NITROGEN CONTAINING BICYCLIC COMPOUNDS

RELATED PATENT APPLICATIONS

This application claims the priority to and benefit of Indian Provisional Patent Application No. 201921042452 filed on October 18, 2019; the disclosures of which are incorporated herein by reference in its entirety as if fully rewritten herein.

FIELD OF THE INVENTION

The invention relates to nitrogen containing bicyclic compounds, their preparation and their use in treating and/or preventing bacterial infections.

BACKGROUND OF THE INVENTION

The emergence of bacterial resistance to known antibacterial agents is becoming a major challenge in treating bacterial infections. One way forward to treat bacterial infections, and especially those caused by resistant bacteria, is to develop new antibacterial agents that can overcome the bacterial resistance. Coates et al. ( Br . J. Pharmacol. 2007; 152(8), 1147-1154) have reviewed approaches to developing new antibiotics. However, the development of new antibacterial agents is a challenging task. For example, Gwynn et al. (Annals of the New York Academy of Sciences, 2010, 1213: 5-19) have reviewed the challenges in the discovery of antibacterial agents. Several antibacterial agents have been described in the prior art. However, there remains a need for potent antibacterial agents for use in treatment and/or prevention of bacterial infections, including those caused by bacteria that have acquired resistance to one or more of the known antibacterial agents. The inventors have surprisingly discovered certain nitrogen containing bicyclic compounds having antibacterial properties.

SUMMARY OF THE INVENTION

Accordingly, there are provided nitrogen containing bicyclic compounds, methods for preparation of these compounds, pharmaceutical compositions comprising these compounds, and methods for treating and/or preventing bacterial infection in a subject using these compounds.

In one general aspect, there is provided a compound of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof;

Formula (I)

wherein:

B is selected from:

(a) hydrogen,

(b) halogen,

(c) Ci-C6 alkyl,

(d) OR1,

(e) NR1R2,

(f) SH,

(g) SR1,

(h) SOR1,

(i) SO2R1,

CD CHO,

(k) COOR1,

(l) CONR1R2,

(m) CN,

(n) heteroaryl,

(o) heterocycloalkyl, or

(p) NHC(=NH)NH2;

R1 and R2 are each independently:

(a) hydrogen,

(b) C1-C6 alkyl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, SH, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl,

(c) three to seven membered cycloalkyl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, or SH,

(d) three to seven membered heterocycloalkyl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, or SH,

(e) six to fourteen membered aryl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, or SH, or

(f) five to fourteen membered heteroaryl, optionally substituted with one or more substituents independently selected from CN, halogen,

OH, NH2, COOH, CONH2, SH;

M is selected from:

(a) hydrogen,

(b) C1-C6 alkyl, or

(c) a pharmaceutically accepted salt forming cation independently selected from Na, K, or Ca.

In another general aspect, there are provided pharmaceutical compositions comprising a compound of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof.

In another general aspect, there is provided a method for treating or preventing a bacterial infection in a subject, said method comprising administering to said subject a compound of Formula (I) or a stereoisomer or a pharmaceutically acceptable salt thereof.

In yet another general aspect, there is provided a method for treating or preventing a bacterial infection in a subject, said method comprising administering to said subject a pharmaceutical composition comprising a compound of Formula (I) or a stereoisomer or a pharmaceutically acceptable salt thereof.

In another general aspect, there are provided pharmaceutical compositions comprising: (a) a compound of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, and (b) at least one antibacterial agent or a pharmaceutically acceptable derivative thereof.

In another general aspect, there is provided a process for preparing a compound of Formula (I) or a stereoisomer or a pharmaceutically acceptable salt thereof.

The details of one or more embodiments of the invention are set forth in the description below. Other features, objects and advantages of the invention will be apparent from the following description including claims.

