AU3515497A - Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid - Google Patents
Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acidInfo
- Publication number
- AU3515497A AU3515497A AU35154/97A AU3515497A AU3515497A AU 3515497 A AU3515497 A AU 3515497A AU 35154/97 A AU35154/97 A AU 35154/97A AU 3515497 A AU3515497 A AU 3515497A AU 3515497 A AU3515497 A AU 3515497A
- Authority
- AU
- Australia
- Prior art keywords
- improved process
- synthesis
- pct
- dihydroxybutyric acid
- protected esters
- Prior art date
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title abstract 2
- DZAIOXUZHHTJKN-VKHMYHEASA-N 3S,4-dihydroxy-butyric acid Chemical compound OC[C@@H](O)CC(O)=O DZAIOXUZHHTJKN-VKHMYHEASA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
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)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2236996P | 1996-07-29 | 1996-07-29 | |
| US60022369 | 1996-07-29 | ||
| PCT/US1997/011654 WO1998004543A1 (en) | 1996-07-29 | 1997-07-01 | Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU3515497A true AU3515497A (en) | 1998-02-20 |
Family
ID=21809241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU35154/97A Abandoned AU3515497A (en) | 1996-07-29 | 1997-07-01 | Improved process for the synthesis of protected esters of (s)-3,4-dihydroxybutyric acid |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5998633A (https=) |
| EP (1) | EP0915866B1 (https=) |
| JP (1) | JP2000515882A (https=) |
| KR (1) | KR100447370B1 (https=) |
| CN (1) | CN1093126C (https=) |
| AT (1) | ATE215078T1 (https=) |
| AU (1) | AU3515497A (https=) |
| CO (1) | CO4950542A1 (https=) |
| DE (1) | DE69711391T2 (https=) |
| DK (1) | DK0915866T3 (https=) |
| ES (1) | ES2176756T3 (https=) |
| HU (1) | HU226465B1 (https=) |
| IL (1) | IL127058A (https=) |
| PT (1) | PT915866E (https=) |
| TR (1) | TR199900191T2 (https=) |
| WO (1) | WO1998004543A1 (https=) |
| ZA (1) | ZA976705B (https=) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CA2049536C (en) * | 1991-05-13 | 1999-07-06 | Rawle I. Hollingsworth | Process for the preparation of 3,4-dihydroxybutanoic acid and salts thereof |
| 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 |
-
1997
- 1997-07-01 AU AU35154/97A patent/AU3515497A/en not_active Abandoned
- 1997-07-01 WO PCT/US1997/011654 patent/WO1998004543A1/en not_active Ceased
- 1997-07-01 DE DE69711391T patent/DE69711391T2/de not_active Expired - Fee Related
- 1997-07-01 DK DK97931557T patent/DK0915866T3/da active
- 1997-07-01 PT PT97931557T patent/PT915866E/pt unknown
- 1997-07-01 ES ES97931557T patent/ES2176756T3/es not_active Expired - Lifetime
- 1997-07-01 KR KR10-1999-7000721A patent/KR100447370B1/ko not_active Expired - Fee Related
- 1997-07-01 AT AT97931557T patent/ATE215078T1/de not_active IP Right Cessation
- 1997-07-01 CN CN97195996A patent/CN1093126C/zh not_active Expired - Fee Related
- 1997-07-01 TR TR1999/00191T patent/TR199900191T2/xx unknown
- 1997-07-01 IL IL12705897A patent/IL127058A/en not_active IP Right Cessation
- 1997-07-01 EP EP97931557A patent/EP0915866B1/en not_active Expired - Lifetime
- 1997-07-01 HU HU9904348A patent/HU226465B1/hu not_active IP Right Cessation
- 1997-07-01 US US09/230,397 patent/US5998633A/en not_active Expired - Fee Related
- 1997-07-01 JP JP10508813A patent/JP2000515882A/ja not_active Ceased
- 1997-07-28 ZA ZA9706705A patent/ZA976705B/xx unknown
- 1997-07-28 CO CO97042973A patent/CO4950542A1/es unknown
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 |
| ZA976705B (en) | 1998-02-10 |
| CN1093126C (zh) | 2002-10-23 |
| 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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