CA2666103C - Glycomimetic replacements for hexoses and n-acetyl hexosamines - Google Patents

Glycomimetic replacements for hexoses and n-acetyl hexosamines Download PDF

Info

Publication number
CA2666103C
CA2666103C CA2666103A CA2666103A CA2666103C CA 2666103 C CA2666103 C CA 2666103C CA 2666103 A CA2666103 A CA 2666103A CA 2666103 A CA2666103 A CA 2666103A CA 2666103 C CA2666103 C CA 2666103C
Authority
CA
Canada
Prior art keywords
fuc
alkanyl
mmol
gal
compound
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.)
Active
Application number
CA2666103A
Other languages
English (en)
French (fr)
Other versions
CA2666103A1 (en
Inventor
Beat Ernst
Daniel Schwizer
Arun K. Sarkar
John L. Magnani
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.)
Crescent Biopharma Inc
Original Assignee
Glycomimetics Inc
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 Glycomimetics Inc filed Critical Glycomimetics Inc
Publication of CA2666103A1 publication Critical patent/CA2666103A1/en
Application granted granted Critical
Publication of CA2666103C publication Critical patent/CA2666103C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/207Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
CA2666103A 2006-10-12 2007-10-09 Glycomimetic replacements for hexoses and n-acetyl hexosamines Active CA2666103C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US85146706P 2006-10-12 2006-10-12
US60/851,467 2006-10-12
PCT/US2007/021541 WO2008060378A2 (en) 2006-10-12 2007-10-09 Glycomimetic replacements for hexoses and n-acetyl hexosamines

Publications (2)

Publication Number Publication Date
CA2666103A1 CA2666103A1 (en) 2008-05-22
CA2666103C true CA2666103C (en) 2014-02-18

Family

ID=39402172

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2666103A Active CA2666103C (en) 2006-10-12 2007-10-09 Glycomimetic replacements for hexoses and n-acetyl hexosamines

Country Status (5)

Country Link
US (2) US7964569B2 (enExample)
EP (1) EP2074132B1 (enExample)
JP (2) JP5298020B2 (enExample)
CA (1) CA2666103C (enExample)
WO (1) WO2008060378A2 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9486497B2 (en) 2007-12-10 2016-11-08 The University Of Queensland Treatment of immunocompromised conditions
EP2424544A1 (en) 2009-05-01 2012-03-07 GlycoMimetics, Inc. Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
JPWO2011040574A1 (ja) * 2009-09-30 2013-02-28 国立大学法人京都大学 アゼチジニルメトキシピリジン誘導体の製造方法及びその使用
WO2012037034A1 (en) 2010-09-14 2012-03-22 Glycomimetics, Inc. E-selectin antagonists
WO2012061662A1 (en) 2010-11-03 2012-05-10 Glycomimetics, Inc. Glycomimetic-peptidomimetic inhibitors of e-selectins and cxcr4 chemokine receptors
EP3296310A1 (en) 2011-12-22 2018-03-21 GlycoMimetics, Inc. E-selectin antagonist compounds, compositions, and methods of use
US9867841B2 (en) 2012-12-07 2018-01-16 Glycomimetics, Inc. Compounds, compositions and methods using E-selectin antagonists for mobilization of hematopoietic cells
WO2014149837A1 (en) * 2013-03-15 2014-09-25 Glycomimetics, Inc. Compounds and methods to enhance the oral availability of glycomimetics
WO2015109049A1 (en) * 2014-01-17 2015-07-23 Glycomimetics, Inc. E-selectin antagonists modified by macrocycle formation to the galactose
ES2754549T3 (es) 2014-12-03 2020-04-20 Glycomimetics Inc Inhibidores heterobifuncionales de E-selectinas y receptores de quimioquinas CXCR4
JP2019502727A (ja) * 2016-01-22 2019-01-31 グリコミメティクス, インコーポレイテッド Pa−ilおよび/またはpa−iilレクチンの糖模倣体阻害剤
US11291678B2 (en) 2016-03-02 2022-04-05 Glycomimetics, Inc Methods for the treatment and/or prevention of cardiovascular disease by inhibition of E-selectin
WO2018031445A1 (en) 2016-08-08 2018-02-15 Glycomimetics, Inc. Combination of t-cell checkpoint inhibitors with inhibitors of e-selectin or cxcr4, or with heterobifunctional inhibitors of both e-selectin and cxcr4
CA3037850A1 (en) * 2016-10-07 2018-04-12 Glycomimetics, Inc. Highly potent multimeric e-selectin antagonists
CA3054605A1 (en) * 2017-03-15 2018-09-20 Glycomimetics, Inc. Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists
EP3717013A1 (en) 2017-11-30 2020-10-07 GlycoMimetics, Inc. Methods of mobilizing marrow infiltrating lymphocytes and uses thereof
CA3085356A1 (en) 2017-12-29 2019-07-04 Glycomimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
KR20200128025A (ko) 2018-03-05 2020-11-11 글리코미메틱스, 인크. 급성 골수성 백혈병 및 관련 병태의 치료 방법
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
KR20220012246A (ko) 2019-04-24 2022-02-03 글리코미메틱스, 인크. E-셀렉틴, 갈렉틴-3, 및/또는 cxcr4 케모카인 수용체의 갈락토오스 연결된 다량체성 글리코모방체 억제제

