BR0207141A - Propriedades antitumorais do 1,5-bis(4-hidroxi-3-metoxifenil)-penta-1,4-dien-3-ona e derivados e seu procedimento de obtenção - Google Patents

Propriedades antitumorais do 1,5-bis(4-hidroxi-3-metoxifenil)-penta-1,4-dien-3-ona e derivados e seu procedimento de obtenção

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Publication number
BR0207141A
BR0207141A BR0207141-0A BRPI0207141A BR0207141A BR 0207141 A BR0207141 A BR 0207141A BR PI0207141 A BRPI0207141 A BR PI0207141A BR 0207141 A BR0207141 A BR 0207141A
Authority
BR
Brazil
Prior art keywords
derivatives
dien
penta
bis
hydroxy
Prior art date
Application number
BR0207141-0A
Other languages
English (en)
Inventor
Jose Agustin Quincoces Suarez
Klaus Peseke
Marcus Kordian
Joao Ernesto De Carvalho
Luciana Konecny Kohn
Maria Aparecida Antonio
Heloiza Brunhari
Original Assignee
Jose Agustin Quincoces Suarez
Fundacao De Amparo A Pesquisa
Academia Paulista Anchieta S C
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
Application filed by Jose Agustin Quincoces Suarez, Fundacao De Amparo A Pesquisa, Academia Paulista Anchieta S C filed Critical Jose Agustin Quincoces Suarez
Priority to BR0207141-0 priority Critical patent/BRPI0207141B8/pt
Priority to EP03773364.9A priority patent/EP1572614B1/en
Priority to PT37733649T priority patent/PT1572614E/pt
Priority to JP2004554088A priority patent/JP2006508149A/ja
Priority to ES03773364.9T priority patent/ES2464268T3/es
Priority to PCT/BR2003/000177 priority patent/WO2004047716A2/en
Priority to AU2003283092A priority patent/AU2003283092A1/en
Priority to US10/536,667 priority patent/US7432401B2/en
Publication of BR0207141A publication Critical patent/BR0207141A/pt
Publication of BRPI0207141B1 publication Critical patent/BRPI0207141B1/pt
Publication of BRPI0207141B8 publication Critical patent/BRPI0207141B8/pt

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • C07C49/248—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

