CA2803388C - Methods of inhibition of protein fucosylation in vivo using fucose analogs - Google Patents

Methods of inhibition of protein fucosylation in vivo using fucose analogs Download PDF

Info

Publication number
CA2803388C
CA2803388C CA2803388A CA2803388A CA2803388C CA 2803388 C CA2803388 C CA 2803388C CA 2803388 A CA2803388 A CA 2803388A CA 2803388 A CA2803388 A CA 2803388A CA 2803388 C CA2803388 C CA 2803388C
Authority
CA
Canada
Prior art keywords
fucose
analog
fucose analog
group
alkynyl
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
CA2803388A
Other languages
English (en)
French (fr)
Other versions
CA2803388A1 (en
Inventor
Peter Senter
Stephen Alley
Dennis Benjamin
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.)
Seagen Inc
Original Assignee
Seattle Genetics 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 Seattle Genetics Inc filed Critical Seattle Genetics Inc
Publication of CA2803388A1 publication Critical patent/CA2803388A1/en
Application granted granted Critical
Publication of CA2803388C publication Critical patent/CA2803388C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/7004Monosaccharides having only carbon, hydrogen and oxygen atoms
    • 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
    • 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
    • A61K31/7024Esters of saccharides
    • 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
    • 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
    • A61K31/7042Compounds having saccharide radicals and heterocyclic 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
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00Medicinal preparations containing antigens or antibodies
    • A61K39/0005Vertebrate antigens
    • A61K39/0011Cancer antigens
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61P37/00Drugs for immunological or allergic disorders
    • 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
    • C07KPEPTIDES
    • C07K16/00Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K16/00Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies
    • C07K16/18Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies against material from animals or humans
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00Medicinal preparations containing antigens or antibodies
    • A61K2039/51Medicinal preparations containing antigens or antibodies comprising whole cells, viruses or DNA/RNA
    • A61K2039/515Animal cells
    • A61K2039/5152Tumor cells
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00Medicinal preparations containing antigens or antibodies
    • A61K2039/54Medicinal preparations containing antigens or antibodies characterised by the route of administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00Medicinal preparations containing antigens or antibodies
    • A61K2039/545Medicinal preparations containing antigens or antibodies characterised by the dose, timing or administration schedule
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00Preparations for use in therapy
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K2317/00Immunoglobulins specific features
    • C07K2317/40Immunoglobulins specific features characterized by post-translational modification
    • C07K2317/41Glycosylation, sialylation, or fucosylation
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Immunology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
CA2803388A 2010-08-05 2011-08-05 Methods of inhibition of protein fucosylation in vivo using fucose analogs Active CA2803388C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US37111610P 2010-08-05 2010-08-05
US61/371,116 2010-08-05
PCT/US2011/046857 WO2012019165A2 (en) 2010-08-05 2011-08-05 Methods of inhibition of protein fucosylation in vivo using fucose analogs

Publications (2)

Publication Number Publication Date
CA2803388A1 CA2803388A1 (en) 2012-02-09
CA2803388C true CA2803388C (en) 2019-11-05

Family

ID=45560106

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2803388A Active CA2803388C (en) 2010-08-05 2011-08-05 Methods of inhibition of protein fucosylation in vivo using fucose analogs

Country Status (21)

