HRPK20040119B3 - Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3,5-dihydroxy heptanoic acid derivatives, and intermediates thereof - Google Patents

Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3,5-dihydroxy heptanoic acid derivatives, and intermediates thereof

Info

Publication number
HRPK20040119B3
HRPK20040119B3 HR20040119A HRP20040119A HRPK20040119B3 HR PK20040119 B3 HRPK20040119 B3 HR PK20040119B3 HR 20040119 A HR20040119 A HR 20040119A HR P20040119 A HRP20040119 A HR P20040119A HR PK20040119 B3 HRPK20040119 B3 HR PK20040119B3
Authority
HR
Croatia
Prior art keywords
intermediates
preparation
synthesis
amino
derivatives
Prior art date
Application number
HR20040119A
Other languages
English (en)
Inventor
�hrlein Reinhold
Baisch Gabriele
End Nicole
Burkhardt Stephen
Studer Martin
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Publication of HRP20040119A2 publication Critical patent/HRP20040119A2/xx
Publication of HRPK20040119B3 publication Critical patent/HRPK20040119B3/xx

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Postupak za pripravu intermedijarnih spojeva kojisu prikladni za pripravu derivata statina, naznačen time, da on obuhvaća pripravu ključnog intermedijata formule Iu kojoj X predstavlja halogen, aciloksi, aktivirani hidro-karbiloksi, aktivirani hidrokarbiltio ili -N(CH3)-OCH3, Ra je hidroksi zaštitna skupina i Rb je karboksi zaštitna skupina, pri čemu se ključni intermedijat formule I pripravlja pretvorbom spoja formule XIu kojoj Ra predstavlja hidroksi zaštitnu skupinu i Rb je karboksi zaštitna skupina, u odgovarajući spoj formule I upotrebomreagenta koji uvodi radikal X. Patent sadrži još 26 patentnih zahtjeva.
HR20040119A 2001-07-06 2004-02-05 Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3,5-dihydroxy heptanoic acid derivatives, and intermediates thereof HRPK20040119B3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP01810670 2001-07-06
PCT/EP2002/007307 WO2003004450A1 (en) 2001-07-06 2002-07-02 Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3,5-dihydroxy heptanoic acid derivatives, and intermediates thereof

Publications (2)

Publication Number Publication Date
HRP20040119A2 HRP20040119A2 (en) 2005-04-30
HRPK20040119B3 true HRPK20040119B3 (en) 2006-07-31

Family

ID=8184014

Family Applications (1)

Application Number Title Priority Date Filing Date
HR20040119A HRPK20040119B3 (en) 2001-07-06 2004-02-05 Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3,5-dihydroxy heptanoic acid derivatives, and intermediates thereof

Country Status (17)

