ES2525503A1 - Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica - Google Patents

Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica Download PDF

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ES2525503A1
ES2525503A1 ES201330738A ES201330738A ES2525503A1 ES 2525503 A1 ES2525503 A1 ES 2525503A1 ES 201330738 A ES201330738 A ES 201330738A ES 201330738 A ES201330738 A ES 201330738A ES 2525503 A1 ES2525503 A1 ES 2525503A1
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ischaemia
alzheimer
treatment
lateral sclerosis
amyotrophic lateral
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ES2525503B1 (es
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José Luis Marco Contelles
Alberto ALCÁZAR GONZÁLEZ
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FUNDACION PARA LA INVESTIGACION BIOMEDICA DEL HOSP
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Consejo Superior de Investigaciones Cientificas CSIC
Fundacion para la Investigacion Biomedica del Hospital Universitario Ramon Y Cajal
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Priority to ES201330738A priority Critical patent/ES2525503B1/es
Priority to ITRM2014U000075U priority patent/ITRM20140075U1/it
Priority to AU2014270269A priority patent/AU2014270269B2/en
Priority to TR2019/08363T priority patent/TR201908363T4/tr
Priority to PT14801897T priority patent/PT3000469T/pt
Priority to RU2015154103A priority patent/RU2668514C2/ru
Priority to PL14801897T priority patent/PL3000469T3/pl
Priority to CA2913182A priority patent/CA2913182A1/en
Priority to CN201480035659.9A priority patent/CN105377264B/zh
Priority to US14/892,755 priority patent/US10071106B2/en
Priority to ES14801897T priority patent/ES2730963T3/es
Priority to EP14801897.1A priority patent/EP3000469B1/en
Priority to MX2015016077A priority patent/MX370402B/es
Priority to PCT/ES2014/070421 priority patent/WO2014188046A1/es
Priority to JP2016514450A priority patent/JP6424212B2/ja
Priority to BR112015029302A priority patent/BR112015029302A2/pt
Publication of ES2525503A1 publication Critical patent/ES2525503A1/es
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Publication of ES2525503B1 publication Critical patent/ES2525503B1/es
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    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
    • A61K38/46—Hydrolases (3)
    • A61K38/48—Hydrolases (3) acting on peptide bonds (3.4)
    • A61K38/482—Serine endopeptidases (3.4.21)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
    • G01N33/502—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics for testing non-proliferative effects
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
    • G01N33/5044—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics involving specific cell types
    • G01N33/5058—Neurological cells
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    • C12Y—ENZYMES
    • C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
    • C12Y304/21—Serine endopeptidases (3.4.21)
    • C12Y304/21068—Tissue plasminogen activator (3.4.21.68), i.e. tPA

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Abstract

Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica. Uso y preparación de esteronitronas con alta permeabilidad a la barrera hematoencefálica, capacidad antioxidante y neuroprotectora, como potenciales fármacos para el tratamiento del ictus o accidente cerebrovascular, enfermedades de Alzheimer, Parkinson y esclerosis lateral amiotrófica.

Description

imagen1
imagen2
imagen3
imagen4
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imagen6
La neuroprotección inducida por la colesteronitrona F2 se comparó con la de citicolina a 5 μM, lo que resultó en una neuroprotección significativamente más alta que la observada para citicolina (Tabla 1).
Tabla 1. Efecto neuroprotector de las colesteronitronas F2 y F3 en cultivos neuronales en condiciones de DOG.
Colesteronitrona
Concentración (M) Neuroprotección (%)
F2
0,1 9,6  0,5
0,5
49,3  3,6
1,0
54,3  1,3 *
5,0
80,7 ? 2,7 ***
10
47,2  1,4
50
< 0
100
< 0
F3
0,5 < 0
1,0
18,8  1,1
5,0
21,7  1,2
10
0,8  0,07
citicolina
100 50,2  1,26
Por el contrario, la colesteronitrona F3 no mostró una significativa capacidad neuroprotectora.
Para evaluar el poder neuroprotector de las colesteronitronas F2 y F3 frente a un daño isquémico en neuronas cultivadas y simular unas condiciones de reperfusión a largo plazo, los cultivos se expusieron a DOG durante 4 h, y entonces, las células se sometieron a reperfusión durante 5 d (R5d).
Las colesteronitronas F2 y F3 (a concentraciones de 1,0 y 5,0 M) se añadieron al principio del período de reperfusión y después de 48 h de reperfusión, para así evaluar su poder neuroprotector a largo plazo, utilizando de nuevo la molécula de referencia citicolina, de acuerdo con el protocolo del MTT (ver más arriba).
El experimento R5d indujo una más que notable disminución de la viabilidad celular (77,7%; p < 0,0001 versus 100% del control, test de la t de muestra única) (Figura 2). Citicolina, ensayada a una concentración de 100 μM, no produjo neuroprotección alguna en el experimento R5d tanto cuando se añadió al inicio de la reperfusión (barra sólida) o después de 48 h de reperfusión (barra rallada) (76,0 y 74,6%, respectivamente; ANOVA, p = 0,786).
8
imagen7
imagen8

