WO2009021978A3 - Carbaboranreste enthaltende verbindungen und deren verwendung in der medizin, insbesondere für die verwendung in der tumortherapie - Google Patents
Carbaboranreste enthaltende verbindungen und deren verwendung in der medizin, insbesondere für die verwendung in der tumortherapie Download PDFInfo
- Publication number
- WO2009021978A3 WO2009021978A3 PCT/EP2008/060649 EP2008060649W WO2009021978A3 WO 2009021978 A3 WO2009021978 A3 WO 2009021978A3 EP 2008060649 W EP2008060649 W EP 2008060649W WO 2009021978 A3 WO2009021978 A3 WO 2009021978A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- residue
- glycosylamine
- thioglycoside
- glycoside
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 206010028980 Neoplasm Diseases 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title abstract 2
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 150000008444 O-glycosides Chemical class 0.000 abstract 3
- 150000002341 glycosylamines Chemical class 0.000 abstract 3
- 150000003569 thioglycosides Chemical class 0.000 abstract 3
- 229930182474 N-glycoside Natural products 0.000 abstract 2
- 229930182473 O-glycoside Natural products 0.000 abstract 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- 229930182475 S-glycoside Natural products 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 230000000711 cancerogenic effect Effects 0.000 abstract 1
- 231100000315 carcinogenic Toxicity 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 1
- 239000011669 selenium Substances 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6596—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having atoms other than oxygen, sulfur, selenium, tellurium, nitrogen or phosphorus as ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Die Erfindung betrifft Verbindung der allgemeinen Formel (I) wobei A für Sauerstoff, Schwefel oder Selen steht, (CB)n und (CB)m stehen jeweils für ein Carbaboran oder eine Kette von Carbaboranen. R1 ist ausgewählt aus Hydroxy, Alkoxy, Alkenoxy, O-Glycosid, Thioglycosid und Glycosylamin, PO42- oder P2O73- und A-M+. R2 und R4 sind ausgewählt aus O-Glycosidrest, Thioglycosidrest, Glycosylaminrest, PO42- oder P2O73- und A-M+. R3 ist ausgewählt aus Alkoxy, Alkenoxy, O-Glycosid, Thioglycosid, Glycosylamin oder ein Phosphonatrest. Durch ihren Gehalt an Zuckerresten binden die erfindungsgemäßen Verbindungen spezifisch an Rezeptoren auf der Oberfläche von karzinogenen Zellen. Zusätzlich wirken die Verbindungen durch die Phosphonatgruppen als Phosphatmimetika, wodurch eine Bindung speziell an calciumreiches Tumorgewebe erfolgt. Vorteilhaft sind die Verbindungen selbst nicht toxisch, weisen eine geringe unspezifische Proteinbindung auf und sind gut wasserlöslich. Die Erfindung betrifft weiter die Verwendung dieser Verbindungen als Arzneimittel, insbesondere in der Radio-Onkologie, sowie Verfahren zu deren Herstellung und Zwischenprodukte, die während des Herstellungsverfahrens erhalten werden.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102007038930.4 | 2007-08-13 | ||
DE102007038930A DE102007038930B4 (de) | 2007-08-13 | 2007-08-13 | Neue chemische Verbindung und deren Verwendung in der Medizin, insbesondere für die Verwendung in der Tumortherapie |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2009021978A2 WO2009021978A2 (de) | 2009-02-19 |
WO2009021978A3 true WO2009021978A3 (de) | 2009-04-09 |
Family
