CA2968391C - Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors - Google Patents

Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors Download PDF

Info

Publication number
CA2968391C
CA2968391C CA2968391A CA2968391A CA2968391C CA 2968391 C CA2968391 C CA 2968391C CA 2968391 A CA2968391 A CA 2968391A CA 2968391 A CA2968391 A CA 2968391A CA 2968391 C CA2968391 C CA 2968391C
Authority
CA
Canada
Prior art keywords
compound
group
linker
groups
compound according
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
CA2968391A
Other languages
English (en)
French (fr)
Other versions
CA2968391A1 (en
Inventor
John L. Magnani
Arun K. Sarkar
John M. Peterson
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 CA2968391A1 publication Critical patent/CA2968391A1/en
Application granted granted Critical
Publication of CA2968391C publication Critical patent/CA2968391C/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
    • 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
    • C07H15/26Acyclic or carbocyclic radicals, substituted by hetero rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/04Antineoplastic agents specific for metastasis
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2968391A 2014-12-03 2015-12-01 Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors Active CA2968391C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462087085P 2014-12-03 2014-12-03
US62/087,085 2014-12-03
PCT/US2015/063191 WO2016089872A1 (en) 2014-12-03 2015-12-01 Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors

Publications (2)

Publication Number Publication Date
CA2968391A1 CA2968391A1 (en) 2016-06-09
CA2968391C true CA2968391C (en) 2022-04-26

Family

ID=56092327

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2968391A Active CA2968391C (en) 2014-12-03 2015-12-01 Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors

Country Status (16)

Country Link
US (1) US10519181B2 (enExample)
EP (2) EP3227310B1 (enExample)
JP (2) JP6689854B2 (enExample)
KR (1) KR102542750B1 (enExample)
CN (1) CN107108679B (enExample)
AU (1) AU2015355136B2 (enExample)
CA (1) CA2968391C (enExample)
CY (1) CY1122038T1 (enExample)
DK (1) DK3227310T3 (enExample)
ES (1) ES2754549T3 (enExample)
HU (1) HUE045542T2 (enExample)
LT (1) LT3227310T (enExample)
PL (1) PL3227310T3 (enExample)
PT (1) PT3227310T (enExample)
SI (1) SI3227310T1 (enExample)
WO (1) WO2016089872A1 (enExample)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10519181B2 (en) 2014-12-03 2019-12-31 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors
JP6958820B2 (ja) 2015-12-14 2021-11-02 エックス4 ファーマシューティカルズ, インコーポレイテッド がんを処置する方法
WO2017151708A1 (en) 2016-03-02 2017-09-08 Glycomimetics, Inc. Methods for the treatment and/or prevention of cardiovescular disease by inhibition of e-selectin
WO2017177230A1 (en) 2016-04-08 2017-10-12 X4 Pharmaceuticals, Inc. Methods for treating cancer
JP2019524791A (ja) * 2016-08-08 2019-09-05 グリコミメティクス, インコーポレイテッド E−セレクチンの阻害剤もしくはcxcr4の阻害剤との、またはe−セレクチンおよびcxcr4両方のヘテロ二機能性阻害剤とのt細胞チェックポイント阻害剤の組み合わせ
CN117298287A (zh) 2016-10-07 2023-12-29 糖模拟物有限公司 高效的多聚体e-选择蛋白拮抗剂
WO2018169853A1 (en) 2017-03-15 2018-09-20 Glycomimetics, Inc. Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists
JP7275131B2 (ja) * 2017-11-30 2023-05-17 グリコミメティクス, インコーポレイテッド 骨髄浸潤リンパ球を動員する方法、およびその使用
WO2019133878A1 (en) 2017-12-29 2019-07-04 Glycomimetics, Inc. Heterobifunctional inhibitors of e-selectin and galectin-3
WO2019173229A1 (en) 2018-03-05 2019-09-12 Glycomimetics, Inc. Methods for treating acute myeloid leukemia and related conditions
WO2020123435A2 (en) 2018-12-10 2020-06-18 Glycomimetics, Inc. Methods of treating hiv and aids and the elimination of latent reservoirs of hiv infection using selectin, galectin, and siglec antagonists
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3
EP3911307A1 (en) 2019-01-14 2021-11-24 GlycoMimetics, Inc. Selectin or galectin antagonists for treating cytokine release syndrome and crs-induced neurotoxicity
AU2020263266A1 (en) 2019-04-24 2021-12-16 Glycomimetics, Inc. Galactose-linked multimeric glycomimetic inhibitors of E-selectins, galectin-3, and/or CXCR4 chemokine receptors
WO2021011435A1 (en) 2019-07-12 2021-01-21 Magnani John L Methods for use of gene expression as an indicator of e-selectin inhibitor efficacy and clinical outcome for multiple tumor types
EP4003367A1 (en) * 2019-07-31 2022-06-01 GlycoMimetics, Inc. Use of e-selectin antagonists to enhance the survival of reconstituted, bone marrow-depleted hosts
JP2023517956A (ja) 2020-03-10 2023-04-27 エックス4 ファーマシューティカルズ, インコーポレイテッド 好中球減少症を処置する方法
WO2021195465A1 (en) * 2020-03-27 2021-09-30 Magnani John L Treatment of acute respiratory distress syndrome and related conditions with antagonists of e-selectin
JP2023527411A (ja) 2020-05-31 2023-06-28 グリコミメティクス, インコーポレイテッド がん細胞の負荷を減少させ、正常な造血を保護するための化合物および方法
AU2021292458A1 (en) 2020-06-14 2023-01-19 GlycoMimetics Compositions and methods for overcoming microenvironment-mediated resistance via e-selectin targeting
US20240269157A1 (en) 2021-08-03 2024-08-15 Glycomimetics, Inc. Compositions and methods for overcoming microenvironment-mediated resistance via e-selectin targeting

