WO1991018911A3 - Oxazolines oligosaccharidiques, conjuges oligosaccharidiques, et leurs procedes de preparation - Google Patents

Oxazolines oligosaccharidiques, conjuges oligosaccharidiques, et leurs procedes de preparation Download PDF

Info

Publication number
WO1991018911A3
WO1991018911A3 PCT/US1991/003687 US9103687W WO9118911A3 WO 1991018911 A3 WO1991018911 A3 WO 1991018911A3 US 9103687 W US9103687 W US 9103687W WO 9118911 A3 WO9118911 A3 WO 9118911A3
Authority
WO
WIPO (PCT)
Prior art keywords
oligosaccharide
peracetyl
conjugate
spacer
conjugates
Prior art date
Application number
PCT/US1991/003687
Other languages
English (en)
Other versions
WO1991018911A2 (fr
Inventor
Marcelo Colon
Jeffrey T Davis
James R Rasmussen
Marianne Borowski
Barbara Y Wan
Shirish Hirani
Original Assignee
Genzyme Corp
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 Genzyme Corp filed Critical Genzyme Corp
Priority to DE69130221T priority Critical patent/DE69130221T2/de
Priority to CA002081665A priority patent/CA2081665C/fr
Priority to EP91911062A priority patent/EP0535052B1/fr
Publication of WO1991018911A2 publication Critical patent/WO1991018911A2/fr
Publication of WO1991018911A3 publication Critical patent/WO1991018911A3/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/06Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • 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
    • C07H15/02Acyclic radicals, not substituted by cyclic structures
    • C07H15/04Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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
    • C07H15/02Acyclic radicals, not substituted by cyclic structures
    • C07H15/12Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical

Abstract

Procédé de préparation de peracétyloxazolines à partir de saccharides de peracétyle. Le procédé consiste à faire réagir le matériau de départ, un saccharide de peracétyle, avec une combinaison de réactifs pour directement produire l'oxazoline de peracétyle. Ce procédé peut servir à activer les oligosaccharides, un oligosaccharide contenant un GlcNAc réducteur en fin de chaîne étant activé par la formation d'une oxazoline au niveau de cette fin de chaîne, puis couplé à un spacer bifonctionnnel pour donner un conjugué oligosaccharide/spacer. Ensuite, on couple ce conjugué à une protéine, telle que le facteur stimulateur des colonies de granulocytes ou l'interféron-η, pour donner un conjugué néoglycoprotéique. On a prévu un procédé de formation de conjugués néoglycoprotéiques aptes a améliorer les caractéristiques biologiques et physiochimiques de la protéine. Par example, on peut améliorer la durée de vie de sérum ou l'efficacité de l'administration du peptide à un organe cible ou à une cellule cible.
PCT/US1991/003687 1990-05-25 1991-05-24 Oxazolines oligosaccharidiques, conjuges oligosaccharidiques, et leurs procedes de preparation WO1991018911A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE69130221T DE69130221T2 (de) 1990-05-25 1991-05-24 Oligosaccharidoxazolines, konjugate von oligosacchariden und verfahren zu ihrer herstellung
CA002081665A CA2081665C (fr) 1990-05-25 1991-05-24 Oxazolines d'oligosaccharide, produits conjugues d'oligosaccharide et leurs methodes de preparation
EP91911062A EP0535052B1 (fr) 1990-05-25 1991-05-24 Oxazolines oligosaccharidiques, conjuges oligosaccharidiques, et leurs procedes de preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US529,343 1990-05-25
US07/529,343 US5241072A (en) 1990-05-25 1990-05-25 Oligosaccharide oxazolines, oligosaccharide conjugates and methods of preparation thereof

Publications (2)

Publication Number Publication Date
WO1991018911A2 WO1991018911A2 (fr) 1991-12-12
WO1991018911A3 true WO1991018911A3 (fr) 1992-05-14

Family

ID=24109524

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/003687 WO1991018911A2 (fr) 1990-05-25 1991-05-24 Oxazolines oligosaccharidiques, conjuges oligosaccharidiques, et leurs procedes de preparation

Country Status (6)