Abstract

"PROPRIEDADES ANTITUMORAIS DO 1,5-BIS(4-HIDROXI-3-METOXIFENIL)-PENTA-1,4-DIEN-3-ONA E DERIVADOS E SEU PROCEDIMENTO DE OBTENçãO". A presente patente de invenção relata as propriedades antitumorais do 1,5-Bis(4-hidroxi-3-metoxi-fenil)-penta-1,4-dien-3-ona e derivados e seu procedimento de obtenção: a amostra denominada composto 37 foi obtida com alto rendimento e pureza através da técnica ultrasónica apresentando atividade citostática (inibição do crescimento) nas concentrações avaliadas e atividade citocida (morte celular) a partir da concentração de 0,25 <109>g / mL frente a nove diferentes tipos de câncer humano. Este composto possui uma DL~ 50~, igual a 8,54g/Kg. Isto significa que este produto pode considerar-se como praticamente atóxico, sendo que a Doxorrubicina, medicamento anticancerígeno usado como referência em todos estes testes e um produto extremadamente tóxico (DL~ 50~ de 20mg/Kg) e não inibe o crescimento da linhagem celular Mama NCI-ADR (linhagem celular que expressa o fenótipo de resistência a múltiplas drogas), portanto nosso produto se mostrou com ação fortemente citostática. Os outros derivados apresentaram também forte ação citostática e citocida principalmente o composto denominado por EHB1.
BR0207141-0 2002-11-28 2002-11-28 processo para preparar compostos, uso de compostos, composição farmacêutica e método para tratamento de câncer BRPI0207141B8 (pt)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BR0207141-0 BRPI0207141B8 (pt) 2002-11-28 2002-11-28 processo para preparar compostos, uso de compostos, composição farmacêutica e método para tratamento de câncer
EP03773364.9A EP1572614B1 (en) 2002-11-28 2003-11-28 Method for the preparation of 1,5-bis(4-hydroxy-3-metoxy-phenyl)-penta-1,4-dien-3-one
PT37733649T PT1572614E (pt) 2002-11-28 2003-11-28 Processo para a preparação de 1,5-bis(4-hidroxi-3-metoxifenil)- penta-1,4-dien-3-ona
JP2004554088A JP2006508149A (ja) 2002-11-28 2003-11-28 抗腫瘍特性を有する１，５−ビス（４−ヒドロキシ−３−メトキシフェニル）−ペンタ−１，４−ジエン−３−オンおよび誘導体の新規な製造方法
ES03773364.9T ES2464268T3 (es) 2002-11-28 2003-11-28 Procedimiento para la preparaci�n de 1,5-bis(4-hidroxi-3-metoxi-fenil)-penta-1,4-dien-3-ona
PCT/BR2003/000177 WO2004047716A2 (en) 2002-11-28 2003-11-28 New method for the preparation of 1,5-bis(4-hydroxy-3-metoxy-phenyl)-penta-1,4-dien-3-one and derivatives with antitumoral properties
AU2003283092A AU2003283092A1 (en) 2002-11-28 2003-11-28 New method for the preparation of 1,5-bis(4-hydroxy-3-metoxy-phenyl)-penta-1,4-dien-3-one and derivatives with antitumoral properties
US10/536,667 US7432401B2 (en) 2002-11-28 2003-11-28 Method for the preparation of 1,5-bis(4-hydroxy-3-metoxy-phenyl)-penta-1,4-dien-3-one and derivatives with antitumoral properties

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BR0207141-0 BRPI0207141B8 (pt) 2002-11-28 2002-11-28 processo para preparar compostos, uso de compostos, composição farmacêutica e método para tratamento de câncer

Publications (3)

Publication Number Publication Date
BR0207141A true BR0207141A (pt) 2004-06-29
BRPI0207141B1 BRPI0207141B1 (pt) 2019-04-16
BRPI0207141B8 BRPI0207141B8 (pt) 2021-05-25

Family

ID=67251474

Family Applications (1)

Application Number Title Priority Date Filing Date
BR0207141-0 BRPI0207141B8 (pt) 2002-11-28 2002-11-28 processo para preparar compostos, uso de compostos, composição farmacêutica e método para tratamento de câncer

Country Status (8)

