# US 10,501,414 B2 · Indole analogs as 5-oxo-ETE receptor antagonists and method of use thereof

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

- Number: US 10,501,414 B2
- Document ID: US10501414B2
- Status: Granted
- Kind: B2
- Application number: 15/562,677
- Filed: 2016-03-29
- Published: 2018-03-29
- Granted: 2019-12-10
- Earliest claimed: 2015-03-31
- Assignees: The Royal Institution for the Advancement of Learning/Mcgill University; Florida Institute of Technology
- Applicants: The Royal Institution for the Advancement of Learning/Mcgill University; Florida Institute of Technology
- Inventors: William S. Powell; Joshua Rokach
- Web page: https://patentgrep.com/patent/US10501414B2

## CPC

- C07D 209/24: with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
- A61K 31/405: Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/06: Antipsoriatics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- C07C 69/34: Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C 69/675: of saturated hydroxy-carboxylic acids
- C07C 69/734: Ethers
- C07B 2200/07: Optical isomers
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

This invention relates to novel pharmaceutically-useful compounds, to methods for their preparation, and to pharmaceutical compositions and therapeutic methods for treating certain conditions.

## Claims

### Claim 1

A compound of formula
or a pharmaceutically acceptable salt or solvate thereof; wherein
R1 is H, a straight or branched alkyl, or lower cycloalkyl;
R2 is a lower straight or branched alkyl or lower cycloalkyl;
L is an alkylene chain of 4-7 members, an alkenylene chain of 4-7 members, a CH(OH)-alkylene chain wherein said alkylene chain in CH(OH)-alkylene chain has 4-6 members or an alkylene-O-alkylene chain wherein the two alkylene chains together in alkylene-O-alkylene chain have a total of 4-6 members;
Rb is H or F;
m is an integer of 0 to 5;
X is a substituent;
n is an integer of 0 to 4; and
Ra is a substituent.

### Claim 2 (depends on 1)

The compound as defined in claim 1, having the formula
or a pharmaceutically acceptable salt or solvate thereof; wherein R2, Ra, L, X, m and n are as defined in claim 1.

### Claim 3 (depends on 1)

The compound as defined in claim 1, having the formula
or a pharmaceutically acceptable salt or solvate thereof; wherein R2, Ra, L, X, m and n are as defined in claim 1.

### Claim 4 (depends on 1)

The compound as defined in claim 1, wherein R1 is a lower straight or branched alkyl; R2 is a lower straight or branched alkyl; L is an alkylene chain of 4-6 members or a CH(OH)-alkylene chain wherein said alkylene chain in CH(OH)-alkylene chain has 4-6 members; is an integer of 0 to 3 and X is halogen, C1-6alkyl, C1-6 alkoxy, —NR40R41, —C(O)NR40R41, —NR40COR41, carboxy, hydroxyl, —S(O)0-2R40, —C(O)R40, —C(O)OR40 or —SO2NR40R41; wherein R40 and R41 are each independently H, or C1-6alkyl; n is an integer of 0 to 3 and Ra is halogen, C1-6alkyl, C1-6 alkoxy, —NR40R41, —C(O)NR40R41, —NR40COR41, carboxy, hydroxyl, —S(O)0-2R40, —C(O)R40, —C(O)OR40 or —SO2NR40R41; wherein R40 and R41 are each independently H, or C1-6alkyl; and Rb is H.

### Claim 5 (depends on 1)

The compound as defined in claim 1, wherein R1 is a methyl, ethyl, n-propyl or isopropyl; R2 is a methyl, ethyl, n-propyl or isopropyl; L is —CH(OH)—(CH2)6—, —(CH2)7—, —(CH2)6—, —CH(OH)—(CH2)5—, —CH2—O—(CH2)3—, —(CH2)2—O—(CH2)2—, —(CH2)3—O—(CH2)—, —CH═CH—(CH2)4—, —CH2—CH═CH—(CH2)3—, —(CH2)2—CH═CH—(CH2)2—, or —(CH2)3—CH═CH—CH2—; m is an integer of 0 to 2 and X is F, Cl, C1-3alkyl, C1-3 alkoxy, or hydroxyl; n is an integer of 0 to 2 and Ra is F, Cl, C1-3alkyl, C1-3 alkoxy, or hydroxyl; and Rb is H.

### Claim 6 (depends on 1)

The compound as defined in claim 1, wherein R1 is a lower straight or branched alkyl.

### Claim 7 (depends on 1)

The compound as defined in claim 1, wherein R2 is a lower straight or branched alkyl.

### Claim 8 (depends on 1)

The compound as defined in claim 1, wherein

### Claim 9 (depends on 1)

The compound as defined in claim 1, wherein L is —CH(OH)—(CH2)6—, —(CH2)7—, —(CH2)6—, —CH(OH)—(CH2)5—, —(CH2)5—, or —(CH2)4—.

### Claim 10 (depends on 1)

The compound as defined in claim 1, wherein
is any one of X1-X14:

### Claim 11 (depends on 1)

The compound as defined in claim 1 having the formula
or a pharmaceutically acceptable salt or solvate thereof; wherein Ra, L, X and m are as defined in claim 1.

### Claim 12

A compound as defined in table 2 or table 3:
TABLE 2
Compounds
Formula
15
13
14
17
18
19
20
21
22
23
24
25
39
37
38
46
47
48
49
50
51
52
53
54
55
61
62
63
64
65
66
67
68
69
70
83
85
94
95
96
97
159
or
TABLE 3
Com-
pounds
Formula
46M
50M
54M
or
49M

### Claim 13 (depends on 1)

A pharmaceutical composition comprising the compound as defined in claim 1, or a pharmaceutically acceptable salt or solvate thereof, and one or more pharmaceutically acceptable carrier and/or excipient.

### Claim 14 (depends on 1)

A method for treating a disease or condition selected from asthma, allergic rhinitis, chronic obstructive pulmonary disorder, atopic dermatitis, psoriasis and acne, the method comprising administering a therapeutically effective amount of the compound as defined in claim 1, or a pharmaceutically acceptable salt or solvate thereof, to a subject in need thereof.