IP Library › Granted Patent US 8,796,257
Granted Patent B2
US 8,796,257 · App. 13/690,398 · Granted Aug 5, 2014

Bicyclic compounds and their use as antibacterial agents and β-lactamase inhibitors

Inventors: Samarendra N. Maiti (Edmonton, CA); Dai Nguyen (Edmonton, CA); Jehangir Khan (Edmonton, CA); Rong Ling (Edmonton, CA)
Assignee: Naeja Pharmaceutical Inc.
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 8,796,257
App. No.
13/690,398
Granted
Aug 5, 2014
Kind
B2
Abstract

A compound of formula (I): wherein: M is hydrogen or a pharmaceutically acceptable salt-forming cation; Y is OR 1 or NR 2 R 3 , and R 1 , R 2 , R 3 and M are as defined herein. Also, methods of treating bacterial infection, pharmaceutical compositions, molecular complexes and processes for preparing compounds.

Claims (19)

1. A compound of formula (I):

wherein:

M is hydrogen or a pharmaceutically acceptable salt-forming cation;

Y is OR 1 ;

R 1 is a radical selected from the group consisting of: C 4-7 saturated heterocycle containing at least one heteroatom selected from O, N, and S wherein the said heterocycle is optionally substituted, and the free ring N atom may optionally take a substituent; or a deuterated compound of any such compound.

2. A compound as recited in claim 1 , wherein the radical R 3 is optionally substituted with one or two substituents independently selected from the following: lower alkyl, amino, substituted amino, carboxamide.

3. A compound as recited in claim 1 , which is selected from the following group of compounds:

and pharmaceutically acceptable salts of such compounds, and deuterated compounds of such compounds and salts.

4. A compound of formula (I) as defined in claim 1 , wherein the compound is selected from the group consisting of:

(2S,5R)-7-oxo-N(pyrrolidin-3-yloxy)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)—N-[(1-methylpyrrolidin-3-yl)oxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-7-oxo-N-(piperidin-3-yloxy)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-7-oxo-N-(pyrrolidin-2-ylmethoxy)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-7-oxo-N-(piperidin-2-ylmethoxy)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-7-oxo-N-(piperidin-3-ylmethoxy)-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)—N-[(5-carbamoylpyrrolidin-3-yl)oxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

or a deuterated compound of any such compound.

5. A pharmaceutical composition containing as an active ingredient, at least one compound as recited in claim 1 .

6. A molecular complex comprising a compound as recited in claim 1 and at least one solvent.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2015
From: NAEJA PHARMACEUTICAL INC.
To: FEDORA PHARMACEUTICALS INC.
Reel/Frame 034823/0783 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2013
From: MAITI, SAMARENDRA N.; NGUYEN, DAI; KHAN, JEHANGIR; LING, RONG
To: NAEJA PHARMACEUTICAL INC.
Reel/Frame 030363/0038 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2012
From: MAITI, SAMARENDRA N.; NGUYEN, DAI; KHAN, JEHANGIR; LING, RONG
To: NAEJA PHARMACEUTICAL INC.
Reel/Frame 029444/0515 →
Continuity (3)
Provisional Application 61641087 · May 1, 2012
Provisional Application 61566240 · Dec 2, 2011
Related Publication 20130225554A1 · Aug 29, 2013