Synthesis and pharmacological properties of a close analogue of an antithrombotic pentasaccharide (SR 90107A/ORG 31540)

Journal of Medicinal Chemistry

Volumn 40, Issue 11, 1997, Pages 1600-1607

  Petitou, Maurice ^a   Duchaussoy, Philippe ^a   Jaurand, Guy ^a   Gourvenec, Françoise ^a   Lederman, Isidore ^a   Strassel, Jean Marc ^a   Bârzu, Tereza ^a   Crépon, Bertrand ^a   Hérault, Jean Pascal ^a   Lormeau, Jean Claude ^a   Bernat, André ^a   Herbert, Jean Marc ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITHROMBIN III; FONDAPARINUX; GLUCOPYRANOSIDE; GLUCOSE DERIVATIVE; PENTASACCHARIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG ELIMINATION; DRUG HALF LIFE; DRUG POTENCY; DRUG STRUCTURE; DRUG SULFATION; DRUG SYNTHESIS; INTRAVENOUS DRUG ADMINISTRATION; MALE; NONHUMAN; RAT; VEIN THROMBOSIS;

ANIMALS; ANTITHROMBIN III; FACTOR XA; FIBRINOLYTIC AGENTS; HALF-LIFE; HUMANS; HYDROXYLATION; MALE; METHYLATION; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATES; THROMBIN; THROMBOSIS;

EID: 0030969911     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960726z     Document Type: Article

References (24)

