Salts, prodrugs and polymorphs of fab i inhibitors

Abstract

In part, the present invention is directed to antibacterial compounds and salts thereof.

1 . A compound of formula I: 
       
         
           
           
               
               
           
         
       
       wherein
 n is a fractional or whole number between about 1 and about 1.5 inclusive; 
 m is a fractional or whole number between about 0 and about 3 inclusive; 
 X is selected from the group consisting of H 2 SO 4 , HSO 3 R′, HSO 3 Ar, H 3 PO 4 , HCl, HBr, CF 3 CO 2 H, and Cl 3 CO 2 H; 
 R′ is alkyl; and 
 Ar is aryl. 
 
     
     
         2 . The compound of  claim 1 , wherein the compound is in a crystalline form. 
     
     
         3 . The compound of  claim 1 , wherein n equals 1, m equals 1 and X is HSO 3 Ar. 
     
     
         4 . The compound of  claim 1 , wherein n equals 1, m equals 0 and X is HSO 3 Ar. 
     
     
         5 . The compound of  claim 1 , wherein Ar is benzene or toluene. 
     
     
         6 . The compound of  claim 1 , wherein the compound is an anhydrous p-toluenesulfonic salt. 
     
     
         7 . The salt according to  claim 6  with characteristic peaks in the powder X-ray diffraction pattern at values of 2θ as depicted in  FIG. 13 . 
     
     
         8 . The compound of  claim 1 , wherein the compound is a mono, di, tri or fractional hydrate form of a p-toluenesulfonic salt. 
     
     
         9 . The salt of  claim 8 , wherein the monohydrate form has characteristic peaks in the powder X-ray diffraction pattern at values of 20 substantially the same as depicted in  FIG. 12 . 
     
     
         10 . The compound of  claim 1 , wherein the compound is a hydrochloric acid salt. 
     
     
         11 . The salt of  claim 10 , wherein said salt has a powder X-ray diffraction pattern substantially that same as that depicted in  FIG. 3A . 
     
     
         12 . The compound of  claim 1 , wherein the compound is a methane sulfonate salt. 
     
     
         13 . The salt of  claim 12 , wherein said salt has a powder X-ray diffraction pattern substantially that same as that depicted in  FIG. 4 . 
     
     
         14 . The compound of  claim 1 , wherein the compound is a benzenesulfonic salt. 
     
     
         15 . The salt according to  claim 14 , wherein said salt has a powder X-ray diffraction pattern substantially that same as that depicted in  FIG. 5 . 
     
     
         16 . The salt according to  claim 15 , wherein said salt has a powder X-ray diffraction pattern substantially that same as that depicted in  FIG. 6 . 
     
     
         17 . The compound of  claim 1 , wherein the compound is a sulfate salt. 
     
     
         18 . The salt according to  claim 17 , wherein said salt has a powder X-ray diffraction pattern substantially that same as that depicted in  FIG. 8 . 
     
     
         19 . A compound selected from the group consisting of:
 (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide hydrochloride;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide hydrobromide;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide sulfate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide methane sulfonate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide ethane sulfonate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 2-hydroxyethanesulfonate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 4-methylbenzenesulfonate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 4-methylbenzenesulfonate monohydrate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide benzenesulfonate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide phosphate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide trifluoroacetate;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide trichloroacetate;   (E)-6-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-ylphosphonic acid;   Calcium (E)-6-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-ylphosphonate;   Magnesium (E)-6-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-ylphosphonate;   Disodium (E)-6-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-ylphosphonate;   Dipotassium (E)-6-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-2-oxo-3,4-dihydro-1,8-naphthyridin-1(2H)-ylphosphonate.   
     
     
         20 . (canceled) 
     
     
         21 . A composition comprising the compound of  claim 1  and a pharmaceutically acceptable excipient. 
     
     
         22 .- 28 . (canceled) 
     
     
         29 . A method of treating a subject with a bacterial illness comprising administering to the subject the pharmaceutical composition of  claim 21 . 
     
     
         30 .- 33 . (canceled) 
     
     
         34 . A method of disinfecting an inanimate surface comprising administering to the inanimate surface a compound of  claim 1 . 
     
     
         35 .- 42 . (canceled)