Antibacterial compounds

• US 10,633,366 B2
• Filed: 06/05/2017
• Issued: 04/28/2020
• Est. Priority Date: 06/08/2016
• Status: Active Grant

• Current Assignee: Aziende Chimiche Riunite Angelini Francesco Acraf SPA (Angelini Finanziaria SPA)
• Original Assignee: Aziende Chimiche Riunite Angelini Francesco Acraf SPA (Angelini Finanziaria SPA)
• Inventors: Ombrato, Rosella, Magaro, Gabriele, Garofalo, Barbara, Furlotti, Guido, Mangano, Giorgina, Capezzone De Joannon, Alessandra
• Primary Examiner(s): Rahmani, Niloofar
• Application Number:
  US16/307,410
• Publication Number:
  US 20190161472A1
• Time in Patent Office: 1,058 Days
• Field of Search: 549398, 546139
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 471/16 Peri-condensed systems
• CPC Class Codes: C07D 491/04 Ortho-condensed systems
• CPC Class Codes: C07D 491/052 the oxygen-containing ring being six-membered
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C07D 498/04 Ortho-condensed systems
• CPC Class Codes: C07D 513/04 Ortho-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

The present invention relates to novel antibacterial compounds (1) as defined below, pharmaceutical compositions containing them and their use as antimicrobials. A compound of formula (1): A-L₁-Y-L₂-R—B, wherein A is a cyclic group having one of the following formulae (I), (II) and (III), and wherein B is cyclic group having one of the following formulae (IV) to (IX).

Claims

1. A compound of formula (1):

A-L₁-Y-L₂-R—

B 

 

(1)

wherein

A is a cyclic group having the following formulae (I);

2. The compound according to claim 1, wherein R₁ is a halogen atom, a cyano group, or an alkoxy group having from 1 to 2 carbon atoms.

3. The compound according to claim 2, wherein R₁ is selected from the group consisting of a fluorine atom, a chlorine atom, a cyano group and a methoxy group.

4. The compound according to claim 1, wherein L₁ is a σ

bond or a methylene group (—

CH₂).

5. The compound according to claim 1, wherein L₂ is a σ

bond, a (C_1-3)alkylenyl group, NR′

″

group, —

NR′

″

—

(C_1-3)alkylenyl group, (C_1-3)alkylenyl-NR′

″

—

group, —

NR′

″

—

(C_1-3)alkylenyl-NR′

″

—

group, or (C_1-3)alkylenyl-NR′

″

—

(C_1-3)alkylenyl group, said group being optionally substituted with one or more hydroxy group.

6. The compound according to claim 5, wherein L₂ is a σ

bond, a (C_1-2)alkylenyl group, NR′

″

group, —

NR′

″

—

(C_1-2)alkylenyl group, (C_1-2)alkylenyl-NR″

′

—

group, —

NR′

″

—

(C_1-2)alkylenyl-NR′

″

—

group, or (C_1-2)alkylenyl-NR′

″

—

(C_1-2)alkylenyl group, said group being optionally substituted with one hydroxy group.

7. The compound according to claim 1, wherein R is a σ

bond or an aromatic heterocyclic ring having 5 members containing one or more nitrogen atoms, optionally substituted with CH₂CN or CN.

8. The compound according to claim 7, wherein R is a σ

bond, a 1H-imidazol-4-yl group, or a 1H-pyrrol-2-yl group, optionally substituted with CH₂CN or CN.

9. The compound according to claim 1, wherein A is a cyclic group having one of the following formulae:

10. The compound according to claim 1, wherein Y is a ring having one of the following formulae:

11. The compound according to claim 1, wherein B is a cyclic group having one of the following formulae:

12. A pharmaceutical composition, comprising at least one compound, salt thereof with a pharmaceutically acceptable organic or inorganic acid or with a pharmaceutically acceptable organic or inorganic base, enantiomer, quaternary ammonium salt, or N-oxide according to claim 1, and

at least one inert pharmaceutically acceptable excipient.

13. A method for treating a bacterial infection, comprising administering an effective amount of a compound, salt with a pharmaceutically acceptable organic or inorganic acid or with a pharmaceutically acceptable organic or inorganic base, enantiomer, quaternary ammonium salt, or N-oxide according to claim 1 to a patient in need thereof.

14. The method according to claim 13, wherein said bacterial infection is selected from the group consisting of a skin infection, a mucosal infection, a gynecological infection, a respiratory tract infection (RTI), a CNS infections, a gastro-intestinal infection, a bone infection, a cardiovascular infection, a sexually transmitted infection, and a urinary tract infection.

15. The compound according to claim 1, wherein Y is a ring having one of the following formulae:

16. The method of according to claim 13, wherein said bacterial infection is an E. coli infection or an S. aureus infection.

17. The method of according to claim 13, wherein said bacterial infection is an E. coli infection.

18. The method of according to claim 13, wherein said bacterial infection is an S. aureus infection.