zopiclone ND , characterized in that the extractant used is an acid long-chain organothiophosphorus, in particular di-ethylhexyl-monothiophosphinic acid (Cyanex 302), and in that the deextractant is hydrochloric acid.
  • the extractant used is an acid long-chain organothiophosphorus, in particular di-ethylhexyl-monothiophosphinic acid (Cyanex 302), and in that the deextractant is hydrochloric acid.
  • the invention relates to the use as mentioned above, of simple water in oil emulsions comprising:
  • ECA 4360 as lipophilic surfactant, at a rate of approximately 1 to approximately 10% by mass relative to the organic phase
  • the present invention relates more particularly to the use of single or multiple emulsions as defined above, for the preparation of compositions intended for the decontamination of surfaces.
  • the present invention more particularly relates to the use of single or multiple emulsions as defined above, for the preparation of pharmaceutical compositions intended for the prevention or treatment of intoxication by oral, topical or parenteral route.
  • the present invention also relates to the use of single or multiple emulsions as defined above, for the preparation of medical devices intended for the prevention or treatment of intoxication by oral, topical or parenteral route.
  • the present invention also relates to a pharmaceutical composition characterized in that it comprises a single or multiple emulsion as defined above, where appropriate in combination with a pharmaceutically acceptable vehicle.
  • An advantageous pharmaceutical composition according to the invention is characterized in that it is in a form which can be administered by the oral route, single or repeated, in particular at a rate of approximately 10 to approximately 500 g.
  • An advantageous pharmaceutical composition according to the invention is characterized in that it is in a form which can be administered topically, in particular at a rate of approximately 2 to approximately 50 mg / cm 2 of skin.
  • An advantageous pharmaceutical composition according to the invention is characterized in that it is in a form which can be used for the parenteral route by an extracorporeal circulation, in particular at a rate of approximately 500 to approximately 1000 g.
  • the present invention also relates to any multiple water-in-oil-in-water emulsion comprising in its organic phase one or more extracting compounds as defined above.
  • the invention relates to any multiple emulsion as defined above, comprising in its organic phase one or more lipophilic surfactants as defined above.
  • An advantageous multiple emulsion of the present invention comprises in its internal aqueous phase one or more deextracting compounds as defined above, and optional additives such as electrolytes or sugars.
  • the preferred electrolytes are sodium chloride or magnesium sulfate.
  • the preferred sugars are glucose or sucrose.
  • An advantageous multiple emulsion of the present invention comprises in its external aqueous phase one or more hydrophilic surfactants as defined above.
  • an external aqueous phase containing one or more hydrophilic ether-surfactants such as copolymers of ethylene oxide and propylene oxide, oxyethylenated fatty alcohols, or hydrophilic surfactants with ester bond such as polyoxyethylenated sorbitan esters , the mass fraction of these surfactants relative to the external aqueous phase being between approximately 0.1 and approximately 10%.
  • hydrophilic ether-surfactants such as copolymers of ethylene oxide and propylene oxide, oxyethylenated fatty alcohols, or hydrophilic surfactants with ester bond such as polyoxyethylenated sorbitan esters
  • One or more extractants as defined above, the mass fraction of the extractant (s) relative to the organic phase being between approximately 0.1 and approximately 20%,
  • one or more lipophilic surfactants with ether bond such as alkyldimethicone copolyols, or with amino bond such as condensed polyamines with long chains, or sorbitan or glycol esters, the mass fraction of the lipophilic surfactant (s) relative to the phase organic being between approximately 0.5 and approximately 20%,
  • hydrocarbons such as liquid paraffins, perhydrosqualene or silicones or synthetic esters
  • the present invention also relates to a multiple emulsion as defined above, for the detoxification of acid molecules, such as acetylsalicylic acid, comprising:
  • Cetyldimethicone copolyol as lipophilic surfactant at a rate of approximately 1 to approximately 10% by mass relative to the total mass of the organic phase,
  • an internal aqueous phase containing, as a de-extractant, sodium hydroxide, at a concentration such that the pH is greater than or equal to 13, and magnesium sulphate, at a rate of approximately 2 to approximately 6% by mass relative to total mass of the internal aqueous phase, the mass ratio between the internal aqueous phase and the organic phase being between approximately 25% and approximately 200%, and preferably equal to approximately 100%, and the mass ratio between the external aqueous phase and the primary single emulsion being between approximately 10% and approximately 90%, and preferably equal to approximately 25%.