Claims (1)

  1. imagen1
    imagen2
ES201330738A 2013-05-22 2013-05-22 Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica Active ES2525503B1 (es)

Priority Applications (16)

Application Number Priority Date Filing Date Title
ES201330738A ES2525503B1 (es) 2013-05-22 2013-05-22 Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica
ITRM2014U000075U ITRM20140075U1 (it) 2013-05-22 2014-05-16 Insieme di specchio retrovisore con videocamera per veicoli.
EP14801897.1A EP3000469B1 (en) 2013-05-22 2014-05-22 Steroidal nitrones for the treatment and prevention of a cerebral stroke or ischaemia, alzheimer and parkinson disease and amyotrophic lateral sclerosis
PT14801897T PT3000469T (pt) 2013-05-22 2014-05-22 Nitronas esteroides para o tratamento e prevenção de um acidente vascular cerebral ou isquemia cerebral, doença de alzheimer e de parkinson e esclerose lateral amiotrófica
RU2015154103A RU2668514C2 (ru) 2013-05-22 2014-05-22 Нитроны стероидов для лечения и предотвращения инсульта или ишемии головного мога, болезни Альцгеймера, болезни Паркинсона и бокового амиотрофического склероза
PL14801897T PL3000469T3 (pl) 2013-05-22 2014-05-22 Steroidowe nitrony do leczenia i zapobiegania udarowi lub niedokrwieniu mózgu, chorobie alzheimera i parkinsona oraz stwardnieniu zanikowemu bocznemu
CA2913182A CA2913182A1 (en) 2013-05-22 2014-05-22 Steroidal nitrones for the treatment and prevention of a cerebral stroke or ischaemia, alzheimer's and parkinson's disease and amyotrophic lateral sclerosis
CN201480035659.9A CN105377264B (zh) 2013-05-22 2014-05-22 用于治疗和预防脑卒中或缺血、阿尔茨海默病和帕金森病和肌萎缩性侧索硬化的甾族硝酮
AU2014270269A AU2014270269B2 (en) 2013-05-22 2014-05-22 Steroidal nitrones for the treatment and prevention of a cerebral stroke or ischaemia, Alzheimer and Parkinson disease and amyotrophic lateral sclerosis
ES14801897T ES2730963T3 (es) 2013-05-22 2014-05-22 Esteronitronas para el tratamiento y prevención del ictus o isquemia cerebral, enfermedad de Alzheimer y Parkinson y esclerosis lateral amiotrófica
TR2019/08363T TR201908363T4 (tr) 2013-05-22 2014-05-22 Bir serebral felcin veya iskeminin, alzheımer ve parkinson hastalığının ve amiyotrofik lateral sklerozun tedavisine ve önlenmesine yönelik steroid nitronlar.
MX2015016077A MX370402B (es) 2013-05-22 2014-05-22 Esteronitronas para el tratamiento y prevencion del ictus o isquemia cerebral, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrofica.
PCT/ES2014/070421 WO2014188046A1 (es) 2013-05-22 2014-05-22 Esteronitronas para el tratamiento y prevención del ictus o isquemia cerebral, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica
JP2016514450A JP6424212B2 (ja) 2013-05-22 2014-05-22 脳卒中または虚血、アルツハイマー病およびパーキンソン病および筋萎縮性側索硬化症の治療および予防のためのステロイド性ニトロン
BR112015029302A BR112015029302A2 (pt) 2013-05-22 2014-05-22 uso de uma nitrona esteroidal de fórmula ia-c; composição; uso de uma composição; método para identificar e avaliar compostos tendo alto poder neuroprotetor e envolvendo um possível tratamento efetivo para doenças neurológicas; e método para a obtenção de compostos
US14/892,755 US10071106B2 (en) 2013-05-22 2014-05-22 Steroidal nitrones for the treatment and prevention of a cerebral stroke or ischaemia, alzheimer and parkinson disease and amyotrophic lateral sclerosis

