Carbapenem derivatives

1. A compound of formula (I):

or a pharmaceutically acceptable salt, ester, and/or prodrug thereof;

wherein

R 1 is hydrogen or a carboxyl protecting group;

R 2 is hydrogen or an amino-protecting group;

R 3 is hydrogen or lower alkyl; and

R 4 is phenyl or substituted phenyl;

wherein the substituted phenyl comprises one or more substituents selected from the group consisting of halogen; hydroxyl; carboxyl; amino; nitro; cyano; lower alkyl; substituted lower alkyl; lower alkoxy; substituted lower alkoxy; aminosulfonyl; lower alkylaminosulfonyl; and a combination thereof;

wherein the substituted lower alkyl and the substituted lower alkoxy each independently comprise one or more substituents selected from the group consisting of halogen; hydroxyl; carboxyl; amino; nitro; cyano; and a combination thereof.

2. A compound of formula (I):

or a pharmaceutically acceptable salt, ester, and/or prodrug thereof;

wherein

R 1 is a hydrogen atom or a carboxyl protecting group;

R 2 is a hydrogen atom or an amino-protecting group;

R 3 is a hydrogen atom or a lower alkyl; and

R 4 is a phenyl or substituted phenyl;

wherein the substituted phenyl comprises one or more substituents selected from the group consisting of sulfo; carbamoyl; lower alkyl; substituted lower alkyl; lower alkoxy; substituted lower alkoxy; lower alkylcarbonyl; substituted lower alkylcarbonyl; lower alkylcarbonyloxy; substituted lower alkylcarbonyloxy; lower alkylsulphonyl; substituted lower alkylsulphonyl; lower alkylamido; substituted lower alkylamido; lower alkylcarbamoyl; substituted lower alkylcarbamoyl; lower alkylsulphonamido; substituted lower alkylsulphonamido; and a combination thereof;

wherein the substituted lower alkyl and the substituted lower alkoxy each independently comprise one or more substituents selected from the group consisting of sulfo; aminosulphonyl; carbamoyl; and a combination thereof;

wherein the substituted lower alkylcarbonyl; the substituted lower alkylcarbonyloxy; the substituted lower alkylsulphonyl; the substituted lower alkylamido; the substituted lower alkylcarbamoyl; and the substituted lower alkylsulphonamido each independently comprise one or more substituents selected from the group consisting of halogen; hydroxyl; carboxyl; amino; nitro; cyano; sulfo; aminosulfonyl; carbamoyl; and a combination thereof.

3. A compound of formula (II):

or a pharmaceutically acceptable salt, ester, and/or prodrug thereof;

wherein

R 1 is a hydrogen atom or a carboxyl protecting group;

R 2 is a hydrogen atom or an amino-protecting group;

R 3 is a hydrogen atom or a lower alkyl; and

R 4 is a phenyl or substituted phenyl;

wherein the substituted phenyl comprises one or more substituents selected from the group consisting of sulfo; carbamoyl; lower alkyl; substituted lower alkyl; lower alkoxy; substituted lower alkoxy; lower alkylcarbonyl; substituted lower alkylcarbonyl; lower alkylcarbonyloxy; substituted lower alkylcarbonyloxy; lower alkylsulphonyl; substituted lower alkylsulphonyl; lower alkylamido; substituted lower alkylamido; lower alkylcarbamoyl; substituted lower alkylcarbamoyl; lower alkylsulphonamido; substituted lower alkylsulphonamido; and a combination thereof;

wherein the substituted lower alkyl and the substituted lower alkoxy each independently comprise one or more substituents selected from the group consisting of sulfo; aminosulphonyl; carbamoyl; and a combination thereof;

wherein the substituted lower alkylcarbonyl; the substituted lower alkylcarbonyloxy; the substituted lower alkylsulphonyl; the substituted lower alkylamido; the substituted lower alkylcarbamoyl; and the substituted lower alkylsulphonamido each independently comprise one or more substituents selected from the group consisting of halogen; hydroxyl; carboxyl; amino; nitro; cyano; sulfo; aminosulfonyl; carbamoyl; and a combination thereof.

4. The compound of any of claims 1 to 3 , wherein

R 3 is hydrogen, methyl, ethyl, or propyl;

R 4 is a phenyl or substituted phenyl;

wherein the substituted phenyl comprises one or more substituents selected from the group consisting of halogen; hydroxyl; carboxyl; amino; lower alkyl; substituted lower alkyl; lower alkoxy; substituted lower alkoxy; aminosulfonyl; and a combination thereof;

wherein the substituted lower alkyl and the substituted lower alkoxy each independently comprise one or more substituents selected from the group consisting of halogen; hydroxyl; carboxyl; amino; and a combination thereof.

5. The compound of any of claims 1 to 3 , wherein

R 1 represents hydrogen atom;

R 2 represents hydrogen atom;

R 3 represents hydrogen atom or methyl;

R 4 is a phenyl or substituted phenyl;

wherein the substituted phenyl comprises one or more substituents selected from the group consisting of methyl; ethyl; carboxyl; carboxymethyl; carboxyethyl; methoxy; trifluoromethoxy; aminosulfonyl; and a combination thereof.

6. The compound of any of claims 1 to 3 , which is selected from the group consisting of

or a pharmaceutically acceptable salt, ester, and/or prodrug thereof.

7. The compound of any of claims 1 to 3 , wherein the pharmaceutically acceptable salt is an amino acid salt, or an inorganic base salt.

8. The compound of any of claims 1 to 3 , wherein the pharmaceutically acceptable ester is hydrolyzable to the corresponding carboxylic acid in vivo.

9. A pharmaceutical composition comprising a compound of any of claims 1 to 3 , or a pharmaceutically acceptable salt, ester, and/or prodrug thereof; and one or more pharmaceutically acceptable carriers.

10. A method of treating a bacterial infection in a patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound of any of claims 1 to 3 , or a pharmaceutically acceptable salt, ester, and/or prodrug thereof.