# US 2014/0194385 A1 · Boronic acid derivatives and therapeutic uses thereof

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- Number: US 2014/0194385 A1
- Document ID: US20140194385A1
- Status: Published application
- Kind: A1
- Application number: 14/146,671
- Filed: 2014-01-02
- Published: 2014-07-10
- Earliest claimed: 2013-01-04
- Assignees: Rempex Pharmaceuticals, Inc.
- Applicants: Rempex Pharmaceuticals, Inc.
- Inventors: Raja K. Reddy; Tomasz Glinka; Maxim Totrov; Scott Hecker
- Web page: https://patentgrep.com/patent/US20140194385A1

## CPC

- A61K 31/69: Boron compounds
- A61K 31/407: condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
- A61K 31/4196: 1,2,4-Triazoles
- A61K 31/427: not condensed and containing further heterocyclic rings
- A61K 31/546: containing further heterocyclic rings, e.g. cephalothin
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 31/04: Antibacterial agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07F 5/025: {Boronic and borinic acid compounds}
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use as therapeutic agents. Other embodiments relate to pharmaceutical compositions containing boronic acid derivatives and additional excipient such as meglumine.

## Claims

### Claim 1

A compound having the structure of Formula (I) or Formula (I.1):
or pharmaceutically acceptable salts thereof, wherein:
G is selected from the group consisting of —H, —NR1R2, —CH2N3, —C(O)NR1R2, —CH2C(O)NR1R2, —CH2S(O)2NR1R2, —CH2—Y—Z, —CH2—Y—X, and —SR3;
Y is selected from a group consisting of —S—, —S(O)—, —S(O)2—, —O—, and —NR1—;
R is selected from a group consisting of —H, —C1-9alkyl, —CR1R2OC(O)C1-9alkyl, —CR1R2OC(O)OC1-9alkyl, and
R1 and R2 are each independently selected from the group consisting of —H and —C1-4alkyl;
R3 is —C1-4alkyl;
R4 is present 1 to 3 times and each R4 is independently selected from the group consisting of —H, —C1-4alkyl, —OH, —O—C1-4alkyl, —S—C1-4alkyl, halogen, and —CF3,
Z is selected from the group consisting of aryl optionally substituted with C1-4alkyl, amino, hydroxy, or halogen; heteroaryl optionally substituted with C1-4alkyl, amino, hydroxy, or halogen; and heterocycle optionally substituted with C1-4alkyl, amino, hydroxy, or halogen;
X is selected from the group consisting of —C1-4alkyl, —CH2R5, —CH(R5)2, and —C(R5)3; and
R5 is selected from the group consisting of a halogen, cyano, and azido.

### Claim 2 (depends on 1)

The compound of claim 1 having the structure of Formula (I):
or pharmaceutically acceptable salts thereof

### Claim 3 (depends on 1, 2)

The compound of claim 1 or 2, wherein:
each R4 is independently selected from the group consisting of —H, —C1-4alkyl, —OH, —O—C1-4alkyl, and halogen; and
Z is selected from the group consisting of aryl optionally substituted with C1-4alkyl, amino, hydroxy, or halogen and heteroaryl optionally substituted with C1-4alkyl, amino, hydroxy, or halogen.

### Claim 4 (depends on 1, 2)

The compound of claim 1 or 2, having the structure of Formula (Ia) or Formula (Ia.1):
or pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1, 2, 3, 4)

The compound of any one of claims 1-4, wherein R is H.

### Claim 6 (depends on 1, 2, 3, 4)

The compound of any one of claims 1-4, wherein R is —CR1R2OC(O)C1-9alkyl or —CR1R2OC(O)OC1-9alkyl.

### Claim 7 (depends on 6)

The compound of claim 6, where R is —CR1R2OC(O)C1-5alkyl or —CR1R2OC(O)OC1-5alkyl.

### Claim 8 (depends on 6, 7)

The compound claim 6 or 7, wherein R1 in R is H and R2 in R is H or —CH3.

### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7, 8)

The compound of any one of claims 1-8, wherein R4 is selected from H, F, Cl, —CH3, —CF3, —OCH3, and —SCH3.

### Claim 10 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of any one of claims 1-9, wherein G is H.

### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of any one of claims 1-9, wherein G is —NH2.

### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of any one of claims 1-9, wherein G is —C(O)NR1R2 and R1 and R2 in G are each independently selected from —H and C1-4alkyl.

### Claim 13 (depends on 12)

The compound of claim 12, wherein R1 in G is —CH3 and R2 in G is —CH3.

### Claim 14 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of any one of claims 1-9, wherein G is —CH2C(O)NR1R2 and R1 and R2 in G are each independently selected from —H and C1-4alkyl.

### Claim 15 (depends on 14)

The compound of claim 14, wherein R1 in G is —CH3 and R2 in G is H or —CH3.

### Claim 16 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of claims 1-9, wherein:
G is —CH2—Y—Z;
Y is —S—; and
Z is selected from the group consisting of imidazole, N-methylimidazole, aminoimidazole, triazole, N-methyltriazole, aminotriazole, tetrazole, N-methyltetrazole, aminotetrazole, thiazole, aminothiazole, thiadiazole, aminothiadiazole, oxazole, oxadiazole, pyridine, pyridazine, pyrimidine, pyrazine, azitidine and piperdine.

### Claim 17 (depends on 16)

The compound of claim 16, wherein Z is N-methyltetrazole.

### Claim 18 (depends on 16)

The compound of claim 16, wherein Z is thiadiazole.

### Claim 19 (depends on 16)

The compound of claim 16, wherein Z is aminothiadiazole.

### Claim 20 (depends on 16)

The compound of claim 16, wherein Z is azitidine.

### Claim 21 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of claims 1-9, wherein G is —CH2—Y—X and Y is —S—.

### Claim 22 (depends on 21)

The compound of claim 21, wherein X is —CH3.

### Claim 23 (depends on 21)

The compound of claim 21, wherein X is —CH2CN.

### Claim 24 (depends on 21)

The compound of claim 21, wherein X is —CH2N3.

### Claim 25 (depends on 21)

The compound of claim 21, wherein X is —CH2F.

### Claim 26 (depends on 21)

The compound of claim 21, wherein X is —CHF2.

### Claim 27 (depends on 21)

The compound of claim 21, wherein X is —CF3.

### Claim 28 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of claims 1-9, wherein G is —SCH3.

### Claim 29 (depends on 1)

The compound of claim 1, having the structure selected from the group consisting of:
pharmaceutically acceptable salts thereof.

### Claim 30 (depends on 1)

The compound of claim 1, having the structure selected from the group consisting of
or pharmaceutically acceptable salts thereof.

### Claim 31 (depends on 1)

The compound of claim 1, having the structure selected from the group consisting of
or pharmaceutically acceptable salts thereof.

### Claim 32

A compound having the structure of formula II or Formula II.1:
or pharmaceutically acceptable salts thereof, wherein:
G is selected from the group consisting of

### Claim 33 (depends on 32)

The compound of claim 32 having the structure of Formula (II)
or pharmaceutically acceptable salts thereof, wherein:

### Claim 34 (depends on 32, 33)

The compound of claim 32 or 33, wherein G is selected from the group consisting

### Claim 35 (depends on 32)

The compound of claim 32, having the structure of Formula Ha to Formula IIa.1:
or pharmaceutically acceptable salts thereof.