DETAILED DESCRIPTION OF THE INVENTION

Reference will now be made to the exemplary embodiments, and specific language will be used herein to describe the same. It should nevertheless be understood that no limitation of the scope of the invention is thereby intended. Alterations and further modifications of the inventive features illustrated herein, and additional applications of the principles of the invention as illustrated herein, which would occur to one of ordinary skills in the relevant art and having possession of this disclosure, are to be considered within the scope of the invention. It must be noted that, as used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the content clearly dictates otherwise. All references including patents, patent applications, and literature cited in the specification are expressly incorporated herein by reference in their entirety.

The inventors have surprisingly discovered certain nitrogen containing bicyclic compounds having antibacterial properties.

The term “C1-C6 alkyl” as used herein refers to branched or unbranched acyclic hydrocarbon radical with 1 to 6 carbon atoms. Typical, non-limiting examples of “C1-C6 alkyl” include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl and the like. The “C1-C6 alkyl” may be unsubstituted, or substituted with one or more substituents. Typical, non-limiting examples of such substituents include halogen, alkoxy, CN, COOH, CONH2, OH, -NH2, -NHCOCH3, cycloalkyl, heterocycloalkyl, heteroaryl, aryl, urea, thiourea, guanidine, keto, oxime, O-alkyl, O-aryl, N-alkyl, N-aryl, SO-alkyl, SO-aryl, S-alkyl, S-aryl, SO2-alkyl, SO2-aryl, OSO2-alkyl, OSO2-aryl, COO-alkyl, COO-aryl, CON-alkyl, CON-aryl, NHCO-alkyl, NHCO-aryl, NHCON-alkyl ,NHCON-aryl, NHCSN-alkyl, NHC(=NH)NH2 NHCSN-aryl, (=N-0-alkyl) and the like.

The term “cycloalkyl” as used herein refers to three to seven member cyclic hydrocarbon radicals. The cycloalkyl group optionally incorporates one or more double or triple bonds, or a combination of double bonds and triple bonds, but which is not aromatic. Typical, non-limiting examples of cycloalkyl groups include cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane. The cycloalkyl may be unsubstituted, or substituted with one or more substituents. Typical, non-limiting examples of such substituents include C1-C6 alkyl, halogen, CN, COOH, CONH2, OH, -NH2, -NHCOCH3, cycloalkyl, heterocycloalkyl, heteroaryl, aryl, urea, thiourea, guanidine, keto, oxime, O-alkyl, O-aryl, N-alkyl, N-aryl, SO-alkyl, SO-aryl, S-alkyl, S-aryl, SO2-alkyl, SO2-aryl, OSO2-alkyl, OSO2-aryl COO-alkyl, COO-aryl, CON-alkyl, CON-aryl, NHCO-alkyl, NHCO-aryl, NHCON-alkyl ,NHCON-aryl, NHCSN-alkyl, NHC(=NH)NH2, NHCSN-aryl, (=N-0-alkyl) and the like.

The term “heterocycloalkyl” as used herein refers to four to seven member cycloalkyl group containing one or more heteroatoms selected from nitrogen, oxygen or sulfur. The heterocycloalkyl group optionally incorporates one or more double or triple bonds, or a combination of double bonds and triple bonds, but which is not aromatic. Typical, non-limiting examples of heterocycloalkyl groups include azetidine, pyrrolidine, 2-oxopyrrolidine, imidazolidin-2-one, piperidine, oxazine, thiazine, piperazine, morpholine, thiomorpholine, azapane, piperazin-2,3-dione and the like. The heterocycloalkyl may be unsubstituted, or substituted with one or more substituents. Typical, non-limiting examples of such substituents include Ci-C6 alkyl, halogen, CN, COOH, CONH2, OH, -NH2, -NHCOCH3, cycloalkyl, heterocycloalkyl, heteroaryl, aryl, urea, thiourea, guanidine, keto, oxime, O-alkyl, O-aryl, N-alkyl, N-aryl, SO-alkyl, SO-aryl, S-alkyl, S-aryl, SO2-alkyl, SO2-aryl, OSO2-alkyl, OSO2-aryl, COO-alkyl, COO-aryl, CON-alkyl, CON-aryl, NHCO-alkyl, NHCO-aryl, NHCON-alkyl, NHCON-aryl, NHCSN-alkyl, NHC(=NH)NH2, NHCSN-aryl, (=N-0-alkyl) and the like.

