BICYCLIC COMPOUNDS CONTAINING NITROGEN
Patent Information
- Application Number
- MX2022004639
- Authority / Receiving Office
- MX · MX
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2019-10-18
- Filing Date
- 2022-04-18
- Publication Date
- 2026-02-25
- Estimated Expiration
- 2040-10-18
AI Technical Summary
The emergence of bacterial resistance to known antibacterial agents poses a significant challenge in treating bacterial infections, necessitating the development of new antibacterial agents that can overcome resistance.
The development of nitrogen-containing bicyclic compounds with antibacterial properties, which can be administered alone or in combination with existing antibacterial agents to treat or prevent bacterial infections.
These compounds demonstrate efficacy in treating and preventing bacterial infections, including those caused by resistant bacteria, by inhibiting bacterial growth and reducing infection severity.
Abstract
Description
BICYCLIC COMPOUNDS CONTAINING NITROGEN Related Patent Applications This application claims priority and benefit from Indian provisional patent application No. 201921042452 filed on October 18, 2019; the descriptions of which are incorporated herein by reference in their entirety as if fully rewritten herein. Field of Invention The invention relates to nitrogen-containing bicyclic compounds, their preparation, and their use in the treatment and / or prevention of bacterial infections. Background of the Invention The emergence of bacterial resistance to known antibacterial agents is becoming a major challenge in the treatment of bacterial infections. One way to advance the treatment of bacterial infections, especially those caused by resistant bacteria, is to develop new antibacterial agents that can overcome bacterial resistance. Coates et al. (Br. J. Pharmacol. 2007; 152(8), 1147-1154) have reviewed approaches to developing new antibiotics. However, developing 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 discovering antibacterial agents. Several antibacterial agents have been described in the previous technique.However, the need remains for potent antibacterial agents for the treatment and / or prevention of bacterial infections, including those caused by bacteria that have acquired resistance to one or more known antibacterial agents. Inventors have surprisingly discovered certain nitrogen-containing bicyclic compounds that possess antibacterial properties. Summary of the Invention Accordingly, nitrogen-containing bicyclic compounds, methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods for treating and / or preventing bacterial infections in a subject using these compounds are provided. In general terms, a compound of Formula (I), or a stereoisomer or one of its pharmaceutically acceptable salts is provided; Formula (I) β?αι?ηη / ζζηζ / Β / γΐΛΐ where: B is selected from: (a) hydrogen, (b) halogen, (c) alkyl Ci-C6, (d)ORi, (e) NRiR2, (f)SH, (g)SRi, (h)SORi, (i) SO2Ri, (j)CHO, (k) COORi, (I) CONRiR2, (m)CN, (n) heteroaryl, (o) heterocycloalkyl, or (p); NHC(=NH)NH2; Ri and R2are each independently: (a) hydrogen, (b) Ci-Ce alkyl, optionally substituted with one or more substituents selected independently 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 selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, (d) three- to seven-membered heterocycloalkyl, optionally substituted with one or more substituents selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, (e) six- to fourteen-membered aryl, optionally substituted with one or more substituents selected independently 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) Ci-Ce alkyl, or (c) a pharmaceutically accepted salt-forming cation selected independently from Na, K, or Ca. In another general aspect, pharmaceutical compositions comprising a compound of formula (I), a stereoisomer, or one of its pharmaceutically acceptable salts are provided. In another general aspect, a method is provided 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 another general aspect, a method is provided 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, pharmaceutical compositions are provided comprising: (a) a compound of Formula (I), or a pharmaceutically acceptable stereoisomer or salt thereof, and (b) at least one antibacterial agent or a pharmaceutically acceptable derivative thereof. In another general aspect, a process is provided for preparing a compound of Formula (I) or a stereoisomer or one of its pharmaceutically acceptable salts. βρο^ηη / ζζηζ / Β / γίΛΐ Details of one or more embodiments of the invention are set forth in the following description. Other features, objects, and advantages of the invention will be apparent from the following description, including the claims. Detailed Description of the Invention Reference will now be made to exemplary embodiments, and specific language will be used in this document to describe them. However, it should be understood that this is not intended to limit the scope of the invention. Further alterations and modifications of the inventive features illustrated herein, and further applications of the principles of the invention as illustrated herein, which would occur to a person skilled in the relevant art and in possession of this description, will be considered to be within the scope of the invention. It should be noted that, as used in this specification and in the appended claims, the singular forms a, an, and the include plural referents unless the context clearly indicates otherwise.All references, including patents, patent applications, and the bibliography cited in the descriptive report, are expressly incorporated herein as references in their entirety. The inventors have surprisingly discovered certain nitrogen-containing bicyclic compounds that have antibacterial properties. The term Ci-C6 alkyl, as used herein, refers to a branched or unbranched acyclic hydrocarbon radical with 1 to 6 carbon atoms. Typical, but not limited to, examples of Ci-C6 alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, and the like. The “Ci-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, (=NO-alkyl) and the like. The term cycloalkyl, as used herein, refers to cyclic hydrocarbon radicals of three to seven members. The cycloalkyl group optionally incorporates one or more double or triple bonds, or a combination of double and triple bonds, but is not aromatic. Typical, but not limited to, 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 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, (=NO-alkyl) and the like. The term heterocycloalkyl, as used herein, refers to a four- to seven-membered 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 and triple bonds, but is not aromatic. Typical, non-limiting examples of heterocycloalkyl groups include azetidine, pyrrolidine, 2-oxopyrrolidine, imidazolidin-2-one, piperidine, oxazine, thiazine, piperazine, morpholine, thiomorpholine, azapano, 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-Cs 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, NHCOalkyl, NHCO-aryl, NHCON-alkyl, NHCON-aryl, NHCSN-alkyl, NHC(=NH)NH2, NHCSNaryl, (=NO-alkyl) and the like. The term aryl, as used herein, refers to a monocyclic or polycyclic aromatic hydrocarbon. Typical, but not limited to, 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 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, NHCOalkyl, NHCO-aryl, NHCON-alkyl, NHCON-aryl, NHCSN-alkyl, NHCSN-aryl, NHC(=NH)NH2, (=NO-alkyl) and the like. The term heteroaryl, as used herein, refers to a monocyclic or polycyclic aromatic hydrocarbon group in which one or more carbon atoms have been replaced by 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 examples of heteroaryl groups include 1,2,4-oxadiazole, 1,3,4-oxygen, and 1,3,4-oxygen. RPQfrnn / zznz / B / YiAi oxadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,3,4-tetrazol, 1,3-oxazole, 1,3-thiazole, pyridine, pyrimidine, pyrazine, pyridazine, furan, pyrrole, 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 alkyl Ci-Ce, 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, NHCOalkyl, NHCO-aryl, NHCON-alkyl, NHCON-aryl, NHCSN-alkyl, NHC(=NH)NH2, NHCSNaryl, (=NO-alkyl) and the like. The term stereoisomers, as used herein, refers to and includes compounds that have an identical chemical constitution but differ with respect to the arrangement of their atoms or groups in space. Compounds of formula (I) contain asymmetric or chiral centers (including those marked with *) and thus exist in different stereoisomeric forms. Unless otherwise specified, all stereoisomeric forms of compounds of formula (I), as well as mixtures thereof, including racemic mixtures, are intended to be part of the present invention. In addition, all geometric and positional isomers (including cis and trans forms), as well as mixtures thereof, are also included within the scope of the invention. In general, a reference to a compound is intended to cover its stereoisomers and a mixture of several stereoisomers. The term "optionally substituted" as used herein means that the substitution is optional and therefore includes both substituted and unsubstituted atoms and moieties. A substituted atom or moiety indicates that any hydrogen in the designated atom or moiety may be replaced with a selection of the indicated substituent group, provided that the normal valency 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 that possess the desired pharmacological activity of the free compound and are not undesirable either biologically or otherwise. In general, pharmaceutically acceptable salts refer to and include those salts that are suitable for use in contact with human and animal tissues without undue toxicity, irritation, allergic response, and the like, and are proportionate to a reasonable benefit / benefit ratio of risk. 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 full, describes several pharmaceutically acceptable salts in detail. βροίτηη / ζζηζ / Β / γίΛΐ In general, the compounds according to the invention contain basic moieties (e.g., nitrogen atoms) as well as acids (e.g., SO3H groups). A person skilled in the art would appreciate that such compounds can therefore form acid 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 the procedures described in the art. For example, the basic moiety can be converted into 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, methanesulfonic acid, and the like. Alternatively, the acid moiety can be converted into its salt by treating it with a suitable base. Typical, non-limiting examples of such bases include sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, and the like.In the case of compounds containing more than one functional group capable of forming a salt, each of these functional groups can independently form a salt. For example, in the case of compounds containing two basic nitrogen atoms, one of the basic nitrogens can form a salt with one acid, while the other basic nitrogen can form a salt with a different acid. Compounds according to the invention contain both acidic and basic fractions and can therefore form corresponding internal salts or zwitterions. In general, all pharmaceutically acceptable salt forms of the compounds of Formula (I) according to the invention, including acid addition salts, base addition salts, zwitterions, or the like, are contemplated 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 the presence of bacteria in or on a subject, the inhibition of which 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 the normal flora, which is undesirable. The term infection includes infection caused by bacteria. The term "treat," "treating," or "treatment," as used herein, refers to the administration of a medicinal product, including a pharmaceutical composition, or one or more pharmaceutically active ingredients, for prophylactic and / or therapeutic purposes. The term "prophylactic treatment" refers to the treatment of a subject who is not yet infected but is susceptible to, or otherwise at risk of, infection (prevention of bacterial infection). The term "therapeutic treatment" refers to the administration of treatment to a subject who is already suffering from an infection.The terms treat, treating, or treatment as used herein also refer to the administration of compositions or one or more of the pharmaceutically active ingredients discussed herein, with or without additional pharmaceutically active or inert ingredients, to: (i) reduce or eliminate a bacterial infection or one or more symptoms of bacterial infection, or (ii) delay the progression of a bacterial infection or one or more symptoms of bacterial infection, or (iii) reduce the severity of a bacterial infection or one or more symptoms of bacterial infection, or (iv) suppress the clinical manifestation of a bacterial infection, or (v) suppress the manifestation of adverse symptoms of bacterial infection. The term pharmaceutically effective amount, therapeutically effective amount, or effective amount as used herein refers to an amount that has a therapeutic effect or is the amount required to produce a therapeutic effect in a subject. For example, a therapeutic or pharmaceutically effective amount of an antibacterial agent or pharmaceutical composition is the amount of the antibacterial agent or pharmaceutical composition needed to produce