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Discovery and development of moxalactam (6059‐S): The chemistry and biology of 1‐oxacephems

1981; Wiley; Volume: 1; Issue: 3 Linguagem: Inglês

10.1002/med.2610010302

ISSN

1098-1128

Autores

Hiroharu OTSUKA, Wataru Nagata, M. YOSHIOKA, Masayuki Narisada, Tadashi Yoshida, Yoshinori Harada, Hirotsugu Yamada,

Tópico(s)

Antibiotics Pharmacokinetics and Efficacy

Resumo

Medicinal Research ReviewsVolume 1, Issue 3 p. 217-248 Article Discovery and development of moxalactam (6059-S): The chemistry and biology of 1-oxacephems H. Otsuka, H. Otsuka Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Hideo Otsuka is Director of Shionogi Research Laboratories and eecutive Director of Shionogi & Co., Ltd. He graduated from Osaka lmperial University and received his Ph.D. in science from Osaka University, Japan. He was born in Osaka in 1917 and entered Shionogi & Co., Ltd. in 1947. He has been a member of the Board of Directors of Shionogi & Co., Ltd. since 1963 and was appointed Director of Shionogi Research Laboratories in 1973. Dr. Otuka was a lecturer in Biochemistry at Kobe University and eceived the Society of Kinki Chemical Industry Award for research on bovine pituitary gland hormone. His research interests include isolation and synthesis of peptide hormones and peptide antibiotics as well as developments of medicials inculding β-lactam antibiotics.Search for more papers by this authorW. Nagata, Corresponding Author W. Nagata Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Wataru Nagata is director of Chemical Research at Shionogi research Laboratories. He graduated from Tokyo Imperial University, Japan, conducted chemical research with Professor T. Reichstein for two years at Institute for Organic Chemistry, University of Basel, Switzerland, and received his Ph.D. in organic chemistry from the University of tokyo. He was born in Hyogo, Japan in 1922, entered Shionogi & Co., Ltd. in 1945, and was appointed to the board of Directors of this company in 1974. Dr. Nagata received academic Award of Pharmaceutical Society of Japan in 1961. He ws on the Board of Editors of Organic Synthesis from 1971 to 1976. He has been a lecturer at the Robert A. Welch Foundation Conference on Chemical Research U.S.A., the Wilson Baker Lecture, England, and the Pacific Coast Lecture, U.S.A.; as well as a lecturer in organic chemistry at Kyoto University, Osaka University, Osaka City University, Osaka City University, Hokkaido University, and Todyo University. His research interests include total syntheses of natural, biologically active products, semisyntheses of β-lactam derivatives, and development of synthetic methodologies including hydrocyanation with the use of alkylaluminum compounds.Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, JapanSearch for more papers by this authorM. Yoshioka, M. Yoshioka Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Mitsuru Yoshioka is a research Associate Director at Shionogi Research Laboratories. He received his Ph.D. in organic chemistry from Kyoto University, Japan, and did postdoctorl work at university of California, Berkeley. He was born in Ehime, Japan, in 1931 and entered Shionogi & Co., Ltd, in 1953. His research interests include hydrocyanation using alkylaluminum compounds and synthesis of β-lactam derivatives.Search for more papers by this authorM. Narisada, M. Narisada Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Masayuki Narisada is a research Associate Director at Shionogi Research Laboratories. He received his Ph.D. in organic chemistry from Kyoto University and was a postdoctoral fellow at Harvard Iniversity, Cambridge. He was born in Tokyo in 1932 and has worked at the Laboratories since 1954. His research interests include total synthesis of natural products, synthesis