CN1093126C - 合成被保护的(s)－3,4－二羟基丁酸酯的改进方法 - Google Patents

合成被保护的(s)－3,4－二羟基丁酸酯的改进方法 Download PDF

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Publication number
CN1093126C
CN1093126C CN97195996A CN97195996A CN1093126C CN 1093126 C CN1093126 C CN 1093126C CN 97195996 A CN97195996 A CN 97195996A CN 97195996 A CN97195996 A CN 97195996A CN 1093126 C CN1093126 C CN 1093126C
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China
Prior art keywords
acid
compound
formula
acid catalyst
mixture
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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.)
Expired - Fee Related
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CN97195996A
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English (en)
Chinese (zh)
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CN1223647A (zh
Inventor
T·E·扎克斯
D·E·布特勒
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Warner Lambert Co LLC
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Warner Lambert Co LLC
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Publication of CN1223647A publication Critical patent/CN1223647A/zh
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Anticipated expiration legal-status Critical
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)
CN97195996A 1996-07-29 1997-07-01 合成被保护的(s)－3,4－二羟基丁酸酯的改进方法 Expired - Fee Related CN1093126C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2236996P 1996-07-29 1996-07-29
US60/022,369 1996-07-29

Publications (2)

Publication Number Publication Date
CN1223647A CN1223647A (zh) 1999-07-21
CN1093126C true CN1093126C (zh) 2002-10-23

Family

ID=21809241

Family Applications (1)

Application Number Title Priority Date Filing Date
CN97195996A Expired - Fee Related CN1093126C (zh) 1996-07-29 1997-07-01 合成被保护的(s)－3,4－二羟基丁酸酯的改进方法

Country Status (17)

Country Link
US (1) US5998633A (cg-RX-API-DMAC10.html)
EP (1) EP0915866B1 (cg-RX-API-DMAC10.html)
JP (1) JP2000515882A (cg-RX-API-DMAC10.html)
KR (1) KR100447370B1 (cg-RX-API-DMAC10.html)
CN (1) CN1093126C (cg-RX-API-DMAC10.html)
AT (1) ATE215078T1 (cg-RX-API-DMAC10.html)
AU (1) AU3515497A (cg-RX-API-DMAC10.html)
CO (1) CO4950542A1 (cg-RX-API-DMAC10.html)
DE (1) DE69711391T2 (cg-RX-API-DMAC10.html)
DK (1) DK0915866T3 (cg-RX-API-DMAC10.html)
ES (1) ES2176756T3 (cg-RX-API-DMAC10.html)
HU (1) HU226465B1 (cg-RX-API-DMAC10.html)
IL (1) IL127058A (cg-RX-API-DMAC10.html)
PT (1) PT915866E (cg-RX-API-DMAC10.html)
TR (1) TR199900191T2 (cg-RX-API-DMAC10.html)
WO (1) WO1998004543A1 (cg-RX-API-DMAC10.html)
ZA (1) ZA976705B (cg-RX-API-DMAC10.html)