a desired therapeutic effect, as can be judged by the results of clinical trials, infection studies in animal models, and / or in vitro studies (e.g., in agar or broth). The pharmaceutically effective amount depends on several factors, including, but not limited to, the microorganism (e.g., bacteria) involved, the characteristics of the subject (e.g., height, weight, sex, age, and medical history), the severity of the infection, and the particular type of antibacterial agent used.For prophylactic treatments, a therapeutic or prophylactically effective amount is that amount which would be effective in preventing a microbial (e.g., bacterial) infection. The pharmaceutical compounds and / or compositions according to the invention are used in amounts that are effective in providing the desired therapeutic effect or result. The term administration or administering includes the delivery of a composition or one or more pharmaceutically active ingredients to a subject, including, for example, by any appropriate method, that serves to deliver the composition or its active ingredients or other pharmaceutically active ingredients to the site of infection. The method of administration may vary depending on several factors, such as, for example, the components of the pharmaceutical composition or the nature of the pharmaceutically active or inert ingredients, the site of potential or actual infection, the microorganism involved, the severity of the infection, the age and physical condition of the subject, and similar factors.Some non-limiting examples of ways to administer a pharmaceutically active composition or ingredient to a subject according to this invention include oral, intravenous, topical, intrarespiratory, intraperitoneal, intramuscular, parenteral, sublingual, transdermal, intranasal, aerosol, infraocular, intratracheal, intrarectal, vaginal, gene gun, dermal patch, eye drops, ear drops, or mouthwash. In the case of a pharmaceutical composition comprising more than one ingredient (active or inert), one way to administer such composition is by mixing the ingredients (e.g., in a suitable unit dosage form such as a tablet, capsule, solution, powder, and the like) and then administering the dosage form.Alternatively, the ingredients can also be administered separately (simultaneously or one after the other) provided that these ingredients reach beneficial therapeutic levels so that the composition as a whole provides a synergistic and / or desired effect. The term growth, as used herein, refers to the increase in the number of microorganisms and includes reproduction or expansion of the microorganism's population (e.g., bacteria). The term "growth" also includes the maintenance of the ongoing metabolic processes of a microorganism (e.g., a bacterium), including the processes that keep the microorganism alive. The term efficacy, as used herein, refers to the ability of a treatment, composition, or one or more pharmaceutically active ingredients to produce a desired biological effect in a subject. For example, the term antibacterial efficacy of an antibacterial composition or agent refers to the ability of the composition or agent to treat or prevent microbial (e.g., bacterial) infection in a subject. The term synergistic or synergy as used in this document refers to the interaction of two or more agents in such a way that their combined effect is greater than their individual effects. The term antibacterial agent, as used herein, refers to any substance, compound, or combination of substances or compounds capable of (i) inhibiting, reducing, or preventing the growth of bacteria; (ii) inhibiting or reducing the ability of a bacterium to produce infection in a subject; or (iii) inhibiting or reducing the ability of bacteria to multiply or remain infectious in the environment. The term antibacterial agent also refers to compounds capable of decreasing the infectivity or virulence of bacteria. The term beta-lactam antibacterial agent, as used herein, refers to compounds with antibacterial properties that contain a beta-lactam nucleus in their molecular structure. The term beta-lactamase, as used herein, refers to an enzyme, protein, or other substance that breaks down a beta-lactam ring. The term beta-lactamase includes enzymes produced by bacteria that can hydrolyze the beta-lactam ring into a beta-lactam compound, either partially or completely. The term beta-lactamase inhibitor, as used herein, refers to a compound capable of inhibiting the activity of one or more beta-lactamase enzymes, either partially or completely. βρο^ηη / ζζηζ / Β / γίΛΐ The term pharmaceutically inert ingredient, carrier, or excipient refers to a compound or material used to facilitate the administration of a compound, including, for example, to increase the compound's solubility. Typical, non-limiting examples of solid vehicles include starch, lactose, dicalcium phosphate, sucrose, kaolin, etc. Typical, non-limiting examples of liquid vehicles include sterile water, saline solution, buffers, nonionic surfactants, and edible oils such as peanut and sesame oils, etc. In addition, various adjuvants commonly used in the technique may be included. These and other similar compounds are described in the literature, for example, in the Merck Index (Merck & Company, Rahway, NJ). Considerations for the inclusion of various components in pharmaceutical compositions are described, for example, in Gilman et al. (Eds.) (1990), Goodman and Gilman's: The Pharmacological Basis of Therapeutics, 8th Ed., Pergamon Press., which is incorporated here as a reference, eleven in its entirety. The term "subject," as used herein, refers to a vertebrate or invertebrate, including a mammal. The term "subject" includes humans, animals, birds, fish, or amphibians. Typical, but not limited, examples of a subject include humans, cats, dogs, horses, sheep, cattle, pigs, lambs, rats, mice, and guinea pigs. The term "pharmaceutically acceptable derivative" as used herein refers to and includes any pharmaceutically acceptable salt, prodrug, metabolite, ester, ether, hydrate, polymorph, solvate, complex, enantiomer, or adduct of a compound described herein that, upon administration to a subject, is capable of providing (directly or indirectly) the parent compound. For example, the term "antibacterial agent" or a pharmaceutically acceptable derivative thereof includes all derivatives of the antibacterial agent (such as salts, prodrugs, metabolites, esters, ethers, hydrates, polymorphs, solvates, complexes, enantiomers, or adducts) that, upon administration to a subject, are capable of providing (directly or indirectly) the antibacterial compound. In general terms, a compound of Formula (I), or a stereoisomer or one of its pharmaceutically acceptable salts is provided; RPQfrnn / zznz / B / YiAi where: B is selected from: (a) (b) (c) (d) (θ) (f) (g) (h) (i) (j) (k) (l) hydrogen, halogen, alkyl Ci-Ce, OR1, NR1R2, SH, SR1, SOR1, SO2Ri, CHO, COOR1, CONRiR2, (m) CN, (n) (0) (P) heteroaryl, . heterocycloalkyl, 0 NHC(=NH)NH2; Ri and R2are each independently: (a) hydrogen, (b) Ci-C6 alkyl, optionally substituted with one or more substituents selected independently 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 selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, (d) three- to seven-membered heterocycloalkyl, optionally substituted with one or more substituents selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, (e) six- to fourteen-membered aryl, optionally substituted with one or more substituents selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, or (f) five- to fourteen-membered heteroaryl, optionally substituted with one or more substituents selected independently between CN, halogen, OH, NH2, COOH, CONH2, SH; M is selected from: (a) hydrogen, (b) alkyl Oι-Oθ, or (c) a pharmaceutically accepted salt-forming cation selected independently from Na, K or Ca. Typical, non-limiting examples of compounds according to the invention include: (2S,5R)-N-{[(2S,4R)-4-Methyl-pyrrolidin-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-Methylpyrrolidine-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-Met¡lp¡rrol¡din-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-Methyl-pyrrolidin-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-hydroxymethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; 2S,5R)-N-{[(2S,4S)-4-h¡drox¡methylpyrrol¡d¡n-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano- 2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-h¡droximethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-h¡droxymetilp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-Aminometil-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-Am¡nomet¡lp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-Am¡nomet¡lp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-Aminomet¡lp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-cyanomethyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane -2-carboxamida; RPQfrnn / zznz / B / Ywi 2S,5R)-N-{[(2S,4S)-4-C¡anomethylp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane- 2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-cyanomet¡lp¡rrolid¡n-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-can-2-yl]met-lox}-7-oxo-6-(sulfoox)-1,6diazabic-clo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-Fluoromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-Fluoromethyl-p¡rrol¡din-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-Fluoromethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-chloromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-chloromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-chloromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-chloromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-mercaptomethyl-pyrrolid¡n-2-yl]meth¡loxi}-7-oxo-6-(sulfooxy)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-mercaptomethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-mercaptomethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-mercaptomethyl-pyrrolidin-2-yl]methylox¡}-7-oxo-6-(sulfooxi)-1,6diazabicyclo[3.2.1]octane -2-carboxamida; βρο^ηη / ζζηζ / Β / γίΛΐ (2S,5R)-N-{[(2S,4R)-4-(Azirid¡n-1 -ylmeth¡l)-pyrrolid¡n-2-¡l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Azirid¡n-1 -ylmethyl)-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Azirid¡n-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Aziridin-1 -ilmetil)-pirrolidin-2-il]metiloxi}-7-oxo-6-(sulfooxi)-1,6diazabiciclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Azet¡d¡n-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Azet¡d¡n-1-¡lmetil)-p¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Azetidin-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Azet¡d¡n-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(pirrolidin-1 -ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(p¡rrol¡din-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-(pyrrolid¡n-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(p¡rrol¡d¡n-1-ylmetil)-pirrolidin-2-yl]metiloxi}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Piper¡d¡n-1-¡lrnet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-(P¡pend¡n-1-¡lmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Piper¡din-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Piperidin-1 -¡lmet¡l)-p¡rrol¡d¡n-2-yl]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Azepan-1 -ylmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-(Azepan-1 -ylmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxi)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Azepan-1 -ylmethyl)-p¡rrol¡din-2-yl]met¡loxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Azepan-1-¡lmethyl)-p¡rrolidin-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Piperazin-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Piperazin-1 -¡lmet¡l)-p¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxi)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Piperazin-1 -ylmethyl)-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Piperazin-1 -ylmet¡l)-p¡rrol¡din-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-(Morfolin-1 -ylmet¡l)-p¡rrolid¡n-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-(Morfolin-1-¡lmet¡l)-p¡rrolid¡n-2-¡l]metilox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-(Morfolin-1 -ylmethyl)-pyrrolidin-2-yl]methylox¡}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-(Morfol¡n-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-(T¡omorfolin-1-ylmet¡l)-p¡rrol¡d¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; βρο^ηη / ζζηζ / Β / γίΛΐ (2S,5R)-N-{[(2S,4S)-4-(Thiomorphol¡n-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Thiomorpholin-1 -ylmethyl)-pyrrolid¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Thiomorfolin-1 -ylmet¡l)-p¡rrol¡d¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrrol-1 -ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.1]octane-2-carboxam¡da; (2S,5R)-N-{[[(2S,4S)-4-(1 H-pyrrol-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfoxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-(1 H-pyrrol-1 -ylmethyl)-p¡rrol¡d¡n-2-yl] methyloxy}-7-oxo-6-(su Ifooxy)-1,6 diazabic¡clo[3.2.1]octane-2;- (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrrol-1 -lmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.da-2;-]caroboctane (2S,5R)-N-{[(2S,4R)-4-(1 H-imidazol-1 -¡lmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabicyclo[3.2.1-]caroboxamide-2; (2S,5R)-N-{[(2S,4S)-4-(1 H-imidazol-1 -ylmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.1;-]carboxane-da (2S,5R)-N-{[(2R,4S)-4-(1 H-imidazole-1 -lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2-2.1;-carboctane (2S,5R)-N-{[(2R,4R)-4-(1 H-imidazol-1 -¡lmet¡l)-pyrrolidine-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabicyclo[3.2.1]octano-2-carboxylate; (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrazol-1 -ylmethyl)-p¡rrol¡d¡n-2-¡l]meth¡loxy}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1]octano-carboxylate-2; (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrazol-1 -ylmet¡l)-p¡rrolidin-2-yl]methylox¡}-7-oxo-6-(sulfooxy)-1,6 diazabic¡chlo[3.2.1]octano-2-carboxy¡da; (2S,5R)-N-{[(2R,4S)-4-(1 H-pyrazol-1 -i lmethyl)-pyrrolide in-2-yl] methyloxy}-7-oxo-6-(su Ifooxi)-1,6 diazabic¡clo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrazol-1 -ylmethyl)-p¡rrol¡d¡n-2-¡l]meth¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1-octano-box-2-da¡]; (2S,5R)-N-{[(2S,4R)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pyrrolidin-2-yl]met¡loxi}-7-oxo-6-( sulfooxy)-1,6diazabicyclo[3.2.1]octano-2-carboxamide; βραι?