CO4950542A1 - Proceso mejorado para la sintesis de esteres protegidos de acido (s)-3, 4-dihidroxibutirico - Google Patents

Proceso mejorado para la sintesis de esteres protegidos de acido (s)-3, 4-dihidroxibutirico

Info

Publication number
CO4950542A1
CO4950542A1 CO97042973A CO97042973A CO4950542A1 CO 4950542 A1 CO4950542 A1 CO 4950542A1 CO 97042973 A CO97042973 A CO 97042973A CO 97042973 A CO97042973 A CO 97042973A CO 4950542 A1 CO4950542 A1 CO 4950542A1
Authority
CO
Colombia
Prior art keywords
compound
formula
acid
preparation
dihidroxibutirico
Prior art date
Application number
CO97042973A
Other languages
English (en)
Inventor
Donald Eugene Butler
Jacks Thomas Elliot
Original Assignee
Warner Lambert Co
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 Warner Lambert Co filed Critical Warner Lambert Co
Publication of CO4950542A1 publication Critical patent/CO4950542A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrane Compounds (AREA)

Abstract

Un proceso para la preparación y aislamiento de ésteres del ácido (S)-3-4-O-isopropiliden-3,4-dihidroxibutanóico, ortoésteres cíclicos del ácido (S)-3,4-dihidroxibutanóico y (S) 3-hidroxibutirolactona, caracterizado por comprender la preparación de un compuesto de Fórmula IUn proceso para la preparación de un compuesto de la Fórmula Idonde R y R1 son cada uno independientemente alquilo de 1 a 3 átomos de carbono; y R2 es alquilo de 1 a 8 átomos de carbono, caracterizado porque comprende:Paso (a), tratamiento de un sustrato de carbohidrato en un solvente con peróxido de hidrógeno en presencia de una base y posterior acidificación con un ácido para lograr una mezcla que comprende un compuesto de la Fórmula IV OH| IV HO-CH2 -CH-CH2 CO2 Hy ácido glicólico;Paso (b), eliminación del solvente para convertir el compuesto de la Fórmula IV en el compuesto de la Fórmula II En un segundo aspecto, el proceso comprende la preparación de un compuesto de Fórmula Iadonde R2 es alquilo de 1 a 8 átomos de carbono, mediante el tratamiento de un compuesto de Fórmula V OH| VHO-CH2 -CH-CH2 -CO2 R2 ...
CO97042973A 1996-07-29 1997-07-28 Proceso mejorado para la sintesis de esteres protegidos de acido (s)-3, 4-dihidroxibutirico CO4950542A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US2236996P 1996-07-29 1996-07-29

Publications (1)

Publication Number Publication Date
CO4950542A1 true CO4950542A1 (es) 2000-09-01

Family

ID=21809241

Family Applications (1)

Application Number Title Priority Date Filing Date
CO97042973A CO4950542A1 (es) 1996-07-29 1997-07-28 Proceso mejorado para la sintesis de esteres protegidos de acido (s)-3, 4-dihidroxibutirico

Country Status (18)

Country Link
US (1) US5998633A (es)
EP (1) EP0915866B1 (es)
JP (1) JP2000515882A (es)
KR (1) KR100447370B1 (es)
CN (1) CN1093126C (es)
AT (1) ATE215078T1 (es)
AU (1) AU3515497A (es)
CO (1) CO4950542A1 (es)
DE (1) DE69711391T2 (es)
DK (1) DK0915866T3 (es)
ES (1) ES2176756T3 (es)
HK (1) HK1020728A1 (es)
HU (1) HU226465B1 (es)
IL (1) IL127058A (es)
PT (1) PT915866E (es)
TR (1) TR199900191T2 (es)
WO (1) WO1998004543A1 (es)
ZA (1) ZA976705B (es)

Families Citing this family (49)

