Meiji Seika Kaisha, Ltd.

Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

Meiji Seiki Kaisha, Ltd.

Eiichi Akita

Hamao Umezawa

Sumio Umezawa

Takeo Miyazawa

Yukio Horiuchi

Fumio Kai

Taro Niida

Shuntaro Yasuda

Shinichi Kondo

Takashi Tsuruoka

Shigeharu Inouye

Tsutomu Tsuchiya

Kunio Atsumi

Masao Koyama

Kiyoaki Katano

Ken Nishihata

Yujiro Yamada

Osamu Tsuchiya

Kuniomi Matsumoto

Keinosuke Miyauchi

Shunzo Fukatsu

Takahiro Ishii

Norio Ezaki

Shinji Miyadoh

Toshio Yoneta

Shoichi Amano

Yuzo Kazuno

Mitsugu Itoh

Triiodoallyl- or iodopropargyl-substituted tetrazole compounds which are prepared by reacting substituted tetrazole compound with reactive derivatives of corresponding triiodoallyl alcohol or iodopropargyl alcohol or by iodinating propargyltetrazole compounds, as well as antibacterial and antifungal compositions for medicinal, agricultural and industrial fields which contain as active ingredient said tetrazole compounds.

Iodoallyl and iodopropargyl substituted tetrazoles and anti-microbial

Triiodoallyl- or iodopropargyl-substituted heterocyclic aromatic compounds which can be prepared by reacting unsubstituted- or substituted nitrogen-containing heterocyclic compounds with corresponding iodine containing alcohol reactive derivatives in the presence of a base in an inert organic solvent. These new heterocyclic aromatic compounds have remarkable antibacterial and antifungal activities and are useful as antibacterial and antifungal agents in medicinal, agricultural and industrial fields.

Disclosed is a novel cephem compound represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Y are as defined in the specification, which is a useful intermediate for synthesizing various cephalosporin antibiotics having a methoxy group at the 7.alpha.-position thereof. Also disclosed is a process for preparing the same.

Cephem compounds and process for preparing the same

Disclosed is a novel cephem compound represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined in the specification, which is a useful intermediate for synthesizing various cephalosporin antibiotics having a methoxy group at the 7.alpha.-position thereof. Also disclosed is a process for preparing the same.

Process for preparing 7-.alpha.-methoxycephem compounds

A new polymeric compound, MF-300, is provided, which possesses a specific protective activity against bacterial infections caused particularly by Pseudomonas aeruginosa. The compound is derived from the reaction of ribostamycin with crotonoyl chloride followed by concentration of the reaction product and by subsequent recovery therefrom of a fraction having a range of molecular weights of 10,000.about.100,000 when measured by ultrafiltration method.

Polymeric compound, MF-300, with protective activity against bacterial

A new 1-N-(.omega.-aminoalkanesulfonyl) derivative of an aminoglycosidic antibiotic such as ribostamycin, 3'-deoxy- or 3',4'-dideoxy-ribostamycin, kanamycin A or B, and 3'-deoxy- or 3',4'-dideoxy-kanamycin B exhibits a broader, antibacterial spectrum than the parent aminoglycosidic antibiotic and is useful in the therapeutic treatment of infections caused by gram-positive and gram-negative bacteria including drug-resistant strains thereof. The aforesaid derivative may be made by reaction between the parent antibiotic and an amino-protected .omega.-aminoalkanesulfonic acid halide and removal of the amino-protecting group from the condensation product.

1-N-(.omega.-aminoalkanesulfonyl) derivative of aminoglycosidic

An antibiotic BN-200 substance produced by cultivating a BN-200 substance strain of the genus Erwinia and a process for producing the BN-200 substance.

Antibiotic BN-200 substance and process for production thereof

A process for preparing a novel antibiotic, 5'-amino-3',5'-dideoxy-ribostamycin, which comprises subjecting a ribostamycin derivative represented by the formula: ##STR1## to selective sulfonylation to form a 3',5'-O-disulfonyl derivative, SUBJECTING THE THUS PRODUCED DERIVATIVE TO AZIDE-FORMING REACTION WITH SODIUM AZIDE,

Pharmaceutical composition containing

3',4'-.alpha.-Epoxyneamine and its related aminoglycosidic antibiotic derivatives containing 3',4'-.alpha.-epoxyneamine moiety in the molecule thereof are now provided, which may be in the form of their amino-protected and partially hydroxyl-protected product and which are useful as intermediates for use in the synthetic production of therapeutically valuable 3'-deoxy derivatives of aminoglycosidic antibiotics.

3'-Epi-4'deoxykanamycin B

3'-Deoxy derivatives of neamine, 6'-N-alkylneamine, kanamycin B, 6'-N-alkylkanamycin B, ribostamycin, 6'-N-alkylribostamycin and paromamine may be produced by a new process comprising reducing the 3',4'-.alpha.-anhydro derivative (namely, the 3',4'-epoxide derivative) of the aminoglycosidic antibiotics with hydrogen in an alkaline lower alkanol medium containing an alkali metal hydroxide or alkoxide dissolved therein and in the presence of a reducing catalyst such as Raney nickel. The 3',4'-.alpha.-anhydro derivative may be prepared by treating the 3'-sulfonylated derivative of the amino-protected and hydroxyl-protected neamine, 6'-N-alkylneamine, kanamycin B, 6'-N-alkylkanamycin B, ribostamycin, 6'-N-alkylribostamycin or paromamine with an alkali metal hydroxide or alkoxide in a lower alkanol to effect epoxidation between the 4'-hydroxyl group and the carbon atom substituted by the 3'-sulfonic ester group.

Process for the synthetic production of 3-deoxy derivative of an

An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula: ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and amino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydrogen atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin produced is characterized by its useful activity inhibitory to the growth of bacteria resistant to the parent substance neamine or ribostamycin.

1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin

An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and maino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydroge atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin produced is characterized by its useful activity inhibitory to the growth of bacteria resistant to the parent substance neamine or ribostamycin.

Process of producing a 1-N-((S)-.alpha.-hydroxy-.omega.-aminoacyl)-3',4'-dideoxyneamine or -3',4'-dideoxyribostamycin, a useful semi-synthetic antibiotic in which the corresponding 6-O-((S)-.alpha.-hydroxy-.omega.-aminoacyl)-3',4'-dideoxyneamine or -3',4'-dideoxyribostamycine undergoes the acyl-migration reaction by treating with a basic medium.

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Yokohama, Japan

Eiichi Akita