[go: up one dir, main page]

WO1995003315A3 - Saccharides, their synthesis and use - Google Patents

Saccharides, their synthesis and use Download PDF

Info

Publication number
WO1995003315A3
WO1995003315A3 PCT/GB1994/001575 GB9401575W WO9503315A3 WO 1995003315 A3 WO1995003315 A3 WO 1995003315A3 GB 9401575 W GB9401575 W GB 9401575W WO 9503315 A3 WO9503315 A3 WO 9503315A3
Authority
WO
WIPO (PCT)
Prior art keywords
conjugate
sugar2
sugar1
polysaccharide
derived
Prior art date
Application number
PCT/GB1994/001575
Other languages
French (fr)
Other versions
WO1995003315A2 (en
Inventor
Colin Campion
Mezher Hussein Ali
Michael Glen Orchard
Stephen Martin Courtney
Rajesh Bhikhu Parekh
Original Assignee
Oxford Glycosystems Ltd
Colin Campion
Mezher Hussein Ali
Michael Glen Orchard
Stephen Martin Courtney
Rajesh Bhikhu Parekh
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 claimed from GB939315111A external-priority patent/GB9315111D0/en
Priority claimed from GB939315112A external-priority patent/GB9315112D0/en
Priority claimed from GB939315114A external-priority patent/GB9315114D0/en
Priority claimed from GB939315113A external-priority patent/GB9315113D0/en
Priority claimed from GB939318037A external-priority patent/GB9318037D0/en
Application filed by Oxford Glycosystems Ltd, Colin Campion, Mezher Hussein Ali, Michael Glen Orchard, Stephen Martin Courtney, Rajesh Bhikhu Parekh filed Critical Oxford Glycosystems Ltd
Priority to AU71934/94A priority Critical patent/AU7193494A/en
Publication of WO1995003315A2 publication Critical patent/WO1995003315A2/en
Publication of WO1995003315A3 publication Critical patent/WO1995003315A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • 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
    • A61K47/51—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 non-active ingredient being a modifying agent
    • A61K47/56—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • 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
    • A61K47/51—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 non-active ingredient being a modifying agent
    • A61K47/62—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 non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/66—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood sugars, e.g. galactose
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Hematology (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Microbiology (AREA)
  • Cell Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Veterinary Medicine (AREA)
  • Food Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Genetics & Genomics (AREA)
  • Diabetes (AREA)
  • Saccharide Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

A library comprises at least six different sugar-containing molecules selected from (i) carbohydrates each derived from at least two saccharide monomers, and (ii) glycoconjugates. Such a library may comprise disaccharides or linear or branched trisaccharides. It may be prepared from a compound having at least two OH groups which are modified by independently-removable blocking groups. A novel process comprises synthesising a polysaccharide of the formula sugarn, n representing the number of mono- and/or oligo-saccharide units from which the polysaccharide may be derived, comprises the steps of coupling sugar2 with a conjugate of the formula Q-sugar1, Q being a removable lipophilic or polymeric material, in a solvent for the conjugate; adding a non-solvent for the resultant conjugate Q-sugar1-sugar2; repeating the said steps n-2 times, as necessary, selecting the sugar to be coupled independently each time; and removing Q from the resultant coupled conjugate.
PCT/GB1994/001575 1993-07-21 1994-07-21 Saccharides, their synthesis and use WO1995003315A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU71934/94A AU7193494A (en) 1993-07-21 1994-07-21 Saccharides, their synthesis and use

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
GB939315111A GB9315111D0 (en) 1993-07-21 1993-07-21 Saccharides
GB939315112A GB9315112D0 (en) 1993-07-21 1993-07-21 Saccharides
GB939315114A GB9315114D0 (en) 1993-07-21 1993-07-21 Glycoconjugates
GB9315114.0 1993-07-21
GB939315113A GB9315113D0 (en) 1993-07-21 1993-07-21 Saccharides,glycoconjugates and their use
GB9315113.2 1993-07-21
GB9315112.4 1993-07-21
GB9315111.6 1993-07-21
GB939318037A GB9318037D0 (en) 1993-08-31 1993-08-31 Multi-functional compounds and their use
GB9318037.0 1993-08-31

Publications (2)

Publication Number Publication Date
WO1995003315A2 WO1995003315A2 (en) 1995-02-02
WO1995003315A3 true WO1995003315A3 (en) 1995-06-01

Family

ID=27517197

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1994/001575 WO1995003315A2 (en) 1993-07-21 1994-07-21 Saccharides, their synthesis and use

Country Status (2)

Country Link
AU (1) AU7193494A (en)
WO (1) WO1995003315A2 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5837689A (en) * 1993-06-16 1998-11-17 Glycomed Incorporated Sialyl lewis-x mimetics containing naphthyl backbones
US5789385A (en) * 1993-06-16 1998-08-04 Glycomed Incorporated Sialyl Lewisx mimetics containing phenyl backbones
US5593853A (en) * 1994-02-09 1997-01-14 Martek Corporation Generation and screening of synthetic drug libraries
AU717099B2 (en) * 1995-03-08 2000-03-16 Scripps Research Institute, The Carbopeptoids and carbonucleotoids
WO1997035202A1 (en) * 1996-03-21 1997-09-25 Princeton University Carbohydrate-based ligand library, assay and method
US6828435B2 (en) 1996-04-17 2004-12-07 Hk Pharmaceuticals, Inc. Combinatorial protecting group strategy for multifunctional molecules
DE19621177A1 (en) * 1996-05-24 1997-11-27 Basf Ag Carbohydrate derivatives and their synthesis on solid phase
DE19642751A1 (en) * 1996-10-16 1998-04-23 Deutsches Krebsforsch Saccharide library
CA2299295C (en) * 1997-08-08 2010-11-30 Aventis Pharma Deutschland Gmbh Substituted tetrahydropyrane derivatives and method for producing same
AU2606700A (en) * 1999-01-12 2000-08-01 Princeton University Saccharides linked to compounds that bind cell-surface peptides or proteins
DE60031957T2 (en) * 1999-02-17 2007-09-13 Glycominds Ltd. COMBINATIVE, COMPLEX CARBOHYDRATE LIBRARIES AND METHOD FOR THE PREPARATION AND USE THEREOF
AUPS213802A0 (en) * 2002-05-03 2002-06-06 Alchemia Pty Ltd Disaccharides for drug discovery