Family Cites Families (113)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4471057A (en) 1981-06-30 1984-09-11 The Wistar Institute Detection of colorectal carcinoma
DK17885D0 (da) 1985-01-14 1985-01-14 Karlsson Karl Anders Antiviralt middel
US4876199A (en) 1985-04-04 1989-10-24 Fred Hutchinson Cancer Research Center Hybridomas producing monoclonal antibodies to mono-, di-, and trifucosylated type 2 chain
US4851511A (en) 1986-01-30 1989-07-25 Fred Hutchinson Cancer Research Center Monoclonal antibody that specifically binds to disialosyl Lea
US4925796A (en) 1986-03-07 1990-05-15 Massachusetts Institute Of Technology Method for enhancing glycoprotein stability
EP0249008B1 (de) 1986-05-09 1993-09-15 Pulverer, Gerhard, Prof. Dr.Dr.h.c. Verwendung von spezifischen Monosacchariden zur Herstellung eines Arzneimittels zur Verhinderung von Metastasen maligner Tumore
US5538724A (en) 1987-08-11 1996-07-23 The Board Of Trustees For The Leland Stanford Junior Univ. Method of control leukocyte extravasation
US5464778A (en) 1989-03-08 1995-11-07 Board Of Regents Of The University Of Oklahoma Glycoprotein ligand for P-selectin and methods of use thereof
US6033665A (en) 1989-09-27 2000-03-07 Elan Pharmaceuticals, Inc. Compositions and methods for modulating leukocyte adhesion to brain endothelial cells
US6280932B1 (en) 1990-06-11 2001-08-28 Gilead Sciences, Inc. High affinity nucleic acid ligands to lectins
US6001988A (en) 1990-06-11 1999-12-14 Nexstar Pharmaceuticals, Inc. High affinity nucleic acid ligands to lectins
US5753631A (en) 1990-06-15 1998-05-19 Cytel Corporation Intercellular adhesion mediators
US5576305A (en) 1990-06-15 1996-11-19 Cytel Corporation Intercellular adhesion mediators
US6391857B1 (en) 1990-06-18 2002-05-21 Stanford University Methods and compositions for endothelial binding
US6387884B1 (en) 1990-06-18 2002-05-14 Stanford University Leukocyte homing modulation
US5648344A (en) 1990-07-30 1997-07-15 Glycomed Incorporated Methods of treating inflammation using selection binding compounds
US5211937A (en) 1990-07-30 1993-05-18 Glycomed Incorporated Method of determining a site of inflammation utilizing elam-1 ligands
US5143712A (en) 1990-07-30 1992-09-01 Glycomed Incorporated Method of determining a site of inflammation utilizing elam-1 ligands
US5789573A (en) 1990-08-14 1998-08-04 Isis Pharmaceuticals, Inc. Antisense inhibition of ICAM-1, E-selectin, and CMV IE1/IE2
MC2324A1 (fr) 1990-11-23 1994-01-18 Gen Hospital Corp Inhibition des interactions entre les proteines d'adherence cellulaire et les hydrates de carbone
US5151360A (en) 1990-12-31 1992-09-29 Biomembrane Institute Effect of n,n,n-trimethylsphingosine on protein kinase-c activity, melanoma cell growth in vitro, metastatic potential in vivo and human platelet aggregation
US6124267A (en) 1991-02-05 2000-09-26 Southpac Trust Internationals, Inc. O-glycan inhibitors of selectin mediated inflammation derived from PSGL-1
US6309639B1 (en) 1991-02-05 2001-10-30 The Board Of Regents Of The University Of Oklahoma Method for inhibiting an inflammatory response using antibodies to P-selectin glycoprotein ligand
US6121233A (en) 1991-04-19 2000-09-19 John L. Magnani Methods for the inhibition of cancer metastasis mediated by endothelial adhesion molecules
ES2201049T3 (es) 1991-05-06 2004-03-16 Genentech, Inc. Un ligando de selectina.
US5318890A (en) 1991-05-06 1994-06-07 The Regents Of The University Of California Assays for inhibitors of leukocyte adhesion
US5580858A (en) 1991-06-10 1996-12-03 Alberta Research Council Immunosuppressive and tolerogenic modified Lewisx compounds