The term “aryl” as used herein refers to a monocyclic or polycyclic aromatic hydrocarbon. Typical, non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, fluorenyl, phenanthrenyl, and the like. The aryl group may be unsubstituted, or substituted with one or more substituents. Typical, non-limiting examples of such substituents include C1-C6 alkyl, halogen, CN, COOH, CONH2, OH, -NH2, -NHCOCH3, cycloalkyl, heterocycloalkyl, heteroaryl, aryl, urea, thiourea, guanidine, keto, oxime, O-alkyl, O-aryl, N-alkyl, N-aryl, SO-alkyl, SO-aryl, S-alkyl, S-aryl, SO2-alkyl, SO2-aryl, OSO2-alkyl, OSO2-aryl, COO-alkyl, COO-aryl, CON-alkyl, CON-aryl, NHCO-alkyl, NHCO-aryl, NHCON-alkyl, NHCON-aryl, NHCSN-alkyl, NHCSN-aryl, NHC(=NH)NH2, (=N-0-alkyl) and the like.

The term “heteroaryl” as used herein refers to a monocyclic or polycyclic aromatic hydrocarbon group wherein one or more carbon atoms have been replaced with heteroatoms selected from nitrogen, oxygen, and sulfur. If the heteroaryl group contains more than one heteroatom, the heteroatoms may be the same or different. Typical, non-limiting example of heteroaryl groups include 1,2,4-oxadiazol, 1,3,4-oxadiazol, 1,3,4-thiadiazol, 1,2,3-triazol, 1,2,3,4-tetrazol, 1,3-oxazol, 1,3-thiazole, pyridine, pyrimidine, pyrazine, pyridazine, furan, pyrrol, thiophene, imidazole, pyrazole, benzofuran, benzothiophene, benzimidazole, benzoxazole, benzothiazole, thiazole, and the like. The heteroaryl group may be unsubstituted, or substituted with one or more substituents. Typical, non-limiting examples of such substituents include C1-C6 alkyl, halogen, CN, COOH, CONH2, OH, -NH2, -NHCOCH3, cycloalkyl, heterocycloalkyl, heteroaryl, aryl, urea, thiourea, guanidine, keto, oxime, O-alkyl, O-aryl, N-alkyl, N-aryl, SO-alkyl, SO-aryl, S-alkyl, S-aryl S02-alkyl, S02-aryl, 0S02-alkyl, 0S02-aryl, COO-alkyl, COO-aryl, CON-alkyl, CON-aryl, NHCO-alkyl, NHCO-aryl, NHCON-alkyl, NHCON-aryl, NHCSN-alkyl, NHC(=NH)NH2, NHCSN-aryl, (=N-0-alkyl) and the like.

The term “stereoisomers” as used herein refers to and includes compounds that have identical chemical constitution, but differ with regard to the arrangement of their atoms or groups in space. The compounds of Formula (I) contains asymmetric or chiral centres (including those marked with “*”) and, therefore, exist in different stereoisomeric forms. It is intended, unless specified otherwise, that all stereoisomeric forms of the compounds of Formula (I) as well as mixtures thereof, including racemic mixtures, form part of the present invention. In addition, all geometric and positional isomers (including cis and trans-forms) as well as mixtures thereof, are also embraced within the scope of the invention. In general, a reference to a compound is intended to cover its stereoisomers and a mixture of various stereoisomers.

The term “optionally substituted” as used herein means that substitution is optional and therefore includes both unsubstituted and substituted atoms and moieties. A “substituted” atom or moiety indicates that any hydrogen on the designated atom or moiety can be replaced with a selection from the indicated substituent group, provided that the normal valence of the designated atom or moiety is not exceeded, and that the substitution results in a stable compound.