ηη / ζζηζ / Β / γΐΛΐ (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pi rrolidin-2-yl] methy sulfo loxo6-¡6-7-yl diazabic¡chlo[3.2.1]octane-2-carboxxam¡da; (2S,5R)-N-{[[(2R,4S)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pi rrolidin-2-yl] methy loxi}-7-oxo-6-( sulfoox¡)-1,6 diazabic¡clo[3.2.1-]carboxane-da (2S,5R)-N-{[(2R,4R)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pyrrolidin-2-yl] methyloxy}-7-oxo-6-( sulfoox¡)-1,6 diazabic¡clo[3.2.1]carboxane¡da-2-2; (2S,5R)-N-{[(2S,4R)-4-(1 H-1,2,4-triazol-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-( sulfoxy)-1,6 diazabicyclo[3.2.1]octamide;2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,4-triazol-1 -ylmethyl)-pi rrolidin-2-yl] metí loxi}-7-oxo-6-( sulfoox¡)-1,6diazabic¡clo[3.2.1]carboxanoda-2-2; (2S,5R)-N-{[[(2R,4S)-4-(1 H-1,2,4-triazol-1 -ylmethyl)-pi rrolidin-2-yl] metí loxi}-7-oxo-6-( sulfoox¡)-1,6diazabic¡clo[3.2.1]carboxanoda-2-2; (2S,5R)-N-{[(2R,4R)-4-(1 H-1,2,4,triazol-1 -ylmethyl)-pi rrolidin-2-yl] metí loxi}-7-oxo-6-( sulfoox¡)-1,6 diazabicyclo[3.2.1]caroboxamide;2- (2S,5R)-N-{[(2S,4R)-4-(1 H-tetrazol-1 -ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6 diazabic¡clo[3.2.da-2-]caroboctane (2S,5R)-N-{[(2S,4S)-4-(1 H-tetrazol-1 -ylmet¡l)-p¡rrol¡d¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6 diazabic¡clo[3.2.1;-]carboxane-da (2S,5R)-N-{[(2R,4S)-4-(1 H-tetrazol-1 -ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.da-2;-]caroboctane (2S,5R)-N-{[(2R,4R)-4-(1 H-tetrazol-1-ylmet¡l)-p¡rrol¡d¡n-2-il]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.1]carboxane ¡2-2-; (2S,5R)-N-{[(2S,4R)-4-(2H-tetrazoly-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabic¡clo[3.2.1]octane-2-carboxaxam¡da; (2S,5R)-N-{[[(2S,4S)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methylose}-7-oxo-6-(sulfoxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-ylmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.1]carboxanoda-2-; (2S,5R)-N-{[(2R,4R)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfoox¡)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; 2S,5R)-N-{[(2S,4S)-4-Carbam¡m¡m¡domethyl-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane- 2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-Carbaιn¡m¡domet¡l·p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane ;2-carboxamide (2S,5R)-N-{[(2R,4S)-4-Carbamim¡domet¡lp¡rrol¡din-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-Carbam¡midomethyl-pyrrolid¡n-2-yl]methylox¡}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane -2-carboxamide; or a stereoisomer or a pharmaceutically acceptable salt thereof. In some embodiments, typical non-limiting examples of compounds according to the invention include: Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Methyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfoxy)-1,6diazabicyclo[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Methyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Methyl-pyrrolidin-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡cyclo[3.2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Methyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Hydroxymethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfoxy)-1,6diazabicyl[3.2. 1 ]octane-2-carboxamide; Sodium salt of 2S,5R)-N-{[(2S,4S)-4-Hidroximethylpyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabiciclo[3.2.1 ]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-h¡droximethylp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. 1 ]octane-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-H¡drox¡met¡lp¡rrolid¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. 1 ]octane-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-Am¡nometil-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2. sal de trifluoroacetato de 1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4S)-4-Am¡nometil-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. sal de trifluoroacetato de 1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Am¡nomethyl-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. 1]octane-2-carboxamid trifluoroacetate salt; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-Aminomet¡lp¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. sal de trifluoroacetato de 1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-C¡anometil-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. 1 ]octano-2-carboxamida; Sodium salt of 2S,5R)-N-{[(2S,4S)-4-Cyanomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabiciclo[3.2.1 ]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-C¡anomethyl-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. 1 ]octane-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-C¡anometil-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2. 1 ]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-Fluorometil-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2. 1 ]octano-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-Fluoromethyl-pyrrolidin-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2] sodium salt. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Fluoromethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyl[3.2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Fluoromethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-Chloromet¡lp¡rrol¡din-2-yl]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2] sodium salt. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Chloromethyl-pyrrolidine-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicchloro[3.2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Chloromethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicchloro[3.2. 1 ]octane-2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-Chloromethyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2] sodium salt. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-mercaptomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2. 1 ]octane-2-carboxamide; RPQfrnn / zznz / B / YiAi Sodium salt of (2S,5R)-N-{[(2S,4S)-4-mercaptomethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyl[3.2. 1 ]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-mercaptomethyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2] sodium salt. 1 ]octane-2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-mercaptomethyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2] sodium salt. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Aziridin-1-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,4S)-4-(Azirid¡n-1 -ylmethyl)-p¡rroldin-2-yl]methyloxy}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡chlo[3.2.1]octano-carboxylate-2-da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azirid¡n-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)1, 6-diazabic clo[3-octa-2-cartamida.2]; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Aziridin-1 -¡lmethyl)-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-(Azetidin-1 -¡lmethyl)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡chlo[3.2-octaamida.2]; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Azetidin-1 -ilmet¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡clo[32-octa. Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azetidin-1 -¡lmethyl)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)1, 6-diazabicyclo[3.2.1-octano-card]; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Azetidin-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡chlo[3.2.1-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(pyrrolidin-1-ylmethyl)-pyrrolidine-2-yl]methyloxy}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(p¡rroldin-1-meth¡l)-p¡rrol¡n-2-¡l]meth¡l ox¡}-7-oxo-6(sulfoox¡)-1,6-diazab¡c¡chlo[3.2.1]octane-2-carboxamide; Sodium salt of (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; RPQfrnn / zznz / B / YiAi Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(P¡perid¡n-1-¡lmet¡l)-p¡rroldin-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazab¡c¡clo[3.2-oct. Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(P¡per¡d¡n-1-¡met¡l)-p¡rrol¡n-2-¡l]meth¡l x¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(P¡pend¡n-1-ilmet¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2. Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(P¡peridin-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)-l, 6-diazab¡cyclo[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Azepan-1 -ylmethyl)-p¡rrolidin-2-¡l]methyloxy}-7-oxo-6-(suIphooxy)1, 6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Azepan-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)1, 6-diazabic chlo[3.2.1]-octano-cartamine; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azepan-1 -¡lmethyl)-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-(Azepan-1 -¡lmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(P¡perazin-1-¡lmet¡l)-p¡rrol¡d¡n-24l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sodica de (2S,5R)-N-{[(2S,4S)-4-(P¡perazin-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(P¡peraz¡n-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabiciclo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Piperazin-1-ylmethyl)-pyrrolidin-24l]methyloxy}-7-oxo-6(sulfoox¡)-1,6-diazab¡c¡clo[3.2.1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-(Morfolin-1 -ilmetil)-p¡rrol¡din-2-il]met¡loxi}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2S,4S)-4-(Morfolin-1 -ilmetil)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)1, 6-d¡azabiciclo[3.2.1]octano-2-carboxam¡da; fiPQfrnn / zznz / e / YiAi Sal sódica de (2S,5R)-N-{[(2R,4S)-4-(Morfolin-1 -ilmetil)-pirrolidin-2-¡l]metiloxi}-7-oxo-6-(sulfooxi)1, 6-diazabiciclo[3.2.1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-(Morfolin-1 -ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)1, 6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-(T¡omorfolin-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2S]4S)-4-(T¡omorfolin-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabiciclo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2R,4S)-4-(Tiomorfolin-1-ilmetil)-pirrolidin-2-il]metiloxi}-7-oxo-6(sulfooxi)-l, 6-diazab¡ciclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(T¡omorpholin-1-¡lmet¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡²⁺²-octano-octano-octano-octano-ocda-2 Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrrole-1-ylmethyl)-pyrrol¡n-2-yl]meth¡loxy}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octano-carboxy-2-da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrrole-1-ylmethyl)-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-(1 H-pyrrole-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-d¡azabicyclo[3.2.1]octano-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrrol-1 -ylmethyl)-p¡rrolidin-2-yl]meth¡loxy}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octano-2-carboxam; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-midazol-1-lmethl)-p¡rrol¡n-2-l]methlox¡}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-midazol-1-lmethl)-p¡rrol¡n-2-l]methlox¡}-7-oxo-6(sulfooxy)- 1,6-d¡azabicyclo[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1 H-imidazol-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-midazol-1-lmethl)-p¡rrol¡n-2-l]methlox¡}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrazol-1-lmethl)-p¡rrol¡n-2-l]methlox¡}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrazol-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabicyclo[3.2.1]octane-2-carboxamide; fiPQfrnn / zznz / e / YiAi Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1 H-pyrazol-1-ilmet¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfooxy)- 1,6-diazab¡c¡c¡c¡c¡c¡c¡¡¡¡¡¡¡C¡¡¡¡¡¡Cloc¡¡¡¡¡¡²-²-²-²-² Sal sódica de (2S,5R)-N-{[(2R,4R)-4-(1 H-pirazol-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxi)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-1,2,3-tnazol-1-¡lmethyl)-p¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,3-triazol-1-ilmetil)-p¡rrolidin-2-il]metiloxi}-7-oxo- 6(sulfooxi)-l ,6-diazabiciclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1,2,3-tr¡azol-1-¡lmet¡l)-p¡rrolid¡n-2-¡l]methylox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-(1H-1,2,3-triazol-1-¡lmetil)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-(1H-1,2,4-tr¡azol-1-¡lmetil)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfooxi)-l ,6-diazabiciclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,4-triazol-1-¡lmet¡l)-pyrrol¡d¡n-2-¡l]methylox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1,2,4-tr¡azol-1-¡lmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-(1H-1,2,4,tr¡azol-1-ilmetil)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-tetrazol-1-¡lmet¡l)-p¡rrol¡d¡n-2-il]met¡lox¡}-7-oxo-6(sulfooxy)- 1,6-diazabiciclo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2S,4S)-4-(1 H-tetrazol-1-ylmetil)-pirrolidin-2-il]metiloxi}-7-oxo-6(sulfooxi)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2R,4S)-4-(1 H-tetrazol-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6(sulfooxi)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-tetrazol-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6(sulfooxy)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(2H-tetrazoly-2-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabiciclo[3.2.1]octano-2-carboxamida; fiPQfrnn / zznz / e / YiAi Sal sódica de (2S,5R)-N-{[(2S,4S)-4-(2H-tetrazol-2-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxi)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxi)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-(2H-tetrazol-2-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxi)- 1,6-diazabiciclo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Carbamimidomethyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)1,6-diazabiciclo[3.2. 