US5646123A (en) 1991-06-10 1997-07-08 Alberta Research Council Time dependent administration of oligosaccharide glycosides related to blood group determinants having a type I or type II core structure in reducing inflammation in a sensitized mammal arising form exposure to an antigen
US5352670A (en) 1991-06-10 1994-10-04 Alberta Research Council Methods for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides
EP0608260A1 (en) 1991-09-10 1994-08-03 Centocor, Inc. Peptide inhibitors of inflammation mediated by selectins
US5268364A (en) 1991-12-12 1993-12-07 The Biomembrane Institute Method for inhibiting selectin-dependent adhesion of leukocytes and platelets by O-glycosylation modification
JPH07501828A (ja) 1991-12-18 1995-02-23 セントコー,インコーポレイテッド セレクチン類で仲介される炎症のペプチド阻害剤
US5591835A (en) 1992-06-29 1997-01-07 Glycomed Incorporated Substituted lactose derivatives
CA2100412A1 (en) 1992-07-15 1994-01-16 Yutaka Yamada Glycolipid derivatives
WO1994005310A1 (en) 1992-09-08 1994-03-17 Centocor, Inc. Peptide inhibitors of cellular adhesion
US5519008A (en) 1992-09-10 1996-05-21 Glycomed Incorporated Derivatives of triterpenoid acids as inhibitors of cell-adhesion molecules ELAM-1 (E-selectin) and LECAM-1 (L-selectin)
US5695752A (en) 1992-09-11 1997-12-09 The Regents Of The University Of California Treating inflammation via the administration of specific sulfatase enzymes and/or sulfation inhibitor
WO1994006442A1 (en) 1992-09-11 1994-03-31 The Regents Of The University Of California Sulfated ligands for l-selectins and use of chlorates and or sulfatases for the treatment of inflammation
US5843707A (en) 1992-10-23 1998-12-01 Genetics Institute, Inc. Nucleic acid encoding a novel P-selectin ligand protein
US6277975B1 (en) 1992-10-23 2001-08-21 Genetics Institute, Inc. Fusions of P-selectin ligand protein and polynucleotides encoding same
EP0601417A3 (de) 1992-12-11 1998-07-01 Hoechst Aktiengesellschaft Physiologisch verträglicher und physiologisch abbaubarer, Kohlenhydratrezeptorblocker auf Polymerbasis, ein Verfahren zu seiner Herstellung und seine Verwendung
WO1994014836A1 (en) 1992-12-18 1994-07-07 Centocor, Inc. Peptide inhibitors of selectin binding
US6558661B1 (en) 1992-12-29 2003-05-06 Genentech, Inc. Treatment of inflammatory bowel disease with IFN-γ inhibitors
US5412123A (en) 1993-02-08 1995-05-02 Glycomed Incorporated Anthraquinone and anthracene derivatives as inhibitors of the cell-adhesion molecules of the immune system
JP2716657B2 (ja) * 1993-02-26 1998-02-18 株式会社ディ・ディ・エス研究所 接着分子elam‐1に特異的結合能を有する化合物
WO1994020514A1 (fr) 1993-03-04 1994-09-15 Mect Corporation Compose associe au systeme de lewis, procede d'obtention de ce compose et anti-inflammatoire
US5527890A (en) 1993-04-16 1996-06-18 Glycomed Incorporated Derivatives of triterpenoid acids and uses thereof
CA2162478A1 (en) 1993-05-14 1994-11-24 Shawn A. Defrees Sialyl lex analogues as inhibitors of cellular adhesion
US5811404A (en) 1993-05-14 1998-09-22 Cytel Corporation Sialyl Lex analogues as inhibitors of cellular adhesion
US5854218A (en) 1993-05-14 1998-12-29 Cytel Corporation Sialyl Lex analogues as inhibitors of cellular adhesion
US5527785A (en) 1993-05-14 1996-06-18 The Regents Of The University Of California Selectin receptor modulating compositions
ES2174876T3 (es) 1993-05-17 2002-11-16 Avant Immunotherapeutics Inc Composiciones que comprenden proteinas relacionadas con el complementoy carbohidratos y metodos para producir y usar dichas composiciones.
US5976540A (en) 1993-05-17 1999-11-02 T Cell Sciences, Inc. Compositions comprising complement related proteins and carbohydrates, and methods for producing and using said compositions
