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

Families Citing this family (50)

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ES2176756T3 (es) * 1996-07-29 2002-12-01 Warner Lambert Co Proceso perfeccionado para la sintesis de los esteres protegidos del acido (s)-3,4-dihidroxibutirico.
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
JP3364482B2 (ja) * 1998-07-24 2003-01-08 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−ヒドロキシ−γ−ブチロラクトンの連続的な製造方法
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
ES2252088T3 (es) 1999-12-17 2006-05-16 Pfizer Science And Technology Ireland Limited Procedimiento de produccion a escala industrial de la hemisal de calcio de la atorvastatina trihidrato cristalina.
ES2258030T3 (es) * 1999-12-17 2006-08-16 Pfizer Science And Technology Ireland Limited Procedimiento para producir atorvastatina calcio cristalina.
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
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
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)
IL158790A0 (en) 2001-06-29 2004-05-12 Warner Lambert Co Crystalline forms of [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) (atorvastatin)
CA2451159A1 (en) * 2001-07-06 2003-01-16 Teva Pharmaceutical Industries Ltd. Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives via 6-cyano syn 3,5-dihydroxy hexanoic acid derivatives
CA2475586C (en) * 2002-02-25 2011-07-05 Biocon Limited Novel boronate esters
GB0211716D0 (en) 2002-05-22 2002-07-03 Phoenix Chemicals Ltd Process
ES2287549T3 (es) 2002-08-06 2007-12-16 Warner-Lambert Company Llc Procedimiento para preparar la fenilamida del acido 5-(4-fluorofenil)-1-(2-((2r,4r)-4-hidroxi-6-oxo-tetrahidropiran-2-il)etil)-2-isopropil-4-fenil-1h-pirrol-3-carboxilico.
JP2005539078A (ja) * 2002-09-18 2005-12-22 エス ケー コーポレイション 光学的に純粋な（Ｓ）−β−ヒドロキシ−γ−ブチロラクトンの連続製造方法
EP1625223A4 (en) * 2002-09-20 2009-11-11 Verenium Corp CHEMOENZYMATIC PROCEDURES FOR SYNTHESIS OF STATINES AND STATIN INTERCONNECTIONS
US6713639B1 (en) 2002-10-28 2004-03-30 Council Of Scientific And Industrial Research Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone
US20060205804A1 (en) * 2003-04-14 2006-09-14 Nelson James D Process for preparing 5-(4-fluorophenyl)-1-[2r,4r)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl) ethyl]-2-isopropyl-4-phenyl-1h-pyrrole-3-carboxylic acid phenylamide
ATE425132T1 (de) * 2003-04-22 2009-03-15 Biocon Ltd Neues verfahren zur stereoselektiven reduktion von beta-ketoestern
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
MXPA06003003A (es) * 2003-09-17 2006-06-23 Warner Lambert Co Formas cristalinas de acido [r-(r*, r*)]-2-(4- fluorofenil)-(, (-dihidroxi -5-(1- metiletil)-3 -fenil-4 -[(fenilamino) -carbonil]- 1h-pirrol -1-heptanoico.
WO2005068642A2 (en) 2003-10-01 2005-07-28 Board Of Trustees Operating Michigan State University Bacterial synthesis of 1,2,4-butanetriol enantiomers
AU2005232959A1 (en) * 2004-04-16 2005-10-27 Pfizer Products Inc. Process for forming amorphous atorvastatin calcium
EP3581564A1 (en) 2004-05-05 2019-12-18 Pfizer Products Inc. Diethylamine salt forms of [r-(r*,r*)]-2-(4-fluorophenyl)-beta, delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid
CA2573771C (en) 2004-07-20 2011-05-10 Warner-Lambert Company Llc Novel forms of [r-(r*,r*)]-2-(4-fluorophenyl)-.beta., .gamma.-dihydroxy-5-(1-menthylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid calcium salt (2:1)
AU2005298383A1 (en) 2004-10-28 2006-05-04 Warner-Lambert Company Llc Process for forming amorphous atorvastatin
CA2589537A1 (en) * 2004-12-02 2006-06-08 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
ES2304335T3 (es) 2005-11-21 2010-05-19 Warner-Lambert Company Llc Formas nuevas del acido (r-(r*,r*))-2-(4-fluorofenil)-b,b-dihidroxi-5-(1-metiletil)-3-fenil-4-((fenilamino)carbonil)1h-pirrol-1-heptanoico, de magnesio.
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
BRPI0714439A2 (pt) * 2006-07-19 2014-04-08 Univ Michigan State Processos para a preparação de d-1,2,4-butanotriol de trinitrato de 1,2,4-butanotriol, de ácido d-3,4-diidroxibutanóico, de ácido 3-desoxi-d-gliceropentanóico, de ácido (4s)-2-amino-4,5-diidroxipentanóico; d-1,2,4-butanotriol trinitrato de d-1,2,4-butanotriol, d-xilose desidrogenase, ácido d-xilônico, desidratase, ácido 3-desoxi-gliceropentanóico, ácido d-3-4-diidroxibutanóico, ácido (4s)-2-amino-4,5-diidroxipentanóico; ácidos nucléicos codificadores de uma d-xilose ou recombinantes, para biossíntese de 1,2,4-butanotriol, do ácido (4s)-2-amino-4,5-diidroxipentanóico, do ácido d-3-4-diidroxibutanóico, do ácido (4s)-2-amino-4,5-diidroxipentanóico; vetor knock-out de uma 3-desoxi-d-glicero-pentulossonato aldolase, entidade celular recombinante, célula recombinate, processo para investigação de polinucleotídeos candidatos codificadores de enzimas, anticorpo.
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
WO2010069593A1 (en) 2008-12-19 2010-06-24 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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JP2710688B2 (ja) * 1990-10-09 1998-02-10 鐘淵化学工業株式会社 ４―ブロモ―３―ヒドロキシ酪酸エステル誘導体の製造法
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
ES2176756T3 (es) * 1996-07-29 2002-12-01 Warner Lambert Co Proceso perfeccionado para la sintesis de los esteres protegidos del acido (s)-3,4-dihidroxibutirico.

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

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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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