# US 10,501,464 B2 · 7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide containing compounds and their use in treating bacterial infections

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- Number: US 10,501,464 B2
- Document ID: US10501464B2
- Status: Granted
- Kind: B2
- Application number: 15/781,121
- Filed: 2016-12-08
- Published: 2019-01-17
- Granted: 2019-12-10
- Earliest claimed: 2015-12-11
- Assignees: Wockhardt Limited
- Applicants: Wockhardt Limited
- Inventors: Vijaykumar Jagdishwar Patil; Sudhir Shengule; Mangesh Pawar; Rajib Bhuniya; Zaki Ahmed Burhanuddin Munshi; Prashant Ratnakar Joshi; Swapna Shripad Takalkar; Mahesh Vithalbhai Patel
- Web page: https://patentgrep.com/patent/US10501464B2

## CPC

- C07D 471/08: Bridged systems
- A61P 31/04: Antibacterial agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of Formula (I), their preparation, and use in preventing or treating a bacterial infection are disclosed.

## Claims

### Claim 1

A compound of Formula (I):
or a stereoisomer or a pharmaceutically acceptable salt thereof; wherein:
X is selected from —CH2—O- or —(C═O)—NH—;
A is heterocycloalkyl or heteroaryl optionally substituted with one or more substituents selected from C1-C6 alkyl, NR2R3, aryl, heteroaryl, cycloalkyl or heterocycloalkyl;
R1 is selected from:
(a) hydrogen,
(b) C1-C6 alkyl optionally substituted with one or more substituents independently selected from OR2, NR2R3, SR2, halogen, CN, COOR2, CONR2R3, SR2, CH2OR2 or CH2NR2R3, aryl, heteroaryl, cycloalkyl or heterocycloalkyl,
(c) halogen,
(d) CN,
(e) CONR2R3,
(f) COOR2,
(g) CHO,
(h) NR2R3,
(i) NHCOOR2,
(j) SR2,
(k) SOR2,
(I) SO2R2,
(m) aryl,
(n) heteroaryl,
(o) cycloalkyl, or
(p) heterocycloalkyl;
R2 and R3are each independently selected from:
(a) hydrogen,
(b) C1-C6 alkyl,
(c) cycloalkyl,
(d) heterocycloalkyl,
(e) aryl, or
(f) heteroaryl;
n is 0, 1, 2, 3or 4;
M is hydrogen or a cation.

### Claim 2 (depends on 1)

The compound according to claim 1, selected from:
(2S,5R)—N-{[(2S,4S)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(2H-1,2,3-triazol-211)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-1,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4S)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(2H-1,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-1,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-pyrrol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1 ,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-pyrrol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1 ,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1 ,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(2H-1,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1H-1,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1H-pyrrole-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1H-pyrrole-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1 ,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1 ,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-pyrrole-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(2H-1,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-1,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(piperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(piperazin-1-yl)pyrrolidi n-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4R)-4-(piperazin-1-yl)pyrrolidi n-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4S)-4-(piperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(4-methylpiperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(4-methylpiperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(4-methylpiperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(4-methylpiperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4R)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4S)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 S,4R)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4R)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2 R,4S)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5 R)-N-{[(2R,4S)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5 R)-N-{[(2S,4S)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4R)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2S,4S)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4R)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N-{[(2R,4S)-4-[4-({[(2S)-1-hydroxypropan-2-yl]amino}methyl)piperidin-1-yl] pyrrolidin-2-yl]methoxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
(2S,5R)-N′-{[(2S,4S)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)--1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N′-{[(2S,4S)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N′-{[(2S,4S)-4-(5-methyl-2H-tetrazol-2-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2R,5R)-N′-{[(2S,4S)-4-(2H-1 ,2,3-triazol-2-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)- -1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2R,5R)-N′-{[(2S,4S)-4-(1H-1 ,2,3-triazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2R,5R)-7-oxo-6-(sulfooxy)-N′-{[(2S,4S)-4-(1H-1 ,2,4-triazol-1-yl)pyrrolidin-2-yl]carbonyl}-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N′-{[(2S,4S)-4-(1H-imidazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N′-{[(2RS,4S)-4-(1H-imidazol-1-yl) pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N-{[(2S,4R)-4-(1H-pyrazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N′-{[(2SR, 4S)-4-(1H-pyrazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
(2S,5R)-N′-{[(2S,4R)-4-(1H-imidazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide; (2S,5R)-N-{[(2R,4S)-4-(1H-imidazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxhydrazide;
or a stereoisomer or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1, selected from:
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(2H-1 ,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1 ,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-1 ,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-1 ,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(2H-1 ,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1 ,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-pyrrol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-pyrrol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoroacetate salt of (2S,5R)-N-{[(2S,4S)-4-(4-amino-1H-1 ,3-imidazol-1 -yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(2-methyl-1H-1 ,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(2H-1 ,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1H-1 ,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1H-pyrrole-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-pyrrole-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoroacetate salt of (2S,5R)-N-{[(2R,4S)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-pyrrole-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(2H-1 ,2,3-triazol-2-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-1 ,2-pyrazol-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoroacetate salt of (2S,5R)-N-{[(2R,4R)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoroacetate salt of (2S,5R)-N-{[(2S,4R)-4-(4-amino-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(2-methyl-1H-1,3-imidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-benzimidazol-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(piperidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(piperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(piperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(piperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(piperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(4-methylpiperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(4-methylpiperazin-1 -yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(4-methylpiperazin-1 -yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(4-methylpiperazin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(morpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(thiomorpholin-4-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(azeditin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(1 ,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(1 ,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(1 ,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(1 ,3-Oxazeditin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(pyrrolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(pyrazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Di trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(imidazolidin-1-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(1 ,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(1,3-oxazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4R)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2S,4S)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4R)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-(1,3-thiazolidin-3-yl)pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,4S)-4-[4-({[(2S)-1-hydroxypropan-2-yl]amino} methyl)piperidin-1-yl]pyrrolidin-2-yl)methoxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;
Sodium salt of (2S,5R)-N′-{[(2S,4S)-4-(1H-tetrazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)—1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2S,5R)-N′-{[(2S,4S)-4-(2H-tetrazol-2-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2S,5R)-N′-{[(2S,4S)-4-(5-methyl-2H-tetrazol-2-yl)pyrrolidin-2-yl]carbonyl} -7-oxo -6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2R,5R)-N′-{[(2S,4S)-4-(2H-1,2,3-triazol-2-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)- -1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2R,5R)-N′-{[(2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2R,5R)-7-oxo-6-(sulfooxy)-N′-{[(2S,4S)-4-(1H-1,2,4-triazol-1-yl)pyrrolidin-2-yl]carbonyl}-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2S,5R)-N′-{[(2S,4S)-4-(1H-imidazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2S,5R)-W-{[(2RS,4S)-4-(1H-imidazol-1-yl) pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-pyrazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Sodium salt of (2S,5R)-W-{[(2SR, 4S)-4-(1H-pyrazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Trifluoro acetic acid salt of (2S,5R)-N′-{[(2S,4R)-4-(1H-imidazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide;
Trifluoro acetic acid salt of (2S,5R)-N-{[(2R,45)-4-(1H-imidazol-1-yl)pyrrolidin-2-yl]carbonyl}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxhydrazide; or a stereoisomer thereof.

