IP Library › Granted Patent US 8,685,418
Granted Patent B2
US 8,685,418 · App. 13/659,694 · Granted Apr 1, 2014

Cyclohexylamines

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Quick Facts
Patent No.
US 8,685,418
App. No.
13/659,694
Granted
Apr 1, 2014
Kind
B2
Abstract

The present application provides novel compounds and methods for preparing and using these compounds. These compounds are useful in treating pain, itch, overactive bladder and/or interstitial cystitis in patients by administering one or more of the compounds to a patient. The methods include administering a compound of formula (I) and a TRPV1 receptor activator. In one embodiment, the TRPV1 receptor activator is lidocaine.

Claims (55)

1. A compound selected from the group consisting of:

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-(Benzoyloxy)propyl]-N,N-diethylcyclohexanaminium chloride;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethoxybenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Chlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((3-Fluorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Fluoro-2-(trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2-(Trifluoromethyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2-nitrobenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3,5-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((4-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-(trifluoromethyl)benzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

(S)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((3-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]tetrahydro-2H-pyran-4-aminium iodide;

N-[2-((2,3-Dichlorobenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((Cyclohexanecarbonyl)oxy)propyl]-N,N-diethylcyclohexanaminium iodide;

N-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-Isopropylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((thiophene-3-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((1-methyl-1H-pyrrole-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((Benzo[b]thiophene-2-carbonyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((3-methylthiophene-2-carbonyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N,4-trimethylcyclohexanaminium iodide;

N,N,4-Trimethyl-N-[2-((2,4,6-trimethylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((2,6-Dimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4,6-Trimethylbenzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N,N-Dimethyl-N-[2-((4-methylbenzoyl)oxy)propyl]cyclohexanaminium iodide;

N-[2-((4-(tert-Butyl)benzoyl)oxy)ethyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2-Ethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

N-[2-((2,4-Dimethylbenzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium iodide;

(S)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

(R)-N-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-N,N-dimethylcyclohexanaminium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]pyrrolidin-1-ium bromide;

1-Cyclohexyl-1-[2-((2-isopropylbenzoyl)oxy)propyl]piperidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide;

1-[2-((4-(tert-Butyl)benzoyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide;

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpyrrolidin-1-ium bromide; and

1-[2-((3-Chlorobenzo[b]thiophene-2-carbonyl)oxy)propyl]-1-cyclohexylpiperidin-1-ium bromide.

Assignments (6)
CHANGE OF NAME Recorded Apr 6, 2023
From: ABS DEVELOPMENT 1, INC.
To: LIBERTAS BIO, INC.
Reel/Frame 063271/0055 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2022
From: ASANA BIOSCIENCES, LLC
To: ABS DEVELOPMENT 1, INC.
Reel/Frame 059968/0937 →
RELEASE OF SECURITY INTEREST Recorded Apr 28, 2017
From: DEUTSCHE BANK AG NEW YORK BRANCH
To: ENDO PHARMACEUTICALS, INC.; ENDO PHARMACEUTICALS SOLUTIONS, INC.; ASTORA WOMEN'S HEALTH HOLDINGS, LLC
Reel/Frame 042362/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2014
From: ENDO PHARMACEUTICALS INC.
To: ASANA BIOSCIENCES, LLC
Reel/Frame 033010/0256 →
GRANT OF SECURITY INTEREST IN PATENTS Recorded Mar 20, 2014
From: ENDO PHARMACEUTICALS SOLUTIONS, INC.; ENDO PHARMACEUTICALS, INC.; AMS RESEARCH CORPORATION; AMERICAN MEDICAL SYSTEMS, INC.; LASERSCOPE
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 032491/0440 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2013
From: THOMPSON, SCOTT KEVIN; SMITH, ROGER ASTBURY; GUPTA, SANDEEP; PRIESTLEY, TONY; LAPING, NICHOLAS JAMES; SAHA, ASHIS K; RUDRA, SONALI
To: ENDO PHARMACEUTICALS INC.
Reel/Frame 029914/0485 →