JP2008504365A - カルボラニルポルフィリン及びそれらの使用 - Google Patents
カルボラニルポルフィリン及びそれらの使用 Download PDFInfo
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- JP2008504365A JP2008504365A JP2007519285A JP2007519285A JP2008504365A JP 2008504365 A JP2008504365 A JP 2008504365A JP 2007519285 A JP2007519285 A JP 2007519285A JP 2007519285 A JP2007519285 A JP 2007519285A JP 2008504365 A JP2008504365 A JP 2008504365A
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- 150000004032 porphyrins Chemical class 0.000 title claims description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 71
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- 229910052796 boron Inorganic materials 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 29
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 238000002603 single-photon emission computed tomography Methods 0.000 claims abstract description 17
- 238000003384 imaging method Methods 0.000 claims abstract description 15
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 229910021645 metal ion Inorganic materials 0.000 claims description 51
- -1 porphyrin compound Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 201000011510 cancer Diseases 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000010949 copper Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 238000002428 photodynamic therapy Methods 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
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- 229910052717 sulfur Inorganic materials 0.000 claims description 11
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
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- 239000011593 sulfur Substances 0.000 claims description 6
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003368 amide group Chemical group 0.000 claims description 5
- 229910052788 barium Inorganic materials 0.000 claims description 5
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- 150000001768 cations Chemical class 0.000 claims description 5
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- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052732 germanium Inorganic materials 0.000 claims description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052738 indium Inorganic materials 0.000 claims description 5
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229910052713 technetium Inorganic materials 0.000 claims description 5
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052721 tungsten Inorganic materials 0.000 claims description 5
- 239000010937 tungsten Substances 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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- 230000002285 radioactive effect Effects 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 3
- 229910052720 vanadium Inorganic materials 0.000 claims 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 3
- 230000002146 bilateral effect Effects 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 1
- 210000004556 brain Anatomy 0.000 abstract description 15
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 abstract description 12
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
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- 238000002405 diagnostic procedure Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 239000002904 solvent Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 210000001519 tissue Anatomy 0.000 description 22
- ZOXJGFHDIHLPTG-BJUDXGSMSA-N Boron-10 Chemical compound [10B] ZOXJGFHDIHLPTG-BJUDXGSMSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
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- 238000002390 rotary evaporation Methods 0.000 description 13
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- 239000000377 silicon dioxide Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 208000003174 Brain Neoplasms Diseases 0.000 description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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Classifications
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/009—Neutron capture therapy, e.g. using uranium or non-boron material
- A61K41/0095—Boron neutron capture therapy, i.e. BNCT, e.g. using boronated porphyrins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
- A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0485—Porphyrins, texaphyrins wherein the nitrogen atoms forming the central ring system complex the radioactive metal
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Radiology & Medical Imaging (AREA)
- Biochemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Radiation-Therapy Devices (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/878,138 US6989443B2 (en) | 2004-06-28 | 2004-06-28 | Carboranylporphyrins and uses thereof |
| PCT/US2005/022061 WO2006012140A1 (en) | 2004-06-28 | 2005-06-22 | Carboranylporphyrins and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008504365A true JP2008504365A (ja) | 2008-02-14 |
| JP2008504365A5 JP2008504365A5 (enExample) | 2008-08-07 |
Family
ID=35505984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519285A Pending JP2008504365A (ja) | 2004-06-28 | 2005-06-22 | カルボラニルポルフィリン及びそれらの使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6989443B2 (enExample) |
| EP (1) | EP1778082A4 (enExample) |
| JP (1) | JP2008504365A (enExample) |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5745415B2 (ja) * | 2009-09-17 | 2015-07-08 | 国立大学法人九州大学 | ポルフィリン化合物 |
