WO2002081491A3 - Nouveaux derives de genisteine et preparations pharmaceutiques les contenant - Google Patents
Nouveaux derives de genisteine et preparations pharmaceutiques les contenant Download PDFInfo
- Publication number
- WO2002081491A3 WO2002081491A3 PCT/PL2002/000029 PL0200029W WO02081491A3 WO 2002081491 A3 WO2002081491 A3 WO 2002081491A3 PL 0200029 W PL0200029 W PL 0200029W WO 02081491 A3 WO02081491 A3 WO 02081491A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- hydrogen atom
- aryl
- same
- pharmaceutical preparations
- Prior art date
Links
- 229930004065 genistein derivative Natural products 0.000 title abstract 2
- 150000002273 genistein derivatives Chemical class 0.000 title abstract 2
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- -1 alkyloaryl Chemical group 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 150000001720 carbohydrates Chemical group 0.000 abstract 1
- 230000002113 chemopreventative effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 150000002482 oligosaccharides Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
L'invention concerne des dérivés de génistéine représentés par la formule 1 dans laquelle R1 et R2 sont identiques ou différents et représentent indépendamment un atome d'hydrogène, alkyle, aryle, alkyloaryle, alkylcarbonyle, arylcarbonyle, chacun des groupes mentionnés ci-dessus pouvant être substitués dans une chaîne ou un noyau par des groupes amino, nitro ou nitrile, un groupe R5(R6)R7-Si dans lequel R5, R6 et R7 sont identiques ou différents et représentent un groupe C1-6 alkyle ou aryle, mono-, di- ou oligosaccharide, un groupe hydroxy au moins du groupe saccharide pouvant être substitué par un groupe acyle, alkyle, acyloxyalkyle ou aryle identique ou différent; R3 représente un atome d'hydrogène ou un groupe -COCH3; et R4 représente un atome d'hydrogène, un groupe -SO3H, SO3- ou -NH¿2? ou -NO2. L'invention concerne également leurs sels acceptables d'un point de vue pharmaceutique, présentant une activité antiproliférative et antitumorale. L'invention concerne enfin de nouveaux dérivés et des préparations pharmaceutiques les contenant, pouvant être utilisés dans le domaine de l'oncologie clinique et/ou la chimioprévention des néoplasmes.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PLP-346955 | 2001-04-09 | ||
PL346955A PL205635B1 (pl) | 2001-04-09 | 2001-04-09 | Nowe pochodne genisteiny i zawierające je środki farmaceutyczne |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002081491A2 WO2002081491A2 (fr) | 2002-10-17 |
WO2002081491A3 true WO2002081491A3 (fr) | 2004-02-26 |
Family
ID=20078583
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/PL2002/000029 WO2002081491A2 (fr) | 2001-04-09 | 2002-04-08 | Nouveaux derives de genisteine et preparations pharmaceutiques les contenant |
Country Status (2)
Country | Link |
---|---|
PL (1) | PL205635B1 (fr) |
WO (1) | WO2002081491A2 (fr) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1285586C (zh) * | 2003-05-15 | 2006-11-22 | 成都迪康药物研究所 | 鸢尾苷元的异黄酮类衍生物及其制备方法和以其为有效药用成分的抗病毒药物 |
WO2007001348A2 (fr) * | 2004-08-26 | 2007-01-04 | The Ohio State University Research Foundation | Isoflavones renfermant des heteroaryles utilisees comme inhibiteurs de l'aromatase |
CN104860913B (zh) * | 2008-12-11 | 2018-05-04 | 艾克赛特药品有限公司 | 染料木黄酮的晶型 |