Country Link
US (1) US7432401B2 (pt)
EP (1) EP1572614B1 (pt)
JP (1) JP2006508149A (pt)
AU (1) AU2003283092A1 (pt)
BR (1) BRPI0207141B8 (pt)
ES (1) ES2464268T3 (pt)
PT (1) PT1572614E (pt)
WO (1) WO2004047716A2 (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8841326B2 (en) 2004-02-12 2014-09-23 Stc.Unm Therapeutic curcumin derivatives
BRPI0602640B8 (pt) * 2006-07-06 2021-05-25 Anhanguera Educacional Ltda métodos de obtenção de penta-1,4-dien-3-onas e de cicloexanonas substituídas e derivados com propriedades antitumorais e antiparasitárias, processo para preparar 1,5-bis-(aril)-penta-1,4-dien-3-onas alquiladas e aciladas, processo para preparar 4-nitro-3,5-diaril-cicloexanonas substituídas, processo para preparar 2,6-dibenzilideno-4-nitro-3,5-diaril-cicloexanonas substituídas, processo para preparar uma mistura formada por quantidades determinadas dos compostos (1,5-bis(4-hidróxi-3-metóxi-fenil)penta-1,4-dien-3-ona) e (1,5-bis(3-metóxi-4-acetóxi-fenil)penta-1,4-dien-3-ona), compostos e seus usos, composição farmacêutica, método terapêutico para tratamento dos cânceres e composição sinérgica
CN103922911A (zh) * 2014-04-17 2014-07-16 上海应用技术学院 一种(1e,4e)-1,5-二(邻溴间甲氧基苯基)-1,4-戊二烯酮化合物及合成方法
CN114478256B (zh) * 2022-01-26 2024-02-23 安徽理工大学环境友好材料与职业健康研究院(芜湖) 一种新型姜黄素衍生物的制备方法及其抗肝癌的应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4521629A (en) * 1984-06-29 1985-06-04 American Cyanamid Company Method for the preparation of 1,5-bis-aryl-1,4-pentadien-3-ones
DE69028136T2 (de) * 1989-05-17 1997-01-23 Shionogi Seiyaku Kk Alkoxyiminoacetamid-Derivate und ihre Verwendung als pilztötendes Mittel
JP2856838B2 (ja) * 1990-04-30 1999-02-10 株式会社クラレ ステロイド誘導体の製造方法
JP2921104B2 (ja) * 1990-11-15 1999-07-19 東亞合成株式会社 β，γ―不飽和アルケニル基置換フェノール類の製造方法
JPH07215957A (ja) * 1994-02-03 1995-08-15 Takeda Chem Ind Ltd グリシジルエーテル類の製造法及びそのための連続製造装置
US6852248B1 (en) * 1999-04-02 2005-02-08 Hrl Laboratories, Llc Dopants for liquid-crystal devices
US6664272B2 (en) * 1999-12-03 2003-12-16 Emory University Curcumin analogs with anti-tumor and anti-angiogenic properties

Also Published As

Publication number Publication date
ES2464268T3 (es) 2014-06-02
AU2003283092A1 (en) 2004-06-18
BRPI0207141B8 (pt) 2021-05-25
BRPI0207141B1 (pt) 2019-04-16
EP1572614B1 (en) 2013-12-25
JP2006508149A (ja) 2006-03-09
WO2004047716A2 (en) 2004-06-10
US7432401B2 (en) 2008-10-07
AU2003283092A8 (en) 2004-06-18
WO2004047716A3 (en) 2004-08-19
EP1572614A2 (en) 2005-09-14
US20060128997A1 (en) 2006-06-15
PT1572614E (pt) 2014-04-03

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Legal Events

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B06F Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]
B07D Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]
B25C Requirement related to requested transfer of rights

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) , FUNDACAO D

B25L Entry of change of name and/or headquarter and transfer of application, patent and certificate of addition of invention: publication cancelled

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) , FUNDACAO D

B25C Requirement related to requested transfer of rights

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) , FUNDACAO D

B25B Requested transfer of rights rejected

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) , FUNDACAO D

B07E Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette]
B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B25C Requirement related to requested transfer of rights

Owner name: JOSA AGUSTA-N QUINCOCES SUA REZ (BR/SP) ; FUNDAA

B25L Entry of change of name and/or headquarter and transfer of application, patent and certificate of addition of invention: publication cancelled

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) ; FUNDACAO D

Free format text: ANULADA A PUBLICACAO CODIGO 25.3 NA RPI NO 2484 DE 14/08/2018 POR TER SIDO INDEVIDA.

B25D Requested change of name of applicant approved

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) ; FUNDACAO D

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) ; FUNDACAO DE AMPARO A PESQUISA DO ESTADO DE SAO PAULO (BR/SP) ; ACADEMIA PAULISTA ANCHIETA LTDA. (BR/SP)

B25A Requested transfer of rights approved

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) ; FUNDACAO D

Owner name: JOSE AGUSTIN QUINCOCES SUAREZ (BR/SP) ; FUNDACAO DE AMPARO A PESQUISA DO ESTADO DE SAO PAULO (BR/SP) ; ANHANGUERA EDUCACIONAL LTDA. (BR/SP)

B09A Decision: intention to grant [chapter 9.1 patent gazette]
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