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J-GLOBAL ID：200902225618926994   Reference number：03A0470959

Synthesis and Structure-activity Relationships of Novel Parenteral Carbapenems, CS-023 (R-115685) and Related Compounds Containing an Amidine Moiety

新規非経口カルバペネム類,CS-023(R-115685)およびアミジン分子含有関連化合物の合成と構造-活性相関

Author (9)： KAWAMOTO I (Sankyo Co., Ltd., Tokyo, JPN) ,  SHIMOJI Y (Sankyo Co., Ltd., Tokyo, JPN) ,  KANNO O (Sankyo Co., Ltd., Tokyo, JPN) ,  KOJIMA K (Sankyo Co., Ltd., Tokyo, JPN) ,  ISHIKAWA K (Sankyo Co., Ltd., Tokyo, JPN) ,  MATSUYAMA E (Sankyo Co., Ltd., Tokyo, JPN) ,  ASHIDA Y (Sankyo Co., Ltd., Tokyo, JPN) ,  SHIBAYAMA T (Sankyo Co., Ltd., Tokyo, JPN) ,  OHYA S (Sankyo Co., Ltd., Tokyo, JPN)
Material： Journal of Antibiotics  (J Antibiot)
Volume： 56  Issue： 6  Page： 565-579  Publication year： Jun. 25, 2003 
JST Material Number： G0489A  ISSN： 0021-8820  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *carbapenem antibiotics ,...

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JST classification (2)： Synthesis of antibiotics  (GX04000Z) ,  Structure-activity relationship of drugs  (GV01050B)

Substance index (29)： Imipenem ,  Meropenem ,  4-Hydroxyproline ,  (4R,5S,6S)-3-(Diphenoxyphosphinyloxy)-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid 4-nitrobenzyl ester ,  CS-023 ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-(Iminomethyl)amino-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[(1-Iminoethyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[[N-(1-Iminoethyl)amino]methyl]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-Guanidino-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-(Guanidinomethyl)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-(2-Guanidinoethyl)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-(3-Guanidinopropyl)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[N-(1-Iminoethyl)aminoacetylamino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[(Guanidinoacetyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[[(2R)-2-Guanidinopropanoyl]amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[[(2S)-2-Guanidinopropanoyl]amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[(3-Guanidinopropanoyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[(4-Guanidinobutanoyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[N-Methyl-N-(guanidinoacetyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[(3-Methylguanidinoacetyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-2-[[(3S)-3-[N-Methyl-N-(3-methylguanidinoacetyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-(iminomethylamino)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-[(1-iminoethyl)amino]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-[[(1-iminoethyl)amino]methyl]-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-guanidino-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-(guanidinomethyl)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-(2-guanidinoethyl)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (4R,5S,6S)-3-[[(2S,4S)-1-Methyl-2-[[(3S)-3-(3-guanidinopropyl)-1-pyrrolidinyl]carbonyl]-4-pyrrolidinyl]thio]-4-methyl-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid ,  (3S)-3-Aminopyrrolidine

Reference (33)：

• 1) 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
• 2) BIRNBAUM, J.; F. M. KAHAN, H. KROPP & J. S. MACDONALD: Carbapenems, a new class of beta-lactam antibiotics: Discovery and development of imipenem/cilastatin. Am. J. Med. 78 (Suppl. 6A): 3-21, 1985
• 3) 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
• 4) INOUE, K.; Y. HAMANA & S. MITSUHASHI: Antibacterial activity of panipenem, a new carbapenem antibiotic. Chemotherapy (Tokyo) 39 (Suppl. 3): 1-13, 1991
• 5) NAGANUMA, H.; H. TOKIWA, Y. HIROUCHI, Y. KAWAHARA, J. FUKUSHIGE, M. FUKAMI, K. HIROTA, S. MURAMATSU, H. TAKAHAGI, K. INUI, Y. TANIGAWARA, M. YASUHARA, R. HORI & S. KUWAHARA: Nephroprotective effect and its mechanism of betamipron (1): Relationships of renal transport. Chemotherapy 39 (Suppl. 3): 166-177, 1991

Terms in the title (7)： カルバペネム類 ,  CS-023 ,  R-115685 ,  アミジン ,  分子 ,  関連化合物 ,  構造-活性相関