US5646248A (en) 1993-06-08 1997-07-08 La Jolla Cancer Research Foundation E-selection binding soluble lamp-1 polypeptide
US5837689A (en) 1993-06-16 1998-11-17 Glycomed Incorporated Sialyl lewis-x mimetics containing naphthyl backbones
US5658880A (en) 1993-06-16 1997-08-19 Glycomed Incorporated Sialic acid/fucose based medicaments
US5750508A (en) 1993-06-16 1998-05-12 Glycomed Incorporated Sialic acid/fucose based medicaments
US5789385A (en) 1993-06-16 1998-08-04 Glycomed Incorporated Sialyl Lewisx mimetics containing phenyl backbones
US5679321A (en) 1993-06-17 1997-10-21 Glycomed Incorporated Sialic acid/fucose based medicaments
US5559103A (en) 1993-07-21 1996-09-24 Cytel Corporation Bivalent sialyl X saccharides
US5508387A (en) 1993-08-04 1996-04-16 Glycomed Incorporated Selectin binding glycopeptides
US5827837A (en) 1993-08-20 1998-10-27 The Regents Of The University Of California Polyanion anti-inflammatory agents
US5464815A (en) 1993-09-08 1995-11-07 Genentech, Inc. Inhibition of heparin-binding
CA2173990A1 (en) 1993-10-12 1995-04-20 Narasinga Rao A library of glyco-peptides useful for identification of cell adhesion inhibitors
US5783693A (en) 1993-11-19 1998-07-21 The Regents Of The University Of California Methods for synthesizing sulfated disaccharide inhibitors of selectins
WO1995014787A1 (en) 1993-11-22 1995-06-01 Centocor, Inc. Peptide inhibitors of selecting binding
US5663151A (en) 1994-03-04 1997-09-02 Bristol-Myers Squibb Company Sulfated α-glycolipid derivatives as cell adhesion inhibitors
DE4408248A1 (de) 1994-03-11 1995-09-14 Hoechst Ag Physiologisch verträgliche und physiologisch abbaubare Kohlenhydrat-Mimetika, ein Verfahren zur Herstellung und ihre Verwendung
EP0671409A3 (de) 1994-03-11 1996-06-12 Hoechst Ag Malonsäurederivate mit antiadhäsiven Eigenschaften.
US5444050A (en) 1994-04-29 1995-08-22 Texas Biotechnology Corporation Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa
HUT77345A (hu) 1994-04-29 1998-03-30 Texas Biotechnology Corporation E-szelektin, P-szelektin vagy L-szelektin szialil-Lewis x-hez vagy szialil-Lewis a-hoz kapcsolódását gátló mannopiranoziloxi-bifenil származékok és ezeket tartalmazó gyógyszerkészítmények
US5486536A (en) 1994-08-15 1996-01-23 The Regents Of The University Of Michigan Sulfatides as anti-inflammatory compounds
JPH0899989A (ja) 1994-09-30 1996-04-16 Akira Hasegawa 新規糖脂質誘導体およびその製造用中間体
DE4436164A1 (de) 1994-10-10 1996-04-11 Hoechst Ag Neue Kohlenhydratkonjugate als Inhibitoren der Zelladhäsion
US5686426A (en) 1994-11-17 1997-11-11 Bristol-Myers Squibb Company Dicarboxymethylated glycolipid derivatives as cell adhesion inhibitors
US6492332B1 (en) 1995-12-12 2002-12-10 Omeros Corporation Irrigation solution and methods for inhibition of tumor cell adhesion, pain and inflammation
US5639734A (en) 1994-12-20 1997-06-17 Esko; Jeffrey D. Disaccharide inflammation inhibitors and uses thereof
US20020040008A1 (en) 1995-01-24 2002-04-04 Wagner Denisa D. Method for treating and preventing atherosclerosis
US5736533A (en) 1995-06-07 1998-04-07 Neose Technologies, Inc. Bacterial inhibition with an oligosaccharide compound
PL324258A1 (en) * 1995-06-29 1998-05-11 Ciba Geigy Ag Diglycosiled 1,2-dioles mimetisingly acting on sialed lewis x and sialed lewis a
US5876715A (en) 1995-08-17 1999-03-02 The Biomembrane Institute Antibodies that bind novel carbohydrate ligands (myelorollins) that cause E-selectin dependent cell rolling, and uses thereof
DE19532902A1 (de) 1995-09-06 1997-03-13 Hoechst Ag Neuartige Glycomimetika als Selektin-Antagonisten und daraus hergestellte entzündungshemmend wirkende Arzneimittel