### Claim 36 (depends on 32, 33, 34, 35)

The compound of any one of claims 32 to 35, having the structure selected from the group consisting of:
or pharmaceutically acceptable salts thereof.

### Claim 37 (depends on 32, 33, 34, 35)

The compound of any one of claims 32 to 35, having the structure selected from the group consisting of:
or pharmaceutically acceptable salts thereof.

### Claim 38 (depends on 32, 33, 34, 35)

The compound of any one of claims 32 to 35, having the structure of
or pharmaceutically acceptable salts thereof.

### Claim 39 (depends on 32, 33, 34, 35)

The compound of any one of claims 32 to 35, wherein G is selected from the group consisting of

### Claim 40 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39)

A pharmaceutical composition comprising a therapeutically effective amount of a compound of any one of claims 1-39 and a pharmaceutically acceptable excipient.

### Claim 41 (depends on 40)

The pharmaceutical composition of claim 40, wherein the pharmaceutically acceptable excipient is a monosaccharide or monosaccharide derivative.

### Claim 42 (depends on 41)

The pharmaceutical composition of claim 41, wherein the monosaccharide or monosaccharide derivative is meglumine.

### Claim 43 (depends on 40, 41, 42)

The pharmaceutical composition of any one of claims 40 to 42, further comprising an additional medicament.

### Claim 44 (depends on 43)

The composition of claim 43, wherein the additional medicament is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent.

### Claim 45 (depends on 44)

The composition of claim 44, wherein the additional medicament is a β-lactam antibacterial agent.

### Claim 46 (depends on 45)

The composition of claim 45, wherein the β-lactam antibacterial agent is selected from Amoxicillin, Ampicillin (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin), Epicillin, Carbenicillin (Carindacillin), Ticarcillin, Temocillin, Azlocillin, Piperacillin, Mezlocillin, Mecillinam (Pivmecillinam), Sulbenicillin, Benzylpenicillin (G), Clometocillin, Benzathine, benzylpenicillin, Procaine benzylpenicillin, Azidocillin, Penamecillin, Phenoxymethylpenicillin, (V), Propicillin, Benzathine phenoxymethylpenicillin, Pheneticillin, Cloxacillin (Dicloxacillin, Flucloxacillin), Oxacillin, Meticillin, Nafcillin, Faropenem, Tomopenem, Razupenem, Cefazolin, Cefacetrile, Cefadroxil, Cefalexin, Cefaloglycin, Cefalonium, Cefaloridine, Cefalotin, Cefapirin, Cefatrizine, Cefazedone, Cefazaflur, Cefradine, Cefroxadine, Ceftezole, Cefaclor, Cefamandole, Cefminox, Cefonicid, Ceforanide, Cefotiam, Cefprozil, Cefbuperazone, Cefuroxime, Cefuzonam, Cefoxitin, Cefotetan, Cefmetazole, Loracarbef, Cefixime, Ceftriaxone, Cefcapene, Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefmenoxime, Cefodizime, Cefoperazone, Cefotaxime, Cefpimizole, Cefpiramide, Cefpodoxime, Cefsulodin, Cefteram, Ceftibuten, Ceftiolene, Ceftizoxime, Flomoxef, Latamoxef, Cefepime, Cefozopran, Cefpirome, Cefquinome, Ceftobiprole, Ceftaroline, CXA-101, RWJ-54428, MC-04,546, ME1036, Ceftiofur, Cefquinome, Cefovecin, RWJ-442831, RWJ-333441, or RWJ-333442.

### Claim 47 (depends on 45)

The composition of claim 45, wherein the β-lactam antibacterial agent is selected from Ceftazidime, Biapenem, Doripenem, Ertapenem, Imipenem, Meropenem, or Panipenem.

### Claim 48 (depends on 45)

The composition of claim 45, wherein the β-lactam antibacterial agent is selected from Aztreonam, Tigemonam, BAL30072, SYN 2416, or Carumonam.

### Claim 49 (depends on 45)

The composition of claim 45, wherein the β-lactam antibacterial agent is a penicillin, cephalosporin, carbapenem, monobactam, bridged monobactam, or combination thereof.

### Claim 50 (depends on 49)

The composition of claim 49, wherein the penicillin is benzathine penicillin, benzylpenicillin, phenoxymethylpenicillin, procaine, penicillin, oxacillin, methicillin, dicloxacillin, flucloxacillin, temocillin, amoxicillin, ampicillin, co-amoxiclav, azlocillin, carbenicillin, ticarcillin, mezlocillin, piperacillin, apalcillin, hetacillin, bacampicillin, sulbenicillin, mecicilam, pevmecillinam, ciclacillin, talapicillin, aspoxicillin, cloxacillin, nafcillin, pivampicillin, or a combination thereof.

### Claim 51 (depends on 49)

The composition of claim 49, wherein the cephalosporin is cephalothin, cephaloridin, cefaclor, cefadroxil, cefamandole, cefazolin, cephalexin, cephradine, ceftizoxime, cefoxitin, cephacetril, cefotiam, cefotaxime, cefsulodin, cefoperazone, ceftizoxime, cefinenoxime, cefinetazole, cephaloglycin, cefonicid, cefodizime, cefpirome, ceftazidime, ceftriaxone, cefpiramide, cefbuperazone, cefozopran, cefepim, cefoselis, cefluprenam, cefuzonam, cefpimizole, cefclidin, cefixime, ceftibuten, cefdinir, cefpodoxime axetil, cefpodoxime proxetil, cefteram pivoxil, cefetamet pivoxil, cefcapene pivoxil, cefditoren pivoxil, cefuroxime, cefuroxime axetil, loracarbacef, latamoxef, or a combination thereof.

### Claim 52 (depends on 49)

The composition of claim 49, wherein the cephalosporin is an anti-MRSA cephalosporin.

### Claim 53 (depends on 49)

The composition of claim 49, wherein the anti-MRSA cephalosporin is cefiobiprole, cefiaroline, or a combination thereof.

### Claim 54 (depends on 49)

The composition of claim 49, wherein the carbapenem is imipenem, meropenem, ertapenem, faropenem, doripenem, biapenem, panipenem, or a combination thereof.

### Claim 55 (depends on 49)

The composition of claim 49, wherein the carbapenem is an anti-MRSA carbapenem.

### Claim 56 (depends on 49)

The composition of claim 49, wherein the anti-MRSA carbapenem is PZ601 or ME1036.

### Claim 57 (depends on 49)

The composition of claim 49, wherein the monobactam is aztreonam, carumonam, BAL30072, or a combination thereof.

### Claim 58 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39)

A method of treating or preventing a bacterial infection, comprising administering to a subject in need thereof, a compound according to any one of claims 1-39.

### Claim 59 (depends on 58)

The method of claim 58, further comprising administering to the subject an additional medicament.

### Claim 60 (depends on 58, 59)

The method of claim 58 or 59, wherein the additional medicament is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent.

### Claim 61 (depends on 60)

The method of claim 60, wherein the additional medicament is a β-lactam antibacterial agent.

