An alternative synthesis of a potent GPIIb/IIIa receptor antagonist

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 865-866

  Hayes, Jerome F ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Benzodiazepine; Cyclization; Hydroquinone; Oxidation; Quinone

Indexed keywords

ASPARTIC ACID; BENZODIAZEPINE DERIVATIVE; FIBRINOGEN RECEPTOR ANTAGONIST; HYDROQUINONE DERIVATIVE; LOTRAFIBAN;

ARTICLE; CYCLIZATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0033016558     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3094     Document Type: Article

References (12)

1. Nichols, A.J.; Vasko, J.A.; Koster, P.F.; Valocik, R.E.; Samanen, J.M. In Cellular Adhesion:Molecular Definition to Therapeutic Potential; Metcalf, B.W.; Dalton, B.J.; Poste, G. Eds.; Plenum: New York, 1994, pp213-237.
2. a) Bondinell, W.E.; Callahan, J.F.; Huffman, W.F.; Keenan, R.M.; Ku, T.W.; Newlander, K.A.; Samanen, J.M.; Uzinskas, I.N. WO 9414776, Chem. Abstr. 1994, 123, 112082;
3. b) Miller, W.H.; Ku, T.W.; Ali, F.E.; Bondinell, W.E.; Calvo, R.R.; Davis, L.D.; Erhard, K.F.; Hall, L.B.; Huffman, W.F.; Keenan, R.M.; Kwon, C.; Newlander, K.A.; Ross, S.T.; Samanen, J.M.; Takata, D.T.; Yuan, C.-K. Tetrahedron Lett. 1995, 36, 9433.
4. Etridge, S.K.; Hayes, J.F.; Walsgrove, T.C.; Wells, A.S. WO 9724336, 1997; Chem. Abstr. 1997, 127, 135814.
5. Etridge, S.K.; Hayes, J.F.; Walsgrove, T.C.; Wells, A.S. Organic Process Research and Development, 1999, 3, 60-63. AN 1998:768608.
6. Katritski, A.; Rees, C. Comprehensive Heterocyclic Chemistry, Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol 7, p 608.
7. Walser, A., Fryer, R. I.; Chem. Heterocycl. Compd. 1991, 50, 849-946.
8. For a review concerning the reaction of Fremy's salt with aromatic hydroxy compounds see Zimmer, H.; Lankin, D.C.; Horgan, S.W. Chem. Rev. 1971, 71, 229-246.
9. Teuber, H.-J; Glosauer, O. Chem. Ber. 1965, 98, 2648.
10. 3, 270 MHz) 3.00 (3H, s), 3.75 (3H, s), 4.25 (2H, s br), 5.40 (1H, s), 5.80 (1H, s), 6.70 - 6.80 2H, m), 6.85 (1H, d) and 10.50 (1H, s).
11. Cyclization of an amide group onto a hydroquininone in the presence of silver (I) oxide to give a 3,4-dihydro-1,4-benzodiazepine-2,5-dione has been recently published. However, precise details concerning conditions and yields were not disclosed; Kraus, G.A.; Melekhov, A. Tetrahedron Lett., 1998, 39, 3957.
12. Wells, A.S.; WO 9829561. Chem. Abstr. 1998, 129, 121708.