Country Link
US (2) US5241072A (fr)
EP (2) EP0860442B1 (fr)
JP (1) JP3217059B2 (fr)
CA (1) CA2081665C (fr)
DE (3) DE860442T1 (fr)
WO (1) WO1991018911A2 (fr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5718893A (en) * 1984-04-15 1998-02-17 Foster; Preston F. Use of G-CSF to reduce acute rejection
JP2794678B2 (ja) 1991-08-26 1998-09-10 株式会社 半導体エネルギー研究所 絶縁ゲイト型半導体装置およびその作製方法
US5485019A (en) 1992-02-05 1996-01-16 Semiconductor Energy Laboratory Co., Ltd. Semiconductor device and method for forming the same
DE4204315A1 (de) * 1992-02-13 1993-08-19 Consortium Elektrochem Ind Cyclodextringlycoside und verfahren zu ihrer herstellung
US6624450B1 (en) 1992-03-27 2003-09-23 Semiconductor Energy Laboratory Co., Ltd. Semiconductor device and method for forming the same
FR2693907B1 (fr) * 1992-07-23 1994-09-02 Rhone Poulenc Rorer Sa Procédé d'administration de solutions de facteur de stimulation des colonies granulocytaires.
EP0601417A3 (fr) * 1992-12-11 1998-07-01 Hoechst Aktiengesellschaft Physiologiquement compatible et dégradable bloques de récepteur d'hydrate de carbone à base de polymère, procédé de leur préparation et leur utilisation
US5536495A (en) * 1994-04-15 1996-07-16 Foster; Preston F. Use of G-CSF to reduce acute rejection
CZ20021836A3 (cs) * 1999-11-12 2002-08-14 Maxygen Holdings Ltd Konjugáty interferonu gama
AU782635B2 (en) * 1999-11-12 2005-08-18 Maxygen Holdings Ltd. Interferon gamma conjugates
YU32402A (sh) 1999-11-12 2005-03-15 Maxygen Holdings Ltd. Konjugati gama interferona
US7186425B2 (en) * 2000-09-29 2007-03-06 Fuji Oil Company, Ltd. Composition for diminishing neutral fat in blood
WO2002066496A1 (fr) * 2001-02-20 2002-08-29 Takara Bio Inc. Modificateur
US6958388B2 (en) 2001-04-06 2005-10-25 Maxygen, Aps Interferon gamma polypeptide variants
US7038015B2 (en) 2001-04-06 2006-05-02 Maxygen Holdings, Ltd. Interferon gamma polypeptide variants
WO2003016883A1 (fr) 2001-08-16 2003-02-27 Analiza, Inc. Procede de mesure de la solubilite
US7968350B2 (en) * 2001-11-12 2011-06-28 Analiza, Inc. Characterization of molecules
US7299805B2 (en) * 2002-06-07 2007-11-27 Marctec, Llc Scaffold and method for implanting cells
CA2491178A1 (fr) 2002-07-03 2004-01-15 Maxygen Holdings Ltd. Variants polypeptidiques a interferon gamma pleine longueur
US8099242B2 (en) * 2003-06-12 2012-01-17 Analiza, Inc. Systems and methods for characterization of molecules
US7220407B2 (en) 2003-10-27 2007-05-22 Amgen Inc. G-CSF therapy as an adjunct to reperfusion therapy in the treatment of acute myocardial infarction
AU2005306894B2 (en) 2004-11-05 2011-11-24 Northwestern University Use of SCF and G-CSF in the treatment of cerebral ischemia and neurological disorders
EP1977254B1 (fr) 2005-12-19 2012-02-08 Analiza, Inc. Procédés faisant intervenir des configurations de données du type biomarqueurs spectraux
WO2014025961A1 (fr) 2012-08-10 2014-02-13 Analiza, Inc. Procédés et dispositifs d'analyse d'espèces pour déterminer des maladies
US9678076B2 (en) 2014-06-24 2017-06-13 Analiza, Inc. Methods and devices for determining a disease state
ES2793023T3 (es) * 2014-08-08 2020-11-12 Glaxosmithkline Biologicals Sa Células huésped modificadas y oligosacáridos híbridos para su uso en producción de bioconjugados
JP2022129250A (ja) * 2021-02-24 2022-09-05 学校法人 中央大学 ポリオキサゾリン結合アルブミン、人工血漿増量剤及び出血ショックの蘇生液
WO2023076036A1 (fr) 2021-10-28 2023-05-04 Analiza, Inc. Systèmes et procédés de partitionnement pour déterminer de multiples types de cancers

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098252A2 (fr) * 1982-06-23 1984-01-11 Biocarb Ab Glycosides, glycoconjugates et leur procédé de préparation
WO1988004323A1 (fr) * 1986-12-11 1988-06-16 Genzyme Corporation Preparation de 1-amino-1-desoxyoligosaccharides et de leurs derives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ214503A (en) * 1984-12-20 1990-02-26 Merck & Co Inc Covalently-modified neutral bacterial polysaccharides, stable covalent conjugates of such polysaccharides and immunogenic proteins, and methods of preparing such polysaccharides and conjugates
DK17685D0 (da) * 1985-01-14 1985-01-14 Hans Goeran Magnusson Glycosidderivater
DE3505150A1 (de) * 1985-02-15 1986-08-21 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von zuckerketalen
US4785084A (en) * 1986-07-31 1988-11-15 The General Hospital Corporation Method of preparing peracetyl oxazolines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098252A2 (fr) * 1982-06-23 1984-01-11 Biocarb Ab Glycosides, glycoconjugates et leur procédé de préparation
WO1988004323A1 (fr) * 1986-12-11 1988-06-16 Genzyme Corporation Preparation de 1-amino-1-desoxyoligosaccharides et de leurs derives

