Synthesis and structure-activity relationships of a novel oral carbapenem, CS-834

Journal of Antibiotics

Volumn 50, Issue 5, 1997, Pages 429-439

  Miyauchi, Masao ^a   Endo, Rokuro ^a   Hisaoka, Masafumi ^a   Yasuda, Hiroshi ^a   Kawamoto, Isao ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 (1 HYDROXYETHYL) 4 METHYL 7 OXO 3 (5 OXO 3 PYRROLIDINYLTHIO) 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID PIVALOYLOXYMETHYL ESTER; AMIDE; CARBAPENEM DERIVATIVE; ESTER DERIVATIVE; PEPTIDASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC BIOSYNTHESIS; AREA UNDER THE CURVE; ARTICLE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG HALF LIFE; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; DRUG URINE LEVEL; INTRAVENOUS DRUG ADMINISTRATION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SUBCUTANEOUS DRUG ADMINISTRATION;

EID: 0030918407     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.50.429     Document Type: Article

References (23)

1. KAHAN, J. S.; F. M. KAHAN, R. GOEGELMAN, S. A. CURRIE, M. JACKSON, E. O. STAPLEY, T. W. MILLER, A. K. MILLER, D. HENDLIN, S. MOCHALES, S. HERNANDEZ, H. B. WOODRUFF & J. BIRNBAUM: Thienamycin, a new β-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties. J. Antibiotics 32: 1-12, 1979
2. KROPP, H.; J. G. SUNDELOF, R. HAJDU & F. M. KAHAN: Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase, dehydropeptidase-I. Antimicrob. Agents Chemother. 22: 62-70, 1982
3. LEANZA, W. J.; K. J. WILDONGER, T. W. MILLER & B. G. CHRISTENSEN: N-Acetimidoyl and N-formimidoylthienamycin derivatives: Antipseudomonal β-lactam antibiotics. J. Med. Chem. 22: 1435-1436, 1979
4. MIYADERA, T.; Y. SUGIMURA, T. HASHIMOTO, T. TANAKA, K. IINO, T. SHIBATA & S. SUGAWARA: Synthesis and in vitro activity of a new carbapenem, RS-533. J. Antibiotics 36: 1034-1039, 1983
5. SUNAGAWA, M.; H. MATSUMURA, T. INOUE, M. FUKASAWA & M. KATO: A novel carbapenem antibiotic, SM-7338: Structure activity relationships. J. Antibiotics 43: 519-532, 1990
6. UBUKATA, K.; M. HIKIDA, K. NISHIKI, Y. FURUKAWA, K. TASHIRO, M. KONNO & S. MITSUHASHI: In vitro activity of LJC 10,627, a new carbapenem antibiotic with high stability to dehydropeptidase-I. Antimicrob. Agents Chemother. 34: 994-1000, 1990
7. OKAMOTO, O.; H. FUKATSU, S. NAKAGAWA & N. TANAKA: BO-2727 and its related compounds, new β-methyl carbapenems. Abstracts of the 33th Intersci. Conf. on Antimicrob. Agents Chemother. Abstract No.898, p. 284, New Orleans, Louisiana, Oct. 17-20, 1993
8. ISO, Y.; T. IRIE, Y. NISHINO, K. MOTOKAWA & Y. NISHITANI: A novel 1β-methylcarbapenem antibiotic, S-4661 synthesis and structure-activity relationships of 2-(5-substituted pyrrolidin-3-ylthio)-1β-methylcarbapenems. J. Antibiotics 49: 199-209, 1996
9. GAVIRAGHI, G.: Tribactams: A new prospect in β-lactam chemotherapy. Eur. J. Med. Chem. 30 (Suppl.): 467S-478S, 1995
10. DI MODUGNO, E.; I. ERBETTI, L. FERRARI, G. GALASSI, S. M. HAMMOND & L. XERRI: In vitro activity of the tribactam GV-104326 against Gram-positive, Gram-negative, and anaerobic bacteria. Antimicrob. Agents Chemother. 38: 2362-2368, 1994
11. TAMBURINI, B.; A. PERBONI, T. ROSSI, D. DONATI, D. ANDREOTTI, G. GAVIRAGHI, R. CARLESSO & C. BISMARA (Glaxo): Eur. Pat. Appl. 416,953, March 13, 1991
12. SHIH, D. H.; F. BAKER, L. CAMA & B. G. CHRISTENSEN: Synthetic carbapenem antibiotics I. 1-β-Methylcarbapenem. Heterocycles 21: 29-40, 1984
13. KAWAMOTO, I.; M. MIYAUCHI, R. ENDO, M. HISAOKA, H. YASUDA & S. KUWAHARA: CS-834, a new oral carbapenem: I. Structure-activity relationships of 2-substituted 1β-methylcarbapenems. The 36th Intersci. Conf. on Antimicrob. Agents Chemother., Abstract No. F-105, p. 118, New Orleans, Louisiana, Sept. 15-18, 1996
14. SHIH, D. H.; L. CAMA & B. G. CHRISTENSEN: Synthetic carbapenem antibiotics III. 1-Methyl thienamycin. Tetrahedron Lett. 26: 587-590, 1985
15. RATCLIFFE, R. W.; T. N. SALTZMANN & B. G. CHRISTENSEN: A novel synthesis of the carbapen-2-em ring system. Tetrahedron Lett. 21: 31-34, 1980
16. OIDA, S.; A. YOSHIDA & E. OHKI: synthetic approach directed at 1-carbapenems and 1-carbapenems. Chem. Pharm. Bull. 28: 3494-3500, 1980
17. PELLEGATA, R.: An improved synthesis of γ-, δ-, and ε-lactams. Synthesis 1978: 614-616, 1978
18. MIYAUCHI, M.; O. KANNO & I. KAWAMOTO: Orally active carbapenems 2. Chemical stability of pivaloyloxymethyl ester of carbapenems and cephalosporins in phosphate buffer solution. in preparation
19. MIYAUCHI, M.; K. SASAHARA, K. FUJIMOTO, I. KAWAMOTO, J. IDE & H. NAKAO: Studies on orally active cephalosporin esters. II. Chemical stability of Pivaloyloxymethyl cephalosporin esters in phosphate buffer solution. Chem. Pharm. Bull. 37: 2369-2374, 1989
20. FUJIMOTO, K.; S. ISHIHARA, H. YANAGISAWA, J. IDE, E. NAKAYAMA, H. NAKAO, S. SUGAWARA & M. IWATA: Studies on orally active cephalosporin esters. J. Antibiotics 40: 370-384, 1987
21. KAHAN, F. M.; H. KROPP, J. G. SUNDELOF & J. BIRMBAUM: Thienamycin: Development of imipenem-cilastatin. J. Antimicrob. Chemother. 12 (Suppl. D): 1-35, 1983
22. OHYA, S.; T. FUKUOKA, T. KOGA, T. TAKENOUCHI, H. KAWADA, T. HARASAKI, A. HIRASAWA, C. ISHII, E. SAKAGAWA, M. KUBOTA, H. YASUDA, M. IWATA & S. KUWAHARA: CS-834, a new oral carbapenem: III. In vivo evaluation of CS-834. The 36th Intersci. Conf. on Antimicrob. Agents Chemother., Abstract No. F-107, p. 118, New Orleans, Louisiana, Sept. 15-18, 1996
23. CAMBELL, B. J.: Renal dipeptidase. Methods Enzymol. 19: 722-729, 1970