Abstract: Process for the preparation of 2,2-difluoroethylamine of the formula (I) CHF2CH2NH2??(I) comprising the stages (i) and (ii): stage (i): reaction of 2,2-difluoro-1-haloethane of the general formula (II) CHF2—CH2Hal??(II), with a benzylamine compound of the formula (III) in the presence of an acid scavenger, in which, in formula (II), Hal is chlorine, bromine or iodine, and, in the formulae (III), R1 is hydrogen or C1-C12-alkyl, and R2 is hydrogen, halogen, C1-C12-alkyl or C1-C6-alkoxy; stage (ii): catalytic hydrogenation of the N-benzyl-2,2-difluoroethanamine compound obtained in the stage (i) to give 2,2-difluoroethylamine of the formula (I) or a salt thereof.
Type:
Grant
Filed:
November 9, 2011
Date of Patent:
May 28, 2013
Assignee:
Bayer Cropscience AG
Inventors:
Norbert Lui, Jens-Dietmar Heinrich, Christian Funke, Günter Schlegel, Thomas Norbert Müller
Abstract: The present invention relates to an improved process for the preparation of (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentanamine which is an intermediate for the preparation of the analgesic tapentadol.
Type:
Grant
Filed:
February 15, 2012
Date of Patent:
May 14, 2013
Assignee:
Janssen Pharmaceutica, NV
Inventors:
Walter Ferdinand Maria Filliers, Rudy Laurent Maria Broeckx
Abstract: The invention relates to solid tapentadol in non-crystalline form together with a surface stabiliser in the form of a stable intermediate. In the intermediate of the invention, tapentadol is preferably present in amorphous form or in the form of a solid solution. The invention further relates to methods of producing tapentadol in a solid, non-crystalline form and to pharmaceutical formulations containing solid, non-crystalline tapentadol.
Type:
Application
Filed:
May 5, 2011
Publication date:
May 9, 2013
Applicant:
RATIOPHARM GMBH
Inventors:
Jana Paetz, Daniela Stumm, Wolfgang Albrecht, Alexandre Mathieu
Abstract: The invention provides compounds of the formulas described herein and compositions thereof. The invention further provides methods of using the compounds and compositions. The compounds of the invention can provide high affinity binding to sigma-1 receptors in a mammal. The compounds can exhibit selectivity for the sigma-1 receptor over the sigma-2 receptor. The compounds and compositions of the invention can also be used to treat conditions that involve the sigma-1 receptor, such as addiction, cardiovascular conditions, and cancer, for example, cancer of the breast, lung, prostate, ovarian, colorectal, or the CNS.
Abstract: Provided herein is an improved and industrially advantageous optical resolution method for resolving (2R,3R)/(2S,3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol, and use thereof for the preparation of tapentadol or a pharmaceutically acceptable salt thereof. Provided further herein is an improved and industrially advantageous optical resolution method for resolving (2R,3R)/(2S,3S)-[3-(3-methoxyphenyl)-2-methylpentyl]-dimethylamine, and use thereof for the preparation of tapentadol or a pharmaceutically acceptable salt thereof. Disclosed also herein is an improved, commercially viable and industrially advantageous process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof in high yield and purity.
Abstract: Provided herein is a novel, commercially viable and industrially advantageous process for the preparation of 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol (Tapentadol), or a pharmaceutically acceptable salt thereof, and its intermediates, in high yield and purity. Provided also herein are novel solid state forms of tapentadol intermediates and processes for their preparation thereof. Provided further herein is a purification process for preparing highly pure tapentadol hydrochloride.
Abstract: Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
Type:
Grant
Filed:
August 3, 2011
Date of Patent:
March 5, 2013
Assignee:
Acucela, Inc.
Inventors:
Ian Leslie Scott, Vladimir Aleksandrovich Kuksa, Mark W. Orme, Thomas Little, Anna Gall, Jennifer Gage, Feng Hong
Abstract: This invention relates to clinically useful therapeutic regimens comprising the administration of (R)-6-(2-(ethyl(4-(2-(ethylamino)ethyl)benzyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol.
Type:
Application
Filed:
May 12, 2011
Publication date:
February 28, 2013
Inventors:
Louis O'Dea, C. Richard Lyttle, Jonathan Guerriero
Abstract: Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
Type:
Application
Filed:
September 14, 2012
Publication date:
January 31, 2013
Applicant:
Acucela Inc.
