WO2008055996A1 - Oral dosage form comprising tri-substituted glycerol compounds - Google Patents

Oral dosage form comprising tri-substituted glycerol compounds Download PDF

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Publication number
WO2008055996A1
WO2008055996A1 PCT/EP2007/062180 EP2007062180W WO2008055996A1 WO 2008055996 A1 WO2008055996 A1 WO 2008055996A1 EP 2007062180 W EP2007062180 W EP 2007062180W WO 2008055996 A1 WO2008055996 A1 WO 2008055996A1
Authority
WO
WIPO (PCT)
Prior art keywords
dosage form
solid dosage
pharmaceutical solid
tri
form 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/EP2007/062180
Other languages
English (en)
French (fr)
Inventor
Wolfgang Richter
Lutz Weber
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.)
Alphaptose GmbH
Original Assignee
Alphaptose GmbH
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 AU2007316588A priority Critical patent/AU2007316588B2/en
Priority to US12/514,390 priority patent/US20110110984A1/en
Priority to DK07822468.0T priority patent/DK2091520T3/da
Priority to ES07822468T priority patent/ES2382756T3/es
Priority to EP07822468A priority patent/EP2091520B1/en
Priority to CA2668919A priority patent/CA2668919C/en
Application filed by Alphaptose GmbH filed Critical Alphaptose GmbH
Priority to AT07822468T priority patent/ATE546133T1/de
Priority to JP2009535750A priority patent/JP5352466B2/ja
Publication of WO2008055996A1 publication Critical patent/WO2008055996A1/en
Anticipated expiration legal-status Critical
Priority to US15/439,443 priority patent/US20170157150A1/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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
    • 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
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • 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
    • A61K31/66—Phosphorus compounds
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
    • A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2009—Inorganic compounds
    • 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
    • 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
    • A61K9/2027—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
    • A61K9/20—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
    • 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
    • A61K9/2063—Proteins, e.g. gelatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators

Definitions

  • the tri-substituted glycerol compounds of formula (I) are present in the dosage form as pharmaceutically acceptable salts.
  • Such salts may comprise any pharmaceutically acceptable anion "neutralizing" the positive charge of the nitrogen (e.g. chloride, bromide or iodide) or any pharmaceutically acceptable cation "neutralizing" the negative charge of the phosphate or sulfate moiety (e.g. sodium or potassium cations).
  • the stabilizer is typically contained in the film coating material in an amount of about 1% (w/w) to 5% (w/w), based on the total weight of the film coating.
  • the pharmaceutical solid dosage form provides for immediate release of the tri-substituted glycerol compound upon being dissolved and/or disintegrated. It is desirable that the inventive pharmaceutical dosage form provides a defined, preferably rapid release profile. More precisely, the inventive dosage form may be formulated such that at least 80%, preferably at least 85%, of the total amount of the tri-substituted glycerol compound comprised in the dosage form is released from the dosage form within 45 minutes, preferably within 30 minutes, when measured in a type 1 dissolution apparatus (paddle) according to U.S.
  • the active agent, the tri- substituted glycerol compound may be contained or dispersed in a matrix being part of the dosage form.
  • the matrix of the inventive dosage form may preferably be an immediate release matrix, although also normal release or controlled release matrices having a coating that controls the release of the drug may be used.
  • Suitable materials for a controlled release matrix or coating comprise:
  • l-O-octadecyl-2-O-methyl-glycero-3-phosphocholine, Avicel, and diacalcium phosphate were passed through a sieve having a pore size of IV (about 1 mm) and thoroughly mixed. Crospovidone and magnesium stearate were also sieved and admixed. Subsequently, the tablets were compressed in a Korsch eccentric press EKO or XPl (Korsch AG, Berlin, Germany; the compression forces used were between 5 kN and 20 kN) in a hardness grade (i.e. breaking strength) of 90 N.
  • Example 10 Preparation of an inventive granulated tablet
  • siliciumdioxide does not show any interaction with l-O-octadecyl-2- O-methyl-glycero-3-phosphocholine (i.e. represents an inert inorganic material), whereas lactose, crospovidone, and starch all show such interactions. Interactions were also detected when using microcrystalline cellulose, calciumphosphate, and croscarmellose as excipients (data not shown). On the other hand, magnesium stearate and sodium stearylfumarate dominate the thermogram.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Inorganic Chemistry (AREA)
  • Immunology (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)
  • Medical Preparation Storing Or Oral Administration Devices (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/EP2007/062180 2006-11-10 2007-11-09 Oral dosage form comprising tri-substituted glycerol compounds Ceased WO2008055996A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US12/514,390 US20110110984A1 (en) 2006-11-10 2007-11-09 Oral Dosage Form Comprising Tri-Substituted Glycerol Compounds
DK07822468.0T DK2091520T3 (da) 2006-11-10 2007-11-09 Oral doseringsform omfattende trisubstituerede glycerol-forbindelser
ES07822468T ES2382756T3 (es) 2006-11-10 2007-11-09 Forma de dosificación oral que comprende compuestos de glicerol trisustituido
EP07822468A EP2091520B1 (en) 2006-11-10 2007-11-09 Oral dosage form comprising tri-substituted glycerol compounds
CA2668919A CA2668919C (en) 2006-11-10 2007-11-09 Oral dosage form comprising tri-substituted glycerol compounds
AU2007316588A AU2007316588B2 (en) 2006-11-10 2007-11-09 Oral dosage form comprising tri-substituted glycerol compounds
AT07822468T ATE546133T1 (de) 2006-11-10 2007-11-09 Orale dosierform mit trisubstituierten glycerin- verbindungen
JP2009535750A JP5352466B2 (ja) 2006-11-10 2007-11-09 トリ置換グリセロール化合物を含む経口投与剤形、経口投与剤形の調製方法、経口投与剤形の使用方法
US15/439,443 US20170157150A1 (en) 2006-11-10 2017-02-22 Oral dosage form comprising tri-substituted glycerol compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US85815706P 2006-11-10 2006-11-10
US60/858,157 2006-11-10