1]octane-2-carboxamida; Salt sódica de (2S,5R)-N-{[(2S,4R)-4-Carbam¡midometil-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)1,6-diazabic¡clo[3.2. 1]octano-2-carboxamida; Salt sodium de (2S,5R)-N-{[(2R,4S)-4-Carbam¡m¡domet¡lp¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)1,6-diazabic¡clo[3.2. 1]octane-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-Carbam¡m¡domet¡lp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxi)-l ,6-diazabiciclo[3.2. 1]octano-2-carboxamida; or an estereoisomer of mismo. βροι?ηη / ζζηζ / Β / γΐΛΐ Typical examples not limiting the calculations included with the invention: βροι?ηη / ζζηζ / Β / γΐΛΐ βροι?ηη / ζζηζ / Β / γΐΛΐ β?αι?ηη / ζζηζ / Β / γΐΛΐ The compounds of the invention can be prepared according to the general procedure provided in Scheme 1 and Scheme 2. Individual stereoisomers can be prepared using appropriate starting materials and reagents. A person skilled in the art would appreciate that the described methods can be varied and / or further optimized to provide the desired and related compounds. Scheme I Scheme 2 A compound of Formula (XII) is typically reacted with a sodium salt of (2S, 5R)-6-benzyloxy-7-oxo-1,6-diaza-bichloro[3.2.1]octane-2-carboxylic acid (XIII) to give a compound of Formula (XIV). The compound of Formula (XIV) is then converted to a compound of Formula (XV) in the presence of a suitable debenzylation agent. Typical, but not limited, examples of suitable debenzylation agents include hydrogen gas in the presence of a transition metal catalyst such as palladium on carbon. The compound of Formula (XV) is then converted to a compound of Formula (XVI) in the presence of a suitable sulfonating agent. Typical, but not limited, examples of suitable sulfonating agents include sulfur trioxide complex and dimethylformamide. The sulfonation reaction is followed by treatment with tetrabutylammonium acetate to give a compound of Formula (XVI).The compound of Formula (XVI) is converted to a compound of Formula (I) in the presence of a suitable deprotecting agent. Typical, but not limited to, examples of suitable deprotecting agents include trifluoroacetic acid. A wide variety of other reagents that can induce these functional transformations may also be used. More specifically, some compounds according to the invention were isolated as zwitter ions by treating the intermediate compound (XVI) with trifluoroacetic acid, in a diazabiclo[3.2.1]octane-2-carboxamide solvent, or a pharmaceutically acceptable stereoisomer or salt thereof, and (b) at least one antibacterial agent or a pharmaceutically acceptable derivative thereof. In some embodiments, pharmaceutical compositions comprising: (a) (2S, 5R)-N-{[(2S, 4R)-4-methylpyrrolidine-2-1]methyloxi}-7-oxo-6-(sulfooxi)-1,6diazabicilo[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof, and (b) one or more of cefixime, cefpodoxime, ceftibuten, cefuroxime or a pharmaceutically acceptable salt thereof. In some embodiments, pharmaceutical compositions comprising: (a) ((2S,5R)-N-{[(2S,4S)-4-Methylpyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof, and (b) one or more of cefixime, cefpodoxime, ceftibuten, cefuroxime, or a pharmaceutically acceptable salt thereof. In some other embodiments, methods are provided for treating or preventing a bacterial infection in a subject, said method comprising administering to said subject pharmaceutical compounds or compositions according to the invention. In some other modalities, methods are provided for treating or preventing 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 some embodiments, methods are provided for treating or preventing 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 one of its pharmaceutically acceptable salts. In some embodiments, the compounds and / or compositions according to the invention are used to treat or prevent bacterial infections. In some embodiments, the use of a compound that is (2S, 5R)-N{[(2S, 4R)-4-methylpyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide, or a stereoisomer or pharmaceutically acceptable salt thereof, is provided for the treatment or prevention of bacterial infections. In some embodiments, the use of a compound that is (2S,5R)-N{[(2S,4S)-4-Methylpyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfox)-1,6-diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof, is provided for the treatment or prevention of bacterial infections. βραι?ηη / ζζηζ / Β / γΐΛΐ In some embodiments, a compound that is (2S, 5R)-N-{[(2S, 4R)-4-methylpyrrolidine2-1]methyloxy}-7-oxo-6-(sulfox)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide, or a stereoisomer or one of its pharmaceutically acceptable salts, is used in the preparation of a medicament to treat or prevent a bacterial infection. In some embodiments, a compound that is (2S,5R)-N-{[(2S,4S)-4-methyl-pyrrolidine-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or pharmaceutically acceptable salt thereof, is used in the preparation of a medicament to treat or prevent a bacterial infection. In some embodiments, a method is provided for treating or preventing bacterial infection in a subject, said method comprising administering to said subject a compound that is (2S, 5R)-N-{[(2S, 4R)-4-methylpyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof. In some embodiments, a method is provided for treating or preventing bacterial infection in a subject, said method comprising administering to said subject a compound that is (2S,5R)-N-{[(2S,4S)-4-methyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof. In some embodiments, a method is provided for treating or preventing bacterial infection in a subject, said method comprising administering to said subject a pharmaceutical composition comprising (2S, 5R)-N-{[(2S, 4R)-4-methylpyrrolidine-2-yl]methyloxy}-7oxo-6-(sulfooxy)-1,6-diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof. In some embodiments, a method is provided for treating or preventing bacterial infection in a subject, said method comprising administering to said subject a pharmaceutical composition comprising (2S,5R)-N-{[(2S,4S)-4-methylpyrrolidi-2-yl]methyloxy}-7oxo-6-(sulfooxy)-1,6-diazabicyl[3.2.1]octane-2-carboxamide, or a stereoisomer or a pharmaceutically acceptable salt thereof. The compositions and methods according to the invention use compounds of formula (I) or a pharmaceutically acceptable stereoisomer or salt thereof, in combination with at least one antibacterial agent or a pharmaceutically acceptable derivative thereof. A wide variety of antibacterial agents may be used in combination with the compounds according to the invention. Antibacterial agents are often classified according to their structure or mode of action. Typical and non-limiting examples of antibacterial agents include those belonging to a group of antibacterial agents such as ansamycins, carbacephems, carbapenams, carbapenems, cephalosporins, cephamycins, cephemes, lincosamides, lipopeptides, macrolides, ketolides, monobactams, nitrofurans, oxacephems, oxapenams, oxazolidinones, penams, penems, penicillins, polypeptides, quinolones, sulfonamides, tetracyclines, and the like. In some forms, the antibacterial agent is a beta-lactam antibacterial agent. Typical, but not limited to, examples of beta-lactam antibacterial agents include those commonly known as Carbacephems, Carbapenams, Carbapenems, Cephalosporins, Cephamycins, Cephemas, Monobactams, Oxacephemes, Oxapenas, Penams, Penems, Penicillins and the like. Typical, but not limited to, examples of antibacterial agents include cefacetrile, cefaclor, cefadroxil, cephalexin, cephaloglycine, cephalonium, cephaloridine, cephalothin, cefamandole, cefapirin, cefatrizine, cefazaflur, cefazedone, cefazolin, cefbuperazone, cefcapen, cefclidine, cefdaloxime, cefdinir, cefditoren, cefepime, cefetamet, cefixime, cefluprenam, cefmenoxime, cefmetazole, cefminox, cefodizime, cefonicid, cefoperazone, ceforanide, cefoselis, cefotaxime, cefotetan, cefotiam, cefovecin, cefoxitin, cefozopran, cefpimizole, cefpiramide, cefpirome, and cefpodiloxime. cefquinome, cefradine, cefroxadine, cefsulodine, ceftaroline, ceftazidime, cefteram, ceftezole, ceftibuten, ceftiofur, ceftiolene, ceftizoxime, ceftobiprol, ceftolozane, ceftriaxone, cefuroxime, cefuzonam, cephaloridine, cefradine, ceftolozane (CXA-101), cefiderocol, flomoxef, latamoxef, loracarbef, moxalactam and the like. In some formulations, the antibacterial agent is at least one selected from cefaclor, cefadroxil, cephalexin, cefdinir, cefixime, cefpodoxime, cefprozil, cephradine, ceftibuten, cefuroxime, loracarbef, or a pharmaceutically acceptable derivative thereof. In some formulations, the antibacterial agent is at least one selected from cefpodoxime axetil, cefpodoxime proxetil, ceftibuten, cefuroxime, cefuroxime axetil, cefixime, or a pharmaceutically acceptable derivative thereof. Typical, but not limited, examples of aminoglycoside antibacterial agents include amikacin, gentamicin, kanamycin, neomycin, netilmicin, tobramycin, paromomycin, arbekacin, streptomycin, apramycin, plazomicin, and the like. Typical, but not limited, examples of ansamycin antibacterial agents include geldanamycin, herbymycin, and similar substances. βροι?ηη / ζζηζ / Β / γΐΛΐ Typical, but not limited, examples of carbapenem antibacterial agents include ertapenem, doripenem, imipenem, meropenem, panipenem, biapenem, tebipenem, lenapenem, tomopenem, and the like. Typical, but not limited, examples of lincosamide antibacterial agents include clindamycin, lincomycin, and similar drugs. Typical, but not limited, examples of macrolide antibacterial agents include azithromycin, clarithromycin, dirithromycin, erythromycin, roxithromycin, troleandomycin, telithromycin, spectinomycin, solithromycin, nafithromycin, and the like. Typical non-limiting examples of monobactam antibacterial agents include aztreonam, tigemonam, carumonam, nocardicin A, LYS-228, AIC499, sulfazecin, monosulfactam 0073, tabtoxin, and the like. Typical, but not limited, examples of nitrofuran antibacterial agents include furazolidone, nitrofurantoin, and similar substances. Typical non-limiting examples of penicillin antibacterial agents include amoxicillin, ampicillin, azlocillin, carbenicillin, cloxacillin, dicloxacillin, flucloxacillin, mezlocillin, methicillin, nafcillin, oxacillin, penicillin g, penicillin v, piperacillin, temocillin, ticarcillin, and similar agents. Typical, but not limited to, examples of polypeptide antibacterial agents include bacitracin, colistin, polymyxin B, and the like. Typical, but not limited, examples of pleuromutilin antibiotics include lefamulin and similar drugs. Typical non-limiting examples of quinolone antibacterial agents include ciprofloxacin, enoxacin, gatifloxacin, levofloxacin, lomefloxacin, moxifloxacin, nalidixic acid, levonadifloxacin, norfloxacin, ofloxacin, trovafloxacin, grepafloxacin, sparfloxacin, temafloxacin, fleroxacin, pefloxacin, sitafloxacin, and the like. Typical, but not limited, examples of sulfonamide antibacterial agents include mafenide, sulfonamidocrysoidine, sulfacetamide, sulfadiazine, sulfamethizole, sulfamethoxazole, sulfasalazine, sulfisoxazole, trimethoprim, and the like. Typical, but not limited, examples of tetracycline antibacterial agents include demeclocycline, doxycycline, minocycline, oxytetracycline, tetracycline, tigecycline, and the like. Typical and non-limiting examples of oxazolidinone antibacterial agents include tedizolid, linezolid, ranbezolid, torezolid, radezolid, (5S)-N-{3-[3,5-difluoro-4-(4-hydroxy(4-methoxymethyl)-pyridinium-141)phenyl]-2-oxo-oxazolidine-5-methyl}-acetamide and the like. βροι?