Country Link
US (4) US9504702B2 (https=)
EP (2) EP2608796B1 (https=)
JP (4) JP5918235B2 (https=)
KR (2) KR20190022884A (https=)
CN (2) CN103402525B (https=)
AU (3) AU2011285490B2 (https=)
CA (1) CA2803388C (https=)
CY (1) CY1121419T1 (https=)
DK (1) DK2608796T3 (https=)
ES (1) ES2711622T3 (https=)
HU (1) HUE043370T2 (https=)
IL (2) IL224487A (https=)
MX (1) MX356671B (https=)
NZ (1) NZ606250A (https=)
PL (1) PL2608796T3 (https=)
PT (1) PT2608796T (https=)
RU (2) RU2625768C2 (https=)
SI (1) SI2608796T1 (https=)
TR (1) TR201902439T4 (https=)
WO (1) WO2012019165A2 (https=)
ZA (1) ZA201300653B (https=)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8163551B2 (en) 2008-05-02 2012-04-24 Seattle Genetics, Inc. Methods and compositions for making antibodies and antibody derivatives with reduced core fucosylation
DK2608796T3 (en) * 2010-08-05 2019-03-18 Seattle Genetics Inc Inhibition of protein fucosylation in vivo using fucose analogues
WO2014031875A1 (en) 2012-08-23 2014-02-27 Seattle Genetics, Inc. Treatment of sickle cell disease and inflammatory conditions
WO2014130613A2 (en) 2013-02-22 2014-08-28 Amgen Inc. Carbohydrate phosphonate derivatives as modulators of glycosylation
CN106699886A (zh) * 2015-07-13 2017-05-24 西藏海思科药业集团股份有限公司 抗体依赖性细胞介导的细胞毒性(adcc)增强的奥法木抗体
WO2017096274A1 (en) 2015-12-04 2017-06-08 Seattle Genetics, Inc. Cancer treatment using 2-deoxy-2-fluoro-l-fucose in combination with a checkpoint inhibitor
CA3022769A1 (en) 2016-05-10 2017-11-16 Ares Trading S.A. Methods for modulating protein galactosylation profiles of recombinant proteins using peracetyl galactose
JP2018002666A (ja) * 2016-07-04 2018-01-11 国立研究開発法人理化学研究所 フコース類似体と糖を検出する方法
JP7245177B2 (ja) * 2017-06-07 2023-03-23 シージェン インコーポレイテッド 低減した表面フコシル化を有するt細胞、及びそれを作製及び使用する方法
MX2020005662A (es) 2017-12-01 2020-08-20 Pfizer Anticuerpos anti-cxcr5 y composiciones y usos de los mismos.
CA3094756A1 (en) 2018-03-29 2019-10-03 Pfizer Inc. Lfa3 variants and compositions and uses thereof
JP2021534196A (ja) 2018-08-23 2021-12-09 シージェン インコーポレイテッド 抗tigit抗体
JP7446587B2 (ja) * 2018-12-27 2024-03-12 慶應義塾 抗ヒトノロウイルス剤
KR20220115998A (ko) * 2019-12-19 2022-08-19 메르크 파텐트 게엠베하 단백질의 글리코실화 프로파일을 조절하기 위한 방법 및 조성물
TWI877278B (zh) * 2019-12-30 2025-03-21 美商思進公司 以非海藻糖苷化抗-cd70抗體治療癌症之方法
IL272389A (en) 2020-01-30 2021-08-31 Yeda Res & Dev Kits containing antibodies to PD-L1 and their uses in therapy
JP2023528400A (ja) * 2020-06-03 2023-07-04 サイモン フレイザー ユニヴァーシティー タンパク質フコシル化の阻害剤及びその用途
AU2022238571A1 (en) 2021-03-18 2023-09-14 Seagen Inc. Selective drug release from internalized conjugates of biologically active compounds
EP4352094A1 (en) 2021-06-07 2024-04-17 Amgen Inc. Using fucosidase to control afucosylation level of glycosylated proteins
CN113413465B (zh) * 2021-06-15 2022-06-03 北京大学 岩藻糖基化抑制剂在抗癌导致炎症中的应用
WO2024118503A1 (en) 2022-11-28 2024-06-06 Hongene Biotech Corporation Functionalized n-acetylgalactosamine analogs
WO2024191807A1 (en) 2023-03-10 2024-09-19 Seagen Inc. Methods of treating cancer with anti-tigit antibodies
WO2025262564A1 (en) 2024-06-17 2025-12-26 Pfizer Inc. Use of anti-cxcr5 antibodies

