Takeda Chemical Industries, Inc.

Kouichi Yoshioka

Kentaro Hiraga

Michihiko Ochiai

Yasuhiko Kawano

Tetsuya Okutani

Tsunehiko Asako

Akira Morimoto

Giichi Goto

Hideaki Natsugari

Setsuo Harada

Hirotomo Masuya

Tohru Sugawara

Michio Masuoka

Ryo Nakayama

The compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, amino, isonitrile or an organic residue bonded through nitrogen; R.sup.2 is carboxy or a group derivable therefrom; X is hydrogen, methoxy, formylamino, alkyl which may be substituted, alkylthio in which the sulfur atom may be oxidized or azido, or forms a double bond together with the adjacent carbon atom; provided that when R.sup.1 is acetylamino or amino and X is hydrogen, R.sup.2 is not para-nitrobenzyloxycarbonyl or benzhydryloxycarbonyl, or a pharmaceutically acceptable salt thereof, exhibit excellent antimicrobial activity, and are utilized as antimicrobial agents.

Antibiotic derivatives, their production and use

A compound represented by formula (I): ##STR1## wherein R.sup.1 is an organic residue through a carbon atom,

Gamma-lactonecarboxylic acid derivatives and their use as antibacterial

The compound represented by the formula: ##STR1## where R.sup.1 stands for amino or an organic residue bonded through nitrogen; R.sup.2 stands for carboxyl or a group derivable therefrom; R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently stand for hydrogen or an organic residue, including the case where R.sup.5 or R.sup.6 forms a chemical bond or a ring with R.sup.7 or R.sup.8 ; X stands for hydrogen, methoxy or formylamino; or a salt thereof, produceable by the present method, exhibits excellent antimicrobial activity, and is utilized as antimicrobial agents.

Antibiotic

Optically active .beta.-lactams of the general formula ##STR1## wherein R.sup.1 is an amino or protected amino group, R.sup.2 is an organic residue bonding through a carbon atom thereof and R.sup.3 is the residue remaining after removal of the .alpha.-amino group from an optically active .alpha.-amino acid or a derivative thereof as well as a method of producing the same.

Optically active .beta.-lactams and method of their production

Method of producing 2-azetidinone-1-sulfonic acid compounds

Dehydroxylation of aminoglycoside antibiotics is carried out by halogenation of phosphorylated aminoglycoside antibiotics followed by reduction of thus halogenated antibiotics. The dehydroxylation process is entirely new and gives the final product in a high yield. The resulting deoxyaminoglycoside antibiotics are effective against microorganisms including aminoglycoside antiobiotics-resistant microorganisms.

Dehydroxylation of aminosugars

Deoxyaminoglycoside antibiotics are prepared in a high yield from phosphorylated aminoglycosides by reacting a phosphorylated aminoglycoside (a) with a silylating agent, or (b) successively with (i) a silylating or acylating agent and (ii) a halogenating agent; then subjecting thus obtained intermediate to reduction. Deoxyaminoglycoside antibiotics are useful for treating infections caused by microorganisms which are resistant or non-resistant to the corresponding aminoglycoside antibiotics.

Epiminodeaminodeoxyaminoglycoside antibiotics and intermediates

Novel steroid compounds are provided represented by the formula: ##SPC1## Wherein each of R.sup.1 and R.sup.2 represents hydrogen or methyl group or R.sup.1 and R.sup.2 may be combined with each other to represent methylene group, n is 2 or 3 and the dotted line means a double bond at 6-exo-position when n is 2 or between 6- and 7-position when n is 3. These novel compounds show a strong anti-androgenic activity, especially by oral administration, and can be used as a remedy for the prostatomegaly.

Growing community of inventors

Kyoto, Japan

Kouichi Yoshioka