| JP2017042311A (ja) * | 2015-08-25 | 2017-03-02 | 住友重機械工業株式会社 | 中性子捕捉療法システム及び中性子捕捉療法システムの制御方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070093463A1 (en) * | 2004-05-20 | 2007-04-26 | Brookhaven Science Associates, Llc | Radiation enhancement agent for X-ray radiation therapy and boron neutron-capture therapy |
| US8287839B2 (en) * | 2006-12-04 | 2012-10-16 | Brookhaven Science Associates, Llc | Carboranylporphyrins and uses thereof |
| US8444953B2 (en) * | 2007-03-22 | 2013-05-21 | Brookhaven Science Associates, Llc | Symmetric and asymmetric halogen-containing metallocarboranylporphyrins and uses thereof |
| US20080279781A1 (en) * | 2007-05-10 | 2008-11-13 | Brookhaven Science Associates, Llc | Glycosylated Carboranylporphyrins and Uses Thereof |
| CN102260269B (zh) * | 2010-05-25 | 2013-11-06 | 苏州和健医药科技有限公司 | 一种含有卟啉或二氢卟吩的树状化合物及其应用 |
| GB201212409D0 (en) | 2012-07-12 | 2012-08-22 | Morex Dev Partners Llp | Cancer treatment |
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| US5877165A (en) * | 1995-11-02 | 1999-03-02 | Brookhaven Science Associates | Boronated porhyrins and methods for their use |
| WO2001085736A1 (en) * | 2000-05-09 | 2001-11-15 | The Regents Of The University Of California | Porphyrin-based neutron capture agents for cancer therapy |
| WO2002098417A1 (en) * | 2001-06-06 | 2002-12-12 | Brookhaven Science Associates | Novel metalloporphyrins and their uses as radiosensitizers for radiation therapy |
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| US5162231A (en) | 1989-10-25 | 1992-11-10 | Cole Dean A | Method of using 5,10,15,20-tetrakis(carboxyphenyl)porphine for detecting cancers of the lung |
| US4959356A (en) | 1989-05-26 | 1990-09-25 | The United States Of America As Represented By The United States Department Of Energy | Porphyrins for boron neutron capture therapy |
| FR2656866B1 (fr) | 1990-01-10 | 1992-05-15 | Cis Bio Int | Derives de porphyrine et metalloporphyrines eventuellement couples a une molecule biologiquement active, et composition pharmaceutique les contenant. |
| US5149801A (en) | 1990-11-21 | 1992-09-22 | The Regents Of The University Of California | Boronated porphyrin compounds |
| US5654423A (en) | 1990-11-21 | 1997-08-05 | Regents Of The University Of California | Boronated metalloporphyrine and therapeutic methods |
| US5312896A (en) | 1992-10-09 | 1994-05-17 | Sri International | Metal ion porphyrin-containing poly(imide) |
| DE4305523A1 (de) | 1993-02-17 | 1994-08-18 | Diagnostikforschung Inst | Meso-Tetraphenylporphyrin-Komplexverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| IT232801Y1 (it) * | 1994-03-07 | 2000-01-19 | Imbac Spa | Fianco di cassonetto con gambo laterale di innesto asportabile e intercambiabile |
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| US5955586A (en) | 1996-03-22 | 1999-09-21 | Sessler; Jonathan L. | Highly boronated derivatives of texaphyrins |
| WO1998030102A1 (en) | 1997-01-09 | 1998-07-16 | Emory University | Non-iron metalloporphyrins and methods of use |
| US6010805A (en) | 1998-05-26 | 2000-01-04 | United States Of America As Represented By The Secretary Of The Air Force | Ion conducting electrolyte material containing a lithium porphyrin complex |
| US6566517B2 (en) | 2001-06-06 | 2003-05-20 | Brookhaven Science Associates, Llc | Metalloporphyrins and their uses as imageable tumor-targeting agents for radiation therapy |
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2004
- 2004-06-28 US US10/878,138 patent/US6989443B2/en not_active Expired - Fee Related
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2005
- 2005-06-22 NZ NZ552877A patent/NZ552877A/en not_active IP Right Cessation
- 2005-06-22 WO PCT/US2005/022061 patent/WO2006012140A1/en not_active Ceased
- 2005-06-22 EP EP05785045A patent/EP1778082A4/en not_active Withdrawn
- 2005-06-22 CA CA002572287A patent/CA2572287A1/en not_active Abandoned
- 2005-06-22 AU AU2005267390A patent/AU2005267390B2/en not_active Ceased
- 2005-06-22 JP JP2007519285A patent/JP2008504365A/ja active Pending
- 2005-06-22 KR KR1020077002041A patent/KR20070033006A/ko not_active Ceased
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2007
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| US5877165A (en) * | 1995-11-02 | 1999-03-02 | Brookhaven Science Associates | Boronated porhyrins and methods for their use |
| WO2001085736A1 (en) * | 2000-05-09 | 2001-11-15 | The Regents Of The University Of California | Porphyrin-based neutron capture agents for cancer therapy |
| WO2002098417A1 (en) * | 2001-06-06 | 2002-12-12 | Brookhaven Science Associates | Novel metalloporphyrins and their uses as radiosensitizers for radiation therapy |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5745415B2 (ja) * | 2009-09-17 | 2015-07-08 | 国立大学法人九州大学 | ポルフィリン化合物 |
| JP2017042311A (ja) * | 2015-08-25 | 2017-03-02 | 住友重機械工業株式会社 | 中性子捕捉療法システム及び中性子捕捉療法システムの制御方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ552877A (en) | 2010-03-26 |
| AU2005267390B2 (en) | 2011-01-20 |
| IL180365A0 (en) | 2007-06-03 |
| CN1988848A (zh) | 2007-06-27 |
| EP1778082A1 (en) | 2007-05-02 |
| CA2572287A1 (en) | 2006-02-02 |
| US6989443B2 (en) | 2006-01-24 |
| CN1988848B (zh) | 2010-12-15 |
| US20050287073A1 (en) | 2005-12-29 |
| KR20070033006A (ko) | 2007-03-23 |
| AU2005267390A1 (en) | 2006-02-02 |
| WO2006012140A1 (en) | 2006-02-02 |
| HK1109039A1 (en) | 2008-05-30 |
| IL180365A (en) | 2011-09-27 |
| NO20070509L (no) | 2007-01-29 |
| EP1778082A4 (en) | 2010-09-22 |
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