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/514,390 A-371-Of-International US20110110984A1 (en) 2006-11-10 2007-11-09 Oral Dosage Form Comprising Tri-Substituted Glycerol Compounds
US15/439,443 Continuation US20170157150A1 (en) 2006-11-10 2017-02-22 Oral dosage form comprising tri-substituted glycerol compounds

Publications (1)

Publication Number Publication Date
WO2008055996A1 true WO2008055996A1 (en) 2008-05-15

Family

ID=39092201

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/062180 Ceased WO2008055996A1 (en) 2006-11-10 2007-11-09 Oral dosage form comprising tri-substituted glycerol compounds

Country Status (11)

Country Link
US (2) US20110110984A1 (enExample)
EP (1) EP2091520B1 (enExample)
JP (1) JP5352466B2 (enExample)
CN (2) CN101610758A (enExample)
AT (1) ATE546133T1 (enExample)
AU (1) AU2007316588B2 (enExample)
CA (1) CA2668919C (enExample)
DK (1) DK2091520T3 (enExample)
ES (1) ES2382756T3 (enExample)
RU (1) RU2009121838A (enExample)
WO (1) WO2008055996A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1745788A1 (de) * 2005-07-22 2007-01-24 KTB Tumorforschungsgesellschaft mbH Acylglycerophospholipide zur Behandlung von Krebs und Tumorkachexie
WO2008074572A1 (en) * 2006-12-20 2008-06-26 Universitätsklinikum Hamburg-Eppendorf Use of tri-substituted glycerol compounds for the treatment of hematological malignancies
EP1952803A1 (en) * 2007-01-23 2008-08-06 KTB-Tumorforschungs GmbH Solid pharmaceutical dosage form containing hydrogenated phospholipids

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2619686A1 (de) 1976-05-04 1977-11-24 Max Planck Gesellschaft Anti-tumormittel
WO1987001257A2 (fr) 1985-08-28 1987-03-12 Max-Planck-Gesellschaft Zur Förderung Der Wissensc Agent contre la sclerose multiple
WO1990014829A1 (de) 1989-06-02 1990-12-13 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Lysolecithinderivate zur behandlung von autoimmunerkrankungen
WO1991009590A1 (de) 1990-01-03 1991-07-11 Medmark Pharma Gmbh Intravenös applizierbare pharmazeutische zubereitung von et18-och¿3?
WO1999030690A1 (en) * 1997-12-15 1999-06-24 Axia Therapeutics, Inc. Oral delivery formulation
DE19822509A1 (de) * 1998-05-19 1999-11-25 Medmark Pharma Gmbh Edelfosin zur Behandlung von Hirntumoren
WO2000001392A1 (de) 1998-07-01 2000-01-13 Medmark Pharma Gmbh 1-octadecyl-2-methyl-sn-glycero-3-phosphocholin (et180ch3) zur behandlung von humanen mammakarzinomen
US20040138263A1 (en) * 2002-11-14 2004-07-15 D'angio Paul Pharmaceutical compositions and dosage forms of thalidomide

