CA2429781C - Linkable sialyl lewis x analogs - Google Patents
Linkable sialyl lewis x analogs Download PDFInfo
- Publication number
- CA2429781C CA2429781C CA2429781A CA2429781A CA2429781C CA 2429781 C CA2429781 C CA 2429781C CA 2429781 A CA2429781 A CA 2429781A CA 2429781 A CA2429781 A CA 2429781A CA 2429781 C CA2429781 C CA 2429781C
- Authority
- CA
- Canada
- Prior art keywords
- conjugate
- compound
- benzyl
- hydrogen
- acetamido
- 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.)
- Expired - Lifetime
Links
- NIGUVXFURDGQKZ-UQTBNESHSA-N alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc Chemical class O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@]3(O[C@H]([C@H](NC(C)=O)[C@@H](O)C3)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O NIGUVXFURDGQKZ-UQTBNESHSA-N 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
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- 230000027455 binding Effects 0.000 claims abstract description 36
- 239000003446 ligand Substances 0.000 claims abstract description 36
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229940127089 cytotoxic agent Drugs 0.000 claims abstract description 15
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
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- 125000005630 sialyl group Chemical group 0.000 claims description 32
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- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims description 9
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- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 6
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- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 3
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- 230000005951 type IV hypersensitivity Effects 0.000 description 1
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- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
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- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
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- 229960003165 vancomycin Drugs 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25023800P | 2000-11-29 | 2000-11-29 | |
| US60/250,238 | 2000-11-29 | ||
| PCT/US2001/044590 WO2002062810A2 (en) | 2000-11-29 | 2001-11-29 | Linkable sialyl lewis x analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2429781A1 CA2429781A1 (en) | 2002-08-15 |
| CA2429781C true CA2429781C (en) | 2011-01-11 |
Family
ID=22946912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2429781A Expired - Lifetime CA2429781C (en) | 2000-11-29 | 2001-11-29 | Linkable sialyl lewis x analogs |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US7422733B2 (enExample) |
| EP (1) | EP1337539A2 (enExample) |
| JP (1) | JP4262480B2 (enExample) |
| AU (1) | AU2002251678A1 (enExample) |
| CA (1) | CA2429781C (enExample) |
| WO (1) | WO2002062810A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5183010B2 (ja) | 2002-05-16 | 2013-04-17 | グリコミメティクス， インコーポレイテッド | セレクチンによって媒介される機能を阻害するための化合物および方法 |
| DE602004011272T2 (de) | 2003-11-19 | 2008-12-24 | Glycomimetics, Inc. | Spezifischer antagonist sowohl für e- als auch p-selektine |
| US7205385B2 (en) * | 2004-11-12 | 2007-04-17 | General Electric Company | Polymerization method for the synthesis of polypeptide imaging agents |
| DK1928892T3 (da) | 2005-08-09 | 2012-01-30 | Glycomimetics Inc | Glycomimetiske inhibitorer af PA-IL-lectin PA-IIL-lectin eller begge lectiner fra pseudomonas |
| GB0517077D0 (en) * | 2005-08-19 | 2005-09-28 | Isis Innovation | Imaging agent |
| PL1934236T3 (pl) | 2005-09-02 | 2013-04-30 | Glycomimetics Inc | Heterobifunkcjonalne inhibitory pan-selektyny |
| US8986650B2 (en) | 2005-10-07 | 2015-03-24 | Guerbet | Complex folate-NOTA-Ga68 |
| WO2007042504A2 (fr) | 2005-10-07 | 2007-04-19 | Guerbet | Composes comprenant une partie de reconnaissance d'une cible biologique, couplee a une partie de signal capable de complexer le gallium |
| US8895510B2 (en) | 2008-04-08 | 2014-11-25 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
| FR2942227B1 (fr) | 2009-02-13 | 2011-04-15 | Guerbet Sa | Utilisation de tampons pour la complexation de radionucleides |
| CA2760292A1 (en) * | 2009-05-01 | 2010-11-04 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors |
| 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 |
| WO2012060718A1 (en) * | 2010-11-05 | 2012-05-10 | Sally Diana Poppitt | Preventing or treating metabolic syndrome by administering a trans fatty acid, or a salt, ester or precursor thereof, or sialic acid in free or bound form |
| FR2968999B1 (fr) | 2010-12-20 | 2013-01-04 | Guerbet Sa | Nanoemulsion de chelate pour irm |
