From Penicillin to Penem and Carbapenem. VII. Synthesis and Antibacterial Activity of Penem Derivatives

Chemical and Pharmaceutical Bulletin

Volumn 34, Issue 3, 1986, Pages 999-1014

  Fujimoto, Katsumi ^a   Sugawara, Shinichi ^b   Iwano, Yuji ^a   Hirai, Koichi ^a  

^a Exploratory Chem Res Laboratories   (Japan)

^b DAIICHI SANKYO CO   (Japan)

Author keywords

4 acetoxyazetidin 2 one; MIC; penem; structure activity relationship; thienamycin; thiocarboxylic acid; Wittig condensation

Indexed keywords

NEW DRUG; THIENAMYCIN;

2 PENEM DERIVATIVE; 6 (1 HYDROXYETHYL) 2 (2 PYRROLIDIN 2 YLMETHYL) 2 PENEM 3 CARBOXYLIC ACID; ANIMAL EXPERIMENT; BIOAVAILABILITY; DOSE RESPONSE; DRUG ANALYSIS; DRUG COMPARISON; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG RESPONSE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; ORAL DRUG ADMINISTRATION; STRUCTURE ACTIVITY RELATION;

ANTIBIOTICS, LACTAM; BACTERIA; PENICILLINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0022653077     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.34.999     Document Type: Article

References (19)

1. I. Ernest, J. Gosteli, C. W. Greengrass, W. Holick, D. E. Jackman, H. R. Pfaendler, and R. B. Woodward, J. Am. Chem. Soc., 100, 8214 (1978)
2. M. Lang, K. Prasad, W. Holick, J. Gosteli, I. Ernest, and R. B. Woodward, J. Am. Chem. Soc., 101, 6296 (1979)
3. H. R. Pfaendler, J. Gosteli, and R. B. Woodward, J. Am. Chem. Soc., 102, 2039 (1980)
4. H. R. Pfaendler, J. Gosteli, R. B. Woodward, and G. Rihs, J. Am. Chem. Soc., 103, 4526 (1981)
5. S. Hanessian, A. Bedeschi, C. Battistini, and N. Mongelli, J. Am. Chem. Soc., 107, 1438 (1985) and references cited therein.
6. D. B. R. Johnston, S. M. Schmitt, F. A. Bouffard, and B. G. Christensen, J. Am. Chem. Soc., 100, 313 (1978)
7. D. H. Shih, J. Hannah, and B. G. Christensen, J. Am. Chem. Soc., 100, 8004 (1978)
8. L. D. Cama and B. G. Christensen, J. Am. Chem. Soc., 100, 8006 (1978)
9. W. J. Leanza, K. J. Wildonger, J. Hannah, D. H. Shih, R. W. Ratcliffe, L. Barash, E. Walton, R. A. Firestone, G. F. Patel, F. M. Kahan, J. S. Kahan, and B. G. Christensen, “Recent Advances in the Chemistry of β-Lactam Antibiotics,” Second International Symposium, Cambridge, England, ed. by G. I. Gregory, The Royal Society of Chemistry, 1980, p. 240.
10. K. Hirai, Y. Iwano, and K. Fujimoto, Heterocycles, 17, 201 (1982).
11. J. P. Clayton, J. Chem. Soc. (C), 1969, 2123.
12. F. DiNinno, T. R. Beattie, and B. G. Christensen, J. Org. Chem., 42, 2960 (1977).
13. W. J. Leanza, F. DiNinno, D. A. Muthard, R. R. Wilkening, K. J. Wildonger, R. W. Ratcliffe, and B. G. Christensen, Tetrahedron, 39, 2505 (1983).
14. A. Yoshida, T. Hayashi, N. Takeda, S. Oida, and E. Ohki, Chem. Pharm. Bull., 29, 2899 (1981).
15. C-P. Mak and H. Fliri, Tetrahedron Lett., 26, 1433 (1985).
16. J. P. Clayton, J. H. C. Nayler, M. J. Pearson, and R. Southgate, J. Chem. Soc., Perkin Trans. 1, 1974, 22.
17. K. Clauss, D. Grimm, and G. Prossel, Justus Liebigs Ann. Chem., 1974, 539.
18. L. Balaspiri, B. Penke, G.Y. Papp, G.Y. Dombi, and K. Kovacs, Helv. Chim. Acta, 58, 969 (1975).
19. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 43, 2923 (1978).