ηη / ζζηζ / Β / γΐΛΐ In general, the compounds, pharmaceutical compositions, and methods described herein are useful for treating and / or preventing bacterial infections. Advantageously, the compounds, compositions, and methods described herein are also effective for treating or preventing infections caused by bacteria that are considered less susceptible or not susceptible to one or more known antibacterial agents or their compositions. Some non-limiting examples of such bacteria that are known to have developed resistance to various antibacterial agents include Acinetobacter, E. coli, Pseudomonas aeruginosa, Staphylococcus aureus, Enterobacter, Klebsiella, Citrobacter, and similar bacteria.Other non-limiting examples of infections that can be treated or prevented using the compounds, compositions and / or methods according to the invention include skin and soft tissue infections, febrile neutropenia, urinary tract infection, intra-abdominal infections, respiratory tract infections, pneumonia (nosocomial), bacteremia, meningitis, surgical infections, etc. Surprisingly, the compounds, compositions, and methods according to the invention are also effective in treating and / or preventing bacterial infections caused by bacteria that produce one or more beta-lactamase enzymes. The ability of the compounds, compositions, and / or methods according to the present invention to treat such bacteria resistant to typical beta-lactam antibiotics represents a significant improvement in the art. In general, compounds of formula (I) or a pharmaceutically acceptable stereoisomer or salt thereof according to the invention are also useful for increasing the antibacterial efficacy of an antibacterial agent in a subject. The antibacterial efficacy of one or more antibacterial agents can be increased, for example, by co-administering said antibacterial agent or a pharmaceutically acceptable derivative thereof with a compound of formula (I) or a pharmaceutically acceptable stereoisomer or salt thereof according to the invention. In some embodiments, a process is provided for the preparation of a compound of Formula (I), or a stereoisomer, or a pharmaceutically acceptable salt thereof; |Formula (I) RPQfrnn / zznz / B / YiAi where: B is selected from: (a) hydrogen, (b) halogen, (c) alkyl Ci-Ce , (d) OR1, (θ) NR1R2, (f) (g) (h) (¡) (j) (k) (l) (m) (n) (0) (P) SH, SR1, SOR1, SO2Ri, CHO, COOR1, CONRiR2, CN, heteroaryl, heterocycloalkyl, 0 NHC(=NH)NH2; Ri and R2son each independently: (a) hydrogen, (b) Ci-Ce alkyl, optionally substituted with one or more substituents selected independently 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 selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, (d) three- to seven-membered heterocycloalkyl, optionally substituted with one or more substituents selected independently from CN, halogen, OH, NH2, COOH, CONH2 or SH, (e) six- to fourteen-membered aryl, optionally substituted with one or more substituents selected independently 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) Ci-Ce alkyl, or (c) a pharmaceutically accepted salt-forming cation selected independently from Na, K, or Ca. Which includes: (a) reacting a compound of formula (XII) with a compound of formula (XIII) to obtain a compound of formula (XIV); (b) convert a compound of formula (XIV) into a compound of formula (XV); Formula (XV; (c) convert a compound of formula (XV) into a compound of formula (XVI); and SO NBu Formula (XVl·: (d) convert a compound of formula (XVI) into a compound of formula (I). In some embodiments, the compound of Formula (XIV) is obtained by reacting a compound of Formula (XII) with the sodium salt of (2S, 5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (XIII) in the presence of suitable reagents. Typical, but not limited, examples of such reagents include 1-hydroxybenzotriazole (HOB1), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HC1), and N-methylmorpholine (NMM). In some other embodiments, the compound of Formula (XIV) is converted to a compound of Formula (XV) in the presence of a suitable debenzylation agent. Typical, but not limited to, examples of suitable debenzylation agents include hydrogen gas in the presence of a transition metal catalyst such as palladium on carbon. In some other embodiments, the compound of Formula (XV) is converted to a compound of Formula (XVI) in the presence of a suitable sulfonating agent followed by treatment with tetrabutylammonium acetate. Typical, but not limited to, examples of suitable sulfonating agents include sulfur trioxide complex and dimethylformamide. The sulfonation reaction is followed by treatment with tetrabutylammonium acetate to obtain a compound of Formula (XVI). In some other embodiments, the compound of Formula (XVI) is converted into a compound of Formula (I) in the presence of a suitable deprotecting agent. Typical, but not limited, examples of suitable deprotecting agents include trifluoroacetic acid. More specifically, some compounds according to the invention were isolated as zwitter ions by treating the intermediate compound (XVI) with trifluoroacetic acid in a suitable solvent (such as dichloromethane, chloroform, or acetonitrile) at a temperature ranging from approximately -10°C to -10°C to 15°C for approximately 1 to 14 hours, especially when A in the intermediate compound (XVI) contained an amine functional group protected with tert-butoxycarbonyl. Some compounds according to the invention were isolated as zwitter ions by treating the intermediate compound (XVI) with tetrabutylammonium fluoride followed by trifluoroacetic acid in a suitable solvent, especially when A in the intermediate compound (XVI) contained a hydroxy function protected by tert-butyldimethylsilyl (TBDMS) and an amine function protected by tert-butoxycarbonyl (BOC). Some other compounds according to the invention were isolated as a corresponding sodium salt by passing the intermediate compound (XVI) through a suitable sodium ion exchange resin in a tetrahydrofuran-water mixture followed by vacuum evaporation of the solvent. A wide variety of other reagents can be used to bring about these functional transformations. It will be readily apparent to a person skilled in the art that various substitutions and modifications can be made to the invention described herein without departing from the scope and spirit of the invention. For example, those skilled in the art will recognize that the invention can be implemented using a variety of different compounds within the generic descriptions provided. EXAMPLES The following examples illustrate the embodiments of the invention that are currently the most widely known. However, it should be understood that the following are merely examples or illustrations of the application of the principles of the present invention. Those skilled in the art can devise numerous modifications and alternative compositions, methods, and systems without departing from the spirit and scope of the present invention. The appended claims purport to cover such modifications and arrangements. Therefore, although the present invention has been described in detail above, the following examples provide further details regarding what are currently considered to be the most practical and preferred embodiments of the invention. Example 1 (2S,5R)-N-{[(2S,4R)-4-methylpyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide (1) H 0 βραι?ηη / ζζηζ / Β / γΐΛΐ J---Π 0 \ BEAR H l(the) Step 1: Synthesis of 1-tert-butyl 2-methyl (2S, 4R)-4-[(methylsulfonyloxy) methyl]pyrrolidine-1,2dicarboxylate (V1a). Triethylamine (4.29 mL, 30.55 mmol) was added to a solution of 1-tert-butyl 2-methyl (2S,4R)-4-hydroxymethylpyrrolidine-1,2-dicarboxylate (Via) (5.0 g, 19.28 mmol; prepared following similar procedures described in the PCT International Application published under number WO 2013 / 075029A1) in 50 mL of dichloromethane, in one batch, and the resulting solution was cooled to -10°C. To this cooled solution, methanesulfonyl chloride (2.65 g, 23.13 mmol) was added dropwise with stirring. The reaction was monitored by thin-layer chromatography (TLC) (ethyl acetate:hexane 1:1). After the starting material was completely consumed, water (50 ml) was added to the reaction mixture and stirred for another 0.5 hours. The organic layer was separated, washed with water (20 ml), and dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain a yellowish residue.The residue was dried under high vacuum and used as such for the next reaction without any further purification (6.5 g, 99% yield). Analysis: Mass: 338.2 (M+H) for MW: 337.39; MF: C13H23NO7S Step 2: Synthesis of 1-tert-butyl 2-methyl (2S, 4R)-4-iodomethylpyrrolidine-1,2-dicarboxylate (Villa). 1-tert-butyl 2-methyl (2S, 4R)-4-[(methylsulfonyloxy)methyl]pyrrolidine-1,2-dicarboxylate (VIa) (6.50 g, 19.26 mmol) was added to a solution of acetone (65 mL) and sodium iodide (7.65 g, 51.04 mmol) at 25°C. The reaction mixture was heated under reflux. The reaction was monitored by TLC (ethyl acetate:hexane 1:1). After complete consumption of the starting material, the reaction mixture was filtered under suction, and the residue was washed with an additional 20 mL of acetone. The combined filtrates were evaporated under reduced pressure, and the resulting residue was dissolved in 100 mL of ethyl acetate. The ethyl acetate layer was washed with 100 mL of acetone solution. A sodium thiosulfate solution was followed by 50 ml of saturated brine solution. The ethyl acetate layer was dried on sodium sulfate and the solvent was evaporated under reduced pressure to obtain a yellowish oil as a residue.The residue was dried under high vacuum to obtain 1-tere-butyl 2-methyl (2S, 4R)-4-iodomethylpyrrolidine-1,2-dicarboxylate (Villa) (6.0 g, 84.0% yield) and was used as such in the following reaction without further purification. Analysis: Mass: 370.5 (M+H) for MW: 369.20; MF: C12H20INO4 fiPQfrnn / zznz / e / YiAi Step 3: Synthesis of 1-tert-butyl 2-methyl (2S, 4R)-4-methylpyrolidin-1,2-dicarboxylate (IXa). Pd at 10% / C (0.6 g) was added to a solution of 1-tert-butyl 2-methyl (2S, 4R)-4-iodomethylpyrrolidine-1,2-dicarboxylate (Villa) (6.0 g, 16.89 mmol) in methanol (60 mL). The solution was hydrogenated at 50 psi at 25–30°C, and the progress of the reaction was monitored by thin-layer chromatography (TLC) (ethyl acetate:hexane 1:1). After complete consumption of the starting material, the reaction mixture was filtered through a Celite bed, and the residue was washed with methanol (2 × 10 mL). The solvent from the combined filtrate was evaporated under reduced pressure to obtain 1-tere-butyl (IXa) 2-methyl (2S, 4R)-4-methylpyrrolidine-1,2-dicarboxylate (2.5 g, 60.8%). Analysis: Mass: 244.9 (M+H) for MW: 243.31; MF: C12H21NO4; 1H-NMR: (400MHz, CDCI3): δ 3.73 (s, 3 H), 3.48 (s, 1 H), 3.01-2.96 (m, 1H), 2.41 -2.36 (m, 1 H), 2.26 - 2.21 (m, 1 H), 1.81-1.79 (m, 1 H), 1.59 - 1.51 (m, 1H), 1.40 (s, 9H), 1.06 (s, 3H). Step 4: Synthesis of (2S, 4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate of tere-butyl (Xa). Lithium aluminum hydride (0.849 g, 22.36 mmol) was added to a clean, dry flask under an argon atmosphere. The flask was cooled to -10°C, and tetrahydrofuran (25 mL) was added slowly through an addition funnel. After stirring for 0.5 hours, a solution of 1-tert-butyl-2-methyl(2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate (IXa) (4.94 g, 20.33 mmol) in tetrahydrofuran (25 mL) was added dropwise to the mixture. The reaction was monitored by thin-layer chromatography (TLC) (ethyl acetate:hexane 1:4). After complete consumption of the starting material, moist sodium sulfate was added slowly. The reaction mass was stirred at room temperature for four hours and filtered through a Hyflo bed. The residue was washed with ethyl acetate (50 mL). The filtrate was evaporated under reduced pressure to remove all solvents. The concentrated mass was diluted again with ethyl acetate (50 mL) and the solution was washed with saturated brine (20 mL).The organic layer was dried on sodium sulfate and evaporated under reduced pressure on a rotary evaporator to obtain a yellowish residue. The residue was dried under high vacuum to obtain (2S, 4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate (Xa) (3.8 g, 87%) and was used as such in the following reaction, without further purification. Analysis: βροι?