| FR2980364B1 (fr) | 2011-09-26 | 2018-08-31 | Guerbet | Nanoemulsions et leur utilisation comme agents de contraste |
| WO2013096926A1 (en) | 2011-12-22 | 2013-06-27 | Glycomimetics, Inc. | E-selectin antagonist compounds, compositions, 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 |
| FR3001154B1 (fr) | 2013-01-23 | 2015-06-26 | Guerbet Sa | Magneto-emulsion vectorisee |
| JP2016539172A (ja) * | 2013-12-06 | 2016-12-15 | ザ ロイヤル インスティチューション フォー ザ アドバンスメント オブ ラーニング／マギル ユニバーシティ | 癌標的化及び抗体作製のための抗ガングリオシド化合物 |
| WO2016089872A1 (en) | 2014-12-03 | 2016-06-09 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors |
| EP3170832A1 (en) * | 2015-11-17 | 2017-05-24 | Centre National De La Recherche Scientifique | Method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-d-mannose |
| US11045485B2 (en) | 2016-01-22 | 2021-06-29 | Glycomimetics, Inc. | Glycomimetic inhibitors of PA-IL and PA-IIL lectins |
| 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 |
| 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 |
| US11072625B2 (en) | 2016-10-07 | 2021-07-27 | Glycomimetics, Inc. | Highly potent multimeric e-selectin antagonists |
| WO2018112669A1 (en) | 2016-12-23 | 2018-06-28 | Realist Pharma, Inc. | Ganglioside carbohydrate structures and uses thereof |
| CA3054605A1 (en) | 2017-03-15 | 2018-09-20 | Glycomimetics, Inc. | Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists |
| US11712446B2 (en) | 2017-11-30 | 2023-08-01 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| BR112020013198A2 (pt) | 2017-12-29 | 2020-12-01 | Glycomimetics, Inc. | inibidores heterobifuncionais de e-selectina e galectina-3 |
| KR20200128025A (ko) | 2018-03-05 | 2020-11-11 | 글리코미메틱스, 인크. | 급성 골수성 백혈병 및 관련 병태의 치료 방법 |
| WO2020007822A1 (en) | 2018-07-02 | 2020-01-09 | Conservatoire National Des Arts Et Metiers (Cnam) | Bismuth metallic (0) nanoparticles, process of manufacturing and uses thereof |
| WO2020139962A1 (en) | 2018-12-27 | 2020-07-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectin and galectin-3 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1260393A (en) * | 1984-10-16 | 1989-09-26 | Lajos Tarcsay | Liposomes of synthetic lipids |
| US5776093A (en) * | 1985-07-05 | 1998-07-07 | Immunomedics, Inc. | Method for imaging and treating organs and tissues |
| MX174467B (es) * | 1986-01-23 | 1994-05-17 | Squibb & Sons Inc | 1,4,7-triscarboximetil-1,4,7,10-tetraazaciclodo decano substituido en 1 y compuestos analogos |
| JPH06510745A (ja) | 1991-06-10 | 1994-12-01 | グライカムド インコーポレイテッド | 修飾シアリルルイスａ化合物 |
| CA2110797C (en) | 1991-06-10 | 2001-02-20 | Andre P. Venot | Modified sialyl lewis x compounds |
| GB9309513D0 (en) | 1993-05-08 | 1993-06-23 | Univ Coventry | Electrochemical method of modifying biomolecules in particular proteins |
| CA2162478A1 (en) * | 1993-05-14 | 1994-11-24 | Shawn A. Defrees | Sialyl lex analogues as inhibitors of cellular adhesion |
| US5608110A (en) * | 1993-06-15 | 1997-03-04 | Bracco International B.V. | Heteroatom-bearing ligands and metal complexes thereof |
| US5662885A (en) * | 1994-07-22 | 1997-09-02 | Resolution Pharmaceuticals Inc. | Peptide derived radionuclide chelators |
| US6132764A (en) * | 1994-08-05 | 2000-10-17 | Targesome, Inc. | Targeted polymerized liposome diagnostic and treatment agents |
| US6331289B1 (en) * | 1996-10-28 | 2001-12-18 | Nycomed Imaging As | Targeted diagnostic/therapeutic agents having more than one different vectors |
-
2001
- 2001-11-29 AU AU2002251678A patent/AU2002251678A1/en not_active Abandoned
- 2001-11-29 WO PCT/US2001/044590 patent/WO2002062810A2/en not_active Ceased
- 2001-11-29 US US10/432,914 patent/US7422733B2/en not_active Expired - Lifetime
- 2001-11-29 JP JP2002563162A patent/JP4262480B2/ja not_active Expired - Lifetime
- 2001-11-29 EP EP01999154A patent/EP1337539A2/en not_active Withdrawn
- 2001-11-29 CA CA2429781A patent/CA2429781C/en not_active Expired - Lifetime
-
2008
- 2008-08-13 US US12/190,857 patent/US20080300220A1/en not_active Abandoned
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2011
- 2011-05-26 US US13/116,828 patent/US20110229409A1/en not_active Abandoned
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2012
- 2012-04-26 US US13/456,747 patent/US20120258043A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20080300220A1 (en) | 2008-12-04 |
| CA2429781A1 (en) | 2002-08-15 |
| WO2002062810A2 (en) | 2002-08-15 |
| JP4262480B2 (ja) | 2009-05-13 |
| US20040097403A1 (en) | 2004-05-20 |
| EP1337539A2 (en) | 2003-08-27 |
| US20120258043A1 (en) | 2012-10-11 |
| US20110229409A1 (en) | 2011-09-22 |
| US7422733B2 (en) | 2008-09-09 |
| AU2002251678A1 (en) | 2002-08-19 |
| WO2002062810A3 (en) | 2003-02-13 |
| JP2004518704A (ja) | 2004-06-24 |
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