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KR100332703B1 (ko) * 1998-07-24 2002-08-27 삼성정밀화학 주식회사 광학활성을갖는(s)-3,4-에폭시부티르산염의제조방법
US6713290B2 (en) 1998-07-24 2004-03-30 Samsung Fine Chemicals Co., Ltd. Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone
JP3614366B2 (ja) 1998-07-24 2005-01-26 サムスン ファイン ケミカルズ カンパニー リミテッド 光学的に純粋な（ｓ）−３，４−ジヒドロキシ酪酸誘導体の製造方法
US6235930B1 (en) * 1999-03-31 2001-05-22 Board Of Trustees Operating Michigan State University Process for the preparation of 3,4-dihydroxybutanoic acid and derivatives thereof from substituted pentose sugars
HU227840B1 (en) * 1999-05-06 2012-05-02 Egis Gyogyszergyar Nyilvanosan M Kod Ruszvunytarsasag Intermediates of atorvastatin synthesis and process for producing them
EP1237865B1 (en) 1999-12-17 2005-11-16 Pfizer Science and Technology Ireland Limited A factory scale process for producing crystalline atorvastatin trihydrate hemi calcium salt
AU780247B2 (en) * 1999-12-17 2005-03-10 Pfizer Science And Technology Ireland Limited A process for producing crystalline atorvastatin calcium
JP4598917B2 (ja) * 2000-04-28 2010-12-15 ダイセル化学工業株式会社 ラクトンの製造方法
KR100645665B1 (ko) 2000-07-27 2006-11-13 에스케이 주식회사 (ｓ)-베타-하이드록시-감마-부티로락톤의 연속 제조방법
EP1724256A3 (en) 2001-01-09 2007-03-21 Warner-Lambert Company LLC Novel process for the synthesis of 5-(4-fluorphenyl)-1-2(2-((2r,4r)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl)-2-isopropyl-4-phenyl-1h-pyrrole-3-carboxylic acid phenylamide
US6476235B2 (en) * 2001-01-09 2002-11-05 Warner-Lambert Company Process for the synthesis of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide
WO2002057229A1 (en) * 2001-01-19 2002-07-25 Biocon India Limited FORM V CRYSTALLINE [R-(R*,R*)]-2-(4-FLUOROPHENYL)-ß,$G(D)-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(PHENYLAMINO)CARBONYL]-1H-PYRROLE-1- HEPTANOIC ACID HEMI CALCIUM SALT. (ATORVASTATIN)
CN1524073A (zh) * 2001-06-29 2004-08-25 ����-�����ع�˾ ′R-(R*,R*)-2-(4-氟苯基)-β,δ-二羟基-5-(1-甲基乙基)-3-苯基-4-(苯基氨基）羰基-1H-吡咯-1-庚酸钙盐（2∶1）（阿托伐他汀）
EP1406860A1 (en) * 2001-07-06 2004-04-14 Teva Pharmaceutical Industries Limited Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives via 6-cyano syn 3,5-dihydroxy hexanoic acid derivatives
KR100598079B1 (ko) * 2002-02-25 2006-07-07 바이오콘 리미티드 신규의 보로네이트 에스테르
GB0211716D0 (en) 2002-05-22 2002-07-03 Phoenix Chemicals Ltd Process
PL375415A1 (en) * 2002-08-06 2005-11-28 Warner-Lambert Company Llc Process for preparing 5-(4-fluorophenyl)-1-[2-((2r,4r)-4-hydroxy -6-oxo-tetrahydro-pyran-2-yl)ethyl]-2-isopropyl-4-phenyl-1h-pyrrole-3-carboxylic acid phenylamide
ATE394384T1 (de) * 2002-09-18 2008-05-15 Sk Holdings Co Ltd Kontinuierliches verfahren zur herstellung von optisch reinem (s)-beta hydroxy- gamma- butyrolacton
US7414119B2 (en) * 2002-09-20 2008-08-19 Verenium Corporation Aldolases, nucleic acids encoding them and methods for making and using them
US6713639B1 (en) 2002-10-28 2004-03-30 Council Of Scientific And Industrial Research Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone
WO2004089894A1 (en) * 2003-04-14 2004-10-21 Warner-Lambert Company Llc Process for preparing 5-(4-fluorophenyl)-1-[2-((2r,4r)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)ethyl]-2-isopropyl-4-phenyl-1h-pyrrole-3-carboxylic acid phenylamide
US7232920B2 (en) * 2003-04-22 2007-06-19 Biocon Process for stereoselective reduction of β-ketoesters
US7790197B2 (en) * 2003-06-09 2010-09-07 Warner-Lambert Company Llc Pharmaceutical compositions of atorvastatin
US20050271717A1 (en) 2003-06-12 2005-12-08 Alfred Berchielli Pharmaceutical compositions of atorvastatin
US20040253305A1 (en) * 2003-06-12 2004-12-16 Luner Paul E. Pharmaceutical compositions of atorvastatin
US7655692B2 (en) * 2003-06-12 2010-02-02 Pfizer Inc. Process for forming amorphous atorvastatin
CN1852894A (zh) * 2003-09-17 2006-10-25 沃尼尔·朗伯有限责任公司 [R－(R*, R*)]－2－(4－氟苯基) －β,δ－二羟基－5－(1－甲基乙基) －3－苯基－4－[(苯基氨基)羰基] －1 H－吡咯－1－庚酸的结晶形式
WO2005068642A2 (en) 2003-10-01 2005-07-28 Board Of Trustees Operating Michigan State University Bacterial synthesis of 1,2,4-butanetriol enantiomers
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WO2005105738A2 (en) 2004-05-05 2005-11-10 Pfizer Products Inc. Salt forms of atorvastatin
CA2754932C (en) 2004-07-20 2014-04-01 Warner-Lambert Company Llc Novel forms of [r-(r*,r*)]-2-(4-fluorophenyl)-.beta.,.delta.-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid calcium salt (2:1)
MX2007004722A (es) * 2004-10-28 2007-06-15 Warner Lambert Co Procedimiento para formar atorvastatina amorfa.
US20090088465A1 (en) * 2004-12-02 2009-04-02 Stephen Craig Dyar Pharmaceutical Compositions of Amorphous Atorvastatin and Process for Preparing Same
DE602006013815D1 (de) * 2005-05-31 2010-06-02 Kowa Co Verfahren zur herstellung von optisch aktiven ppar-aktivierenden verbindungen und zwischenprodukte für die herstellung
CA2547216A1 (en) * 2005-09-21 2007-03-21 Renuka D. Reddy Process for annealing amorphous atorvastatin
WO2007057755A1 (en) 2005-11-21 2007-05-24 Warner-Lambert Company Llc Novel forms of [r-(r*,r*)]-2-(4-fluorophenyl)-b,b-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-hept anoic acid magnesium
US20110165641A1 (en) * 2006-03-31 2011-07-07 The Board Of Trustees Of Michigan State University Synthesis of 1,2,4-Butanetriol Enantiomers from Carbohydrates
CN101512004A (zh) * 2006-07-19 2009-08-19 密歇根州州立大学托管委员会 D-1,2,4-丁三醇的微生物合成
KR100850558B1 (ko) 2008-01-02 2008-08-06 조동옥 아토르바스타틴의 효율적인 제조방법
JP2009256316A (ja) 2008-03-28 2009-11-05 Daicel Chem Ind Ltd β−ヒドロキシ−γ−ブチロラクトンの製造方法
CN101337906B (zh) * 2008-08-15 2012-06-27 河南豫辰精细化工有限公司 一种4-甲基-3-氧代-n-苯基戊酰胺的制备方法
EP2373609B1 (en) 2008-12-19 2013-10-16 KRKA, D.D., Novo Mesto Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates
EP2327682A1 (en) 2009-10-29 2011-06-01 KRKA, D.D., Novo Mesto Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates
MX2013015272A (es) 2011-07-01 2014-04-14 Dsm Sinochem Pharm Nl Bv Cristales micronizados.
CN106397241A (zh) * 2016-08-23 2017-02-15 杨锋 一种4‑甲基‑3‑氧代‑n‑苯基戊酰胺的绿色环保后处理方法
CN106588689A (zh) * 2016-12-15 2017-04-26 河南豫辰药业股份有限公司 一种从结晶母液废液中回收阿托伐他汀中间体m4的方法
CN112939901B (zh) * 2021-02-09 2023-05-09 中国科学院福建物质结构研究所 一种α-羟基-γ-丁内酯的制备方法
CN114195670B (zh) * 2021-12-31 2024-03-15 河南豫辰药业股份有限公司 一种阿托伐他汀母核m4的精制方法