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DE3827974A1 (de) * 1988-08-18 1990-02-22 Boehringer Mannheim Gmbh Kombinationspraeparate von proteinkinase-c-inhibitoren mit lipiden, lipid-analoga, cytostatica oder inhibitoren von phospholipasen
JP2002532553A (ja) * 1998-12-21 2002-10-02 インケイサ．ソシエダ アノニマ 有害な胃腸副作用を引き起こさない有力な抗炎症剤としてのエーテルリゾリン脂質の使用
JP2005517690A (ja) * 2002-02-01 2005-06-16 ファイザー・プロダクツ・インク 固体薬物分散物を含有する即時放出剤形

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2619686A1 (de) 1976-05-04 1977-11-24 Max Planck Gesellschaft Anti-tumormittel
WO1987001257A2 (fr) 1985-08-28 1987-03-12 Max-Planck-Gesellschaft Zur Förderung Der Wissensc Agent contre la sclerose multiple
WO1990014829A1 (de) 1989-06-02 1990-12-13 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Lysolecithinderivate zur behandlung von autoimmunerkrankungen
WO1991009590A1 (de) 1990-01-03 1991-07-11 Medmark Pharma Gmbh Intravenös applizierbare pharmazeutische zubereitung von et18-och¿3?
WO1999030690A1 (en) * 1997-12-15 1999-06-24 Axia Therapeutics, Inc. Oral delivery formulation
DE19822509A1 (de) * 1998-05-19 1999-11-25 Medmark Pharma Gmbh Edelfosin zur Behandlung von Hirntumoren
WO1999059599A1 (de) 1998-05-19 1999-11-25 Medmark Pharma Gmbh Edelfosin zur behandlung von hirntumoren
WO2000001392A1 (de) 1998-07-01 2000-01-13 Medmark Pharma Gmbh 1-octadecyl-2-methyl-sn-glycero-3-phosphocholin (et180ch3) zur behandlung von humanen mammakarzinomen
US20040138263A1 (en) * 2002-11-14 2004-07-15 D'angio Paul Pharmaceutical compositions and dosage forms of thalidomide

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ARTHUR, G.; BITTMAN, R., BIOCHIM. BIOPHYS. ACTA, vol. 1390, 1998, pages 85 - 102
CROWDER, T.M. ET AL.: "A Guide to Pharmaceutical Particulate Science", 2003, INTERPHARM/CRC
DRINGS, P. ET AL., ONKOLOGIE, vol. 15, 1992, pages 375 - 382
FRESHNEY, R.I.: "Culture of Animal Cells: A Manual of Basic Technique", 1994, WILEY-LISS.
GENNARO, A.L.; GENNARO, A.R.: "Remington: The Science and Practice of Pharmacy", 2000, LIPPINCOTT WILLIAMS & WILKINS
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PINCHUK A N ET AL: "SYNTHESIS OF ALKYL GLYCEROPHOSPHOLIPIDS THROUGH 1-0-BENZYL-2-0-METHYL-rac-GLYCEROL", PHARMACEUTICAL CHEMISTRY JOURNAL, CONSULTANTS BUREAU, NAW YORK, NY, US, vol. 26, 1992, pages 174 - 176, XP008087544, ISSN: 0091-150X *
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Also Published As

Publication number Publication date
ES2382756T3 (es) 2012-06-13
EP2091520B1 (en) 2012-02-22
US20170157150A1 (en) 2017-06-08
CA2668919A1 (en) 2008-05-15
AU2007316588A1 (en) 2008-05-15
ATE546133T1 (de) 2012-03-15
AU2007316588B2 (en) 2013-11-21
DK2091520T3 (da) 2012-06-18
CN103816127A (zh) 2014-05-28
CN101610758A (zh) 2009-12-23
EP2091520A1 (en) 2009-08-26
CA2668919C (en) 2015-11-03
JP2010509293A (ja) 2010-03-25
RU2009121838A (ru) 2010-12-20
JP5352466B2 (ja) 2013-11-27
US20110110984A1 (en) 2011-05-12

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