Studies on quinolone antibacterials. IV. Structure-activity relationships of antibacterial activity and side effects for 5- or 8-substituted and 5,8-disubstituted-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-1,4-dihydro-4- oxoquinoline-3-carboxylic acids

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 5, 1996, Pages 1074-1085

  Yoshida, Toshihiko ^a   Yamamoto, Yoichi ^a   Orita, Hitomi ^a   Kakiuchi, Masato ^a   Takahashi, Yoshie ^a   Itakura, Masakazu ^a   Kado, Noriyuki ^a   Mitani, Kazuya ^a   Yasuda, Shingo ^a   Kato, Hideo ^a   Itoh, Yasuo ^a  

^a Abbott Japan Co Ltd   (Japan)

Author keywords

5 amino 8 methylquinolone; 5 substituted quinolone; 8 substituted quinolone; Antibacterial activity; Chromosome; Phototoxicity

Indexed keywords

5 AMINO 7 (3 AMINO 1 PYRROLIDINYL) 1 CYCLOPROPYL 6 FLUORO 1,4 DIHYDRO 8 METHYL 4 OXO 3 QUINOLINECARBOXYLIC ACID; CIPROFLOXACIN; CLINAFLOXACIN; FENBUFEN; GATIFLOXACIN; OFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; CHROMOSOME DAMAGE; CONTROLLED STUDY; CONVULSION; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; GUINEA PIG; INTRAPERITONEAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; LUNG ALVEOLUS CELL; MALE; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PHOTOTOXICITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION;

4-QUINOLONES; ANIMALS; ANTI-INFECTIVE AGENTS; CELL LINE; CRICETINAE; CRICETULUS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; GUINEA PIGS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MICE; MICE, INBRED ICR; MUTAGENICITY TESTS; PHOTOSENSITIVITY DISORDERS; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029955365     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1074     Document Type: Article

References (40)

