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

Info

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
Authority
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

Links

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.

Landscapes

  • 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 (9)

* 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
CN115494170A (zh) * 2022-09-05 2022-12-20 湖南先施制药有限公司 一种雷美替胺中间体及其光学异构体的检测分离方法

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 (9)

* 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
CN115494170A (zh) * 2022-09-05 2022-12-20 湖南先施制药有限公司 一种雷美替胺中间体及其光学异构体的检测分离方法

Also Published As

Publication number Publication date
WO2008062468A3 (fr) 2008-07-24

Similar Documents

Publication Publication Date Title
WO2008062468A2 (fr) Procédé de préparation de derivés d'indéno[5,4-b] furane optiquement purs
KR100956260B1 (ko) 에스시탈로프람의 제조방법
JP2014159407A (ja) 高純度を有する２−［４−（３−または２−フルオロベンジルオキシ）ベンジルアミノ］プロパンアミドの製造方法
EP0737182A1 (fr) Procede de preparation d'un enantiomere de formoterol optiquement pur
EP1773793A2 (fr) Procede pour la preparation de pramipexole par chromatographie chirale
AU644081B2 (en) Novel 8-substituted-2-aminotetralines
WO2010055481A1 (fr) Procédé de préparation de rameltéon
JP3839049B2 (ja) メタ位置換のアリルアルキルアミン類ならびに治療および診断のためのその使用
CN101619040A (zh) 阿扑啡类化合物、其药物组合物及其用途
CN1296360C (zh) (1r,2r)－或(1s,2s)－1－(4'－取代－1',8'－萘酰亚胺基)－2－氨基环己烷及其制法和用途
KR100454712B1 (ko) 키랄고정상, 이들로 충진된 키랄칼럼 및 이들의 제조방법
KR100364255B1 (ko) 생리활성 라세미 일차 아미노 화합물의 광학분할을 위한ｌｃ용 크라운 에테르 키랄고정상 및 이들로 충진된키랄칼럼
CN113655145B (zh) 一种手性拆分丁苯那嗪对映异构体的方法
CN108727350A (zh) 一类哌啶烷基苯酞类化合物、其制备方法和用途
CN113820402A (zh) 一种米拉贝隆的杂质对照品的hplc分析方法
US20070123533A1 (en) New process for preparing an optically pure 2-morpholinol derivative
WO2015004686A2 (fr) Procédé de purification d'éfavirenz et de ses intermédiaires à l'aide de méthodes chromatographiques
KR100525288B1 (ko) 광학활성인ｎ,ｎ'-다이(치환벤조일)-2,3-다이아미노-1,4-부탄다이올을기저로한 키랄고정상 및 이들로 충진된 킬랄칼럼
JPH0597715A (ja) コンアルブミンが結合した光学異性体分離剤
JP2022543230A (ja) てんかん又はてんかん発作において使用するためのＫｖ７カリウムチャネル開口薬としてのアルコール誘導体
KR100949758B1 (ko) 항생제인 세파클러를 기저로 하는 키랄 고정상 및 이들로충진된 키랄컬럼
CN102050801B (zh) 一种芳烷哌嗪衍生物光学异构体的制备方法
JP2001213864A (ja) ラクタムの異性体混合物の異性体分離のための方法ならびにこうして得られた光学対掌体の使用
AU2002354525A1 (en) Method for the preparation of escitalopram
AU7179781A (en) Therapeutically useful tetralin derivatives

Legal Events

Date Code Title Description
DPE2 Request for preliminary examination filed before expiration of 19th month from priority date (pct application filed from 20040101)
NENP Non-entry into the national phase in:

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 997/MUMNP/2009

Country of ref document: IN

122 Ep: pct application non-entry in european phase

Ref document number: 07870511

Country of ref document: EP

Kind code of ref document: A2