ES2328214B1 - Procedimiento de obtencion de las cinatrinas c3 y c1. - Google Patents

Procedimiento de obtencion de las cinatrinas c3 y c1. Download PDF

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Publication number
ES2328214B1
ES2328214B1 ES200801305A ES200801305A ES2328214B1 ES 2328214 B1 ES2328214 B1 ES 2328214B1 ES 200801305 A ES200801305 A ES 200801305A ES 200801305 A ES200801305 A ES 200801305A ES 2328214 B1 ES2328214 B1 ES 2328214B1
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ES
Spain
Prior art keywords
formula
compound
alkyl group
mixtures
stereoisomers
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
ES200801305A
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English (en)
Spanish (es)
Other versions
ES2328214A1 (es
Inventor
Pedro Noheda Marin
Luis Miguel Lozano Gordillo
Sergio Maroto Quintana
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.)
Consejo Superior de Investigaciones Científicas
Original Assignee
Consejo Superior de Investigaciones Científicas
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 ES200801305A priority Critical patent/ES2328214B1/es
Application filed by Consejo Superior de Investigaciones Científicas filed Critical Consejo Superior de Investigaciones Científicas
Priority to EP09742184A priority patent/EP2287157A4/en
Priority to US12/991,523 priority patent/US20110275838A1/en
Priority to JP2011507950A priority patent/JP2011523631A/ja
Priority to PCT/ES2009/070139 priority patent/WO2009135978A1/es
Priority to AU2009245668A priority patent/AU2009245668A1/en
Priority to CN2009801240480A priority patent/CN102066350A/zh
Publication of ES2328214A1 publication Critical patent/ES2328214A1/es
Application granted granted Critical
Publication of ES2328214B1 publication Critical patent/ES2328214B1/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
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/40—Succinic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00—Compounds containing selenium
    • 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
    • C07C67/313—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 doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • 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
    • C07C69/593—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
    • 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
    • C07C69/604—Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups
    • 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
    • C07C69/734—Ethers
    • 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
    • C07D303/48—Compounds containing oxirane rings 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, e.g. ester or nitrile 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
    • C07D307/26—Heterocyclic compounds containing five-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
    • C07D307/30—Heterocyclic compounds containing five-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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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)
  • Epoxy Compounds (AREA)
ES200801305A 2008-05-06 2008-05-06 Procedimiento de obtencion de las cinatrinas c3 y c1. Expired - Fee Related ES2328214B1 (es)

Priority Applications (7)

Application Number Priority Date Filing Date Title
ES200801305A ES2328214B1 (es) 2008-05-06 2008-05-06 Procedimiento de obtencion de las cinatrinas c3 y c1.
US12/991,523 US20110275838A1 (en) 2008-05-06 2009-05-05 Method for obtaining cinatrins c3 and c1
JP2011507950A JP2011523631A (ja) 2008-05-06 2009-05-05 シナトリンｃ３およびｃ１を得る方法
PCT/ES2009/070139 WO2009135978A1 (es) 2008-05-06 2009-05-05 Procedimiento de obtención de las cinatrinas c3 y c1
EP09742184A EP2287157A4 (en) 2008-05-06 2009-05-05 PROCESS FOR OBTAINING CINATRINE C3 AND C1
AU2009245668A AU2009245668A1 (en) 2008-05-06 2009-05-05 Method for obtaining cinatrins C3 and C1
CN2009801240480A CN102066350A (zh) 2008-05-06 2009-05-05 获得西那特林c3和c1的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200801305A ES2328214B1 (es) 2008-05-06 2008-05-06 Procedimiento de obtencion de las cinatrinas c3 y c1.

Publications (2)

Publication Number Publication Date
ES2328214A1 ES2328214A1 (es) 2009-11-10
ES2328214B1 true ES2328214B1 (es) 2010-07-23

Family

ID=41226503

Family Applications (1)

Application Number Title Priority Date Filing Date
ES200801305A Expired - Fee Related ES2328214B1 (es) 2008-05-06 2008-05-06 Procedimiento de obtencion de las cinatrinas c3 y c1.

