US 9,180,115 B2Granted

Cyclohexylamines

AssigneeAsana Biosciences, LLC

InventorsScott Kevin Thompson, Roger Astbury Smith, Sandeep Gupta, Tony Priestley, Nicholas James Laping, Ashis K. Saha, Sonali Rudra

Life of this patent

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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.

Claims18

Dependent claims

A method of treating pain in a patient, comprising administering to said patient a therapeutically effective amount of 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]l-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.

52 more elements

A method of treating pain in a patient, comprising administering to said patient a therapeutically effective amount of a compound selected from the group consisting of:

(i) 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;
and
(ii) a TRPV1 receptor activator.

54 more elements

A method of treating itch in a patient, comprising administering to said patient a therapeutically effective amount of 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.

52 more elements

A method of treating itch in a patient, comprising administering to said patient a therapeutically effective amount of a compound selected from the group consisting of:

(i) 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;
and
(ii) a TRPV1 receptor activator.

54 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/220,381Filed 20 Mar 2014 · continuation
Priority: 24 Oct 2011
Published: US 2014/0213552 A131 Jul 2014
Granted: 10 Nov 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification29 codes

A61K 31/40
Having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins: having five-membered rings with one nitrogen as the only ring hetero atom,…
A61K 31/215
Esters, e.g. nitroglycerine, selenocyanates: of carboxylic acids
A61K 31/235
Of carboxylic acids: having an aromatic ring attached to a carboxyl group
A61K 31/24
Having an aromatic ring attached to a carboxyl group: having an amino or nitro group

Family

Application61/550,489Us provisional application · filed 24 Oct 2011
Application61/683,519Us provisional application · filed 15 Aug 2012
Application13/659,694Parent of this continuation · filed 24 Oct 2012
US 2014/0213552 A1Pre-grant publication · published 31 Jul 2014
US 8,685,418 B2Parent of this continuation
US 2013/0101667 A1Published application
US 9,180,115 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A method of treating pain in a patient, comprising administering to said patient a therapeutically effective amount of 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]l-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.

52 more elements

Facts

Application

14/220,381Filed 20 Mar 2014 · continuation

Priority

24 Oct 2011

Published

US 2014/0213552 A131 Jul 2014

Granted

10 Nov 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification29 codes

A61K 31/40
Having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins: having five-membered rings with one nitrogen as the only ring hetero atom,…
A61K 31/215
Esters, e.g. nitroglycerine, selenocyanates: of carboxylic acids
A61K 31/235
Of carboxylic acids: having an aromatic ring attached to a carboxyl group
A61K 31/24
Having an aromatic ring attached to a carboxyl group: having an amino or nitro group

Family

Application61/550,489Us provisional application · filed 24 Oct 2011

Application61/683,519Us provisional application · filed 15 Aug 2012

Application13/659,694Parent of this continuation · filed 24 Oct 2012

US 2014/0213552 A1Pre-grant publication · published 31 Jul 2014

US 8,685,418 B2Parent of this continuation

US 2013/0101667 A1Published application

US 9,180,115 B2This patent

From the US filing history. Foreign family members aren’t listed.