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WO2002064124A2 - Composition medicamenteuse qui contient un agoniste muscarinique - Google Patents

Composition medicamenteuse qui contient un agoniste muscarinique Download PDF

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Publication number
WO2002064124A2
WO2002064124A2 PCT/EP2002/001374 EP0201374W WO02064124A2 WO 2002064124 A2 WO2002064124 A2 WO 2002064124A2 EP 0201374 W EP0201374 W EP 0201374W WO 02064124 A2 WO02064124 A2 WO 02064124A2
Authority
WO
WIPO (PCT)
Prior art keywords
core
tablet according
weight
film
acid
Prior art date
Application number
PCT/EP2002/001374
Other languages
German (de)
English (en)
Other versions
WO2002064124A3 (fr
Inventor
Thomas Friedl
Karoline Bechtold-Peters
Michael Walz
Original Assignee
Boehringer Ingelheim Pharma Gmbh & Co. Kg
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 Boehringer Ingelheim Pharma Gmbh & Co. Kg filed Critical Boehringer Ingelheim Pharma Gmbh & Co. Kg
Priority to MXPA03007272A priority Critical patent/MXPA03007272A/es
Priority to EP02716755A priority patent/EP1361871A2/fr
Priority to CA002434976A priority patent/CA2434976A1/fr
Priority to AU2002247705A priority patent/AU2002247705A1/en
Priority to JP2002563919A priority patent/JP2004518710A/ja
Publication of WO2002064124A2 publication Critical patent/WO2002064124A2/fr
Publication of WO2002064124A3 publication Critical patent/WO2002064124A3/fr