Family Cites Families (239)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7409399A (nl) 1973-07-19 1975-01-21 Rhone Poulenc Sa Werkwijze ter bereiding van thermostabiele har- sen en voorwerpen geheel of gedeeltelijk be- staande uit deze harsen.
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
ATE94395T1 (de) 1986-05-09 1993-10-15 Pulverer Gerhard 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
US5079353A (en) 1987-12-02 1992-01-07 Chembiomed, Ltd. Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation
US5632991A (en) 1988-11-14 1997-05-27 Brigham & Women's Hospital Antibodies specific for E-selectin and the uses thereof
EP0381310A1 (en) 1989-01-30 1990-08-08 The Biomembrane Institute Monoclonal antibodies directed to tumor-associated gangliosides and fucogangliosides and method for production thereof
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
US5272263A (en) 1989-04-28 1993-12-21 Biogen, Inc. DNA sequences encoding vascular cell adhesion molecules (VCAMS)
EP0585963A1 (en) 1989-05-23 1994-03-09 Otsuka Pharmaceutical Co., Ltd. Monoclonal antibodies to CMP-170 antigen on activated endothelial cells
US6033665A (en) 1989-09-27 2000-03-07 Elan Pharmaceuticals, Inc. Compositions and methods for modulating leukocyte adhesion to brain endothelial cells
US6001988A (en) 1990-06-11 1999-12-14 Nexstar Pharmaceuticals, Inc. High affinity nucleic acid ligands to lectins
US6280932B1 (en) 1990-06-11 2001-08-28 Gilead Sciences, Inc. High affinity nucleic acid ligands to lectins
US5576305A (en) 1990-06-15 1996-11-19 Cytel Corporation Intercellular adhesion mediators
US5753631A (en) 1990-06-15 1998-05-19 Cytel Corporation Intercellular adhesion mediators
WO1991019501A1 (en) 1990-06-15 1991-12-26 Cytel Corporation Intercellular adhesion mediators
US6387884B1 (en) 1990-06-18 2002-05-14 Stanford University Leukocyte homing modulation
US6391857B1 (en) 1990-06-18 2002-05-21 Stanford University Methods and compositions for endothelial binding
WO1992001718A2 (en) 1990-07-17 1992-02-06 Board Of Regents Of The University Of Oklahoma Functionally active selectin-derived peptides and ligand for gmp-140
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
US5648344A (en) 1990-07-30 1997-07-15 Glycomed Incorporated Methods of treating inflammation using selection binding compounds
US5789573A (en) 1990-08-14 1998-08-04 Isis Pharmaceuticals, Inc. Antisense inhibition of ICAM-1, E-selectin, and CMV IE1/IE2
NZ240316A (en) 1990-10-25 1996-12-20 Univ Michigan Compound for treating disease mediated by the elaboration of elam-1 on endothelial cells
HUT64476A (en) 1990-11-23 1994-01-28 Gen Hospital Corp Process for inhibiting interacton between proteins and carbohydrate causing cell-adhesion
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
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
US6124267A (en) 1991-02-05 2000-09-26 Southpac Trust Internationals, Inc. O-glycan inhibitors of selectin mediated inflammation derived from PSGL-1
US6121233A (en) 1991-04-19 2000-09-19 John L. Magnani Methods for the inhibition of cancer metastasis mediated by endothelial adhesion molecules
AU660995B2 (en) 1991-05-06 1995-07-13 Genentech Inc. Glycam-1 (Sgp 50), a selectin ligand
US5318890A (en) 1991-05-06 1994-06-07 The Regents Of The University Of California Assays for inhibitors of leukocyte adhesion
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
US5580858A (en) 1991-06-10 1996-12-03 Alberta Research Council Immunosuppressive and tolerogenic modified Lewisx compounds
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
CA2104099A1 (en) 1991-12-18 1993-06-19 George A. Heavner Peptide inhibitors of inflammation mediated by selectins
