# US 2014/0194384 A1 · Boronic acid derivatives and therapeutic uses thereof

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0194384 A1
- Document ID: US20140194384A1
- Status: Published application
- Kind: A1
- Application number: 14/146,643
- 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/US20140194384A1

## 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 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/04: Antibacterial agents
- A61P 31/06: for tuberculosis
- A61P 31/10: Antimycotics
- A61P 31/12: Antivirals
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- 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.

## Claims

### Claim 1

A compound having the structure of Formula (I):
or pharmaceutically acceptable salts thereof, wherein:
A is selected from the group consisting of C3-10 carbocyclyl, C6-10 aryl, 5-10 membered heteroaryl, and 5-10 membered heterocyclyl;
Xa is —C(ReRf)—, —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, —N(OR3)R2, 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, —N(OR3)R2, 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)R2, 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 —OH, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R2, 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;
Y is selected from the group consisting of —S—, —S(O)—, —S(O)2—, —O—, —CH2— and —NR2—;
G is selected from the group consisting of —NR1R2, —N3, —C(O)NR1R2, —S(O)2NR1R2, —SR3, —OR3, —CH2NR1C(O)R5, —C(═NOR3)—X, C(═NOR3)—Z, —C(O)OR3, —S(O)2R3, —C(O)NR1(OR3), —NR1(OR3), —NR1C(O)R5, —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, —NR1CR5(═NR2), —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;
Re and Rf 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, —S(O)2R3, —R1—O—C(O)OR3, or Re and Rf together with the carbon to which they are attached form a C3-8 cycloalkyl or a 4-8 membered heterocyclyl;
R7 is present 1 to 5 times and each R7 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, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5;
X is hydrogen or optionally substituted C1-9alkyl;
Z is selected from optionally substituted C3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
R is selected from the group consisting of —H, —C1-9alkyl, —CR5R6OC(O)C1-9alkyl, —CR5R6OC(O)OC1-9alkyl, and
each R1, R2, R1a and Rea 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-COOOH, 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;
each R5, R6, R8 and R9 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;
each n is independently 0-3.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Y is —CH2—, —S(O)—, —S(O)2—, —O— or —S—.

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

The compound of claim 1 or 2, wherein Rd is —OH.

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

The compound of any one of claims 1 to 3, wherein X′ is —CH2—.

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

The compound of any one of claims 1 to 4, wherein 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, —N(OR3)R2, optionally substituted —S—C1-6 alkyl, —C(O)NR1R2, —S(O)2NR1R2, CN, optionally substituted —S(O)—C1-6 alkyl, and optionally substituted —S(O)2—C1-6 alkyl.

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

The compound of any one of claims 1 to 6, wherein 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, —N(OR3)R2, optionally substituted —S—C1-6 alkyl, —C(O)NR1R2, —S(O)2NR1R2, —CN, optionally substituted —S(O)—C1-6 alkyl, and optionally substituted —S(O)2—C1-6 alkyl.

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

The compound of any one of claims 1 to 6, wherein Rb is —OH

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

The compound of any one of claims 1 to 7, wherein Rc is —OH.

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

The compound of any one of claims 1 to 5 having the structure of Formula (I′)
or pharmaceutically acceptable salts thereof.

### Claim 10 (depends on 1, 2)

The compound of claim 1 or 2, having the structure of Formula (I-1) or Formula (I-2):
or pharmaceutically acceptable salts thereof, wherein:
J, L, and M are each independently selected from the group consisting of CR7 and N.

### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10)

The compound of any one of claims 1 to 10, wherein R8 is H and R9 is H.

### Claim 12 (depends on 3, 4, 5, 6, 7, 8, 9, 10)

The compound of any one of claims 3 to 10, wherein:
Y is selected from the group consisting of —S—, —O—, —CH2—, and —NH—;
G is selected from the group consisting of —C(O)NR1R2; —C(O)NR1OR3; —NR1C(O)R5; —NR1C(O)NR2R2a; —NR1C(O)OR3; —NR1S(O)2R3; —NR1S(O)2NR2R1a; —C(═NR1)R5; —C(═NR1)NR2R1a; —NR1CR5(═NR5); —NR1C(═NR2)NR1aR2a; 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; 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 heterocyclyl 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;
R is selected from a group consisting of —H, —C1-9alkyl, —CR5R6OC(O)C1-9alkyl, and
each R1, R2, R1a, R1a, R3, R5 and R6 are independently selected from —H and —C1-4alkyl; and
R7 is selected from the group consisting of —H, —C1-4alkyl, —OH, —OC1-4alkyl, and halogen.

### Claim 13 (depends on 10, 11, 12)

The compound of any one of claims 10 to 12, having the structure of Formula (Ia)
or pharmaceutically acceptable salts thereof.

### Claim 14 (depends on 10, 11, 12)

The compound of any one of claims 10 to 12, having the structure of (Ib):
or pharmaceutically acceptable salts thereof.

### Claim 15 (depends on 10, 11, 12)

The compound of any one of claims 10 to 12, having the structure of Formula (Ic)
or pharmaceutically acceptable salts thereof.

