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Claims for Patent: 4,943,569

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Claims for Patent: 4,943,569

Title: B-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)
Assignee: Sumitomo Pharmaceuticals Co., Ltd. (Osaka, JP)
Application Number:07/106,036
Patent Claims: 1. A .beta.-lactam compound represented by the formula: ##STR427## wherein R.sub.1 represents 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 an unsubstituted methylene group and Y represents a group of the formula (2): ##STR428## 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 alkenyl group having 3 to 4 carbon atoms, an aralkyl group having 1 to 3 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 or carbamoyl, or R.sub.5 and R.sub.6 are taken together to represent an alkylene chain or an alkylene chain via an oxygen atom, a sulfur atom or a (C.sub.1 -C.sub.3)alkyl-substituted nitrogen atom to form, together with the adjacent nitrogen atom, a 4- to 7-membered cyclic amino group, and a pharmaceutically acceptable salt thereof.

2. A .beta.-lactam compound represented by the formula: ##STR429## wherein R.sub.1 represents 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 substituted methylene group of the formula (1): ##STR430## wherein R.sub.4 represents an alkyl group having 1 to 3 carbon atoms; and Y represents a group of the formula (2): ##STR431## 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 3 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 or carbamoyl, or R.sub.5 and R.sub.6 are taken together to represent an alkylene chain or an alkylene chain via an oxygen atom, a sulfur atom or a (C.sub.1 -C.sub.3)-alkyl-substituted nitrogen atom to form, together with the adjacent nitrogen atom, a 4- to 7-membered cyclic amino group, and a pharmaceutically acceptable salt thereof.

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

4. A compound as claimed in claim 1 or 2, wherein R.sub.1 represents a 1-hydroxyethyl group, R.sub.2 and R.sub.3 each represents a hydrogen atom, and Y is a group represented by the formula (2-c): ##STR432## wherein R.sub.5-c and R.sub.6-c have either one of the following meanings: (1) R.sub.5-c represents an alkyl group having 1 to 4 carbon atoms which may be substituted with a carbamoyl group, or a hydroxyl group, and R.sub.6-c represents a hydrogen atom or has the same meaning as defined for R.sub.5-c ;

(2) R.sub.5-c and R.sub.6-c jointly represent an alkylene chain to form, together with the adjacent nitrogen atom, an unsubstituted 4- to 6-membered saturated cyclic amino group; and

(3) R.sub.5-c and R.sub.6-c jointly represent an alkylene chain via an oxygen atom or a (C.sub.1 -C.sub.3)alkyl-substituted nitrogen atom to form, together with the adjacent nitrogen atom, a 6-membered cyclic amino group.

5. A .beta.-lactam compound of the formula: ##STR433## wherein Y is chosen from the group consisting of ##STR434## and the pharmaceutically acceptable salts thereof.

6. A .beta.-lactam compound of the formula: ##STR435## wherein Y is selected from the group consisting of ##STR436##

7. A compound as claimed in claim 3, wherein Y is represented by the formula: ##STR437##

8. A compound as claimed in claim 2, 3, 4, or 7, wherein X represents ##STR438##

10. (5R)-3-[2-((1-Pyrrolidino)carbonyl)pyr rolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2- carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

11. (5R)-3-[2-((1-Azetidino)carbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl )-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

12. (5R)-3-[2-((2-Hydroxyethyl)methylamino carbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-3- ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

13. (5R)-3-[2- (1-Morpholinocarbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[ 3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

14. (5R)-3-[2-(1-N-Methyl piperazinocarbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2 ,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

15. (5S)-3-[2-Carbamoylpy rrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2 -carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

16. (5S)-3-[2-(Dimethylaminocarbonyl)pyrrolidin-4-ylthio]-4-methyl-6-(1-hyd roxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

17. (5S)-3-[2-((1-pyrrolidino)carbonyl)pyrrolidin-4- ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-c arboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

18. (5S)-3-[2-((1-Azatidino)carbonyl)pyrrolidin-4-ylthio]-4-methyl-6-(1-hyd roxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

19. (5S)-3-[2-((2-Hydroxyethyl)methylaminocarbonyl)p yrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-e ne-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

20. (5S)- 3-[2-(1-Morpholinocarbonyl)pyrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl) -1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

21. (5S)-3-[2-(1-N-Methylpiperazinocarbony l)pyrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept- 2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

22. (5S)-3-[2- Carbamoylpyrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2, 0]hept-2-ene-7-one-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.

23. 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 or claim 2 and at least one pharmaceutically acceptable inert carrier or diluent.

24. A method of treating a bacterial infection comprising administering an effective amount of a compound according to claim 1 or claim 2 as an antimicrobial agent.

25. A (5R)-compound of the compound as claimed in claim 1, 3, or 7, which is represented by the formula: ##STR439##

26. A (5S)-compound of the compound as claimed in claim 2, 3, or 7, which is represented by the formula: ##STR440##

27. A (5R,6S,8R)-compound of the compound as claimed in claim 22.

28. A (5S,6S,8R)-compound of the compound as claimed in claim 27.

29. A (5R,6S,8R)-compound of the compound as claimed in any one of claims 10, 11, 12, 13, 14 or 15.

30. A (5S,6S,8R)-compound of the compound as claimed in any one of claims 13, 17, 18, 19, 20, 21, or 22

31. A (5R,6S,8R,2'S,4'S)-compound of the compound as claimed in claim 22.

32. A (5S,6S,8R,2'S,4'S)-compound of the compound as claimed in claim 31.

33. A (5R,6S,8R,2'S,4'S)-compound of the compound as claimed in any one of claims 10, 11, 12, 13, 14 or 15.

34. A (5S,6S,8R,2'S,4'S)-compound of the compound as claimed in any one of claims 13, 17, 18, 19, 20, 21, or 22.

35. A .beta.-lactam compound of the formula: ##STR441## and the pharmaceutically acceptable salts thereof.

36. A .beta.-lactam compound of the formula: ##STR442## and the pharmaceutically acceptable salts thereof.

37. A .beta.-lactam compound of the formula: ##STR443## wherein Y is chosen from the group consisting of ##STR444## and the pharmaceutically acceptable salt thereof.

38. A (5S)-compound of the compound as claimed in claim 8, which is represented by the formula: ##STR445##

39. A (4R,5S,6S,8R,2'S,4'S)-compound of the compound as claimed in any one of claims 2, 8, 18, 19, 20, 21 or 22.
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