The term “pharmaceutically acceptable salt” as used herein refers to one or more salts of a given compound which possesses the desired pharmacological activity of the free compound and which are neither biologically nor otherwise undesirable. In general, the “pharmaceutically acceptable salts” refer to and include those salts that are suitable for use in contact with the tissues of human and animals without undue toxicity, irritation, allergic response and the like, and are commensurate with a reasonable benefit/risk ratio. Pharmaceutically acceptable salts are well known in the art. For example, S. M. Berge, et al. (J.

Pharmaceutical Sciences, 66: 1-19 (1977)), incorporated herein by reference in its entirety, describes various pharmaceutically acceptable salts in details.

In general, the compounds according to the invention contain basic (e.g. nitrogen atoms) as well as acid moieties (e.g. SO3H group). A person of skills in the art would appreciate that such compounds, therefore, can form acidic salts (formed with inorganic and/or organic acids), as well as basic salts (formed with inorganic and/or organic bases). Such salts can be prepared using procedures described in the art. For example, the basic moiety can be converted to its salt by treating a compound with a suitable amount of acid. Typical, non-limiting examples of such suitable acids include hydrochloric acid, trifluoroacetic acid, methanesulphonic acid, or the like. Alternatively, the acid moiety may be converted into its salt by treating with a suitable base. Typical non-limiting examples of such bases include sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate or the like. In case of compounds containing more than one functional group capable of being converted into salt, each such functional group may be converted to a salt independently. For example, in case of compounds containing two basic nitrogen atoms, one of the basic nitrogen can form salt with one acid while the other basic nitrogen can form salt with another acid. The compounds according to the invention contain both, acidic as well as basic moieties, and thus can form inner salts or corresponding zwitterions. In general, all pharmaceutically acceptable salt forms of compounds of Formula (I) according to invention including acid addition salts, base addition salts, zwitterions or the like are contemplated to be within the scope of the present invention and are generically referred to as pharmaceutically acceptable salts.

The term “infection” or “bacterial infection” as used herein refers to and includes presence of bacteria, in or on a subject, which, if its growth were inhibited, would result in a benefit to the subject. As such, the term "infection" in addition to referring to the presence of bacteria also refers to normal flora, which is not desirable. The term "infection" includes infection caused by bacteria.

The term “treat”, “treating” or “treatment” as used herein refers to administering a medicament, including a pharmaceutical composition, or one or more pharmaceutically active ingredients, for prophylactic and/or therapeutic purposes. The term "prophylactic treatment" refers to treating a subject who is not yet infected, but who is susceptible to, or otherwise at a risk of infection (preventing the bacterial infection). The term "therapeutic treatment" refers to administering treatment to a subject already suffering from infection. The terms “treat”, “treating” or “treatment” as used herein also refer to administering

compositions or one or more of pharmaceutically active ingredients discussed herein, with or without additional pharmaceutically active or inert ingredients, in order to: (i) reduce or eliminate either a bacterial infection or one or more symptoms of the bacterial infection, or (ii) retard the progression of a bacterial infection or of one or more symptoms of the bacterial infection, or (iii) reduce the severity of a bacterial infection or of one or more symptoms of the bacterial infection, or (iv) suppress the clinical manifestation of a bacterial infection, or (v) suppress the manifestation of adverse symptoms of the bacterial infection.

The term “pharmaceutically effective amount” or “therapeutically effective amount” or “effective amount” as used herein refers to an amount, which has a therapeutic effect or is the amount required to produce a therapeutic effect in a subject. For example, a therapeutically or pharmaceutically effective amount of an antibacterial agent or a pharmaceutical composition is the amount of the antibacterial agent or the pharmaceutical composition required to produce a desired therapeutic effect as may be judged by clinical trial results, model animal infection studies, and/or in vitro studies (e.g. in agar or broth media). The pharmaceutically effective amount depends on several factors, including but not limited to, the microorganism (e.g. bacteria) involved, characteristics of the subject (for example height, weight, sex, age and medical history), severity of infection and the particular type of the antibacterial agent used. For prophylactic treatments, a therapeutically or prophylactically effective amount is that amount which would be effective in preventing a microbial (e.g. bacterial) infection. The compounds and/or pharmaceutical compositions according to the invention are used in amounts that are effective in providing the desired therapeutic effect or result.
We Claim