Family Cites Families (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440780A (en) 1979-06-01 1984-04-03 Chevron Research Company Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones
JPH0660189B2 (ja) 1986-01-22 1994-08-10 財団法人微生物化学研究会 2,6−ジデオキシ−2−フルオロ−l−タロピラノ−ス又はその誘導体とその製造法
FR2630914A1 (fr) 1988-05-04 1989-11-10 Hoechst Sa Laboratoires Nouveaux analogues du l-fucose, leur procede de preparation, application de ces analogues a la preparation de nouveaux glycals, anthracyclines obtenues a l'aide de ces glycals et utilisation desdites anthracyclines en tant que medicaments
KR100211417B1 (ko) 1990-11-30 1999-10-01 유충식 L-탈로피라노시드 유도체 및 그의 제조방법
US5461143A (en) 1991-03-18 1995-10-24 The Scripps Research Institute Oligosaccharide enzyme substrates and inhibitors: methods and compositions
US5210078A (en) * 1991-04-30 1993-05-11 The Biomembrane Institute Trifluoromethyl analogs of fucose and uses thereof
EP0642526B1 (en) 1991-10-15 1998-12-23 The Scripps Research Institute Production of fucosylated carbohydrates by enzymatic fucosylation synthesis of sugar nucleotides; and in situ regeneration of gdp-fucose
ATE195127T1 (de) 1993-09-29 2000-08-15 Nissin Food Products Ltd In stellung 21 substituierte steroide
US5481143A (en) 1993-11-15 1996-01-02 Burdick; Brian K. Self starting brushless d.c. motor
FR2723947B1 (fr) 1994-08-31 1996-09-27 Adir Nouveaux composes tetrahydropyraniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
DE19524515A1 (de) 1995-07-05 1997-01-09 Deutsches Krebsforsch Saccharid-Konjugate
US6713287B1 (en) 1995-10-24 2004-03-30 The Scripps Research Institute Enzymatic synthesis of L-fucose and L-fucose analogs
AU5313798A (en) * 1996-10-28 1998-05-22 Novartis Ag Organic compounds
US5770407A (en) 1996-12-10 1998-06-23 The Scripps Research Institute Process for preparing nucleotide inhibitors of glycosyltransferases
JP4451933B2 (ja) * 1996-12-27 2010-04-14 住友化学株式会社 遺伝子操作による植物へのppo阻害性除草剤耐性付与法
US6075134A (en) 1997-05-15 2000-06-13 The Regents Of The University Of California Glycoconjugates and methods
JPH1135593A (ja) 1997-07-18 1999-02-09 Daikin Ind Ltd 2−フルオロフコシル−n−アロイルグルコサミン誘導体及びその中間物、並びにそれらの製造方法
US6670330B1 (en) 2000-05-01 2003-12-30 Theodore J. Lampidis Cancer chemotherapy with 2-deoxy-D-glucose
US7214660B2 (en) 2001-10-10 2007-05-08 Neose Technologies, Inc. Erythropoietin: remodeling and glycoconjugation of erythropoietin
US7265084B2 (en) 2001-10-10 2007-09-04 Neose Technologies, Inc. Glycopegylation methods and proteins/peptides produced by the methods
US20040132140A1 (en) 2002-04-09 2004-07-08 Kyowa Hakko Kogyo Co., Ltd. Production process for antibody composition
MXPA05007382A (es) 2003-01-10 2005-11-23 Threshold Pharmaceuticals Inc Tratamiento de cancer con 2-desoxiglucosa.
WO2004091499A2 (en) 2003-04-09 2004-10-28 Neose Technologies, Inc. Intracellular formation of peptide conjugates
EP2055189A1 (en) 2003-04-09 2009-05-06 Neose Technologies, Inc. Glycopegylation methods and proteins/peptides produced by the methods
US7332334B2 (en) 2003-04-18 2008-02-19 Oklahoma Medical Research Foundation Hematopoietic stem cells treated by in vitro fucosylation and methods of use
DE602004028249D1 (de) 2003-06-18 2010-09-02 Chugai Pharmaceutical Co Ltd Fucosetransporter
JPWO2005035741A1 (ja) 2003-10-09 2006-12-21 協和醗酵工業株式会社 ゲノムが改変された細胞
WO2005061523A1 (en) 2003-12-23 2005-07-07 Progen Industries Limited Glycosaminoglycan (gag) mimetics
DE102004032421A1 (de) 2004-07-05 2006-01-26 Bayer Cropscience Ag Phenylsubstituierte [1.2]-Oxazin-3,5-dion-und Dihydropyron-Derivate
US7393836B2 (en) 2004-07-06 2008-07-01 Boehringer Ingelheim International Gmbh D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
