CN101506196B - 能够抑制ubc13-uev相互作用的化合物、药物组合物及治疗用途 - Google Patents

能够抑制ubc13-uev相互作用的化合物、药物组合物及治疗用途 Download PDF

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CN101506196B
CN101506196B CN2007800313305A CN200780031330A CN101506196B CN 101506196 B CN101506196 B CN 101506196B CN 2007800313305 A CN2007800313305 A CN 2007800313305A CN 200780031330 A CN200780031330 A CN 200780031330A CN 101506196 B CN101506196 B CN 101506196B
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ubc13
dimethylformamide
ethyl
cancer
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CN101506196A (zh
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蒂莫西·汤姆森奥卡图
约翰娜·舍佩尔西格蒙德
安赫尔·梅塞盖尔佩普克
安赫尔·拉米雷斯奥蒂斯
格洛利亚·圣克里门斯佩里茨德罗萨斯
伊莎贝尔·麦斯普麦斯普
亚历杭德拉·莫雷费尔南德斯
多明戈·冈萨雷斯鲁伊斯
安东尼奥·莫雷亚莱德莱昂
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Consejo Superior de Investigaciones Cientificas CSIC
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P37/08—Antiallergic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings

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  • Health & Medical Sciences (AREA)
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  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CN2007800313305A 2006-07-20 2007-03-07 能够抑制ubc13-uev相互作用的化合物、药物组合物及治疗用途 Expired - Fee Related CN101506196B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ESP200601933 2006-07-20
ES200601933A ES2293834B1 (es) 2006-07-20 2006-07-20 Compuesto con actividad inhibidora de las interacciones ubc13-uev, composiciones farmaceuticas que lo comprenden y sus aplicaciones terapeuticas.
PCT/ES2007/000120 WO2008009758A1 (es) 2006-07-20 2007-03-07 Compuestos con actividad inhibidora de las interacciones ubc13-uev, composiciones farmacéuticas y aplicaciones terapéuticas

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CN101506196A CN101506196A (zh) 2009-08-12
CN101506196B true CN101506196B (zh) 2013-11-20

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US (2) US8252786B2 (enExample)
EP (1) EP2045251B1 (enExample)
JP (1) JP5203363B2 (enExample)
CN (1) CN101506196B (enExample)
AU (1) AU2007275073B2 (enExample)
CA (1) CA2658327C (enExample)
ES (1) ES2293834B1 (enExample)
MX (1) MX2009000672A (enExample)
WO (1) WO2008009758A1 (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2611944A1 (en) 2005-06-15 2006-12-28 Massachusetts Institute Of Technology Amine-containing lipids and uses thereof
JP6087504B2 (ja) 2008-11-07 2017-03-01 マサチューセッツ インスティテュート オブ テクノロジー アミノアルコールリピドイドおよびその使用
CA2769408C (en) * 2009-07-30 2017-09-05 Laboratorios Salvat, S.A. Apaf-1 inhibitor compounds
CA2782676C (en) 2009-12-01 2021-06-15 Shire Human Genetic Therapies, Inc. Pharmaceutical compositions for intracellular delivery of nucleic acids and proteins and uses thereof for treatment of ureca cycle metabolic disorders
EP2609135A4 (en) 2010-08-26 2015-05-20 Massachusetts Inst Technology POLY (BETA AMINO ALCOHOLS), THEIR PREPARATION AND USES THEREOF
JP2014511839A (ja) * 2011-03-23 2014-05-19 インディアナ・ユニバーシティ・リサーチ・アンド・テクノロジー・コーポレイション 抗癌治療薬
PL2691443T3 (pl) 2011-03-28 2021-08-30 Massachusetts Institute Of Technology Sprzężone lipomery i ich zastosowania
CA3107288A1 (en) 2011-06-08 2012-12-13 Translate Bio, Inc. Lipid nanoparticle compositions and methods for mrna delivery
EP4074694A1 (en) * 2011-10-27 2022-10-19 Massachusetts Institute Of Technology Amino acid-, peptide- an polypeptide-lipids, isomers, compositions, an uses thereof
US20130236504A1 (en) * 2012-03-06 2013-09-12 Medical University Of South Carolina Delivery System for Enhancing Drug Efficacy
EP2859102A4 (en) 2012-06-08 2016-05-11 Shire Human Genetic Therapies NUCLEASE RESISTANT POLYNUCLEOTIDES AND USES THEREOF
EP2882706A1 (en) 2012-08-13 2015-06-17 Massachusetts Institute of Technology Amine-containing lipidoids and uses thereof
MX365409B (es) 2013-03-14 2019-05-31 Shire Human Genetic Therapies Composiciones de ácido ribonucleico mensajero del regulador transmembrana de fibrosis quística y métodos y usos relacionados.
EA201591229A1 (ru) 2013-03-14 2016-01-29 Шир Хьюман Дженетик Терапис, Инк. Способы очистки матричной рнк
US9315472B2 (en) 2013-05-01 2016-04-19 Massachusetts Institute Of Technology 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof
MX2016005239A (es) 2013-10-22 2016-08-12 Shire Human Genetic Therapies Tratamiento con acido ribonucleico mensajero para la fenilcetonuria.
EP3060303B1 (en) 2013-10-22 2018-11-14 Translate Bio, Inc. Mrna therapy for argininosuccinate synthetase deficiency
EP3871696B1 (en) 2013-10-22 2025-03-19 Translate Bio, Inc. Lipid formulations for delivery of messenger rna
JP6295767B2 (ja) 2014-03-25 2018-03-20 富士通株式会社 スイッチ装置、情報処理システムおよびスイッチ装置の制御方法
KR20250005450A (ko) 2014-04-25 2025-01-09 샤이어 휴먼 지네틱 테라피즈 인크. 메신저 rna 의 정제 방법
BR112016027705A2 (pt) 2014-05-30 2018-01-30 Shire Human Genetic Therapies lipídios biodegradáveis para distribuição de ácidos nucleicos
PE20171238A1 (es) 2014-06-24 2017-08-24 Shire Human Genetic Therapies Composiciones enriquecidas estereoquimicamente para administracion de acidos nucleicos
US9840479B2 (en) 2014-07-02 2017-12-12 Massachusetts Institute Of Technology Polyamine-fatty acid derived lipidoids and uses thereof
EP4248988A3 (en) 2015-06-19 2023-11-29 Massachusetts Institute of Technology Alkenyl substituted 2,5-piperazinediones and their use in compositions for delivering an agent to a subject or cell
EA201991747A1 (ru) 2017-02-27 2020-06-04 Транслейт Био, Инк. НОВАЯ КОДОН-ОПТИМИЗИРОВАННАЯ мРНК CFTR
CA3063531A1 (en) 2017-05-16 2018-11-22 Translate Bio, Inc. Treatment of cystic fibrosis by delivery of codon-optimized mrna encoding cftr
EP3841208A1 (en) 2018-08-24 2021-06-30 Translate Bio, Inc. Methods for purification of messenger rna
MX2021005969A (es) 2018-11-21 2021-09-14 Translate Bio Inc Tratamiento de la fibrosis quística mediante el suministro de arnm que codifica cftr nebulizado.
WO2020252487A1 (en) * 2019-06-14 2020-12-17 Children's Hospital Medical Center Rational therapeutic targeting of oncogenic immune signaling states in myeloid malignancies via the ubiquitin conjugating enzyme ube2n
KR20220017075A (ko) 2020-08-04 2022-02-11 삼성전자주식회사 홈 화면을 복원하는 방법 및 이를 적용한 전자 장치
US20250214975A1 (en) * 2022-05-19 2025-07-03 Ohio State Innovation Foundation Peptidyl flavor modifiers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002011750A2 (en) * 2000-08-08 2002-02-14 The Government Of The United States Of America, As Represented By The Secretary Of Health And Human Prevention of beta-amyloid neurotoxicity by blockade of the ubiquitin-proteasome proteolytic pathway
WO2002028885A1 (es) * 2000-10-06 2002-04-11 Diverdrugs, S.L. Trímeros de n-alquilglicina capaces de proteger a neuronas contra agresiones excitotóxicas, y composiciones que los contienen
US20030069189A1 (en) * 1997-02-15 2003-04-10 Millennium Pharmaceuticals, Inc. Treatment of infarcts

