WO2003004455A3 - Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation - Google Patents

Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation Download PDF

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Publication number
WO2003004455A3
WO2003004455A3 PCT/EP2002/007308 EP0207308W WO03004455A3 WO 2003004455 A3 WO2003004455 A3 WO 2003004455A3 EP 0207308 W EP0207308 W EP 0207308W WO 03004455 A3 WO03004455 A3 WO 03004455A3
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WO
WIPO (PCT)
Prior art keywords
preparation
methods
intermediates
protecting group
acid derivatives
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.)
Ceased
Application number
PCT/EP2002/007308
Other languages
German (de)
French (fr)
Other versions
WO2003004455A2 (en
Inventor
Reinhold Oehrlein
Gabriele Baisch
Hans Joerg Kirner
Frank Bienewald
Stephan Burkhardt
Martin Studer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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
Priority to US10/482,946 priority Critical patent/US7317123B2/en
Priority to HU0401006A priority patent/HUP0401006A2/en
Priority to CA002453211A priority patent/CA2453211A1/en
Priority to EP02764615A priority patent/EP1404642B1/en
Priority to PCT/EP2002/007308 priority patent/WO2003004455A2/en
Priority to HR20040117A priority patent/HRP20040117A2/en
Priority to IL15971802A priority patent/IL159718A0/en
Priority to PL02367774A priority patent/PL367774A1/en
Priority to JP2003510423A priority patent/JP2004533481A/en
Priority to DK02764615.7T priority patent/DK1404642T3/en
Priority to AT02764615T priority patent/ATE457972T1/en
Priority to AU2002328835A priority patent/AU2002328835A1/en
Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to DE60235365T priority patent/DE60235365D1/en
Priority to CZ2004158A priority patent/CZ2004158A3/en
Priority to SK79-2004A priority patent/SK792004A3/en
Publication of WO2003004455A2 publication Critical patent/WO2003004455A2/en
Publication of WO2003004455A3 publication Critical patent/WO2003004455A3/en
Anticipated expiration legal-status Critical
Priority to US11/941,347 priority patent/US7504532B2/en
Ceased legal-status Critical Current

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    • 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
    • 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
    • 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
    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Carbon And Carbon Compounds (AREA)

Abstract

The invention relates to synthesis methods for the preparation of the intermediates, which are suitable for the preparation of statin derivatives, especially to synthesis methods of the intermediate of formula (VI) wherein Ra' and Rc' are each independently of the other hydrogen or hydroxy-protecting group or together are a bridging hydroxy-protecting group, and Rb is a carboxy-protecting group, which methods are carried out by conversion of the intermediate of formula (XVI) wherein Ra' and Rc' are each independently of the other hydrogen or a hydroxy-protecting group, R* and R** are each independently of the other hydrogen or an amide-protecting group, and Rb is a carboxy-protecting group; which methods proceed to further intermediates and methods for their preparation.
PCT/EP2002/007308 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation Ceased WO2003004455A2 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
AT02764615T ATE457972T1 (en) 2001-07-06 2002-07-02 METHOD FOR PRODUCING 7-AMINO-SYN-3,5-DIHYDROXYHEPTANIC ACID DERIVATIVES AND INTERMEDIATE COMPOUNDS OF THIS METHOD AND THEIR PRODUCTION
CA002453211A CA2453211A1 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
EP02764615A EP1404642B1 (en) 2001-07-06 2002-07-02 Process for the preparatiom of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
PCT/EP2002/007308 WO2003004455A2 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
HR20040117A HRP20040117A2 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
IL15971802A IL159718A0 (en) 2001-07-06 2002-07-02 Synthesis of intermediates for preparation of stating derivatives
PL02367774A PL367774A1 (en) 2001-07-06 2002-07-02 Synthesis and intermediates
JP2003510423A JP2004533481A (en) 2001-07-06 2002-07-02 Method for producing 7-aminoSYN3,5-dihydroxyheptanoic acid derivative, intermediates thereof and method for producing intermediate
DK02764615.7T DK1404642T3 (en) 2001-07-06 2002-07-02 Process for Preparation of 7-Amino-Syn-3,5-Dihydroxyheptanoic Acid Derivatives, Intermediates Therefore, and Methods for their Preparation
US10/482,946 US7317123B2 (en) 2001-07-06 2002-07-02 Process for preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
HU0401006A HUP0401006A2 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn-3,5-dihidroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
AU2002328835A AU2002328835A1 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation
DE60235365T DE60235365D1 (en) 2001-07-06 2002-07-02 PROCESS FOR THE PREPARATION OF 7-AMINO-SYN-3,5-DIHYDROXYHEPTANSÄUREDERIVATEN AND BETWEEN COMPOUNDS OF THIS PROCESS AND THEIR PREPARATION
CZ2004158A CZ2004158A3 (en) 2001-07-06 2002-07-02 Synthesis and intermediates of 3,5-dihydroxyheptanoic acid derivatives
SK79-2004A SK792004A3 (en) 2001-07-06 2002-07-02 Synthesis and intermediates of 3,5-dihydroxy heptanoic acid derivatives
US11/941,347 US7504532B2 (en) 2001-07-06 2007-11-16 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP01810670 2001-07-06
EP01810670.8 2001-07-06
PCT/EP2002/007308 WO2003004455A2 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10482946 A-371-Of-International 2002-07-02
US11/941,347 Division US7504532B2 (en) 2001-07-06 2007-11-16 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation

Publications (2)

Publication Number Publication Date
WO2003004455A2 WO2003004455A2 (en) 2003-01-16
WO2003004455A3 true WO2003004455A3 (en) 2003-03-20

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PCT/EP2002/007308 Ceased WO2003004455A2 (en) 2001-07-06 2002-07-02 Process for the preparation of 7-amino syn 3,5-dihydroxy heptanoic acid derivatives, intermediates thereof and methods for their preparation

Country Status (15)

Country Link
US (2) US7317123B2 (en)
EP (1) EP1404642B1 (en)
JP (1) JP2004533481A (en)
AT (1) ATE457972T1 (en)
AU (1) AU2002328835A1 (en)
CA (1) CA2453211A1 (en)
CZ (1) CZ2004158A3 (en)
DE (1) DE60235365D1 (en)
DK (1) DK1404642T3 (en)
HR (1) HRP20040117A2 (en)
HU (1) HUP0401006A2 (en)
IL (1) IL159718A0 (en)
PL (1) PL367774A1 (en)
SK (1) SK792004A3 (en)
WO (1) WO2003004455A2 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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)
CN1610657A (en) 2001-07-06 2005-04-27 西巴特殊化学品控股有限公司 Process for preparing intermediates for synthesizing statin derivatives, especially 7-amino 3,5-dihydroxyheptanoic acid derivatives, and intermediates thereof
US7361772B2 (en) 2001-08-16 2008-04-22 Biocon Limited Process for the production of atorvastatin calcium
HUP0500074A3 (en) 2002-03-18 2005-07-28 Biocon Ltd Bangalore Amorphous hmg-coa reductase inhibitors of desired particle size and process for producing them
US7179942B2 (en) 2002-07-05 2007-02-20 Bicon Limited Halo-substituted active methylene compounds
SI1631533T1 (en) 2003-04-22 2009-08-31 Bicon Ltd Novel process for stereoselective reduction of beta-ketoesters
KR20070092994A (en) 2003-06-18 2007-09-14 테바 파마슈티컬 인더스트리즈 리미티드 Fluvastatin sodium crystalline form IV, LVII, LVII, LV and LVII, preparation method thereof, composition comprising the same and method of using the same
US7368468B2 (en) 2003-06-18 2008-05-06 Teva Pharmaceutical Industries Ltd. Fluvastatin sodium crystal forms XIV, LXXIII, LXXIX, LXXX and LXXXVII, processes for preparing them, compositions containing them and methods of using them
WO2005026107A1 (en) 2003-09-18 2005-03-24 Biocon Limited Novel process for the preparation of tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate
US7851624B2 (en) 2003-12-24 2010-12-14 Teva Pharamaceutical Industries Ltd. Triol form of rosuvastatin and synthesis of rosuvastatin
WO2007022488A2 (en) 2005-08-16 2007-02-22 Teva Pharmaceutical Industries Ltd. Crystalline rosuvastatin intermediate
EP2778229A1 (en) 2013-03-11 2014-09-17 Sandoz Ag Process for the enantioselective preparation of 3-hydroxyglutaric acid monoesters and their use
CN103361386B (en) * 2013-06-28 2015-04-15 苏州汉酶生物技术有限公司 Method for preparing rosuvastatin intermediate

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EP0436851A1 (en) * 1989-12-21 1991-07-17 ZAMBON GROUP S.p.A. Compounds active as inhibitors of the enzyme HMG-CoA reductase and pharmaceutical compositions containing them
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Also Published As

Publication number Publication date
JP2004533481A (en) 2004-11-04
WO2003004455A2 (en) 2003-01-16
ATE457972T1 (en) 2010-03-15
EP1404642B1 (en) 2010-02-17
EP1404642A2 (en) 2004-04-07
CA2453211A1 (en) 2003-01-16
PL367774A1 (en) 2005-03-07
US20080125601A1 (en) 2008-05-29
US20040242916A1 (en) 2004-12-02
IL159718A0 (en) 2004-06-20
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HRP20040117A2 (en) 2004-10-31
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US7504532B2 (en) 2009-03-17

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