1. A compound of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof:

wherein:

B is selected from:

(a) hydrogen,

(b) halogen,

(c) Ci-C6 alkyl,

(d) OR1,

(e) NR1R2,

(f) SH,

(g) SR1,

(h) SOR1,

(i) SO2R1,

(j) CHO,

(k) COOR1,

(l) CONR1R2,

(m) CN,

(n) heteroaryl,

(o) heterocycloalkyl, or

(P) NHC(=NH)NH2;

R1 and R2 are each independently:

(a) hydrogen,

(b) C1-C6 alkyl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, SH, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl,

(c) three to seven membered cycloalkyl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, or SH,

(d) three to seven membered heterocycloalkyl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, or SH,

(e) six to fourteen membered aryl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, or SH, or

(f) five to fourteen membered heteroaryl, optionally substituted with one or more substituents independently selected from CN, halogen, OH, NH2, COOH, CONH2, SH;

M is selected from:

(a) hydrogen,

(b) C1-C6 alkyl, or

(c) a pharmaceutically accepted salt forming cation independently selected from Na, K, or Ca.

2. The compound according to Claim 1 , selected from:

(2S,5R)-N-{ [(2S,4R)-4- Methyl -pyrrol idin-2-ylJmethyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-Methyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{ [(2R,4S)-4- Methyl -pyrrol idin-2-yl Jmethyloxy} -7-OXO-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-Methyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-Hydroxymethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

2S,5R)-N-{[(2S,4S)-4-Hydroxymethy-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-Hydroxymethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4R)-4-Hydroxymethy-pyrrolidin-2-yl]methyloxy } -7-OXO-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-Aminomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy) -l,6-diazabicyclo[3.2.1]octane-2-carboxamide trifluoroacetate salt;

(2S,5R)-N-{[(2S,4S)-4-Aminomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide trifluoroacetate salt;

(2S,5R)-N-{[(2R,4S)-4-Aminomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide trifluoroacetate salt;

(2S,5R)-N-{[(2R,4R)-4-Aminomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy) -l,6-diazabicyclo[3.2.1]octane-2-carboxamide trifluoroacetate salt;

(2S,5R)-N-{[(2S,4R)-4-Cyanomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

2S,5R)-N-{[(2S,4S)-4-Cyanomethy-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-Cyanomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-Cyanomethy-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6- (sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Azetidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(Azetidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4S)-4-( Azetidin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4R)-4-(Azetidin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Pyrrolidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(Pyrrolidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(Pyrrolidin-l-ylmethyl)-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 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(Azepan-l-ylmethyl)-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 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(Piperazin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4S)-4-(Piperazin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4R)-4-(Piperazin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4S)-4-(Morpholin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4R)-4-(Thiomorpholin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(Thiomorpholin-l-ylmethyl)-pyrrolidin-2-yl] methyloxy } -7 -oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ] octane-2-carboxamide;