ID=40090446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2008/060649 WO2009021978A2 (de) | 2007-08-13 | 2008-08-13 | Carbaboranreste enthaltende verbindungen und deren verwendung in der medizin, insbesondere für die verwendung in der tumortherapie |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE102007038930B4 (de) |
WO (1) | WO2009021978A2 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102775449B (zh) * | 2012-08-20 | 2014-10-08 | 聊城大学 | 1,7-间位二碳十硼烷羧酸三苯基氯化锡化合物、制备方法及其应用 |
CA2998875C (en) | 2015-09-17 | 2023-08-29 | Ohio State Innovation Foundation | Carborane compounds and methods of use thereof |
CN113347979A (zh) * | 2018-12-03 | 2021-09-03 | 俄亥俄州创新基金会 | 碳硼烷化合物、碳硼烷类似物及其使用方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0068584A1 (de) * | 1981-06-30 | 1983-01-05 | THE PROCTER & GAMBLE COMPANY | Bor enthaltende Polyphosphonate für die Behandlung von Verkalkungstumoren |
DE3332068A1 (de) * | 1983-09-06 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von nukleosidalkyl-, aralkyl- und arylphosphoniten und -phosphonaten |
EP1113020A2 (de) * | 1993-12-02 | 2001-07-04 | Emory University | Bor-cluster enthaltende Nukleoside und Oligonukleoside |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5630786A (en) | 1994-06-27 | 1997-05-20 | Ionix Corporation | Boron neutron capture enhancement of fast neutron therapy |
JPH1180177A (ja) | 1997-09-04 | 1999-03-26 | Toray Ind Inc | ホウ素含有ビスホスホン酸化合物、その製造方法、およびその医薬用途 |
-
2007
- 2007-08-13 DE DE102007038930A patent/DE102007038930B4/de not_active Expired - Fee Related
-
2008
- 2008-08-13 WO PCT/EP2008/060649 patent/WO2009021978A2/de active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0068584A1 (de) * | 1981-06-30 | 1983-01-05 | THE PROCTER & GAMBLE COMPANY | Bor enthaltende Polyphosphonate für die Behandlung von Verkalkungstumoren |
DE3332068A1 (de) * | 1983-09-06 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von nukleosidalkyl-, aralkyl- und arylphosphoniten und -phosphonaten |
EP1113020A2 (de) * | 1993-12-02 | 2001-07-04 | Emory University | Bor-cluster enthaltende Nukleoside und Oligonukleoside |
Non-Patent Citations (4)
Title |
---|
ALEXANDER, ROY P. ET AL: "Chemistry of decaborane-phosphorus compounds. VI. Phosphino-m-carboranes", INORGANIC CHEMISTRY (WASHINGTON, DC, UNITED STATES) , 5(3), 493-5 CODEN: INOCAJ; ISSN: 0020-1669, 1966, XP002508859 * |
HILL, W. E. ET AL: "Preparation and characterization of di(tertiary phosphines) with electronegative substituents. 1. Symmetrical derivatives", INORGANIC CHEMISTRY , 17(9), 2495-8 CODEN: INOCAJ; ISSN: 0020-1669, 1978, XP002508858 * |
S. STADLBAUER, P. LÖNNECKE, E. HEY-HAWKINS: "Phosphonate-substituted Carbaboranes for Potential Use in BNCT", ADVANCES IN NEUTRON CAPTURE THERAPY 2006, PROCEEDINGS OF ICNCT-12, CHEMISTRY AND PHARMACY, (EDS. Y. NAKAGAWA, T. KOBAYASHI, H. FUKUDA), 2006, pages 215 - 216, XP002513129, Retrieved from the Internet <URL:http://www.uni-leipzig.de/chemie/hh/index.php?lang=de&id=artik0507> [retrieved on 20090203] * |
S. STADLBAUER, P. LÖNNECKE, E. HEY-HAWKINS: "Phosphonate-substituted Carbaboranes for Potential Use in BNCT", ADVANCES IN NEUTRON CAPTURE THERAPY, PROCEEDINGS OF ICNCT-12, CHEMISTRY AND PHARMACY, (EDS. Y. NAKAGAWA, T. KOBAYASHI, H. FUKUDA), 2006, pages 215 - 216, XP002513129 * |
Also Published As
Publication number | Publication date |
---|---|
DE102007038930A1 (de) | 2009-02-19 |
WO2009021978A2 (de) | 2009-02-19 |
DE102007038930B4 (de) | 2013-12-05 |
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