US5643873A (en) 1992-05-06 1997-07-01 Affymax Technologies N.V. Peptides and compounds that bind selectins including endothelial leukocyte adhesion molecule 1
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
US5710123A (en) 1992-12-18 1998-01-20 Centocor, Inc. Peptide inhibitors of selectin binding
DE69322289T2 (de) 1992-12-29 1999-05-20 Genentech, Inc., South San Francisco, Calif. Behandlung von entzündlichen darmerkrankungen mit interferon-gamma-inhibitoren
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
EP0700301B1 (en) 1993-05-05 1999-09-01 Affymax Technologies N.V. Peptides and compounds that bind to elam-1
US5527785A (en) 1993-05-14 1996-06-18 The Regents Of The University Of California Selectin receptor modulating compositions
SE9301677L (sv) 1993-05-14 1994-11-18 Kurt G I Nilsson Syntesmetod
FI955467A7 (fi) 1993-05-14 1995-12-19 Cytel Corp Soluadheesion inhibiittoreina toimivia Sialyl Lex-analogeja
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
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
DK0730608T3 (da) 1993-05-17 2002-07-22 Avant Immunotherapeutics Inc Præparater omfattende komplementrelaterede proteiner og carbohydrater og fremgangsmåder til fremstilling og anvendelse af præparaterne
US5856300A (en) 1994-05-12 1999-01-05 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
US5750508A (en) 1993-06-16 1998-05-12 Glycomed Incorporated Sialic acid/fucose based medicaments
US5658880A (en) 1993-06-16 1997-08-19 Glycomed Incorporated Sialic acid/fucose based medicaments
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
US5679321A (en) 1993-06-17 1997-10-21 Glycomed Incorporated Sialic acid/fucose based medicaments
DK76193D0 (da) 1993-06-25 1993-06-25 Astra Ab Kulhydratderivater
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
WO1995005830A1 (en) 1993-08-20 1995-03-02 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
WO1995010296A1 (en) 1993-10-12 1995-04-20 Glycomed Incorporated 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.
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
US5444050A (en) 1994-04-29 1995-08-22 Texas Biotechnology Corporation Binding of E-selectin or P-selectin to sialyl Lewisx or sialyl-Lewisa
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
CA2209084A1 (en) 1994-12-28 1996-07-04 Hiroshi Miyauchi Lewis x derivative and process for producing the same
US20020040008A1 (en) 1995-01-24 2002-04-04 Wagner Denisa D. Method for treating and preventing atherosclerosis
US5527936A (en) 1995-02-17 1996-06-18 E. I. Du Pont De Nemours And Company Hydrosilylation of unsaturated compounds
GB9504065D0 (en) 1995-03-01 1995-04-19 Pharmacia Spa Poly-pyrrolecarboxamidonaphthalenic acid derivatives
GB9511357D0 (en) 1995-06-06 1995-08-02 Johnson Matthey Plc Improved antiviral compounds
US6506770B1 (en) 1996-06-06 2003-01-14 Anormed, Inc. Antiviral compounds
US5736533A (en) 1995-06-07 1998-04-07 Neose Technologies, Inc. Bacterial inhibition with an oligosaccharide compound
WO1996040942A1 (en) 1995-06-07 1996-12-19 Cytel Corporation Humanized antibodies to e-selectin
CA2224346A1 (en) 1995-06-29 1997-01-16 Novartis Ag Diglycosylated 1,2-diols as mimetics of sialyl-lewis x and sialyl-lewis a
WO1997001335A1 (en) 1995-06-29 1997-01-16 Texas Biotechnology Corporation Di- and trivalent small molecule selectin inhibitors
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
AU7445796A (en) 1995-10-18 1997-05-07 Cytel Corporation Sialyl lex analogues as inhibitors of cellular adhesion
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
JPH09176047A (ja) 1995-12-25 1997-07-08 Unitika Ltd 外用医薬製剤