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DK0915866T3 (da) * 1996-07-29 2002-06-10 Warner Lambert Co Forbedret fremgangsmåde til syntese af beskyttende estere af (S)-3,4-dihydroxysmørsyre
KR100332703B1 (ko) * 1998-07-24 2002-08-27 삼성정밀화학 주식회사 광학활성을갖는(s)-3,4-에폭시부티르산염의제조방법
CN1160468C (zh) * 1998-07-24 2004-08-04 三星精密化学株式会社 制备光学纯(s)-3,4-二羟基丁酸衍生物的方法
US6713290B2 (en) 1998-07-24 2004-03-30 Samsung Fine Chemicals Co., Ltd. Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone
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
AU776613B2 (en) 1999-12-17 2004-09-16 Pfizer Science And Technology Ireland Limited A factory scale process for producing crystalline atorvastatin trihydrate hemi calcium salt
CA2391357C (en) * 1999-12-17 2009-01-06 Warner Lambert Research And Development 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
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
EP1728785A1 (en) 2001-01-09 2006-12-06 Warner-Lambert Company LLC 7-[(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-heptanoic acid ester 3,5-dioxo-acetal
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)
MXPA03010266A (es) * 2001-06-29 2004-03-10 Warner Lambert Co Formas cristalinas de la sal de calcio del acido [r-(r*, r*)]-2 -(4-fluorofenil)-¦, d-dihidroxi-5 -(1-metiletil)-3 -fenil-4- [(fenilamino) carbonil ]-1h- pirrol-1-heptanoico (2:1) (atorvastatin).
SK802004A3 (en) * 2001-07-06 2004-10-05 Teva Pharma Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives via 6-cyano syn 3,5-dihydroxy hexanoic acid derivatives
BR0215602A (pt) * 2002-02-25 2004-12-07 Biocon Ltd ésteres de boronato
GB0211716D0 (en) 2002-05-22 2002-07-03 Phoenix Chemicals Ltd Process
ATE368661T1 (de) * 2002-08-06 2007-08-15 Warner Lambert Co Verfahren zur herstellung von 5-(4-fluorphenyl)-1- 2-((2r,4r)-4-hydroxy-6-oxo etrahydropyran-2- yl)ethylö-2-isopropyl-4-phenyl-1h-pyrrol-3- carbonsäurephenylamid
CA2499655A1 (en) * 2002-09-18 2004-04-01 Sk Corporation Continuous process for the production of optically pure (s)-.beta.-hydroxy-.gamma.-butyrolactone
AU2003263031A1 (en) * 2002-09-20 2004-04-08 Diversa Corporation Chemoenzymatic methods for the synthesis of statins and stain intermediates
US6713639B1 (en) 2002-10-28 2004-03-30 Council Of Scientific And Industrial Research Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone
EP1615883A1 (en) * 2003-04-14 2006-01-18 Warner-Lambert Company 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
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
US20050271717A1 (en) * 2003-06-12 2005-12-08 Alfred Berchielli Pharmaceutical compositions of 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
CN1960972A (zh) * 2004-04-16 2007-05-09 辉瑞产品公司 用于形成无定形阿托伐它汀钙的方法
EP2540704B1 (en) 2004-05-05 2019-07-03 Pfizer Products Inc. Benethamine 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)
WO2006046109A1 (en) 2004-10-28 2006-05-04 Warner-Lambert Company Llc Process for forming amorphous atorvastatin
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
DK1957452T3 (da) * 2005-11-21 2010-07-26 Warner Lambert Co Nye former af [R-(R*,R*)]-2-(4-fluorphenyl)-B,B-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-heptansyre- 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
CN117447350A (zh) * 2023-10-26 2024-01-26 河南豫辰药业股份有限公司 一种阿托伐他汀m4有机废物综合再利用方法

Citations (1)

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US5292939A (en) * 1991-05-13 1994-03-08 Board Of Trustees Operating Michigan State University Process for the preparation of 3,4-dihydroxybutanoic acid and salts thereof

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JP3351563B2 (ja) * 1992-12-03 2002-11-25 鐘淵化学工業株式会社 ３−ヒドロキシ酪酸誘導体の製造法
DK0915866T3 (da) * 1996-07-29 2002-06-10 Warner Lambert Co Forbedret fremgangsmåde til syntese af beskyttende estere af (S)-3,4-dihydroxysmørsyre

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US5292939A (en) * 1991-05-13 1994-03-08 Board Of Trustees Operating Michigan State University Process for the preparation of 3,4-dihydroxybutanoic acid and salts thereof

Also Published As

Publication number Publication date
JP2000515882A (ja) 2000-11-28
ATE215078T1 (de) 2002-04-15
DK0915866T3 (da) 2002-06-10
ZA976705B (en) 1998-02-10
EP0915866B1 (en) 2002-03-27
IL127058A (en) 2001-07-24
WO1998004543A1 (en) 1998-02-05
CO4950542A1 (es) 2000-09-01
KR20000029648A (ko) 2000-05-25
CN1223647A (zh) 1999-07-21
HK1020728A1 (en) 2000-05-19
HUP9904348A2 (hu) 2000-04-28
PT915866E (pt) 2002-07-31
DE69711391D1 (de) 2002-05-02
US5998633A (en) 1999-12-07
HUP9904348A3 (en) 2004-03-01
DE69711391T2 (de) 2002-11-07
IL127058A0 (en) 1999-09-22
ES2176756T3 (es) 2002-12-01
KR100447370B1 (ko) 2004-09-08
AU3515497A (en) 1998-02-20
HU226465B1 (en) 2008-12-29
EP0915866A1 (en) 1999-05-19
TR199900191T2 (xx) 1999-04-21

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C14 Grant of patent or utility model
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EE01 Entry into force of recordation of patent licensing contract

Assignee: Pfizer Pharmaceuticals Limited

Assignor: Vonil Longbow (Warner & Lambert) Pfizer, Inc.

Contract fulfillment period: Contract performance period from January 10, 2006 to January 10, 2009

Contract record no.: Contract filing No. 061000010077

Denomination of invention: Improved methods for the synthesis of protected (S) -3, 4-, two butyric acid esters

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Free format text: LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2006.1.10 TO 2009.1.10

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