  • the principle of the extraction of toxic molecules by an emulsified system (water in oil emulsion or water in oil in water emulsion) consists of:
  • system I a simple water in oil emulsion
  • system II a multiple water in oil in water emulsion
  • a simple water-in-oil emulsion is prepared.
  • This simple emulsion is stabilized by a lipophilic surfactant of low HLB (Hydrophilic / Lipophilic Balance) and contains fine droplets of internal aqueous phase with a diameter of 0.5 to 1 ⁇ m. It is presented as a relatively viscous milk.
  • HLB Hydrophilic / Lipophilic Balance
  • the toxic compound will pass through the organic solution to be collected and trapped in the droplets of internal aqueous phase.
  • the originality and the efficiency of the process of the present invention are based on two particularly important aspects: the presence in the organic solution of a molecule (transporter or extractant) capable of helping the transport of the toxic compound in this phase and the presence in the internal aqueous phase of a trapping agent (de-extractant) which destroys the toxic-transporter complex and reacts with the latter to transform it into a very lipophobic species.
  • a trapping agent de-extractant
  • Acetylsalicylic acid will be denoted HA for the sake of simplification.
  • the transporter is a long chain tertiary amine (R 3 N), a molecule with a weak basic character, which is very slightly soluble in water.
  • the R 3 .NHA molecule is much more lipophilic than HA and therefore facilitates its solubilization in the organic phase.
  • the trapping agent introduced into the internal aqueous phase is sodium hydroxide.
  • the following chemical reaction takes place:
  • Such a chemical system is also valid for other toxic molecules with an acidic character.
  • organic acids such as lactic acid, ascorbic acid or citric acid
  • mineral acids such as hydrochloric acid, nitric acid.
  • sulfuric acid, hydrofluoric acid or hydrocyanic acid such as sulfuric acid, hydrofluoric acid or hydrocyanic acid.
  • Primary, secondary and tertiary amines can be used as the carrier, provided they have one or more long carbon chains (to minimize their solubility in water). However, tertiary amines are the most effective because they are the most basic.
  • the internal aqueous solution is a basic solution, consisting of a strong base like soda or potash or a weak base like sodium carbonate or potassium carbonate.
  • strong bases are the most effective.
  • trioctylamine C 8 H 1 ) 3 N or trilaurylamine (C 12 H 25 ) 3 N
  • emulsions are prepared containing the following components:
  • NaOH of different concentrations 50% (thereafter, all percentages represent mass ratios)
  • TLA trilaurylamine
  • the optimum content of the surfactant is therefore of the order of 3 to 5% of Abil.
  • the following emulsions, containing trioctylamine (TOA) are prepared:
  • composition of the emulsion prepared is as follows Dodecane: 47.1% TOA: 0.9% ABIL: 2% NaOH 0.1 mol.L "1 : 50% The extraction percentages obtained are as follows
  • Arlatone F127G copolymer of ethylene oxide and propylene oxide
  • the primary emulsion is prepared by heating the internal aqueous phase and the organic phase to 70-80 ° C using a water bath.
  • the aqueous phase is incorporated into the oily phase with vigorous stirring at 3000 rpm using a Rayneri centripetal turbine for 30 minutes.
  • the primary emulsion is slowly introduced into the external aqueous phase.
  • This second emulsification is carried out by the same turbine with stirring of 500 rpm.
  • the duration of agitation depends on the formulation and can vary from 5 to 45 minutes.
  • solvating transporter for very weak acid-base toxic molecules (alcohol, glycol; paracetamol for example), a solvating transporter and an internal aqueous phase capable of reacting with the toxic agent to trap it in a lipophobic form (oxidant, strong base) will be considered. ..).
  • Symmetrical systems are envisaged for extracting toxic substances of a basic nature by using as carrier a acid organic molecule (organophosphorus acid, carboxylic acid) very poorly soluble in water; the internal aqueous solution will be an acid solution.
  • a acid organic molecule organic molecule (organophosphorus acid, carboxylic acid) very poorly soluble in water; the internal aqueous solution will be an acid solution.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Dispersion Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Colloid Chemistry (AREA)
  • Detergent Compositions (AREA)
EP03756050A 2002-06-04 2003-06-04 Einfache und multiple emulsionen zur dekontamination eines organismus oder von flächen Withdrawn EP1513501A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0206849A FR2840218B1 (fr) 2002-06-04 2002-06-04 Emulsions simples et multiples destinees a la detoxication de l'organisme ou de surfaces
FR0206849 2002-06-04
PCT/FR2003/001674 WO2003101426A2 (fr) 2002-06-04 2003-06-04 Emulsions simples et multiples destinees a la detoxication de l'organisme ou de surfaces

