WO2003000709A2 - Sialinsäure-derivate als siglec-inhibitoren - Google Patents
Sialinsäure-derivate als siglec-inhibitoren Download PDFInfo
- Publication number
- WO2003000709A2 WO2003000709A2 PCT/EP2002/006277 EP0206277W WO03000709A2 WO 2003000709 A2 WO2003000709 A2 WO 2003000709A2 EP 0206277 W EP0206277 W EP 0206277W WO 03000709 A2 WO03000709 A2 WO 03000709A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- siglec
- inhibitor according
- atom
- derivative
- Prior art date
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008614 cellular interaction Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- RGBVWCQARBEPPW-UHFFFAOYSA-N cyclobut-3-ene-1,2-dione Chemical compound O=C1C=CC1=O RGBVWCQARBEPPW-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000000222 eosinocyte Anatomy 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 150000008273 hexosamines Chemical class 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 108091008042 inhibitory receptors Proteins 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000008611 intercellular interaction Effects 0.000 description 1
- 230000000503 lectinlike effect Effects 0.000 description 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
- 229940039781 leptin Drugs 0.000 description 1
- 108020001756 ligand binding domains Proteins 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 210000003643 myeloid progenitor cell Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 230000003448 neutrophilic effect Effects 0.000 description 1
- 210000004248 oligodendroglia Anatomy 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000021930 regulation of neuron projection development Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000005629 sialic acid group Chemical group 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- QULKDBMYSOOKMH-UHFFFAOYSA-N sulfo hydrogen carbonate Chemical compound OC(=O)OS(O)(=O)=O QULKDBMYSOOKMH-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 210000002993 trophoblast Anatomy 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
Classifications
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- 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
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
- C07H7/027—Keto-aldonic acids
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/481,529 US7820714B2 (en) | 2001-06-19 | 2002-06-07 | Siglec inhibitors |
KR10-2003-7016631A KR20040040408A (ko) | 2001-06-19 | 2002-06-07 | 시글렉 억제제 |
EP02748751A EP1397374A2 (de) | 2001-06-19 | 2002-06-07 | Siglec-inhibitoren |
JP2003507112A JP2004534085A (ja) | 2001-06-19 | 2002-06-07 | シグレック阻害剤 |
CA2451051A CA2451051C (en) | 2001-06-19 | 2002-06-07 | Siglec inhibitors |
AU2002319207A AU2002319207B2 (en) | 2001-06-19 | 2002-06-07 | Sialic acid derivatives for use as siglec inhibitors |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10129332.1 | 2001-06-19 | ||
DE2001129332 DE10129332A1 (de) | 2001-06-19 | 2001-06-19 | Sialinsäure-Derivate als Siglec-Inhibitoren |
DE10216310 | 2002-04-12 | ||
DE10216310.3 | 2002-04-12 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2003000709A2 true WO2003000709A2 (de) | 2003-01-03 |
WO2003000709A9 WO2003000709A9 (de) | 2003-04-10 |
WO2003000709A3 WO2003000709A3 (de) | 2003-09-25 |
Family
ID=26009544
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/006277 WO2003000709A2 (de) | 2001-06-19 | 2002-06-07 | Sialinsäure-derivate als siglec-inhibitoren |
Country Status (8)
