A PROCESS FOR THE PREPARATION OF CINACALCET AND ITS SALTS

Title:

A PROCESS FOR THE PREPARATION OF CINACALCET AND ITS SALTS

Document Type and Number:

WIPO Patent Application WO/2010/010359

Kind Code:

A3

Abstract:

A process for preparing (cinacalcet) α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l- naphthalenemethanamine (formula I): or a pharmaceutically acceptable salt thereof which comprises: a) reacting 1-acetonaphthone with an alkyl amine or a substituted or non-substituted aralkyl amine in presence of a suitable solvent to form imine compound (formula III), which on reduction using suitable reducing agent yields N-substituted naphthyl ethyl amine (formula IV). b) Optionally resolving the N-substituted naphthyl ethyl amine (formula (IV) into its corresponding (R) or (S) isomer (formula IVa and IVb). c) Further reacting the (R,S) or (R) or (S)-N-substituted naphthyl ethyl amine (formula IV, IVa, or IVb) with trifluoromethyl aryl alkyl compound (formula V) in presence of a base and in a suitable solvent to form an intermediate corresponding to (R5S), (R) or (S)-N-substituted- methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l-naphthalenemethanamine (N-substituted- cinacalcet) (formula VI, Via or VIb). d) Optionally resolving (R,S)-N-substituted cinacalcet (formula VI) into its corresponding (R) and (S) isomers (formula Via or VIb). e) Converting (R5S) or (R) or (S)-N-substituted-cinacalcet (formula VI, Via or VIb) to the corresponding (R5S) or (R) or (S)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l- naphthalenemethanamine (cinacalcet) (formula, I5 Ia or Ib)) by dealkylation or debenzylation, f) Optionally resolving (R,S)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l- naphthalenemethanamine (cincacalcet, formula I) into (R) and (S)-α-methyl-N-[3-[3- (trifluoromethyl)phenyl]propyl]-l-naphthalenemethanamine (formula Ia and Ib) using a suitable resolving agent.

More Like This:

JP5040460	Method for producing xylylenediamine
JPH083120	ACYLAMINO ACID-ALPHA-ARYLAMINE ADDUCT SALT AND METHOD FOR OPTICALLY REVOLVING ALPHA-ARYLAMINE
WO/2012/069004	SYNTHESIS AND APPLICATION OF INTERMEDIATE OF TAPENTADOL

Inventors:

RAO DHARMARAJ RAMACHANDRA (IN)
KANKAN RAJENDRA NARAYANRAO (IN)
BIRARI DILIP (IN)

Application Number:

PCT/GB2009/001835

Publication Date:

March 18, 2010

Filing Date:

July 23, 2009

Export Citation:

Click for automatic bibliography generation Help

Assignee:

CILPA LTD (IN)
RAO DHARMARAJ RAMACHANDRA (IN)
KANKAN RAJENDRA NARAYANRAO (IN)
BIRARI DILIP (IN)
CURTIS PHILIP ANTHONY (GB)

International Classes:

C07C211/27; C07C211/29

Domestic Patent References:

WO2008019690A1

2008-02-21

Foreign References:

US20070043243A1	2007-02-22
US5298660A	1994-03-29
US5981599A	1999-11-09

Other References:

HEINZ, T. ET AL.: "1-(1-Naphthyl)ethylamine and derivatives thereof as chiral modifiers in the enantioselective hydrogenation of ethyl pyruvate over Pt?alumina", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, 1995, pages 1421 - 1422, XP002559951
HUANG XUEFEI ET AL: "Absolute Configurational Assignments of Secondary Amines by CD-Sensitive Dimeric Zinc Porphyrin Host", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC. US, vol. 124, no. 35, 7 August 2002 (2002-08-07), pages 10320 - 10335, XP002396669, ISSN: 0002-7863