IP Library › Granted Patent US 9,145,355
Granted Patent B2
US 9,145,355 · App. 14/351,939 · Granted Sep 29, 2015

Phenicol antibacterials

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,145,355
App. No.
14/351,939
Granted
Sep 29, 2015
Kind
B2
Abstract

The present invention provides novel phenicol derivatives, their use for the treatment of infections in mammals, pharmaceutical compositions containing these novel compounds, and methods for the preparation of these compounds.

Claims (39)

1. A compound, which is:

b) 2,2-Dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-methylureido)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

c) N-((1R,2S)-1-(4′-(2-aminopropan-2-yl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

d) N-((1R,2S)-1-(4′-((R)-1-aminoethyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

e) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-(pyrrolidin-2-yl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

f) N-((1R,2S)-1-(4′-(azetidin-2-yl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

g) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-(4′-((3-fluoroazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-1-hydroxypropan-2-yl)acetamide,

h) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-((methylamino)methyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

i) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-hydroxyazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

j) 2,2-dichloro-N-((1R,2S)-1-(4′-((3-(dimethylamino)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)acetamide,

k) N-((1R,2S)-1-(4′-((3-(aminomethyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

l) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-methoxyazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

m) N-((1R,2S)-1-(4′-((3-acetamidoazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

n) N-((1R,2S)-1-(4′-((3-aminoazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

o) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-hydroxy-3-(trifluoromethyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

p) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-(trifluoromethyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

q) N-((1R,2S)-1-(4′-((3-(aminomethyl)-3-hydroxyazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

r) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((R)-1-(methylsulfonamido)-ethyl)biphenyl-4-yl)propan-2-yl)acetamide,

s) N-((1R,2S)-1-(4′-(1-aminocyclopropyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide, or

t) N-((1R,2S)-1-(3′-(1-aminocyclopropyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide.

2. A compound, which is:

a) 2,2-Dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-methylureido)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

b) N-((1R,2S)-1-(4′-(2-aminopropan-2-yl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

c) N-((1R,2S)-1-(4′-((R)-1-aminoethyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

d) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-(pyrrolidin-2-yl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

e) N-((1R,2S)-1-(4′-(azetidin-2-yl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

f) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-(4′-((3-fluoroazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-1-hydroxypropan-2-yl)acetamide,

g) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-((methylamino)methyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

h) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-hydroxyazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

i) 2,2-dichloro-N-((1R,2S)-1-(4′-((3-(dimethylamino)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)acetamide,

j) N-((1R,2S)-1-(4′-((3-(aminomethyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

k) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-methoxyazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

l) N-((1R,2S)-1-(4′-((3-acetamidoazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

m) N-((1R,2S)-1-(4′-((3-aminoazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

n) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-hydroxy-3-(trifluoromethyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

o) 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4′-((3-(trifluoromethyl)azetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)propan-2-yl)acetamide,

p) N-((1R,2S)-1-(4′-((3-(aminomethyl)-3-hydroxyazetidin-1-yl)methyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide,

q) N-((1R,2S)-1-(4′-(1-aminocyclopropyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide, or

r) N-((1R,2S)-1-(3′-(1-aminocyclopropyl)-[1,1′-biphenyl]-4-yl)-3-fluoro-1-hydroxypropan-2-yl)-2,2-dichloroacetamide.

Assignments (2)
ADDRESS CHANGE OF ASSIGNEE Recorded Jun 6, 2017
From: ZOETIS SERVICES LLC
To: ZOETIS SERVICES LLC
Reel/Frame 042698/0099 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 13, 2015
From: ZOETIS LLC
To: ZOETIS SERVICES LLC
Reel/Frame 035651/0817 →