### Claim 16 (depends on 10, 11, 12)

The compound of any one of claims 10 to 12, having the structure of (Id):
or pharmaceutically acceptable salts thereof.

### Claim 17 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)

The compound of any one of claims 1-16, wherein Y is —CH2—, —O— or —S—.

### Claim 18 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)

The compound of any one of claims 1-16, wherein Y is —O— or —S—.

### Claim 19 (depends on 10, 11, 12, 13, 14, 15, 16)

The compound of any one of claims 10-16, wherein:
Y is —O— or —S—;
G is selected from the group consisting of phenyl, imidazole, pyrazole, triazole, tetrazole, thiazole, thiadiazole, oxazole, oxadiazole, isoxazole, isothiazole, pyridine, pyrazine, pyrimidine, pyridazine, azetidine, and pyrazine, each optionally substituted by 0-2 substituents selected from the group consisting of C1-4 alkyl, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5, wherein R1, R2 and R5 in G are independently selected from —H and —C1-4alkyl; and
J, L and M are CR7.

### Claim 20 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19)

The compound of any one of claims 1-19, wherein n is 0 or 1.

### Claim 21 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20)

The compound of any one of claims 1-20, wherein n is 0.

### Claim 22 (depends on 1, 2, 3, 4, 5, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21)

The compound of any one of claims 1-5 and 9-21, wherein the compound of formula (I) has the structure of formula (Ie):
or pharmaceutically acceptable salts thereof,
wherein n is 0;
R7 is selected from H, F, Cl, —CH3, —CF3, and —Y′—(CH2)pM′; and
p is 0 or 1.

### Claim 23 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is thiadiazole.

### Claim 24 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is thiadiazole optionally substituted with —NR1R2 or —NR1C(O)R5, wherein R1, R2 and R5 in G are independently —H or —C1-4alkyl.

### Claim 25 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is triazole optionally substituted with —NR1R2, wherein Wand R2 in G are independently —H or —C1-4alkyl.

### Claim 26 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is triazole optionally substituted with a C1-4 alkyl.

### Claim 27 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is tetrazole optionally substituted with methyl.

### Claim 28 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is pyridine.

### Claim 29 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is thiazole.

### Claim 30 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is phenyl.

### Claim 31 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22)

The compound of any one of claims 1-22, wherein G is azetidine.

### Claim 32 (depends on 10, 11, 12, 13, 14, 15, 16, 17)

The compound of any one of claims 10-17, wherein:
Y is —S—;
n is 1 or 2;
G is —C(O)NR1R2; and
J, L and M are CR7.

### Claim 33 (depends on 10, 11, 12, 13, 14, 15, 16, 17)

The compound of any one of claims 10-17, wherein:
Y is —CH2—;
n is 0 to 2;
G is —C(O)NR1R2; and
J, L and M are CR7.

### Claim 34 (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)

The compound of any one of claims 1-33, wherein R7 is selected from the group consisting of —H, —OH, —C1-4alkyl, —O—C1-4alkyl, —S—C1-4alkyl, halogen, —CF3, and cyano.

### Claim 35 (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)

The compound of any one of claims 1-33, wherein R7 is selected from the group consisting of F, Cl, Me, —CF3, SMe, and —OMe.

### Claim 36 (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)

The compound of any one of claims 1-33, wherein R7 is H.

### Claim 37 (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)

The compound of any one of claims 1-33, wherein R7 is F.

### Claim 38 (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)

The compound of any one of claims 1-33, wherein R7 is —OMe.

### Claim 39 (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)

The compound of any one of claims 1-33, wherein R7 is —SMe.

### Claim 40 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 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)

The compound of any one of claims 1-10 and 13-38, wherein R is —CR5R6OC(O)C1-9alkyl or —CR5R6OC(O)OC1-9alkyl.

### Claim 41 (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)

The compound of any one of claims 1-33, wherein 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)NR2R1a; NR1CR5(═NR2); —NR1C(═NR2)NR1aR2a; aryl optionally substituted with 0-2 substituents selected from the group consisting of —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; heteroaryl optionally substituted with 0-2 substituents selected from the group consisting of —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5; and heterocyclyl optionally substituted with 0-2 substituents selected from the group consisting of −OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5.

### Claim 42 (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, 40, 41)

The compound of any one of claims 1-41, wherein R1 is H and R2 is H.

### Claim 43 (depends on 1)

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

### Claim 44 (depends on 1)

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

### Claim 45 (depends on 1)

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

### Claim 46 (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, 40, 41, 42, 43, 44, 45)

A pharmaceutical composition comprising a therapeutically effective amount of a compound of any one of claims 1-45 and a pharmaceutically acceptable excipient.

### Claim 47 (depends on 46)

The composition of claim 46, wherein the excipient is a monosaccharide or monosaccharide derivative.

### Claim 48 (depends on 47)

The compound of claims 47, wherein the monosaccharide or monosaccharide derivative is meglumine.

### Claim 49 (depends on 46, 47, 48)

The pharmaceutical composition of any one of claims 46 to 48, further comprising an additional medicament.