Country Status (7)

Country Link
US (1) US20110275838A1 (enExample)
EP (1) EP2287157A4 (enExample)
JP (1) JP2011523631A (enExample)
CN (1) CN102066350A (enExample)
AU (1) AU2009245668A1 (enExample)
ES (1) ES2328214B1 (enExample)
WO (1) WO2009135978A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102503825A (zh) * 2011-11-11 2012-06-20 上海华谊（集团）公司 药物中间体丁酮二酸二酯类化合物的制备方法
CN115141199B (zh) * 2022-06-28 2023-04-07 江西师范大学 一种合成吴茱萸次碱的新方法
CN116354907B (zh) * 2023-04-12 2026-01-09 智仑新材料科技（西安）有限公司 一种含氟环氧树脂及其制备方法、应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03108490A (ja) 1989-06-30 1991-05-08 Shionogi & Co Ltd フォスフォリパーゼａ↓２阻害物質

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
BOIVIN, S. et al. "{}Synthesis and Reactivity of b-Phenylselanyl a-oxoesters"{}. Tetrahedron, 1997, Volumen 53, Número 49, páginas 16767-16782. Ver página 16770, esquema 4, figuras 2 y 6; página 16772, esquema 6, compuesto 9. *
CUZZUPE, A. N. et al. "{}Enantiospecific synthesis of the phospholipase A2 inhibitors (-)-cinatrin C1 and (+)-cinatrin C3"{}. Organic and Biomolecular Chemistry, 2003, Volumen 1, páginas 3572-3577. Ver resumen, esquemas 2, 4, 5 y 6. *
DALLA, V. & CATTEAU, J. P. "{}Chemocontrolled Reduction of a-Keto Esters by Hydrides: a Possible Solution for Selective Reduction of the Ester Function"{}. Tetrahedron, 1999, Volumen 55, páginas 6497-6510. Ver página 6499, tabla 1; página 6501, tabla 3. *
EVANS, D. A. et al."{}Aldol Reactions of Ketal-Protected Tartrate Ester Anolates. Asymmetric Syntheses and Absolute Stereochemical assignments of Phospholipase A2 Inhibitors Cinatrin C1 and C3"{}. Tetrahedron, 1997, Volumen 53, Número 26, página 8779-8794. Ver resumen, página 8781, esquema IV. *
LOWINGER, T. B. et al. "{}The Total Síntesis of (+)K252a"{}. Tetrahedron Letters, Volumen 36, Número 46, páginas 8383-8386. Ver página 8384, esquema 2, compuesto 12. *
PUJOL, B. et al. "{}Preparation of 1-Methoxycarbonyl-1-t- Butyldimethylsilyloxy Epoxides. Their Transformation into 3- Hydroxy 2-Acetal-Esters and certain 3-Hydroxy 2-Keto-esters"{}. Tetrahedron Letters, 1992, Volumen 33, Número 11, páginas 1447-1450. Ver página 1447, esquema, compuesto 3. *
SCHREIBER, J. "{}Contribution a la prèparation des esters a-alcoyloxalacétiques"{}. Bulletin de la Societe Chimique de France, 1952, páginas 61-64. Ver página 62, tabla II. *
TANAKA, K. et al. "{}Cinatrins, a novel family of phospholipase A2 inhibitors"{}. The Journal of Antibiotics, 1992, Volumen 45, páginas 50-55. Ver pagina 53, figura 4, compuesto 5b. *

Also Published As

Publication number Publication date
WO2009135978A1 (es) 2009-11-12
EP2287157A1 (en) 2011-02-23
CN102066350A (zh) 2011-05-18
JP2011523631A (ja) 2011-08-18
ES2328214A1 (es) 2009-11-10
AU2009245668A1 (en) 2009-11-12
US20110275838A1 (en) 2011-11-10
EP2287157A4 (en) 2011-08-31

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