1. Olson, S. T.; Björk, I. Regulation of Thrombin Activity by Antithrombin and Heparin. Semin. Thromb. Hemostasis 1994, 20, 373-409.
2. Choay, J.; Petitou, M.; Lormeau, J. C.; Sinaÿ, P.; Casu, B.; Gatti, G. Structure-Activity Relationship in Heparin: a Synthetic Pentasaccharide with High Affinity for Antithrombin III and Eliciting High Anti-Factor Xa Activity. Biochem. Biophys. Res. Commun. 1983, 116, 492-499.
3. Walenga, J. M.; Petitou, M.; Lormeau, J. C.; Samama, M.; Fareed, J.; Choay, J. Antithrombotic Activity of a Synthetic Heparin Pentasaccharide in a Rabbit Stasis Thrombosis Model Using Different Thrombogenic Challenges. Thromb. Res. 1987, 46, 187-198.
4. van Boeckel, C. A. A.; Petitou, M. The Unique Antithrombin III Binding Domain of Heparin: a Lead to New Synthetic Antithrombotics. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1690.
5. Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Sinay, P.; Jacquinet, J.-C.; Torri, G. Synthesis of Heparin Fragments: A α-Methyl Pentaoside with High Affinity for Antithrombin III. Carbohydr. Res. 1987, 167, 67-75.
6. Petitou, M.; Jaurand, G.; Derrien, M.; Duchaussoy, P.; Choay, J. A New, Highly Potent, Heparin-Like Pentasaccharide Fragment Containing a Glucose Residue Instead of a Glucosamine. Bioorg. Med. Chem. Lett. 1991, 2, 95-98.
7. Jaurand, G.; Basten, J.; Lederman, I.; van Boeckel, C. A. A.; Petitou, M. 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. 1992, 2, 897-900.
8. Basten, J.; Jaurand, G.; Olde-Hanter, B.; Petitou, M.; van Boeckel, C. A. A. 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. 1992, 2, 901-904.
9. Basten, J.; Jaurand, G.; Olde-Hanter, B.; Duchaussoy, P.; Petitou, M.; van Boeckel, C. A. A. Biologically Active Heparin-Like Fragments with a "Non-Glycosamino"Glycan Structure. Part 3: O-alkylated-O-sulphated Pentasaccharides. Bioorg. Med. Chem. Lett. 1992, 2, 905-910.
10. Westerduin, P.; van Boeckel, C. A. A.; Basten, J. E. M.; Broekhoven, M. A.; Lucas, H.; Rood, A.; van der Heijden, H.; van Amsterdam, R. G. M.; van Dinther, T. G.; Meuleman, D. G.; Visser, A.; Vogel, G. M. T.; Damm, J. B. L.; Overklift, G. T. Feasible Synthesis and Biological Properties of Six "Non-Glycosamino"Glycan Analogues of the Antithrombin III Binding Heparin Pentasaccharide. Bioorg. Med. Chem. 1994, 2, 1267-83.
11. Küster, J. M.; Dyong, I. Synthese aller Methyl-mono-, Methyl-di- und Methyl-tri-O-benzyl-α-D-glucopyranoside. Justus Liebigs Ann. Chem. 1975, 2179-2189.
12. Mallet, J.-M.; Meyer, G.; Yvelin, F.; Jutand, A.; Amatore, C.; Sinaÿ, P. Electrosyntheses of disaccharides from phenyl or ethyl 1-thioglycosides. Carbohydr. Res. 1993, 244, 237-246.
13. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Iodonium ion promoted reactions at the anomeric centre. II. An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters. Tetrahedron Lett. 1990, 31, 1331-1334.
14. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Iodonium promoted reactions of disarmed thioglycosides. Tetrahedron Lett. 1990, 31, 4313-4316.
15. van Boeckel, C. A. A.; Beetz, T.; Vos, J. N.; de Jong, A. J. M.; van Aelst, S. F.; van den Bosch, R. H.; Mertens, J. M. R.; van den Flugt, F. A. Synthesis of a Pentasaccharide Corresponding to the Antithrombin III Binding site of heparin. J. Carbohydr. Chem. 1985, 4, 293-321.
16. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-124.
17. (a) Pecka, J.; Cerny, M. Syntheses with Anhydro Sugars. XV. Syntheses of 1,6-Anhydro-2,3,4-trideoxy-β-D-Glycero-Hexopyranose and its Unsaturated Derivatives of Model Substances for Investigations on the Optical Rotation of Sugars. Collect. Czech. Chem. Commun. 1973, 38, 132-142.
18. (b) Carlson, L. J. Preparation of 2- and 4-substituted D-glucose derivatives from 1,6-anhydro-β-D-glucopyranose. J. Org. Chem. 1965, 30, 3953-3955.
19. Atha D. H.; Lormeau J. C.; Petitou M.; Rosenberg R. D.; Choay J. Contribution of 3-O- and 6-O-Sulfated Glucosamine Residues in the Heparin-Induced Conformational Change in Antithrombin III. Biochemistry 1987, 26, 6454-6461.
20. Teien, A. N.; Lie, M. Evaluation of an Amidolytic Heparin Assay Method: Increased Sensitivity by Adding Purified Antithrombin III. Thromb. Res. 1977, 10, 399-410.
21. Hemker, H. C.; Wielders, S.; Kessels, H.; Béguin, S. A Continuous Registration of Thrombin Generation in Plasma, its Use for the Determination of the Thrombin Potential. Thromb. Haemost. 1993, 70, 617-624.
22. Vogel, G. M.; Meuleman, D. G.; Bourgondieu, F. G.; Hobbelem, M. Comparison of Two Experimental Thrombosis Models in Rats: Effect of Four Glycosaminoglycans. Thromb. Res. 1989, 54, 399-410.
23. van Amsterdam, R. G. M.; Vogel, G. M. T.; Visser, A.; Kop, W. J.; Buiting, M. T.; Meuleman, D. G. Synthetic Analogues of the Antithrombin III-Binding Pentasaccharide Sequence of Heparin. Prediction of In Vivo Residence Times. Arterioscler. Thromb. Vasc. Biol. 1995, 15, 493-503.
24. McKay, J. E. A Simple Two-Step Procedure for the Isolation of Antithrombin III from Biological Fluids. Thromb. Res. 1981, 21, 375-382.