Sanraku-ocean Co., Ltd.

Sanraku Incorporated

Yasuo Fukagawa

Tomoyuki Ishikura

Takeo Yoshioka

Kageaki Kouno

Azuma Watanabe

Rokuro Okamoto

Yasutaka Shimauchi

Mitsuyasu Okabe

Noritaka Chida

Norio Shibamoto

Kazuhiko Okamura

Yasushi Okumura

Joseph Lein

Katsuro Kubo

Shoji Hirata

Hiroshi Tone

Kaichiro Kominato

Kenichi Yamamoto

Machiko Watanabe

Kohki Kiyoshima

Hiroyuki Chiba

A compound represented by the formula ##STR1## wherein R.sub.1 represents a lower alkyl group or a lower haloalkyl group; R.sub.2 represents a lower alkyl group, a lower haloalkyl group, an aralkyl group, or a group of the formula --COOR.sub.4 or --SO.sub.2 R.sub.5 in which R.sub.4 represents an aralkyl group or a substituted or unsubstituted alkyl group and R.sub.5 represents an alkyl group or a substituted or unsubstituted aryl group; and R.sub.3 represents a hydrogen atom or a carboxyl protecting group which can be easily split off. This compound is useful in the production of a 6-(disubstituted amino)carbapenem-series antibiotic. The compounds of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as defined above are important intermediates for the synthesis of the compounds of formula (I) and/or the aforesaid di-(substituted amino) carbapenem-series antibiotics.

6-(disubstituted amino)carbapenem compounds

Optically active azetidinones

Tylosin derivatives represented by the following general formula (I): ##STR1## [wherein R denotes a hydrogen atom, acetyl, propionyl or a radical of Si(R.sup.2).sub.3 (in which R.sup.2 is a lower alkyl group), and R.sup.1 stands for a hydrogen atom or a radical of Si(R.sup.2 .sub.3 ] are useful as intermediates for the synthesis of 4'-acyl derivatives of tylosin because, after introduction of any desired acyl group at the 4'-hydroxyl group, the silyl protective group can be readily removed without liberation of the acyl group. This invention also provides processes for producing the tylosin derivatives. More specifically, it provides a melthod of selectively protecting 2'- and 4''-hydroxyl groups of tylosin (those of higher reactivity among the hydroxyl groups involved); a method of selectively protecting only the 4''-hydroxyl group of tylosin; a method of selectively protecting the 3- and 4''-hydroxyl groups of 2'-O-acyltylosin; and a method of protecting 3-, 2'- and 4''-hydroxyl groups of tylosin.

Tylosin derivatives and processes for producing the same

Compounds represented by formula ##STR1## wherein Y.sup.1 and Y.sup.2 are identical or different, and respectively denote benzoylamino groups or phthalimide groups. This compound is useful for inhibition of dipeptidase.

Aminoethylcysteine derivatives

A compound represented by the formula ##STR1## wherein R.sub.1 represents a lower alkyl group or a lower haloalkyl group; R.sub.2 represents a lower alkyl group, a lower haloalkyl group, an aralkyl group, or a group of the formula --COOR.sub.4 or --SO.sub.2 R.sub.5 in which R.sub.4 represents an alkyl group or a substituted or unsubstituted aralkyl group and R.sub.5 represents an alkyl group or a substituted or unsubstituted aryl group; and R.sub.3 represents a hydrogen atom or a carboxyl protecting group which can be easily split off. This compound is useful in the production of a 6-(disubstituted amino)carbapenem-series antibiotic.

6-(disubstituted amino)carbapenam compounds

An azetidinone derivative of the formula ##STR1## wherein R.sub.1 represents a formyl group, a carboxyl group, an acetyloxy group or a group of the formula ##STR2## in which R.sub.2 and R.sub.3 each represent a lower alkyl group or together represent a lower alkylene group, and Z represents a hydrogen atom or an amino-protecting group.

3-(CHFCH.sub.3)-azetidinone intermediates

An aminocarboxylic acid derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a hydrogen atom or an alkyl group which may have a substituent, and Y represents --NH-- or --S--, provided that when Y represents --NH--, at least one of R.sub.1 and R.sub.2 represents an alkyl group which may have a substituent. These compounds have excellent inhibitory activity on dipeptidase in animals, and are useful for administration in combination with carbapenem antibiotics.

Aminocarboxylic acid derivatives

A compound represented by the following formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a hydroxyl group, R.sub.2 represents a group of the formula --CH.sub.2 NO.sub.2, --CN.fwdarw.O or ##STR2## in which A represents a group of the formula ##STR3## in which R.sub.4 represents a hydrogen atom or an alkoxycarbonyl group, R.sub.5 represents a phenyl, alkoxycarbonyl or alkanoyloxymethyl group, R.sub.6 represents an alkyl group and R.sub.7 represents a phenyl, naphthyl, pyridyl, furyl or thienyl group; and R.sub.3 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group, and a process for production thereof.

.beta.-Lactam derivatives and process for production thereof

Novel phosphoric ester of antibiotic OA-6129 presented by the formula ##STR1## wherein R is a hydrogen atom, hydroxyl or hydroxysulfonyloxy, and its salts and the preparation method thereof.

Phosphoric ester of antibiotic OA-6129

A compound represented by the following formula ##STR1## wherein R represents a hydrogen atom or a methyl group,

Antibiotics and process for production thereof

A novel enzyme, amidohydrolase, having the ability to depantothenylate antibiotic OA-6129A represented by the following formula ##STR1## but no substantial ability to deacetylate antibiotic PS-5 represented by the following formula ##STR2##

Amidohydrolase having ability to depantothenylate an antibiotic

A compound of the formula ##STR1## wherein R.sub.1 represents a hydrogen atom, --OH or --OSO.sub.3 H, and R.sub.2 represents a hydrogen atom or an unsubstituted or substituted benzyl group; and a salt thereof; processes for production thereof by fermentation; and uses thereof as antimicrobial agents.

Novel .beta.-lactam compounds, process for producing thereof, and use

A novel antibiotic substance of the formula ##STR1## wherein R.sub.1 is CH.sub.3 and R.sub.2 is --CH.sub.2 --CH.sub.2 -- or R.sub.1 is H and R.sub.2 is --CH.dbd.CH--; and R.sub.3 represents hydrogen, lower alkyl or triphenylmethyl, and including the salts of the compound of formula (I) wherein R.sub.3 is hydrogen, said antibiotic substance having strong antibiotic activity and .beta.-lactamase inhibiting effect, and a method for producing the same by aerobic cultivation of Streptomyces A271.

Antibiotics and derivatives thereof having .beta.-lactamase inhibitory

A novel antibiotic substance and derivatives thereof, having strong antibiotic activity and .beta.-lactamase inhibiting effect and a method for producing the same by aerobic cultivation of Streptomyces A 271.

Growing community of inventors

Kamakura, Japan

Yasuo Fukagawa