A very short, efficient and inexpensive synthesis of the prodrug form of SC-54701A. A platelet aggregation inhibitor

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 13, 1997, Pages 1699-1700

  Cossy, J ^a   Schmitt, A ^a   Cinquin, C ^a   Buisson, D ^b   Belotti, D ^a  

^a CNRS   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 [[4 [[4 (AMINOIMINOMETHYL)PHENYL]AMINO] 1,4 DIOXOBUTYL]AMINO] 4 PENTYNOIC ACID; 4 AMINOBENZAMIDINE; ACETYLENE DERIVATIVE; ANTITHROMBOCYTIC AGENT; ARGINYLGLYCYLASPARTIC ACID; FIBRINOGEN RECEPTOR ANTAGONIST; MORPHOLINE DERIVATIVE; PRODRUG; PYRIDINE DERIVATIVE; SUCCINIC ANHYDRIDE; TETRABUTYLAMMONIUM; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HEART INFARCTION; NONHUMAN; ORAL DRUG ADMINISTRATION; STROKE; THROMBOCYTE AGGREGATION INHIBITION; UNSTABLE ANGINA PECTORIS;

ANGINA;

EID: 0030873624     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00293-X     Document Type: Article

References (18)

1. Moran, J. Thrombolytic Treatment: The Market, Clinical Background and Future Therapies, SCRIP-PJB Publication: New York, 1990.
2. (a) Plow, E. F.; Pierschbacher, M. D.; Ruoslahti, E.; Marguerie, G.; Ginsberg, M. H. Blood 1987, 70, 110-115.
3. (b) Andrieux, A.; Charon, M. H.; Hufry-Clergeon, G.; Chapel, A.; Marguerie, G. Colloq. INSERM 1989, 174, 567-570.
4. (a) Zablocki, J. A.; Miyano, M.; Garland, B.; Pireh, D.; Schretzman, L.; Rao, S. N.; Lindmark, R. J.; Panzer-Knodle, S.; Nicholson, N.; Taite, B.; Salyers, A.; King, L.; Feigen, L. J. Med. Chem. 1993, 36, 811-1819.
5. (b) Zablocki, J. A.; Miyano, M.; Rao, S. N.; Panzer-Knodle, S.; Nicholson, N.; Feigen, L. J. Med. Chem. 1992, 35, 4914-4917.
6. (a) Hartman, G. D.; Egbertson, M. S.; Halczenko, W.; Laswell, W. L.; Duggan, M. E.; Smith, R. L.; Naylor, A. M.; Manno, P. D.; Lynch, R. J.; Zhang, G.; Chang, C. T.-C.; Gould, R. J. J. Med. Chem. 1992, 35, 4640-4642.
7. (b) Alig, L.; Edenhofer, A.; Harvary, P.; Hurzeler, M.; Knopp, D.; Muller, M.; Steiner, B.; Trzeciak, A.; Weller, T. J. Med. Chem. 1992, 35, 4393-4407.
8. (a) Gould, R. J.; Barrett, J. S.; Eiss, J. D.; Holahan, M. A.; Stranieri, M. T.; Theoarides, A. D.; Lynch, J. J. Jr.; Friedman, P. A.; Duggan, M. E.; Ihle, N. C.; Anderson, P. S.; Hartman, G. D. Thromb. Haemostat. 1993, 69, a2.
9. (b) Pike, N. B.; Foster, M. R.; Hornby, E. J.; Lumley, P. Thromb. Haemostas. 1993, 69, 1886.
10. Zablocki, A. J.; Rico, J. G.; Garland, R. B.; Rogers, T. E.; Williams K.; Schretzman, L. A.; Rao, S. A.; Bovy, P. R.; Tjoeng F. S.; Lindmark R. J.; Toth, M.; Zupec, M.; McMackins, D. E.; Adams, S. P.; Miyano M.; Markos, C. S.; Milton, M. R; Paulson, S.; Herin M.; Jacquin, P.; Nicholson, N.; Panzer-Knodle, S. G.; Haas, N. F.; Page, J. D.; Szalony, J. A.; Taite, B. B.; Salyers A. K.; King, L. W.; Campion, J. G.; Feigen, L. P. J. Med. Chem. 1995, 38, 2378-2394.
11. Kraihanzel, C. S.; Losee, M. L. J. Org. Chem. 1968, 33, 1983-1986.
12. Cossy, J.; Belotti, D.; Schmitt, A.; Cinquin, C. unpublished results.
13. Ansari, M. H.; Kusumoto, T.; Hiyama, T. Tetrahedron Lett. 1993, 34, 8271-8274.
14. The ee of 4 was measured by GC after esterification with (S)-O-acetylpropanoyl chloride and calibration with racemic material.
15. Buisson, D.; Azerad, R.; Cossy, J.; Cinquin, C.; Schmitt, A. unpublished results.
16. Mitsunobu, O. Synthesis 1981, 1-28.
17. Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190-192.
18. 6