DE19602355A1 (de) 1996-01-24 1997-07-31 Hoechst Ag Mehrfach fucosylierte Dicarbonsäuren mit antiadhäsiven Eigenschaften
AU1542397A (en) 1996-01-30 1997-08-22 Novartis Ag Sialyl-lewisa and sialyl-lewisx epitope analogues
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
EP0902681B1 (en) 1996-03-01 2002-05-22 The Regents of the University of California Inhibition of selectin binding
US6344545B1 (en) 1996-06-14 2002-02-05 Progenics Pharmaceuticals, Inc. Method for preventing HIV-1 infection of CD4+ cells
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
CA2260854A1 (en) 1996-08-08 1998-02-19 Novartis Ag Modified oligosaccharides
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
US6592872B1 (en) 1996-09-17 2003-07-15 The United States Of America As Represented By The Department Of Health And Human Services Targeting antigens to the MHC class I processing pathway with an anthrax toxin fusion protein
JP2001501612A (ja) 1996-09-27 2001-02-06 ザ・トラスティーズ・オブ・コランビア・ユニバーシティー・イン・ザ・シティー・オブ・ニューヨーク 虚血性疾患を治療する方法及び発作後の症状を改善する方法
US6110897A (en) 1996-10-10 2000-08-29 Glycorex Ab Antiinflammatory cell adhesion inhibitors
AU7180398A (en) 1996-11-13 1998-06-03 Morphogenesis, Inc. Antibody MG1 recognizing a small subset of human hematopoietic cells
US6235309B1 (en) 1997-02-28 2001-05-22 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
JP3720520B2 (ja) 1997-03-27 2005-11-30 タカラバイオ株式会社 糖と標的物との相互作用の測定方法
US6413760B1 (en) 1997-04-15 2002-07-02 Genetics Institute, Inc. Highly purified mocarhagin cobra venom protease polynucleotides endcoding same and related proteases and therapeutic uses thereof
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
US7018637B2 (en) 1998-02-23 2006-03-28 Aventis Pasteur, Inc Multi-oligosaccharide glycoconjugate bacterial meningitis vaccines
AU8967998A (en) 1998-02-25 1999-09-15 Hsc Research & Development Limited Partnership Antibiotic-ligand conjugates and methods of use thereof
WO1999043353A2 (en) 1998-02-26 1999-09-02 Boehringer Ingelheim Pharmaceuticals, Inc. Combination anti-selectin and immunosuppressant therapy
CA2245224A1 (en) 1998-08-14 2000-02-14 Jiang-Hong Giong Chemokine receptor antagonists and chemotherapeutics
US6458777B1 (en) 1998-03-13 2002-10-01 Mucosal Therapeutics Llc Methods and compositions for treating and preventing mucositis
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
WO1999061055A1 (en) 1998-05-22 1999-12-02 The Board Of Trustees Of The Leland Stanford Junior University Bifunctional molecules and therapies based thereon
EP1087996B1 (en) 1998-06-16 2007-01-17 The Board of Regents of The University of Oklahoma Glycosulfopeptides and methods of synthesis and use thereof
US6004815A (en) 1998-08-13 1999-12-21 The Regents Of The University Of California Bacteria expressing nonsecreted cytolysin as intracellular microbial delivery vehicles to eukaryotic cells
CA2344652C (en) 1998-09-21 2007-11-20 Otsuka Pharmaceutical Co., Ltd. Carboxymethylgalactose derivatives
US6960566B1 (en) 1998-11-06 2005-11-01 The Wister Institute of Anatomy and Biology Compositions and methods for treatment of cancer
IL142864A0 (en) 1998-11-12 2002-03-10 Novolytics Inc Compositions and methods for producing vascular occlusion
GB9904387D0 (en) 1999-02-25 1999-04-21 Pharmacia & Upjohn Spa Antitumour synergistic composition
AU4692400A (en) * 1999-05-03 2000-11-17 Smithkline Beecham Corporation Cxcr-4 receptor antagonists - thrombopoietin mimetics
US6515117B2 (en) 1999-10-12 2003-02-04 Bristol-Myers Squibb Company C-aryl glucoside SGLT2 inhibitors and method
US6887842B1 (en) 1999-11-19 2005-05-03 The Board Of Trustees Of The Leland Stanford Junior University Modulating a pharmacokinetic property of a drug by administering a bifunctional molecule containing the drug
