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Details for Patent: 4,933,333

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Details for Patent: 4,933,333

Title: .beta.-lactam compounds
Abstract:Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.
Inventor(s): Sunagawa; Makoto (Osaka, JP), Matsumura; Haruki (Nara, JP), Inoue; Takaaki (Hyogo, JP), Fukasawa; Masatomo (Hyogo, JP), Kato; Masuhiro (Osaka, JP)
Assignee: Sumitomo Pharmaceuticals Co., Ltd. (Osaka, JP)
Filing Date:Oct 08, 1987
Application Number:07/106,035
Claims:1. A .beta.-lactam compound represented by the formula: ##STR386## wherein R.sub.1 represents a hydrogen atom, a 1-hydroxyethyl group or a 1-hydroxyethyl group in which the hydroxy group is protected with a protecting group for a hydroxy group; R.sub.2 represents a hydrogen atom or a protecting group for an amino group; R.sub.3 represents a hydrogen atom or a protecting group for a carboxyl group; X represents a sulfur atom; and Y represents a group of the formula (2): ##STR387## wherein R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aralkyl group having 1 to 2 carbon atoms in the alkyl moiety thereof, a substituted alkyl group having 1 to 4 carbon atoms wherein said substituent is selected from the group consisting of hydroxyl, di-(C.sub.1 -C.sub.3)-alkylamino, carbamoyl, or R.sub.5 and R.sub.6 are taken together to represent an alkylene chain to form, together with the adjacent nitrogen atom, a 4- to 7-membered cyclic amino group.

2. A (5R)-compound of the compound as claimed in any one of claims 1, which is represented by the formula: ##STR388##

4. (5R)-3-[2-((1-Pyrrolidino)carbonyl)pyrr olidin-4-ylthio-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-4-th ia-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

5. (5R)-3 -[2-Carbamoylpyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hep t-2-ene-7-one-4-thia-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

6. A (5R,6S,8R)-compound of the compound as claimed in claim 2.

7. A (5R,6S,8R)-compound of the compound as claimed in any one of claims 3 to 5.

8. A (5R,6S,8R,2'S,4'S)-compound of the compound as claimed in claim 2.

9. A (5R,6S,8R,2'S,4'S)-compound of the compound as claimed in any one of claims 3 to 5.

10. A compound as claimed in claim 1, wherein R.sub.1 represents a hydrogen atom or a 1-hydroxyethyl group, R.sub.2 and R.sub.3 each represents a hydrogen atom.

11. A compound as claimed in claim 1, wherein R.sub.1 represents a 1-hydroxyethyl group, R.sub.2 and R.sub.3 each represents a hydrogen atom.

12. A compound as claimed in claim 11, wherein Y is represented by the formula: ##STR389##

13. A pharmaceutical composition for antimicrobial use which comprises as an active ingredient a pharmaceutically effective amount of at least one of the compounds as claimed in claim 1 and at least one pharmaceutically acceptable inert carrier or diluent.

14. A method of treating a bacterial infection comprising administering an effective amount of a compound according to claim 1 as an antimicrobial agent.
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