EP1829961A4 (en) 2004-12-22 2008-06-04 Chugai Pharmaceutical Co Ltd METHOD FOR THE PRODUCTION OF AN ANTIBODY USING A CELL WITH HARDENED FUCOSET TRANSPORT FUNCTION
CN101203241B (zh) 2005-04-19 2012-02-22 西雅图基因公司 人源化抗-cd70结合物和其应用
ATE536373T1 (de) 2005-10-21 2011-12-15 Genzyme Corp Therapiemittel auf antikörperbasis mit erhöhter adcc-aktivität
WO2007064448A2 (en) 2005-11-28 2007-06-07 Ramot At Tel Aviv University, Ltd. Cancer treatment using fts and 2-deoxyglucose
WO2007071051A1 (en) 2005-12-21 2007-06-28 Viventia Biotech Inc. Novel cancer-associated antigen
WO2007081031A1 (ja) 2006-01-16 2007-07-19 Hokkaido University 糖転移酵素阻害剤
EP2623986B1 (en) 2006-02-10 2017-06-14 Life Technologies Corporation Labeling and detection of post translationally modified proteins
AU2007220777A1 (en) 2006-02-24 2007-09-07 Board Of Regents, The University Of Texas System Hexose compounds to treat cancer
US8242167B2 (en) 2006-02-24 2012-08-14 University Of Miami Mannose derivatives for killing tumor cells
WO2007111952A2 (en) 2006-03-22 2007-10-04 The Scripps Research Institute Method of preparing glycopeptides
WO2009108926A1 (en) 2008-02-29 2009-09-03 Board Of Regents, The University Of Texas System Inhibitors of glycolysis useful in the treatment of brain tumors
US9149489B2 (en) 2006-04-27 2015-10-06 Board Of Regents, University Of Texas System Inhibitors of glycolysis useful in the treatment of brain tumors
CA2663536A1 (en) 2006-10-24 2008-05-02 Trubion Pharmaceuticals, Inc. Materials and methods for improved immunoglycoproteins
AU2008216794A1 (en) 2007-02-09 2008-08-21 Glycomimetics, Inc. Methods of use of glycomimetics with replacements for hexoses and N-acetyl hexosamines
WO2008131024A1 (en) 2007-04-17 2008-10-30 Board Of Regents, The University Of Texas System Iodo-hexose compounds useful to treat cancer
CN101062939A (zh) 2007-05-17 2007-10-31 北京热景生物技术有限公司 检测肝癌岩藻糖基化高尔基蛋白gp73的装置及试剂盒
RU2476441C2 (ru) 2007-10-19 2013-02-27 Сиэтл Дженетикс, Инк. Cd19-связывающие средства и их применение
US20110003338A1 (en) 2008-03-11 2011-01-06 Robert Bayer Antibodies with enhanced adcc function
US8163551B2 (en) 2008-05-02 2012-04-24 Seattle Genetics, Inc. Methods and compositions for making antibodies and antibody derivatives with reduced core fucosylation
WO2009143078A2 (en) 2008-05-19 2009-11-26 Board Of Regents, The University Of Texas System Methods of treating brain cancer using hexose compounds
EP2303282A4 (en) 2008-05-23 2013-02-13 Univ Miami TREATMENT WITH CONTINUOUS LOW DOSED APPLICATION OF SUGAR ANALOGUE
CN102065868A (zh) * 2008-06-16 2011-05-18 中央研究院 诱发对于Globo H及SSEA3的特异免疫反应的组合物以及其在癌症治疗中的用途
WO2010111713A2 (en) 2009-03-27 2010-09-30 Zacharon Pharmaceuticals, Inc. N-linked glycan biosynthesis modulators
EP2566876A4 (en) * 2010-05-06 2014-01-08 Univ Fraser Simon METHOD AND COMPOUNDS FOR INHIBITING GLYCOSYL TRANSFERASES
US20110288880A1 (en) 2010-05-07 2011-11-24 Patient Care Automation Services, Inc. Targeted health care messaging
DK2608796T3 (en) * 2010-08-05 2019-03-18 Seattle Genetics Inc Inhibition of protein fucosylation in vivo using fucose analogues
CA2824175A1 (en) 2011-01-11 2012-07-19 The University Of Texas M.D. Anderson Cancer Monosaccharide-based compounds for the treatment of proliferative and inflammatory dermatological diseases
US8979675B2 (en) 2012-04-25 2015-03-17 Nike, Inc. Golf ball core having radial appendages
WO2014031875A1 (en) 2012-08-23 2014-02-27 Seattle Genetics, Inc. Treatment of sickle cell disease and inflammatory conditions
WO2017096274A1 (en) 2015-12-04 2017-06-08 Seattle Genetics, Inc. Cancer treatment using 2-deoxy-2-fluoro-l-fucose in combination with a checkpoint inhibitor

