KR900018129A - 콘드로이틴 황산염, 데르마탄황산염 및 히알루론산의 술포아미노 유도체와 그 약제학적 성질 - Google Patents

콘드로이틴 황산염, 데르마탄황산염 및 히알루론산의 술포아미노 유도체와 그 약제학적 성질 Download PDF

Info

Publication number
KR900018129A
KR900018129A KR1019890005904A KR890005904A KR900018129A KR 900018129 A KR900018129 A KR 900018129A KR 1019890005904 A KR1019890005904 A KR 1019890005904A KR 890005904 A KR890005904 A KR 890005904A KR 900018129 A KR900018129 A KR 900018129A
Authority
KR
South Korea
Prior art keywords
sulfate
derivatives
deacetylation
process according
pharmaceutical composition
Prior art date
Application number
KR1019890005904A
Other languages
English (en)
Inventor
카수 베니로
토리 지안지아코모
마지 안나마리아
만토반니 마리자
페스카도르 로돌포
포르타 로베르토
프리노 지우세페
Original Assignee
로베르토 베르타니
크리노스 인더스트리아 파르마코비올로지카 쏘시에떼 퍼 아찌오니
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 로베르토 베르타니, 크리노스 인더스트리아 파르마코비올로지카 쏘시에떼 퍼 아찌오니 filed Critical 로베르토 베르타니
Publication of KR900018129A publication Critical patent/KR900018129A/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • 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
    • C08B37/0069—Chondroitin-4-sulfate, i.e. chondroitin sulfate A; Dermatan sulfate, i.e. chondroitin sulfate B or beta-heparin; Chondroitin-6-sulfate, i.e. chondroitin sulfate C; Derivatives thereof
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Dermatology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

내용 없음

Description

콘드로이틴 황산염, 데르마탄황산염 및 히알루론산의 술포아미노 유도체와 그 약제학적 성질
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도 출발물질인 큰드로이틴4-황산염과 콘드로이틴 N, 4-중황산염(GAG 973)의 13C NMR 스펙트럼을 나타낸다. 제2도는 콘드로이틴 6-황산염(GAG 921)출발물질 및 콘드로이틴 N, 6-중황산염(GAG 974)의 13CNMR 스펙트럼을 나타낸다. 제3도는 데르마탄 황산염(GAG 968) 및 데르마탄 N, 4 중황산염(GAG 944Ⅳ)의 13CNMR 스펙트럼을 나타내다.

Claims (12)

  1. 의 구조식으로된 이량적 단위체의 콘드로이틴 황산염 A 및 C 그 혼합물 데르마탄 황산염 또한 콘드로이틴 황산염 B에서 선별된 클리코사미노 글리칸의 합성 술포아미노 유도체.
    (R은 OH,, R1은 H,, Y는 H,, 또한 X는 H,).
  2. 의 구조식으로된 이량적 단위체의 히알루론산의 합성 술포 아미노유도체.
  3. 제1항 및 2항에 있어서, 건조 조건하에서 다음처럼 측정되고 상응하는 나트륨염에 관련하는 화학변수를 특징으로 하는 합성 유도체:
    슬폰황산 8.0-12%, 황산염/카르복실그룹 1.5-2.3%, 잔여 N-아세틸그룹 3, 분자량 2.3-30x103.
  4. 제3항에 있어서, 다음의 범위속에 포함되는 상기의 변수를 특징으로 하는 합성 유도체:
    슬폰황산 9.5-11.4%, 황산염/카르복실그룹 1.8-2.1, 잔여N-아세틸그룹 1%, 분자량 3-15x103.
  5. 출발물질인 글리코사미노글리칸을 여분의 히드라진 황산염 및 무수 히드라진과 함께 6시간 동안 105℃로 가열하여 이루어지는 1차 탈아세틸화 단계와 여분의 황산화 작용제와 함께 pH9로한 수성매질속에서 이루어진 선별적인 N-황산화 반응인 후속단계를 특징으로 하는 제1항 및 2항에 따르는 유도체의 제조방법.
  6. 제5항에 있어서, 상기의 황산화 작용제가 트리에틸아민-무수황산 및 클로로술폰산 중에서 선별되는 것을 특징으로 하는 제조공정.
  7. 제5항에 있어서, 후속의 N-황산화 단계에 요구되는 수준의 아세틸 그룹 함량을 얻을때까지 상기의 N-탈아세틸화 반응이 여러단계에 걸쳐 실행되는 것을 특징으로 하는 제조공정.
  8. 제5항에 있어서, 상기의 N-탈아세틸화 단계전에 공지방법의 예비 해축단계가 실행되는 것을 특징으로 하는 제조공정.
  9. 제8항에 있어서, 상기의 해축단계가 N-황산화 단계전에 실행되는 것을 특징으로 하는 제조공정.
  10. 일반적인 부형제와 함께 활성성분인 제1항 및 2항에 따르및는 글리코사미노글리칸 유도체를 함유하는 것을 특징으로하는 약제학적 조성물.
  11. 제10항에 있어서, 명화 활성도(clearing activity)가 있는 약제학적 조성물.
  12. 제10항에 있어서, 상기의 활성성분이 1-500㎎의 단위량 속에 함유되는 특징으로 하는 약제학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890005904A 1988-05-02 1989-05-02 콘드로이틴 황산염, 데르마탄황산염 및 히알루론산의 술포아미노 유도체와 그 약제학적 성질 KR900018129A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT20412A/88 1988-05-02
IT20412/88A IT1217458B (it) 1988-05-02 1988-05-02 Sulfoamino derivati di condroitin solfati,del dermatan solfato e dell' acido ialuronico e loro proprieta' farmacologiche

