# US 2019/0169148 A1 · Method for treating pain or associated condition or symptom

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- Number: US 2019/0169148 A1
- Document ID: US20190169148A1
- Status: Published application
- Kind: A1
- Application number: 16/274,107
- Filed: 2019-02-12
- Published: 2019-06-06
- Earliest claimed: 2014-04-21
- Assignees: Yissum Research Development Company of the Hebrew University of Jerusalem
- Applicants: Yissum Research Development Company of the Hebrew University of Jerusalem Ltd.
- Inventors: Ruth Gallily; Raphael Mechoulam; Aviva Breuer
- Web page: https://patentgrep.com/patent/US20190169148A1

## CPC

- C07D 295/15: to an acyclic saturated chain
- A61K 31/215: of carboxylic acids
- A61K 31/5375: 1,4-Oxazines, e.g. morpholine
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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

## Abstract

Compositions that include certain phenyl substituted cyclohexenyl compounds are administered to a subject in a method for treating obesity or an associated disease or disorder or in a method of reducing food consumption or body weight.

## Claims

### Claim 1

A method for treating pain or a condition or symptom associated therewith in a subject in need thereof, said method comprising administering to said subject a therapeutically effective amount of a compound of the general formula (I):
or a salt, enantiomer, diastereomer, or mixture thereof,
wherein
R1, R2 and R3 are each independently a (C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10) alkynyl, optionally substituted by at least one substituent each independently selected from the group consisting of hydroxy and halogen;
R4 is a (C1-C10)alkyl, (C2-C10)alkenyl or (C2-C10)alkynyl, substituted by at least one substituent of general formula (II):
X is selected from the group consisting of N, N+H, N+(C1-C10 alkyl), O+, S+, P, and P+H; and
R5 and R6 are each independently selected from the group consisting of H, (C1-C10) alkyl, (C2-C10)alkenyl, and (C2-C10)alkynyl, or both R4 and R6 together with X may form a (C3-C8)heterocyclic ring, wherein R5 and R6 each independently is optionally interrupted by at least one group each independently selected from the group consisting of —O—, —NH—, N+(C1-C10 alkyl), and —S—.

### Claim 2 (depends on 1)

The method of claim 1, wherein X is N or N+H.

### Claim 3 (depends on 2)

The method of claim 2, wherein X is N+H.

### Claim 4 (depends on 1)

The method of claim 1, wherein R5 and R6 form together with X a (C3-C8) heterocyclic ring.

### Claim 5 (depends on 4)

The method of claim 4, wherein said heterocyclic ring is further interrupted by at least one group each independently is selected from the group consisting of —O—, —NH—, and —S—.

### Claim 6 (depends on 1)

The method of claim 1, wherein R4 is a (C1-C5)alkyl substituted by a substituent of the general formula (III):
wherein m and n are each independently an integer selected from 0-5, wherein at least one of m or n is different than 0;
X is selected from the group consisting of N, N+H, N+(C1-C10 alkyl), O+, S+, P, and P+H;
Y is selected from the group consisting of —O—, —NH—, —S—, (C1-C6)alkylene, (C2-C6) alkenylene, and (C2-C6)alkynylene.

### Claim 7 (depends on 6)

The method of claim 6, wherein X is N or N+H.

### Claim 8 (depends on 6)

The method of claim 6, wherein Y is —O—.

### Claim 9 (depends on 1)

The method of claim 1, wherein R1 and R2 are each independently a (C1-C5) alkyl.

### Claim 10 (depends on 1)

The method of claim 1, wherein R3 is a (C4-C10)alkyl.

### Claim 11 (depends on 1)

The method of claim 1, wherein the substituents on positions 3 and 4 of said compound have a cis configuration.

### Claim 12 (depends on 11)

The method of claim 11, wherein the conformation of the substituents on positions 3 and 4 of said compound are equatorial: axial or axial: equatorial.

### Claim 13 (depends on 1)

The method of claim 1, wherein the substituents on positions 3 and 4 of said compound have a trans configuration.

### Claim 14 (depends on 13)

The method of claim 13, wherein the conformation of the substituents on positions 3 and 4 of said compound are equatorial: equatorial or axial: axial.

### Claim 15 (depends on 1)

The method of claim 1, wherein said compound is devoid of affinity to a CB receptor.

### Claim 16 (depends on 1)

The method of claim 1, for reducing food consumption in said subject.

### Claim 17 (depends on 1)

The method of claim 1, for reducing body weight in said subject.

### Claim 18 (depends on 1)

The method of claim 1, wherein said compound is of the formula:
or a salt, enantiomer, diastereomer, or mixture thereof,
wherein
R1 and R2 are each methyl;
R3 is pentyl; and
R4 is ethyl substituted by a substituent of the general formula (III):
wherein m and n are each 2; X is N; and Y is —O—.

### Claim 19 (depends on 18)

The method of claim 18, wherein said salt is the hydrochloride, hydrobromide, hydroiodide, nitrate, sulfate, bisulfate, phosphate, acid phosphate, isonicotinate, acetate, lactate, salicylate, citrate, tartrate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucaronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzensulfonate, p-toluenesulfonate, or pamoate salt of said compound.

### Claim 20 (depends on 1)

The method of claim 1, wherein said pain is chronic pain or acute pain.