WO2012032546A3 - Process for the preparation of salmeterol and its intermediates - Google Patents

Process for the preparation of salmeterol and its intermediates Download PDF

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Publication number
WO2012032546A3
WO2012032546A3 PCT/IN2011/000615 IN2011000615W WO2012032546A3 WO 2012032546 A3 WO2012032546 A3 WO 2012032546A3 IN 2011000615 W IN2011000615 W IN 2011000615W WO 2012032546 A3 WO2012032546 A3 WO 2012032546A3
Authority
WO
WIPO (PCT)
Prior art keywords
benzyloxy
benzoate
methyl
acetyl
preparation
Prior art date
Application number
PCT/IN2011/000615
Other languages
French (fr)
Other versions
WO2012032546A2 (en
Inventor
Shriprakash Dhar Dwivedi
Niraj Shyamlal Shah
Original Assignee
Cadila Healthcare Limited
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 Cadila Healthcare Limited filed Critical Cadila Healthcare Limited
Publication of WO2012032546A2 publication Critical patent/WO2012032546A2/en
Publication of WO2012032546A3 publication Critical patent/WO2012032546A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention discloses a process for the preparation of methyl 2-(benzyloxy)- 5-(2-bromoacetyl)benzoate Formula (V) comprising: (d) benzylating methyl-5-acetyl-2-hydroxybenzoate (VIII) with benzyl chloride in the presence of a base and a catalyst in a suitable polar solvent to obtain 5-acetyl-2- benzyloxy benzoate; Formula (VII) (e) brominating methyl 5-acetyl-2-(benzyloxy)benzoate with a suitable brominating agent in one or more suitable solvents in the presence of an acid catalyst to obtain methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate
PCT/IN2011/000615 2010-09-08 2011-09-08 Process for the preparation of salmeterol and its intermediates WO2012032546A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2482MU2010 2010-09-08
IN2482/MUM/2010 2010-09-08

Publications (2)

Publication Number Publication Date
WO2012032546A2 WO2012032546A2 (en) 2012-03-15
WO2012032546A3 true WO2012032546A3 (en) 2012-06-28

Family

ID=45464038

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2011/000615 WO2012032546A2 (en) 2010-09-08 2011-09-08 Process for the preparation of salmeterol and its intermediates

Country Status (1)

Country Link
WO (1) WO2012032546A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103864629A (en) * 2012-12-13 2014-06-18 天津金耀集团有限公司 Refining method of Salmeterol xinafoate
WO2016142582A1 (en) 2015-03-11 2016-09-15 Fermion Oy Process for the preparation of crystalline salmeterol and its xinafoate salt
CN106478432A (en) * 2016-08-29 2017-03-08 鲁南制药集团股份有限公司 A kind of preparation method of former times how sour salmaterol
AU2019232437A1 (en) 2018-03-07 2020-10-08 Bayer Aktiengesellschaft Identification and use of ERK5 inhibitors
CN109232884A (en) * 2018-07-07 2019-01-18 盐城师范学院 A kind of interface preparation method of two dimension organic framework materials

Citations (10)

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Publication number Priority date Publication date Assignee Title
EP0882707A1 (en) * 1996-01-10 1998-12-09 Asahi Kasei Kogyo Kabushiki Kaisha Novel tricyclic compounds and drug compositions containing the same
WO1999064035A1 (en) * 1998-06-08 1999-12-16 Advanced Medicine, Inc. β2-ADRENERGIC RECEPTOR AGONISTS
WO2001042193A1 (en) * 1999-12-08 2001-06-14 Theravance, Inc. β2-ADRENERGIC RECEPTOR AGONISTS
WO2003099764A1 (en) * 2002-05-28 2003-12-04 Theravance, Inc. ALKOXY ARYL β2 ADRENERGIC RECEPTOR AGONISTS
WO2004074246A2 (en) * 2003-02-14 2004-09-02 Theravance Inc. Biphenyl derivatives having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
WO2005051946A2 (en) * 2003-11-21 2005-06-09 Theravance, Inc. Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
WO2007045857A1 (en) * 2005-10-17 2007-04-26 Generics (Uk) Limited Novel process
EP1073429B1 (en) * 1998-04-24 2007-07-11 Glaxo Group Limited Aerosol formulations of salmeterol xinafoate
WO2007146869A1 (en) * 2006-06-09 2007-12-21 Parion Sciences, Inc. Phenyl substituted pyrazinoylguanidine sodium channel blockers possessing beta agonist activity
JP2012001454A (en) * 2010-06-15 2012-01-05 Ohara Yakuhin Kogyo Kk Simple method for producing salmeterol

Family Cites Families (8)

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ES345365A1 (en) 1967-09-22 1969-02-01 Allen & Hanburys Ltd A procedure for the preparation of new derivatives of 1-phenyl-2-aminoetanol. (Machine-translation by Google Translate, not legally binding)
ZW6584A1 (en) 1983-04-18 1985-04-17 Glaxo Group Ltd Phenethanolamine derivatives
ES2065269B1 (en) 1993-05-11 1995-10-01 S A L V A T Lab Sa 6- (4- (FENILBUTOXI) HEXILAMINOMETIL-4-HIDROXI-A1, A3-BENCENODIMETANOL. PROCEDURE FOR THE OBTAINING OF THE SAME AND NEW INTERMEDIATES USED IN ITS PREPARATION.
GB9313650D0 (en) 1993-07-01 1993-08-18 Glaxo Group Ltd Method and apparatus for the formation of particles
US6680345B2 (en) 2001-09-14 2004-01-20 Boehringer Ingelheim Pharma Kg Salicylic acid salts of salmeterol
US6756508B2 (en) 2002-03-04 2004-06-29 Boehringer Ingelheim Pharma Gmbh & Co. Kg Cinnamic acid salts, processes for their preparation, and their use as medicaments
US6835857B2 (en) 2002-03-05 2004-12-28 Boehringer Ingelheim Pharma Gmbh & Co. Kg Process for the manufacture of 4-(6-bromohexyloxy)-butylbenzene
ES2288114B1 (en) 2006-04-26 2008-12-01 Quimica Sintetica S.A. NEW SYNTHESIS PROCEDURE OF (6- (4-PHENYLBUTOXY) HEXIL) N-SUBSTITUTED AMINES AND ITS USE IN THE SYNTHESIS OF SALMETEROL XINAFOATO.

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0882707A1 (en) * 1996-01-10 1998-12-09 Asahi Kasei Kogyo Kabushiki Kaisha Novel tricyclic compounds and drug compositions containing the same
EP1073429B1 (en) * 1998-04-24 2007-07-11 Glaxo Group Limited Aerosol formulations of salmeterol xinafoate
WO1999064035A1 (en) * 1998-06-08 1999-12-16 Advanced Medicine, Inc. β2-ADRENERGIC RECEPTOR AGONISTS
WO2001042193A1 (en) * 1999-12-08 2001-06-14 Theravance, Inc. β2-ADRENERGIC RECEPTOR AGONISTS
WO2003099764A1 (en) * 2002-05-28 2003-12-04 Theravance, Inc. ALKOXY ARYL β2 ADRENERGIC RECEPTOR AGONISTS
WO2004074246A2 (en) * 2003-02-14 2004-09-02 Theravance Inc. Biphenyl derivatives having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
WO2005051946A2 (en) * 2003-11-21 2005-06-09 Theravance, Inc. Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
WO2007045857A1 (en) * 2005-10-17 2007-04-26 Generics (Uk) Limited Novel process
WO2007146869A1 (en) * 2006-06-09 2007-12-21 Parion Sciences, Inc. Phenyl substituted pyrazinoylguanidine sodium channel blockers possessing beta agonist activity
JP2012001454A (en) * 2010-06-15 2012-01-05 Ohara Yakuhin Kogyo Kk Simple method for producing salmeterol

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DE MEGLIO P ET AL: "Sintesi e studio farmacologico di derivati dell'orciprenalina e del salbutamolo [Synthesis and pharmacological study of orciprenaline and salbutamol derivatives]", FARMACO, EDIZIONE SCIENTIFICA, SOCIETA CHIMICA ITALIANA, PAVIA, IT, vol. 32, no. 3, 1 January 1980 (1980-01-01), pages 203 - 230, XP009108160, ISSN: 0430-0920 *
HETT R ET AL: "Enantioselective synthesis of salmeterol via asymmetric borane reduction", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 35, no. 50, 12 December 1994 (1994-12-12), pages 9375 - 9378, XP026655540, ISSN: 0040-4039, [retrieved on 19941212], DOI: 10.1016/S0040-4039(00)78546-7 *
LIU J ET AL: "A convenient synthesis of (R)-salmeterol via Rh-catalyzed asymmetric transfer hydrogenation", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 19, no. 15, 8 August 2008 (2008-08-08), pages 1824 - 1828, XP023902368, ISSN: 0957-4166, [retrieved on 20080809], DOI: 10.1016/J.TETASY.2008.07.021 *
TADEUSZ F MOLINSKI ET AL: "Improves synthesis of 13C, 2H3 and 2H3-salmeterol by Cs2CO3-mediated monalkylation of a primary amine", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 45, 1 January 2002 (2002-01-01), pages 755 - 762, XP002420119, ISSN: 0362-4803, DOI: 10.1002/JLCR.595 *

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