# US 8,541,586 B2 · Large substituent, non-phenolic opioids and methods 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 8,541,586 B2
- Document ID: US8541586B2
- Status: Granted
- Kind: B2
- Application number: 13/215,392
- Filed: 2011-08-23
- Published: 2011-12-15
- Granted: 2013-09-24
- Earliest claimed: 2005-07-21
- Assignees: Rensselaer Polytechnic Institute
- Applicants: Mark P. Wentland
- Inventors: Mark P. Wentland
- Web page: https://patentgrep.com/patent/US8541586B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/12: Antidiarrhoeals
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/14: Antitussive agents
- A61P 17/04: Antipruritics
- A61P 25/02: for peripheral neuropathies
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/30: for treating abuse or dependence
- A61P 25/36: Opioid-abuse
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 211/32: by oxygen atoms
- C07D 221/22: Bridged ring systems
- C07D 221/26: Benzomorphans
- C07D 221/28: Morphinans
- C07D 223/04: with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 241/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 489/00: Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: [IMAGE cpc-sch-C07D-0991.gif]
- C07D 489/08: Oxygen atom
- C07D 489/09: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D 489/12: the bridge containing only two carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

8-Substituted-2,6-methano-3-benzazocines of general structure are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications.

## Claims

### Claim 1

A compound of formula:
wherein R is —CH3, —CH2CH2CH(OH)C6H11, —CH2CH(CH2Ph)CONHCH2CO2H, —(CH—2)3CH(CH3)2 or —(CH2)3-2-thienyl;
wherein Q is
wherein
is an aryl or heteroaryl residue of one to three rings;
A is (CH2)n, wherein one or more CH2 may be replaced by —O—, cycloalkyl or CR1aR1b;
R1a and R1b are chosen independently from hydrogen, halogen, lower alkyl, lower alkoxy and lower alkylthio;
R10 is one or two residues chosen independently from hydrogen, hydroxyl, halogen, (C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkyl and halo(C1-C6)alkoxy and (C1-C6)alkylthio;
R11 is H or
is an aryl or heteroaryl residue of one to three rings;
A′ is (CH2)m wherein one or more CH2 may be replaced by —O—, cycloalkyl, —CR1aR1b, —C(═O)— or —NH—;
R12 is chosen from hydrogen and lower alkyl;
R15 is one or two residues chosen independently from hydrogen, hydroxyl, halogen, (C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkyl and halo(C1-C6)alkoxy and (C1-C6)alkylthio;
m is zero or an integer from 1 to 6; and
n is an integer from 1 to 6;
with the proviso that A is other than CH2.