WO2008014787A1 - Branched hyaluronic acid and method of manufacture - Google Patents

Branched hyaluronic acid and method of manufacture Download PDF

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Publication number
WO2008014787A1
WO2008014787A1 PCT/DK2007/000358 DK2007000358W WO2008014787A1 WO 2008014787 A1 WO2008014787 A1 WO 2008014787A1 DK 2007000358 W DK2007000358 W DK 2007000358W WO 2008014787 A1 WO2008014787 A1 WO 2008014787A1
Authority
WO
WIPO (PCT)
Prior art keywords
hyaluronic acid
composition
branched
glucosamine
branched hyaluronic
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/DK2007/000358
Other languages
English (en)
French (fr)
Inventor
Kristoffer Toemmeraas
Khadija Schwach-Abdellaoui
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.)
Novozymes Biopharma DK AS
Original Assignee
Novozymes Biopolymer AS
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 Novozymes Biopolymer AS filed Critical Novozymes Biopolymer AS
Priority to JP2009522088A priority Critical patent/JP2009545637A/ja
Priority to EP07785725A priority patent/EP2049572A1/en
Priority to CA002657823A priority patent/CA2657823A1/en
Priority to AU2007280846A priority patent/AU2007280846B2/en
Priority to US12/375,425 priority patent/US8202986B2/en
Priority to CN2007800291575A priority patent/CN101501075B/zh
Publication of WO2008014787A1 publication Critical patent/WO2008014787A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/728—Hyaluronic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • glycosaminoglycans are unbranched carbohydrate polymers, consisting of repeating disaccharide units (only keratan sulphate is branched in the core region of the carbohydrate).
  • the disaccharide units generally comprise, as a first saccharide unit, one of two modified sugars - N-acetylgalactosamine (GaINAc) or N-acetylglucosamine (GIcNAc).
  • the second unit is usually an uronic acid, such as glucuronic acid (GIcUA) or iduronate.
  • hyaluronic acid is in fact usually used as meaning a whole series of polysaccharides with alternating residues of D-glucuronic and N-acetyl-D-glucosamine acids with varying molecular weights or even the degraded fractions of the same, and it would therefore seem more correct to use the plural term of "hyaluronic acids".
  • the singular term will, however, be used all the same in this description; in addition, the abbreviation "HA" will frequently be used in place of this collective term.
  • the hyaluronan of a recombinant Bacillus cell is expressed directly to the culture medium, a simple process may be used to isolate the hyaluronan from the culture medium.
  • the Bacillus cells and cellular debris are physically removed from the culture medium.
  • the culture medium may be diluted first, if desired, to reduce the viscosity of the medium.
  • Many methods are known to those skilled in the art for removing cells from culture medium, such as centrifugation or microfiltration. If desired, the remaining supernatant may then be filtered, such as by ultrafiltration, to concentrate and remove small molecule contaminants from the hyaluronan.
  • the first aspect of the invention relates to a branched hyaluronic acid, wherein the linear backbone comprises hyaluronic acid in which one or more ⁇ /-Acetyl-Glucosamine has been deacetylated to Glucosamine, with branching sidechain(s) covalently linked to the primary amine(s) of said deacetylated Glucosamine thus forming a secondary amine(s).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Toxicology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Absorbent Articles And Supports Therefor (AREA)
  • Medical Preparation Storing Or Oral Administration Devices (AREA)
  • Materials For Medical Uses (AREA)
PCT/DK2007/000358 2006-08-04 2007-07-13 Branched hyaluronic acid and method of manufacture Ceased WO2008014787A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2009522088A JP2009545637A (ja) 2006-08-04 2007-07-13 分岐ヒアルロン酸及びその製造方法
EP07785725A EP2049572A1 (en) 2006-08-04 2007-07-13 Branched hyaluronic acid and method of manufacture
CA002657823A CA2657823A1 (en) 2006-08-04 2007-07-13 Branched hyaluronic acid and method of manufacture
AU2007280846A AU2007280846B2 (en) 2006-08-04 2007-07-13 Branched hyaluronic acid and method of manufacture
US12/375,425 US8202986B2 (en) 2006-08-04 2007-07-13 Branched hyaluronic acid and method of manufacture
CN2007800291575A CN101501075B (zh) 2006-08-04 2007-07-13 支化透明质酸和制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DKPA200601034 2006-08-04
DKPA200601034 2006-08-04

Publications (1)

Publication Number Publication Date
WO2008014787A1 true WO2008014787A1 (en) 2008-02-07

Family

ID=38659373

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK2007/000358 Ceased WO2008014787A1 (en) 2006-08-04 2007-07-13 Branched hyaluronic acid and method of manufacture

Country Status (7)