US7204981B2 (en) 2000-03-28 2007-04-17 Eli Lilly And Company Methods of treating diseases with activated protein C
US6683056B2 (en) 2000-03-30 2004-01-27 Bristol-Myers Squibb Company O-aryl glucoside SGLT2 inhibitors and method
CA2404890C (en) 2000-03-30 2013-11-19 Whitehead Institute For Biomedical Research Rna sequence-specific mediators of rna interference
ATE321570T1 (de) 2000-05-19 2006-04-15 Blood Res Center Verfahren zur behandlung von hämostatischen störungen durch lösliches p-selectin
US20020165178A1 (en) 2000-06-28 2002-11-07 Christian Schetter Immunostimulatory nucleic acids for the treatment of anemia, thrombocytopenia, and neutropenia
EP1325123A4 (en) 2000-09-12 2004-07-21 Inst Genetics Llc INHIBITION OF STENOSIS OR RESTENOSIS USING P-SELECTINE ANTAGONISTS
JP2004523479A (ja) 2000-10-18 2004-08-05 マサチューセッツ インスティテュート オブ テクノロジー 多糖の肺送達に関する方法および産物
CA2428721A1 (en) 2000-11-14 2002-05-23 The General Hospital Corporation Blockade of t cell migration into epithelial gvhd target tissues
WO2002062810A2 (en) 2000-11-29 2002-08-15 Bracco International B.V. Linkable sialyl lewis x analogs
US20020132220A1 (en) 2000-12-27 2002-09-19 Berens Kurt L. Use of selectin antagonists in organ preservation solutions
CN101694497B (zh) 2001-03-28 2014-11-26 哈佛大学校长及研究员协会 将外源蛋白递送到胞质溶胶中的方法,及其用途
US20030198639A1 (en) 2002-04-16 2003-10-23 Frenette Paul S. Methods of treating sickle cell disease
US7087212B2 (en) 2001-08-17 2006-08-08 Mallinckrodt, Inc Multicomponent assemblies having enhanced binding properties for diagnosis and therapy
WO2003032925A2 (en) 2001-10-19 2003-04-24 Cummings Richard D Glycosulfopeptide inhibitors and methods of use thereof
WO2003049684A2 (en) 2001-12-07 2003-06-19 Centocor, Inc. Pseudo-antibody constructs
MXPA04006136A (es) 2001-12-21 2004-11-01 Anormed Inc Compuestos heterociclicos que se unen a receptor de quimiocina con eficacia incrementada.
US20030186942A1 (en) 2002-01-16 2003-10-02 Crooks Peter A. Compounds of use in the treatment of epilepsy, seizure, and electroconvulsive disorders
EP1542704A1 (en) 2002-04-18 2005-06-22 Stephen H. Embury Method and composition for preventing pain in sickle cell patients
US7060685B2 (en) 2002-05-16 2006-06-13 Glycomimetics, Inc. Compounds and methods for inhibiting selectin-mediated function
US20040096396A1 (en) 2002-07-03 2004-05-20 Glycomimetics, Inc. Compositions and methods for diagnosis and therapy of medical conditions involving angiogenesis
US7556806B2 (en) 2002-10-11 2009-07-07 University Of Maryland Biotechnology Institute Carbohydrate-based synthetic vaccines for HIV
JP2006515306A (ja) 2002-12-20 2006-05-25 グリコミメティクス, インコーポレイテッド Pseudomonas細菌感染の処置のためのオリゴ糖およびその結合体
US6844125B2 (en) 2003-03-20 2005-01-18 Kabushiki Kaisha Toshiba Combination of developing agents, image forming apparatus, and method for forming image
US7332334B2 (en) 2003-04-18 2008-02-19 Oklahoma Medical Research Foundation Hematopoietic stem cells treated by in vitro fucosylation and methods of use
US20040219158A1 (en) 2003-05-02 2004-11-04 Glycomimetics, Inc. Compositions and methods for diagnosis and therapy of medical conditions involving infection with pseudomonas bacteria
US20050054614A1 (en) 2003-08-14 2005-03-10 Diacovo Thomas G. Methods of inhibiting leukocyte accumulation
US7041226B2 (en) 2003-11-04 2006-05-09 Lexmark International, Inc. Methods for improving flow through fluidic channels
US20050214283A1 (en) 2003-11-07 2005-09-29 Robert Sackstein Antibodies to CD44 glycoforms and uses thereof
US7361644B2 (en) 2003-11-19 2008-04-22 Glycomimetics, Inc. Specific antagonist for both E- and P-selectins