PL399467A1 (pl) | 2012-06-08 | 2013-12-09 | 3G Therapeutics Inc. | Zastosowanie genisteiny do obnizania poziomu zwiazków organicznych spichrzanych w komórkach w leczeniu i/lub zapobieganiu lizosomalnych chorób spichrzeniowych (LChS) |
CN104974204B (zh) * | 2015-06-19 | 2017-12-19 | 武汉光谷人福生物医药有限公司 | 从广金钱草中提取分离黄酮氧苷类化合物单体的方法和系统 |
CN107652261B (zh) * | 2017-09-30 | 2020-08-07 | 桂林医学院 | 一种毛蕊异黄酮衍生物及其合成方法 |
WO2023212130A1 (fr) * | 2022-04-28 | 2023-11-02 | GreenStone Biosciences, Inc. | Traitement des effets cardiovasculaires indésirables de cannabinoïdes |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997029779A2 (fr) * | 1996-02-16 | 1997-08-21 | Regents Of The University Of Minnesota | Conjugues de egf-genisteine pour le traitement du cancer |
WO1997032872A1 (fr) * | 1996-03-05 | 1997-09-12 | Imperial College Of Science Technology And Medicine | Composes comportant un groupe sulfamate |
WO1998011876A1 (fr) * | 1996-09-18 | 1998-03-26 | Marigen S.A. | Peresters de glycoside de bioflavonol et leur preparation en concentres et ultramicroemulsions a action pharmacologique |
WO1998048790A1 (fr) * | 1997-04-28 | 1998-11-05 | Anticancer, Inc. | Utilisation de la genisteine et de composes associes pour traiter certains etats lies aux hormones sexuelles |
WO1999022728A1 (fr) * | 1997-10-31 | 1999-05-14 | Arch Development Corporation | Procedes et compositions pour reguler l'activite de la 5-alpha-reductase |
FR2781154A1 (fr) * | 1998-07-15 | 2000-01-21 | Lafon Labor | Composition therapeutique a base d'isoflavonoides destinee a etre utilisee dans le traitement des tumeurs par des agents cytotoxiques |
WO2000066576A1 (fr) * | 1999-04-30 | 2000-11-09 | G.J. Consultants Pty Ltd | Metabolites d'isoflavone |
WO2001017985A1 (fr) * | 1999-09-03 | 2001-03-15 | Indena S.P.A. | Nouveaux derives de flavones, de xanthones et de coumarines |
WO2001049281A2 (fr) * | 1999-12-30 | 2001-07-12 | Proteotech, Inc. | COMPOSES AROMATIQUES POLYHYDROXYLES UTILISES DANS LE TRAITEMENT DE L"AMYLOIDOSE ET DE MALADIES CARACTERISEES PAR LA FORMATION DE FIBRES DE α-SYNUCLEINE |
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2001
- 2001-04-09 PL PL346955A patent/PL205635B1/pl unknown
-
2002
- 2002-04-08 WO PCT/PL2002/000029 patent/WO2002081491A2/fr not_active Application Discontinuation
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997029779A2 (fr) * | 1996-02-16 | 1997-08-21 | Regents Of The University Of Minnesota | Conjugues de egf-genisteine pour le traitement du cancer |
WO1997032872A1 (fr) * | 1996-03-05 | 1997-09-12 | Imperial College Of Science Technology And Medicine | Composes comportant un groupe sulfamate |
WO1998011876A1 (fr) * | 1996-09-18 | 1998-03-26 | Marigen S.A. | Peresters de glycoside de bioflavonol et leur preparation en concentres et ultramicroemulsions a action pharmacologique |
WO1998048790A1 (fr) * | 1997-04-28 | 1998-11-05 | Anticancer, Inc. | Utilisation de la genisteine et de composes associes pour traiter certains etats lies aux hormones sexuelles |
WO1999022728A1 (fr) * | 1997-10-31 | 1999-05-14 | Arch Development Corporation | Procedes et compositions pour reguler l'activite de la 5-alpha-reductase |
FR2781154A1 (fr) * | 1998-07-15 | 2000-01-21 | Lafon Labor | Composition therapeutique a base d'isoflavonoides destinee a etre utilisee dans le traitement des tumeurs par des agents cytotoxiques |
WO2000066576A1 (fr) * | 1999-04-30 | 2000-11-09 | G.J. Consultants Pty Ltd | Metabolites d'isoflavone |
WO2001017985A1 (fr) * | 1999-09-03 | 2001-03-15 | Indena S.P.A. | Nouveaux derives de flavones, de xanthones et de coumarines |
