WO2008062468A2 - Procédé de préparation de derivés d'indéno[5,4-b] furane optiquement purs - Google Patents

Procédé de préparation de derivés d'indéno[5,4-b] furane optiquement purs Download PDF

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Publication number
WO2008062468A2
WO2008062468A2 PCT/IN2007/000491 IN2007000491W WO2008062468A2 WO 2008062468 A2 WO2008062468 A2 WO 2008062468A2 IN 2007000491 W IN2007000491 W IN 2007000491W WO 2008062468 A2 WO2008062468 A2 WO 2008062468A2
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WO
WIPO (PCT)
Prior art keywords
chromatography
critical
chiral
ramelteon
pure
Prior art date
Application number
PCT/IN2007/000491
Other languages
English (en)
Other versions
WO2008062468A3 (fr
Inventor
Sanjog Ramdharane
Tejas Chandrakant Shah
Jayesh Mohanlal Pandya
Manoj Kumar Singh
Virendra Kumar Agrawal
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 WO2008062468A2 publication Critical patent/WO2008062468A2/fr
Publication of WO2008062468A3 publication Critical patent/WO2008062468A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems

Definitions

  • the compound of formula (2) may be prepared in racemic form by reduction of intermediate (3) by techniques known in the art, which may be subsequently be converted to racemic Ramelteon (1) by condensation with propionyl chloride (4).
  • the desired pure isomer of (1) is subsequently obtained by either optical resolution or preparative chromatography using chiral and/or achiral stationary phases for batch process, super-critical or sub-critical chromatography and/or continuous process chromatography.

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

Abstract

La présente invention porte sur un procédé nouveau et efficace pour la préparation de dérivés d'indéno[5,4-b]furane chiralement actifs, qui comprennent la séparation d'intermédiaires chiralement purs et/ou de Rameltéon racémique dans sa forme isomère pure et exempte d'autres impuretés, par la séparation d'isomères à l'aide de phases stationnaires chirales et/ou achirales pour un procédé par lots, une chromatographie supercritique ou sub-critique et/ou une chromatographie à traitement continu.
PCT/IN2007/000491 2006-10-26 2007-10-15 Procédé de préparation de derivés d'indéno[5,4-b] furane optiquement purs WO2008062468A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1772MU2006 2006-10-26
IN1772/MUM/2006 2006-10-26

Publications (2)

Publication Number Publication Date
WO2008062468A2 true WO2008062468A2 (fr) 2008-05-29
WO2008062468A3 WO2008062468A3 (fr) 2008-07-24

Family

ID=39361951

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000491 WO2008062468A2 (fr) 2006-10-26 2007-10-15 Procédé de préparation de derivés d'indéno[5,4-b] furane optiquement purs

Country Status (1)

Country Link
WO (1) WO2008062468A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008150953A1 (fr) * 2007-05-30 2008-12-11 Dr. Reddy's Laboratories Ltd. Procédé de préparation de rameltéon et substances apparentées
WO2009093133A1 (fr) * 2008-01-25 2009-07-30 Medichem, S.A. Procédé pour déterminer la pureté énantiomérique de dérivés de l'indane
WO2010041271A2 (fr) 2008-09-16 2010-04-15 Usv Limited Préparation de (s)-n-[2-(1,6,7,8-tétrahydro-2h-indéno[5,4-b]furan-8-yl)éthyl] propionamide et nouveaux intermédiaires de ce composé
WO2010055481A1 (fr) * 2008-11-14 2010-05-20 Watson Pharma Private Limited Procédé de préparation de rameltéon
CN102099348A (zh) * 2008-07-14 2011-06-15 力奇制药公司 作为用于制备拉米替隆的中间体的6，7-二氢-1h-吲哚并[5，4-b]呋喃-8(2h)-酮的合成方法
US8084630B2 (en) 2007-05-31 2011-12-27 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates
WO2012035303A2 (fr) 2010-09-17 2012-03-22 Cipla Limited Et Al Nouveau procédé de synthèse du ramelteon et intermédiaires clés pour la synthèse du ramelteon
CN104327021A (zh) * 2014-11-24 2015-02-04 苏州乔纳森新材料科技有限公司 一种雷美替胺中间体的拆分方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6034239A (en) * 1996-03-08 2000-03-07 Takeda Chemical Industries, Ltd. Tricyclic compounds, their production and use

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6034239A (en) * 1996-03-08 2000-03-07 Takeda Chemical Industries, Ltd. Tricyclic compounds, their production and use

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
RIVARA ET AL: "Reassessing the melatonin pharmacophore-Enantiomeric resolution, pharmacological activity, structure analysis, and molecular modeling of a constrained chiral melatonin analogue" BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER SCIENCE LTD, GB, vol. 14, no. 10, 15 May 2006 (2006-05-15), pages 3383-3391, XP005364989 ISSN: 0968-0896 *
T. YAMANO ET AL: "Approach to the stereoselective synthesis of melatonin receptor agonist Ramelteon via asymmetric hydrogenation" TETRAHEDRON ASYMMETRY, vol. 17, no. 2, 23 January 2006 (2006-01-23), pages 184-190, XP002481301 NLELSEVIER, AMSTERDAM. *
UCHIKAWA O ET AL: "Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists" JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 45, 1 January 2002 (2002-01-01), pages 4222-4239, XP002990691 ISSN: 0022-2623 cited in the application *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008150953A1 (fr) * 2007-05-30 2008-12-11 Dr. Reddy's Laboratories Ltd. Procédé de préparation de rameltéon et substances apparentées
US8084630B2 (en) 2007-05-31 2011-12-27 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates
WO2009093133A1 (fr) * 2008-01-25 2009-07-30 Medichem, S.A. Procédé pour déterminer la pureté énantiomérique de dérivés de l'indane
CN102099348A (zh) * 2008-07-14 2011-06-15 力奇制药公司 作为用于制备拉米替隆的中间体的6，7-二氢-1h-吲哚并[5，4-b]呋喃-8(2h)-酮的合成方法
WO2010041271A2 (fr) 2008-09-16 2010-04-15 Usv Limited Préparation de (s)-n-[2-(1,6,7,8-tétrahydro-2h-indéno[5,4-b]furan-8-yl)éthyl] propionamide et nouveaux intermédiaires de ce composé
WO2010055481A1 (fr) * 2008-11-14 2010-05-20 Watson Pharma Private Limited Procédé de préparation de rameltéon
WO2012035303A2 (fr) 2010-09-17 2012-03-22 Cipla Limited Et Al Nouveau procédé de synthèse du ramelteon et intermédiaires clés pour la synthèse du ramelteon
CN104327021A (zh) * 2014-11-24 2015-02-04 苏州乔纳森新材料科技有限公司 一种雷美替胺中间体的拆分方法

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WO2008062468A3 (fr) 2008-07-24

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