Links

Classifications

    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin

Definitions

  • the invention relates to a new pharmaceutical formulation containing the muscarinic agonist talsaclidine and processes for their preparation.
  • talsaclidine (Wal2014) is a compound with pharmacologically valuable properties.
  • muscarinic agonists can have great therapeutic benefits in the treatment of Alzheimer's disease.
  • Talsaclidin V has the following chemical structure:
  • the present invention relates to a tablet containing talsaclidine V, characterized in that it consists of a core containing the active ingredient talsaclidine and a film coating encasing this core.
  • the tablet according to the invention can also be referred to as a film tablet in the context of the present invention.
  • physiologically acceptable acid addition salts are understood to be pharmaceutically acceptable salts which are selected from the salts of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, acetic acid, fumaric acid, succinic acid, lactic acid, citric acid, tartaric acid and maleic acid. If necessary, can Production of the salts, mixtures of the abovementioned acids can also be used.
  • the salts of talsaclidine are preferably selected from the group consisting of hydrochloride, hydrobromide, sulfate, phosphate, fumarate and methanesulfonate.
  • the salts are particularly preferably selected from hydrochloride, hydrobromide and fumarate, the talsaclidin fumarate being of the greatest importance according to the invention.
  • the active ingredient may optionally be in the form of a hydrate.
  • the talsaclidine is preferably added in an anhydrous form.
  • the active ingredient is preferably used in crystalline, unground form or pin-ground form, but preferably in unground form.
  • Active ingredient is particularly preferably used in unmilled form, in which the particle size distribution lies within the following limits: D-io 20 20 ⁇ m, D 50 10-80 ⁇ m, D 90 ⁇ 300 ⁇ m.
  • the particle size distribution of the active ingredient used in the formulation according to the invention is particularly preferably in the following ranges: D-io ⁇ 5-15 ⁇ m, D 50 25-75 ⁇ m, D 90 ⁇ 275 ⁇ m.
  • D 5 and D o in 90 microns is the particle size ranges within which a passage amount of 10 volume%, 50 volume% and 90 volume% of the particles measured (cumulative volume distribution) is achieved.
  • talsaclidine V is present according to the invention at 0.5 to 25% by weight, preferably 0.7 to 20% by weight, particularly preferably about 0.9 to 15% by weight.
  • the proportion of V is particularly preferably between 9 and 14% by weight, based on the total mass of the core.
  • the proportion of 1, based on the total mass of the core of the film tablets according to the invention is between about 0.85 to 43% by weight, preferably between about 1.2 to 2% by weight 34% by weight, particularly preferably between about 1.5 to 26% by weight.
  • the proportion of 1 is particularly preferably in the case of Talsaclidin fumarate between about 15 and 24% by weight based on the total mass of the core.
  • the core of the pharmaceutical formulation according to the invention also contains at least one auxiliary as filler / dry binder.
  • modified lactose in particular spray-dried lactose
  • This auxiliary has proven to be particularly advantageous in the formulation according to the invention.
  • a preferred aspect of the present invention therefore relates to a film tablet containing talsaclidine, which contains, in addition to the active substance, modified lactose, in particular spray-dried lactose, particularly preferably spray-dried lactose monohydrate, as an adjuvant.
  • Spray-dried lactose is to be understood as lactose which is obtained by spray agglomeration when spray-drying a suspension of ⁇ -
  • Lactose monohydrate crystals are formed in an aqueous lactose solution.
  • the spray drying process results in a free-flowing powder with suitable granulometry for direct tableting (for example 80-100% ⁇ 250 ⁇ m) and an amorphous fraction of for example 5-25%, which is responsible for the high binding capacity of spray-dried lactose.
  • the weight ratio between the components of modified lactose, preferably spray-dried lactose, and active ingredient V contained in the core of the film-coated tablet is in a range from about 1: 1 to about 70: 1.
  • the ratio of modified, preferably spray-dried lactose to V is preferably in a range from about 1.5: 1 to. about 35: 1, particularly preferably in a range from about 2: 1 to about 8: 1.
  • the weight fraction of the modified, preferably spray-dried lactose, based on the total mass of the core of the film-coated tablet according to the invention, is preferably in a range from approximately 20-70% by weight, preferably between approximately 30-60% by weight.
  • the core of the film-coated tablet according to the invention can also contain further auxiliaries or fillers.
  • preference can be given to those compounds which can act as dry binders.
  • Dry binders preferred according to the invention are selected from the group consisting of powder cellulose, microcrystalline cellulose, starch, povidone, cellulose derivatives and mixtures of these compounds. Powder cellulose and / or microcrystalline cellulose are preferred as binders, particularly preferably microcrystalline cellulose contain.
  • the weight ratio of modified, preferably spray-dried lactose to binder is preferably about 5: 1 to about 1: 4, preferably about 4: 1 to about 1: 3, particularly preferably about 3: 1 to 1: 2.
  • the weight ratio of spray-dried lactose to binder is particularly preferably in a range from about 2: 1 to about 1: 1.
  • the core of the film-coated tablet according to the invention may also contain disintegrants in addition to the above-mentioned components.
  • these disintegrants may also be referred to as disintegrants.
  • these are preferably selected from the group consisting of sodium starch glycolate, crospovidone, croscarmellose, sodium carboxymethyl cellulose, dried corn starch and mixtures thereof.
  • sodium starch glycolate, crospovidone and croscarmellose, preferably sodium starch glycolate are particularly preferably used.
  • their proportion by weight based on the total mass of the core of the film-coated tablet according to the invention, is preferably in a range from about 1-10% by weight, particularly preferably about 3-8% by weight.
  • the core of the film-coated tablet according to the invention may also contain flow regulators as further constituents.
  • Flow regulating agents in the context of the present invention are, for example, silicon dioxide, talc and magnesium stearate.