DE19537334A1 (de) 1995-10-09 1997-04-10 Hoechst Ag Antiadhäsive Piperidin- und Pyrrolidin-Carbonsäuren
US5919769A (en) 1995-10-26 1999-07-06 Kanebo, Ltd Fucose derivatives, drugs containing the same as active ingredient, and intermediates for producing the same
US5747463A (en) 1995-11-13 1998-05-05 Bristol-Myers Squibb Company Malonate derivatives of glycolipids as cell adhesion inhibitors
DE19602355A1 (de) 1996-01-24 1997-07-31 Hoechst Ag Mehrfach fucosylierte Dicarbonsäuren mit antiadhäsiven Eigenschaften
ATE357452T1 (de) 1996-01-30 2007-04-15 Glycomimetics Inc Sialyl-lewisa und sialyl lewisx epitop-analoge
EP0886639B1 (en) 1996-01-30 2008-05-28 GlycoMimetics, Inc. SIALYL-LEWISa AND SIALYL-LEWISx EPITOPE ANALOGUES
US5710023A (en) 1996-03-01 1998-01-20 Genetics Institute, Inc. IL-13 cytokine receptor chain
WO1997031625A1 (en) 1996-03-01 1997-09-04 The Regents Of The University Of California Inhibition of selectin binding
US5654412A (en) 1996-05-29 1997-08-05 Glycomed Incorporated Processes for the synthesis of sialyl Lewisx compounds
US5994402A (en) 1996-06-05 1999-11-30 Rotstein; Ori D. Anti-inflammatory and anti-pyretic method
US5919768A (en) 1996-06-26 1999-07-06 Texas Biotechnology Corporation Di- and trivalent small molecule selectin inhibitors
US5830871A (en) 1996-10-28 1998-11-03 The Scripps Research Institute Inhibitors of E-, P- and L-selectin binding
GB9618520D0 (en) 1996-09-05 1996-10-16 Chiroscience Ltd Compounds and their therapeutic use
US6110897A (en) 1996-10-10 2000-08-29 Glycorex Ab Antiinflammatory cell adhesion inhibitors
CA2281684C (en) 1997-02-28 2006-08-29 The Regents Of The University Of California Inhibition of cell-cell binding by lipid assemblies
US6120751A (en) 1997-03-21 2000-09-19 Imarx Pharmaceutical Corp. Charged lipids and uses for the same
SE9701127D0 (sv) 1997-03-26 1997-03-26 Karolinska Innovations Ab Antigenic fusionprotein carrying GALal, 3GAL epitopes
US5916910A (en) 1997-06-04 1999-06-29 Medinox, Inc. Conjugates of dithiocarbamates with pharmacologically active agents and uses therefore
US6193973B1 (en) 1997-08-22 2001-02-27 B. David Tuttle Dietary supplement for boosting energy and increasing muscular strength
US5948628A (en) 1997-09-05 1999-09-07 The Board Of Regents Of The University Of Oklahoma Methods of screening for compounds which mimic galectin-1
WO1999043353A2 (en) 1998-02-26 1999-09-02 Boehringer Ingelheim Pharmaceuticals, Inc. Combination anti-selectin and immunosuppressant therapy
US6365365B1 (en) 1998-03-20 2002-04-02 The Regents Of The University Of California Method of determining whether an agent modulates glycosyl sulfotransferase-3
US6265192B1 (en) 1998-03-20 2001-07-24 The Regents Of The University Of California Glycosly sulfortransferase-3
US6037333A (en) 1998-05-07 2000-03-14 Trustees Of Tufts College Microbe-inhibiting compositions
MXPA00012586A (es) 1998-06-16 2004-05-21 Univ Oklahoma Glicosulfopeptidos y metodos de sintesis y uso de los mismos.
US6503885B1 (en) 1998-09-21 2003-01-07 Otsuka Pharmaceutical Co., Ltd. Carboxymethylgalactose derivatives
CA2348781A1 (en) 1998-11-12 2000-05-25 Novolytics Inc. Compositions and methods for producing vascular occlusion
EP1289552B1 (en) 2000-05-19 2006-03-29 The Center for Blood Research, INC. Methods for treating hemostatic disorders by soluble p-selectin
US20020132220A1 (en) 2000-12-27 2002-09-19 Berens Kurt L. Use of selectin antagonists in organ preservation solutions
US7087212B2 (en) 2001-08-17 2006-08-08 Mallinckrodt, Inc Multicomponent assemblies having enhanced binding properties for diagnosis and therapy
LT2264043T (lt) * 2005-09-02 2017-12-11 Glycomimetics, Inc. Heterobifunkciniai pan-selektino inhibitoriai

