# US 2016/0355462 A1 · Bicyclic analgesic compounds

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- Number: US 2016/0355462 A1
- Document ID: US20160355462A1
- Status: Published application
- Kind: A1
- Application number: 15/239,446
- Filed: 2016-08-17
- Published: 2016-12-08
- Earliest claimed: 2013-03-14
- Assignees: Kalyra Pharmaceuticals, Inc.
- Applicants: Kalyra Pharmaceuticals, Inc.
- Inventors: Kevin Duane Bunker
- Web page: https://patentgrep.com/patent/US20160355462A1

## CPC

- A61K 31/16: Amides, e.g. hydroxamic acids
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 31/13: Amines {(A61K31/04 takes precedence)}
- A61K 31/133: having hydroxy groups, e.g. sphingosine
- A61K 31/14: Quaternary ammonium compounds, e.g. edrophonium, choline (betaines A61K31/205)
- A61K 31/215: of carboxylic acids
- A61K 31/216: of acids having aromatic rings, e.g. benactizyne, clofibrate
- A61K 31/22: of acyclic acids, e.g. pravastatin
- A61K 31/221: with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
- A61K 31/235: having an aromatic ring attached to a carboxyl group
- A61K 31/24: having an amino or nitro group
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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]
- A61P 29/02: without antiinflammatory effect
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 211/62: Quaternary ammonium compounds
- C07C 217/52: having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C 233/06: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C 233/23: with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
- C07C 233/41: with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
- C07C 233/52: with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
- C07C 233/63: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C 235/74: of a saturated carbon skeleton
- C07C 2602/38: the bicyclo ring system containing five carbon atoms
- 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

## Abstract

Analgesic compounds for treatment of pain or fever, comprising a bicyclopentane moiety linked to an amine, combinations of the compounds with opioid analgesic drugs, and methods for treating pain or fever by administering the compounds.

## Claims

### Claim 1

A compound of Formula 1:
wherein
R1 is H, —CH3, CF3, or a substituted or unsubstituted (C2 to C5) lower alkyl;
R2 is H or C(═Y)R4;
R3 is H, F, D, hydroxy, (C1 to C10) alkoxy, (C1 to C30) substituted or unsubstituted alkyl, aryl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocycle, heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, or —(C═O)L;
R4 is CF3 or (C1 to C10) substituted or unsubstituted lower alkyl;
Y is S or O; and
—(C═O)L is a hydrolyzable prodrug ester leaving group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
L is a substituted or unsubstituted alkyl, cycloalkyl, aryl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocycle, heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, or any combination of such groups, all of which may be substituted or unsubstituted and which may range from C1 to C30 or otherwise include from 1 to 30 atoms, excluding hydrogen.

### Claim 3 (depends on 1)

The compound of claim 1, wherein
L is —CH3, CH2CH3, CH2CH2OH,

### Claim 4 (depends on 1)

The compound of claim 1, having one of the following structures:

### Claim 5 (depends on 1)

A method for treating an individual, comprising
identifying an individual in need of treatment to reduce or at least partially prevent pain or fever; and
administering to the individual an effective amount of a compound of claim 1.

### Claim 6 (depends on 1, 5)

The method of claim 5, further comprising administering an effective amount of an opioid analgesic in conjunction with administering the compound of claim 1 to the individual.

### Claim 7 (depends on 5)

The method of claim 5, wherein the administration is intravenous.

### Claim 8 (depends on 7)

The method of claim 7, wherein the pain is post-operative pain.