  • silicon dioxide is preferably used, particularly preferably in colloidal, highly disperse form. If the above-mentioned flow regulating agents are used, their proportion by weight, based on the total mass of the core of the film-coated tablet according to the invention, is preferably in a range from approximately 0.1 to 5% by weight, preferably approximately 0.3 to 2% by weight, particularly preferably between 0.4 and 1.5 wt%.
  • the core of the film-coated tablet according to the invention can also contain flow agents, lubricants and release agents as further constituents.
  • stearic acid, magnesium stearate, sodium stearyl fumarate, glycerol tribehenate and mixtures thereof come into consideration within the scope of the present invention.
  • Stearic acid and magnesium stearate are preferably used according to the invention.
  • the proportion by weight, based on the total mass of the core of the film-coated tablet according to the invention is preferably in a range from approximately 0.1 to 5% by weight, preferably approximately 0.5 to 3% by weight, particularly preferably approximately 1-2% by weight.
  • a particularly good one Mold release in the production of the film-coated tablets according to the invention is achieved if magnesium stearate is used in an amount of at least 1.0% by weight, preferably about 1.5% by weight.
  • the film or film covering surrounding the core of the film-coated tablets according to the invention contains, as an essential component, a film-forming agent which is selected from hydroxypropylmethyl cellulose, hydroxypropyl cellulose, methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose and poly (ethyl acrylate) methyl methacrylate, the latter for example in the form of Eudragit NE 30 D. Alternatively Eudragit RL 30 D or Eudragit E 12.5 can also be used. The above-mentioned constituents can optionally also be used in the form of their mixtures.
  • Preferred film formers are hydroxypropyl methyl cellulose, hydroxypropyl cellulose, hydroxymethyl cellulose and hydroxyethyl cellulose, with hydroxypropyl methyl cellulose and hydroxypropyl cellulose being particularly preferred according to the invention as film formers.
  • the above film formers can be used alone or in the form of their mixtures. If only one of the above-mentioned film formers is used, hydroxypropylmethyl cellulose is of particular importance in the context of the present invention.
  • the proportion by weight of film former, based on the total mass of the film coating of the film tablet according to the invention, is preferably in a range from about 20-95% by weight, preferably 30-90% by weight.
  • the film coating can contain, as further constituents, emulsifiers and plasticizers, such as, for example, polyethylene glycol, glycerol and propylene glycol, optionally in the form of their mixtures.
  • plasticizers such as, for example, polyethylene glycol, glycerol and propylene glycol, optionally in the form of their mixtures.
  • Polyethylene glycols are preferably used as plasticizers. Without restricting the subject matter of the invention, particularly preferred polyethylene glycols are, for example, polyethylene glycol 400 and polyethylene glycol 6000.
  • the weight fraction of plasticizer, based on the total mass of the film coating of the film-coated tablet according to the invention is preferably in a range from about 1-30% by weight, preferably 3- 25% by weight, particularly preferably 5-15% by weight.
  • the film coating of the film-coated tablet according to the invention can also contain color pigments and pigmentation aids.
  • color pigments and pigmentation aids examples include iron oxide, titanium dioxide, talc and their mixtures.
  • the film tablet according to the invention can be produced, for example, as described below.
  • the excipient spray-dried lactose is mixed together with the active ingredient 1 in a suitable free-fall mixer.
  • the premix of active ingredients obtained therefrom is then mixed in a suitable screening machine. This reduces the proportion of coarser active substance particles used in the manufacturing process. Depending on the particle size of the compound 1 used, it is also possible to dispense with the production of this premix with subsequent sieving.
  • further excipient is added to this active ingredient premix.
  • one or more further auxiliaries can also be added.
  • further formulation components such as disintegrants and flow regulators can be added during this process step.
  • the active ingredient / excipient mixture obtained in this way is then compressed on a suitable tablet press to give the film-coated tablet cores according to the invention.
  • the pressing force should be e.g. in the case of tablet cores containing 36 mg of talsaclidine V, they are kept in a range from 5 to 15 kN, preferably 8 to 12 kN. Higher compressive forces can lead to tablets with a slow release of the active ingredient. Lower compression forces can lead to mechanically unstable tablets.
  • the tablet cores can have different formats, preferably round biplane or biconvex and oval or oblong shapes.
  • the required and optional components of the film coating are taken up in a suitable solvent.
  • a suitable solvent According to the invention, water is preferably used as the solvent. When water is used as the solvent, some of the components of the film coating are in dispersed form.
  • the tablet cores previously obtained are coated with the desired film in a suitable coating device in analogy to the coating processes known in the prior art.
  • the following examples serve to illustrate formulations according to the invention. They are only to be understood as possible exemplary procedures, without restricting the invention to its content.
  • Lactose monohydrate 99.363 mg
  • Microcrystalline cellulose 90.450 mg
  • Titanium dioxide 1.750 mg
  • Lactose monohydrate (spray dried): 209.09 mg
  • Microcrystalline cellulose 102.00 mg
  • Titanium dioxide 1, 5696 mg
  • Kern talsaclidine fumarate 10.21 mg
  • Lactose monohydrate (spray dried): 203.99 mg
  • Microcrystalline cellulose 102.00 mg
  • Lactose monohydrate (spray dried): 193.77 mg
  • Microcrystalline cellulose 102.00 mg
  • Microcrystalline cellulose 102.00 mg
  • Kern talsaclidin fumarate 51.07 mg
  • Lactose monohydrate 163.13 mg
  • Microcrystalline cellulose 102.00 mg
  • Talsaclidine fumarate 61.29 mg lactose monohydrate (spray dried): 152.91 mg
  • Microcrystalline cellulose 102.00 mg
  • Kern talsaclidine fumarate 81, 72 mg
  • Lactose monohydrate (spray dried): 132.48 mg
  • Microcrystalline cellulose 102.00 mg
  • Talsaclidine fumarate 40.86 mg lactose monohydrate (spray dried): 66.24 mg
  • Microcrystalline cellulose 60.30 mg