CA2546784A1 (en) 2003-11-19 2005-06-16 Glycomimetics, Inc. Glycomimetic antagonists for both e- and p-selectins
MXPA06006901A (es) 2003-12-18 2006-09-04 Unibioscreen Sa Derivados de esteroides glicosilados con actividad antimigratoria.
GB0404434D0 (en) 2004-02-27 2004-03-31 Novartis Ag Organic compounds
WO2005116088A2 (en) 2004-05-25 2005-12-08 The Johns Hopkins University Methods and compositions for treating diseases and disorders associated with siglec-8 expressing cells
WO2006002382A2 (en) 2004-06-24 2006-01-05 The Scripps Research Institute Arrays with cleavable linkers
WO2006017180A2 (en) 2004-07-09 2006-02-16 Progenics Pharmaceuticals, Inc. Glycopeptide dimers and uses thereof
EP1790639B1 (en) 2004-08-27 2014-03-26 Ono Pharmaceutical Co., Ltd. Spirocyclic compounds and their use as cxcr4-antagonists
WO2006062946A2 (en) 2004-12-06 2006-06-15 University Of Florida Research Foundation, Inc. Incorporation of bone marrow derived stem cells in tumors
MX2007008328A (es) 2005-01-07 2008-01-16 Univ Emory Antagonistas cxcr4 para el tratamiento de trastornos medicos.
US8008312B2 (en) 2005-01-07 2011-08-30 Emory University CXCR4 antagonists for the treatment of HIV infection
EP1885356A2 (en) 2005-02-17 2008-02-13 Icos Corporation Phosphoinositide 3-kinase inhibitors for inhibiting leukocyte accumulation
US20060217303A1 (en) 2005-03-25 2006-09-28 Wisconsin Alumni Research Foundation Compounds and Methods for Treating Seizure Disorders
WO2006127906A1 (en) 2005-05-25 2006-11-30 Glycomimetics, Inc. Heterobifunctional compounds for selectin inhibition
US20060287253A1 (en) 2005-06-17 2006-12-21 Kriegler Steven M Compounds and methods for treating seizure disorders
US20070021378A1 (en) 2005-07-22 2007-01-25 The Regents Of The University Of California Heparin compositions and selectin inhibition
AU2006280101B2 (en) 2005-08-09 2012-06-28 Glycomimetics, Inc. Glycomimetic inhibitors of the PA-IL lectin, PA-IIL lectin or both the lectins from Pseudomonas
US20070059242A1 (en) 2005-08-15 2007-03-15 Paul Wentworth Methods to identify therapeutic agents
WO2007022385A2 (en) 2005-08-18 2007-02-22 Novartis Ag Use of cxcr4 binding molecules for the treatment of whim syndrome
US7728117B2 (en) 2005-09-02 2010-06-01 Glycomimetics, Inc. Heterobifunctional pan-selectin inhibitors
CA2663633A1 (en) 2005-09-14 2007-03-22 Lai-Xi Wang Synthetic polyvalent carbohydrates as components of microbicides
WO2007143052A1 (en) 2006-06-01 2007-12-13 Glycomimetics, Inc. Galactosides and thiodigalactosides as inhibitors of pa-il lectin from pseudomonas
EP2029164B1 (en) 2006-06-07 2015-12-23 The Board of Trustees of the Leland Stanford Junior University Anti-leukocyte recruitment therapy for the treatment of seizures and epilepsy
WO2008002449A2 (en) 2006-06-23 2008-01-03 Glycomimetics, Inc. Glycomimetic inhibitors of siglec-8
US20080227799A1 (en) 2006-07-11 2008-09-18 Liotta Dennis C CXCR4 Antagonists Including Heteroatoms for the Treatment of Medical Disorders
US8080659B2 (en) 2006-07-11 2011-12-20 Emory University CXCR4 antagonists including diazine and triazine structures for the treatment of medical disorders
WO2008008852A2 (en) 2006-07-11 2008-01-17 Emory University Cxcr4 antagonists including heteroatoms for the treatment of medical disorders
US7998740B2 (en) 2006-07-18 2011-08-16 Robert Sackstein Cytokine induction of selectin ligands on cells
WO2008060378A2 (en) 2006-10-12 2008-05-22 Glycomimetics, Inc. Glycomimetic replacements for hexoses and n-acetyl hexosamines
US20080306098A1 (en) 2006-11-06 2008-12-11 Mutz Mitchell W Pharmacokinetics of protease inhibitors and other drugs