Country Link
US (3) US7420078B2 (hr)
EP (2) EP2161250A1 (hr)
JP (1) JP2004533479A (hr)
KR (2) KR20040017277A (hr)
CN (2) CN101880227A (hr)
AR (3) AR034735A1 (hr)
AU (1) AU2002354701B2 (hr)
BR (1) BR0210842A (hr)
CA (1) CA2448917A1 (hr)
CZ (1) CZ2004150A3 (hr)
ES (1) ES2340260T3 (hr)
HR (1) HRPK20040119B3 (hr)
HU (1) HUP0401145A3 (hr)
IL (3) IL159050A0 (hr)
PL (1) PL366392A1 (hr)
PT (1) PT1404642E (hr)
WO (1) WO2003004450A1 (hr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6101484A (en) 1999-03-31 2000-08-08 Mercata, Inc. Dynamic market equilibrium management system, process and article of manufacture
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)
IL159050A0 (en) 2001-07-06 2004-05-12 Ciba Sc Holding Ag Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3, 5-dihydroy heptanoic acid derivatives, and intermediates thereof
EP1417180B1 (en) 2001-07-13 2006-12-27 AstraZeneca UK Limited Preparation of aminopyrimidine compounds
US7361772B2 (en) 2001-08-16 2008-04-22 Biocon Limited Process for the production of atorvastatin calcium
BR0215644A (pt) 2002-03-18 2004-12-21 Biocon Ltd Inibidores de redutase de hmg-coa amorfos do tamanho de partìcula desejado
US7179942B2 (en) 2002-07-05 2007-02-20 Bicon Limited Halo-substituted active methylene compounds
AU2003295684A1 (en) * 2002-11-15 2004-06-15 Teva Pharmaceutical Industries Ltd. Synthesis of 3,5-dihydroxy-7-pyrrol-1-yl heptanoic acids
SI1631533T1 (sl) 2003-04-22 2009-08-31 Bicon Ltd Nov postopek za stereoselektivno redukcijo beta - ketoestrov
WO2005026107A1 (en) 2003-09-18 2005-03-24 Biocon Limited Novel process for the preparation of tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate
GB0428328D0 (en) 2004-12-24 2005-02-02 Astrazeneca Uk Ltd Chemical process
WO2007034909A1 (ja) * 2005-09-22 2007-03-29 Kaneka Corporation （３ｒ，５ｒ）－７－アミノ－３，５－ジヒドロキシヘプタン酸誘導体の製造法
KR20100080432A (ko) * 2008-12-29 2010-07-08 한미약품 주식회사 스타틴 화합물의 신규 제조방법 및 이에 사용되는 벤조티아졸릴 술폰 화합물
SI2616454T1 (sl) * 2010-09-16 2015-08-31 Dsm Sinochem Pharmaceuticals Netherlands B.V. Estri heksanojskih kislin, kot vmesne spojine za pripravo atorvastatina
US8420773B2 (en) 2011-05-06 2013-04-16 Basf Se Process for producing water-absorbing polymer particles
JP6073292B2 (ja) 2011-05-06 2017-02-01 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 吸水性ポリマー粒子の製造法
JP6181063B2 (ja) * 2011-11-28 2017-08-16 マイラン ラボラトリーズ リミテッドＭｙｌａｎ Ｌａｂｏｒａｔｏｒｉｅｓ Ｌｉｍｉｔｅｄ ＨＭＧ−ＣｏＡレダクターゼ阻害剤の中間体の新規な製造方法
US10149720B2 (en) 2013-03-08 2018-12-11 Auris Health, Inc. Method, apparatus, and a system for facilitating bending of an instrument in a surgical or medical robotic environment
EP2778229A1 (de) * 2013-03-11 2014-09-17 Sandoz Ag Verfahren zur enantioselektiven Herstellung von 3-Hydroxyglutarsäuremonoestern und deren Verwendung
US10376672B2 (en) 2013-03-15 2019-08-13 Auris Health, Inc. Catheter insertion system and method of fabrication
EP2983711A4 (en) 2013-04-08 2016-11-23 Cytodyn Inc FELLINED ANTIBODIES AND METHODS OF TREATING RETROVIRAL INFECTIONS IN FELINES
CN104230879B (zh) * 2014-08-15 2016-08-24 新发药业有限公司 一种2-((4r, 6s)-6-甲酰基-2,2-二取代基-1,3-二氧六环-4-基)乙酸酯制备方法
CN108033899B (zh) * 2017-12-06 2020-04-10 浙江科技学院 一种(r)-6-氰基-5-羟基-3-羰基己酸叔丁酯的制备方法
CN108997324A (zh) * 2018-08-21 2018-12-14 南京欧信医药技术有限公司 瑞舒伐他汀钙中间体的制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4677211A (en) * 1984-06-29 1987-06-30 Sandoz Pharmaceuticals Corp. Preparation of lactones
US4950775A (en) * 1985-10-11 1990-08-21 University Of California Antihypercholesterolemic compounds and synthesis thereof
US5003080A (en) 1988-02-22 1991-03-26 Warner-Lambert Company Process for trans-6-(2-(substituted-pyrrol-1-yl)alkyl)pryan-2-one inhibitors of cholesterol synthesis
IT1226726B (it) * 1988-07-29 1991-02-05 Zambon Spa Composti attivi come inibitori della biosintesi del colesterolo.
US5196440A (en) * 1988-07-29 1993-03-23 Zambon Group S.P.A. Compounds active as inhibitors of the cholesterol biosynthesis
IT1224795B (it) * 1988-12-01 1990-10-24 Sigma Tau Ind Farmaceuti Uso dell'acetil d-carnitina nel trattamento terapeutico del glaucoma e composizioni farmaceutiche utili in tale trattamento
IT1237792B (it) 1989-12-21 1993-06-17 Zambon Spa Composti attivi come inibitori dell'enzima hmg-coa reduttasi
US5155251A (en) 1991-10-11 1992-10-13 Warner-Lambert Company Process for the synthesis of (5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate
JP3652394B2 (ja) * 1995-01-27 2005-05-25 高砂香料工業株式会社 Ｎ−置換−７−アミノ−５−ヒドロキシ−３−オキソヘプタン酸誘導体およびその製造法
JP2003535077A (ja) * 2000-05-26 2003-11-25 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド インドール誘導体を製造する方法、および該方法の中間体
IL159050A0 (en) 2001-07-06 2004-05-12 Ciba Sc Holding Ag Process for the preparation of intermediates useful in the synthesis of statin derivatives especially 7-amino 3, 5-dihydroy heptanoic acid derivatives, and intermediates thereof
US7199261B2 (en) 2001-07-06 2007-04-03 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
CA2453211A1 (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, intermediates thereof and methods for their preparation

Also Published As

Publication number Publication date
US20110046411A1 (en) 2011-02-24
CZ2004150A3 (cs) 2004-09-15
US8026383B2 (en) 2011-09-27
PL366392A1 (en) 2005-01-24
US20040186313A1 (en) 2004-09-23
HUP0401145A3 (en) 2008-08-28
IL214165A0 (en) 2011-08-31
BR0210842A (pt) 2004-07-13
AU2002354701B2 (en) 2007-11-22
CN1610657A (zh) 2005-04-27
EP2161250A1 (en) 2010-03-10
CN101880227A (zh) 2010-11-10
PT1404642E (pt) 2010-03-29
AR034735A1 (es) 2004-03-17
EP1404639A1 (en) 2004-04-07
AR034733A1 (es) 2004-03-17
WO2003004450A1 (en) 2003-01-16
KR20040017278A (ko) 2004-02-26
IL159050A0 (en) 2004-05-12
CA2448917A1 (en) 2003-01-16
US20080312466A1 (en) 2008-12-18
JP2004533479A (ja) 2004-11-04
US7420078B2 (en) 2008-09-02
AR034734A1 (es) 2004-03-17
IL214164A0 (en) 2011-08-31
KR20040017277A (ko) 2004-02-26
ES2340260T3 (es) 2010-06-01
HRP20040119A2 (en) 2005-04-30
US7855302B2 (en) 2010-12-21
HUP0401145A2 (hu) 2004-09-28

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