Toyo Jozo Kabushiki Kaisha

Toyo Jozo Company, Ltd.

Sagami Chemical Research Center

Tadashiro Fujii

Naoki Muto

Masaru Otani

Satoshi Yaginuma

Mitsuo Hayashi

Nobuaki Nakagawa

Tetsu Saito

Shuzo Satoi

Masatoshi Tsujino

Kikuo Kotani

Susumu Watanabe

Kunio Matsumoto

Akira Kodama

Katsuyuki Ogura

Genichi Tsuchihashi

Masataka Morishita

Toshiharu Noda

Mitsuru Fukushima

Takao Hirano

Shigeo Katsuragi

Tetsuo Matsuda

Kiyofumi Fukukawa

Kunio Ohyama

Masaru Ono

Tooru Ueda

Jinnosuke Abe

Tetsuo Watanabe

Teruo Take

Kentaro Fujimoto

Kazuhiko Matsumoto

Kazuyoshi Nishiie

Masashi Kuramoto

Masao Yaso

Tsutomu Yamaguchi

Tsuneo Okuyama

Yuzo Shibuya

Seiji Katsumata

Neplanocin A derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or benzoyl, R.sub.3 is hydrogen or OR.sub.8, R.sub.5 is hydrogen or acetyl, R.sub.6 is hydrogen, acetyl or benzoyl, when R.sub.3 is hydrogen, R.sub.4 is hydrogen or halogen, hydroxy, acetoxy, acetylthio, amino or azide, and when R.sub.3 is OR.sub.8, R.sub.4 is hydrogen, R.sub.8 is hydrogen or acetyl, or R.sub.8 and R.sub.5 together form benzylidene, and at least one of R.sub.8, R.sub.5 and R.sub.6 is other than hydrogen. The compounds of the present invention have inhibitory action for the growth of L 5178 Y cells and have the same or superior activity as neplanocin A, and hence are useful as antitumor agents.

Neplanocin A derivatives

Antibiotic neplanocin A of the formula ##STR1## is produced by culturing Ampullariella sp. A 11079 FERM-P No. 4494 in a nutrient medium and then separating the neplanocin A thus produced from the culture medium.

Antibiotic neplanocin A

Novel amine compounds of the formula ##STR1## wherein R.sub.1 is lower alkyl and R.sub.2 is substituted methyl amino or D-amino acid residue, or a salt thereof. R.sub.1 can typically be isobutyl or methyl; and R.sub.2 can be methylamino of the formula

Assay method of enzyme activity

Aminoglycoside antibiotic G-367-2 believed to have the formula ##STR1## is produced by culturing Dactylosporangium thailandense G-367 FERM-P No. 4840 in a nutrient medium and separating the produced antibiotic therefrom. It has strong antibacterial effect against Gram negative bacteria.

Aminoglycoside antibiotic G-367-2

Neplanocin-B and -F of the formula ##STR1## in which Y is oxygen or a valence bond, are produced by culturing Ampullariella sp. A 11079 FERM-P No. 4494 in a nutrient medium and then separating the neplanocin-B and -F thus produced from the culture medium.

Neplanocin-B and -F

Aminoglycoside antibiotic G-367-1 believed to have the formulae ##STR1## is produced by culturing Dactylosporangium thailandense G-367 FERM-P No. 4840 in a nutrient medium and separating the produced antibiotic therefrom. It has strong antibacterial effect against Gram negative bacteria.

Aminoglycoside antibiotic G-367-1 and method for the production thereof

A novel microorganism species belonging to the genus Micromonospora, i.e. Micromonospora sp. A 11725 is found to be capable of producing novel macrolide antibiotics A 11725 I, A 11725 II and A 11725 III. Novel antibiotics A 11725 Ia and A 11725 IIa are also found to be derived by chemical modification of the antibiotics A 11725 I and A 11725 II, respectively. All of these antibiotics or salts thereof exhibit excellent antibacterial and anti-mycoplasmal activities against various microorganisms such as Staphylococcus or Mycoplasma, and therefore useful for various purposes including medicaments.

Novel macrolide antibiotics and preparation thereof

A group of sulfur-containing antibiotics, planothiocin-A, -B, -C, -D, -E, -F and -G, are produced by culturing Actinoplanes sp. A12526 in a nutrient medium, and separating the thus-produced planothiocins therefrom. The novel antibiotics have utility in therapeutic or prophylactic antibacterial compositions or feed additives for livestock, poultry or fish.

Antibiotic planothiocins

A polyfunctional disulfide compound, useful as a cross-linking reagent having S--S exchange reactivity, of the formula ##STR1## wherein R is 2-benzothiazolyl or 2-pyridyl-N-oxide and X is a spacer group having an alkylene group directly bonded to each S--S group.

Polyfunctional disulfide compounds having S--S exchange reactivity

A disulfide derivative, having S--S exchange reactivity, of the formula

Disulfide derivatives having S--S exchange reactivity

A disulfide compound of a carrier, having S--S exchange reactivity, of the formula

Disulfide compounds of a carrier, having S--S exchange reactivity

Cephalosporins having a sulfur-containing functional group of the formula ##STR1## present at the carbon atom directly bonded to the thienyl or furyl group in the side chain of the 7-position of cephem derivatives. These compounds are useful as anti-bacterial agents against Gram-positive and Gram-negative bacteria.

Cephalosporins having a sulfur containing functional group in the

7-Amino-cephem compounds are produced from 7-substituted-cephem compounds by the enzymatic action of microorganisms Comamonas sp. SY-77-1 FERM-P 2410 or Pseudomonas ovalis ATCC 950.

Process for the production of 7-amino-cephem compounds

Novel diacyl penicillins of the formula ##EQU1## wherein R is alkyl, cycloalkyl, aryl, aralkyl, phenoxyalkyl, heterocyclic carboxyl excepting isoxazole carboxyl derivatives, or ##SPC1## In which benzene ring A may optionally be substituted and B represents a protective group for the amino group, and X is a protective group for the carboxyl group, are produced by reacting a benzyl penicillin ester of the formula ##EQU2## wherein X is as defined above, with a chlorinating agent in the presence of tertiary organic base to obtain an imide chloride group-incorporated compound of the formula ##EQU3## and then reacting the compound of the last-named formula with carboxylate of the formula

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Mishima, Japan

Tadashiro Fujii