Phenicol antibacterials

Patent metadata

Field	Value
Publication number	US-9073894-B2
Application number	US-201313785422-A
Country	US
Kind code	B2
Filing date	Mar 5, 2013
Priority date	Mar 6, 2012
Publication date	Jul 7, 2015
Grant date	Jul 7, 2015

Abstract

The present invention provides novel phenicol derivatives of formula I

their use for the treatment of infections in mammals, pharmaceutical composition containing these novel compounds, and methods for the preparation of these compounds.

First claim

We claim:

1. A compound of formula II

its enantiomers, diastereomers, or pharmaceutical acceptable salts or prodrugs thereof wherein:
W is —H or —PO(OH) 2 ; and
X and Y are each independently halo.

2. The compound of claim 1 selected from group consisting of:
N-((1R,2S)-1-(4-(6-((RS)-1-aminoethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide; and
(1R,2S)-1-(4-(6-(1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-difluoroacetamido)-3-fluoropropyl dihydrogen phosphate.

3. A compound which is N-((1R,2S)-1-(4-(64(RS)-1-aminoethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide.

4. A compound which is (1R,2S)-1-(4-(6-(1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-difluoroacetamido)-3-fluoropropyl dihydrogen phosphate.

5. The compound of claim 1 selected from the group consisting of:
N-((1R,2S)-1-(4-(6-(1-aminoethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide;
(1R,2S)-1-(4-(6-(1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-dichloroacetamido)-3-fluoropropyl hydrogen phosphate sodium;
(1R,2S)-1-(4-(6-(1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-dichloroacetamido)-3-fluoropropyl dihydrogen phosphate; and
(1R,2S)-1-(4-(6-(1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-difluoroacetamido)-3-fluoropropyl hydrogen phosphate sodium.

6. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

Assignees

• Zoetis Services Llc

Inventors

• Ewin Richard A
• Johnson Timothy Allan
• Sheehan Susan M K

Classifications

• C07D261/08

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D277/28

  Radicals substituted by nitrogen atoms · CPC title

• C07D413/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D213/40 Primary

  Acylated substituent nitrogen atom · CPC title

• C07D241/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title