Inventors:
Ian Leslie Scott, Vladimir Aleksandrovich Kuksa, Mark W. Orme, Thomas Little, Anna Gall, Jennifer Gage, Feng Hong
Abstract: The present invention provides compositions and methods for the targeted delivery, release and/or formation of a drug compound at a target site(s) within the body of an individual, such as a diseased and/or inflamed tissue in the body of the individual. These compositions may comprise a halogenated phenol ring cleavably linked to a core structure of a drug compound. Due to the variety of substituents that may be utilized in forming the different types of linkages, numerous examples of drug compounds linked to a halogenated phenol ring are proposed. The present invention further provides compositions comprising halogenated phenol starting compounds that do not undergo cleavage during a dehalogenation reaction to form a drug compound in a targeted tissue when administered to an individual. Methods of administering these non-cleaving compounds are further provided.
Abstract: Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
Type:
Application
Filed:
September 14, 2012
Publication date:
January 17, 2013
Applicant:
Acucela Inc.
Inventors:
Ian Leslie Scott, Vladmir Aleksandrovich Kuksa, Mark W. Orme, Thomas Little, Anna Gall, Jennifer Gage, Feng Hong
Abstract: The invention relates to an improved process for preparing cinacalcet hydrochloride. The invention provides an efficient and economic process for preparing cinacalcet hydrochloride which is suitable for industrial implementation i.e., affords cinacalcet hydrochloride with high purity, and uses small volumes of acidifying agent and solvents.
Abstract: Gamma-amino-butyric acid derivatives that are GABAB receptor ligands, pharmaceutical compositions comprising such derivatives, and methods of using such derivatives and pharmaceutical compositions thereof for treating diseases are disclosed.
Type:
Grant
Filed:
April 16, 2010
Date of Patent:
January 1, 2013
Assignee:
XenoPort, Inc.
Inventors:
Feng Xu, Mark A. Gallop, Ge Peng, Thu Phan, Usha Dilip, David J. Wustrow
Abstract: A hitherto unknown crystalline form of (?)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride, pharmaceutical compositions containing the new crystalline form, methods of producing the new crystalline form, and a related method of use including treatment of, e.g., pain and/or urinary incontinence.
Type:
Application
Filed:
August 3, 2012
Publication date:
November 29, 2012
Applicant:
Gruenenthal GmbH
Inventors:
Andreas FISCHER, Helmut BUSCHMANN, Michael GRUSS, Dagmar LISCHKE
Abstract: The present invention discloses processes for the preparation of 3-[(1R,2R)-3-(dimethyl-amino)-1-ethyl-2-methyl-propyl]phenol (Tapentadol), salts thereof and related compounds of formula (A), including stereoisomers and pharmaceutically acceptable salts thereof, and to certain intermediates used in such process.
Abstract: Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
Type:
Grant
Filed:
June 30, 2008
Date of Patent:
October 30, 2012
Assignee:
Acucela Inc.
Inventors:
Ian Leslie Scott, Vladimir Aleksandrovich Kuksa, Mark W Orme, Thomas Little, Anna Gall, Jennifer Gage, Feng Hong
Abstract: Provided herein are novel solid state forms of tapentadol salts, process for their preparation, pharmaceutical compositions, and method of treating thereof. The tapentadol salts include an L-(?)-camphorsulfonate salt, a dibenzoyl-(L)-tartrate salt, a dibenzoyl-(D)-tartrate salt, a malate salt, a maleate salt, or a salicylate salt.
Abstract: Provided are methods of detecting the presence or amount of a dihydroxyvitamin D metabolite in a sample using mass spectrometry. The methods generally comprise associating an amine with a dihydroxyvitamin D metabolite in a sample, ionizing the adduct, and detecting the amount of the ion to determine the presence or amount of the vitamin D metabolite in the sample.
Abstract: A process for preparing N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)-phenyl]propan-1-amine of formula hydrochloride salt of formula (I) i.e. Cinacalcet.
Type:
Application
Filed:
September 8, 2010
Publication date:
September 20, 2012
Applicant:
ZACH SYSTEM S.P.A.
Inventors:
Nicola Catozzi, Livius Cotarca, Johnny Foletto, Massimiliano Forcato, Roberto Giovanetti, Giorgio Soriato, Massimo Verzini
Abstract: The invention relates to (among other things) oligomer-calcimimetic conjugates and related compounds. A conjugate of the invention, when administered by any of a number of administration routes, exhibits advantages over previously administered compounds.
Type:
Application
Filed:
March 28, 2012
Publication date:
September 20, 2012
Applicant:
Nektar Therapeutics
Inventors:
Jennifer Riggs-Sauthier, Lin Cheng, David Martin
Abstract: The present invention refers to a new process for the synthesis of tapentadol comprising the quantitative resolution of the racemic mixture (V) to obtain the stereoisomer of (S)-3-(dimethylamino)-2-methyl-1-(3-nitrophenyl)-propan-1-one (VII) according to the Scheme 2 below using the (2R,3R)—O,O?-dibenzoyltartaric chiral acid wherein said resolution is quantitative. The present invention also refers to some intermediate compounds of the new synthesis process of tapentadol.
Type:
Application
Filed:
November 30, 2010
Publication date:
September 13, 2012
Applicant:
Euticals S.P.A.
Inventors:
Giuseppe Motta, Domenico Vergani, Giorgio Bertolini
Abstract: The present invention relates to an improved process for the preparation of 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol monohydrochloride.
Abstract: The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6 , n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
Type:
Application
Filed:
March 5, 2012
Publication date:
September 6, 2012
Inventors:
Eric Marsault, Luc Ouellet, Hamid R. Hoveyda
Abstract: The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6, n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
Type:
Application
Filed:
March 5, 2012
Publication date:
September 6, 2012
Inventors:
Eric Marsault, Luc Ouellet, Hamid R. Hoveyda
Abstract: The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6, n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
Type:
Application
Filed:
March 5, 2012
Publication date:
September 6, 2012
Inventors:
Eric Marsault, Luc Ouellet, Hamid R. Hoveyda
Abstract: Disclosed are a novel, simple and low-cost method for preparing sitagliptin, as DPP-IV (dipeptidyl peptidase IV) inhibitor, which is useful in treating type 2 diabetes mellitus and key intermediates used in said preparation of sitagliptin.
Type:
Application
Filed:
October 19, 2010
Publication date:
August 23, 2012
Applicant:
HANMI HOLDINGS CO., LTD.
Inventors:
Nam Du Kim, Ji Yeon Chang, Dong Jun Kim, Hyun Seung Lee, Jae Hyuk Jung, Young Kil Chang, Gwan Sun Lee
Abstract: The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are alkoxyl derivative compounds and pharmaceutical compositions comprising these compounds. The subject compositions are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.
Type:
Application
Filed:
November 8, 2011
Publication date:
August 23, 2012
Applicant:
Acucela Inc.
Inventors:
Ian L. Scott, Vladimir A. Kuksa, Mark W. Orme, Thomas Little, Anna Gall, Feng Hong
Abstract: The present invention discloses methods of use of facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers, including, but not limited to, pharmaceutical uses of the polymers and oligomers as antimicrobial agents and as antidotes for hemorrhagic complications associated with heparin therapy. The present invention also discloses novel facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers, compositions of the novel polymers and oligomers, including pharmaceutical compositions, and methods of designing and synthesizing the facially amphiphilic polyaryl and polyarylalkynyl polymers and oligomers.
Type:
Grant
Filed:
January 21, 2005
Date of Patent:
July 17, 2012
Assignee:
The Trustees of the University of Pennsylvania
Inventors:
William F. DeGrado, Dahui Liu, Gregory N. Tew, Michael L. Klein
Abstract: The invention relates generally to thin-film adhesive materials suitable for various applications. In particular, the present invention provides pliable viscoelastic thin-films configured to form strong water-resistant adhesive bonds to various surface types.
Type:
Application
Filed:
July 14, 2010
Publication date:
July 12, 2012
Applicant:
KNC NER ACQUISITION SUB, INC.