ηη / ζζηζ / Β / γΐΛΐ Mass: 215.9 (M+H) for MW: 215.29; MF: C11H21NO3; 1H-NMR: (500 MHz, CDCI3): δ 4.55 (bs, 1 H), 4.06 (bs, 1 H), 3.63 - 3.60 (m, 2 H), 3.48 - 3.46 (m, 1 H), 2.97 - 2.93 (m, 1 H), 2.29 - 2.25 (m, 1 H), 1.69 - 1.64 (m, 2 H), 1.47 (s, 9 H), 1.02 (d, J = 5 Hz, 3 H). Step 5: Synthesis of tert-butyl (2S, 4R)-2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-1l)oxy]methyl}-4-methylpyrrolidine-1-carboxylate (Xla). Diisopropyl azodicarboxylate (4.2 mL, 21.20 mmol) was added to a tetrahydrofuran solution (40 mL) containing tert-butyl (2S, 4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate (Xa) (3.8 g, 17.67 mmol), triphenylphosphine (5.55 g, 21.20 mmol), and N-hydroxyphthalimide (2.88 g, 17.67 mmol) with stirring at room temperature (exothermic reaction, temperature controlled by ice water). After the addition, stirring was continued for 4 hours at room temperature. Thin-layer chromatography (TLC) at this stage indicates completion of the reaction. The resulting mixture was then concentrated under reduced pressure to produce an oily residue, which was purified by column chromatography using silica gel (mesh size 60-120).Elution with a v / v mixture of ethyl acetate:hexane (1:3) as eluent and evaporation of the combined fractions yielded tert-butyl (2S, 4R)-2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-1l)oxy]methyl}-4-methylpyrrolidine-1-carboxylate (Xla) (5.96 g, 92%), as an oil. Analysis: Mass: 361.2 (M+H) for MW: 360.40; MF: C19H24N2O5; 1H-NMR: (400 MHz, CDCI3): δ 7.84 - 7.75 (m, 4 H), 4.38 - 4.30 (m, 1 H), 4.17 - 3.95 (m, 2 H), 3.56 - 3.49 (m, 1 H), 2.92 - 2.83 (m, 1 H), 2.43 - 2.38 (m, 2 H), 1.74- 1.69 (m, 1 H), 1.40 (s, 9 H), 1.09 (d, J = 8 Hz, 3 H). Step 6: Synthesis of (2S,4R)-2-[(aminooxy)methyl]-4-methylpyrrolidine-1-carboxylate of tere-butyl (XI1). Hydrazine hydrate (1.24 mL, 24.83 mmol) was added to the solution of (2S,4R)-2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy tert-butyl]methyl}-4-methylpyrrolidine-1-carboxylate (X1) (5.96 g, 16.55 mmol) in dichloromethane (90 mL), with stirring, at room temperature. Stirring was continued for a further 2 hours, and the reaction was monitored by thin-layer chromatography (TLC) (ethyl acetate:hexane 1:3). After complete consumption of the starting material, the volatiles were removed under reduced pressure to obtain a yellowish residue. The residue was dried under reduced pressure (4 mmHg) to obtain (2S,4R)-2-[(aminooxy)methyl]-4-methylpyrrolidine-1 fiPQfrnn / zznz / e / YiAi tere-butyl carboxylate (Xlla) (3.1 g, 82%) and used as such in the following reaction without further purification. Analysis: Mass: 229.7 (MH) for MW: 230.30; MF: C11H22N2O3; Step 7: Synthesis of (2S, 5R)-6-benzyloxy-N-{[(2S, 4R)-4-methylpyrrolidine-1 tert-butylcarboxylate]methoxy}-7-oxo-1,6-diazabicyl[3.2.1 ]octane-2-carboxamide (XlVa). N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC.HCI, 3.86 g, 20.21 mmol), N-methylmorpholine (NMM, 1.83 mL, 13.47 mmol) and 1-Hydroxybenzotriazole (HOBT, 1.82 g, 13.47 mmol) were successively added to a stirred solution of the sodium salt of (2S, 5R)-6-benzyloxy-7-oxo-1,6-diazabic [3.2.1] octane-2-carboxylic (XIII) acid (4.02 g, 13.47 mmol) in dimethylformamide (DMF, 40 mL) at 0°C. Compound (XIII) was prepared using the procedure described in International Patent Application No. PCT / IB2013 / 059264. To this cooled solution, a solution of compound (Xlla) (3.1 g, 13.47 mmol) in dimethylformamide (15 mL) at 0°C was added, and stirring continued for 16 hours at room temperature. The reaction mixture was poured into cold water (1 L) while stirring. The separated solid was filtered and further purified by column chromatography using silica gel (60–120 mesh).Elution with a v / v mixture of ethyl acetate:hexane (1:3) and solvent evaporation of the combined fractions gave compound (XlVa) (5.06 g, 77%) as a white solid. Analysis: Mass: 487.3 (MH) for MW: 488.59; MF: C25H36N4O6; 1H-NMR: (400 MHz, CDCI3): δ 10.22 (bs, 1 H), 7.43-7.37 (m, 5 H), 5.06 (d, J = 12.0 Hz, 1 H), 4.90 (d, J = 12.0 Hz), 1 H), 4.14-3.73 (m, 4 H), 3.49 - 3.45 (m, 1 H), 3.30-2.27 (m, 1 H), 3.05 - 3.02 (m, 1 H), 2.89 - 2.83 (m, 2 H), 2.31 - 2.27 (m, 2 H), 2.05 - 1.99 (m, 2 H), 1.84- 1.80 (m, 2H), 1.67 - 1.64 (m, 1 H), 1.45 (s, 9 H), 1.04 (d, J = 8 Hz, 3 H). Step 8: Synthesis of (2S,5R)-6-hydroxy-N-{[(2S,4R)-4-methylpyrrolidine-1-tert-butylcarboxylate]methoxy}7-oxo-1,6-diazabicyl[3.2.1]octane-2-carboxamide (XVa). A solution of compound (XlVa) (5.06 g, 10.37 millimoles) in methanol (40 mL) containing 10% palladium on carbon (1.69 g) was hydrogenated at 50 psi at 25–30°C. The progress of the reaction was monitored by thin-layer chromatography (TLC) (ethyl acetate:hexane 1:1). After complete consumption of the starting material, the reaction mixture was filtered through a Celite bed, and the residue was washed with fresh methanol (2 x 20 mL). The combined filtrate was concentrated under reduced pressure to obtain compound (XVa) (3.55 g, 86%). This was used as such for the next reaction. Analysis: Mass: 397.3 (MH) for MW: 398.46; MF: Ci8H3oN406; Step 9: Synthesis of the tetrabutylammonium salt of (2S, 5R)-6-sulfooxy-N-{[(2S,4R)-4-methylpyrrolidine1-tert-butylcarboxylate]methoxy}-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (XVIa). Triethylamine (2.43 mL, 17.83 mmol) was added, followed by pyridine sulfur trioxide complex (2.13 g, 13.36 mmol), to a solution of (2S,5R)-6-hydroxy-N-{[(2S,4R)-4-methylpyrrolidine-1-tert-butylcarboxylate]methoxy}-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (XVa) (3.55 g, 8.91 mmol) in dichloromethane (35 mL) with stirring and an argon atmosphere at 25°C. Stirring was continued for 16 hours at 25°C. TLC indicates completion of the reaction. The resulting mixture was filtered under suction, and the residue was washed with dichloromethane (25 mL). The combined filtrate was concentrated under reduced pressure to obtain the product as an oil. A 0.5 M potassium hydrogen phosphate (KH2PO4) solution (150 mL) was added to the waste oil and stirred for 0.5 hours at 25°C. The solution was washed with ethyl acetate (2 x 40 mL). The aqueous reaction mixture was transferred to a flask and tetrabutylammonium hydrogen sulfate (3.62 g, 10.69 mmol) was added with stirring.The reaction mixture was stirred for 0.5 hours and extracted with dichloromethane (2 x 70 mL). The dichloromethane extract was dried over anhydrous sodium sulfate, and the volatiles were removed under reduced pressure to obtain the crude product. This was purified by column chromatography using 60120 mesh silica gel and a v / v elution mixture of dichloromethane:methanol (10:1). The pure fractions were collected, and the solvent was evaporated to obtain the tetrabutylammonium salt of (2S,5R)-6-sulfooxy-N{[(2S,4R)-4-methylpyrrolidine-1-tert-butylcarboxylate]methoxy}-7-oxo-1,6-diazabicyclo[3,2,1]octane-2-carboxamide (XVIa) (5.4 g, 83%). Analysis: Mass: 477.3 (MH) for MW: 719.99; MF: C34H65N5O9S; Ή-RMN: (400 MHz, CDCI3): δ 10.27 (s, 1 H), 4.35 (s, 1 H), 4.16 - 4.15 (m, 1 H), 4,01 3.93 (m, 2 H), 3.91 - 3.79 (m, 1 H), 3.76 - 3.74 (m, 1 H), 3.48 - 3.37 (m, 1 H), 3.32 3.28 (m, 8 H), 2.92 - 2.88 (m, 2 H), 2.33 - 2.31 (m, 2 H), 2.20 -2.16 (m, 1 H), 1.92 - 1.84 (m, 1 H), 1.68-1.65 (m, 12 H), 1.48- 1.42 (m, 16 H), 1.06-1.01 (m, 15 H) fiPQfrnn / zznz / e / YiAi Paso 10: Síntesis de (2S,5R)-N-{[(2S,4R)-4-met¡lpirrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2 .1]octano-2-carboxamida (la). Compound (XVIa) (5.4 g, 7.4 mmol) was dissolved in dichloromethane (32 mL) and the solution was cooled to -15°C. Trifluoroacetic acid (21.6 mL) was added dropwise to the solution at -10°C to 15°C. The reaction was monitored by ES-MS analysis. The solution temperature was maintained between -10 and -5°C for 1 hour. After the reaction was complete, hexane (250 mL) was added to the reaction mixture. The hexane layer was decanted, and the oily residue was thoroughly washed with hexane (150 mL) and diethyl ether (250 mL). The resulting solid residue was further washed with diethyl ether, acetonitrile, and dichloromethane (80 mL each). The residue was dried under reduced pressure to obtain the product as a white solid, which was recrystallized using a mixture of isopropanol and water (7:1) to obtain the compound of formula (la) as a white solid (2.05 g, yield: 73%). Analysis: Mass: 377.0 (MH) for MW: 378.41; MF: C13H22N4O7S; 1H-NMR: (500 MHz, DMSO-d6): δ 11.66 (s, 1 H), 8.87 (s wide, 2 H), 4.05 - 3.91 (m, 4 H), 3.83 (d, J = 5 Hz, 1 H), 3.38 - 3.36 (m, 1 H), 3.05 - 2.96 (m, 2 H), 2.75 (dd, J = 20 Hz, 10 Hz, 1 H), 2.38 - 2.34 (m, 1 H), 2.05 - 2.02 (m, 1 H), 1.92 - 1.82 (m, 2 H), 1.77 1.65 (m, 3 H), 1.03 (d, J = 5 Hz, 3 H). Melting point: 172 to 174 °C (decomposition) «ραΐτηη / ζζηζ / Β / γίΛΐ Example 2 (2S,5R)-N-{[(2S,4S)-4-Methyl-pyrrol¡din-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡cyclo[3.2.1]octane -2-carboxamide (Ib) The compound of Formula (Ib) was prepared according to the procedure described in Example 1, starting from 1-tert-butyl-2-methyl (2S, 4S)-4-methylpyrrolidine-1,2-dicarboxylate (compound (Xb)), with an overall yield of approximately 23%. Analysis: Mass: 377.0 (MH) for MW: 378.41; MF: C13H22N4O7S; 1H-NMR: (500MHz, DMSO-d6) Hz, 10 Hz, 1H), 3.07 - 3.02 (m, 1 H), 2.97-2.94 (m, 1 H), 2.72 (t, J = 15 Hz, 1 H), 2.43-2.31 (m, 1 H), 2.19-2.13 (m, 1 H), 2.06 - 2.01 (m, 1 H), 1.90 - 1.85 (m, 1 H), 1.75 - 1.63 (m, 3 H), 1.03 (d, J = 5 Hz, 3 H). Example 3 (2S,5R)-N-{[(2R,4S)-4-Methyl-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane -2-carboxamide (le) The compound of Formula (le) was prepared according to the procedure described in Example 1, starting from 1-tert-butyl-2-methyl (2R, 4S)-4-methylpyrrolidine-1, 2-dicarboxylate (compound (Xc)), with an overall yield of approximately 16.4%. Analysis: Mass: 377.0 (MH) for MW: 378.41; MF: C13H22N4O7S; 1H-NMR: (500MHz, DMSO-d6): δ 11.72 (s, 1H), 8.96 (bs, 1H), 8.70 (bs, 1H), 4.03 - 3.80 (m, 3H), 3.81 -3.80 (d, 1H), 3.43-3.37 (m, 2H), 3.05-2.98 (m, 2H), 2.75-2.73 (m, 1 H), 2.382.33 (m, 1 H), 2.08-2.07 (d, 2 H), 1.89-1.82 (m, 2H), 1.71-1.65 (m, 2H), 1.03-1.02 (d, 3H). EXAMPLE 4 The compound of Formula (Id) was prepared according to the procedure described in Example 1, starting with 1-tert-butyl-2-methyl (2R, 4R)-4-methylpyrrolidine-1, 2-dicarboxylate (compound (Xd)), with an overall yield of approximately 20%. / 3 3 Analysis: Mass: 377.0 (MH) for MW: 378.41; MF: C13H22N4O7S; 'H-NMR: (500MHz, DMSO-de): or 11.73 (s, 1 H), 8.88 (bs, 1H), 8.75 (bs, 1 H), 4.03-3.97 (m, 2H), 3.81 -3.80 (d, 2H), 3.35-3.34 (m, 1 H), 3.03-2.99 (m, 2H), 2.75-2.71 (m, 1 H), 2.302.29(m, 1 H), 2.19-2.17 (m, 1H),2.08(s, 1H), 2.04-2.02 (m, 1H), 1.90-1.89 (m, 1H), 1.711.70 (m, 2H), 1.23-1.21 (m, 1H), 1.04-1.03 (d, 3H). The compounds in Examples 5 to 10 (Table 1) were prepared following the procedures described in Example 1 and following Scheme 1 and / or Scheme 2. Tabla 1 Sr. Compuesto de Fórmula (1) Análisis o ω O OÍ ZT o ΐ 0 T Ή-RMN: (400MHz. DMSO-d,): δ 11 73 (s. 1 H). 8.89 (bs. 1 H) 8.71 (bs: 1 H). 4.86 (bs. 1 H): 4.03 3 93 (m. 3 H). 3 84-3.79 (m. 2 H), 3 43-3.28 (m. 4 H). 3.06 -2.96 (m. 3 H). 2.44 - 1.41 (m 1 H). 2 13-2 03 (m 2 H) 1.92-1.88 (m 1 H). 1.75- 1.68 (m 2 H) M.F: C-K.NxO.S M.W: 394.41: Masa 393 40 (M-H) 6 0 ω 0 a / ZT o o T Ή-RMN: (400MHz. DMSO-d,,): 511.75 (s. 1 H). 8.93 (bs. 1 H). 8.70 (bs. 1 H). 4.83 (bs. 1 H), 4.083 89 (m. 5 H). 3 44 - 3.32 (m. 3 H). 3 18 - 2.96 (m. 3 H). 2.50 -2.43 (m. 1 H). 2.05 - 1.64 (m. 6 H) M.F. C- 1H.2N4O-S: M.W. 394.40: Masa: 393.3 (M-H) 7 O ω O a / ZT o o T Ή-RMN: (500MHz. DMSO-d.,): 5 11.73 (s. 1H), 8 91 (bs. 1H). 8 70 (bs. 1H). 4 90-4 88 (t. 1H. J=5Hz). 4 03-4 00 (m. 2H). 3.94-3.90 (m. 1 H). 3.85-3.80 (m. 2H). 3.42-3.32 (m. 3H). 3.05-3.03 (m. 1H). 2 992 97 (m, 2H). 2.45-2.43 (m. 1H). 2.04-2.02 (m. 1H). 1 90-1 81 (m. 2H). 1.74-1.70 (m. 3H). M.F. C- íH^NxOiS. M.W. 394.40: Masa: 393.3 (M-H) 8 O \ “3 ( o / 12 <> © / o ω O X Ή- RMN: (500MHz. DMSO-d,.): 5 11 71 (s. 1H). 8 88 (bs. 1H). 8.69 (bs. 1H). 4.86 (s, 1H). 4.03-3.93 (m. 2H). 3.81-3.80 (m. 2H). 3 43-3 38 (m. 2H). 3.29-3.27 (m. 1H). 3.06-2.98 (m. 3H). 2.45-2 41 (m. 1H). 2 12-2 09 (m. 1H). 2.04-2.02 (m. 1H). 1.90-1.89 (m. 1 H). 1.73-1.68 (m. 2H). 1.36-1.30 (m. 2H) M.F. C- Η .Ν,Ο S M.W. 394.40: Masa: 393.3 (M-H) 0 * -p o / iz o / = ID / o X ’H- RMN (500MHz. DMSO-d,): δ 11 81 (bs. 1H). 9.03 (bs. 2H). 7.93 (bs. 2H), 4 03-3 98 (m. 3H. J=5Hz). 3 83-3 82 (m. 1H). 3 46-3 43 (m. 1 H), 3.03-2.92 (m. 5H). 2 51-2 50 (m. 1H) 2 27-2 23 (m. 1H) 2 08-2 03 (m. 2H). 1 88-1 86 (m. 1H). 1 72-1 70 (m. 2H). 1 42-1 36 (m. 2H) M.F: C^K .N^OS C-HF;O.. M.W: 507.44: Masa: 392.1 (M-H) 10 ó 8 a ¢)=^ ° / T o í Ή- RMN: (500MHz. DMSO-d,): 5 11 78 (s. 1H). 9 05-8.82 (bs. 2H). 4.51-4.40 (d sym. m. J =50Hz. HF unido 2H ). 4.03-4.02 (m. 2H). 4.01-4.00 (m. 1H). 3.88-3.87 (m. 1H). 3.83 (m. 1H). 3.45-3.44 (m. 1H). 3.04-2.99 (m. 2H). 2 75-2.71 (m. 1H).2 07-2 02 (m. 1H). 1.88-1.84 (]m. 3H). 1.72-1.70 (m. 2H) MF: C·H.FN,O,S MW: 396.40 Mass: 395.0 (MH). b?ai?nn / zzh / B / yΙΛι BIOLOGICAL ACTIVITY The biological activity of representative compounds according to the invention was investigated against various bacterial strains. In a typical study, overnight bacterial cultures were appropriately diluted and inoculated onto agar media containing two-fold dilutions of the test compounds. Observations of growth or non-growth were made after 16–20 hours of incubation at 35 ± 2°C in room air. The general procedure was performed in accordance with the recommendations of the Clinical and Laboratory Standards Institute (CLSI), Performance Standards for Antimicrobial Susceptibility Testing, 20th Informational Supplement, M07-A9, Volume 32, No. 2, 2012. Molten Mueller-Hinton Agar (MHA) (BD, USA) containing serial dilutions of each antibacterial agent was poured onto plates and allowed to solidify.Appropriate suspensions of the freshly grown cultures in normal saline were prepared, and approximately 10⁴ CFU / spot of the organism were administered onto agar plates containing the drug using a multi-point automated inoculator (Mast, UK). The plates were incubated in a biochemical oxygen demand (BOD) incubator at 37°C for 18 hours and then examined for growth. MICs were interpreted as the lowest drug concentration that completely inhibited bacterial growth. Table 2 represents the antibacterial activity profile of the compounds according to the present invention against several multidrug-resistant bacterial strains. The antibacterial activity of the compounds according to the invention was also investigated in combination with various antibacterial agents. For example, the antibacterial activity of the representative compounds of Formula (I) (Example 1 and Example 2) in combination with Ceftazidime and Cefixime is summarized in Table 3. As can be seen in Table 3, ceftazidime, cefixime, and the representative compounds of Formula (I) (Example 1 and Example 2), when used alone, did not exhibit significant antibacterial activity. However, surprisingly, the representative compounds of Formula (I) (Example 1 and Example 2) in combination with ceftazidime and cefixime exhibited unusual and unexpected synergistic antibacterial effects against highly resistant bacterial strains. RPQfrnn / zznz / e / YiAi Table 2. Antibacterial activity of representative compounds according to the invention (expressed as XHC (mcg mi)) Compounds KP ATCC 700603 E. cali 13351 E. cali 13352 E coli 13353 E cali M36 E. coli 7MP E. coli M49 E. coli M50 E coli M 138 E. coli S 1S K. pneumoniae H521 H522 H523 H525 Example 1 >3? 1 1 9.5 9.5 1 4 0.5 0.5 1 I 0.5 0 5 Example 1 >32 1 1 9.5 9.5 2 4 1 1 2 1 1 1 Example 3 >32 1 1 9.5 9.5 - 4 9.5 0.5 1 1 0.5 0.5 Example 4 >J- 1 - 1 9.5 - 4 1 1 - - - Λ Example 5 >32 1 2 1 1 - 4 1 1 1 1 1 1 Example 6 >32 1 - I 1 - 4 1 1 - - - 1 Example 7 >32 1 - 1 1 - 4 1 1 - - 1 1 Example 8 >32 - 4 1 1 4 4 1 1 - 4 s I 1 Example 9 >32 4 4 - - s 4 - 4 - 4 4 - - Example 10 1 - 1 1 4 1 1 • - - - - . βραι?ηη / ζζηζ / Β / γΐΛΐ Table 3 Antibacterial activity of ceftazidime and cefixime in the presence of representative compounds of the invention against several multidrug-resistant (MDR) gram-negative strains. Organism Strain Beta-lactamase MIC(mgL) Ceftazidime Cefixime Example 1 Example 2 Ceftazidime * Example 1 Ceftazidime — Example 2 Cefixime Example 1 Cefixime — Example 2 1 pneumoniae E77 lOKL ESBL >32 >32 >32 >32 0.5 2 1 - 1 K. pneumoniae B SS IΦλί ESEL >32 >32 >32 >32 0.5 1 - 1 3 pneumoniae NCTC 13443 MM ESBL >32 >32 >32 >32 4 4 4 - 4 pneumoniae S 465 OXA-1SL ESEL >32 >32 >32 >32 1 ·» 1 - 5 pneumoniae NCTC 1-435 \TM-1 >32 >32 >32 >32 0.5 1 1 1
