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Ethanamine compounds and methods of using the same

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Ethanamine compounds and methods of using the same


(S)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine, pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising the same, uses of said compound or salt for therapy of depression and other conditions, and methods of treating depression and other conditions by administering said compound or salt.

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Inventors: Michael Balestra, Peter Bernstein, Glen E. Ernst, William Frietze, John P. McCauley, Lihong Shen, David Nugiel
USPTO Applicaton #: #20120277272 - Class: 514357 (USPTO) - 11/01/12 - Class 514 
Drug, Bio-affecting And Body Treating Compositions > Designated Organic Active Ingredient Containing (doai) >Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai >Hetero Ring Is Six-membered Consisting Of One Nitrogen And Five Carbon Atoms >Nitrogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding

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The Patent Description & Claims data below is from USPTO Patent Application 20120277272, Ethanamine compounds and methods of using the same.

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RELATED APPLICATIONS

This is a Continuation in Part of application Ser. No. 13/219,892 filed on Aug. 29, 2011 which is a Continuation of application Ser. No. 12/644,046 filed on Dec. 22, 2009, now U.S. Pat. No. 8,013,165, which claims the benefit of Provisional Application No. 61/140,673 filed on Dec. 24, 2008.

FIELD OF THE INVENTION

Disclosed herein is at least one ethanamine derivative, at least one pharmaceutical composition comprising at least one ethanamine derivative disclosed herein, and at least one method of using at least one ethanamine derivative disclosed herein for treating depression. The compounds may also have utility in the treatment of other diseases, including Parkinson\'s disease, pain states, such as neuropathic pain, as well as epilepsy and neurotrauma.

BACKGROUND OF THE INVENTION

Depression is a common mental disorder that occurs in persons of all genders, ages, and backgrounds, affecting about 121 million people worldwide. Symptoms of depression include, but are not limited to, depressed mood, loss of interest or pleasure, feelings of guilt or low self-worth, disturbed sleep or appetite, low energy, and poor concentration, or any combination thereof. These problems can become chronic or recurrent and lead to substantial impairments in an individual\'s ability to take care of his or her everyday responsibilities.

Depression is the leading cause of disability as measured by Years Lived with a Disability (YLDs) and the fourth leading contributor to the global burden of disease as measured by Disability Adjusted Life Years (DALYs; i.e., the sum of years of potential life lost due to premature mortality and the years of productive life lost due to disability) in 2000. By the year 2020, depression is projected to reach second place in the ranking of DALYs calculated for all ages, in both men and women. Today, depression is already the second cause of DALYs in the age category 15-44 years for both sexes combined. Whereas there are clearly a number of currently available treatments for depression, a significant proportion of patients are either incompletely treated (many residual symptoms remain) or do not respond to treatment at all. Thus, novel treatments for depression are needed. The present invention provides compounds, compositions, methods of preparing the same, and methods of treating depression. Such compounds would have additional utility in other disorders as well, including pain, Parkinson\'s disease, epilepsy and neurotrauma.

SUMMARY

OF THE INVENTION

The present invention provides in this continuation-in-part application compounds 1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof. (R)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof. (S)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof 2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof. (R)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof. (S)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof described throughout the application and in more detail in Examples 7 to 16.

DESCRIPTION OF EMBODIMENTS

The features and advantages of the invention may be more readily understood by those of ordinary skill in the art upon reading the following detailed description. An advantage of the present invention is the prevention of stilbazole formation. Stilbazole is an undesirable by-product. The effects of stilbazole on humans is not yet fully appreciated but a product without stilbazole would be preferable.

It is to be appreciated that certain features of the invention that are, for clarity reasons, described in the context of separate embodiments, may also be combined to form a single embodiment. Conversely, various features of the invention that are, for brevity reasons, described in the context of a single embodiment, may also be combined so as to form sub-combinations thereof.

Unless specifically stated otherwise herein, references made in the singular may also include the plural. For example, “a” and “an” may refer to either one, or one or more.

Embodiments identified herein as exemplary are intended to be illustrative and not limiting.

Unless otherwise indicated, any heteroatom with unsatisfied valences is assumed to have hydrogen atoms sufficient to satisfy the valences.

The definitions set forth herein take precedence over definitions set forth in any patent, patent application, and/or patent application publication incorporated herein by reference.

Definitions of terms used in describing the invention are set forth herein below. Unless otherwise indicated, the initial definition provided for a group or term applies each time such group or term is used individually. Throughout the specification, groups and substituents thereof may be chosen by one skilled in the field to provide stable moieties and compounds.

Unless specified otherwise herein, the nomenclature used herein generally follows the examples and rules stated in Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979.

The term “about” means±5% of the value it modifies. For example, “about” 100 means 95 to 105.

The term “halogen” refers to chlorine, bromine, fluorine, and iodine.

The term “pharmaceutically acceptable”, as employed herein, indicates the subject matter being identified as “pharmaceutically acceptable” is suitable and physiologically acceptable for administration to a patient/subject. For example, the term “pharmaceutically acceptable salt(s)” denotes suitable and physiologically acceptable salt(s).

The phrase “a compound of formula I, enantiomers thereof, pharmaceutically acceptable salts thereof, or mixtures thereof” or similar such phrases, refers to the free base of formula I or enantiomers thereof, pharmaceutically acceptable salts of formula I or enantiomers thereof, and/or mixtures of at least one free base of formula I or enantiomers thereof and at least one pharmaceutically acceptable salt of formula I or enantiomers thereof.

The term “therapeutically effective amount” refers to that amount of a compound sufficient to modulate one or more of the symptoms of the condition or disease being treated.

A selection of in vivo hydrolysable amide forming groups for hydroxy include alkanoyl, benzoyl, phenylacetyl and substituted benzoyl and phenylacetyl, alkoxycarbonyl (to give alkyl carbonate esters), dialkylcarbamoyl and N-(dialkylaminoethyl)-N-alkylcarbamoyl (to give carbamates), dialkylaminoacetyl and carboxyacetyl. Examples of substituents on benzoyl include morpholino and piperazino linked from a ring nitrogen atom via a methylene group to the 3- or 4-position of the benzoyl ring.

The present invention provides the compound 1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof.

The present invention provides the compound (R)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof.

The present invention provides the compound (S)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof.

The present invention provides the compound 1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides the compound (R)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides the compound (S)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides the compound 2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof.

The present invention provides the compound (R)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof.

The present invention provides the compound (S)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine or a pharmaceutically acceptable salt thereof.

The present invention provides the compound 2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides the compound (R)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides the compound (S)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is 1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is (R)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is (S)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is 1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is (R)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is (S)-1-(3-fluorophenyl)-2-methyl-2-(pyridin-2-yl)propan-1-amine fumarate.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is 2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is (R)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine.

The present invention provides a method of treating depression in a human which comprises administering to a person in need thereof a therapeutic effective amount of a compound or a pharmaceutically acceptable salt thereof, where the compound is (S)-2-methyl-1-phenyl-2-(pyridin-2-yl)propan-1-amine.



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stats Patent Info
Application #
US 20120277272 A1
Publish Date
11/01/2012
Document #
13431303
File Date
03/27/2012
USPTO Class
514357
Other USPTO Classes
546329
International Class
/
Drawings
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