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000091A1 (en) * 1990-07-02 1992-01-09 Bioligand, Inc. Random bio-oligomer library, a method of synthesis thereof, and a method of use thereof
WO1992009300A1 (en) * 1990-11-21 1992-06-11 Iterex Pharmaceuticals Ltd. Partnership Synthesis of equimolar multiple oligomer mixtures, especially of oligopeptide mixtures
WO1993006121A1 (en) * 1991-09-18 1993-04-01 Affymax Technologies N.V. Method of synthesizing diverse collections of oligomers

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992000091A1 (en) * 1990-07-02 1992-01-09 Bioligand, Inc. Random bio-oligomer library, a method of synthesis thereof, and a method of use thereof
WO1992009300A1 (en) * 1990-11-21 1992-06-11 Iterex Pharmaceuticals Ltd. Partnership Synthesis of equimolar multiple oligomer mixtures, especially of oligopeptide mixtures
WO1993006121A1 (en) * 1991-09-18 1993-04-01 Affymax Technologies N.V. Method of synthesizing diverse collections of oligomers

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DOUGLAS S.P. ET AL: "Polymer-supported solution synthesis of oligosaccharides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 113, no. 13, June 1991 (1991-06-01), GASTON, PA US, pages 5095 - 5097 *
KANDIL A.A. ET AL: "Synthesis of fragments of the capsular polysaccharide of Haemophilus Influenza type b on a soluble polymeric support", SYNLETT, no. 7, July 1992 (1992-07-01), STUTTGART DE, pages 555 - 557 *
MIZUOCHI T. ET AL: "A Library of Oligosaccharide Probes (Neoglycolipids) from N-Glycosylated Proteins Reveals That Conglutinin Binds to Certain Complex-type as Well as High Mannose-type Oligosaccharide chains", JOURNAL OF BIOLOGICAL CHEMISTRY., vol. 264, no. 23, 15 August 1989 (1989-08-15), BALTIMORE US, pages 13834 - 13839 *

Also Published As

Publication number Publication date
WO1995003315A2 (en) 1995-02-02
AU7193494A (en) 1995-02-20

Similar Documents

Publication Publication Date Title
WO1995003315A3 (en) Saccharides, their synthesis and use
Kochetkov Tetrahedron report number 218: Synthesis of polysaccharides with a regular structure
Cerantola et al. NMR characterisation of inulin-type fructooligosaccharides as the major water-soluble carbohydrates from Matricaria maritima (L.)
Zanini et al. Synthesis of novel dendritic glycosides
IL97853A (en) Saccharide compositions and methods and apparatus for their synthesis
IE901187L (en) Sugar composition comprising soluble fibre
AU8044598A (en) Process for preparation of a dendritic polyol
WO1996020236A1 (en) Polyglycomers
CA2028541A1 (en) Photosensitive mixture
Pornsuriyasak et al. Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis
Van Boeckel et al. Substituent effects in carbohydrate chemistry, Part II+. Coupling reactions involving gluco‐and galacto‐pyranosyl bromides promoted by insoluble silver salts
Fernandez-Santana et al. Glycosides of monoallyl diethylene glycol. A new type of spacer group for synthetic oligosaccharides
KR960704904A (en) Water-soluble retinoids
Hostettmann et al. A New Xanthone Diglucoside from Swertia perennisL.
Falk et al. Two-dimensional1H and13C NMR spectroscopy and the structural aspects of amylose and amylopectin
Çaliş et al. Anatolioside E: a new acyclic monoterpene glycoside from Viburnum orientale
WO1997021416A3 (en) Glycoconjugates of opiated substances
Parrot-Lopez et al. New β-cyclodextrin derivatives possessing biologically active saccharide antennae
de Paz et al. Exploration of the use of an acylsulfonamide safety-catch linker for the polymer-supported synthesis of hyaluronic acid oligosaccharides
Waki et al. A new O-acetylated trisialoganglioside, 9-O-acetyl GT2, in cod brain
ZA912840B (en) Saccharide compositions,methods and apparatus for their synthesis
Cuervo-Rodriguez et al. Synthesis and characterization of novel glycopolymers based on ethyl α-hydroxymethylacrylate
Hatanaka et al. Synthesis and sulfation of branched dextrans
Nunn et al. Sulphated polysaccharides of the Solieriaceae family: Part II. The acidic components of the polysaccharide from the red alga Anatheca dentata
Backinowsky et al. Synthesis of oligosaccharide fragments of Shigella flexneri O-specific polysaccharides. The synthesis of two branched trisaccharides.

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AM AU BB BG BR BY CA CN CZ FI GB GE HU JP KE KG KP KR KZ LK LT LV MD MG MN MW NO NZ PL RO RU SD SI SK TJ TT UA US UZ VN

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): KE MW SD AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
AK Designated states

Kind code of ref document: A3

Designated state(s): AM AU BB BG BR BY CA CN CZ FI GB GE HU JP KE KG KP KR KZ LK LT LV MD MG MN MW NO NZ PL RO RU SD SI SK TJ TT UA US UZ VN

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): KE MW SD AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA