WO2002003960A1 - Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs - Google Patents

Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs Download PDF

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Publication number
WO2002003960A1
WO2002003960A1 PCT/FR2001/002159 FR0102159W WO0203960A1 WO 2002003960 A1 WO2002003960 A1 WO 2002003960A1 FR 0102159 W FR0102159 W FR 0102159W WO 0203960 A1 WO0203960 A1 WO 0203960A1
Authority
WO
WIPO (PCT)
Prior art keywords
heparin
particular vectors
polymer
poly
vectors according
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.)
Ceased
Application number
PCT/FR2001/002159
Other languages
English (en)
French (fr)
Inventor
Philippe Maincent
Nathalie Ubrich
Claude Vigneron
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.)
Individual
Original Assignee
Individual
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
Priority to DE60134147T priority Critical patent/DE60134147D1/de
Priority to EP01984141A priority patent/EP1313453B1/fr
Priority to CA2415414A priority patent/CA2415414C/fr
Priority to JP2002508415A priority patent/JP5175017B2/ja
Priority to MXPA03000193A priority patent/MXPA03000193A/es
Priority to US10/332,351 priority patent/US8052998B2/en
Priority to BRPI0112080A priority patent/BRPI0112080B1/pt
Priority to ES01984141T priority patent/ES2305121T3/es
Priority to DK01984141T priority patent/DK1313453T3/da
Priority to KR10-2003-7000198A priority patent/KR20030038655A/ko
Application filed by Individual filed Critical Individual
Priority to AU2002218745A priority patent/AU2002218745A1/en
Publication of WO2002003960A1 publication Critical patent/WO2002003960A1/fr
Anticipated expiration legal-status Critical
Priority to US12/779,556 priority patent/US8257744B2/en
Priority to US13/355,763 priority patent/US8361509B2/en
Ceased 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5138—Organic macromolecular compounds; Dendrimers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
    • A61K9/5153—Polyesters, e.g. poly(lactide-co-glycolide)
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Definitions

  • Heparin has been used for fifty years in the prevention and treatment of thromboembolic disease, but has the disadvantage of being particularly hemorrhagic and of requiring strict biological and clinical monitoring.
  • thromboembolic disease Apart from functional abnormalities of hemostasis which lead to a state of hypercoagulability (congenital or acquired deficiency in anti-thrombin III, cofactor II, proteins C and S), there are various risk factors for thromboembolic disease defined as a a set of hemostasis disorders leading to the formation of a fibrin clot or platelet nails in the lumen of a blood vessel.
  • Oil-in-water (O / W) emulsions or micellar solutions of monoolein salts intended to increase the absorption of heparin have also been considered (Taniguchi et al., Int. X Pharm., 4, (1980), 219-228).
  • Propylene glycol solutions containing heparin and compounds derived from the N-acylation of the aromatic amino acid, 4-aminophenylbutyric acid have shown improvement in gastrointestinal absorption and bioavailability of heparin after administration oral to rats and monkeys (Leone-Bay et al., 3. Controlled Red., 50, (1998), 41-49).
  • the polymer matrix can also comprise one or more substances chosen from the group comprising enteric polymers, surfactants and water-soluble or liposoluble substances.
  • the standard or low molecular weight heparin solution (1 ml, 5,000 IU) is emulsified using an ultrasound probe for 3 min in a dichloromethane solution (10 ml) containing the polymer or blend of polymers (250 mg).
  • This first emulsion (water / oil) is then poured in a volume of water (200 ml) containing a surfactant, polyvinyl alcohol (0.1%), making it possible to obtain, by pressure homogenization (die homogenizer), a second water / oil / water emulsion.
  • the stirring is stopped and the solvent is evaporated from the colloidal suspension in an evaporator under reduced pressure, causing the formation of polymer nanoparticles in suspension in water.
  • the suspension of the nanoparticles is washed 3 three by centrifugation (25000 g). This suspension can be used as it is or freeze-dried.
  • the particles have an average size of 250 nm.