Also Published As

Publication number Publication date
HUE043370T2 (hu) 2019-08-28
JP6113887B2 (ja) 2017-04-12
US9504702B2 (en) 2016-11-29
JP2017149723A (ja) 2017-08-31
JP2013541503A (ja) 2013-11-14
CN107007615A (zh) 2017-08-04
RU2017122482A3 (https=) 2019-01-30
EP2608796B1 (en) 2018-11-21
AU2011285490B2 (en) 2016-04-21
AU2017279653A1 (en) 2018-01-18
KR20190022884A (ko) 2019-03-06
RU2013109415A (ru) 2014-09-10
JP2020040974A (ja) 2020-03-19
EP2608796A2 (en) 2013-07-03
IL244019B (en) 2019-09-26
US10342811B2 (en) 2019-07-09
CN103402525B (zh) 2017-03-01
IL224487A (en) 2016-07-31
WO2012019165A3 (en) 2013-08-15
EP2608796A4 (en) 2014-06-11
AU2016204495A1 (en) 2016-07-21
EP3513794A3 (en) 2019-10-16
US20170035790A1 (en) 2017-02-09
KR101950520B1 (ko) 2019-02-20
EP3513794A2 (en) 2019-07-24
US20130129784A1 (en) 2013-05-23
RU2625768C2 (ru) 2017-07-18
CA2803388A1 (en) 2012-02-09
PT2608796T (pt) 2019-02-25
US20200061091A1 (en) 2020-02-27
JP2016175909A (ja) 2016-10-06
AU2011285490A1 (en) 2013-01-10
CY1121419T1 (el) 2020-05-29
US20210260086A1 (en) 2021-08-26
TR201902439T4 (tr) 2019-03-21
ES2711622T3 (es) 2019-05-06
PL2608796T3 (pl) 2019-04-30
KR20130135240A (ko) 2013-12-10
RU2017122482A (ru) 2019-01-30
ZA201300653B (en) 2014-03-26
SI2608796T1 (sl) 2019-03-29
WO2012019165A2 (en) 2012-02-09
IL244019A0 (en) 2016-04-21
JP5918235B2 (ja) 2016-05-18
US11033561B2 (en) 2021-06-15
NZ606250A (en) 2015-04-24
MX356671B (es) 2018-06-08
MX2013001303A (es) 2014-07-24
JP6622238B2 (ja) 2019-12-18
CN103402525A (zh) 2013-11-20
DK2608796T3 (en) 2019-03-18

Similar Documents

Publication Publication Date Title
CA2803388C (en) Methods of inhibition of protein fucosylation in vivo using fucose analogs
KR101755526B1 (ko) 알파-갈락토실 세라미드 유사체, 및 면역요법제, 아주반트, 및 항바이러스제, 항박테리아제, 및 항암제로서의 그의 용도
KR20250024743A (ko) Trop-2를 발현하는 종양을 표적화하기 위한 항체-컨쥬게이트
WO2022235817A1 (en) Combination therapies comprising shp2 inhibitors and pd-1 inhibitors
HK40011525A (en) Fucose analogs for inhibition of protein fucosylation in vivo
HK1186659A (en) Inhibition of protein fucosylation in vivo using fucose analogs
HK1186659B (en) Inhibition of protein fucosylation in vivo using fucose analogs
US20230331649A1 (en) Inhibitors of protein fucosylation and uses thereof
CN117651566A (zh) 用于癌的治疗和/或预防的药品

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20160426

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 13TH ANNIV.) - STANDARD

Year of fee payment: 13

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20240724

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20240726

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251223

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20260407