Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

Meiji Seika Kaisha, Ltd.

Meiji Seika Pharma Co., Ltd.

Tetsuo Shitara

Masayuki Igarashi

Yoshiaki Takahashi

Sumio Umezawa

Tsutomu Tsuchiya

Tomio Takeuchi

Masa Hamada

Toshiaki Miyake

Hamao Umezawa

Shunzo Fukatsu

Shuichi Sakamoto

Yoshihiko Kobayashi

Yasushi Takagi

Kazuo Umezawa

Eijiro Umemura

Caprazene is provided which is the compound represented by the following formula (I) wherein Me stands for methyl group, and a 5&#x2033;-N-alkoxycarbonyl or 5&#x2033;-N-aralkyloxycarbonyl derivative thereof, and wherein said compound has theH-NMR andC-NMR data as set forth in Table 15.

Caprazene as a novel compound and derivatives thereof, and caprazol as a novel compound and derivatives thereof

Caprazene and caprazol could be synthesized by hydrolysis of a caprazamycin. There could be synthesized a caprazene-1'&#x2033;-amide derivative of the formula (II) and a caprazene-1&#x2032;&#x2033;-ester derivative of the formula (III) from caprazene. Further, there could be synthesized a caprazol-1&#x2032;&#x2033;-amide derivative of the formula (V) and a caprazol-1&#x2032;&#x2033;-amide-3&#x2032;&#x2033;-ester derivative and a caprazol-3&#x2032;&#x2033;-ester derivative, etc. from caprazol. Furthermore, an imidazolidinone derivative could be synthesized from the ring-opened product of the 1,4-diazepinone ring of caprazol. The novel caprazene derivative, novel caprazol derivative and novel imidazolidinone derivative now synthesized exhibit excellent antibacterial activities against a variety of bacteria, including acid-fast bacteria.

Caprazene as novel compound and derivatives thereof, and caprazol as novel compound and derivatives thereof

4-O-(aminoglycosyl)- or

As new compound are now provided ten compounds, namely 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}kanamycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-2',3'-dideoxykanamycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-2',3'-dideoxy-2'-fluorokan amycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-5-deoxy-5-fluorokanamycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-kanamycin B; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-3'-deoxykanamycin B; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-3',4'-dideoxykanamycin B; 1-N-{(2R,3R) -4-amino-3-fluoro-2-hydroxybutyryl}-5-deoxy-5-fluorokanamycin B; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-5,3'-dideoxy-5-fluorokanam ycin B; and 1-N{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-5,3',4'-trideoxy-5-fluoroka namycin B, which are all useful as antibacterial agent in the therapeutic treatment of bacterial infections.

1-n-(4-amino-3-fluoro-2-hydroxybutyryl)-kanamycins

New semi-synthetic antibiotics, 3'-epistreptomycin and 3'-epidihydrostreptomycin are now provided, which are useful as antibacterial agents. 3'-Epidihydrostreptomycin is produced by a process comprising hydrolyzing an appropriately N,O-protected 2',3'-N,O-carbonyl-3'-epidihydrostreptomycin which is prepared by skilled introduction of amino-protecting groups and hydroxyl-protecting groups of appropriately selected natures into dihydrostreptomycin and intermolecular condensation of a particular pair of amino-protecting and hydroxyl-protecting groups so introduced. 3'-Epistreptomycin is produced by a process comprising oxidizing the 3'-hydroxymethyl group of an appropriately N,O-protected 3'-epidihydrostreptomycin as prepared by skilled introduction of amino-protecting groups and hydroxyl-protecting groups of appropriately selected natures, and then removing the remaining protective groups from the resultant N,O-protected 3'-epistreptomycin obtained as the oxidation product.

3'-Epistreptomycin and its dihydro derivative, pharmaceutical

Growing community of inventors

Yokohama, Japan

Tetsuo Shitara