Applications Claiming Priority (1)

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ES201330738A ES2525503B1 (es) 2013-05-22 2013-05-22 Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica

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ES2525503A1 true ES2525503A1 (es) 2014-12-23
ES2525503B1 ES2525503B1 (es) 2015-10-15

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ES201330738A Active ES2525503B1 (es) 2013-05-22 2013-05-22 Uso de esteronitronas para el tratamiento y prevención del ictus o accidente cerebrovascular, enfermedades de alzheimer, parkinson y esclerosis lateral amiotrófica
ES14801897T Active ES2730963T3 (es) 2013-05-22 2014-05-22 Esteronitronas para el tratamiento y prevención del ictus o isquemia cerebral, enfermedad de Alzheimer y Parkinson y esclerosis lateral amiotrófica

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US (1) US10071106B2 (es)
EP (1) EP3000469B1 (es)
JP (1) JP6424212B2 (es)
CN (1) CN105377264B (es)
AU (1) AU2014270269B2 (es)
BR (1) BR112015029302A2 (es)
CA (1) CA2913182A1 (es)
ES (2) ES2525503B1 (es)
IT (1) ITRM20140075U1 (es)
MX (1) MX370402B (es)
PL (1) PL3000469T3 (es)
PT (1) PT3000469T (es)
RU (1) RU2668514C2 (es)
TR (1) TR201908363T4 (es)
WO (1) WO2014188046A1 (es)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3875095A1 (en) * 2020-03-05 2021-09-08 Isquaemia Biotech, S.L. Steroidal nitrone for the treatment and/or prevention of a cerebral stroke or ischaemia
CN112494491B (zh) * 2020-12-14 2022-04-01 东北大学 克班宁在制备预防或治疗神经退行性疾病的药物中的用途
CN113304129B (zh) * 2021-06-16 2022-11-08 温州医科大学附属第二医院（温州医科大学附属育英儿童医院） 单烯酮类单羰基姜黄素类似物在制备抗氧化药物的应用

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* Cited by examiner, † Cited by third party
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SU491625A1 (ru) * 1973-11-15 1975-11-15 Институт Органической Химии Им.Н.Д. Зелинского Способ получени изоксазолидино-(16альфа,17альфа-d)-стероидов
US20070166299A1 (en) * 2005-03-02 2007-07-19 The Regents Of The University Of California Treatment for embolic stroke
ES2395803B1 (es) * 2011-08-01 2013-12-19 Consejo Superior De Investigaciones Científicas (Csic) - 80% Quinolilnitronas

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EP3000469B1 (en) 2019-03-13
RU2015154103A (ru) 2017-06-27
ITRM20140075U1 (it) 2015-11-16
US20160089382A1 (en) 2016-03-31
US10071106B2 (en) 2018-09-11
ES2525503B1 (es) 2015-10-15
RU2668514C2 (ru) 2018-10-01
JP2016524610A (ja) 2016-08-18
CA2913182A1 (en) 2014-11-27
AU2014270269A1 (en) 2015-12-10
TR201908363T4 (tr) 2019-06-21
ES2730963T3 (es) 2019-11-13
CN105377264A (zh) 2016-03-02
EP3000469A1 (en) 2016-03-30
JP6424212B2 (ja) 2018-11-14
CN105377264B (zh) 2019-02-15
AU2014270269B2 (en) 2018-05-17
EP3000469A4 (en) 2017-01-25
PT3000469T (pt) 2019-06-14
MX370402B (es) 2019-12-11
MX2015016077A (es) 2016-03-21
BR112015029302A2 (pt) 2017-07-25
WO2014188046A1 (es) 2014-11-27
PL3000469T3 (pl) 2019-10-31

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