Inventors:
Bruce P. Lee, Jediah White, Fangmin Xu, John L. Murphy, Laura Vollenweider
Abstract: The present invention provides a process for [18F]-fluorination of biomolecules containing a primary amino group such as proteins and peptides and in particular of peptides. The invention further provides reagents for this process, in particular 18F-labelled prosthetic groups for use in the preparation as well as non-labelled intermediates useful in the preparation of the [18F]-labelled prosthetic groups. [18F]-labelled compounds useful as radiopharmaceuticals, specifically for use in Positron Emission Tomography (PET) are also provided.
Abstract: The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6 , n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
Type:
Application
Filed:
March 5, 2012
Publication date:
June 28, 2012
Inventors:
Eric Marsault, Luc Ouellet, Hamid R. Hoveyda
Abstract: The invention relates to a neurochemical agent comprising at least one isotopically labeled carbon atom directly bonded to at least one deuterium atom, uses thereof for the manufacture of a composition for diagnosing and evaluating a condition or disease and kits comprising said agent. The invention further encompasses methods for diagnosing and evaluating a condition or disease in a subject utilizing a composition of the invention.
Abstract: The present invention relates to processes and intermediates useful in the preparation of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (lorcaserin), a serotonin (5-HT) receptor modulator that is useful in the treatment of, for example, central nervous system disorders, such as obesity.
Type:
Application
Filed:
June 17, 2010
Publication date:
June 7, 2012
Inventors:
John A. DeMattei, Marlon Carlos, Ryan O. Castro, Tsung-Hsun Chuang, Mark Allen Hadd, Xiao-Xiong Lu, Mark Macias, Stephen M. Shaw
Abstract: A number of FTY720-derived compounds with antitumor activity are described. These compounds include the compounds of formula I: wherein R1 is independently selected from the group consisting of hydrogen, methyl. methoxy, and hydroxyl; R2 is independently selected from the group consisting of hydrogen, methoxy, and hydroxyl; R3 is independently selected from the group consisting of alkyl and cyclo-alkyl; and n is independently selected from 0 to 6. The compounds have lower immunosuppressive side effects as a result of not being phosphorylated by sphingosine kinase 2.
Type:
Application
Filed:
November 29, 2011
Publication date:
May 31, 2012
Applicant:
The Ohio State University Research Foundation
Inventors:
Ching-Shih Chen, Samuel K. Kulp, Dasheng Wang, John C. Byrd, Natarajan Muthusamy
Abstract: The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are styrenyl derivative compounds, including but not limited to stilbene derivative compounds, and compositions comprising these compounds, that are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.
Type:
Application
Filed:
January 27, 2012
Publication date:
May 24, 2012
Applicant:
Acucela, Inc.
Inventors:
Ian Leslie Scott, Vladimir Aleksandrovich Kuksa, Anna Gall, Mark W. Orme, Jennifer Gage, Thomas L. Little, JR., Qin Jiang, Lana Michele Rossiter, Kevin F. McGee, JR., Ryo Kubota
Abstract: Compounds that are central nervous system drug candidates for the treatment of cognitive decline and, more particularly, Alzheimer's disease are provided. Methods of treating, inhibiting, and/or abatement of cognitive decline and/or Alzheimer's disease with a compound or pharmaceutically acceptable salt of the invention are also provided. Also provided are methods of preparing the compounds/compositions of the invention.
Abstract: Methods of preparing cinacalcet, cinacalcet derivatives, and salts thereof is disclosed herein. Also disclosed herein are polymorphs of cinacalcet, compositions of cinacalcet, and methods of treating a subject by administering cinacalcet, wherein cinacalcet is prepared by the disclosed methods.
Type:
Grant
Filed:
May 17, 2011
Date of Patent:
May 22, 2012
Assignee:
Amgen, Inc.
Inventors:
Oliver Thiel, Charles Bernard, Robert Larsen, Michael John Martinelli, Masooma Tamim Raza
Abstract: Compounds that are central nervous system drug candidates for the treatment of cognitive decline and, more particularly, Alzheimer's disease are provided. Methods of treating, inhibiting, and/or abatement of cognitive decline and/or Alzheimer's disease with a compound or pharmaceutically acceptable salt of the invention are also provided. Also provided are methods of preparing the compounds/compositions of the invention.
Abstract: The present invention relates to an improved process for the preparation of (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentanamine which is an intermediate for the preparation of the analgesic tapentadol.