of novel β-lactams, and SAR among them.Search for more papers by this authorT. Yoshida, T. Yoshida Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, JapanSearch for more papers by this authorY. Harada, Y. Harada Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Yoshio Harada is a director of tomicology Divvision, Shionogi Research Laboratories. He was born in Osaka, Japan, in 1929 and received M.D. in 1955 and Doctor of Medical Science from Mie University School of Medicine in 1960. After a two-year medical residentship in the U.S., he was appointed asistant professor in pathology at Yamaguchi University. He joined Shionogi & Co., Ltd. in 1966.Search for more papers by this authorH. Yamada, H. Yamada Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Hideo Yamada is a research Asociate Director at Shionogi Research Laboratories. He received his Ph.D. in the field of pharmacy from Tokyo University, Japan, and did postdoctoral work at State University of New York at Buffalo. He was born in Aichi, Japan, in 1932 and entereed Shionogi & Co., Ltd. in 1957. His research interests include pharmacokinetics and biopharmaceutics of antibiotics and anticancer agents.Search for more papers by this author H. Otsuka, H. Otsuka Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Hideo Otsuka is Director of Shionogi Research Laboratories and eecutive Director of Shionogi & Co., Ltd. He graduated from Osaka lmperial University and received his Ph.D. in science from Osaka University, Japan. He was born in Osaka in 1917 and entered Shionogi & Co., Ltd. in 1947. He has been a member of the Board of Directors of Shionogi & Co., Ltd. since 1963 and was appointed Director of Shionogi Research Laboratories in 1973. Dr. Otuka was a lecturer in Biochemistry at Kobe University and eceived the Society of Kinki Chemical Industry Award for research on bovine pituitary gland hormone. His research interests include isolation and synthesis of peptide hormones and peptide antibiotics as well as developments of medicials inculding β-lactam antibiotics.Search for more papers by this authorW. Nagata, Corresponding Author W. Nagata Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Wataru Nagata is director of Chemical Research at Shionogi research Laboratories. He graduated from Tokyo Imperial University, Japan, conducted chemical research with Professor T. Reichstein for two years at Institute for Organic Chemistry, University of Basel, Switzerland, and received his Ph.D. in organic chemistry from the University of tokyo. He was born in Hyogo, Japan in 1922, entered Shionogi & Co., Ltd. in 1945, and was appointed to the board of Directors of this company in 1974. Dr. Nagata received academic Award of Pharmaceutical Society of Japan in 1961. He ws on the Board of Editors of Organic Synthesis from 1971 to 1976. He has been a lecturer at the Robert A. Welch Foundation Conference on Chemical Research U.S.A., the Wilson Baker Lecture, England, and the Pacific Coast Lecture, U.S.A.; as well as a lecturer in organic chemistry at Kyoto University, Osaka University, Osaka City University, Osaka City University, Hokkaido University, and Todyo University. His research interests include total syntheses of natural, biologically active products, semisyntheses of β-lactam derivatives, and development of synthetic methodologies including hydrocyanation with the use of alkylaluminum compounds.Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, JapanSearch for more papers by this authorM. Yoshioka, M. Yoshioka Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Mitsuru Yoshioka is a research Associate Director at Shionogi Research Laboratories. He received his Ph.D. in organic chemistry from Kyoto University, Japan, and did postdoctorl work at university of California, Berkeley. He was born in Ehime, Japan, in 1931 and entered Shionogi & Co., Ltd, in 1953. His research interests include hydrocyanation using alkylaluminum compounds and synthesis of β-lactam derivatives.Search for more papers by this authorM. Narisada, M. Narisada Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Masayuki Narisada is a research Associate Director at Shionogi Research Laboratories. He received his Ph.D. in organic chemistry from Kyoto University and was a postdoctoral fellow at Harvard Iniversity, Cambridge. He was born in Tokyo in 1932 and has worked at the Laboratories since 1954. His research interests include total synthesis of natural products, synthesis of novel β-lactams, and SAR among them.Search for more papers by this authorT. Yoshida, T. Yoshida Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, JapanSearch for more papers by this authorY. Harada, Y. Harada Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Yoshio Harada is a director of tomicology Divvision, Shionogi Research Laboratories. He was born in Osaka, Japan, in 1929 and received M.D. in 1955 and Doctor of Medical Science from Mie University School of Medicine in 1960. After a two-year medical residentship in the U.S., he was appointed asistant professor in pathology at Yamaguchi University. He joined Shionogi & Co., Ltd. in 1966.Search for more papers by this authorH. Yamada, H. Yamada Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553, Japan Hideo Yamada is a research Asociate Director at Shionogi Research Laboratories. He received his Ph.D. in the field of pharmacy from Tokyo University, Japan, and did postdoctoral work at State University of New York at Buffalo. He was born in Aichi, Japan, in 1932 and entereed Shionogi & Co., Ltd. in 1957. His research interests include pharmacokinetics and biopharmaceutics of antibiotics and anticancer agents.Search for more papers by this author First published: Autumn (Fall) 1981 https://doi.org/10.1002/med.2610010302Citations: 20 AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL References 1 R. D. G. Cooper, in Topics in Antibiotic Chemistry, P. Sammes, Ed., Ellis Horwood, Chichester, 1979, Vol. 3, Part B. 2 F. A. Jung, W. R. Pilgrim, J. P. Poyser, and P. J. Siret, in Topics in Antibiotic Chemistry, P. G. Sammes, Ed., Ellis Horwood, Chichester, 1979, Vol. 4. 3 S. Wolfe, J. B. Ducep, K. C. Tin, and S. L. Lee, Can. J. Chem., 52, 3996 (1974). 4 L. D. Cama and B. G. Christensen, J. Am. Chem. Soc., 96, 7582 (1974). 5 R. A. Firestone, J. L. Fahey, N. S. Maciejewicz, G. Patel, and B. G. Christensen, J. Med. Chem., 20, 551 (1977). 6(a) E. G. Brain, C. L. Branch, A. J. Eglington, J. H. C. Nayler, N. F. Osborne, M. J. Pearson, T. C. Smale, R. Southgate, and P. Tolliday, in Recent Advances in the Chemistry of β-lactam Antibiotics, J. Elks, Ed., The Chemical Society, Burlington House. London, 1977, p. 204; (b) C. L. Branch and M. J. Pearson, J. Chem. Soc. Perkin Trans. 1, 2268 (1979). 7 M. Narisada, H. Onoue, and W. Nagata, Heterocycles, 7, 839 (1977). 8 M. Narisada, T. Yoshida, H. Onoue, M. Ohtani, T. Okada, T. Tsuji, I. Kikkawa, N. Haga, H. Satoh, H. Itani, and W. Nagata, J. Med. Chem., 22, 757 (1979). 9 S. Yamamoto, N. Haga, T. Aoki, S. Hayashi, H. Tanida, and W. Nagata, Heterocycles, 8, 283 (1977). 10 Y. Hamashima, S. Yamamoto, T. Kubota, T. Tokura, K. Ishikura, K. Minami, F. Matsubara, M. Yamaguchi, I. Kikkawa, and W. Nagata, Tetrahedron Lett., 4947 (1979). 11 H. Yanagisawa, M. Fukushima, A. Ando, and H. Nakao, Tetrahedron Lett., 2705 (1975). 12 T. Tsuji, T. Kataoka, M. Yoshioka, Y. Sendo, Y. Nishitani, T. Maeda, and W. Nagata, Tetrahedron Lett., 2793 (1979). 13 I. Kikkawa and T. Yorifuji, Synthesis, 877 (1980). 14 M. Yoshioka, I. Kikkawa, T. Tsuji, Y. Nishitani, S. Mori, K. Okada, M. Murakami, F. Matsubara, M. Yamaguchi, and W. Nagata, Tetrahedron Lett., 4287 (1979). 