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 (2)
EP (1) EP0915866B1 (2)
JP (1) JP2000515882A (2)
KR (1) KR100447370B1 (2)
CN (1) CN1093126C (2)
AT (1) ATE215078T1 (2)
AU (1) AU3515497A (2)
CO (1) CO4950542A1 (2)
DE (1) DE69711391T2 (2)
DK (1) DK0915866T3 (2)
ES (1) ES2176756T3 (2)
HU (1) HU226465B1 (2)
IL (1) IL127058A (2)
PT (1) PT915866E (2)
TR (1) TR199900191T2 (2)
WO (1) WO1998004543A1 (2)
ZA (1) ZA976705B (2)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
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AU3515497A (en) * 1996-07-29 1998-02-20 Warner-Lambert Company Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid
US6713290B2 (en) 1998-07-24 2004-03-30 Samsung Fine Chemicals Co., Ltd. Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone
KR100332703B1 (ko) * 1998-07-24 2002-08-27 삼성정밀화학 주식회사 광학활성을갖는(s)-3,4-에폭시부티르산염의제조방법
JP3614367B2 (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
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
ATE320415T1 (de) 1999-12-17 2006-04-15 Pfizer Science & Tech Ltd Verfahren zur herstellung von kristallin atorvastin kalcium
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
EP1734034A3 (en) 2001-01-09 2007-01-03 Warner-Lambert Company LLC Carboxylic acid salts of beta-alanine esters or -amides
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)
SK16002003A3 (sk) 2001-06-29 2004-12-01 Warner-Lambert Company Llc Kryštalické formy vápenatej soli (2:1) [R-(R*,R*)]-2-(4-fluóro- fenyl)-beta,delta-dihydroxy-5-(1-metyletyl)-3-fenyl-4- [(fenylamino)karbonyl]-1H-pyrrol-1-heptánovej kyseliny (atorvastatín)
HUP0401014A2 (hu) * 2001-07-06 2004-08-30 Teva Pharmaceutical Industries Ltd. Eljárás 7-amino-szin-3,5-dihidroxi-heptánsavszármazékok előállítására, 6-ciano-szin-3,5-dihidroxi-hexánsav származékokon keresztül
PT1478650E (pt) * 2002-02-25 2010-01-04 Biocon Ltd Novos ésteres boronato
GB0211716D0 (en) 2002-05-22 2002-07-03 Phoenix Chemicals Ltd Process
CA2494269A1 (en) * 2002-08-06 2004-02-19 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
DE60226518D1 (de) * 2002-09-18 2008-06-19 Sk Holdings Co Ltd Kontinuierliches verfahren zur herstellung von optisch reinem (s)-beta hydroxy- gamma-butyrolacton
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
JP2006523670A (ja) * 2003-04-14 2006-10-19 ワーナー−ランバート カンパニー リミティド ライアビリティー カンパニー ５−（４−フルオロフェニル）−１−［２−（（２ｒ，４ｒ）−４−ヒドロキシ−６−オキソ−テトラヒドロ−ピラン−２−イル）エチル］−２−イソプロピル−４−フェニル−１ｈ−ピロール−３−カルボン酸フェニルアミドの調製方法
SI1631533T1 (sl) * 2003-04-22 2009-08-31 Bicon Ltd Nov postopek za stereoselektivno redukcijo beta - ketoestrov
US7790197B2 (en) * 2003-06-09 2010-09-07 Warner-Lambert Company Llc Pharmaceutical compositions of atorvastatin
US7655692B2 (en) * 2003-06-12 2010-02-02 Pfizer Inc. Process for forming amorphous atorvastatin
US20040253305A1 (en) * 2003-06-12 2004-12-16 Luner Paul E. Pharmaceutical compositions of atorvastatin
US20050271717A1 (en) * 2003-06-12 2005-12-08 Alfred Berchielli Pharmaceutical compositions of atorvastatin
KR100781420B1 (ko) * 2003-09-17 2007-12-03 워너-램버트 캄파니 엘엘씨 [Ｒ-(Ｒ*,Ｒ*)]-2-(4-플루오로페닐)-β,δ-다이하이드록시-5-(1-메틸에틸)-3-페닐-4-[(페닐아미노)카보닐]-1Ｈ-피롤-1-헵탄산의 결정성 형태
WO2005068642A2 (en) 2003-10-01 2005-07-28 Board Of Trustees Operating Michigan State University Bacterial synthesis of 1,2,4-butanetriol enantiomers
WO2005100313A1 (en) * 2004-04-16 2005-10-27 Pfizer Products Inc. Process for forming amorphous atorvastatin calcium
US7875731B2 (en) 2004-05-05 2011-01-25 Pfizer Inc. Salt forms of [R-(R*,R*)]-2-(4-fluorophenyl)-β, δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)Carbonyl]-1H-pyrrole-1-heptanoic acid
CA2701710C (en) 2004-07-20 2013-08-27 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)
AU2005298383A1 (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
US7714141B2 (en) * 2005-05-31 2010-05-11 Kowa Co., Ltd. Processes for production of optically active PPAR-activating compounds and intermediates for production thereof
CA2547216A1 (en) 2005-09-21 2007-03-21 Renuka D. Reddy Process for annealing amorphous atorvastatin
ATE466840T1 (de) 2005-11-21 2010-05-15 Warner Lambert Co Neue formen von är-(r*,r*)ü-2-(4-fluorphenyl)-b,d-dihydroxy-5-( -methylethyl)-3-phenyl-4- ä(phenylamino)carbonylü-1h-pyrrol-1-heptansäure 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
KR20090039738A (ko) * 2006-07-19 2009-04-22 보드 오브 트러스티즈 오브 미시건 스테이트 유니버시티 Ｄ－１，２，４－부탄트리올의 미생물 합성
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
EP2726456A1 (en) 2011-07-01 2014-05-07 DSM Sinochem Pharmaceuticals Netherlands B.V. Micronized crystals of atorvastatin hemicalcium
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
CN117447350B (zh) * 2023-10-26 2026-02-13 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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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

Family Cites Families (3)

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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
AU3515497A (en) * 1996-07-29 1998-02-20 Warner-Lambert Company Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid

Patent Citations (1)

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

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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

Granted publication date: 20021023

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

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