WO2008058235A3 - Processes for the preparation of cinacalcet - Google Patents

Processes for the preparation of cinacalcet Download PDF

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Publication number
WO2008058235A3
WO2008058235A3 PCT/US2007/084073 US2007084073W WO2008058235A3 WO 2008058235 A3 WO2008058235 A3 WO 2008058235A3 US 2007084073 W US2007084073 W US 2007084073W WO 2008058235 A3 WO2008058235 A3 WO 2008058235A3
Authority
WO
WIPO (PCT)
Prior art keywords
processes
cinacalcet
preparation
hydrogen
formula
Prior art date
Application number
PCT/US2007/084073
Other languages
French (fr)
Other versions
WO2008058235A2 (en
Inventor
Pratap Reddy Padi
Surya Prabhakar Akundi
Sashi Kanth Suthrapu
Naveen Kumar Kolla
Vijaya Kumar Kotagiri
Uday Kumar Neelam
Sudhakar Reddy Baddam
Nagaraju Manne
Original Assignee
Reddys Lab Ltd Dr
Reddys Lab Inc Dr
Pratap Reddy Padi
Surya Prabhakar Akundi
Sashi Kanth Suthrapu
Naveen Kumar Kolla
Vijaya Kumar Kotagiri
Uday Kumar Neelam
Sudhakar Reddy Baddam
Nagaraju Manne
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Reddys Lab Ltd Dr, Reddys Lab Inc Dr, Pratap Reddy Padi, Surya Prabhakar Akundi, Sashi Kanth Suthrapu, Naveen Kumar Kolla, Vijaya Kumar Kotagiri, Uday Kumar Neelam, Sudhakar Reddy Baddam, Nagaraju Manne filed Critical Reddys Lab Ltd Dr
Publication of WO2008058235A2 publication Critical patent/WO2008058235A2/en
Publication of WO2008058235A3 publication Critical patent/WO2008058235A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Abstract

There are described several processes for making a free base of cinacalcet. One of the described processes goes through an intermediate of the formula (II) where R1 and R2 are both hydrogen, or R1 and R2, together, form a double bond.
PCT/US2007/084073 2006-11-08 2007-11-08 Processes for the preparation of cinacalcet WO2008058235A2 (en)

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
IN2061/CHE/2006 2006-11-08
IN2061CH2006 2006-11-08
US88524207P 2007-01-17 2007-01-17
US88523607P 2007-01-17 2007-01-17
US88523907P 2007-01-17 2007-01-17
US60/885,236 2007-01-17
US60/885,242 2007-01-17
US60/885,239 2007-01-17
US89021307P 2007-02-16 2007-02-16
US60/890,213 2007-02-16
IN524CH2007 2007-03-14
IN524/CHE/2007 2007-03-14
US96906207P 2007-08-30 2007-08-30
US60/969,062 2007-08-30

Publications (2)

Publication Number Publication Date
WO2008058235A2 WO2008058235A2 (en) 2008-05-15
WO2008058235A3 true WO2008058235A3 (en) 2008-10-02

Family

ID=39365372

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/084073 WO2008058235A2 (en) 2006-11-08 2007-11-08 Processes for the preparation of cinacalcet

Country Status (1)

Country Link
WO (1) WO2008058235A2 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR070754A1 (en) 2007-09-18 2010-05-05 Medichem Sa IMPROVED PROCESS TO PREPARE CINACALCET CHLORHYDRATE
KR20110028647A (en) * 2008-07-08 2011-03-21 인드-스위프트 래버러토리즈 리미티드 Process for preparing cinacalcet and pharmaceutically acceptable salts thereof
WO2010067204A1 (en) 2008-12-08 2010-06-17 Actavis Group Ptc Ehf Highly pure cinacalcet or a pharmaceutically acceptable salt thereof
CA2748595C (en) 2009-02-19 2017-03-14 Zach System S.P.A. Process for preparing cinacalcet hydrochloride
WO2010103531A2 (en) 2009-03-09 2010-09-16 Megafine Pharma (P) Ltd. A new method for the preparation of cinacalcet and new intermediates thereof
IT1394987B1 (en) * 2009-07-27 2012-08-07 Dipharma Francis Srl PROCEDURE FOR THE PREPARATION OF CINACALCET
IT1396623B1 (en) * 2009-11-26 2012-12-14 Dipharma Francis Srl PROCEDURE FOR THE PREPARATION OF CINACALCET AND ITS INTERMEDIATES
WO2012007954A1 (en) 2010-07-16 2012-01-19 Hetero Research Foundation Process for cinacalcet hydrochloride
CN101993379B (en) * 2010-10-22 2013-06-19 能特科技股份有限公司 Preparation method of cinacalcet hydrochloride
CN102718662A (en) * 2012-07-12 2012-10-10 杭州新博思生物医药有限公司 Method for preparing cinacalcet hydrochloride
FR2995307A1 (en) 2012-09-07 2014-03-14 Prod Chim Auxiliaires Et De Synthese PROCESS FOR THE PREPARATION OF CINACALCET AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
CN103193655B (en) * 2013-04-15 2015-06-24 山东新华制药股份有限公司 Method for preparing cinacalcet hydrochloride crystal form I
WO2015071831A1 (en) * 2013-11-18 2015-05-21 Piramal Enterprises Limited An improved process for minimising the formation of dehalogenated byproducts
CN104774134B (en) * 2014-01-09 2016-08-17 成都自豪药业有限公司 Cinacalcet hydrochloride and the synthetic method of midbody compound thereof
WO2017033134A1 (en) 2015-08-26 2017-03-02 Lupin Limited Enzymatic process for the for preparation of (r)-1-(1-naphthyl) ethylamine, an intermediate of cinacalcet hydrochloride
CN112321451B (en) * 2019-12-13 2022-08-23 福建海西新药创制有限公司 Method for preparing cinacalcet hydrochloride drug intermediate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6093830A (en) * 1998-11-09 2000-07-25 Council Of Scientific And Industrial Research Enantioselective resolution process for arylpropionic acid drugs from the racemic mixture
WO2004110976A2 (en) * 2003-06-13 2004-12-23 Avecia Pharmaceuticals Limited Process for the preparation of aromatic amines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6093830A (en) * 1998-11-09 2000-07-25 Council Of Scientific And Industrial Research Enantioselective resolution process for arylpropionic acid drugs from the racemic mixture
WO2004110976A2 (en) * 2003-06-13 2004-12-23 Avecia Pharmaceuticals Limited Process for the preparation of aromatic amines

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHANDRASEKHAR S. ET AL.: "Revisted mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzyl acetate and the improbability of the enolate of acetic anhydride", TETRAHEDRON LETTERS, vol. 47, 27 March 2006 (2006-03-27), pages 2249 - 2251, XP005304059 *
KITAMURA ET AL.: "Catalytic Leukart-Wallach-Type Reductive Animation of Ketones", J. ORG. CHEM., vol. 67, 2002, pages 8685 - 8687 *
WANG X. ET AL.: "Synthesis of Cinacalcet congeners", TETRAHEDRON LETTERS, vol. 45, 2004, pages 8355 - 8358, XP004593872 *
YAMAZAKI N. ET AL.: "Nucleophilic addition of methylithium to chiral oxime ethers: asymmetric preparation of 1-(aryl)ethylamines and application to a synthesis of calcimimetics (+)-NPS R-568 and its thio analogue", TETRAHEDRON LETTERS, vol. 42, 2001, pages 5029 - 5032, XP004250170 *

Also Published As

Publication number Publication date
WO2008058235A2 (en) 2008-05-15

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