### Claim 62 (depends on 61)

The method of claim 61, wherein the β-lactam antibacterial agent is selected from Amoxicillin, Ampicillin (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin), Epicillin, Carbenicillin (Carindacillin), Ticarcillin, Temocillin, Azlocillin, Piperacillin, Mezlocillin, Mecillinam (Pivmecillinam), Sulbenicillin, Benzylpenicillin (G), Clometocillin, Benzathine, benzylpenicillin, Procaine benzylpenicillin, Azidocillin, Penamecillin, Phenoxymethylpenicillin, (V), Propicillin, Benzathine phenoxymethylpenicillin, Pheneticillin, Cloxacillin (Dicloxacillin, Flucloxacillin), Oxacillin, Meticillin, Nafcillin, Faropenem, Tomopenem, Razupenem, Cefazolin, Cefacetrile, Cefadroxil, Cefalexin, Cefaloglycin, Cefalonium, Cefaloridine, Cefalotin, Cefapirin, Cefatrizine, Cefazedone, Cefazaflur, Cefradine, Cefroxadine, Ceftezole, Cefaclor, Cefamandole, Cefminox, Cefonicid, Ceforanide, Cefotiam, Cefprozil, Cefbuperazone, Cefuroxime, Cefuzonam, Cefoxitin, Cefotetan, Cefmetazole, Loracarbef, Cefixime, Ceftriaxone, Cefcapene, Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefmenoxime, Cefodizime, Cefoperazone, Cefotaxime, Cefpimizole, Cefpiramide, Cefpodoxime, Cefsulodin, Cefteram, Ceftibuten, Ceftiolene, Ceftizoxime, Flomoxef, Latamoxef, Cefepime, Cefozopran, Cefpirome, Cefquinome, Ceftobiprole, Ceftaroline, CXA-101, RWJ-54428, MC-04,546, ME1036, Ceftiofur, Cefquinome, Cefovecin, RWJ-442831, RWJ-333441, or RWJ-333442.

### Claim 63 (depends on 61)

The method of claim 61, wherein the β-lactam antibacterial agent is selected from Ceftazidime, Biapenem, Doripenem, Ertapenem, Imipenem, Meropenem, or Panipenem.

### Claim 64 (depends on 61)

The method of claim 61, wherein the β-lactam antibacterial agent is selected from Aztreonam, Tigemonam, BAL30072, SYN 2416, or Carumonam.

### Claim 65 (depends on 61)

The method of claim 61, wherein the β-lactam antibacterial agent is a penicillin, cephalosporin, carbapenem, monobactam, bridged monobactam, or combination thereof.

### Claim 66 (depends on 65)

The method of claim 65, wherein the penicillin is benzathine penicillin, benzylpenicillin, phenoxymethylpenicillin, procaine, penicillin, oxacillin, methicillin, dicloxacillin, flucloxacillin, temocillin, amoxicillin, ampicillin, co-amoxiclav, azlocillin, carbenicillin, ticarcillin, mezlocillin, piperacillin, apalcillin, hetacillin, bacampicillin, sulbenicillin, mecicilam, pevmecillinam, ciclacillin, talapicillin, aspoxicillin, cloxacillin, nafcillin, pivampicillin, or a combination thereof.

### Claim 67 (depends on 65)

The method of claim 65, wherein the cephalosporin is cephalothin, cephaloridin, cefaclor, cefadroxil, cefamandole, cefazolin, cephalexin, cephradine, ceftizoxime, cefoxitin, cephacetril, cefotiam, cefotaxime, cefsulodin, cefoperazone, ceftizoxime, cefinenoxime, cefinetazole, cephaloglycin, cefonicid, cefodizime, cefpirome, ceftazidime, ceftriaxone, cefpiramide, cefbuperazone, cefozopran, cefepim, cefoselis, cefluprenam, cefuzonam, cefpimizole, cefclidin, cefixime, ceftibuten, cefdinir, cefpodoxime axetil, cefpodoxime proxetil, cefteram pivoxil, cefetamet pivoxil, cefcapene pivoxil, cefditoren pivoxil, cefuroxime, cefuroxime axetil, loracarbacef, latamoxef, or a combination thereof.

### Claim 68 (depends on 65)

The method of claim 65, wherein the cephalosporin is an anti-MRSA cephalosporin.

### Claim 69 (depends on 65)

The method of claim 65, wherein the anti-MRSA cephalosporin is cefiobiprole, cefiaroline, or a combination thereof.

### Claim 70 (depends on 65)

The method of claim 65, wherein the carbapenem is imipenem, meropenem, ertapenem, faropenem, doripenem, biapenem, panipenem, or a combination thereof.

### Claim 71 (depends on 65)

The method of claim 65, wherein the carbapenem is an anti-MRSA carbapenem.

### Claim 72 (depends on 65)

The method of claim 65, wherein the anti-MRSA carbapenem is PZ601 or ME1036.

### Claim 73 (depends on 65)

The method of claim 65, wherein the monobactam is aztreonam, carumonam, BAL30072, or a combination thereof.

### Claim 74 (depends on 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73)

The method of any one of claims 58 to 73, wherein the subject is a mammal.

### Claim 75 (depends on 74)

The method of claim 74, wherein the mammal is a human.

### Claim 76 (depends on 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75)

The method of any one of claims 58 to 75, wherein the infection comprises a bacteria selected from Pseudomonas acidovorans, Pseudomonas alcaligenes, Pseudomonas putida, Burkholderia cepacia, Aeromonas hydrophilia, Francisella tularensis, Morganella morganii, Proteus mirabilis, Proteus vulgaris, Providencia alcalifaciens, Providencia rettgeri, Providencia stuartii, Acinetobacter baumannii, Bordetella pertussis, Bordetella para pertussis, Bordetella bronchiseptica, Haemophilus ducreyi, Pasteurella multocida, Pasteurella haemolytica, Branhamella catarrhalis, Borrelia burgdorferi, Kingella, Gardnerella vaginalis, Bacteroides distasonis, Bacteroides 3452A homology group, Clostridium difficile, Mycobacterium tuberculosis, Mycobacterium avium, Mycobacterium intracellulare, Mycobacterium leprae, Corynebacterium diphtheriae, Corynebacterium ulcerans, Streptococcus pneumoniae, Streptococcus agalactiae, Streptococcus pyogenes, Enterococcus faecalis, Enterococcus faecium, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus saprophyticus, Staphylococcus intermedius, Staphylococcus hyicus subsp. hyicus, Staphylococcus haemolyticus, Staphylococcus hominis, or Staphylococcus saccharolyticus.

### Claim 77 (depends on 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75)

The method of any one of claims 58 to 75, wherein the infection comprises a bacteria selected from Pseudomonas aeruginosa, Pseudomonas jluorescens, Stenotrophomonas maltophilia, Escherichia coli, Citrobacter freundii, Salmonella typhimurium, Salmonella typhi, Salmonella paratyphi, Salmonella enteritidis, Shigella dysenteriae, Shigella jlexneri, Shigella sonnei, Enterobacter cloacae, Enterobacter aerogenes, Klebsiella pneumoniae, Klebsiella oxytoca, Serratia marcescens, Acinetobacter caicoaceticus, Acinetobacter haemolyticus, Yersinia enterocolitica, Yersinia pestis, Yersinia pseudotuberculosis, Yersinia intermedia, Haemophilus injluenzae, Haemophilus parainjluenzae, Haemophilus haemolyticus, Haemophilus parahaemolyticus, Helicobacter pylori, Campylobacter fetus, Campylobacter jejuni, Campylobacter coli, Vibrio cholerae, Vibrio parahaemolyticus, Legionella pneumophila, Listeria monocytogenes, Neisseria gonorrhoeae, Neisseria meningitidis, Moraxella, Bacteroides fragilis, Bacteroides vulgatus, Bacteroides ovalus, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides eggerthii, or Bacteroides splanchnicus.

