Claims for Patent: 5,317,016
✉ Email this page to a colleague
Summary for Patent: 5,317,016
| Title: | Pyrrolidylthiocarbapenem derivative |
| Abstract: | 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. |
| Inventor(s): | Nishitani; Yasuhiro (Osaka, JP), Irie; Tadashi (Osaka, JP) |
| Assignee: | Shionogi Seiyaku Kabushiki Kaisha (Osaka, JP) |
| Application Number: | 07/929,961 |
| Patent Claims: |
1. A pyrrolidylthiocarbapenem derivative represented by Formula I: ##STR45## 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 sulfamide 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.
2. A pyrrolidylthiocarbapenem derivative according to claim 1, wherein R.sup.1 is methyl. 3. A pyrrolidylthiocarbapenem derivative according to claim 2, wherein R.sup.4 is hydrogen. 4. A pyrrolidylthiocarbapenem derivative according to claim 3, wherein X.sup.1 and Y.sup.2 are hydrogens and X.sup.2 is hydrogen or alkali metal. 5. A pyrrolidylthiocarbapenem derivative according to claim 4, wherein R.sup.2 and R.sup.3 are hydrogens; R.sup.2 is methyl and R.sup.3 are hydrogen; both R.sup.2 and R.sup.3 are methyl; or R.sup.2 is 2-hydroxyethyl, and R.sup.3 are hydrogen. 6. A pyrrolidylthiocarbapenem derivative according to claim 2, wherein R.sup.3 is hydrogen, and R.sup.2 and R.sup.4 are bonded to each other to form --CH.sub.2 --CH.sub.2 --. 7. A pyrrolidylthiocarbapenem derivative according to claim 2, wherein R.sup.3 is hydrogen, and R.sup.2 and R.sup.4 are bonded to each other to form --CH.sub.2 --CH.sub.2 --CH.sub.2 --. 8. A pyrrolidylthiocarbapenem derivative according to claim 1, wherein at least one group selected from the group consisting of R.sup.2, R.sup.3, R.sup.4 and Y.sup.2 is selected from the group consisting of t-butyloxy carbonyl, allyloxycarbonyl, p-nitrobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl and diazo. 9. A pyrrolidylthiocarbapenem derivative according to claim 1, wherein X.sup.1 is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl and t-butoxydimethylsilyl. 10. A pyrrolidylthiocarbapenem derivative according to claim 1, wherein X.sup.2 is selected from the group consisting of hydrogen, sodium potassium, t-butyl, allyl, p-nitrobenzyl, p-methoxybenzyl and diphenylmethyl. 11. A pyrrolidylthiocarbapenem derivative according to claim 1, wherein the pyrrolidine ring in Formula I has a configulation of (3S,5S). 12. An antibacterial agent comprising an effective amount of the pyrrolidylthiocarbapenem derivative of claim 1 as an active ingredient. 13. An antibacterial agent comprising an effective amount of the pyrrolidylthiocarbapenem derivative of claim 4 as an active ingredient. 14. An antibacterial agent comprising an effective amount of the pyrrolidylthiocarbapenem derivative of claim 5 as an active ingredient. 15. An antibacterial agent comprising an effective amount of the pyrrolidylthiocarbapenem derivative of claim 11 as an active ingredient. 16. A method for inhibiting growth of bacteria sensitive to the pyrrolidylthiocarbapenem derivative of claim 1 by allowing the sensitive bacterium to be in contact with an effective amount of the pyrrolidylthiocarbapenem derivative. |
