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)
Other versions
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
Application granted granted Critical
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Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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)

* Cited by examiner, † Cited by third party
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DE69711391T2 (de) * 1996-07-29 2002-11-07 Warner-Lambert Co., Morris Plains Verbessertes verfahren zum herstellen von geschützten 3,4-dihydroxybuttersäure estern
US6713290B2 (en) 1998-07-24 2004-03-30 Samsung Fine Chemicals Co., Ltd. Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone
AU5067799A (en) * 1998-07-24 2000-02-14 Samsung Fine Chemicals Co., Ltd. Process for preparing optically pure (s)-3,4-dihydroxybutyric acid derivatives
KR100332703B1 (ko) * 1998-07-24 2002-08-27 삼성정밀화학 주식회사 광학활성을갖는(s)-3,4-에폭시부티르산염의제조방법
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
WO2001044180A1 (en) 1999-12-17 2001-06-21 Warner Lambert Research And Development Ireland Limited A factory scale process for producing crystalline atorvastatin trihydrate hemi calcium salt
DE60026737T2 (de) 1999-12-17 2006-09-21 Pfizer Science And Technology Ireland Ltd., Dun Laoghaire 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
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).
WO2003004456A1 (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
ES2332881T3 (es) * 2002-02-25 2010-02-15 Biocon Limited Nuevos esteres de boranato.
GB0211716D0 (en) 2002-05-22 2002-07-03 Phoenix Chemicals Ltd Process
WO2004014896A1 (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
US20060052617A1 (en) * 2002-09-18 2006-03-09 Sk Corporation Continuous process for the production of optically pure (s)-beta-hydroxy-y-butyrolactone
JP2006512086A (ja) * 2002-09-20 2006-04-13 ダイヴァーサ コーポレイション スタチンおよびスタチン中間体の合成のための酵素化学的方法
US6713639B1 (en) 2002-10-28 2004-03-30 Council Of Scientific And Industrial Research Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone
KR100780984B1 (ko) * 2003-04-14 2007-11-29 워너-램버트 캄파니 엘엘씨 5-(4-플루오로페닐)-1-[2-((2ｒ,4ｒ)-4-히드록시-6-옥소-테트라히드로-피란-2-일)에틸]-2-이소프로필-4-페닐-1ｈ-피롤-3-카르복실산 페닐아미드의 제조 방법
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
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
CA2539158A1 (en) * 2003-09-17 2005-03-24 Warner-Lambert Company Llc Crystalline forms of ['r-(r*,r*)]-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid
WO2005068642A2 (en) 2003-10-01 2005-07-28 Board Of Trustees Operating Michigan State University Bacterial synthesis of 1,2,4-butanetriol enantiomers
JP2007532622A (ja) * 2004-04-16 2007-11-15 ファイザー・プロダクツ・インク 非晶質アトルバスタチン・カルシウムの形成方法
CA2649054A1 (en) 2004-05-05 2005-11-10 Pfizer Products Inc. 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
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)
CN101048141A (zh) * 2004-10-28 2007-10-03 沃尼尔·朗伯有限责任公司 形成非晶形的阿托伐他汀的方法
JP2008521878A (ja) * 2004-12-02 2008-06-26 ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー 非晶質アトルバスタチンの医薬組成物及びその製造のための方法
WO2006129649A1 (ja) * 2005-05-31 2006-12-07 Kowa Co., Ltd. 光学活性ｐｐａｒ活性化化合物及びその製造中間体の製造法
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
US20110076730A1 (en) * 2006-07-19 2011-03-31 Board Of Trustees Of Michigan State University Microbial synthesis of d-1,2,4-butanetriol
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
SI2373609T1 (sl) 2008-12-19 2013-12-31 Krka, D.D., Novo Mesto Uporaba amfifilnih spojin za kontrolirano kristalizacijo statinov in intermediatov statinov
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
US20140335179A1 (en) 2011-07-01 2014-11-13 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
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)

* 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

Family Cites Families (3)

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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
DE69711391T2 (de) * 1996-07-29 2002-11-07 Warner-Lambert Co., Morris Plains Verbessertes verfahren zum herstellen von geschützten 3,4-dihydroxybuttersäure estern

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
AU3515497A (en) 1998-02-20
ES2176756T3 (es) 2002-12-01
ZA976705B (en) 1998-02-10
HU226465B1 (en) 2008-12-29
HUP9904348A2 (hu) 2000-04-28
CN1223647A (zh) 1999-07-21
DE69711391T2 (de) 2002-11-07
WO1998004543A1 (en) 1998-02-05
DK0915866T3 (da) 2002-06-10
PT915866E (pt) 2002-07-31
JP2000515882A (ja) 2000-11-28
IL127058A (en) 2001-07-24
CO4950542A1 (es) 2000-09-01
EP0915866A1 (en) 1999-05-19
IL127058A0 (en) 1999-09-22
TR199900191T2 (xx) 1999-04-21
EP0915866B1 (en) 2002-03-27
HUP9904348A3 (en) 2004-03-01
HK1020728A1 (en) 2000-05-19
US5998633A (en) 1999-12-07
DE69711391D1 (de) 2002-05-02
KR100447370B1 (ko) 2004-09-08
ATE215078T1 (de) 2002-04-15
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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Free format text: LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2006.1.10 TO 2009.1.10

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