### Claim 78

A pharmaceutical composition, comprising:
a monosaccharide or monosaccharide derivative or monosaccharide derivative and
a compound of Formula (III):
or pharmaceutically acceptable salts thereof, wherein:
A is selected from the group consisting of C5-10 carbocyclyl, C6-10 aryl, 5-10 membered heteroaryl, and 5-10 membered heterocyclyl;
Xa is —C(RgRh)—, —O—, —S—, —S(O)—, —S(O)2—, or —NR1—;
Ra is selected from the group consisting of —H, halogen, optionally substituted —C1-6 alkyl, —OH, —C(O)OR, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, optionally substituted —S—C1-6 alkyl, —C(O)NR1R2, —S(O)2NR1R2, —CN, optionally substituted —S(O)—C1-6 alkyl, optionally substituted —S(O)2—C1-6 alkyl, and a carboxylic acid isoster;
Rb is selected from the group consisting of —H, halogen, optionally substituted —C1-6 alkyl, —OH, —C(O)OR, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, optionally substituted —S—C1-6 alkyl, —C(O)NR1R2, —S(O)2NR1R2, —CN, optionally substituted —S(O)—C1-6 alkyl, optionally substituted —S(O)2—C1-6 alkyl, and a carboxylic acid isoster, and
Rc is selected from the group consisting of —OH, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, or Rb and Rc together with intervening atoms form a 5-8 membered boron ester ring, optionally comprising additional 1-3 heteroatoms selected from Oxygen (O), Sulfur(S) or Nitrogen (N);
Rd is selected from the group consisting of hydrogen, —OH, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, or
when Rb and Rc do not together form a 5-8 membered boron ester ring, then optionally Rc and Rd together with intervening atoms form a 5-15 membered boron ester or amide ring, optionally comprising additional 1-3 heteroatoms selected from O, S, and N;
Re is independently selected from the group consisting of hydrogen, optionally substituted C1-6alkyl, optionally substituted C3-7cycloalkyl, optionally substituted C6-10aryl, optionally substituted 5-10 membered heteroaryl, and optionally substituted 3-10 membered heterocyclyl, or Rd and Re together with the nitrogen to which they are attached form a 5-8 membered heterocyclic ring, optionally comprising additional 1-3 heteroatoms selected from O, S or N;
Rf is independently selected from the group consisting of —H, —OH, —C(O)G, —C(O)OG, —S(O)2G, —C(═NR1R2)G, —C(═NOR3)G, optionally substituted C1-6 alkyl, optionally substituted —O—C1-6alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted C6-10 aryl, optionally substituted 5-10 membered heteroaryl, and optionally substituted 3-10 membered heterocyclyl;
Rg and Rh are each independently selected from the group consisting of —H, C1-6 alkyl, —OH, —OC1-6alkyl, —SC1-6alkyl, C3-10cycloalkyl, C2-10alkenyl, C2-10alkynyl, —NR1C(O)R5, —NR1S(O)2R3, —C(O)R5, —C(O)OR3-alkylaryl, optionally substituted C6-10 aryl, optionally substituted —O—C6-10aryl, —CN, optionally substituted 5-10 membered heteroaryl, optionally substituted —O-heteroaryl, optionally substituted 3-10 membered heterocyclyl, —S(O)(R3)R4, —S(O)2R3, —R1—O—COOR3, or Rg and Rh together with the carbon to which they are attached form a C3-8 cycloalkyl or a 4-8 membered heterocyclyl;
R is selected from the group consisting of —H, halogen, —C1-9alkyl, —CR5R6OC(O)C1-9alkyl, —CR5R6OC(O)OC1-9alkyl, and
G is selected from the group consisting of hydrogen, —NR1R2, —CH2N3, —C(O)NR1R2, —CH2C(O)NR1R2, —CH2S(O)2NR1R2, —(CH2)n—Y—Z, —(CH2)n—Y—X, —O—(CH2)n—C(O)NR1R2, —SR3, —CH2NR1C(O)R5, —C(═NOR3)—X, —C(═NOR3)—Z, —C(O)OR3, —C(O)—X, —C(O)—Z, —S(O)2R3, —C(O)NR1OR3, —NR1(OR3), —NR1C(O)R3, —NR1C(O)NR2R1a, —NR1C(O)OR3, —NR1S(O)2R3, —NR1S(O)2NR2R1a, —NR1NR2R1a, —C(O)NR1NR2R1a, —S(O)2NR1NR2R1a, —C(═NR1)R5, —C(═NR1)NR2R1a, —NR1CR3(═NR2), and —NR1C(═NR2)NR1aR2a, optionally substituted C1-10 alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-7 carbocyclyl, optionally substituted 5-10 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
X is hydrogen or optionally substituted C1-9alkyl;
Y is selected from a group consisting of —S—, —S(O)—, —S(O)2—, —CH2—, —O—, —O—CH2—, —C(O)—, and —NR1—;
Z is selected from optionally substituted C3-8 cycloalkyl, optionally substituted 3-10 membered heterocyclyl, optionally substituted C6-10 aryl, optionally substituted 5-10 membered heteroaryl;
each R1, R2, R1a and R2a are independently selected from the group consisting of —H, optionally substituted —C1-10alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted 3-8 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
R3 is hydrogen, optionally substituted C1-10alkyl, —optionally substituted C1-10alkyl-COOH, optionally substituted C3-7 cycloalkyl, optionally substituted 3-8 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
each R5 and R6 are independently selected from the group consisting of —H, —OH, —optionally substituted alkoxyl, optionally substituted —C1-10alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted 3-8 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl; R4 is present 1 to 5 times and each R4 is independently selected from the group consisting of —H, —OH, halogen, —CF3, C1-C6 alkenyl, C1-C6 alkynyl, C1-C6 heteroalkyl, C3-C7 carbocyclyl, 5-10 membered heterocyclyl, aryl, 5-10 membered heteroaryl, cyano, C1-C6 alkoxy(C1-C6)alkyl, aryloxy, sulfhydryl (mercapto), and —CH2)m—Y′—(CH2)pM′;
m and p are independently 0 to 3;
Y′ is selected from the group consisting of —S—, —S(O)—, —S(O)2—, —O—, —CR5R6—, and —NR1—;
M′ is selected from the group consisting of —C(O)NR1R2; —C(O)NR1OR3; —NR1C(O)R5; —NR1C(O)NR2R1a; NR1C(O)OR3; —NR1S(O)2R3; —NR1S(O)2NR2R1a; C(═NR1)R5; C(NR1)NR2R1a; —NR1CR5(═NR2); NR1C(═NR)NR1aR2a; C1-4 alkyl optionally substituted with 0-2 substituents selected from the group consisting, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; C3-10 cycloalkyl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; C6-10 aryl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; 5 to 10 membered heteroaryl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; and 4 to 10 membered heterocyclyl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR1, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; and
each n is independently 0-3.

### Claim 79 (depends on 78)

The composition of claim 78, wherein A is selected from the group consisting of phenyl, biphenyl, naphthalenyl, phenanthrenyl, anthracenyl, tetralinyl, fluorenyl, indenyl, indanyl, pyridyl, pyrrolyl, oxazolyl, indolyl and thienyl.