Also Published As

Publication number Publication date
JP5298020B2 (ja) 2013-09-25
US20110257380A1 (en) 2011-10-20
JP2013189471A (ja) 2013-09-26
CA2666103A1 (en) 2008-05-22
EP2074132A2 (en) 2009-07-01
WO2008060378A3 (en) 2008-10-02
US20080161546A1 (en) 2008-07-03
EP2074132B1 (en) 2013-05-15
US7964569B2 (en) 2011-06-21
JP2010506832A (ja) 2010-03-04
WO2008060378A2 (en) 2008-05-22

Similar Documents

Publication Publication Date Title
CA2666103C (en) Glycomimetic replacements for hexoses and n-acetyl hexosamines
JP5511390B2 (ja) ヘキソースおよびn−アセチルヘキソサミンの置換体を有する糖模倣体の使用方法
US6207820B1 (en) Combinatorial library of moenomycin analogs and methods of producing same
EA005133B1 (ru) Полисахариды с антитромботической активностью, содержащие по меньшей мере одну ковалентную связь с биотином или производным биотина
JPH08511234A (ja) グリコシド結合の溶液及び固相形成
CN107709343B (zh) 针对肺炎链球菌血清型5的疫苗
Hashihayata et al. Convergent total syntheses of oligosaccharides by one-pot sequential stereoselective glycosylations
US6759390B2 (en) Compounds and their uses
US6716826B2 (en) Compounds and their uses
CA2925028A1 (en) Glycoclusters and their pharmaceutical use as antibacterials
EP1140959A1 (en) Inositol-containing hexasaccharides, their synthesis and their uses
Basu et al. Synthetic routes toward the trisaccharide related to the lipopolysaccharide of Burkholderia sp. HKI-402 (B4)
WO2017071152A1 (zh) 磷酰甘露五糖及其衍生物,及其制备方法和应用
JP6353849B2 (ja) Bace−1の阻害剤としての糖樹状クラスター化合物
US6953781B2 (en) Compounds and their uses
WO2012062996A1 (fr) Derives de 6-amino-6-desoxyglucosamine et leur utilisation comme agents antibacteriens
Austin Anti-Adhesion Carbohydrates for Prevention of Biofilm Formation
JPH0782292A (ja) 新規なグリチルレチン酸関連化合物又はそれらの塩
US20090247732A1 (en) Synthesis of glycopeptides with superior pharmacokinetic properties
Kaeothip Development of New Strategies for Expeditious Oligosaccharide Synthesis
Banerjee Stereoselective glycosylation and chemical ligation-applications in oligosaccharide and peptide synthesis
Yasomanee Picolinyl-assisted approaches to stereocontrolled glycosylation
Vinogradova Stereoselective glycosylation strategies: From mechanistic comprehension to practical applications
Park Chiral auxiliaries for 1, 2-cis stereoselective glycosylations

Legal Events

Date Code Title Description
EEER Examination request