Country | Link |
---|---|
US (1) | US7820714B2 (de) |
EP (1) | EP1397374A2 (de) |
JP (1) | JP2004534085A (de) |
KR (1) | KR20040040408A (de) |
CN (1) | CN100491389C (de) |
AU (1) | AU2002319207B2 (de) |
CA (1) | CA2451051C (de) |
WO (1) | WO2003000709A2 (de) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007105094A1 (en) * | 2006-03-14 | 2007-09-20 | Universität Basel | Method for the identification of new leads for drug candidates |
WO2009036754A1 (de) * | 2007-09-21 | 2009-03-26 | Universität Hamburg | Inhibitoren des myelin assoziierten glykoproteins (mag) |
EP2610263A1 (de) | 2011-12-30 | 2013-07-03 | Brossmer, Reinhard | Sialinsäure-Dimere |
WO2013190103A1 (de) * | 2012-06-21 | 2013-12-27 | Reinhard Brossmer | Sialinsäurederivate |
EP2910561A1 (de) | 2014-02-25 | 2015-08-26 | Reinhard Brossmer | Sialinsäurederivate |
US10973922B2 (en) | 2013-05-02 | 2021-04-13 | Glykos Finland Oy | Glycoprotein-toxic payload conjugates |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20060058830A (ko) | 2004-11-26 | 2006-06-01 | 한국표준과학연구원 | 개별시료 주입구가 없는 다중채널 전기영동장치에 의한분리방법 |
WO2007120815A2 (en) * | 2006-04-12 | 2007-10-25 | The Regents Of The University Of California | Methods for treating lymphocyte-associated disorders by modulation of siglec activity |
US9018245B2 (en) | 2006-12-26 | 2015-04-28 | Japan Science And Technology | Method for promoting immune response comprising inhibiting CD22 function in B cells |
EP2625205A2 (de) * | 2010-10-05 | 2013-08-14 | Daiichi Sankyo Company, Limited | Auf das osteoklastenabhängige protein siglec-15 gerichteter antikörper |
WO2014098249A1 (ja) * | 2012-12-21 | 2014-06-26 | 国立大学法人名古屋大学 | 組織修復活性組成物及びその利用 |
CA2918194C (en) * | 2013-03-27 | 2022-12-06 | The General Hospital Corporation | Methods and agents for treating alzheimer's disease |
ES2785551T3 (es) | 2014-06-30 | 2020-10-07 | Glykos Finland Oy | Derivado de sacárido de una carga útil tóxica y sus conjugados con anticuerpos |
CN105017340B (zh) * | 2015-08-05 | 2017-11-14 | 厦门大学 | 一种抗原连接的唾液酸及其应用 |
EP3368575A2 (de) * | 2015-10-29 | 2018-09-05 | Alector LLC | Anti-siglec-9-antikörper und verfahren zur verwendung davon |
EP3481374A1 (de) | 2016-07-08 | 2019-05-15 | The Scripps Research Institute | Desensibilisierung von mastzellen durch co-präsentation von antigenen mit hochaffinen mastzellen-siglec-liganden |
WO2018098342A1 (en) * | 2016-11-23 | 2018-05-31 | The Regents Of The University Of California | N-acetylated sialic acids and related sialosides |
CN107501291B (zh) * | 2017-10-14 | 2020-01-21 | 厦门诺康得生物科技有限公司 | 一种cd169高亲和力抗肿瘤化合物及其制备方法和应用 |
CN108047282B (zh) * | 2017-12-19 | 2020-06-09 | 厦门诺康得生物科技有限公司 | 一种唾液酸衍生物及其制备方法和应用 |
CN108676044B (zh) * | 2018-05-16 | 2021-03-30 | 厦门诺康得生物科技有限公司 | 一种cd33亲和的唾液酸衍生物及其应用 |
CN108728412B (zh) * | 2018-06-08 | 2021-11-09 | 厦门诺康得生物科技有限公司 | 一种nk细胞表面修改的免疫检查点抑制剂及其应用 |
CN108743595B (zh) * | 2018-06-08 | 2020-11-27 | 厦门诺康得生物科技有限公司 | 一种nk细胞免疫检查点抑制剂及其制备方法 |
CN111973608B (zh) * | 2020-09-17 | 2023-05-23 | 准邑科技(厦门)有限公司 | 一种唾液酸衍生物的用途 |
CN116003486B (zh) * | 2023-03-27 | 2023-08-01 | 北京天之泰生物科技有限公司 | 一种先导化合物、其制备方法、以及其在制备抗流感病毒药物方面的应用 |
Citations (1)
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WO1992022301A1 (en) * | 1991-06-10 | 1992-12-23 | Alberta Research Council | Immunosuppressive and tolerogenic oligosaccharide derivatives |
-
2002
- 2002-06-07 US US10/481,529 patent/US7820714B2/en not_active Expired - Fee Related
- 2002-06-07 WO PCT/EP2002/006277 patent/WO2003000709A2/de active IP Right Grant
