IP Library › Granted Patent US 9,428,528
Granted Patent B2
US 9,428,528 · App. 15/071,597 · Granted Aug 30, 2016

Phenicol antibacterials

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Quick Facts
Patent No.
US 9,428,528
App. No.
15/071,597
Granted
Aug 30, 2016
Kind
B2
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.

Claims (34)

1. A compound selected from the group consisting of:

N-((1R,2S)-1-(4-(6-(1-aminocyclopropyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide;

2,2-Difluoro-N-{(1S,2R)-1-fluoromethyl-2-hydroxy-2-[4-(6-pyrrolidin-2-yl-pyridin-3-yl)-phenyl]-ethyl}-acetamide;

2,2-dichloro-N-{(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-[4-(6-pyrrolidin-2-ylpyridin-3-yl)phenyl]-ethyl}acetamide

N-((1R,2S)-1-(4-(6-((S)-1-amino-2-hydroxyethyl)-pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide, its enantiomers, diastereomers, or a pharmaceutically acceptable salt thereof.

2. A compound selected from the group consisting of:

2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(methylsulfonamidomethyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(1-(methylsulfonyl)pyrrolidin-2-yl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(1-(methylsulfonamido)ethyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

2,2-difluoro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(methylsulfonamidomethyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

N-((1R,2S)-1-(4-(6-(2-aminopropan-2-yl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

N-((1R,2S)-1-(4-(2-(1-aminoethyl)thiazol-5-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

2,2-Difluoro-N-[(1R,2R)-1-fluoromethyl-2-(4-{6-[(3-fluoro-propylamino)-methyl]-pyridin-3-yl}-phenyl)-2-hydroxy-ethyl]-acetamide;

N-((1S,2R)-2-{4-[6-(1-Amino-2,2,2-trifluoro-ethyl)-pyridin-3-yl]-phenyl}-1-fluoromethyl-2-hydroxy-ethyl)-2,2-difluoro-acetamide;

2,2-Difluoro-N-((1S,2R)-1-fluoromethyl-2-hydroxy-2-{4-[6-(1-morpholin-4-yl-ethyl)-pyridin-3-yl]-phenyl}-ethyl)-acetamide;

2,2-Difluoro-N-((1S,2R)-1-fluoromethyl-2-hydroxy-2-{4-[6-(1-methylamino-ethyl)-pyridin-3-yl]-phenyl}-ethyl)-acetamide;

2,2-Difluoro-N-[(1S,2R)-2-(4-{6-[1-(2-fluoro-ethylamino)-ethyl]-pyridin-3-yl}-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-acetamide;

N-((1R,2S)-1-(4-(6-(3-aminooxetan-3-yl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

2,2-difluoro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(1-(methylsulfonamido)cyclopropyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

N-((1R,2S)-1-(4-(5-(1-aminoethyl)thiophen-2-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide;

2,2-difluoro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-((RS)-1-(methylsulfonamido)ethyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

2,2-difluoro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-(morpholin-3-yl)pyridin-3-yl)phenyl)propan-2-yl)acetamide;

N-((1R,2S)-1-(4-(6-(1-amino-2-methoxyethyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

N-((1S,2R)-2-{4-[6-(1-amino-2-cyano-ethyl)-pyridin-3-yl]-phenyl}-1-fluoromethyl-2-hydroxy-ethyl)-2,2-difluoro-acetamide;

N-((1R,2S)-1-(4-(6-(2-amino-1-hydroxypropan-2-yl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

N-((1R,2S)-1-(4-(2-(1-aminoethyl)thiazol-5-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide;

N-((1R,2S)-1-(4-(6-(1-aminopropyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

N-((1R,2S)-1-(4-(6-(amino(cyclopropyl)methyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide;

N-((1R,2S)-1-(4-(6-(1-amino-2-hydroxypropyl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide; and

N-((1R,2S)-1-(4-(6-(azetidin-2-yl)pyridin-3-yl)phenyl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-difluoroacetamide, its enantiomers, diastereomers, or a pharmaceutically acceptable salt thereof.

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

4. 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 claim 1 , enantiomers, diastereomers, or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound of claim 2 , enantiomers, diastereomers, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

6. 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 claim 2 enantiomers, diastereomers, or a pharmaceutically acceptable salt thereof.