### Claim 80 (depends on 78, 79)

The composition of claim 78 or 79, wherein the compound of formula (III) has the structure of Formula (IIIa):
or pharmaceutically acceptable salts thereof, wherein J, L, and M are independently selected from the group consisting of CR4 and N.

### Claim 81 (depends on 78, 79, 80)

The composition of any one of claims 78 to 80, wherein Rb is —OH or optionally substituted —OC1-6alkyl.

### Claim 82 (depends on 78, 79, 80, 81)

The composition of any one of claims 78 to 81, wherein Rc is —OH or optionally substituted —OC1-6alkyl.

### Claim 83 (depends on 78, 79, 80, 81, 82)

The composition of any one of claims 78 to 82, wherein Rc is —OH and Rd is —OH.

### Claim 84 (depends on 78, 79, 80)

The composition of any one of claims 78 to 80, wherein Rb and Rc together with intervening atoms form a 5-8 membered boron ester ring, optionally comprising additional 1-3 heteroatoms selected from Oxygen (O), Sulfur (S) or Nitrogen (N).

### Claim 85 (depends on 84)

The composition of claim 84, wherein the compound of formula (III) has the structure of Formula (IIIb):
or pharmaceutically acceptable salts thereof, wherein J, L, and M are independently selected from the group consisting of CR4 and N.

### Claim 86 (depends on 85)

The composition of claim 85, wherein the compound of formula (III) has the structure of Formula (IIIc):
or pharmaceutically acceptable salts thereof.

### Claim 87 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86)

The composition of any one of claims 78 to 86, wherein Ra is C(O)OR and R is —O(CH2)nOC(O)—C1-9 alkyl.

### Claim 88 (depends on 87)

The composition of claim 87, wherein R is —OCH2OC(O)—C(CH3)3, —OCH2OC(O)—CH(CH3)2, or —OCH2OC(O)—(CH2)nCH3.

### Claim 89 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86)

The composition of any one of claims 78 to 86, wherein Ra is C(O)OH.

### Claim 90 (depends on 78, 79, 80, 81, 82, 84, 85, 86, 87, 88, 89)

The composition of any one of claims 78 to 82 and 84 to 89, wherein Rd is selected from hydrogen, —OH, halogen, —COOR, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1.

### Claim 91 (depends on 78, 79, 80, 81, 82, 84, 85, 86, 87, 88, 89, 90)

The composition of any one of claims 78 to 82 and 84 to 90, wherein Rd is —OH or optionally substituted —O—C1-6 alkyl.

### Claim 92 (depends on 91)

The composition of claim 91, wherein Rd is —OH.

### Claim 93 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92)

The composition of any one of claims 78 to 92, wherein Re is independently selected from the group consisting of hydrogen, optionally substituted C1-6alkyl, optionally substituted C3-7cycloalkyl, optionally substituted C6-10aryl, optionally substituted 5-10 membered heteroaryl, and optionally substituted 3-10 membered heterocyclyl.

### Claim 94 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93)

The composition of any one of claims 78 to 93, wherein Rf is independently selected from the group consisting of —C(O)G, —C(O)OG, and —S(O)2G.

### Claim 95 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94)

The composition of any one of claims 78 to 94, wherein Rf is independently selected from —C(O)G or —C(O)OG.

### Claim 96 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein G is selected from the group consisting of

### Claim 97 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein G is —NH2.

### Claim 98 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein G is —NH—C1-4alkyl.

### Claim 99 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein G is —C(O)NR1R2 and R1 and R2 in G are each independently selected from —H and C1-4alkyl.

### Claim 100 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein G is —CH2C(O)NR1R2 and R1 and R2 in G are each independently selected from —H and C1-4alkyl.

### Claim 101 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein
G is —O—(CH2)n—C(O)NR1R2;
n in G is 0-3; and
R1 and R2 in G are each independently selected from —H and C1-4alkyl.

### Claim 102 (depends on 101)

The composition of claim 101, wherein G is —O—CH2—C(O)NH2.

### Claim 103 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein
G is —(CH2)n—Y—Z;
n in G is 0-3,
Y is —S—; and
Z is selected from the group consisting of imidazole, N-methylimidazole, aminoimidazole, triazole, N-methyl triazole, aminotriazole, tetrazole, N-methyltetrazole, aminotetrazole, thiazole, aminothiazole, thiadiazole, aminothiadiazole, oxazole, oxadiazole, pyridine, pyridazine, pyrimidine, pyrazine, azetidine and piperdine, each optionally substituted with one or more C1-4alkyl, —NR1R2, hydroxy, or halogen.

### Claim 104 (depends on 103)

The composition of claim 103, wherein n in G is 0.

### Claim 105 (depends on 103)

The composition of claim 103, wherein n in G is 1.

### Claim 106 (depends on 103)

The composition of claim 103, wherein Z is thiadiazole optionally substituted with one or more C1-4alkyl, —NR1R2, hydroxy, or halogen.

### Claim 107 (depends on 103)

The composition of claim 103, wherein Z is aminothiadiazole optionally substituted with one or more C1-4alkyl, —NR1R2, hydroxy, or halogen.

### Claim 108 (depends on 103)

The composition of claim 103, wherein Z is azitidine optionally substituted with one or more C1-4alkyl, —NR1R2, hydroxy, or halogen.

### Claim 109 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein
G is —(CH2)n—Y—X;
n in G is 0-3;
Y is —S—; and
X is hydrogen or optionally C1-4alkyl.

### Claim 110 (depends on 109)

The composition of claim 109, wherein n in G is 0.

### Claim 111 (depends on 109)

The composition of claim 109, wherein n in G is 1.

### Claim 112 (depends on 109)

The composition of claim 109, wherein X is —CH3.

### Claim 113 (depends on 109)

The composition of claim 109, wherein X is —CH2CN.

### Claim 114 (depends on 109)

The composition of claim 109, wherein X is —CH2N3.

### Claim 115 (depends on 109)

The composition of claim 109, wherein X is —CH2F.

### Claim 116 (depends on 109)

The composition of claim 109, wherein X is —CHF2.

### Claim 117 (depends on 109)

The composition of claim 109, wherein X is —CF3.

### Claim 118 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein
G is —(CH2)n—Y—Z;
n in G is 0-3,
Y is —CH2—, —O—, —O—CH2—, —C(O)—; and
Z is selected from the group consisting of phenyl, napthal, indole, pyrrolidine, thiophene, cyclopropyl, or cyclohexyl, each optionally substituted with one or more C1-4alkyl, —NR1R2, hydroxy, or halogen.

### Claim 119 (depends on 118)

The composition of claim 118, wherein n in G is 1.

### Claim 120 (depends on 118)

The composition of claim 118, wherein n in G is 2.

### Claim 121 (depends on 118)

The composition of claim 118, wherein Z is selected from

### Claim 122 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95)

The composition of any one of claims 78 to 95, wherein
G is —(CH2)n—Y—X;
n in G is 0-3;
Y is —O— or —CH2—; and
X is C1-4alkyl optionally substituted with one or more halogen, cyano, or azido.

### Claim 123 (depends on 122)

The composition of claim 122, wherein n in G is 0 and Y is —O—.

### Claim 124 (depends on 122)

The composition of claim 122, wherein n in G is 1.

### Claim 125 (depends on 122)

The composition of claim 122, wherein n in G is 2.

### Claim 126 (depends on 122)

The composition of claim 122, wherein X is optionally substituted C1-4alkyl.