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Nouvelle composition médicamenteuse qui contient l'agoniste muscarinique talsaclidine, et procédé de préparation de ladite composition.
PCT/EP2002/001374 2001-02-15 2002-02-09 Composition medicamenteuse qui contient un agoniste muscarinique WO2002064124A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
MXPA03007272A MXPA03007272A (es) 2001-02-15 2002-02-09 Formulacion de medicamento que contiene agonista muscarinico.
EP02716755A EP1361871A2 (fr) 2001-02-15 2002-02-09 Composition medicamenteuse qui contient un agoniste muscarinique
CA002434976A CA2434976A1 (fr) 2001-02-15 2002-02-09 Composition medicamenteuse qui contient un agoniste muscarinique
AU2002247705A AU2002247705A1 (en) 2001-02-15 2002-02-09 Medicament formulation containing a muscarinic agonist
JP2002563919A JP2004518710A (ja) 2001-02-15 2002-02-09 ムスカリン性アゴニストを含む医薬品製剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10106971A DE10106971A1 (de) 2001-02-15 2001-02-15 Arzneimittelformulierung die einen muskarinischen Agonisten enthält
DE10106971.5 2001-02-15

Publications (2)

Publication Number Publication Date
WO2002064124A2 true WO2002064124A2 (fr) 2002-08-22
WO2002064124A3 WO2002064124A3 (fr) 2002-12-05

Family

ID=7674095

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/001374 WO2002064124A2 (fr) 2001-02-15 2002-02-09 Composition medicamenteuse qui contient un agoniste muscarinique

Country Status (9)