WO2001049281A2 (fr) * | 1999-12-30 | 2001-07-12 | Proteotech, Inc. | COMPOSES AROMATIQUES POLYHYDROXYLES UTILISES DANS LE TRAITEMENT DE L"AMYLOIDOSE ET DE MALADIES CARACTERISEES PAR LA FORMATION DE FIBRES DE α-SYNUCLEINE |
Non-Patent Citations (26)
Title |
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A.C.JAIN ET AL.: "A Study of Nuclear Prenylation and Allylation of Isoflavones and Synthesis of 4'-Methyl Ethers of Asajin and Warangalone.", TETRAHEDRON, vol. 26, no. 8, 1970, pages 1977 - 1988, XP001109153 * |
A.C.JAIN ET AL.: "Synthesis of Alpium Isoflavone, Osajin, and Warangalone.", JOURNAL OF ORGANIC CHEMISTRY., vol. 39, no. 15, 1974, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 2215 - 2217, XP001126263, ISSN: 0022-3263 * |
B.S.BAJWA ET AL.: "Synthesis of Eupatoriochromene, Encecalin, Isoevodionol, Alloptaeroxylin & Related Compounds.", INDIAN JOURNAL OF CHEMISTRY, vol. 9, 1971, pages 17 - 19, XP001126915 * |
C.L.HOLDER ET AL.: "Quantification of Soy Isoflavones, Genistein and Daidzein, and Conjugates in Rat Blood Using LC/EC-MS.", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 47, no. 9, 1999, pages 3764 - 3770, XP001126265 * |
CHEMICAL ABSTRACTS, vol. 132, no. 20, 15 May 2000, Columbus, Ohio, US; abstract no. 264129, "Production, isolation and structure elucidation of novel isoflavonoid compound K3-D4, K3-D5, K3-D6" XP002222414 * |
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D.R.DOERGE ET AL.: "Analysis of Soy Isoflavone Conjugation in Vitro and in Human Blood using Liquid Chromatography-Mass Spectrometry.", DRUG METABOLISM AND DISPOSITION, vol. 28, no. 3, 2000, pages 298 - 307, XP001126264 * |
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J.BORYSKI ET AL.: "A Regioselective Synthesis of Genistein 4'-O-Ribofuranosides.", SYNTHESIS., no. 14, November 2001 (2001-11-01), GEORG THIEME VERLAG. STUTTGART., DE, pages 2170 - 2174, XP002222413, ISSN: 0039-7881 * |
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K.NISHIYAMA ET AL.: "Syntheses of Isoflavones and Isoflavone Glycosides, and Their Inhibitory Activity Against Bovine Liver B-Galactosidase.", BIOSCIENCE, BIOTECHNOLOGY AND BIOCHEMISTRY, vol. 57, no. 1, 1993, pages 107 - 114, XP001109133 * |
L.FARKAS ET AL.: "About the Existence of Padmakastein and Padmakastin", TETRAHEDRON, vol. 25, no. 5, 1969, pages 1013 - 1019, XP001109134 * |
L.FARKAS ET AL.: "Transacylation reactions in the flavonoid series. IV. New syntheses of 5-methylgenistein, prunetin, biochanin-A and sissotrin", ACTA CHIMICA ACADEMIAE SCIENTIARUM HUNGARICAE, vol. 60, no. 3, 1969, pages 293 - 299, XP001126906 * |
LEWIS P ET AL: "SYNTHESIS OF ANTIOXIDANT ISOFLAVONE FATTY ACID ESTERS", SPECIAL PUBLICATION - ROYAL SOCIETY OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, LONDON, GB, vol. 240, 1999, pages 215 - 217, XP001122875, ISSN: 0260-6291 * |
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P.BEDNAREK ET AL.: "Profiling Changes in Metabolism of Isoflavonoids and their Conjugates in Lupinius albus Treated with Biotic Elicitor.", PHYTOCHEMISTRY, vol. 56, no. 1, 2001, pages 77 - 85, XP001126919 * |
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Also Published As
Publication number | Publication date |
---|---|
PL346955A1 (en) | 2002-10-21 |
PL205635B1 (pl) | 2010-05-31 |
WO2002081491A2 (fr) | 2002-10-17 |
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