Claims
1. A compound of Formula (I), or a pharmaceutically acceptable stereoisomer or salt thereof [Formula (I) wherein: B is selected from: (a) hydrogen, (b) halogen, (c) Ci-Ce alkyl, (d) ORi, (e) NRiR2, (f) SH, (g) SR1, (h) SOR1, (i) SO2Ri, (j) CHO, (k) COOR1, (l) CONRiR2, (m) CN, (n) heteroaryl, (o) heterocycloalkyl, or (p) NHC(=NH)NH2;R1 and R2 are each independently: (a) hydrogen, (b) Ci-Ce 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) Ci-Ce alkyl, or (c) a pharmaceutically accepted salt-forming cation selected independently from Na, K, or Ca.; 2. The composition according to indication 1, select: (2S,5R)-N-{[(2S,4R)-4-Metil-p¡rrol¡d¡n-2-¡l]methyloxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-Met¡lp¡rrol¡din-2-¡l]methyloxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-Methyl-pyrrolidin-2-yl]methylox¡}-7-oxo-6-(sulfooxi)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-Methyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-h¡droximethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; 2S,5R)-N-{[(2S,4S)-4-hidroximethylp¡rrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octano- 2-carboxamida; fiPQfrnn / zznz / e / YiAi (2S,5R)-N-{[(2R,4S)-4-h¡droximet¡lp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxi)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-h¡drox¡met¡lp¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-Am¡nomethyl-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane salt de trifluoroacetate de -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-Aminomethyl-pyrrolid¡n-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-Am¡nomet¡lp¡rrol¡d¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-Am¡nometil-p¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octano sal de trifluoroacetato de -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-c¡anomet¡lp¡rrolid¡n-2-¡l]metilox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octano -2-carboxamida; 2S,5R)-N-{[(2S,4S)-4-C¡anometilp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano- 2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-cianomet¡l-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-c¡anomet¡lpirrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-Fluorometíl-pirrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano -2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-Fluorometil-pirrolid¡n-24l]metiloxi}-7-oxo-6-(sulfooxi)-1,6diazabic¡clo[3.2.1]octano -2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-Fluoromet¡l-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano -2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-Fluorometil-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octano -2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-clorometil-pirrolidin-2-il]metiloxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1]octane -2-carboxamide; fiPQfrnn / zznz / e / YiAi (2S,5R)-N-{[(2S,4S)-4-chloromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo-carboxamide;12] (2S,5R)-N-{[(2R,4S)-4-chloromethyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-chloromet¡l-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6diazabic¡clo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-mercaptomethyl-pyrrolid¡n-2-yl]methylose}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-mercaptomet¡lp¡rrol¡d¡n-2-¡l]met¡loxy}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-mercaptomet¡l-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-mercaptomethyl-pyrrolidin-2-yl]methylose}-7-oxo-6-(sulfoxy)-1,6diazabicyclo[3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-(Azirid¡n-1 -ilmetil)-pirrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Azirid¡n-1 -ilmetil)-pirrolidin-2-¡l]metilox¡}-7-oxo-6-(sulfooxi)-1,6diazabiciclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Aziridin-1-ilmetil)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxi)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Aziridin¡d¡n-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]metilox¡}-7-oxo-6-(sulfooxi)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Azetidin-1-ilmetil)-pirrolidin-2-il]metilox}-7-oxo-6-(sulfooxi)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Azetidin-1-ilmetil)-pirrolidin-2-il]metilox}-7-oxo-6-(sulfooxi)-1,6diazabiciclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Azetidin-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Azetidin-1-ylmethyl)-pyrrolidin-2-yl]methylox¡}-7-oxo-6-(sulfooxi)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(pyrrolidin-1 -ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(p¡rrol¡d¡n-1-ylmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(pyrrolid¡n-1 -ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(p¡rrolid¡n-1-ylmetil)-pirrolidin-2-yl]metiloxi}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Pipendin-1-¡lmetil)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(P¡per¡d¡n-1-¡lmet¡l)-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Piper¡d¡n-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(P¡peridin-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Azepan-1 -ylmethyl)-pyrrol¡din-2-¡l]meth¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Azepan-1 -ylmethyl)-pyrrol¡d¡n-2-yl]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Azepan-1 -ylmethyl)-p¡rrolid¡n-2-¡l]methylox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Azepan-1 -ylmethyl)-p¡rrolid¡n-2-yl]met¡loxi}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Piperazin-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Piperazin-1 -ylmethy l)-pyrrolid¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Piperazin-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; fiPQfrnn / zznz / e / YiAi (2S,5R)-N-{[(2R,4R)-4-(Piperazin-1 -ylmethy l)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Morfolin-1 -ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Morfolin-1-¡lmet¡l)-p¡rrolidin-2-¡l]metilox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Morfolin-1 -ylmetil)-pirrolidin-2-yl]metiloxi}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Morfol¡n-1-ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(Thiomorfolin-1 -ylmethyl)-pyrrol-dn-2-yl]methyloxo}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(Thiomorfolin-1-ylmethyl)-pyrrol-dn-2-yl]methyloxo}-7-oxo-6-(sulfooxy)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(Thiomorpholin-1 -ylmethyl)-pyrrolid-n-2-l]methyloxo}-7-oxo-6-(sulfooxo)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2R,4R)-4-(Thiomorpholin-1 -ylmethyl)-pyrrolid-n-2-l]methyloxo}-7-oxo-6-(sulfooxo)-1,6diazabicyclo [3.2.1]octano-2-carboxamida; (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrrol-1 -ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabicyclo[3.2.1]octane-2-carboxam¡da; (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrrol-1 -ylmethyl)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡clo[3.2.1]octane-2-carboxam¡da; (2S,5R)-N-{[(2R,4S)-4-(1 H-pyrrol-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabic¡clo[3.2.1]octane-2-carboxam¡da; (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrrol-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabic¡clo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2S,4R)-4-(1 H-imidazol-1 -ilmet¡l)-p¡rroldin-2-¡l]meth¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1-octano-carboxylate¡]; (2S,5R)-N-{[(2S,4S)-4-(1 H-imidazol-1-¡lmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]octano-2-carboxamide; βροι?ηη / ζζηζ / Β / γΐΛΐ (2S,5R)-N-{[(2R,4S)-4-(1 H-imidazole-1 -¡meth¡l)-p¡rrol¡d¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1]octane-2-carboxam¡da; (2S,5R)-N-{[(2R,4R)-4-(1 H-imidazol-1 -ylmet¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 d¡azabicyclo[3.2.1-octa-carboxylate); (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrazol-1 -ilmet¡l)-pyrrol¡d¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1]octano-carboxam¡¡¡¡¡; (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrazol-1-ylmet¡l)-p¡rrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-(1 H-pyrazol-1-ilmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1-octa-carboxylate¡¡]; (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrazol-1 -ilmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6 diazabic¡chlo[3.2.1-octa-carboxylate¡¡]; (2S,5R)-N-{[(2S,4R)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pi rrolidin-2-yl] methi loxi}-7-oxo-6-( diazabicyclo[3.2.1]octano-2-carboxamide; (2S,5R)-N-(2S,4-(2-S-1) H-1,2,3-triazol-1 -ylmethyl)-pi rrolidin-2-yl] methyl loxi}-7-oxo-6-( diazabic¡clo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2R,4S)-4-(1 H-1,2,3,3-p-ylmethyl) rrolidin-2-yl] methi loxi}-7-oxo-6-( diazabic¡clo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2R,4R)-4-(1 H-1,2,3-triazol-l -ylmethyl)-pyrrolide¡n-2-¡l]methylox¡}-7-oxo-6-( diazabicyclo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2S,4R)-4-(1 H-1,2,4-triazole-1 -ylmethyl methyl) loxi}-7-oxo-6-( diazabic¡clo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,4-triazol-1 -ylmethyl)-pyrrol¡din-2-yl]meth¡loxy}-7-oxo-6-( diazabic¡clo[3.2.1]octane-2-carboxam¡da; (2S,5R)-N-{[(2R,4S)-4-(1 H-1,2,4-triazol-1 -ylmethyl)-pirrolidin-2-yl] methyl loxi}-7-oxo-6-( diazabic¡clo[3.2.1]octano-2-carboxam¡da; (2S,5R)-N-{[(2R,4R)-4-(1 H-1,2,4,triazol-1 -ylmethyl)-pirrolidin-2-yl] methyl loxi}-7-oxo-6-( diazabic¡clo[3.2.1]octano-2-carboxam¡da; on Ifooxi)-1,6sulfoox¡)-1,6sulfoox¡)-1,6sulfoox¡)-1,6sulfoox¡)-1,6sulfooxi)-1,6sulfoox¡)-1,6sulfoox¡)-1,6(2S,5R)-N-{[(2S,4R)-4-(1 H-tetrazol-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2S,4S)-4-(1 H-tetrazol-1 -ylmet¡l)-p¡rrol¡d¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6 diazab¡c¡clo[3.2.1]octane-2-carboxamida; (2S,5R)-N-{[(2R,4S)-4-(1 H-tetrazol-1 -yl methyl)-pyrolide η-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]octano-2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-(1 H-tetrazol-1 -ylmet¡l)-p¡rrol¡d¡n-2-yl]met¡lox¡}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]caroboxamide;2-carboxamide-2 (2S,5R)-N-{[(2S,4R)-4-(2H-tetrazoly-2-ylmethyl)-pyrrolidin-2-yl]methylose}-7-oxo-6-(sulfoxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[[(2S,4S)-4-(2H-tetrazol-2-ylmethyl)-p¡rrol¡din-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-ylmethyl)-pyrrolidin-2-¡l]methyloxy}-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]methylose}-7-oxo-6-(sulfoxy)-1,6 diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2S,4S)-4-Carbamim¡domet¡lp¡rrolid¡n-2-¡l]met¡loxy}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane -2-carboxamide; (2S,5R)-N-{[(2S,4R)-4-Carbam¡midomet¡l-pyrrolid¡n-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-Carbamimidomethylpyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4R)-4-Carbamimidomethylpyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.2.1]octane-2-carboxamide; or a stereoisomer or a pharmaceutically acceptable salt thereof.
3. The composition follows the indication 1, selected from: Sal sódica de (2S,5R)-N-{[(2S,4R)-4-Methyl-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.
2. 1 ]octane-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Methyl-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.
2. 1 ]octane-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2R,4S)-4-Methyl-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.
2. 1 ]octano-2-carboxamida; βραι?ηη / ζζηζ / Β / γΐΛΐ Sal sódica de (2S,5R)-N-{[(2R,4R)-4-Methyl-p¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.