Landscapes

  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Physics & Mathematics (AREA)
  • Diabetes (AREA)
  • Optics & Photonics (AREA)
  • Nanotechnology (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
PCT/FR2001/002159 2000-07-07 2001-07-05 Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs Ceased WO2002003960A1 (fr)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DK01984141T DK1313453T3 (da) 2000-07-07 2001-07-05 Partikelformige bærere til at forbedre oral absorbtion af aktive stoffer
CA2415414A CA2415414C (fr) 2000-07-07 2001-07-05 Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs
JP2002508415A JP5175017B2 (ja) 2000-07-07 2001-07-05 有効成分の経口吸収を改善するための粒子状担体
MXPA03000193A MXPA03000193A (es) 2000-07-07 2001-07-05 Vectores en particulas para mejorar la absorcion oral de los principios activos.
US10/332,351 US8052998B2 (en) 2000-07-07 2001-07-05 Particulate vectors for improving oral absorption of active principles
BRPI0112080A BRPI0112080B1 (pt) 2000-07-07 2001-07-05 vetores particulados para aperfeiçoamento da absorção oral de principios ativos
ES01984141T ES2305121T3 (es) 2000-07-07 2001-07-05 Vectores en forma de particulas destinados a mejorar la absorcion oral de principios activos.
DE60134147T DE60134147D1 (de) 2000-07-07 2001-07-05 Träger in partikelform zur verbesserung der oral- absorption von wikstoffen
EP01984141A EP1313453B1 (fr) 2000-07-07 2001-07-05 Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs
KR10-2003-7000198A KR20030038655A (ko) 2000-07-07 2001-07-05 유효성분의 경구 흡수를 개선하기 위한 미립자 벡터
AU2002218745A AU2002218745A1 (en) 2000-07-07 2001-07-05 Particulate vectors for improving oral absorption of active principles
US12/779,556 US8257744B2 (en) 2000-07-07 2010-05-13 Pharmaceutical forms for the release of active compounds
US13/355,763 US8361509B2 (en) 2000-07-07 2012-01-23 Pharmaceutical dosage forms for the release of active compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR00/08902 2000-07-07
FR0008902A FR2811227A1 (fr) 2000-07-07 2000-07-07 Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US10332351 A-371-Of-International 2001-07-05
US10/332,351 Continuation US8052998B2 (en) 2000-07-07 2001-07-05 Particulate vectors for improving oral absorption of active principles
PCT/EP2008/065499 Continuation-In-Part WO2009063021A1 (en) 2000-07-07 2008-11-13 Pharmaceutical forms for the release of active compounds

Publications (1)

Publication Number Publication Date
WO2002003960A1 true WO2002003960A1 (fr) 2002-01-17

Family

ID=8852251

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2001/002159 Ceased WO2002003960A1 (fr) 2000-07-07 2001-07-05 Vecteurs particulaires destines a ameliorer l'absorption orale de principes actifs

Country Status (17)

Country Link
US (1) US8052998B2 (https=)
EP (1) EP1313453B1 (https=)
JP (1) JP5175017B2 (https=)
KR (1) KR20030038655A (https=)
CN (1) CN1440277A (https=)
AT (1) ATE395906T1 (https=)
AU (1) AU2002218745A1 (https=)
BR (1) BRPI0112080B1 (https=)
CA (1) CA2415414C (https=)
DE (1) DE60134147D1 (https=)
DK (1) DK1313453T3 (https=)
ES (1) ES2305121T3 (https=)
FR (1) FR2811227A1 (https=)
MX (1) MXPA03000193A (https=)
PT (1) PT1313453E (https=)
RU (1) RU2003103596A (https=)
WO (1) WO2002003960A1 (https=)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2060253A1 (en) * 2007-11-14 2009-05-20 Laboratorios Farmaceuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
EP2213282A1 (en) * 2009-01-30 2010-08-04 Laboratorios Farmaceuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
DE102012019029A1 (de) 2012-09-27 2014-03-27 Alf Lamprecht Arzneiformulierungen zur oralen Gabe von therapeutischen Substanzen und Verfahren zur Herstellung
US8802156B2 (en) 2007-11-14 2014-08-12 Laboratorios Farmacéuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds

Families Citing this family (26)

* Cited by examiner, † Cited by third party
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US8257744B2 (en) 2000-07-07 2012-09-04 Laboratorios Farmacéuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
BE1015608A6 (fr) * 2003-07-15 2005-06-07 Messadek Jallal Traitement des arterites.
DE602004003577T2 (de) * 2003-04-17 2007-09-20 Jallal Messadek Flottierende orale Formulierungen mit kontrollierter Freisetzung von Betain
US20060128657A1 (en) * 2003-08-04 2006-06-15 Jallal Messadek Selected betaines and their uses
WO2006088647A1 (en) * 2005-02-17 2006-08-24 Medivas, Llc Polymer particle delivery compositions and methods of use
EP1730516A1 (en) * 2004-03-30 2006-12-13 Pfizer Products Incorporated Method and device for evaluation of pharmaceutical compositions
BE1016128A6 (fr) * 2004-07-22 2006-03-07 Messadek Jallal Combinaisons therapeutiques
WO2006050581A2 (en) * 2004-11-10 2006-05-18 Jallal Messadek Betaine as agent against arthropod - or mosquito -borne diseases
BRPI0610249A2 (pt) * 2005-04-27 2010-06-08 Jallal Messadek associação ou combinação farmacêutica, composição farmacêutica, processo de co-cristalização e o uso de insulina ou análogo de insulina
CA2623239C (en) 2005-09-22 2016-07-12 Medivas, Llc Solid polymer delivery compositions and methods for use thereof
WO2008065502A1 (en) * 2006-11-29 2008-06-05 Pfizer Products Inc. Pharmaceutical compositions based on a) nanoparticles comprising enteric polymers and b) casein
US20100119612A1 (en) * 2007-04-17 2010-05-13 Bend Research, Inc Nanoparticles comprising non-crystalline drug
WO2008135855A2 (en) * 2007-05-03 2008-11-13 Pfizer Products Inc. Nanoparticles comprising a cholesteryl ester transfer protein inhibitor and a nonionizable polymer
WO2008135828A2 (en) * 2007-05-03 2008-11-13 Pfizer Products Inc. Nanoparticles comprising a drug, ethylcellulose, and a bile salt
WO2008135852A2 (en) * 2007-05-03 2008-11-13 Pfizer Products Inc. Pharmaceutical compositions comprising nanoparticles and casein
US9545384B2 (en) 2007-06-04 2017-01-17 Bend Research, Inc. Nanoparticles comprising drug, a non-ionizable cellulosic polymer and tocopheryl polyethylene glocol succinate
EP2162120B1 (en) * 2007-06-04 2016-05-04 Bend Research, Inc Nanoparticles comprising a non-ionizable cellulosic polymer and an amphiphilic non-ionizable block copolymer
US20100215747A1 (en) * 2007-07-13 2010-08-26 Corey Jay Bloom Nanoparticles comprising ionizable, poorly water soluble cellulosic polymers
WO2009065193A1 (en) * 2007-11-21 2009-05-28 Jallal Messadek Treatment of aspirin resistance with betaine and/or betaine enriched molasses
US9233078B2 (en) * 2007-12-06 2016-01-12 Bend Research, Inc. Nanoparticles comprising a non-ionizable polymer and an Amine-functionalized methacrylate copolymer
WO2009073215A1 (en) * 2007-12-06 2009-06-11 Bend Research, Inc. Pharmaceutical compositions comprising nanoparticles and a resuspending material
US9101547B2 (en) * 2011-08-04 2015-08-11 Nano And Advanced Materials Institute Limited Enteric-coated capsule containing cationic nanoparticles for oral insulin delivery
CA3015172A1 (en) 2016-02-18 2017-08-24 Privo Technologies, Inc. Two-stage microparticle-based therapeutic delivery system and method
US20180235899A1 (en) 2017-02-17 2018-08-23 Privo Technologies, Inc. Particle-based multi-layer therapeutic delivery device and method
US10478403B1 (en) 2017-05-03 2019-11-19 Privo Technologies, Inc. Intraoperative topically-applied non-implantable rapid release patch
KR20240041285A (ko) 2021-06-01 2024-03-29 프리보 테크놀로지스, 인코포레이티드 향상된 2단계 미세입자 기반 국소 치료제 전달 시스템

