ES2539637A1 - Nuevos antiiflamatorios basados en polifenoles del olivo - Google Patents

Nuevos antiiflamatorios basados en polifenoles del olivo Download PDF

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Publication number
ES2539637A1
ES2539637A1 ES201300916A ES201300916A ES2539637A1 ES 2539637 A1 ES2539637 A1 ES 2539637A1 ES 201300916 A ES201300916 A ES 201300916A ES 201300916 A ES201300916 A ES 201300916A ES 2539637 A1 ES2539637 A1 ES 2539637A1
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translation
machine
legally binding
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inflammatory drugs
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ES201300916A
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ES2539637B1 (es
Inventor
Jose María FERNÁNDEZ BOLAÑOS
Inés MAYA CASTILLA
Alejandro GONZÁLEZ BENJUMEA
María Ángeles LÓPEZ GARCÍA
Catalina ALARCÓN DE LA LASTRA ROMERO
Isabel VILLEGAS LAMA
Susana SÁNCHEZ FIDALGO
Marina APARICIO SOTO
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Universidad de Sevilla
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Universidad de Sevilla
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Priority to ES201300916A priority Critical patent/ES2539637B1/es
Priority to PCT/ES2014/000154 priority patent/WO2015044470A1/es
Publication of ES2539637A1 publication Critical patent/ES2539637A1/es
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/21—Acetic acid esters of hydroxy compounds with more than three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emergency Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Oncology (AREA)
  • Rheumatology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Nutrition Science (AREA)
  • Obesity (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

El objeto de la invención se centra en la síntesis por dos rutas alternativas del (3,4-dihidroxifenil)glicol (6), producto natural presente en el olivo, y en la síntesis de (3,4-dihidroxifenil)diacilglicoles (12). Tanto (6) como (12) son útiles como antiinflamatorios no esteroideos. De igual manera, los alcanoatos de hidroxitirosilo y diversos tioderivados del hidroxitirsol poseen propiedades antiinflamatorias. Por último, el acetato de hidroxitirosilo reduce el daño provocado en el colon de ratones en un modelo de colitis aguda inducida por dextrano sulfato sódico (DSS).

Description

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ES201300916A 2013-09-24 2013-09-24 Nuevos antiiflamatorios basados en polifenoles del olivo Active ES2539637B1 (es)

Priority Applications (2)

Application Number Priority Date Filing Date Title
ES201300916A ES2539637B1 (es) 2013-09-24 2013-09-24 Nuevos antiiflamatorios basados en polifenoles del olivo
PCT/ES2014/000154 WO2015044470A1 (es) 2013-09-24 2014-09-24 Nuevos antiinflamatorios basados en polifenoles del olivo

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES201300916A ES2539637B1 (es) 2013-09-24 2013-09-24 Nuevos antiiflamatorios basados en polifenoles del olivo

Publications (2)

Publication Number Publication Date
ES2539637A1 true ES2539637A1 (es) 2015-07-02
ES2539637B1 ES2539637B1 (es) 2016-02-05

Family

ID=52742115

Family Applications (1)

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ES201300916A Active ES2539637B1 (es) 2013-09-24 2013-09-24 Nuevos antiiflamatorios basados en polifenoles del olivo

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ES (1) ES2539637B1 (es)
WO (1) WO2015044470A1 (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115181084A (zh) * 2022-08-04 2022-10-14 中国药科大学 一类瑞香素衍生物的合成工艺优化及药理活性研究

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200308105A1 (en) * 2016-03-31 2020-10-01 Fujifilm Toyama Chemical Co., Ltd. Novel method for producing hydroxamic acid derivative, and intermediate therefor

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2377510A1 (en) * 2008-12-19 2011-10-19 Consejo Superior de Investigaciones Científicas (CSIC) Method for purifying 3,4-dihydroxyphenylglycol (dhpg) from plant products
ES2392915A1 (es) * 2011-06-03 2012-12-14 Universidad De Sevilla Compuestos bioactivos polifenólicos conteniendo azufre o selenio y sus usos
ES2395317A1 (es) * 2011-07-08 2013-02-11 Consejo Superior De Investigaciones Cientificas (Csic) Procedimiento para la obtención de extracto de hidroxitirosol, extracto mezcla de hidroxitirosol y 3,4-dihidroxifenilglicol, y extracto de acetato de hidroxitirosilo, a partir de subproductos del olivo y su purificación.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2377510A1 (en) * 2008-12-19 2011-10-19 Consejo Superior de Investigaciones Científicas (CSIC) Method for purifying 3,4-dihydroxyphenylglycol (dhpg) from plant products
ES2392915A1 (es) * 2011-06-03 2012-12-14 Universidad De Sevilla Compuestos bioactivos polifenólicos conteniendo azufre o selenio y sus usos
ES2395317A1 (es) * 2011-07-08 2013-02-11 Consejo Superior De Investigaciones Cientificas (Csic) Procedimiento para la obtención de extracto de hidroxitirosol, extracto mezcla de hidroxitirosol y 3,4-dihidroxifenilglicol, y extracto de acetato de hidroxitirosilo, a partir de subproductos del olivo y su purificación.

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
B. ROOS et al., ¿Anti-platelet effects of olive oil extract: in vitro functional and proteomic studies¿, European Journal of Nutrition, 2011, vol. 50, páginas 553-562 *
J. D. BENIGNI et al., ¿The synthesis of two new metabolites of catecholamines: 3,4-dihydroxyphenylethyleneglycol and 4-hydroxy-3-methoxyphenylethyleneglycol¿, Journal of Medicinal Chemistry, 1963, vol. 6, nº 5, páginas 607-608, ver Esquema *
M. H. HOLSHOUSER et al., ¿Facile synthesis of glycol metabolites of phenethylamine drugs¿, Journal of Pharmaceutical Sciences, 1986, vol. 75, nº 6, páginas 619-621, ver Esquema 1 *
T. R. WEBB, ¿A simple synthesis of potassium 3-methoxy-4-hydrophenylethyleneglycol-4-sulfate¿, Synthesis, 1984, vol. 3, páginas 213-214, ver Esquema, compuesto 6 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115181084A (zh) * 2022-08-04 2022-10-14 中国药科大学 一类瑞香素衍生物的合成工艺优化及药理活性研究

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ES2539637B1 (es) 2016-02-05

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