CA2724882A1 - Process for the synthesis of arformoterol - Google Patents

Process for the synthesis of arformoterol Download PDF

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Publication number
CA2724882A1
CA2724882A1 CA2724882A CA2724882A CA2724882A1 CA 2724882 A1 CA2724882 A1 CA 2724882A1 CA 2724882 A CA2724882 A CA 2724882A CA 2724882 A CA2724882 A CA 2724882A CA 2724882 A1 CA2724882 A1 CA 2724882A1
Authority
CA
Canada
Prior art keywords
compound
process according
formula
diastereomer
acid
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA2724882A
Other languages
English (en)
French (fr)
Inventor
Vaishali Vaman Haldavanekar
Mangesh Prabhu
Dharmaraj Ramachandra Rao
Rajendra Narayanrao Kankan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cipla Ltd
Original Assignee
Cipla Ltd
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 Cipla Ltd filed Critical Cipla Ltd
Publication of CA2724882A1 publication Critical patent/CA2724882A1/en
Abandoned legal-status Critical Current

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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
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C07C217/86—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • 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
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pulmonology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2724882A 2008-06-02 2009-06-02 Process for the synthesis of arformoterol Abandoned CA2724882A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN1172MU2008 2008-06-02
IN1172/MUM/2008 2008-06-02
PCT/GB2009/001373 WO2009147383A1 (en) 2008-06-02 2009-06-02 Process for the synthesis of arformoterol

Publications (1)

Publication Number Publication Date
CA2724882A1 true CA2724882A1 (en) 2009-12-10

Family

ID=40839516

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2724882A Abandoned CA2724882A1 (en) 2008-06-02 2009-06-02 Process for the synthesis of arformoterol

Country Status (10)

Country Link
US (2) US9029421B2 (enExample)
EP (1) EP2285770B1 (enExample)
JP (2) JP2011523658A (enExample)
KR (1) KR20110015449A (enExample)
AU (1) AU2009253877B2 (enExample)
CA (1) CA2724882A1 (enExample)
ES (1) ES2539947T3 (enExample)
NZ (1) NZ589497A (enExample)
WO (1) WO2009147383A1 (enExample)
ZA (1) ZA201008222B (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110015449A (ko) 2008-06-02 2011-02-15 시플라 리미티드 아르포르모테롤의 합성방법
US20110313199A1 (en) * 2008-12-26 2011-12-22 Actavis Group Ptc Ehf processes for preparing substantially pure arformoterol and its intermediates
EP2348013A1 (en) 2010-01-25 2011-07-27 Inke, S.A. Process for preparation of intermediates of arformoterol
MX355697B (es) 2010-04-12 2018-04-27 Supernus Pharmaceuticals Inc Métodos para producir sales de viloxazina y polimorfos novedosos de las mismas.
MX2014011576A (es) * 2012-04-11 2014-11-21 Cipla Ltd Composicion farmaceutica.
CN103664677A (zh) * 2012-09-05 2014-03-26 中山大学 一种(r,r)-福莫特罗酒石酸盐的不对称合成方法
CN106518690A (zh) * 2016-09-21 2017-03-22 北京万全德众医药生物技术有限公司 酒石酸阿福特罗重要中间体的一种制备方法
CN106565527A (zh) * 2016-11-02 2017-04-19 北京万全德众医药生物技术有限公司 一种酒石酸阿福特罗甲酰胺中间体的制备方法
CN107673957B (zh) * 2017-10-13 2020-10-23 河北工业大学 一种酸碱双功能离子液体催化低碳醛羟醛自缩合反应的方法
CN109627173A (zh) * 2019-01-19 2019-04-16 西南石油大学 一种氢转移选择性还原腈类制备仲胺的方法
CN112574055B (zh) * 2019-09-30 2024-07-09 天津天药药业股份有限公司 福莫特罗及其药用盐的制备方法及应用
CN113717060B (zh) * 2021-09-03 2024-03-15 成都新恒创药业有限公司 一种去甲肾上腺素及其重酒石酸盐的合成方法
CN115873909B (zh) * 2022-12-06 2023-08-11 天津法莫西生物医药科技有限公司 一种阿福特罗手性中间体的制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994974A (en) * 1972-02-05 1976-11-30 Yamanouchi Pharmaceutical Co., Ltd. α-Aminomethylbenzyl alcohol derivatives
JP3167705B2 (ja) * 1990-05-21 2001-05-21 広栄化学工業株式会社 ３―（ｎ―ベンジル―ｎ―アルコキシカルボニルアルキルアミノ）プロピオン酸エステルの製法
WO1995012572A1 (en) 1993-11-04 1995-05-11 Abbott Laboratories Cyclobutane derivatives as inhibitors of squalene synthetase and protein farnesyltransferase
SE9404080L (sv) 1993-12-28 1995-06-29 Ciba Geigy Ag Förfarande för framställning av en optiskt ren enantiomer av formoterol
EP0938467B1 (en) * 1996-11-11 2002-06-12 Sepracor, Inc. Process for the preparation of optically pure isomers of formoterol
US6040344A (en) * 1996-11-11 2000-03-21 Sepracor Inc. Formoterol process
US5965622A (en) * 1998-06-23 1999-10-12 Sepracor Inc. Desformoterol and process for its preparation
JP2000239237A (ja) * 1999-02-19 2000-09-05 Yamanouchi Pharmaceut Co Ltd 光学活性化合物の結晶及びその製法
JP2002255910A (ja) * 2001-02-27 2002-09-11 Nippon Kayaku Co Ltd １，１ービス（３−アミノー４ーヒドロキシフェニル）シクロアルカン類の製造方法
GB0118238D0 (en) * 2001-07-26 2001-09-19 Smithkline Beecham Plc Medicaments
GB2380996A (en) 2001-09-19 2003-04-23 Novartis Ag Hydroxy-nitrobenzene derivatives useful in the preparation of formoterol
CN1805926A (zh) * 2003-05-05 2006-07-19 兰贝克赛实验室有限公司 二苯基氮杂环丁酮衍生物的反式异构体的制备方法
GB0407908D0 (en) 2004-04-07 2004-05-12 Univ York Ionic liquids
JP4924034B2 (ja) 2004-05-24 2012-04-25 和光純薬工業株式会社 イオン性液体担持クラウン化合物
WO2008035380A2 (en) 2006-09-19 2008-03-27 Natco Pharma Limited An improved process for the preparation of high purity formoterol and its pharmaceutically acceptable salts
KR20110015449A (ko) 2008-06-02 2011-02-15 시플라 리미티드 아르포르모테롤의 합성방법

Also Published As

Publication number Publication date
KR20110015449A (ko) 2011-02-15
JP2011523658A (ja) 2011-08-18
EP2285770A1 (en) 2011-02-23
AU2009253877B2 (en) 2013-09-12
NZ589497A (en) 2012-09-28
US20110166237A1 (en) 2011-07-07
ES2539947T3 (es) 2015-07-07
EP2285770B1 (en) 2015-05-20
AU2009253877A1 (en) 2009-12-10
ZA201008222B (en) 2011-07-27
JP2015063529A (ja) 2015-04-09
US9029421B2 (en) 2015-05-12
WO2009147383A1 (en) 2009-12-10
US20150210629A1 (en) 2015-07-30

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Legal Events

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EEER Examination request

Effective date: 20140512

FZDE Discontinued

Effective date: 20170602