Synthetic heparin pentasaccharides

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S123000, C514S054000, C514S056000

Reexamination Certificate

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07541445

ABSTRACT:
Preparation of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides for use in the preparation of synthetic heparinoids.

REFERENCES:
patent: 4401662 (1983-08-01), Lormeau et al.
patent: 4496550 (1985-01-01), Lindahl et al.
patent: 4607025 (1986-08-01), Petitou et al.
patent: 4818816 (1989-04-01), Petitou et al.
patent: 5939588 (1999-08-01), Soloshonok et al.
patent: 6846917 (2005-01-01), Seeberger et al.
patent: 2003/0013862 (2003-01-01), Seeberger et al.
patent: 2005/0187381 (2005-08-01), Seeberger et al.
patent: 10397/83 (1983-08-01), None
patent: 42637/85 (1985-11-01), None
patent: 0082793 (1983-06-01), None
patent: 0 084 999 (1983-08-01), None
patent: 0 084 999 (1983-08-01), None
patent: 0333243 (1989-09-01), None
patent: 2 531 436 (1984-02-01), None
patent: 2531436 (1984-02-01), None
patent: 63-218691 (1988-09-01), None
patent: 63-218691 (1988-09-01), None
patent: 3-237101 (1991-10-01), None
patent: 3-237101 (1991-10-01), None
patent: 10-182576 (1998-07-01), None
patent: WO 82/03863 (1982-11-01), None
patent: WO 95/03316 (1995-02-01), None
Greene et al., “Protective groups in Organic Synthesis, Second edition” Published by John Wiley and Sons, (1999) pp. 46-52, 88-92, and 413-420.
Greene et al., Protective Groups in Organis Synthesis, published 1999 by John Wiley and Sons, pp. 42-46, 53-54, 83-84, 100-103, 413-452.
Ichikawa et al., “Synthesis of a Heparin Pentasaccharide Fragment with a High Affinity for Antithrombin III Employing Cellobiose as a key Starting Material” Tetrahedron Letters (1986) vol. 27, No. 5, pp. 611-614.
Basten, J. et al. (1992). “Biologically Active Heparin-like Fragments with a “Non-Glycosamino” Glycan Structure. Part 2: A Tetra-O-Methylated Pentasaccharide with High Affinity for Antithrombin III,”Bioorg. Med. Chem. Lett. 2(9):901-904.
Beetz, T. et al. (1986). “Synthesis of an Antithrombin Binding Heparin-Like Pentasaccharide Lacking 6-O Sulphate at its Reducing End,”Tetrahedron Letters27(48):5889-5892.
Duchaussoy, P. et al. (1991). “The First Total Synthesis of the Antithrombin III Binding Site of Porcine Mucosa Heparin,”Bioorg. Med. Chem. Lett. 1(2):99-102.
Ichikawa, Y. et al. (1988). “Synthesis of Methyl Glycoside Derivatives of Tri- and Penta-Saccharides Related to the Antithrombin III-Binding Sequence of Heparin, Employing Cellobiose as a Key Starting-Material,”Carb. Res. 172(1):37-64.
International Search Report mailed Jan. 13, 2003 for PCT Application No. PCT/AU02/01228, 6 pages.
Jaurand, G. et al. (Sep. 1992). “Biologically Active Heparin-like Fragments with a “Non-Glycosamino” Glycan Structure. Part 1: A Pentasaccharide Containing a 3-O-Methyl Iduronic Acid Unit,”Bioorg. Med. Chem. Lett. 2(9):897-900.
Lei, P-S. et al. (1998). “Synthesis of a 3-Deoxy-L-iduronic Acid Containing Heparin Pentasaccharide to Probe the Conformation of the Antithrombin III Binding Sequence,”Biororg. Med. Chem. 6:1337-1346.
Love, K.R. et al. (2001). “Linear Synthesis of a Protected H-Type II Pentasaccharide Using Glycosyl Phosphate Building Blocks,”J. Org. Chem. 66:8165-8176.
Lucas H. et al. (1990). “Syntheses of Heparin-like Pentamers Containing “Opened” Uronic Acid Moieties,”Tetrahedron46(24):8207-8228.
Orgueira, H.A. et al. (2003). “Modular Synthesis of Heparin Oligosaccharides,”Chemistry Eur. J. 9(1):140-169.
Petitou, M. (1984). “Synthetic Heparin Fragments: New and Efficient Tools for the Study of Heparin and its Interactions,”Nouv. Rev. Fr. Hematol. 26:221-226.
Petitou, M. et al. (1987). “Synthesis of Heparin Fragments: A Methyl α-Pentaoside with High Affinity for Antithrombin III,”Carbohydrate Research167:67-75.