### Claim 50 (depends on 49)

The composition of claim 49, 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 51 (depends on 50)

The composition of claim 50, wherein the additional medicament is a β-lactam antibacterial agent.

### Claim 52 (depends on 51)

The composition of claim 51, 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, Cefinetazole, Loracarbef, Cefixime, Ceftriaxone, Cefcapene, Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefinenoxime, 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 53 (depends on 51)

The composition of claim 51, wherein the β-lactam antibacterial agent is selected from Ceftazidime, Biapenem, Doripenem, Ertapenem, Imipenem, Meropenem, or Panipenem.

### Claim 54 (depends on 51)

The composition of claim 51, wherein the β-lactam antibacterial agent is selected from Aztreonam, Tigemonam, BAL30072, SYN 2416, or Carumonam.

### Claim 55 (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, 40, 41, 42, 43, 44, 45)

A method of treating or preventing a bacterial infection, comprising administering to a subject in need thereof, a compound according any one of claims 1-45.

### Claim 56 (depends on 55)

The method of claim 55, further comprising administering to the subject an additional medicament.

### Claim 57 (depends on 56)

The method of claim 56, wherein the additional medicament is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an antiallergic agent.

### Claim 58 (depends on 56)

The method of claim 56, wherein the additional medicament is a β-lactam antibacterial agent.

### Claim 59 (depends on 58)

The method of claim 58, 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, Cefinetazole, Loracarbef, Cefixime, Ceftriaxone, Cefcapene, Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefinenoxime, 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 60 (depends on 58)

The method of claim 58, wherein the β-lactam antibacterial agent is selected from Ceftazidime, Biapenem, Doripenem, Ertapenem, Imipenem, Meropenem, or Panipenem.

### Claim 61 (depends on 58)

The method of claim 58, wherein the β-lactam antibacterial agent is selected from Aztreonam, Tigemonam, BAL30072, SYN 2416, or Carumonam.

### Claim 62 (depends on 55, 56, 57, 58, 59, 60, 61)

The method of any one of claims 55-61, wherein the subject is a mammal.

### Claim 63 (depends on 62)

The method of claim 62, wherein the mammal is a human.

### Claim 64 (depends on 55, 56, 57, 58, 59, 60, 61, 62, 63)

The method of any one of claims 55-63, 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 65 (depends on 55, 56, 57, 58, 59, 60, 61, 62, 63)

The method of any one of claims 55-63, wherein the infection comprises a bacteria selected from Pseudomonas aeruginosa, Pseudomonas fluorescens, Stenotrophomonas maltophilia, Escherichia coli, Citrobacter freundii, Salmonella typhimurium, Salmonella typhi, Salmonella paratyphi, Salmonella enteritidis, Shigella dysenteriae, Shigella flexneri, Shigella sonnei, Enterobacter cloacae, Enterobacter aerogenes, Klebsiella pneumoniae, Klebsiella oxytoca, Serratia marcescens, Acinetobacter calcoaceticus, Acinetobacter haemolyticus, Yersinia enterocolitica, Yersinia pestis, Yersinia pseudotuberculosis, Yersinia intermedia, Haemophilus influenzae, Haemophilus parainfluenzae, 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 66

A chemical complex, comprising a complex between a monosaccharide or monosaccharide derivative and a compound having the structure of formula (I):
or pharmaceutically acceptable salts thereof, wherein:
A is selected from the group consisting of C3-10 carbocyclyl, C6-10 aryl, 5-10 membered heteroaryl, and 5-10 membered heterocyclyl;
Xa is —C(ReRf)—, —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, —N(OR3)R2, 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, —N(OR3)R2, 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)R2, 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 —OH, optionally substituted —O—C1-6 alkyl, —NR1R2, and —N(OR3)R2, 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;
Y is selected from the group consisting of —S—, —S(O)—, —S(O)2—, —O—, —CH2— and —NR2—;
G is selected from the group consisting of —NR1R2, —N3, —C(O)NR1R2, —S(O)2NR1R2, —SR3, —OR3, —CH2NR1C(O)R5, —C(═NOR3)—X, C(═NOR3)—Z, —C(O)OR3, —S(O)2R3, —C(O)NR1(OR3), —NR1(OR3), —NR1C(O)R5, —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, —NR1CR5(═NR2), —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;
Re and Rf 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, —S(O)2R3, —R1—O—C(O)OR3, or Re and Rf together with the carbon to which they are attached form a C3-8 cycloalkyl or a 4-8 membered heterocyclyl;
R7 is present 1 to 5 times and each R7 is independently selected from the group consisitng 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, —OR3, —NR1R2, halogen, —C(O)NR1R2, and —NR1C(O)R5;
X is hydrogen or optionally substituted C1-9alkyl;
Z is selected from optionally substituted C3-8 cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
R is selected from the group consisting of —H, —C1-9alkyl, —CR5R6OC(O)C1-9alkyl, —CR5R6OC(O)OC1-9alkyl, and
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 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;
each R5, R6, R8 and R9 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;
each n is independently 0-3.

### Claim 67 (depends on 66)

The chemical complex of claim 66, wherein the monosaccharide or monosaccharide derivative is meglumine.