Publications (1)

Publication Number Publication Date
KR900018129A true KR900018129A (ko) 1990-12-20

Family

ID=11166540

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019890005904A KR900018129A (ko) 1988-05-02 1989-05-02 콘드로이틴 황산염, 데르마탄황산염 및 히알루론산의 술포아미노 유도체와 그 약제학적 성질

Country Status (11)

Country Link
US (1) US5008253A (ko)
EP (1) EP0340628B1 (ko)
JP (1) JPH01318002A (ko)
KR (1) KR900018129A (ko)
AT (1) ATE109163T1 (ko)
AU (1) AU618346B2 (ko)
CA (1) CA1307525C (ko)
DE (1) DE68917009T2 (ko)
ES (1) ES2057006T3 (ko)
IT (1) IT1217458B (ko)
PT (1) PT90414B (ko)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8826448D0 (en) * 1988-11-11 1988-12-14 Thrombosis Res Inst Improvements in/relating to organic compounds
DK0421508T3 (da) * 1989-10-04 1994-04-11 Akzo Nobel Nv Sulfateret glycosaminoglycuronan med antithrombotisk aktivitet
FR2655267B1 (fr) * 1989-12-04 1992-04-03 Roussel Uclaf Nouveau derive sulfate du galactanne extrait de klebsiella, procede de preparation, application a titre de medicaments et compositions pharmaceutiques le renfermant.
WO1991015217A1 (en) * 1990-04-06 1991-10-17 Washington University Anticoagulant oligosaccharides
FR2669932B1 (fr) * 1990-12-03 1994-07-01 Sanofi Sa Nouvel heparosane-n,o-sulfate, son procede de preparation et les compositions pharmaceutiques qui le contiennent.
US5629287A (en) * 1991-01-18 1997-05-13 University College London Depot formulations
US5610148A (en) * 1991-01-18 1997-03-11 University College London Macroscopically oriented cell adhesion protein for wound treatment
GB2286193A (en) * 1991-03-28 1995-08-09 Italfarmaco Spa Anticoagulants and processes for preparing such
US5605938A (en) * 1991-05-31 1997-02-25 Gliatech, Inc. Methods and compositions for inhibition of cell invasion and fibrosis using dextran sulfate
US5705178A (en) * 1991-05-31 1998-01-06 Gliatech, Inc. Methods and compositions based on inhibition of cell invasion and fibrosis by anionic polymers
US5234914A (en) * 1991-06-11 1993-08-10 Patent Biopharmaceutics, Inc. Methods of treating hemorrhoids and anorecial disease
WO1994017538A2 (en) * 1993-01-21 1994-08-04 Mayo Foundation For Medical Education And Research Microparticle switching devices
US5654006A (en) * 1993-02-12 1997-08-05 Mayo Foundation For Medical Education And Research Condensed-phase microparticle composition and method
US5753261A (en) * 1993-02-12 1998-05-19 Access Pharmaceuticals, Inc. Lipid-coated condensed-phase microparticle composition
US5820879A (en) * 1993-02-12 1998-10-13 Access Pharmaceuticals, Inc. Method of delivering a lipid-coated condensed-phase microparticle composition
ITPD940054A1 (it) * 1994-03-23 1995-09-23 Fidia Advanced Biopolymers Srl Polisaccaridi solfatati
US5690961A (en) * 1994-12-22 1997-11-25 Hercules Incorporated Acidic polysaccharides crosslinked with polycarboxylic acids and their uses
IT1290814B1 (it) * 1997-03-24 1998-12-11 Istituto Scient Di Chimica E B Glicosaminoglicani aventi elevata attivita' antitrombotica
ATE229038T1 (de) 1997-04-04 2002-12-15 Fidia Advanced Biopolymers Srl N-sulfatierte hyaluronsäureverbindungen, ihre derivate und verfahren zu ihrer herstellung
DE19813234A1 (de) * 1998-03-26 1999-09-30 Knoell Hans Forschung Ev Verfahren zur Herstellung hochsulfatierter Hyaluronsäuren
US20030104601A1 (en) * 1999-04-01 2003-06-05 Deangelis Paul L. Chondroitin synthase gene and methods of making and using same
US7223571B2 (en) * 1998-04-02 2007-05-29 The Board Of Regents Of The Universtiy Of Oklahoma Targeted glycosaminoglycan polymers by polymer grafting and methods of making and using same
US20080108110A1 (en) * 1998-04-02 2008-05-08 Deangelis Paul L Targeted glycosaminoglycan polymers by polymer grafting and methods of making and using same
US20060188966A1 (en) * 1998-04-02 2006-08-24 Deangelis Paul L Natural, chimeric and hybrid glycosaminoglycan polymers and methods of making and using same
KR100530196B1 (ko) 1998-04-30 2005-11-22 마루하 가부시키가이샤 구조내 글루쿠론산 유도체 및 글루코사민 유도체를 갖는화합물, 그의 제법 및 그의 용도
US20020086852A1 (en) * 1998-05-14 2002-07-04 Cantor Jerome O. Method for treating respiratory disorders associated with pulmonary elastic fiber injury
ITPD980169A1 (it) 1998-07-06 2000-01-06 Fidia Advanced Biopolymers Srl Ammidi dell'acido ialuronico e dei suoi derivati e processo per la loro preparazione.
US7642071B2 (en) 1999-04-01 2010-01-05 The Board Of Regents Of The University Of Oklahoma Methods of expressing gram-negative glycosaminoglycan synthase genes in gram-positive hosts
US20040161476A1 (en) * 2003-02-19 2004-08-19 Hahn Sungtack Samuel Cystitis treatment with high dose chondroitin sulfate
ITPD20050056A1 (it) 2005-03-02 2006-09-03 Fidia Farmaceutici Derivati ammidici del'acido ialuronico in osteoartrosi
BRPI0909849A2 (pt) 2008-04-04 2015-10-06 Univ Utah Res Found éteres semi-sintéticos de glicosaminoglicosanos e métodos para fazê-los e usá-los
IT1397247B1 (it) * 2009-05-14 2013-01-04 Fidia Farmaceutici Nuovi agenti regolatori dell'attivita' citochinica
US8546353B2 (en) * 2010-05-06 2013-10-01 Glykos Finland Oy Compounds and combinations
US9522162B2 (en) 2011-03-23 2016-12-20 University Of Utah Research Foundation Methods for treating or preventing urological inflammation
EP2928500B1 (en) 2012-12-04 2019-03-06 Phosphorex Inc. Microparticles and nanoparticles having negative surface charges
JP6063103B1 (ja) * 2015-03-31 2017-01-18 生化学工業株式会社 グリコサミノグリカンの硫酸化方法
WO2018053111A1 (en) 2016-09-15 2018-03-22 University Of Utah Research Foundation In situ gelling compositions for the treatment or prevention of inflammation and tissue damage
CN111228653A (zh) 2018-11-13 2020-06-05 格莱科米拉治疗公司 用电离辐射加强癌症治疗的方法
CN111662394B (zh) * 2019-03-05 2022-11-04 中国医学科学院药物研究所 硫酸软骨素多糖半合成制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB838709A (en) * 1955-09-22 1960-06-22 Upjohn Co Improvements in or relating to aminoalcohol-n-sulphonic acid compounds
US3405120A (en) * 1966-01-27 1968-10-08 Green Cross Corp Low molecular chondroitin sulfate and method for manufacturing the same
FR2504535B1 (fr) * 1981-04-28 1987-08-14 Choay Sa Disaccharides derives d'un acide uronique et d'une glucosamine et compositions pharmaceutiques les contenant pour le controle de la coagulation sanguine
US4818816A (en) * 1981-04-28 1989-04-04 Choay, S.A. Process for the organic synthesis of oligosaccharides and derivatives thereof
EP0838709A3 (de) * 1996-09-30 1999-07-28 Siemens Aktiengesellschaft Anordnung zur Erzeugung einer Umsetzung zwischen Lichtstrahlen kleineren Strahlquerschnitts und einem Lichtstrahl grösseren Strahlquerschnitts