15 S. Uyeo, I. Kikkawa, Y. Hamashima, Y. Nishitani, H. Ona, K. Okada, T. Kubota, K. Ishikura, Y. Ide, K. Nakano, and W. Nagata, J. Am. Chem. Soc., 101, 4403 (1979). 16 Y. Sendo, and M. Yoshioka, J. Chem. Soc. Chem. Commun., 1069 (1980). 17 Y. Hamashima, S. Yamamoto, S. Uyeo, M. Yoshioka, M. Murakami, H. Ona, Y. Nishitani, and W. Nagata, Tetrahedron Lett., 2595 (1975). 18 M. Yoshioka, T. Tsuji, S. Uyeo, S. Yamamoto, T. Aoki, Y. Nishitani, S. Mori, H. Satoh, Y. Hamada, H. Ishitobi, and W. Nagata, Tetrahedron Lett., 21, 351 (1980). 19 G. V. Kaiser and S. Kukolja, in Cephalosporins and Penicillins, Chemistry and Biology, E. H. Flynn, Ed., Academic, New York, 1972, Chap. 3. 20 Y. Hamashima, H. Matsumura, S. Matsuura, W. Nagata, M. Narisada, and T. Yoshida, Chem. Soc. Spec. Publ., to appear. 21 T. Yoshida, Philos. Trans. R. Soc. London Ser. B, 289, 231 (1980). 22 M. Narisada and W. Nagata, German Offen. 2,713,370 (1977); Chem. Abstr., 88, 22936d (1978). 23 M. Narisada, T. Yoshida, S. Matsuura, H. Onoue, M. Ohtani, and W. Nagata, Abstracts of Papers, 100th Anniversary Meeting of Japan Pharmaceutical Society, Tokyo, April 1980. 24(a) M. Narisada, T. Tsuji, M. Yoshioka, H. Matsumura, Y. Hamashima, S. Hayashi, and W. Nagata, German Offen. 2,793,448 (1978); Chem. Abstr., 89, 6330s (1978); (b) W. Nagata, Y. Hamashima, T. Tsuji, and W. H. W. Lunn, German Offen. 2,831,092 (1972). 25 H. Matsumura, M. Narisada, T. Okada, N. Haga, T. Yano, and W. Nagata, Abstracts of Papers, 100th Anniversary Meeting of Japan Pharmaceutical Society, Tokyo, April 1980. 26 K. Murakami, M. Takasuka, K. Motokawa, and T. Yoshida, J. Med. Chem., 24, 88 (1980). 27 M. Gorman and C. W. Ryan, in Cephalosporins and Penicillins, Chemistry and Biology, E. H. Flyne, Ed., Academic, New York, 1972, p. 532. 28 W. Nagata, presented at the 17th National Medicinal Chemistry Symposium, Troy, NY, June 15–19, 1980. 29 M. Narisada, T. Yoshida, M. Ohtani, K. Ezumi, and K. Takasuka, Acta Crystallogr. B, 36, 3137 (1980). 30 M. Shiro, H. Nakai, H. Onoue, and M. Narisada, to appear. 31 K. Murakami and T. Yoshida, Abstracts of Papers, 100th Anniversary Meeting of Japan Pharmaceutical Society, Tokyo, April 1980. 32(a) M. Narisada and W. Nagata, U.S. Pat. 4,138,486 (1979); (b) M. Narisada and W. Nagata, U.S. Pat. 4,130,571 (1979); (c) M. Narisada and W. Nagata, U.S. Pat. 4,201,782 (1980); (d) Y. Hamashima, M. Narisada, S. Hayashi, and W. Nagata, U.S. Pat. 4,183,928 (1980). 33 Y. Hamashima, H. Matsumura, K. Ishikura, T. Yoshida, S. Matsuura, and W. Nagata, Abstracts of Papers, 100th Anniversary Meeting of Japan Pharmaceutical Society, Tokyo, April 1980. 34 W. Nagata, M. Narisada, and T. Yoshida, in β-lactam Antibiotics, Chemistry and Biology, R. B. Morin, and M. Gorman Eds., Academic, New York, to appear. 35 S. Hayashi, M. Narisada, F. Watanabe, and W. Nagata, Abstracts of Papers, 100th Anniversary Meeting of Japan Pharmaceutical Society, Tokyo, April 1980. 36 Y. Hamashima, H. Matsumura, K. Tokura, K. Minami, and T. Kubota, Abstracts of Papers, 100th Anniversary Meeting of Japan Pharmaceutical Society, Tokyo, April 1980. 37 T. Yoshida, S. Matsuura, M. Mayama, Y. Kameda, and S. Kuwahara, Antimicrob. Agents Chemother., 17, 302 (1980). 38 J. H. Jorgensen, S. A. Crawford, and G. A. Alexander, Antimicrob. Agents Chemother., 17, 901 (1980). 39 J. Kurihara, K. Katsumoto, Y. Uzuka, H. Shishido, T. Nagatake, H. Yamada, T. Yoshida, T. Oguma, Y. Kimura, and Y. Tochino, in Current Chemotherapy and Infections Disease, J. D. Nelson, and C. Grassi Eds., American Society of Microbiology, Washington, DC, 1980, Vol. I, p. 110. 40 H. C. Neu, N. Aswapokee, K. P. Fu, and P. Aswapokee, Antimicrob. Agents Chemother., 16, 141 (1979). 41 W. H. Hall, B. J. Opfer, and D. N. Gerding, Antimicrob. Agents Chemother., 17, 273 (1980). 