ES2328213B1 - Procedimiento de obtencion del acido zaragocico y derivados del mismo. - Google Patents

Procedimiento de obtencion del acido zaragocico y derivados del mismo. Download PDF

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Publication number
ES2328213B1
ES2328213B1 ES200801303A ES200801303A ES2328213B1 ES 2328213 B1 ES2328213 B1 ES 2328213B1 ES 200801303 A ES200801303 A ES 200801303A ES 200801303 A ES200801303 A ES 200801303A ES 2328213 B1 ES2328213 B1 ES 2328213B1
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Prior art keywords
formula
compound
mixtures
enantiomers
quad
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Expired - Fee Related
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ES200801303A
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English (en)
Spanish (es)
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ES2328213A1 (es
Inventor
Pedro Noheda Marin
Luis Miguel Lozano Gordillo
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Consejo Superior de Investigaciones Cientificas CSIC
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Consejo Superior de Investigaciones Cientificas CSIC
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Priority to ES200801303A priority Critical patent/ES2328213B1/es
Application filed by Consejo Superior de Investigaciones Cientificas CSIC filed Critical Consejo Superior de Investigaciones Cientificas CSIC
Priority to AU2009245669A priority patent/AU2009245669A1/en
Priority to JP2011507951A priority patent/JP2011524856A/ja
Priority to EP09742185A priority patent/EP2311841A4/en
Priority to PCT/ES2009/070140 priority patent/WO2009135979A1/es
Priority to US12/991,531 priority patent/US20110207947A1/en
Priority to CN2009801239426A priority patent/CN102066383A/zh
Publication of ES2328213A1 publication Critical patent/ES2328213A1/es
Application granted granted Critical
Publication of ES2328213B1 publication Critical patent/ES2328213B1/es
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/60—Maleic acid esters; Fumaric acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of 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
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon 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
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon 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 by ester radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/20—Oxygen atoms
    • 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
    • C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Furan Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
ES200801303A 2008-05-06 2008-05-06 Procedimiento de obtencion del acido zaragocico y derivados del mismo. Expired - Fee Related ES2328213B1 (es)

Priority Applications (7)

Application Number Priority Date Filing Date Title
ES200801303A ES2328213B1 (es) 2008-05-06 2008-05-06 Procedimiento de obtencion del acido zaragocico y derivados del mismo.
JP2011507951A JP2011524856A (ja) 2008-05-06 2009-05-05 ザラゴジン酸およびその誘導体を得る方法
EP09742185A EP2311841A4 (en) 2008-05-06 2009-05-05 PROCESS FOR THE PRODUCTION OF SARAGOSSAIC ACIDS AND DERIVATIVES THEREOF
PCT/ES2009/070140 WO2009135979A1 (es) 2008-05-06 2009-05-05 Procedimiento de obtención del ácido zaragócico y derivados del mismo
AU2009245669A AU2009245669A1 (en) 2008-05-06 2009-05-05 Method for obtaining zaragozic acid and derivatives thereof
US12/991,531 US20110207947A1 (en) 2008-05-06 2009-05-05 Method for obtaining zaragozic acid and derivatives thereof
CN2009801239426A CN102066383A (zh) 2008-05-06 2009-05-05 获得萨拉哥酸及其衍生物的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200801303A ES2328213B1 (es) 2008-05-06 2008-05-06 Procedimiento de obtencion del acido zaragocico y derivados del mismo.

Publications (2)

Publication Number Publication Date
ES2328213A1 ES2328213A1 (es) 2009-11-10
ES2328213B1 true ES2328213B1 (es) 2010-07-23

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
ES200801303A Expired - Fee Related ES2328213B1 (es) 2008-05-06 2008-05-06 Procedimiento de obtencion del acido zaragocico y derivados del mismo.

Country Status (7)

Country Link
US (1) US20110207947A1 (enExample)
EP (1) EP2311841A4 (enExample)
JP (1) JP2011524856A (enExample)
CN (1) CN102066383A (enExample)
AU (1) AU2009245669A1 (enExample)
ES (1) ES2328213B1 (enExample)
WO (1) WO2009135979A1 (enExample)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4215048A (en) * 1979-05-18 1980-07-29 Ortho Pharmaceutical Corporation Total synthesis of (1RS, 4SR, 5RS)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid
US5262435A (en) 1992-02-10 1993-11-16 Merck & Co., Inc. Cholesterol lowering compounds
US5302604A (en) * 1992-03-09 1994-04-12 Merck & Co., Inc. Cholesterol lowering compounds produced by directed biosynthesis
WO1993017557A1 (en) 1992-03-09 1993-09-16 Merck & Co., Inc. Cholesterol lowering compounds produced by directed biosynthesis
US5283256A (en) * 1992-07-22 1994-02-01 Merck & Co., Inc. Cholesterol-lowering agents
US5326783A (en) 1992-08-25 1994-07-05 Merck & Co., Inc. Cholesterol lowering compounds
CN101052621A (zh) * 2004-09-23 2007-10-10 辉瑞产品公司 4－氨基取代－2－取代－1，2，3，4－四氢喹啉化合物

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
EVANS, D. A. et al. "{}Asymmetric Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C"{}. Journal of the American Chemical Society, 1994, Volumen 116, páginas 12111-12112. Ver página 12112, esquema 2, compuesto 14. *
MARUYAMA, Y. et al. "{}Ruthenium-catalysed reductive cleavage of allylic esters with formic acid and triethylamine. Application to short-step synthesis of a-hydroxy acids"{}. Journal of Organometallic Chemistry, 1994, Volumen 473, páginas 257-264. Ver página 259, columna 2, compuesto 10. *
NAKAMURA, S. et al. "{}Total synthesis of zaragozic acid C by an aldol-based strategy"{}. Tetrahedron, 2005, Volumen 61, páginas 11078-11106. Ver resumen; página 11079, esquema 1; página 11085, esquema 10. *
TOMOOKA, K. "{}Stereoselective Total Synthesis of Zaragozic Acid A based on an acetal [1,2] Wittig Rearrangement"{}. Angewandte Chemie International Edition in English, 2000, Volumen 39, Número 24, páginas 4502-4505. Ver página 4503, esquema 3. *
TROST, B. M. et al. "{}Bromomalonates as Synthetic Reagents. Transfer Alkylations"{}. Journal of the American Chemical Society, 1976, Volumen 98, Número 5, páginas 1204-1212. Ver página 1205, tabla I. *
WATANABLE, H. et al. "{}A facile route to 3,7-cis-disubstituted cycloocta-1,5-diene-1,2,5,6-tetracarboxylates through photochemical [2+2] cycloaddition of 3-substituted cyclobutene- 1,2-dicarboxylates and thermal isomerization"{}. Chemical Communications, 1999, páginas 1753-1754. Ver página 1754, esquema 3, compuesto 5. *

Also Published As

Publication number Publication date
EP2311841A4 (en) 2012-05-09
AU2009245669A1 (en) 2009-11-12
EP2311841A1 (en) 2011-04-20
WO2009135979A1 (es) 2009-11-12
ES2328213A1 (es) 2009-11-10
CN102066383A (zh) 2011-05-18
US20110207947A1 (en) 2011-08-25
JP2011524856A (ja) 2011-09-08

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