Antibacterial agents

• US 7,655,648 B2
• Filed: 08/02/2005
• Issued: 02/02/2010
• Est. Priority Date: 08/02/2004
• Status: Expired due to Fees

• Current Assignee: Glaxo Group Limited (Glaxosmithkline Holdings Ltd.)
• Original Assignee: Glaxo Group Limited (Glaxosmithkline Holdings Ltd.)
• Inventors: Seefeld, Mark Andrew, Miller, William Henry
• Primary Examiner(s): HABTE, KAHSAY
• Application Number:
  US11/572,929
• Publication Number:
  US 20070244091A1
• Time in Patent Office: 1,645 Days
• Field of Search: 544/48, 514/224.2
• US Class Current: 514/224.2
• CPC Class Codes: A61K 31/397 having four-membered rings, e.g. azetidine
• CPC Class Codes: A61P 31/04 Antibacterial agents
• 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
• 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

Naphthalene, quinoline, quinoxaline and naphthyridine derivatives useful in the treatment of bacterial infections in mammals, particularly humans, are disclosed herein.

Claims

1. A compound of formula (I)

2. A compound or salt according to claim 1, wherein:

Z₁ and Z₄ are N; and

Z₃ is CR^1a.

3. A compound or salt according to claim 1, wherein:

R₁ is OCH₃.

4. A compound or salt according to claim 1, wherein R^1a is at each occurrence independently hydrogen;

halogen;

or cyano.

5. A compound or salt according to claim 2, wherein:

R^1a of Z₂, Z₃ and Z₅ are each hydrogen;

R^1a of Z₆ is hydrogen, fluorine or cyano; and

R₁ is OCH₃.

6. A compound or salt according to claim 5, wherein:

R₂ is hydrogen or hydroxy;

R₄ is hydrogen;

halogen;

hydroxy;

(C_1-6)alkyl;

or (C_1-6)alkoxy;

R₅ is hydrogen or (C_1-6)alkyl;

R₆ is hydrogen;

hydroxy;

halogen;

or (C_1-6)alkyl;

R₉ is hydrogen or (C_1-6)alkyl; and

U is CH₂;

SO₂;

or C(═

O).

7. A compound according to claim 1, wherein the compound is:

a) 6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-azetidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]thiazin-3(4H)-one

b) 6-({[(1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-azetidinyl)methyl]amino}methyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition comprising a compound or salt according to claim 1 and a pharmaceutically acceptable carrier.

9. A method of treating bacterial infections in mammals which comprises administering to a mammal in need thereof an effective amount of a compound or salt according to claim 1 wherein the bacterial infections are caused by gram positive organisms selected from the group consisting of Staphyloccocus auresu, Staphlyococcus epidemidis, Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecalis, Entermococcus faecium;

and gram negative organisms selected from the group consisting of Haemophilus influenza E. coli, and Moraxella catarrhaliz Ravasio.