### Claim 127 (depends on 78)

The composition of claim 78, wherein the compound of formula (III) has the structure selected from the group consisting of
or pharmaceutically acceptable salts thereof.

### Claim 128 (depends on 78)

The composition of claim 78, wherein the compound of formula (III) has the structure selected from the group consisting of
or pharmaceutically acceptable salts thereof.

### Claim 129 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128)

The composition of any one of claims 78 to 128, wherein the monosaccharide or monosaccharide derivative is meglumine.

### Claim 130 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128)

The composition of any one of claims 78 to 128, wherein the pH of the composition is in the range of about 5 to about 9.

### Claim 131 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128)

The composition of any one of claims 78 to 128, wherein the pH of the composition is in the range of about 6 to about 8.

### Claim 132 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128)

The composition of any one of claims 78 to 128, wherein the pH of the composition is in the range of about 6 to about 7.5.

### Claim 133 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128)

The composition of any one of claims 78 to 128, wherein the pH of the composition is in the range of about 7.1 to about 7.3.

### Claim 134 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128)

The composition of any one of claims 78 to 128, wherein the pH of the composition is about 7.2.

### Claim 135 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134)

The composition of any one of claims 78 to 134, further comprising an additional pharmaceutically acceptable carrier or excipient.

### Claim 136 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135)

The composition of any one of claims 78 to 135, further comprising one or more additional medicament.

### Claim 137 (depends on 136)

The composition of claim 136, the additional medicament is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent.

### Claim 138 (depends on 137)

The composition of claim 137, wherein the additional medicament is a β-lactam antibacterial agent.

### Claim 139 (depends on 138)

The composition of claim 138, wherein the β-lactam antibacterial agent is selected from Amoxicillin, Ampicillin (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin), Epicillin, Carbenicillin (Carindacillin), Ticarcillin, Temocillin, Azlocillin, Piperacillin, Mezlocillin, Mecillinam (Pivmecillinam), Sulbenicillin, Benzylpenicillin (G), Clometocillin, Benzathine, benzylpenicillin, Procaine benzylpenicillin, Azidocillin, Penamecillin, Phenoxymethylpenicillin, (V), Propicillin, Benzathine phenoxymethylpenicillin, Pheneticillin, Cloxacillin (Dicloxacillin, Flucloxacillin), Oxacillin, Meticillin, Nafcillin, Faropenem, Tomopenem, Razupenem, Cefazolin, Cefacetrile, Cefadroxil, Cefalexin, Cefaloglycin, Cefalonium, Cefaloridine, Cefalotin, Cefapirin, Cefatrizine, Cefazedone, Cefazaflur, Cefradine, Cefroxadine, Ceftezole, Cefaclor, Cefamandole, Cefminox, Cefonicid, Ceforanide, Cefotiam, Cefprozil, Cefbuperazone, Cefuroxime, Cefuzonam, Cefoxitin, Cefotetan, Cefmetazole, Loracarbef, Cefixime, Ceftriaxone, Cefcapene, Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefmenoxime, Cefodizime, Cefoperazone, Cefotaxime, Cefpimizole, Cefpiramide, Cefpodoxime, Cefsulodin, Cefteram, Ceftibuten, Ceftiolene, Ceftizoxime, Flomoxef, Latamoxef, Cefepime, Cefozopran, Cefpirome, Cefquinome, Ceftobiprole, Ceftaroline, CXA-101, RWJ-54428, MC-04,546, ME1036, Ceftiofur, Cefquinome, Cefovecin, RWJ-442831, RWJ-333441, or RWJ-333442.

### Claim 140 (depends on 138)

The composition of claim 138, wherein the β-lactam antibacterial agent is selected from Ceftazidime, Biapenem, Doripenem, Ertapenem, Imipenem, Meropenem, or Panipenem.

### Claim 141 (depends on 138)

The composition of claim 138, wherein the β-lactam antibacterial agent is selected from Aztreonam, Tigemonam, BAL30072, SYN 2416, or Carumonam.

### Claim 142 (depends on 138)

The composition of claim 138, wherein the β-lactam antibacterial agent is a penicillin, cephalosporin, carbapenem, monobactam, bridged monobactam, or combination thereof, wherein the penicillin is benzathine penicillin, benzylpenicillin, phenoxymethylpenicillin, procaine, penicillin, oxacillin, methicillin, dicloxacillin, flucloxacillin, temocillin, amoxicillin, ampicillin, co-amoxiclav, azlocillin, carbenicillin, ticarcillin, mezlocillin, piperacillin, apalcillin, hetacillin, bacampicillin, sulbenicillin, mecicilam, pevmecillinam, ciclacillin, talapicillin, aspoxicillin, cloxacillin, nafcillin, pivampicillin, or a combination thereof.

### Claim 143 (depends on 142)

The composition of claim 142, wherein the cephalosporin is cephalothin, cephaloridin, cefaclor, cefadroxil, cefamandole, cefazolin, cephalexin, cephradine, ceftizoxime, cefoxitin, cephacetril, cefotiam, cefotaxime, cefsulodin, cefoperazone, ceftizoxime, cefinenoxime, cefinetazole, cephaloglycin, cefonicid, cefodizime, cefpirome, ceftazidime, ceftriaxone, cefpiramide, cefbuperazone, cefozopran, cefepim, cefoselis, cefluprenam, cefuzonam, cefpimizole, cefclidin, cefixime, ceftibuten, cefdinir, cefpodoxime axetil, cefpodoxime proxetil, cefteram pivoxil, cefetamet pivoxil, cefcapene pivoxil, cefditoren pivoxil, cefuroxime, cefuroxime axetil, loracarbacef, latamoxef, or a combination thereof.

### Claim 144 (depends on 142)

The composition of claim 142, wherein the cephalosporin is an anti-MRSA cephalosporin.

### Claim 145 (depends on 144)

The composition of claim 144, wherein the anti-MRSA cephalosporin is cefiobiprole, cefiaroline, or a combination thereof.

### Claim 146 (depends on 142)

The composition of claim 142, wherein the carbapenem is imipenem, meropenem, ertapenem, faropenem, doripenem, biapenem, panipenem, or a combination thereof.

### Claim 147 (depends on 146)

The composition of claim 146, wherein the carbapenem is an anti-MRSA carbapenem.

### Claim 148 (depends on 147)

The composition of claim 147, wherein the anti-MRSA carbapenem is PZ601 or ME1036.

### Claim 149 (depends on 142)

The composition of claim 142, wherein the monobactam is aztreonam, carumonam, BAL30072, or a combination thereof.

### Claim 150 (depends on 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149)

A method of treating or preventing a bacterial infection, comprising administering to a subject in need thereof, a composition according to any one of claims 78-149.

### Claim 151 (depends on 150)

The method of claim 150, further comprising administering to the subject an additional medicament.

### Claim 152 (depends on 150, 151)

The method of claim 150 or 151, wherein the additional medicament is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent.

### Claim 153 (depends on 152)

The method of claim 152, wherein the additional medicament is a β-lactam antibacterial agent.

