CA2135535A1 - Medicinal formulations containing thioctic acid or dihydrolipoic acid in the form of inclusion compounds with cyclodextrins or cyclodextrin derivatives and in the form of granulates, chewable or effervescent tablets - Google Patents

Medicinal formulations containing thioctic acid or dihydrolipoic acid in the form of inclusion compounds with cyclodextrins or cyclodextrin derivatives and in the form of granulates, chewable or effervescent tablets

Info

Publication number
CA2135535A1
CA2135535A1 CA002135535A CA2135535A CA2135535A1 CA 2135535 A1 CA2135535 A1 CA 2135535A1 CA 002135535 A CA002135535 A CA 002135535A CA 2135535 A CA2135535 A CA 2135535A CA 2135535 A1 CA2135535 A1 CA 2135535A1
Authority
CA
Canada
Prior art keywords
acid
cyclodextrins
granulates
chewable
inclusion compounds
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.)
Granted
Application number
CA002135535A
Other languages
French (fr)
Other versions
CA2135535C (en
Inventor
Helmut Hettche
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.)
Meda Pharma GmbH and Co KG
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6502345&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2135535(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Publication of CA2135535A1 publication Critical patent/CA2135535A1/en
Application granted granted Critical
Publication of CA2135535C publication Critical patent/CA2135535C/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/26—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nanotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Ophthalmology & Optometry (AREA)
  • Materials Engineering (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Biochemistry (AREA)
  • Polymers & Plastics (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The unpleasant taste of thioctic acid or of dihydrolipoic acid is masked by incorporation in cyclodextrins. Medicinal forms are described. Inclusion compounds of enantiomerically pure dihydrolipoic acid and cyclodextrins are new. They are suitable for the preparation of medicaments.
CA002135535A 1993-11-11 1994-11-10 Medicinal formulations containing thioctic acid or dihydrolipoic acid in the form of inclusion compounds with cyclodextrins or cyclodextrin derivatives and in the form of granulates, chewable or effervescent tablets Expired - Lifetime CA2135535C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4338508A DE4338508A1 (en) 1993-11-11 1993-11-11 Pharmaceutical preparations containing thioctic acid or dihydroliponic acid in the form of inclusion compounds with cyclodextrins or cyclodextrin derivatives and in the form of granules, chewable or effervescent tablets
DEP4338508.7 1993-11-11

Publications (2)

Publication Number Publication Date
CA2135535A1 true CA2135535A1 (en) 1995-05-12
CA2135535C CA2135535C (en) 2006-03-21

Family

ID=6502345

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002135535A Expired - Lifetime CA2135535C (en) 1993-11-11 1994-11-10 Medicinal formulations containing thioctic acid or dihydrolipoic acid in the form of inclusion compounds with cyclodextrins or cyclodextrin derivatives and in the form of granulates, chewable or effervescent tablets

Country Status (8)

Country Link
EP (2) EP1063241A1 (en)
JP (1) JP3404435B2 (en)
AT (1) ATE238352T1 (en)
CA (1) CA2135535C (en)
DE (2) DE4338508A1 (en)
DK (1) DK0654484T3 (en)
ES (1) ES2194854T3 (en)
PT (1) PT654484E (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7737269B2 (en) 2004-12-17 2010-06-15 Wacker-Chemie Gmbh Process for preparing an alpha-lipoic acid/cyclodextrin complex and product prepared
US9265753B2 (en) 2011-08-31 2016-02-23 Jeffery Lee Benjamin, JR. Limited release lingual thioctic acid delivery systems
US10993929B2 (en) 2016-09-27 2021-05-04 Molecular Product Management, Llc ALA and salt formulation
US11510898B2 (en) 2016-02-22 2022-11-29 Molecular product management LLC Limited release lingual thioctic acid delivery systems

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19510130C1 (en) * 1995-03-21 1996-11-21 Asta Medica Ag Process for the preparation of free-flowing R, S-thioctic acid, R, S-thioctic acid and their use
DE19705555A1 (en) * 1997-02-13 1998-08-20 Ulrich Dr Posanski Thioctic acid pharmaceutical preparations for oral use
NZ330596A (en) * 1998-06-05 2001-02-23 Dec Res Intravaginal devices allowing for increased uptake of active ingredients
US6191162B1 (en) 1998-05-28 2001-02-20 Medical Research Institute Method of reducing serum glucose levels
US6905707B2 (en) 1998-05-28 2005-06-14 Medical Research Institute Controlled release arginine alpha ketoglutarate
US6197340B1 (en) 1998-05-28 2001-03-06 Medical Research Institute Controlled release lipoic acid
CN1144585C (en) * 2000-12-13 2004-04-07 华扩达动物科学[I.P.2]有限公司 Animal phisiologicla and biological activity regulation agent composition containing cysteamine and its salt
JP4849792B2 (en) * 2004-09-14 2012-01-11 オリザ油化株式会社 Cosmetic composition
EP1671653B1 (en) * 2004-12-17 2007-08-01 Wacker Chemie AG Process for preparing an alpha lipoic acid/cyclodextrin complex and product prepared
DE102004060914A1 (en) * 2004-12-17 2006-07-06 Bioghurt Biogarde Gmbh & Co. Kg Use of lipoic acid-containing cyclodextrin complexes
JP5011776B2 (en) * 2005-03-28 2012-08-29 大正製薬株式会社 Copper compound composition
JP5157001B2 (en) * 2005-04-30 2013-03-06 ビーエイチエヌ株式会社 Stabilized α-lipoic acid composition and use thereof
JP4951226B2 (en) * 2005-09-08 2012-06-13 立山化成株式会社 Method for producing α-lipoic acid alkali salt
JP5023311B2 (en) * 2005-11-06 2012-09-12 ビーエイチエヌ株式会社 Composition for improving and / or preventing skin disorders
JP2007177149A (en) * 2005-12-28 2007-07-12 Shield Lab:Kk Inclusion compound of thioctic acid or dihydrolipoic acid with branched cyclodextrin
JP5044767B2 (en) * 2006-01-28 2012-10-10 ビーエイチエヌ株式会社 Pigmentation inhibitor and use thereof
JP2009108019A (en) * 2007-10-30 2009-05-21 Bhn Kk External preparation for skin for enhancing ultraviolet resistivity
CN102892310B (en) * 2010-03-13 2016-07-06 伊斯顿庞德实验室有限公司 The compositions of bound fat
JPWO2012014746A1 (en) * 2010-07-30 2013-09-12 株式会社シクロケム Alpha lipoic acid complex
US20230331692A1 (en) * 2020-08-27 2023-10-19 Kyowa Pharma Chemical Co., Ltd. Trisulfide compound and clathrate thereof