1. a) Part II: Yoshida T., Yamamoto Y., Yagi N., Takahashi Y., Yasuda S., Katoh H., Itoh Y., Yakugaku Zasshi, 111, 19-31 (1991);
2. b) Part III: Yoshida T., Yamamoto Y., Yagi N., Takahashi Y., Yasuda S., Katoh H., Itoh Y., ibid., 111, 386-392 (1991).
3. Wise R., Andrews J. M., Edwards L. J., Antimicrob. Agents Chemother., 23, 559-564 (1983).
4. Hayakawa I., Hiramitsu T., Tanaka Y., Chem. Pharm. Bull., 32, 4907-4913 (1984).
5. Miyamoto T., Matsumoto J., Chiba K., Egawa H., Shibamori K., Minamida A., Nishimura Y., Okada H., Kataoka M., Fuzita M., Hirose T., Nakano J., J. Med. Chem., 33, 1645-1656 (1990).
6. Ueda Y., Shimizu K., Konno M., Matsumoto F., (ed.), "The Quinolones," Life Science Publisher, Tokyo, 1991, pp. 128-145.
7. a) Gootz T. D., Barrett J. F., Sutcliffe J. A., Antimicrob. Agents Chemother., 34, 8-12 (1990);
8. b) Shimada H., Itoh S., Program and Abstracts of 31st ICAAC 1991, American Society for Microbiology, Washington DC, Abstr. no. 1507.
9. a) Ledoussal B., Bouzard D., Coroneos E., J. Med. Chem., 35, 198-200 (1992);
10. b) Petersen U., Schenke T., Schriewer M., Krebs A., Grohe K., Haller I., Metzger K. G., Endermann R., Zeiler H. J., European Patent 391169 (1990) [Chem. Abstr., 114, 185466v (1991)];
11. c) Ciavavino V., Suto M. J., Theiss J. C., Mutat. Res., 298, 227-236 (1993) [Chem. Abstr., 118, 182640u (1993)].
12. c) Ciavavino V., Suto M. J., Theiss J. C., Mutat. Res., 298, 227-236 (1993) [Chem. Abstr., 118, 182640u (1993)].
13. a) Masuzawa K., Suzue S., Hirai K., Ishizaki T., European Patent 237955 (1987) [Chem. Abstr., 108, 75234m (1988)];
14. b) Iwata M., Kimura T. Inoue T., Fujihara Y., Katsube T., European Patent 352123 (1988) [Chem. Abstr., 113, 78178k (1990)];
15. c) Iwata M., Kimura T. Inoe T., Fujiwara Y., Katsube T., Japan Kokai Tokkyo Koho, Japan. Patent 05255183 (1993) [Chem. Abstr., 120, 217312j (1994)];
16. d) Domagala J. M., Bridges A. J., Culbertson T. P., Gambino L., Hagen S. E., Karrick G., Porter K. Sanchez J. P., Sesnie J. A. Spense G. Szotek D., Wemple J., J. Med. Chem., 34, 1142-1154 (1991);
17. e) Domagala J. M., Mich T. F., Sanchez Joseph P., European Patent 265230 (1988) [Chem. Abstr., 109, 92826u (1988)];
18. f) Ueda H., Miyamoto H., Yamashita H., Tone H., European Patent 287951 (1988) [Chem. Abstr., 110, 173109k (1989)];
19. g) Domagala J. M., Hagen S. E., Kiely J. S., World Intellectual Property Organization Patent 8906649 (1989) [Chem. Abstr., 112, 98508a (1990)].
20. a) Ishikawa R., Kaieda O., Takatani N., Japan Kokai Tokkyo Koho, Japan. Patent 62185066 (1987) [Chem. Abstr., 108, 21511f (1988)];
21. b) Hiromoto K., Otsubo A., Japan Kokai Tokkyo Koho, Japan. Patent 63162669 (1988) [Chem. Abstr., 110, 57311w (1989)].
22. a) Ataka K., Oku M., Omori K., Kimura T., Iwata M., Japan Kokai Tokkyo Koho, Japan. Patent 63316757 (1989) [Chem. Abstr., 111, 97105j (1989)];
23. b) Hayakawa I., Kimura Y., Japan Kokai Tokkyo Koho, Japan. Patent 0372476 (1991) [Chem. Abstr., 115, 71622h (1991)].
24. Hagen S. E., Domagala J. M., J. Heterocyclic Chem., 27, 1609-1616 (1990).
25. Wemple J. N., Karrick G. L., Spence F. G., U. S. Patent 4885386 (1989) [Chem. Abstr., 112, 216450a (1990)].
26. Fujita T., Iwasa J., Hansch C., J. Am. Chem. Soc., 86, 5175-5180 (1964).
27. Verloop A., Hoogenstraaten, W., Tipker J., "Drug Design," Vol. VII, ed., by Ariens E. J., Academic Press Publisher, New York, 1976, pp. 180-185.
28. Ohta M., Koga H., J. Med. Chem., 34, 131-139 (1991).
29. Hagen S. E., Domagala J. M. Heifetz C. L., Johnson J., J. Med. Chem., 34, 1155-1161 (1991).
30. Suto M. J., Domagala J. M., Roland G. E., Mailloux G. B., Cohen M. A., J. Med. Chem., 35, 4745-4750 (1992).
31. Moran D. B., Ziegler C. B., Dunne T. S., Kuck N. A., Lin Y., J. Med. Chem., 32, 1313-1318 (1989).
32. a) Shen L. L., Kohlbrenner W. E., Weigl D., Baranowski J., J. Biol. Chem., 264, 2973-2978 (1989);
33. b) Shen L. L., Mitscher L. A., Sharma P. N., O'Donnell T. T., Chu D. W. T., Cooper C. S., Rosen T., Pernet A. G., Biochemistry, 28, 3886-3894 (1989).
34. Itoh Y., Kato H., Ogawa N., Koshinaka E., Suzuki T., Yagi N., Ger. Offen. Patent 3433924 (1985) [Chem. Abstr., 103, 123517b (1985)].
35. Kimura U., Yamada M., Nii S., Kumon Y., Omori H., Chemotherapy, 43, 357-360 (1995).
36. Domagala J. M., J. Antimicrob. Chemother., 33, 685-706 (1994).
37. a) Ueda Y., Shimizu K., Konno M., Matsumoto F., (ed.), "The Quinolones," Life Science Publisher, Tokyo, 1991, pp. 315-326;
38. b) Akahane K., Sekiguchi M., Une T., Osada Y., Antimicrob. Agents Chemother., 33, 1704-1708 (1989).
39. Goto S., Jo K. Kawakita T., Kosakai N., Mitsuhashi S., Nishino T. Ohsawa N. Tanami H. Chemotherapy, 29, 76-79 (1981).
40. Satou E., Katumura Y., Itikawa H., Kobayasi T., Nakazima K., Nishinihon J. Dermatol., 42, 831-837 (1980).