Type:
Grant
Filed:
July 23, 2007
Date of Patent:
March 20, 2012
Assignee:
Janssen Pharmaceutica, NV
Inventors:
Walter Ferdinand Maria Filliers, Rudy Laurent Maria Broeckx
Abstract: The invention relates to pharmaceutical salts comprised of a pharmaceutical active substance and of at least one sugar substitute, to medicaments containing these salts, and to the use of these salts for producing medicaments.
Type:
Application
Filed:
November 14, 2011
Publication date:
March 8, 2012
Applicant:
GRUNENTHAL GMBH
Inventors:
JOHANNES BARTHOLOMÄUS, Heinrich Kugelmann
Abstract: The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6, n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
Type:
Grant
Filed:
November 19, 2008
Date of Patent:
March 6, 2012
Assignee:
Tranzyme Pharma Inc.
Inventors:
Eric Marsault, Luc Ouellet, Hamid R. Hoveyda
Abstract: There is provided a process for preparing a salt of the (R)- or (S)-isomer of 1-naphthylethylamine with mandelic acid or a derivative thereof, the process comprising reacting racemic 1-naphthylethylamine with mandelic acid or a derivative thereof to obtain the (R)- or (S)-isomer of 1-naphthylethylamine salt (III) with the acid. The salts also form an aspect of the present invention. There is also provided a salt of the (R)- or (S)-isomer of 1-naphthylethylamine with mandelic acid or a derivative thereof. There is also provided a process for preparing cinacalcet (I) or a salt thereof, the process comprising reacting an ester (II) with (R)-1-naphthylethylamine or a salt of (R)-1-naphthylethylamine and mandelic acid or a derivative thereof, to obtain cinacalcet, and optionally converting the cincalcet to a salt thereof.
Abstract: Provided are amine derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
Type:
Application
Filed:
October 21, 2011
Publication date:
February 16, 2012
Applicant:
Acucela Inc.
Inventors:
Ian L. Scott, Vladimir A. Kuksa, Mark W. Orme, Feng Hong, Thomas L. Little, JR., Ryo Kubota
Abstract: Provided are amine derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
Type:
Application
Filed:
October 21, 2011
Publication date:
February 16, 2012
Applicant:
Acucela Inc.
Inventors:
Ian L. Scott, Vladimir A. Kuksa, Mark W. Orme, Feng Hong, Thomas L. Little, JR., Ryo Kubota
Abstract: A reagent for organic synthesis with which a chemical reaction can be conducted in a liquid phase and unnecessary compound(s) can be easily separated at low cost from the liquid phase after completion of the reaction. The reagent for organic synthesis reversibly changes from a liquid-phase state to a solid-phase state with changes in solution composition and/or solution temperature, and is for use in organic synthesis reactions. This reagent for organic syntheses facilitates process development. With the reagent, research on and development of, e.g., medicines through, e.g., compound library synthesis, etc. can be accelerated. It can hence contribute to technical innovations in the biochemical industry and chemical industry.
Type:
Grant
Filed:
February 19, 2007
Date of Patent:
January 10, 2012
Assignee:
JITSUBO Co., Ltd.
Inventors:
Kazuhiro Chiba, Shokaku Kim, Yusuke Kono
Abstract: A method for the preparation of Cinacalcet is disclosed comprising treating (R)-1-naphthyl ethylamine with an aromatic aldehyde to form (1R)-1-(2-naphthyl)-N-(aryl methylene)ethanamine derivative of Formula (IV), which is further treated with 1-(3-halopropyl)-3-(trifluoromethyl)benzene of Formula (V) to obtain an iminium salt of Formula (VI), followed by hydrolysis to obtain Cinacalcet free base.
Abstract: Provided herein are impurities of cinacalcet, (R)-?-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-(5,6,7,8-tetrahydronaphthalene)methaneamine (tetrahydro cinacalcet impurity), (R)-?-Methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethaneamine-N-oxide (cinacalcet N-oxide impurity) and (R)-?-methyl-N-[3-[3-(trifluoromethyl)phenyl]methyl]-1-naphthalenemethaneamine (benzylamine impurity); and processes for preparation and isolation thereof. Provided further herein is a highly pure cinacalcet or a pharmaceutically acceptable salt thereof substantially free of impurities, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure cinacalcet or a pharmaceutically acceptable salt thereof substantially free of impurities.