CA2450820C - Procedes permettant de preparer des formes salines calciques de statines - Google Patents

Procedes permettant de preparer des formes salines calciques de statines Download PDF

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Publication number
CA2450820C
CA2450820C CA2450820A CA2450820A CA2450820C CA 2450820 C CA2450820 C CA 2450820C CA 2450820 A CA2450820 A CA 2450820A CA 2450820 A CA2450820 A CA 2450820A CA 2450820 C CA2450820 C CA 2450820C
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CA
Canada
Prior art keywords
statin
calcium
atorvastatin
mixture
ester derivative
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.)
Expired - Fee Related
Application number
CA2450820A
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English (en)
Other versions
CA2450820A1 (fr
Inventor
Valerie Niddam-Hildesheim
Revital Lifshitz-Liron
Rami Lidor-Hadas
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.)
Teva Pharmaceutical Industries Ltd
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Teva Pharmaceutical Industries Ltd
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 claimed from US10/037,412 external-priority patent/US6528661B2/en
Application filed by Teva Pharmaceutical Industries Ltd filed Critical Teva Pharmaceutical Industries Ltd
Publication of CA2450820A1 publication Critical patent/CA2450820A1/fr
Application granted granted Critical
Publication of CA2450820C publication Critical patent/CA2450820C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C07D209/24—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 with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—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
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • 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

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne des procédés permettant de préparer un sel calcique d'une statine à partir d'un dérivé d'ester ou d'un dérivé d'ester protégé de la statine au moyen d'hydroxyde de calcium. Le dérivé d'ester ou le dérivé d'ester protégé est mis en contact avec l'hydroxyde de calcium pour obtenir le sel calcique. Les statines préférées sont la rosuvastatine, la pitavastatine et l'atorvastatine, la simvastatine et la lovastatine. Dans les procédés qui commencent avec un dérivé d'ester de statine protégé, le groupe protecteur est soit hydrolysé pendant la formation du sel par contact avec l'hydroxyde de calcium, soit mis en contact avec un catalyseur acide, puis avec l'hydroxyde de calcium.
CA2450820A 2001-08-16 2002-08-16 Procedes permettant de preparer des formes salines calciques de statines Expired - Fee Related CA2450820C (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US31281201P 2001-08-16 2001-08-16
US60/312,812 2001-08-16
US10/037,412 2001-10-24
US10/037,412 US6528661B2 (en) 2000-11-16 2001-10-24 Hydrolysis of [R(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino) carbonyl]-1H-pyrrole-1-heptanoic acid esters with calcium hydroxide
PCT/US2002/026012 WO2003016317A1 (fr) 2001-08-16 2002-08-16 Procedes permettant de preparer des formes salines calciques de statines

Publications (2)

Publication Number Publication Date
CA2450820A1 CA2450820A1 (fr) 2003-02-27
CA2450820C true CA2450820C (fr) 2011-03-15

Family

ID=26714105

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2450820A Expired - Fee Related CA2450820C (fr) 2001-08-16 2002-08-16 Procedes permettant de preparer des formes salines calciques de statines

Country Status (17)

Country Link
EP (1) EP1425287A4 (fr)
JP (2) JP4188826B2 (fr)
CN (1) CN100430405C (fr)
AU (1) AU2002324715B2 (fr)
CA (1) CA2450820C (fr)
CZ (1) CZ2004337A3 (fr)
HR (1) HRPK20040255B3 (fr)
HU (1) HUP0500616A3 (fr)
IL (2) IL160077A0 (fr)
IS (1) IS7148A (fr)
MX (1) MXPA04001451A (fr)
NO (1) NO20041082L (fr)
NZ (1) NZ529913A (fr)
PL (1) PL370407A1 (fr)
SK (1) SK1402004A3 (fr)
TR (1) TR200302281T2 (fr)
WO (1) WO2003016317A1 (fr)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
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CN102302452B (zh) * 2011-09-14 2012-11-21 海南美大制药有限公司 匹伐他汀钙脂质体固体制剂
CN102796036B (zh) * 2012-09-12 2014-06-04 江苏阿尔法药业有限公司 一种阿托伐他汀钙的制备方法
CN103724278B (zh) * 2013-12-12 2019-03-29 江苏阿尔法药业有限公司 他汀类中间体及其衍生物的制备方法
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KR20160126700A (ko) 2015-04-24 2016-11-02 미래파인켐 주식회사 스타틴의 중간체, 이의 제조방법 및 이를 이용한 로수바스타틴의 제조방법
CN105017231B (zh) * 2015-06-26 2018-01-26 上海应用技术学院 多取代吲哚类他汀含氟修饰物及其用途
CN105111173B (zh) * 2015-06-26 2017-06-23 上海应用技术学院 他汀含氟衍生物及其用途
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CN100430405C (zh) 2008-11-05
PL370407A1 (en) 2005-05-30
IS7148A (is) 2004-02-11
NO20041082L (no) 2004-03-15
JP2009024008A (ja) 2009-02-05
HUP0500616A2 (hu) 2005-11-28
JP2005500382A (ja) 2005-01-06
CN1543468A (zh) 2004-11-03
JP4188826B2 (ja) 2008-12-03
IL160077A (en) 2007-10-31
WO2003016317A1 (fr) 2003-02-27
AU2002324715B2 (en) 2009-03-12
EP1425287A1 (fr) 2004-06-09
SK1402004A3 (sk) 2005-01-03
NZ529913A (en) 2005-03-24
CA2450820A1 (fr) 2003-02-27
EP1425287A4 (fr) 2005-09-07
HRPK20040255B3 (en) 2006-02-28
TR200302281T2 (tr) 2004-09-21
HRP20040255A2 (en) 2004-08-31
CZ2004337A3 (cs) 2005-01-12
MXPA04001451A (es) 2005-02-17
HUP0500616A3 (en) 2011-07-28
IL160077A0 (en) 2004-06-20

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