Family Cites Families (15)

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GB1520942A (en) * 1976-02-10 1978-08-09 Ono Pharmaceutical Co Postaglandin analogues
HU176217B (en) * 1978-11-20 1981-01-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing a cyclodextrin-chamomille inclusion complex and compositions containing thereof
HU177081B (en) * 1978-12-12 1981-07-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing the occlusion complex of allicin with cyclodextrin
HU181703B (en) * 1980-05-09 1983-11-28 Chinoin Gyogyszer Es Vegyeszet Process for producing aqueus solutuins of water insoluble or hardly soluble vitamines, steroides, localanesthetics, prostanoides and non-steroid and antiphlogistic agents
HU190841B (en) * 1983-02-04 1986-11-28 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu Process for the production of cyclodextrin polymers swelling in water quickly and to a high extent
US4616008A (en) * 1984-05-02 1986-10-07 Takeda Chemical Industries, Ltd. Antibacterial solid composition for oral administration
MY106598A (en) * 1988-08-31 1995-06-30 Australian Commercial Res & Development Ltd Compositions and methods for drug delivery and chromatography.
DK0392608T3 (en) * 1989-04-12 1995-11-20 Procter & Gamble Solid Consumer Product Compositions Containing Cyclodextrin Complexes of Small Particle Size
GB8920135D0 (en) * 1989-09-06 1989-10-18 Erba Carlo Spa Use of dehydrated cyclodextrins for improving drug dissolution
ATE126053T1 (en) * 1989-11-09 1995-08-15 Asta Medica Ag MEDICINAL PRODUCTS WHICH CONTAIN CARBOXIC ACIDS CONTAINING SULFUR AS THE ACTIVE INGREDIENTS AND THEIR USE FOR FIGHTING RETROVIRUSES.
EP0812590A3 (en) * 1989-11-09 1999-06-09 ASTA Medica Aktiengesellschaft Use of R-alpha lipoic acid for cytoprotection
WO1991013100A1 (en) * 1990-03-02 1991-09-05 Australian Commercial Research & Development Limited Cyclodextrin compositions and methods for pharmaceutical and industrial applications
FR2659970A1 (en) * 1990-03-26 1991-09-27 Santerre Orsan Process for the preparation of inclusion compounds based on cyclodextrin and inclusion compounds obtained
US5139687A (en) * 1990-05-09 1992-08-18 The Proctor & Gamble Company Non-destructive carriers for cyclodextrin complexes
DE4218572A1 (en) * 1992-06-05 1993-12-09 Asta Medica Ag Synergistic combination of drugs containing as active ingredient alpha-lipoic acid, dihydrolipoic acid, their metabolites as well as the oxidized and reduced enantiomers of alpha-lipoic acid such as R-alpha-lipoic acid or S-alpha-lipoic acid and metabolites of alpha-lipoic acid with vitamins A, B1 -6, B12, C and E

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7737269B2 (en) 2004-12-17 2010-06-15 Wacker-Chemie Gmbh Process for preparing an alpha-lipoic acid/cyclodextrin complex and product prepared
US8481716B2 (en) 2004-12-17 2013-07-09 Wacker Chemie Ag Process for preparing an alpha-lipoic acid/cyclodextrin complex and product prepared
US9265753B2 (en) 2011-08-31 2016-02-23 Jeffery Lee Benjamin, JR. Limited release lingual thioctic acid delivery systems
US11510898B2 (en) 2016-02-22 2022-11-29 Molecular product management LLC Limited release lingual thioctic acid delivery systems
US10993929B2 (en) 2016-09-27 2021-05-04 Molecular Product Management, Llc ALA and salt formulation

Also Published As

Publication number Publication date
JP3404435B2 (en) 2003-05-06
DK0654484T3 (en) 2003-07-28
JPH07188304A (en) 1995-07-25
ES2194854T3 (en) 2003-12-01
EP0654484A3 (en) 1995-08-16
ATE238352T1 (en) 2003-05-15
EP1063241A1 (en) 2000-12-27
DE59410277D1 (en) 2003-05-28
EP0654484A2 (en) 1995-05-24
CA2135535C (en) 2006-03-21
EP0654484B1 (en) 2003-04-23
DE4338508A1 (en) 1995-05-18
PT654484E (en) 2003-08-29

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Effective date: 20141110