Country Link
EP (1) EP1361871A2 (fr)
JP (1) JP2004518710A (fr)
AR (1) AR033862A1 (fr)
AU (1) AU2002247705A1 (fr)
CA (1) CA2434976A1 (fr)
DE (1) DE10106971A1 (fr)
MX (1) MXPA03007272A (fr)
UY (1) UY27170A1 (fr)
WO (1) WO2002064124A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010033045A1 (fr) * 2008-09-16 2010-03-25 Igor Anatolievich Pomytkin Compositions et procédés pour la prévention ou le traitement d’un dépôt bêta-amyloïde
EP2140867A4 (fr) * 2007-03-29 2013-07-03 Daiichi Sankyo Co Ltd Composition pharmaceutique
US9402907B2 (en) 2011-08-10 2016-08-02 Daiichi Sankyo Company, Limited Pharmaceutical composition containing diamine derivative
US9918975B2 (en) 2010-03-19 2018-03-20 Daiichi Sankyo Company, Limited Method for improving dissolution of anticoagulant agent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0370415A1 (fr) * 1988-11-22 1990-05-30 Boehringer Ingelheim Kg Quinuclidines, leur utilisation comme médicaments et procédé pour leur préparation
WO1998030243A1 (fr) * 1997-01-08 1998-07-16 Warner-Lambert Company Inhibiteurs d'acetylcholinesterase en combinaison avec des agonistes muscariniques utilises dans le traitement de la maladie d'alzheimer
WO1998046601A1 (fr) * 1997-04-11 1998-10-22 Eli Lilly And Company Composition pour le traitement de la douleur
WO1998046225A1 (fr) * 1997-04-11 1998-10-22 Eli Lilly And Company Traitement contre la schizophrenie
DE19851126A1 (de) * 1998-11-06 2000-05-11 Boehringer Ingelheim Pharma Verwendung von Talsaclidin zur Behandlung der Schizophrenie

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0370415A1 (fr) * 1988-11-22 1990-05-30 Boehringer Ingelheim Kg Quinuclidines, leur utilisation comme médicaments et procédé pour leur préparation
WO1998030243A1 (fr) * 1997-01-08 1998-07-16 Warner-Lambert Company Inhibiteurs d'acetylcholinesterase en combinaison avec des agonistes muscariniques utilises dans le traitement de la maladie d'alzheimer
WO1998046601A1 (fr) * 1997-04-11 1998-10-22 Eli Lilly And Company Composition pour le traitement de la douleur
WO1998046225A1 (fr) * 1997-04-11 1998-10-22 Eli Lilly And Company Traitement contre la schizophrenie
DE19851126A1 (de) * 1998-11-06 2000-05-11 Boehringer Ingelheim Pharma Verwendung von Talsaclidin zur Behandlung der Schizophrenie

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2140867A4 (fr) * 2007-03-29 2013-07-03 Daiichi Sankyo Co Ltd Composition pharmaceutique
US9149532B2 (en) 2007-03-29 2015-10-06 Daiichi Sanykyo Company, Limited Pharmaceutical composition
US9707296B2 (en) 2007-03-29 2017-07-18 Daiichi Sankyo Company, Limited Pharmaceutical composition
EP2140867B1 (fr) 2007-03-29 2017-08-30 Daiichi Sankyo Company, Limited Composition pharmaceutique
WO2010033045A1 (fr) * 2008-09-16 2010-03-25 Igor Anatolievich Pomytkin Compositions et procédés pour la prévention ou le traitement d’un dépôt bêta-amyloïde
US9918975B2 (en) 2010-03-19 2018-03-20 Daiichi Sankyo Company, Limited Method for improving dissolution of anticoagulant agent
US9402907B2 (en) 2011-08-10 2016-08-02 Daiichi Sankyo Company, Limited Pharmaceutical composition containing diamine derivative

Also Published As

Publication number Publication date
DE10106971A1 (de) 2002-08-29
AU2002247705A1 (en) 2002-08-28
MXPA03007272A (es) 2003-12-04
AR033862A1 (es) 2004-01-07
CA2434976A1 (fr) 2002-08-22
WO2002064124A3 (fr) 2002-12-05
EP1361871A2 (fr) 2003-11-19
UY27170A1 (es) 2002-09-30
JP2004518710A (ja) 2004-06-24

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