Petitou, M. et al. (1988). “Binding of Heparin to Antithrombin III: A Chemical Proof of the Critical Role Played by a 3-Sulfated 2-Amino-2-Deoxy-D-Glucose Residue,”Carbohydrate Res. 179:163-172.
Petitou, M. et al. (1991). “A New, Highly Potent, Heparin-like Pentasaccharide Fragment Containing a Glucose Residue Instead of a Glucosamine,”Bioorg. Med. Chem. Lett. 1(2):95-98.
Petitou, M. et al. (1992). “Chemical Synthesis of Heparin Fragments and Analogues,”Fortschr. Chem. Org. Naturst. 60:143-210.
STN File CA Abstract Accession No. 119:181118 for Jaurand, G. et al. (1992). “Biologically Active Heparin-like Fragments with a ‘Non-Glycosamino’ Glycan Structure: Part 1: A Pentasaccharide Containing a 3-O-Methyl Iduronic Acid Unit,”Bioorg. Med. Chem. Lett. 2(9):897-900.
Tamura, J. et al. (1996). “Synthetic Studies of Glycosyl Serines in the Carbohydrate-Protein Region of Protoglycans,”Liebigs Annalen, pp. 1239-1257.
van Aelst, S.F. et al. (Nov. 1987). “Synthesis of an Analogue of the Antithrombin Binding Region of Heparin Containing α-L-Idopyranose,”Recl. Trav. Chim. Pays-Bas106(11):593-595.
van Boeckel, C.A.A. (1997). “Synthetic Heparin-like Antithrombotics,”Pure&Appl. Chem. 69(3):389-394.
van Boeckel, C.A.A. et al. (1985). “Synthesis of a Pentasaccharide Corresponding to the Antithrombin III Binding Fragment of Heparin,”J. Carbohydrate Chemistry4(3):293-321.
van Boeckel, C.A.A. et al. (1988). “Synthesis of a Potent Antithrombin Activating Pentasaccharide: A New Heparin-Like Fragment Containing Two 3-O-Sulphated Glucosamines,”Tetrahedron Letters29(7):803-806.
Vos, J.N. et al. (1991). “Synthesis of a 6-O-Phosphorylated Analogue of the Antihrombin III Binding Sequence of Heparin: Replacement of One Essential Sulphate Group by a Phosphate Group Nullifies the Biological Activity,”Bioorg. Med. Chem. Lett. 1(3):143-146.
Wessel, H.P. et al. (1989). “140. Synthesis of aN-Acetylated Heparin Pentasaccharide and its Anticoagulant Activity in Comparison with the Heparin Pentasaccharide with High Anti-Factor-Xa Activity,”Helv. Chim. Acta72:1268-1277.
STN File CA Abstract Accession No. 104:130179 & Ichikawa, Y. et al., “Synthetic studies on mucopolysaccharides. Part III. Synthesis, from cellobiose of a trisaccharide closely related to the GlcNAc—GlcA—GlcN segment of the antithrombin-binding sequence of herapin”, Carbohydrate Research, 1985, pp. 272-282, vol. 141, No. 2.
STN File CA Abstract Accession No. 136:70031 & Love K R et al., “Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks”, Journal of Organic Chemistry, 2001, pp. 8165-8176, vol. 66, No. 24.
Choay, J. et al. (1981). “Structural Studies on a Biologically Active Hexasaccharide Obtained from Heparin,”Annals of New York Academy of Sciencespp. 644-648.
Choay, J. et al. (Oct. 31, 1983). “Structure-Activity Relationship in Heparin: A Synthetic Pentasaccharide with High Affinity for Antithrombin III and Eliciting High Anti-Factor Xa Activity,”Biochemical and Biophysical Research Communications116(2):492-499.
Lindahl, U. et al. (Nov. 1980). “Evidence for a 3-O-Sulfated D-Glucosamine Residue in the Antithrombin-Binding Sequence of Heparin,”Biochemistry77(11):6551-6555.
Riesenfeld, J. et al. (Mar. 10, 1981). “The Antithrombin-Binding Sequence of Heparin,”The Journal of Biological Chemistry256(5):2389-2394.
Sinay, P. et al. (1984). “Total Synthesis of a Heparin Pentasaccharide Fragment Having High Affinity for Antithrombin III,”Carbohydrate Research132:C5-C9.
Petitou, M. et al. (1986). “Synthesis of Heparin Fragments. A Chemical Synthesis of the Pentasaccharide0-(2-Deoxy-2-Sulfamido-6-O-Sulfo-α-D-Glucopyranosyl)-(1→4)-O-(β-D-Glucopyranosyluronic Acid)-(1→4)-O-(2-Deoxy-2-Sulfamido-3,6-Di-O-Sulfo-α-D-Glucopyranosyl)-(1→4)-O-(2-O-Sulfo-α-L-Idopyranosyluronic Acid)-(1→4)-2-Deoxy-2-Sulfamido-6-O-D-Glucopyranose Decasodium Salt, A Heparin Fragment Having High A

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