Publications (1)

Publication Number Publication Date
EP1513501A2 true EP1513501A2 (de) 2005-03-16

Family

ID=29558949

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03756050A Withdrawn EP1513501A2 (de) 2002-06-04 2003-06-04 Einfache und multiple emulsionen zur dekontamination eines organismus oder von flächen

Country Status (5)

Country Link
US (1) US20050244438A1 (de)
EP (1) EP1513501A2 (de)
AU (1) AU2003255635A1 (de)
FR (1) FR2840218B1 (de)
WO (1) WO2003101426A2 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060126701A (ko) * 2003-12-10 2006-12-08 애크럭스 디디에스 피티와이 리미티드 경피 또는 국소 약물 전달에 따른 원치않는 효과의치료방법
CN103558242B (zh) * 2013-11-14 2016-01-20 河南理工大学 水体中颗粒态有机磷的提取及测定方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3934007A (en) * 1973-06-25 1976-01-20 American Cyanamid Company Method of removing toxic substances from the intestinal tract by the use of a surfactant and a sorbent
CA1045976A (en) * 1974-05-02 1979-01-09 William J. Asher Liquid membrane encapsulated medicinals and uses thereof
US4259318A (en) * 1978-03-02 1981-03-31 University Of Houston, Central Campus Poison ivy relief composition
FR2419730A1 (fr) * 1978-03-13 1979-10-12 Armines Procede d'epuration selective par membranes liquides en emulsion
US4191812A (en) * 1978-09-19 1980-03-04 Rohm And Haas Company Ion exchange process involving emulsion ion exchange resins
US4806354A (en) * 1984-04-06 1989-02-21 Green James P Health food composition
EP0236883B1 (de) * 1986-03-06 1992-06-03 Odenwaldwerke Rittersbach GmbH Fahrzeugbau und Katastrophenschutzsysteme Vorrichtung zum Erzeugen einer Entgiftungsemulsion für Kampfstoffe
DE3638625A1 (de) * 1986-11-12 1988-05-26 Bundesrep Deutschland Entgiftungs-emulsion sowie verfahren, vorrichtung und erfolgskontrolle zur herstellung der emulsion
FR2761607A1 (fr) * 1997-04-04 1998-10-09 Boots Co Plc Composition dermatologique pour le traitement des symptomes de vieillissement de la peau
WO2002076392A2 (en) * 2001-03-21 2002-10-03 Madash Llc Thermally reversible water in oil in water emulsions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03101426A2 *

Also Published As

Publication number Publication date
AU2003255635A1 (en) 2003-12-19
FR2840218A1 (fr) 2003-12-05
US20050244438A1 (en) 2005-11-03
FR2840218B1 (fr) 2004-08-13
WO2003101426A2 (fr) 2003-12-11
AU2003255635A8 (en) 2003-12-19
WO2003101426A3 (fr) 2004-04-08

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