### Claim 4 (depends on 1)

The compound of Formula (I) according to claim 1, wherein X is —CH2—O—.

### Claim 5 (depends on 1)

The compound of Formula (I) according to claim 1, wherein X is —(C═O)—NH—.

### Claim 6 (depends on 1)

The compound of Formula (I) according to claim 1, wherein A is heterocycloalkyl.

### Claim 7 (depends on 1)

The compound of Formula (I) according to claim 1, wherein A is heteroaryl.

### Claim 8 (depends on 1)

The compound of Formula (I) according to claim 1, wherein A is heteroaryl linked to pyrrolidine through “N” of heteroaryl.

### Claim 9 (depends on 1)

The compound of Formula (I) according to claim 1, wherein A is heterocycloalkyl linked to pyrrolidine through “N” of heterocycloalkyl.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising a compound of Formula (I) according to claim 1, for use in prevention or treatment of bacterial infection.

### Claim 11 (depends on 10)

The pharmaceutical composition according to claim 10, further comprising at least one antibacterial agent or a pharmaceutically acceptable salt thereof.

### Claim 12 (depends on 11)

The pharmaceutical composition according to claim 11, wherein the antibacterial agent is selected from a group consisting of aminoglycosides, ansamycins, penems, carbapenems, carbacephems, cephalosporins, cephamycins, lincosamides, lipopeptides, macrolides, monobactams, nitrofurans, penicillins, polypeptides, quinolones, sulfonamides, tetracyclines, and oxazolidinone antibacterial agents.

### Claim 13 (depends on 11)

The pharmaceutical composition according to claim 11, wherein the antibacterial agent is a beta-lactam antibacterial agent.

### Claim 14 (depends on 11)

The pharmaceutical composition according to claim 11, wherein the antibacterial agent is selected from a group consisting of cephalothin, cephaloridine, cefaclor, cefadroxil, cefamandole, cefazolin, cephalexin, cephradine, ceftizoxime, cefoxitin, cephacetrile, cefotiam, cefotaxime, cefsulodin, cefoperazone, ceftizoxime, cefmenoxime, cefmetazole, cephaloglycin, cefonicid, cefodizime, cefpirome, ceftazidime, ceftriaxone, cefpiramide, cefbuperazone, cefozopran, cefepime, cefoselis, cefluprenam, cefuzonam, cefpimizole, cefclidin, cefixime, ceftibuten, cefdinir, cefpodoximeaxetil, cefpodoximeproxetil, cefterampivoxil, cefetametpivoxil, cefcapenepivoxil or cefditorenpivoxil, cefuroxime, cefuroxime axetil, loracarbacef, ceftaroline, ceftolozane, latamoxef, piperacillin, imipenem, doripenem, and meropenem.

### Claim 15 (depends on 1)

A method for preventing or treating a bacterial infection in a subject, said method comprising administering to said subject a pharmaceutically effective amount of a compound according to claim 1.

### Claim 16 (depends on 11)

A method for preventing or treating a bacterial infection in a subject, said method comprising administering to said subject a pharmaceutically effective amount of a compound according to claim 11.