WO2008087259A1 (en) 2007-01-18 2008-07-24 Suomen Punainen Risti, Veripalvelu Novel carbohydrate profile compositions from human cells and methods for analysis and modification thereof
CA2677747A1 (en) 2007-02-09 2008-08-21 Glycomimetics, Inc. Methods of use of glycomimetics with replacements for hexoses and n-acetyl hexosamines
US20080261978A1 (en) 2007-03-08 2008-10-23 Clark Michael P Chemokine receptor modulators
US20090054334A1 (en) 2007-05-23 2009-02-26 Mutz Mitchell W Combinatorial improvement of bifunctional drug properties
US8039442B2 (en) 2007-07-18 2011-10-18 Glycomimetics, Inc. Compounds and methods for treatment of sickle cell disease or complications associated therewith
KR20100042654A (ko) 2007-08-08 2010-04-26 교와 핫꼬 기린 가부시키가이샤 단리된 세포 집단
WO2009049184A2 (en) 2007-10-12 2009-04-16 Transmolecular, Inc. Systemic administration of chlorotoxin agents for the diagnosis and treatment of tumors
FI20070853A0 (fi) 2007-11-09 2007-11-09 Glykos Finland Oy Glykaania sitovat monoklonaaliset vasta-aineet
WO2009073911A1 (en) 2007-12-10 2009-06-18 Mater Medical Research Institute Treatment and prophylaxis
WO2009126556A1 (en) 2008-04-08 2009-10-15 Glycomimetics, Inc. Pan-selectin inhibitor with enhanced pharmacokinetic activity
EP2318015B1 (en) 2008-06-13 2013-08-07 GlycoMimetics, Inc. Treatment of cancers of the blood using selected glycomimetic compounds
WO2010025416A1 (en) * 2008-08-29 2010-03-04 Genzyme Corporation Cxcr4 antagonists for kidney injury
US20100240773A1 (en) 2009-03-23 2010-09-23 Kenneth Korzekwa Multifunctional linkers
FI20095459A0 (fi) 2009-04-24 2009-04-24 Suomen Punainen Risti Veripalv Uusia määritysmenetelmiä
AU2010241807B2 (en) * 2009-05-01 2014-08-14 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors
US20120093782A1 (en) 2009-05-13 2012-04-19 Grove Robert I Enhanced Hematopoietic Stem Cell Engraftment
US20110251148A1 (en) 2010-04-07 2011-10-13 Glycomimetics, Inc. Glycomimetic compounds and methods to inhibit infection by hiv
US8921328B2 (en) 2010-09-14 2014-12-30 Glycomimetics, Inc. E-selectin antagonists
US20130261070A1 (en) 2010-10-04 2013-10-03 John L. Magnani Anti-epileptogenic agents
FI20106031A0 (fi) 2010-10-06 2010-10-06 Suomen Punainen Risti Veripalv Menetelmä solujen eristämiseksi ja menetelmällä eristetty solupopulaatio
WO2012061662A1 (en) 2010-11-03 2012-05-10 Glycomimetics, Inc. Glycomimetic-peptidomimetic inhibitors of e-selectins and cxcr4 chemokine receptors
US8765126B2 (en) 2011-05-05 2014-07-01 Robert Sackstein Methods of treating complications and disorders associated with G-CSF administration
US9109002B2 (en) 2011-12-22 2015-08-18 Glycomimetics, Inc. E-selectin antagonist compounds, compositions, and methods of use
CA2888527A1 (en) 2012-10-31 2014-05-08 Glycomimetics, Inc. E-selectin antagonists compounds and methods of use
PT2928476T (pt) 2012-12-07 2018-05-10 Glycomimetics Inc Compostos, composições e métodos que utilizam antagonistas de e-selectina para mobilização de células hematopoiéticas
WO2014149837A1 (en) 2013-03-15 2014-09-25 Glycomimetics, Inc. Compounds and methods to enhance the oral availability of glycomimetics
CA2925119A1 (en) 2013-09-30 2015-04-02 Glycomimetics, Inc. Methods and compositions for treating and/or preventing mucositis
US20160333043A1 (en) 2014-01-17 2016-11-17 Glycomimetics, Inc. E-Selectin Antagonists Modified By Macrocycle Formation to the Galactose
US10519181B2 (en) 2014-12-03 2019-12-31 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectins and CXCR4 chemokine receptors
WO2016164394A1 (en) 2015-04-08 2016-10-13 Glycomimetics, Inc. 2-halo-galactose-containing selectin antagonists
JP2019501130A (ja) 2015-12-02 2019-01-17 グリコミメティクス, インコーポレイテッド トリアゾールリンカーを有するヘテロ二官能性の汎セレクチン拮抗剤