(2S,5R)-N- { [(2R,4S)-4-(Thiomorpholin- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(Thiomorpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(lH-Pyrrol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N - { [(2S,4S)-4-( 1 H-Pyrrol- 1 -ylmethyl)-pyrrolidin-2-yl] methyloxy } -7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(lH-Pyrrol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [{2R,4R)-4-{ 1 H-Pyrrol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy } -7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(lH-imidazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4S)-4-( lH-imidazol- 1 -ylmethyl)-pyrrolidin-2-yl] methyloxy } -7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(lH-imidazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [{2R,4R)-4-{ 1 H-imidazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N - { [(2S,4R)-4-( 1 H-pyrazol- 1 -ylmethyl)-pyrrolidin-2-yl] methyloxy } -7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxyj- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxyj- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4R)-4-( 1H- 1 ,2,3-triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4S)-4-( 1 H- 1 ,2,3-triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4S)-4-( 1H- 1 ,2,3-triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [{2R,4R)-4-{ 1 H- 1 ,2,3-txiazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4R)-4-( 1H- 1 ,2,4-triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4S)-4-( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4S)-4-( 1H- 1 ,2,4-triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N- { [{2R,4R)-4-{ 1 H- 1 ,2,4,triazol- 1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N - { [(2S,4R)-4-( 1 H-tetrazol- 1 -ylmethyl)-pyrrolidin-2-yl] methyloxy } -7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(lH-tetrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(lH-tetrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4R)-4-(lH-tetrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4R)-4-(2H-tetrazoly-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}- 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxyj- 7 -oxo-6-(sulfooxy)- 1 , 6-diazabicyclo[3.2.1 ] octane-2-carboxamide ;

(2S,5R)-N- { [(2R,4R)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxy } - 7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

(2S,5R)-N-{[(2S,4S)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy}-7- oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2S,4R)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy } -7- oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4S)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy } -7- oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

(2S,5R)-N- { [(2R,4R)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy } -7- oxo-6-(sulfooxy)- 1 ,6-diazabicyclo[3.2.1 ]octane-2-carboxamide;

or a stereoisomer or a pharmaceutically acceptable salt thereof.

3. The compound according to Claim 1, selected from:

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Methyl-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-Methyl-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-Methyl-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-Methyl-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-Hydroxymethyl-pyrrolidin-2- yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2- carboxamide;

Sodium salt of 2S,5R)-N-{[(2S,4S)-4-Hydroxymethy-pyrrolidin-2- yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2- carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Hydroxymethy-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S, 5R)-N- { [(2R,4R)-4- Hydroxymethyl -pyrrol idin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{ [(2S, 4R)-4- Am inomethyl -pyrrol idin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carbox amide trifluoroacetate salt;

Sodium salt of (2S,5R)-N-{ [(2S,4S)-4- Am inomethyl -pyrrol idin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carbox amide trifluoroacetate salt;

Sodium salt of (2S,5R)-N-{ [(2R,4S)-4- Am inomethyl -pyrrol idin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carbox amide trifluoroacetate salt;

Sodium salt of (2S,5R)-N-{ [(2R,4R)-4- Am inomethyl -pyrrol idin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carbox amide trifluoroacetate salt;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Cyanomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of 2S,5R)-N-{[(2S,4S)-4-Cyanomethy-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Cyanomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Cyanomethy-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Chloromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Aziridin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Azetidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Azetidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azetidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Azetidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Pyrrolidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Pyrrolidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Pyrrolidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Pyrrolidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Piperidin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Azepan-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{ [(2S,4R)-4-(Piperazin- 1 -yl methyl )-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Piperazin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Piperazin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Piperazin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Morpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Thiomorpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Thiomorpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Thiomorpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Thiomorpholin-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(lH-Pyrrol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(lH-Pyrrol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(lH-Pyrrol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(lH-Pyrrol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(lH-imidazol-l-ylmethyl)-pyrrolidin- 2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(lH-imidazol-l-ylmethyl)-pyrrolidin- 2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(lH-imidazol-l-ylmethyl)-pyrrolidin- 2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(lH-imidazol-l-ylmethyl)-pyrrolidin- 2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(lH-pyrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(lH-l,2,3-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(lH-l,2,3-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(lH-l,2,3-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(lH-l,2,3-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(lH-l,2,4-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(lH-l,2,4-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(lH-l,2,4-triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(lH-l,2,4,triazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(lH-tetrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(lH-tetrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(lH-tetrazol-l-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(lH-tetrazol-l-ylmethyl)-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-tetrazoly-2-ylmethyl)-pyrrolidin- 2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2-carboxamide;

Sodium salt of (2S,5R)-N-{ [(2R,4S)-4-Carbamimidomethyl-pyrrolidin-2- yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2- carboxamide;

Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Carbamimidomethyl-pyrrolidin-2- yl]methyloxy}-7-oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]octane-2- carboxamide;

or a stereoisomer.

