Phenicol antibacterials

Patent metadata

Field	Value
Publication number	US-9340564-B2
Application number	US-201514731650-A
Country	US
Kind code	B2
Filing date	Jun 5, 2015
Priority date	Mar 6, 2012
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The present invention provides novel phenicol derivatives, 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 method for controlling or treating infections in livestock by administering to an animal in need of a therapeutically effective amount of a compound of Formula II, its enantiomers, diastereomers, or pharmaceutically acceptable salts thereof

wherein W is —H or —PO(OH)2; and X and Y are each independently halo.

2. The method of claim 1 wherein X and Y are both fluoro.

3. The method of claim 1 wherein the livestock is cattle or swine.

4. The method of claim 3 wherein the livestock is cattle.

5. The method of claim 1 wherein the compound of Formula II is N-(1-(4-(6-(1- aminoethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxyprop an-2-yl)-2,2-difluoroacetamide, its enantiomers, diastereomers, or pharmaceutically acceptable salt thereof.

6. The method of claim 5 wherein the compound of Formula II is N-(( 1R,2S)-1-(4-(6-(RS)-1-aminoethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide or (1R,2S)-1-(4-(6-(RS)-1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-difluoroacetamido )-3-fluoropropyl dihydrogen phosphate.

7. The method of claim 6 wherein the compound of Formula II is N-(( 1R,2S)-1-(4-(6-((S)-1-aminoethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide or (1R,2S)-1-(4-(6-((S)-1- aminoethyl)pyridin-3-yl)phenyl)-2- (2,2-difluoroacetamido)-3-fluoropropyl dihydrogen phosphate.

8. The method of claim 1 wherein the compound of Formula II is selected from:
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;
(1R,2S)-1-(4- (6-(1-aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-difluoroacetamido)-3-fluoropropyl hydrogen phosphate sodium; and
(1R,2S)-1-(4-(6-(1- aminoethyl)pyridin-3-yl)phenyl)-2-(2,2-difluoroacetamido)-3-fluoropropyl dihydrogen phosphate.

9. The compound N4(1R,2S)-1-(4-(6-(1-aminocyclopropyl)pyridin-3-yl) phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide, its enantiomers, diastereomers, or a pharmaceutically acceptable salt thereof.

Assignees

• Zoetis Services Llc

Inventors

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

Classifications

• C07D241/12

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

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D413/06

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

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title