Also Published As

Publication number Publication date
KR102542750B1 (ko) 2023-06-12
CA2968391A1 (en) 2016-06-09
CY1122038T1 (el) 2020-10-14
SI3227310T1 (sl) 2019-11-29
DK3227310T3 (da) 2019-09-30
EP3227310A4 (en) 2018-07-25
JP6689854B2 (ja) 2020-04-28
PL3227310T3 (pl) 2020-02-28
AU2015355136B2 (en) 2020-06-25
ES2754549T3 (es) 2020-04-20
AU2015355136A1 (en) 2017-06-08
EP3227310A1 (en) 2017-10-11
US20170305951A1 (en) 2017-10-26
US10519181B2 (en) 2019-12-31
NZ732034A (en) 2022-03-25
HUE045542T2 (hu) 2019-12-30
PT3227310T (pt) 2019-11-06
CN107108679B (zh) 2020-10-23
CN107108679A (zh) 2017-08-29
WO2016089872A1 (en) 2016-06-09
JP2020090553A (ja) 2020-06-11
KR20170085594A (ko) 2017-07-24
EP3227310B1 (en) 2019-07-31
LT3227310T (lt) 2019-09-10
BR112017011446A2 (pt) 2018-02-27
JP2017536395A (ja) 2017-12-07
EP3569609A1 (en) 2019-11-20

Similar Documents

Publication Publication Date Title
CA2968391C (en) Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
CA2891514C (en) Compounds, compositions and methods using e-selectin antagonists for mobilization of hematopoietic cells
US20170296566A9 (en) Methods and compositions for treating and/or preventing mucositis
US20150284420A1 (en) E-selectin antagonist compounds and methods of use
AU2023204344A1 (en) Highly potent multimeric E-selectin antagonists
WO2016164394A1 (en) 2-halo-galactose-containing selectin antagonists
WO2015109049A1 (en) E-selectin antagonists modified by macrocycle formation to the galactose
WO2020253814A1 (zh) 一类雷公藤红素衍生物、其制备方法及用途
HK1240233A1 (en) Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
HK1240233B (en) Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
EP4143200A1 (en) Cd33 ligands suitable for incorporation into carriers
NZ732034B2 (en) Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
WO2021222767A1 (en) Cd33 ligands suitable for incorporation into carriers
BR112017011446B1 (pt) Composto, composição e uso dos mesmos
CA3037989A1 (en) Pyrimidine prodrugs for the treatment of viral infections and further diseases
JP7382188B2 (ja) 2,6-ジ置換ピリジン誘導体からなる医薬
WO2014070988A1 (en) Compounds and methods to enhance the oral availability of glycomimetics