42 G. M. Trager, G. White, V. M. Zimels, D. A. Bryk, and A. P. Panwalker, in Current Chemotherapy and Infectious Disease, J. D. Nelson, and C. Grassi Eds., American Society of Microbiology, Washington, DC, 1980, Vol. I, p. 96. 43 K. Sato, M. Inoue, and S. Mitsuhashi, Antimicrob. Agents Chemother., 17, 736 (1980). 44 Y. Komatsu and T. Nishikawa, Antimicrob. Agents Chemother., 17, 316 (1980). 45 S. Matsuura, T. Yoshida, K. Sugeno, Y. Harada, M. Harada, and S. Kuwahara, Eighteenth Interscience Conference on Antimicrobial Agents and Chemotherapy, Atlanta, GA, 1978, Abstract No. 152. 46 G. L. Brier, H. R. Black, R. S. Griffith, and J. D. Wolny, in Current Chemotherapy and Infectious Disease, J. D. Nelson, and C. Grassi Eds., American Society of Microbiology, Washington, DC, 1980, Vol. I, p. 62. 47 F. Kobayashi, H. Furukawa, Y. Harada, M. Hatano, and K. Ishimura, Chemotherapy (Tokyo), 28(S-7), 1002 (1980). 48 Y. Muraoka, I. Yahara, T. Yoshizaki, and Y. Harada, Chemotherapy (Tokyo), 28(S-7), 1072 (1980). 49 F. Kobayashi, H. Furukawa, N. Hasegawa, T. Yoshizaki, and Y. Harada, Chemotherapy (Tokyo), 28(S-7), 1007 (1980). 50 Y. Muraoka, F. Ito, T. Yoshizaki, and Y. Harada, Chemotherapy (Tokyo), 28(S-7), 1089 (1980). 51 F. Kobayashi, M. Matsuura, N. Hasegawa, T. Yoshizaki, and Y. Harada, Chemotherapy (Tokyo), 28(S-7), 1029 (1980). 52 Y. Muraoka, H. Hara, T. Yoshizaki, and Y. Harada, Jpn. J. Antibiot., to appear. 53 Y. Muraoka, T. Yoshizaki, and Y. Harada, Jpn. J. Antibiot. (Tokyo), to appear. 54 F. Kobayashi and K. Hara, Chemotherapy (Tokyo), 28(S-7), 1108 (1980). 55 Y. Hasegawa and T. Yoshida, Chemotherapy (Tokyo), 28(S-7), 1119 (1980). 56 F. Kobayashi and M. Ando, Chemotherapy (Tokyo), 28(S-7), 1142 (1980). 57 Y. Harada and K. Teshima, Chemotherapy (Tokyo), 28(S-7), 1202 (1980). 58 R. M. Atkinson, J. P. Currie, B. Davis, P. A. H. Pratt, H. M. Sharpe, and E. G. Tomich, Toxicol. Appl. Pharmacol., 8, 398 (1966). 59 M. Harada, M. Matsumoto, and M. Takeuchi, Chemotherapy (Tokyo), 28(S-7), 1191 (1980). 60 H. Yamada, T. Yoshida, T. Oguma, Y. Kimura, Y. Tochino, J. Kurihara, K. Matsumoto, Y. Uzuka, H. Shishido, and T. Nagatake, Chemotherapy (Tokyo), 28(S-7), 251 (1980). 61 J. N. Parsons, N. M. Ramamo, and M. E. Levison, Antimicrob. Agents Chemother., 17, 226 (1980). 62 K. S. Israel, H. R. Black, R. S. Griffith, G. L. Brier, and J. D. Walny, in Current Chemotherapy and Infectious Disease, J. D. Nelson, and C. Grassi Eds., American Society of Microbiology, Washington, DC, 1980, Vol. I, p. 107. 63 T. Yoshida, Y. Kimura, and Y. Tochino, Chemotherapy (Tokyo). 28(S-7), 194 (1980). 64 K. Sugeno, H. Okabe, H. Tanaka, and R. Norikura, Chemotherapy (Tokyo), 28(S-7), 207 (1980). 65 H. Nakamura, S. Hayashi, K. Seki, T. Fukuda, S. Aoyama, and S. Kurasawa, Chemotherapy (Tokyo), 28(S-7), 902 (1980). 66 J. Hondoh, S. Baba, K. Wada, T. Hatano, K. Murai, and Y. Suzuki, Chemotherapy (Tokyo) 28(S-7), 996 (1980). 67 S. H. Landesman, D. Cleri, R. Goetz, E. J. O. Goldstein, M. Lorrado, and F. Cherubin, Clin. Res., 27, 590A (1979). 68 J. Shimada, Y. Ueda, T. Yamaji, Y. Abe, and M. Nakamura, in Current Chemotherapy and Infectious Disease, J. D. Nelson, and C. Grassi Eds., American Society of Microbiology, Washington, DC, 1980, Vol. I, p. 109. 69 H. Tanimura, T. Sekiya, K. Miki, Y. Hikasa, M. Okamoto, T. Yasutomi, H. Kawaguchi, H. Matsumoto, H. Otani, H. Miyake, H. Awane, K. Fukuchi, Y. Takahashi, Y. Nishijima, S. Kido, T. Nishikawa, K. Nishikawa, M. Kurahashi, K. Konishi, R. Fujita, Y. Ueyama, Y. Naito, F. Rai, and H. Hashino, Chemotherapy (Tokyo), 28(S-7), 661 (1980). 70 N. Aoki, O. Sekine, Y. Usuda, Y. Yuasa, T. Shimizu, N. Wakabayashi, S. Hayashi, and K. Watanabe, Chemotherapy (Tokyo), 28(S-7), 361 (1980). Citing Literature Volume1, Issue3Autumn (Fall) 1981Pages 217-248 ReferencesRelatedInformation

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