### Claim 154 (depends on 153)

The method of claim 153, wherein the β-lactam antibacterial agent is selected from Amoxicillin, Ampicillin (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin), Epicillin, Carbenicillin (Carindacillin), Ticarcillin, Temocillin, Azlocillin, Piperacillin, Mezlocillin, Mecillinam (Pivmecillinam), Sulbenicillin, Benzylpenicillin (G), Clometocillin, Benzathine, benzylpenicillin, Procaine benzylpenicillin, Azidocillin, Penamecillin, Phenoxymethylpenicillin, (V), Propicillin, Benzathine phenoxymethylpenicillin, Pheneticillin, Cloxacillin (Dicloxacillin, Flucloxacillin), Oxacillin, Meticillin, Nafcillin, Faropenem, Tomopenem, Razupenem, Cefazolin, Cefacetrile, Cefadroxil, Cefalexin, Cefaloglycin, Cefalonium, Cefaloridine, Cefalotin, Cefapirin, Cefatrizine, Cefazedone, Cefazaflur, Cefradine, Cefroxadine, Ceftezole, Cefaclor, Cefamandole, Cefminox, Cefonicid, Ceforanide, Cefotiam, Cefprozil, Cefbuperazone, Cefuroxime, Cefuzonam, Cefoxitin, Cefotetan, Cefmetazole, Loracarbef, Cefixime, Ceftriaxone, Cefcapene, Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefmenoxime, Cefodizime, Cefoperazone, Cefotaxime, Cefpimizole, Cefpiramide, Cefpodoxime, Cefsulodin, Cefteram, Ceftibuten, Ceftiolene, Ceftizoxime, Flomoxef, Latamoxef, Cefepime, Cefozopran, Cefpirome, Cefquinome, Ceftobiprole, Ceftaroline, CXA-101, RWJ-54428, MC-04,546, ME1036, Ceftiofur, Cefquinome, Cefovecin, RWJ-442831, RWJ-333441, or RWJ-333442.

### Claim 155 (depends on 153)

The method of claim 153, wherein the β-lactam antibacterial agent is selected from Ceftazidime, Biapenem, Doripenem, Ertapenem, Imipenem, Meropenem, or Panipenem.

### Claim 156 (depends on 153)

The method of claim 153, wherein the β-lactam antibacterial agent is selected from Aztreonam, Tigemonam, BAL30072, SYN 2416, or Carumonam.

### Claim 157 (depends on 153)

The method of claim 153, wherein the β-lactam antibacterial agent is a penicillin, cephalosporin, carbapenem, monobactam, bridged monobactam, or combination thereof.

### Claim 158 (depends on 157)

The method of claim 157, wherein the penicillin is benzathine penicillin, benzylpenicillin, phenoxymethylpenicillin, procaine, penicillin, oxacillin, methicillin, dicloxacillin, flucloxacillin, temocillin, amoxicillin, ampicillin, co-amoxiclav, azlocillin, carbenicillin, ticarcillin, mezlocillin, piperacillin, apalcillin, hetacillin, bacampicillin, sulbenicillin, mecicilam, pevmecillinam, ciclacillin, talapicillin, aspoxicillin, cloxacillin, nafcillin, pivampicillin, or a combination thereof.

### Claim 159 (depends on 157)

The method of claim 157, wherein the cephalosporin is cephalothin, cephaloridin, cefaclor, cefadroxil, cefamandole, cefazolin, cephalexin, cephradine, ceftizoxime, cefoxitin, cephacetril, cefotiam, cefotaxime, cefsulodin, cefoperazone, ceftizoxime, cefinenoxime, cefinetazole, cephaloglycin, cefonicid, cefodizime, cefpirome, ceftazidime, ceftriaxone, cefpiramide, cefbuperazone, cefozopran, cefepim, cefoselis, cefluprenam, cefuzonam, cefpimizole, cefclidin, cefixime, ceftibuten, cefdinir, cefpodoxime axetil, cefpodoxime proxetil, cefteram pivoxil, cefetamet pivoxil, cefcapene pivoxil, cefditoren pivoxil, cefuroxime, cefuroxime axetil, loracarbacef, latamoxef, or a combination thereof.

### Claim 160 (depends on 157)

The method of claim 157, wherein the cephalosporin is an anti-MRSA cephalosporin.

### Claim 161 (depends on 160)

The method of claim 160, wherein the anti-MRSA cephalosporin is cefiobiprole, cefiaroline, or a combination thereof.

### Claim 162 (depends on 157)

The method of claim 157, wherein the carbapenem is imipenem, meropenem, ertapenem, faropenem, doripenem, biapenem, panipenem, or a combination thereof.

### Claim 163 (depends on 157)

The method of claim 157, wherein the carbapenem is an anti-MRSA carbapenem.

### Claim 164 (depends on 163)

The method of claim 163, wherein the anti-MRSA carbapenem is PZ601 or ME1036.

### Claim 165 (depends on 157)

The method of claim 157, wherein the monobactam is aztreonam, carumonam, BAL30072, or a combination thereof.

### Claim 166 (depends on 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165)

The method of any one of claims 150 to 165, wherein the subject is a mammal.

### Claim 167 (depends on 166)

The method of claim 166, wherein the mammal is a human.

### Claim 168 (depends on 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167)

The method of any one of claims 150 to 167, wherein the infection comprises a bacteria selected from Pseudomonas acidovorans, Pseudomonas alcaligenes, Pseudomonas putida, Burkholderia cepacia, Aeromonas hydrophilia, Francisella tularensis, Morganella morganii, Proteus mirabilis, Proteus vulgaris, Providencia alcalifaciens, Providencia rettgeri, Providencia stuartii, Acinetobacter baumannii, Bordetella pertussis, Bordetella para pertussis, Bordetella bronchiseptica, Haemophilus ducreyi, Pasteurella multocida, Pasteurella haemolytica, Branhamella catarrhalis, Borrelia burgdorferi, Kingella, Gardnerella vaginalis, Bacteroides distasonis, Bacteroides 3452A homology group, Clostridium difficile, Mycobacterium tuberculosis, Mycobacterium avium, Mycobacterium intracellulare, Mycobacterium leprae, Corynebacterium diphtheriae, Corynebacterium ulcerans, Streptococcus pneumoniae, Streptococcus agalactiae, Streptococcus pyogenes, Enterococcus faecalis, Enterococcus faecium, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus saprophyticus, Staphylococcus intermedius, Staphylococcus hyicus subsp. hyicus, Staphylococcus haemolyticus, Staphylococcus hominis, or Staphylococcus saccharolyticus.

### Claim 169 (depends on 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167)

The method of any one of claims 150 to 167, wherein the infection comprises a bacteria selected from Pseudomonas aeruginosa, Pseudomonas jluorescens, Stenotrophomonas maltophilia, Escherichia coli, Citrobacter freundii, Salmonella typhimurium, Salmonella typhi, Salmonella paratyphi, Salmonella enteritidis, Shigella dysenteriae, Shigella jlexneri, Shigella sonnei, Enterobacter cloacae, Enterobacter aerogenes, Klebsiella pneumoniae, Klebsiella oxytoca, Serratia marcescens, Acinetobacter caicoaceticus, Acinetobacter haemolyticus, Yersinia enterocolitica, Yersinia pestis, Yersinia pseudotuberculosis, Yersinia intermedia, Haemophilus injluenzae, Haemophilus parainjluenzae, Haemophilus haemolyticus, Haemophilus parahaemolyticus, Helicobacter pylori, Campylobacter fetus, Campylobacter jejuni, Campylobacter coli, Vibrio cholerae, Vibrio parahaemolyticus, Legionella pneumophila, Listeria monocytogenes, Neisseria gonorrhoeae, Neisseria meningitidis, Moraxella, Bacteroides fragilis, Bacteroides vulgatus, Bacteroides ovalus, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides eggerthii, or Bacteroides splanchnicus.