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US5998633A (en) * 1996-07-29 1999-12-07 Warner-Lambert Company Process for the synthesis of protected esters of (S)-3,4-dihydroxybutyric acid

Also Published As

Publication number Publication date
ES2176756T3 (es) 2002-12-01
EP0915866A1 (en) 1999-05-19
US5998633A (en) 1999-12-07
HK1020728A1 (en) 2000-05-19
DE69711391T2 (de) 2002-11-07
CN1223647A (zh) 1999-07-21
DK0915866T3 (da) 2002-06-10
KR20000029648A (ko) 2000-05-25
CN1093126C (zh) 2002-10-23
WO1998004543A1 (en) 1998-02-05
ATE215078T1 (de) 2002-04-15
EP0915866B1 (en) 2002-03-27
ZA976705B (en) 1998-02-10
HUP9904348A2 (hu) 2000-04-28
TR199900191T2 (xx) 1999-04-21
IL127058A (en) 2001-07-24
IL127058A0 (en) 1999-09-22
AU3515497A (en) 1998-02-20
DE69711391D1 (de) 2002-05-02
JP2000515882A (ja) 2000-11-28
KR100447370B1 (ko) 2004-09-08
HUP9904348A3 (en) 2004-03-01
HU226465B1 (en) 2008-12-29
PT915866E (pt) 2002-07-31

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