4. The compound according to Claim 1 , selected from:

5. A pharmaceutical composition comprising a compound according to any one of the claims 1 to 4.

6. The pharmaceutical composition according to Claim 5, further comprising at least one antibacterial agent or a pharmaceutically acceptable derivative thereof.

7. The pharmaceutical composition according to Claim 6, wherein the antibacterial agent is a beta-lactam antibacterial agent.

8. The pharmaceutical composition according to Claim 6, wherein the antibacterial agent is at least one selected from a group consisting of Ansamycin, Carbacephem, Carbapenam, Carbapenem, Cephalosporin, Cephamycin, Cephem, Lincosamide, Lipopeptide, Macrolide, Ketolide, Monobactam, Nitrofuran, Oxacephem, Oxapenam, Oxazolidinone, Penam, Penem, Penicillin, Polypeptide, Quinolone, Sulfonamide, or Tetracycline antibacterial agents.

9. The pharmaceutical composition according to Claim 6, wherein the antibacterial agent is at least one selected from a group consisting of cefacetrile, cefaclor, cefadroxil, cefalexin, cefaloglycin, cefalonium, cefaloridine, cefalotin, cefamandole, cefapirin, cefatrizine, cefazaflur, cefazedone, cefazolin, cefbuperazone, cefcapene, cefclidin, cefdaloxime, cefdinir, cefditoren, cefepime, cefetamet, cefixime, cefluprenam, cefmenoxime, cefmetazole, cefminox, cefodizime, cefonicid, cefoperazone, ceforanide, cefoselis, cefotaxime, cefotetan, cefotiam, cefovecin, cefoxitin, cefoxitin, cefozopran, cefpimizole, cefpiramide, cefpirome, cefpodoxime, cefprozil, cefquinome, cefradine, cefroxadine, cefsulodin, ceftaroline, ceftazidime, cefteram, ceftezole, ceftibuten, ceftiofur, ceftiolene, ceftizoxime, ceftobiprole, ceftolozane, ceftriaxone, cefuroxime, cefuzonam, cephaloridine, cephradine, cefiderocol, flomoxef, latamoxef, loracarbef, moxalactam, or a pharmaceutically acceptable derivative thereof.

10. The pharmaceutical composition according to Claim 6, wherein the antibacterial agent is at least one selected from a group consisting of cefaclor, cefadroxil, cefalexin, cefdinir, cefixime, cefpirome, cefpodoxime, cefprozil, cefradine, ceftibuten, cefuroxime, loracarbef, or a pharmaceutically acceptable derivative thereof.

11. The pharmaceutical composition according to Claim 6, wherein the antibacterial agent is at least one selected from a group consisting of ertapenem, doripenem, imipenem, meropenem, panipenem, biapenem, tebipenem, lenapenem, tomopenem, or a pharmaceutically acceptable derivative thereof.

12. The pharmaceutical composition according to Claim 6, wherein the antibacterial agent is at least one selected from a group consisting of cefpodoxime axetil, cefpodoxime proxetil, ceftibuten, cefuroxime, cefuroxime axetil, cefixime, or a pharmaceutically acceptable derivative thereof.

13. Use of a compound according to any one of the claims 1 to 4, in treating or preventing a bacterial infection.

14. Use of a pharmaceutical composition according to any one of the claims 5 to 12, in treating or preventing a bacterial infection.

15. A method for treating or preventing bacterial infection in a subject, said method comprising administering to said subject a compound according to any one of the Claims 1 to 4.

16. A method for treating or preventing bacterial infection in a subject, said method comprising administering to said subject a pharmaceutical composition according to any one of the Claims 5 to 12.