- 2002-06-07 JP JP2003507112A patent/JP2004534085A/ja active Pending
- 2002-06-07 AU AU2002319207A patent/AU2002319207B2/en not_active Ceased
- 2002-06-07 CN CNB028121708A patent/CN100491389C/zh not_active Expired - Fee Related
- 2002-06-07 KR KR10-2003-7016631A patent/KR20040040408A/ko active Search and Examination
- 2002-06-07 EP EP02748751A patent/EP1397374A2/de not_active Withdrawn
- 2002-06-07 CA CA2451051A patent/CA2451051C/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992022301A1 (en) * | 1991-06-10 | 1992-12-23 | Alberta Research Council | Immunosuppressive and tolerogenic oligosaccharide derivatives |
Non-Patent Citations (5)
Title |
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KELM S ET AL: "FUNCTIONAL GROUPS OF SIALIC ACIDS INVOLVED IN BINDING TO SIGLECS (SIALOADHESINS) DEDUCED FROM INTERACTIONS WITH SYNTHETIC ANALOGUES" EUROPEAN JOURNAL OF BIOCHEMISTRY, BERLIN, DE, Bd. 255, Nr. 3, 1998, Seiten 663-672, XP000913907 ISSN: 0014-2956 * |
M. FERNANDA TRONCOSO ET AL.: "Specifity of the binding site of the sialic acid-binding lectin from ovine placenta, deduced from interactions with Synthetic analogues" GLYCOCONJUGATE JOURNAL, Bd. 17, 2000, Seiten 705-711, XP008008959 * |
MIRELIS P ET AL: "Photoreactive CMP-sialic acids as substrates for alpha2,6-sialyltransferase" BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, Bd. 5, Nr. 23, 7. Dezember 1995 (1995-12-07), Seiten 2809-2814, XP004135172 ISSN: 0960-894X * |
NORTON A K ET AL: "THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE ALPHA-METHYL GLYCOSIDE OF KDN METHYL ESTER" JOURNAL OF CARBOHYDRATE CHEMISTRY, NEW YORK, NY, US, Bd. 20, Nr. 2, 2001, Seiten 227-238, XP008008970 ISSN: 0732-8303 * |
S. KELM ET AL.: "The ligand-binding domain of CD22 is needed for inhibition of the B cell receptor signal, as demonstrated by a novel human CD22-specific inhibitor compound" J. EXP. MED., Bd. 195, 2002, Seiten 1207-1213, XP002227045 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007105094A1 (en) * | 2006-03-14 | 2007-09-20 | Universität Basel | Method for the identification of new leads for drug candidates |
WO2009036754A1 (de) * | 2007-09-21 | 2009-03-26 | Universität Hamburg | Inhibitoren des myelin assoziierten glykoproteins (mag) |
EP2610263A1 (de) | 2011-12-30 | 2013-07-03 | Brossmer, Reinhard | Sialinsäure-Dimere |
WO2013097942A1 (de) | 2011-12-30 | 2013-07-04 | Reinhard Brossmer | Sialinsäure-dimere |
WO2013190103A1 (de) * | 2012-06-21 | 2013-12-27 | Reinhard Brossmer | Sialinsäurederivate |
US9539336B2 (en) | 2012-06-21 | 2017-01-10 | Reinhard Brossmer | Sialic acid derivatives |
US10973922B2 (en) | 2013-05-02 | 2021-04-13 | Glykos Finland Oy | Glycoprotein-toxic payload conjugates |
EP2910561A1 (de) | 2014-02-25 | 2015-08-26 | Reinhard Brossmer | Sialinsäurederivate |
US10472381B2 (en) | 2014-02-25 | 2019-11-12 | Reinhard Brossmer | Sialic acid derivatives |
Also Published As
Publication number | Publication date |
---|---|
KR20040040408A (ko) | 2004-05-12 |
CN100491389C (zh) | 2009-05-27 |
US20040176309A1 (en) | 2004-09-09 |
WO2003000709A3 (de) | 2003-09-25 |
EP1397374A2 (de) | 2004-03-17 |
AU2002319207B2 (en) | 2007-03-01 |
WO2003000709A9 (de) | 2003-04-10 |
CA2451051A1 (en) | 2003-01-03 |
CA2451051C (en) | 2012-11-27 |
US7820714B2 (en) | 2010-10-26 |
CN1656113A (zh) | 2005-08-17 |
JP2004534085A (ja) | 2004-11-11 |
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