Shionogi Company Limited

Shionogi Seiyaku Kabushiki Kaisha

Tadashi Irie

Yasuhiro Nishitani

Yutaka Nishino

Hiroshi Tanida

Hikaru Itani

Yuji Sendo

Makoto Kii

Imidazo&lsqb;4,5-b&rsqb;-pyridiniummethyl-containing cephem compounds having broad antibacterial spectrum activity

Imidazo&lsqb;4,5-b&rsqb;pyridiniummethyl-containing cephem compounds having broad antibacterial spectrum

A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; R.sup.2, R.sup.3 and R.sup.4 are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group, or R.sup.2 and R.sup.4, or R.sup.3 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X.sup.1 is hydrogen or a hydroxy protecting group; X.sup.2 is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y.sup.2 is hydrogen or an amino protecting group.

Intermediates for pyrrolidylthiocarbapenem derivative

The method for producing a sulfamide according to the present invention includes the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative. In one embodiment, the sulfamide is represented by Formula I, the alcohol is represented by Formula II, and the oxycarbonylsulfamide compound is represented by Formula III:

Production method for sulfamide

Pyrrolidylthiocarbapenem derivative

A compound of the formula ##STR1## wherein R.sup.1 is hydrogen or a protecting group; R.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.3 -C.sub.7 cycloalkyl; R.sup.3 is hydrogen, hydroxy, or amino; R.sup.4 is halogen; R.sup.5 and R.sup.6 each is identically or differently hydrogen or C.sub.1 -C.sub.3 alkyl; W is C.sub.1 -C.sub.3 alkylidene; X is N or C-Y; Y is hydrogen or halogen; or a pharmaceutically acceptable salt thereof, having a more potent antibacterial activity against G(+) and G(-) bacteria than known analogues, useful as antibacterial agents.

Pyridonecarboxylic acids and their anti-bacterial compositions

9,10-Dihydro-9,10-methanoanthracene N-oxide derivatives represented by the formula: ##STR1## wherein A represents a straight or branched C.sub.1 -C.sub.6 alkylene; R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.4 alkyl or phenyl-C.sub.1 -C.sub.4 alkyl, or ##STR2## represents the group ##STR3## and X represents methylene, hydroxymethylene, C.sub.1 -C.sub.4 alkyl ##STR4## or hydroxy-C.sub.1 -C.sub.4 alkyl ##STR5## and their pharmaceutically acceptable acid addition salts which are useful as anti-depressants, tranquilizers, or anti-epileptics.

9,10-Dihydro-9,10-methanoanthracene N-oxide derivatives

9,10-Dihydro-9,10-methanoanthracene N-oxide derivatives represented by the formula: ##STR1## wherein A represents a straight or branched C.sub.1 -C.sub.6 alkylene; R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.4 alkyl or phenyl-C.sub.1 -C.sub.4 alkyl, or ##STR2## represents the group ##STR3## and X represents methylene, hydroxymethylene, C.sub.1 -C.sub.4 ##STR4## or hydroxy-C.sub.1 -C.sub.4 ##STR5## and their pharmaceutically acceptable acid addition salts which are useful as anti-depressants, tranquilizers, or anti-epileptics.

Growing community of inventors

Osaka, Japan

Tadashi Irie