2. 1 ]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-H¡droximet¡lp¡rrol¡d¡n-24l]met¡loxi}-7-oxo-6-(sulfooxi)-1,6diazabic¡clo[3.
2. 1 ]octane-2-carboxamida; Sodium salt of 2S,5R)-N-{[(2S,4S)-4-H¡droximethylp¡rrol¡d¡n-24l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.2.1 ]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-hidrox¡methylpyrrolidin-24l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabiciclo[3.2.1 ]octane-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-H¡drox¡methyl-pyrrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.
2. 1 ]octane-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Aminomet¡lp¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfooxy)-1,6diazabic¡clo[3.
2. 1]octane-2-carboxamid trifluoroacetate salt; Sal sódica de (2S,5R)-N-{[(2S,4S)-4-Aminomet¡lp¡rrol¡d¡n-24l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.
2. sal de trifluoroacetato de 1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2R,4S)-4-Aminomet¡lp¡rrol¡d¡n-24l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.
2. sal de trifluoroacetato de 1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2R,4R)-4-Aminometil-p¡rrol¡d¡n-24l]met¡lox¡}-7-oxo-6-(sulfoox¡)-1,6diazabic¡clo[3.
2. sal de trifluoroacetato de 1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-C¡anometil-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)-1,6diazabiciclo[3.2.1 ]octane-2-carboxamide; Sodium salt of 2S,5R)-N-{[(2S,4S)-4-Cyanomethyl-pyrrolidine-24l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyl[3.2.1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Cyanomethyl-pyrrolidine-24l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyl[3.
2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Cyanomethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Fluoromethyl-pyrrolidine-241]methyloxy}-7-oxo-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; fiPQfrnn / zznz / e / YiAi Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Fluoromethyl-pyrrolidine-24l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.
2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Fluoromethyl-pyrrolidine-2-l]methyloxy}-7-oxo-6-(sulfooxy)-1,6diazabicyclo[3.
2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Fluoromethyl-pyrrolidin-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2.1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Chloromethylpyrrolidine-2-yl]methyloxy}-7-oxo-6-(sulfoxy)-1,6diazabicyclo[3.
2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Chloromethylpyrrolidine-2-yl]methyloxy}-7-oxo-6-(sulfoxy)-1,6diazabicyclo[3.
2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Chloromethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfoxy)-1,6-diazabicyl[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-Chloromethyl-pyrrolidine-2-1]methyloxy}-7-oxo-6-(sulfoxy)-1,6-diazabicyl[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-mercaptomethyl-pyrrolidine-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-mercaptomethyl-pyrrolidine-2-yl]methyloxy}-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; (2S,5R)-N-{[(2R,4S)-4-mercaptomethyl-pyrrolidin-2-¡l]methyloxy¡}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.2] sodium salt.1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-mercaptomethyl-p¡rrol¡n-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)-1,6diazabicyclo[3.
2. 1 ]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Azirid¡n-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methyloxy}-7-oxo-6-(sulfoox¡)1, 6-diazabic chlo[3.2.1-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Aziridin-14lmethyl)-pyrrolidine-24l]methyloxy}-7-oxo-6-(sulfooxy)1, 6-diazabicyclo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azirid¡n-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(sulfooxy)1, 6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Aziridin-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)1, 6-d¡azabicyclo[3.2.1-octa-carboxylate]; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Azetidin-1 -ylmethyl)-pyrrolidine-2-¡l]methyloxy}-7-oxo-6-(sulfooxy)1, 6-diazabicyclo[3.2.1]octane-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Azetid¡n-1-¡lmethyl)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.2.1-¡¡¡¡¡¡¡¡²⁸⁴¡¡¡]; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azet¡d¡n-1-ilmet¡l)-p¡riOl¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.2-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Azetid¡n-1-ilmet¡l)-p¡rrol¡n-2-l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2-octa-card.21]; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(pyrrolidin-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)-l, 6-diazabicyclo[3.2.1]octano-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(p¡rrolidin-1-lmeth¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[2S,4S)-4-(p¡rrolidin-1-¡lmeth¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡²-¡¡¸⁄²⁄²⁄²⁄²⁄₄ₐℂ™™™ ²-oxo-oxo-2-oxo-2-oxo-2; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(p¡rroldin-1-lmethl)-p¡rrol¡n-2-¡l]methlox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(p¡rroldin-1-ilmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxy)-l, 6-diazabicic chloro. Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Piperid¡n-1-¡lmeth¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2.1-octa-carboxylate]; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(P¡peridin-1-¡lmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1-2-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(P¡pend¡n-1-ilmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1-2-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Piper¡din-1-¡lmet¡l)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2.2.1-octacartano-box]; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Azepan-1-ylmethyl)-pyrrolidine-2-yl]methyloxy}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Azepan-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6-(suIphooxy)1, 6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Azepan-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6-(sulfoox¡)1, 6-d¡azabicyclo[3.2.1-octacarta-box]; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Azepan-1 -ylmethyl)-pyrrolidine-2-¡l]methyloxy}-7-oxo-6-(sulfooxy)1, 6-diazabicyclo[3.2.1]octano-2-carboxamide; fiPQfrnn / zznz / e / YiAi Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(P¡peraz¡n-1-¡lmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo. Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(P¡peraz¡n-1-¡lmet¡l)-p¡rrol¡n-2-yl]meth¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¡¸⁺-¡¡¡º™™™™ box; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(P¡perazine-1-¡lmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Piperazin-1-ylmetil)-pirrolidin-2-yl]metiloxi}-7-oxo-6(sulfooxi)-1, 6-diazabiciclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(Morfolin-1 -ylmetil)-p¡rrol¡din-2-yl]metiloxi}-7-oxo-6-(sulfoox¡)- 1, 6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Morfolin-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Morfolin-1-ylmetil)-pyrrOlidin-2-yl]metiloxi}-7-oxo-6(sulfooxi)-l, 6-diazabicyclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(Morfolin-1 -ilmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6-(sulfoox¡)- 1, 6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(T¡omorphol¡n-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(Thoomorphol-1-methl)-prrol¡n-2-l]methl ox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(T¡omorphol¡n-1-ilmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2R,4S)-4-(T¡omorphol¡n-1-ilmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabicyclo[3.2R,4S)-4-(3.2-octa-carboxylate-2; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(Thiomorpholin-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrrole-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrrol-1-ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic chlo[3.2.1-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1 H-pyrrole-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabicyclo[3.2.1]octane-2-carboxamide; RPQfrnn / zznz / e / YiAi Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrrole-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-imidazol-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic chlo[3.2.2.1-octa-carta-box; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-imidazol-1-ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabicyclo[3.2.1-octa-carboxylate]; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1 H-imidazol-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabicyclo[3.2.1]octano-2-carboxamide; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-imidazol-1 -ylmethyl)-p¡rroldin-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic¡chlo[3.2.1]-octano-carboxylate; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-pyrazol-1-ylmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-pyrazol-1-ylmethyl)-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-(1 H-pyrazol-1 -ylmet¡l)-p¡rrol¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxy)- 1,6-diazabicyclo[3.2.1-2-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-pyrazol-1 -ilmet¡l)-p¡rrol¡n-2-¡l]methloxy}-7-oxo-6(sulfooxy)- 1,6-diazabic chlo[3.2.1-2-octa-carboxylate; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1H-1,2,3-triazol-1-¡lmethyl)-p¡rrol¡n-2-¡l]meth¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,3-triazol-1-lmethl)-pyrrol¡n-2-l]methlox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡chlo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-1,2,3-triazol-1 -ylmethyl)-pyrrolidiη-2-yl]methyloxy}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sal sódica de (2S,5R)-N-{[(2S,4R)-4-(1H-1,2,4-tr¡azol-1-ilmetil)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; βραι?ηη / ζζηζ / Β / γΐΛΐ Salt sodium de (2S,5R)-N-{[(2S,4S)-4-(1 H-1,2,4-triazol-1-ylmet¡l)-p¡rrolidin-2-yl]methyloxi}-7-oxo- 6(sulfooxy)-l ,6-diazabicyclo[3.2.1]octane-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1H-1,2,4-tr¡azol-1-ilmet¡l)-p¡rrolid¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxamida; Salt sodium de (2S,5R)-N-{[(2R,4R)-4-(1H-1,2,4,tr¡azol-1-¡lmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo- 6(sulfoox¡)-1,6-diazabic¡clo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(1 H-tetrazol-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6(sulfooxy)- 1,6-diazabiciclo[3.2.1]octane-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(1 H-tetrazol-1-ylmethyl)-pyrrolidin-2-yl]methyloxy}-7-oxo-6(sulfooxy)- 1,6-diazabiciclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(1 H-tetrazol-1-ylmethyl)-pyrroldin-2-¡l]met¡loxi}-7-oxo-6(sulfooxy)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(1 H-tetrazol-1-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6(sulfooxi)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-(2H-tetrazoly-2-ylmetil)-pirrol¡din-2-yl]metiloxi}-7-oxo-6(sulfooxi)- 1,6-diazabiciclo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-(2H-tetrazol-2-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxi)- 1,6-diazabiciclo[3.2.1]octano-2-carboxam¡da; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-(2H-tetrazol-2-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxy)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4R)-4-(2H-tetrazol-2-ylmet¡l)-p¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfooxy)- 1,6-diazabic¡clo[3.2.1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4S)-4-Carbam¡m¡dometil-p¡rrol¡d¡n-2-¡l]met¡loxy}-7-oxo-6-(sulfoox¡)1,6-diazabic¡clo[3.
2. 1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2S,4R)-4-Carbam¡midometil-pirrolidin-2-yl]metiloxi}-7-oxo-6-(sulfooxi)1,6-diazabic¡clo[3.
2. 1]octano-2-carboxamida; Sodium salt of (2S,5R)-N-{[(2R,4S)-4-Carbam¡midomet¡lp¡rrol¡d¡n-2-¡l]met¡loxi}-7-oxo-6-(sulfoox¡)1,6-diazabic¡clo[3.
2. 1]octano-2-carboxamida; Salt sódica de (2S,5R)-N-{[(2R,4R)-4-Carbamim¡domet¡lp¡rrol¡d¡n-2-¡l]met¡lox¡}-7-oxo-6(sulfoox¡)-1,6-diazabic¡clo[3.
2. 1]octano-2-carboxamida; o un estereisomero.
4. The composition follows the indication 1, selected by fiPQfrnn / zznz / e / YiAi β?αι?ηη / ζζηζ / Β / γΐΛΐ β?αι?ηη / ζζηζ / Β / γΐΛΐ β?αι?ηη / ζζηζ / Β / γΐΛΐ fiPQfrnn / zznz / e / YiAi 5. A pharmaceutical composition comprising a compound according to any one of claims 1 to 4.
6. The pharmaceutical composition according to claim 5 further comprises 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, cefamycin, cefem, lincosamide, lipopeptide, macrolide, ketolide, monobactam, nitrofuran, antibacterial agents oxazephem, oxapenam, oxazolidinone, penam, penem, penicillin, polypeptide, quinolone, sulfonamide or tetracycline.
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, cephalexin, cephaloglycine, cephalonium, cephaloridine, cephalothin, cefamandole, cefapirin, cefatrizine, cefazaflur, cefazedone, cefazolin, cefbuperazone, cefcapen, cefclidine, cefdaloxime, cefdinir, cefditoren, cefepime, cefetamet, cefixime, cefluprenam, cefmenoxime, cefmetazole, cefminox, cefodizime, cefonicid, cefoperazone, ceforanide, cefoselis, cefotaxime, cefotetan, cefotiam, cefovecin, cefoxitin, cefozopran, cefpimizole, cefpiramide, cefpirome, cefpodoxime, cefprozil, cefquinome, cefradine, cefroxadine, cefsulodine, ceftaroline, ceftazidime, cefteram, ceftezole, ceftibuten, ceftiofur, ceftiolene, ceftizoxime, ceftobiprole, ceftolozane, ceftriaxone, cefuroxime, cephalodin, cefuidin cefiderocol, flomoxef, latamoxef, loracarbef, moxalactam,or a pharmaceutically acceptable derivative there of., 10. The pharmaceutical composition according to claim 6, wherein the antibacterial agent is at least one selected from a group consisting of cefaclor, cefadroxil, cephalexin, cefdinir, cefixime, cefpirome, cefpodoxime, cefprozil, cephradine, 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. fiPQfrnn / zznz / e / YiAi 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 of claims 1 to 4, in the treatment or prevention of bacterial infections.
14. Use of a pharmaceutical composition according to any of claims 5 to 12, in the treatment or prevention of bacterial infections.
15. A method for treating or preventing a bacterial infection in a subject, said method comprising administering to said subject a compound according to any one of claims 1 to 4.
16. A method for treating or preventing a bacterial infection in a subject, said method comprising administering to said subject a pharmaceutical composition according to any one of claims 5 to 12.