Also Published As

Publication number Publication date
CA1307525C (en) 1992-09-15
US5008253A (en) 1991-04-16
EP0340628A3 (en) 1990-01-24
JPH01318002A (ja) 1989-12-22
EP0340628B1 (en) 1994-07-27
IT1217458B (it) 1990-03-22
ATE109163T1 (de) 1994-08-15
PT90414A (pt) 1989-11-30
EP0340628A2 (en) 1989-11-08
IT8820412A0 (it) 1988-05-02
AU618346B2 (en) 1991-12-19
AU3392289A (en) 1989-11-02
DE68917009D1 (de) 1994-09-01
PT90414B (pt) 1994-08-31
ES2057006T3 (es) 1994-10-16
DE68917009T2 (de) 1994-11-10

Similar Documents

Publication Publication Date Title
KR900018129A (ko) 콘드로이틴 황산염, 데르마탄황산염 및 히알루론산의 술포아미노 유도체와 그 약제학적 성질
KR920000792A (ko) 저 분자량 다당류 혼합물, 그의 제조 방법 및 그로 구성된 치료 조성물
JP2702376B2 (ja) α−Ｌ−イズロン酸−２−Ｏ−硫酸が修飾されたヘパリンまたはヘパラン構造を有する半合成グリコサミノグリカン
JPH0629282B2 (ja) 解重合及び超硫酸化ヘパリン、その製造方法並びに製薬組成物
EP0970130B1 (en) Glycosaminoglycans having high antithrombotic activity
EP0827514A1 (en) Heavy metal salts of succinic acid hemiesters with hyaluronic acid, or hyaluronic acid esters, a process for their preparation, and relative pharmaceutical compositions
Chaubet et al. Synthesis and structure—anticoagulant property relationships of functionalized dextrans: CMDBS
EA033936B1 (ru) Усовершенствованный способ получения сульфатированной ha высокой степени чистоты
PT91249B (pt) Processo para a preparacao de glicosaminoglicanos selectivamente o-acilados
IT9021909A1 (it) Procedimento per la preparazione di epossi-eparidi prodotti ottenuti e composizioni farmaceutiche che li contengono
CA2439337A1 (en) Highly sulfated derivatives of k5 polysaccharide and their preparation
RU2000100374A (ru) Смеси олигосахаридов, обладающие антитромботической активностью
CZ292622B6 (cs) Směs oligosacharidů s antitrombotickou účinností, způsob její přípravy a použití a farmaceutický prostředek s jejím obsahem
WO2003106506A1 (en) Low molecular weight oversulfated polysaccharide
DE69027256D1 (de) Sulfatiertes polysaccharid, dessen pharmazeutisch verträgliche salze, dessen herstellung und medikament, das dieses als wirksstoff enthält
DE69403537T2 (de) Verfahren zur Synthese von halbsynthetischen Glykosaminoglykanen mit Heparin- oder Heparanstruktur, die in 2-Position modifiziertes Alpha-L-Iduronsäure-2-O-Sulfat enthalten
HU226370B1 (en) Carbohydrate derivatives with antithrombotic activity and pharmaceutical compositions contg. them
EP0032825A2 (en) Stabilized solutions of dioctyl calcium sulfosuccinate in corn oil
DE4242813A1 (ko)
ZA200410358B (en) Low molecular weight oversulfated polysaccharide.
Sutherland Structural studies in certain animal polysaccharides
RU2005100965A (ru) Способ получения производных n-ацил-(эпи)к5-амин-о-сульфатов и получаемые при этом продукты

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E601 Decision to refuse application