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WO1992011844A1 (en) * 1991-01-03 1992-07-23 Alkermes Controlled Therapeutics, Inc. Stabilization of proteins by cationic biopolymers
WO1994014420A1 (en) * 1992-12-21 1994-07-07 Emisphere Technologies, Inc. Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof
WO1996028143A1 (de) * 1995-03-10 1996-09-19 Boehringer Mannheim Gmbh Polypeptid-enthaltende pharmazeutische darreichungsformen in form von mikropartikeln und verfahren zu deren herstellung
FR2769853A1 (fr) * 1997-10-21 1999-04-23 Prographarm Lab Nouveau procede d'obtention de microspheres et les produits ainsi realises

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AT397345B (de) * 1990-04-04 1994-03-25 Chemiefaser Lenzing Ag Pharmazeutisches präparat mit verzögerter wirkstofffreisetzung auf basis von hemicellulosen
ATE154241T1 (de) * 1991-10-01 1997-06-15 Takeda Chemical Industries Ltd Mikropartikeln-zusammenfassung zur verlängerten freigabe und herstellung derselbe
GB9202464D0 (en) * 1992-02-05 1992-03-18 Danbiosyst Uk Composition for nasal administration
DE4220782A1 (de) * 1992-06-25 1994-01-05 Basf Ag Verfahren zur Herstellung von festen pharmazeutischen Retardformen
GB9412273D0 (en) * 1994-06-18 1994-08-10 Univ Nottingham Administration means
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HK1040910B (en) * 1998-11-12 2009-06-26 Smithkline Beecham Plc Pharmaceutical composition for modified release of an insulin sensitiser and metformin
AU3471400A (en) * 1999-01-19 2000-08-07 Children's Hospital Of Philadelphia, The Compositions and methods for controlled delivery of virus vectors

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
WO1992011844A1 (en) * 1991-01-03 1992-07-23 Alkermes Controlled Therapeutics, Inc. Stabilization of proteins by cationic biopolymers
WO1994014420A1 (en) * 1992-12-21 1994-07-07 Emisphere Technologies, Inc. Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof
WO1996028143A1 (de) * 1995-03-10 1996-09-19 Boehringer Mannheim Gmbh Polypeptid-enthaltende pharmazeutische darreichungsformen in form von mikropartikeln und verfahren zu deren herstellung
FR2769853A1 (fr) * 1997-10-21 1999-04-23 Prographarm Lab Nouveau procede d'obtention de microspheres et les produits ainsi realises

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2060253A1 (en) * 2007-11-14 2009-05-20 Laboratorios Farmaceuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
WO2009063021A1 (en) * 2007-11-14 2009-05-22 Laboratorios Farmacéuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
US8802156B2 (en) 2007-11-14 2014-08-12 Laboratorios Farmacéuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
EP2213282A1 (en) * 2009-01-30 2010-08-04 Laboratorios Farmaceuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
WO2010086425A1 (en) * 2009-01-30 2010-08-05 Laboratorios Farmacéuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
WO2010086427A1 (en) * 2009-01-30 2010-08-05 Laboratorios Farmacéuticos Rovi, S.A. Pharmaceutical forms for the release of active compounds
DE102012019029A1 (de) 2012-09-27 2014-03-27 Alf Lamprecht Arzneiformulierungen zur oralen Gabe von therapeutischen Substanzen und Verfahren zur Herstellung

Also Published As

Publication number Publication date
CA2415414A1 (fr) 2002-01-17
DK1313453T3 (da) 2008-09-22
RU2003103596A (ru) 2004-08-20
ATE395906T1 (de) 2008-06-15
CA2415414C (fr) 2011-08-23
BR0112080A (pt) 2003-05-06
BRPI0112080B1 (pt) 2017-01-24
PT1313453E (pt) 2008-07-16
EP1313453A1 (fr) 2003-05-28
MXPA03000193A (es) 2004-09-13
ES2305121T3 (es) 2008-11-01
EP1313453B1 (fr) 2008-05-21
JP2004502720A (ja) 2004-01-29
AU2002218745A1 (en) 2002-01-21
JP5175017B2 (ja) 2013-04-03
US20050013866A1 (en) 2005-01-20
CN1440277A (zh) 2003-09-03
FR2811227A1 (fr) 2002-01-11
US8052998B2 (en) 2011-11-08
KR20030038655A (ko) 2003-05-16
DE60134147D1 (de) 2008-07-03

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