### Claim 170

A chemical complex, comprising a complex between a monosaccharide or monosaccharide derivative and a compound having the structure of formula (III):
or pharmaceutically acceptable salts thereof, wherein:
A is selected from the group consisting of C5-10 carbocyclyl, C6-10 aryl, 5-10 membered heteroaryl, and 5-10 membered heterocyclyl;
Xa is —C(RgRh)—, —O—, —S—, —S(O)—, —S(O)2—, or —NR1—;
Ra is selected from the group consisting of —H, halogen, optionally substituted —C1-6 alkyl, —OH, —C(O)OR, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, optionally substituted —S—C1-6 alkyl, —C(O)NR1R2, —S(O)2NR1R2, —CN, optionally substituted —S(O)—C1-6 alkyl, optionally substituted —S(O)2—C1-6 alkyl, and a carboxylic acid isoster;
Rb is selected from the group consisting of —H, halogen, optionally substituted —C1-6 alkyl, —OH, —C(O)OR, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, optionally substituted —S—C1-6 alkyl, —C(O)NR1R2, —S(O)2NR1R2, —CN, optionally substituted —S(O)—C1-6 alkyl, optionally substituted —S(O)2—C1-6 alkyl, and a carboxylic acid isoster, and
Rc is selected from the group consisting of —OH, optionally substituted O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, or Rb and Rc together with intervening atoms form a 5-8 membered boron ester ring, optionally comprising additional 1-3 heteroatoms selected from Oxygen (O), Sulfur(S) or Nitrogen (N);
Rd is selected from the group consisting of hydrogen, —OH, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R1, or
when Rb and Rc do not together form a 5-8 membered boron ester ring, then optionally Rc and Rd together with intervening atoms form a 5-15 membered boron ester or amide ring, optionally comprising additional 1-3 heteroatoms selected from O, S, and N;
Re is independently selected from the group consisting of hydrogen, optionally substituted C1-6alkyl, optionally substituted C3-7cycloalkyl, optionally substituted C6-10aryl, optionally substituted 5-10 membered heteroaryl, and optionally substituted 3-10 membered heterocyclyl, or Rd and Re together with the nitrogen to which they are attached form a 5-8 membered heterocyclic ring, optionally comprising additional 1-3 heteroatoms selected from O, S or N;
Rf is independently selected from the group consisting of —H, —OH, —C(O)G, —C(O)OG, —S(O)2G, —C(═NR1R2)G, —C(═NOR3)G, optionally substituted C1-6 alkyl, optionally substituted —O—C1-6alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted C6-10 aryl, optionally substituted 5-10 membered heteroaryl, and optionally substituted 3-10 membered heterocyclyl;
Rg and Rh are each independently selected from the group consisting of —H, C1-6 alkyl, —OH, —OC1-6alkyl, —SC1-6alkyl, C3-10cycloalkyl, C2-10alkenyl, C2-10alkynyl, —NR1C(O)R5, —NR1S(O)2R3, —C(O)R5, —C(O)OR3-alkylaryl, optionally substituted C6-10 aryl, optionally substituted —O—C6-10aryl, —CN, optionally substituted 5-10 membered heteroaryl, optionally substituted —O-heteroaryl, optionally substituted 3-10 membered heterocyclyl, —S(O)(R3)R4, —S(O)2R3, —R1—O—COOR3, or Rg and Rh together with the carbon to which they are attached form a C3-8 cycloalkyl or a 4-8 membered heterocyclyl;
R is selected from the group consisting of —H, halogen, —C1-9alkyl, —CR5R6OC(O)C1-9alkyl, —CR5R6OC(O)OC1-9alkyl, and
G is selected from the group consisting of hydrogen, —NR1R2, —CH2N3, —C(O)NR1R2, —CH2C(O)NR1R2, —CH2S(O)2NR1R2, —(CH2)n—Y—Z, —(CH2)n—Y—X, —O—(CH2)n—C(O)NR1R2, —SR3, —CH2NR1C(O)R5, —C(═NOR3)—X, —C(═NOR3)—Z, —C(O)OR3, —C(O)—X, —C(O)—Z, —S(O)2R3, —C(O)NR1OR3, —NR1(OR3), —NR1C(O)R3, —NR1C(O)NR2R1a, —NR1C(O)OR3, —NR1S(O)2R3, —NR1S(O)2NR2R1a, —NR1NR2R1a, —C(O)NR1NR2R1a, —S(O)2NR1NR2R1a, —C(═NR1)R5, —C(═NR1)NR2R1a, —NR1CR3(═NR2), and —NR1C(═NR2)NR1aR2a, optionally substituted C1-10 alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-7 carbocyclyl, optionally substituted 5-10 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
X is hydrogen or optionally substituted C1-9alkyl;
Y is selected from a group consisting of —S—, —S(O)—, —S(O)2—, —CH2—, —O—, —O—CH2—, —C(O)—, and —NR1—;
Z is selected from optionally substituted C3-8 cycloalkyl, optionally substituted 3-10 membered heterocyclyl, optionally substituted C6-10 aryl, optionally substituted 5-10 membered heteroaryl;
each R1, R2, R1a and R2a are independently selected from the group consisting of —H, optionally substituted —C1-10alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted 3-8 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
R3 is hydrogen, optionally substituted C1-10alkyl, —optionally substituted C1-10alkyl-COOH, optionally substituted C3-7 cycloalkyl, optionally substituted 3-8 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
each R5 and R6 are independently selected from the group consisting of —H, —OH, —optionally substituted alkoxyl, optionally substituted —C1-10alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-7 cycloalkyl, optionally substituted 3-8 membered heterocyclyl, optionally substituted C6-10aryl, and optionally substituted 5-10 membered heteroaryl;
R4 is present 1 to 5 times and each R4 is independently selected from the group consisting of —H, —OH, halogen, —CF3, C1-C6 alkenyl, C1-C6 alkynyl, C1-C6 heteroalkyl, C3-C7 carbocyclyl, 5-10 membered heterocyclyl, aryl, 5-10 membered heteroaryl, cyano, C1-C6 alkoxy(C1-C6)alkyl, aryloxy, sulfhydryl (mercapto), and —(CH2)m—Y′—(CH2)pM′;
m and p are independently 0 to 3;
Y′ is selected from the group consisting of —S—, —S(O)—, —S(O)2—, —O—, —CR5R6—, and —NR1—;
M′ is selected from the group consisting of —C(O)NR1R2; —C(O)NR1OR3; —NR1C(O)R5; —NR1C(O)NR2R1a; —NR1C(O)OR3; —NR1S(O)2R3; —NR1S(O)2NR2R1a; —C(═NR1)R5; —C(═NR1)NR2R1a; —NR1CR5(═NR2); —NR1C(═NR2)NR1aR2a; C1-4 alkyl optionally substituted with 0-2 substituents selected from the group consisting, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; C3-10 cycloalkyl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; C6-10 aryl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; 5 to 10 membered heteroaryl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; and 4 to 10 membered heterocyclyl optionally substituted with 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR1, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; and
each n is independently 0-3.

### Claim 171 (depends on 170)

The chemical complex of claim 170, wherein the monosaccharide or monosaccharide derivative is meglumine.