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Angewandte Chemie, International Edition in English, vol. 29, no. 9, September 1990, (Weinheim, DE), W. GÜNTHER et al.: "Synthesis of a beta-mannosyl-chitobiosyl-asparagine conjugate - A central core region unit of the N-glycoproteins", pages 1050-1051, see the whole document *
Carbohydrate Research, vol. 124, 1983, (Amsterdam, NL), B. MARIO PINTO et al.: "Preparation of glycoconjugates for use as artifical antigens: A simplified procedure", pages 313-318, see scheme 1; table 1 *
Carbohydrate Research, vol. 174, 1988, (Amsterdam, NL), S. NAKABAYASHI et al.: "The preparation of a partially protected heptasaccharide-asparagine intermediate for glycopeptide synthesis", pages 279-289, see the whole document *
Journal of Organic Chemistry, vol. 55, no. 12, 8 June 1990, (Easton, US), G. MAGNUSSON et al.: "Prespacer glycosides in glycoconjugate chemistry. Dibromoisobutyl glycosides for the synthesis of neoglycolipids, neoglycoproteins, neoglycoparticles, and soluble glycosides", pages 3932-3946, see scheme 1; chart 1; scheme II *
Journal of the American Chemical Society, vol. 97, no. 14, 9 July 1975, (Washington, DC, US), R. LEMIEUX et al.: "The properties of a "synthetic" antigen related to the human blood group lewis A", pages 4076-4083, see page 4077 *

Also Published As

Publication number Publication date
CA2081665C (fr) 2002-01-01
DE860442T1 (de) 1999-04-22
JPH05507487A (ja) 1993-10-28
EP0860442A1 (fr) 1998-08-26
US5241072A (en) 1993-08-31
EP0535052A1 (fr) 1993-04-07
DE69132586D1 (de) 2001-05-23
EP0860442B1 (fr) 2001-04-18
CA2081665A1 (fr) 1991-11-26
DE69132586T2 (de) 2002-04-11
DE69130221D1 (de) 1998-10-22
DE69130221T2 (de) 1999-01-21
EP0535052B1 (fr) 1998-09-16
US5659015A (en) 1997-08-19
WO1991018911A2 (fr) 1991-12-12
JP3217059B2 (ja) 2001-10-09

Similar Documents

Publication Publication Date Title
WO1991018911A3 (fr) Oxazolines oligosaccharidiques, conjuges oligosaccharidiques, et leurs procedes de preparation
Osborn et al. Recent developments in polymer supported syntheses of oligosaccharides and glycopeptides
Davis Synthesis of glycoproteins
CA2015060A1 (fr) Systeme de liberation d'anticorps pour modifier la reponse biologique
US5599914A (en) Glycosphingolipids with a group capable of coupling in the sphingoid portion, the preparation and use thereof
EP0044188B1 (fr) Synthèse de déterminants antigéniques tumoraux
EP0319253A3 (fr) Glycosides de l'acide sialique, antigènes, immunoadsorbants et procédé de leur préparation
JPH06509703A (ja) α−シアリル化オリゴサッカロイドグリコシドの酵素的合成方法
JPH05222099A (ja) 合成n−結合グリコ複合体の製造法
Roy et al. N-Acetylneuraminic acid: Neoglycoproteins and pseudopolysaccharides
US5668272A (en) Method for producing synthetic N-linked glycoconjugates
Wei et al. Novel reversible fluorescent glycan linker for functional glycomics
Semeňuk et al. Synthesis of chitooligomer-based glycoconjugates and their binding to the rat natural killer cell activation receptor NKR-P1
US10758890B2 (en) Substrate for the purification of biological liquids
EP0873414A1 (fr) Galactopyranosides et leur utilisation
Chatterjee et al. Synthesis of Neo glycoproteins containing the 3, 6-di-O-methyl-β-d-glucopyranosyl epitope and their use in serodiagnosis of leprosy
JP2013541500A (ja) 組換えレクチン、結合部位修飾レクチンおよびそれらの用途
McBerney et al. Bioorthogonal, Bifunctional Linker for Engineering Synthetic Glycoproteins
WO1988000951A1 (fr) Procede de preparation d'oxazolines de peracetyle
US4767845A (en) Synthesis of tumor antigenic determinant
Fernandez-Santana et al. Conjugation of 5-azido-3-oxapentyl glycosides with thiolated proteins through the use of thiophilic derivatives
US5312903A (en) Lysine-glycosylated recombinant interleukin-2
US10751698B2 (en) Method for the purification of whole blood or a blood-derived product
Ivanova et al. Synthesis of bivalent neogalactolipids via modified Staudinger reaction
CA2114629C (fr) Conjugues a recepteurs pour le ciblage d'antibiotiques a des bacteries

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): CA JP

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE

AK Designated states

Kind code of ref document: A3

Designated state(s): CA JP

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 2081665

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 1991911062

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1991911062

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1991911062

Country of ref document: EP