Antibacterial agents

• US 4,297,345 A
• Filed: 10/22/1979
• Issued: 10/27/1981
• Est. Priority Date: 04/14/1975
• Status: Expired due to Term

• Current Assignee: Beecham Group PLC (GSK plc)
• Original Assignee: Beecham Group PLC (GSK plc)
• Inventors: Howarth, Thomas T.
• Primary Examiner(s): Goldberg, Jerome D.
• Application Number:
  US06/087,030
• Time in Patent Office: 736 Days
• Field of Search: 424/114
• US Class Current: 424/114
• CPC Class Codes: A61K 31/43 Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula , e.g. penicillins, penems
• CPC Class Codes: A61K 31/545 Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: , e.g. cephalosporins, cefaclor, or cephalexine
• CPC Class Codes: C07D 503/00 Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
• CPC Class Codes: Y02A 50/30 Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The compounds of the formula: ##STR1## and salts and esters thereof are useful agents for the treatment of bacterial infections either alone or in combination with a penicillin or cephalosporin derivative. The preceding compounds may be prepared by the hydrogenation of a compound of the formula: ##STR2## wherein R is a hydrogen atom or an acyl group or a salt or ester thereof.

Claims

1. A pharmaceutical composition for treating bacterial infections in humans and animals which comprises a synergistically effective amount of a compound of the formula (III):

##STR19## or a pharmaceutically acceptable salt thereof, and an antibacterially effective amount of benzylpenicillin or the acetoxymethyl ester thereof, in combination with a pharmaceutically acceptable carrier, the weight ratio of said compound or pharmaceutically acceptable salt thereof to benzylpenicillin or said ester thereof being 20;

1 to 1;

5.

2. A composition according to claim 1 wherein the compound is in the form of a pharmaceutically acceptable salt wherein said salt is selected from the group consisting of the sodium, potassium, calcium, magnesium, ammonium, ephenamine, procaine and benzathine salts.

3. A composition according to claim 1 wherein the pharmaceutically acceptable salt is of the formula (IV) or (V):

##STR20##

4. A composition according to claim 3 wherein the salt is the sodium or potassium salt of compound (IV) or (V).

5. A composition according to claim 1 wherein the compound is in the form of a salt of the formula (VI) or (VII):

##STR21##

6. A composition according to claim 5 wherein the compound is in the form of the sodium salt of the compound (VI).

7. A composition according to claim 1 wherein the ratio is 10:

1 to 1;

3.

8. A composition according to claim 1 wherein the ratio 5:

1 to 1;

2.

9. A composition according to claim 1 wherein the ratio 3:

1 to 1;

1.

10. A method of treating bacterial infection in humans and animals which comprises administering to humans or animals in need thereof synergistically effective amount of a compound of the formula (III):

##STR22## or a pharmaceutically acceptable salt thereof, and an antibacterially effective amount of benzylpenicillin or the acetoxymethyl ester thereof, the weight ratio of said compound or pharmaceutically acceptable salt thereof and said benzylpenicillin or ester thereof being 20;

1 to 1;

5.

11. A method according to claim 10 wherein the compound is a pharmaceutically acceptable salt of the formula (IV) or (V):

##STR23##

12. A method according to claim 11 wherein the compound is a sodium or potassium salt.

13. A method according to claim 10 wherein the compound is a salt of the formula (VI) or (VII):

##STR24##

14. A method according to claim 13 wherein the compound is a sodium salt of the formula (VI).

15. A method according to claim 10 wherein the ratio is 10:

1 to 1;

3.

16. A method according to claim 10 wherein the ratio 5:

1 to 1;

2.

17. A method according to claim 10 wherein the ratio 3:

1 to 1;

1.