Country Link
US (1) US8202986B2 (https=)
EP (1) EP2049572A1 (https=)
JP (1) JP2009545637A (https=)
CN (1) CN101501075B (https=)
AU (1) AU2007280846B2 (https=)
CA (1) CA2657823A1 (https=)
WO (1) WO2008014787A1 (https=)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015135511A1 (en) 2014-03-11 2015-09-17 Contipro Biotech S.R.O. Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof
WO2016202314A1 (en) 2015-06-15 2016-12-22 Contipro A.S. Method of crosslinking of polysaccharides using photoremovable protecting groups
US9999678B2 (en) 2012-11-27 2018-06-19 Contipro A.S. C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof
US10363595B2 (en) 2014-06-09 2019-07-30 Hyperion Materials & Technologies (Sweden) Ab Cemented carbide necking tool
US10414832B2 (en) 2015-06-26 2019-09-17 Contipro A.S Derivatives of sulfated polysaccharides, method of preparation, modification and use thereof
US10617711B2 (en) 2014-06-30 2020-04-14 Contipro A.S. Antitumor composition based on hyaluronic acid and inorganic nanoparticles, method of preparation thereof and use thereof
US10618984B2 (en) 2016-06-27 2020-04-14 Contipro A.S. Unsaturated derivatives of polysaccharides, method of preparation thereof and use thereof
US10689464B2 (en) 2015-03-09 2020-06-23 Contipro A.S. Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of preparation and use thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI561535B (en) 2011-10-06 2016-12-11 Bvw Holding Ag Copolymers of hydrophobic and hydrophilic segments that reduce protein adsorption
KR101969446B1 (ko) * 2017-06-30 2019-04-16 한양대학교 산학협력단 히알루론산 기반 보습 소재

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EP0694616A2 (en) 1994-07-26 1996-01-31 POLI INDUSTRIA CHIMICA S.p.A. Process for the preparation of hyaluronic acid by fermentation with streptococcus
WO1999023227A2 (en) 1997-10-31 1999-05-14 The Board Of Regents Of The University Of Oklahoma Hyaluronan synthase gene and uses thereof
WO1999051265A1 (en) 1998-04-02 1999-10-14 Board Of Regents Of The Universtiy Of Oklahoma Nucleic acid encoding hyaluronan synthase and methods of use
US6020484A (en) 1995-12-20 2000-02-01 Fidia Advanced Biopolymers S.R.L. Process for preparing a hyaluronic acid fraction having a low polydispersion index
WO2000027437A2 (en) 1998-11-11 2000-05-18 The Board Of Regents Of The University Of Oklahoma Polymer grafting by polysaccharide synthases
WO2003054163A2 (en) 2001-12-21 2003-07-03 Novozymes Biopolymer A/S Methods for producing hyaluronan in a recombinant host cell
WO2004022603A1 (en) * 2002-09-03 2004-03-18 Lg Life Sciences Ltd. Hyaluronic acid derivatives and processes for preparing the same

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JP2739232B2 (ja) * 1989-04-14 1998-04-15 チッソ株式会社 生物学的親和性を有するセルロースゲルの使用方法
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US4801539A (en) 1984-05-25 1989-01-31 Shiseido Company Ltd. Fermentation method for producing hyaluronic acid
EP0694616A2 (en) 1994-07-26 1996-01-31 POLI INDUSTRIA CHIMICA S.p.A. Process for the preparation of hyaluronic acid by fermentation with streptococcus
US6020484A (en) 1995-12-20 2000-02-01 Fidia Advanced Biopolymers S.R.L. Process for preparing a hyaluronic acid fraction having a low polydispersion index
WO1999023227A2 (en) 1997-10-31 1999-05-14 The Board Of Regents Of The University Of Oklahoma Hyaluronan synthase gene and uses thereof
WO1999051265A1 (en) 1998-04-02 1999-10-14 Board Of Regents Of The Universtiy Of Oklahoma Nucleic acid encoding hyaluronan synthase and methods of use
WO2000027437A2 (en) 1998-11-11 2000-05-18 The Board Of Regents Of The University Of Oklahoma Polymer grafting by polysaccharide synthases
WO2003054163A2 (en) 2001-12-21 2003-07-03 Novozymes Biopolymer A/S Methods for producing hyaluronan in a recombinant host cell
WO2004022603A1 (en) * 2002-09-03 2004-03-18 Lg Life Sciences Ltd. Hyaluronic acid derivatives and processes for preparing the same

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9999678B2 (en) 2012-11-27 2018-06-19 Contipro A.S. C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof
WO2015135511A1 (en) 2014-03-11 2015-09-17 Contipro Biotech S.R.O. Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof
US10023658B2 (en) 2014-03-11 2018-07-17 Contipro A.S. Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof
US10363595B2 (en) 2014-06-09 2019-07-30 Hyperion Materials & Technologies (Sweden) Ab Cemented carbide necking tool
US10617711B2 (en) 2014-06-30 2020-04-14 Contipro A.S. Antitumor composition based on hyaluronic acid and inorganic nanoparticles, method of preparation thereof and use thereof
US10689464B2 (en) 2015-03-09 2020-06-23 Contipro A.S. Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of preparation and use thereof
WO2016202314A1 (en) 2015-06-15 2016-12-22 Contipro A.S. Method of crosslinking of polysaccharides using photoremovable protecting groups
US10759878B2 (en) 2015-06-15 2020-09-01 Contipro A.S. Method of crosslinking of polysaccharides using photoremovable protecting groups
US10414832B2 (en) 2015-06-26 2019-09-17 Contipro A.S Derivatives of sulfated polysaccharides, method of preparation, modification and use thereof
US10618984B2 (en) 2016-06-27 2020-04-14 Contipro A.S. Unsaturated derivatives of polysaccharides, method of preparation thereof and use thereof

Also Published As

Publication number Publication date
JP2009545637A (ja) 2009-12-24
AU2007280846B2 (en) 2012-06-14
US20090312283A1 (en) 2009-12-17
US8202986B2 (en) 2012-06-19
CN101501075B (zh) 2013-07-10
EP2049572A1 (en) 2009-04-22
CA2657823A1 (en) 2008-02-07
AU2007280846A1 (en) 2008-02-07
CN101501075A (zh) 2009-08-05

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