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4234295A1 (de) * 1992-10-12 1994-04-14 Thomae Gmbh Dr K Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
TW200538149A (en) 2004-05-20 2005-12-01 Telik Inc Sensitization to another anticancer therapy and/or amelioration of a side effect of another anticancer therapy by treatment with a GST-activated anticancer compound
ES2296484B1 (es) * 2005-11-23 2009-04-01 Fundacion De La Comunidad Valenciana Centro De Investigacion Principe Felipe (90%) Composicion farmaceutica para inhibir la apoptosis.

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030069189A1 (en) * 1997-02-15 2003-04-10 Millennium Pharmaceuticals, Inc. Treatment of infarcts
WO2002011750A2 (en) * 2000-08-08 2002-02-14 The Government Of The United States Of America, As Represented By The Secretary Of Health And Human Prevention of beta-amyloid neurotoxicity by blockade of the ubiquitin-proteasome proteolytic pathway
WO2002028885A1 (es) * 2000-10-06 2002-04-11 Diverdrugs, S.L. Trímeros de n-alquilglicina capaces de proteger a neuronas contra agresiones excitotóxicas, y composiciones que los contienen

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Isabel Masip et al.,.Design and synthesis of an optimized positional scanning library of peptoids: identification of novel multidrug resistance reversal agents.《Bioorganic & Medicinal Chemistry》.2005,第13卷第1923-1929页. *
Isabel Masip et al.,.Synthesis of a Library of 3-Oxopiperazinium and Perhydro-3-oxo-1,4-diazepinium Derivatives and Identification of Bioactive Compounds.《Journal of Combinatorial Chemistry》.2003,第6卷(第1期),第135-141页. *

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CA2658327C (en) 2013-12-03
EP2045251A1 (en) 2009-04-08
CA2658327A1 (en) 2008-01-24
ES2293834A1 (es) 2008-03-16
US20130237529A1 (en) 2013-09-12
EP2045251B1 (en) 2015-11-18
EP2045251A4 (en) 2010-12-01
CN101506196A (zh) 2009-08-12
US8252786B2 (en) 2012-08-28
JP2009544600A (ja) 2009-12-17
AU2007275073B2 (en) 2012-06-07
JP5203363B2 (ja) 2013-06-05
ES2293834B1 (es) 2009-02-16
US8785430B2 (en) 2014-07-22
AU2007275073A1 (en) 2008-01-24
WO2008009758A1 (es) 2008-01-24
US20110160189A1 (en) 2011-06-30
MX2009000672A (es) 2009-02-04

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