JP2008524182A - 置換ポルフィリンの調製方法 - Google Patents
置換ポルフィリンの調製方法 Download PDFInfo
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- JP2008524182A JP2008524182A JP2007546167A JP2007546167A JP2008524182A JP 2008524182 A JP2008524182 A JP 2008524182A JP 2007546167 A JP2007546167 A JP 2007546167A JP 2007546167 A JP2007546167 A JP 2007546167A JP 2008524182 A JP2008524182 A JP 2008524182A
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- 238000000034 method Methods 0.000 title claims abstract description 65
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- 239000002184 metal Substances 0.000 claims abstract description 40
- 229910052736 halogen Chemical group 0.000 claims abstract description 17
- 150000002367 halogens Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 238000003325 tomography Methods 0.000 claims abstract description 8
- 230000005298 paramagnetic effect Effects 0.000 claims abstract description 7
- 230000002285 radioactive effect Effects 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 156
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 81
- 239000002904 solvent Substances 0.000 claims description 34
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- 239000000203 mixture Substances 0.000 claims description 31
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 28
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 11
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
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- CGIHTNAMBYTYDB-UHFFFAOYSA-N [phenyl(prop-2-ynoxy)methyl] acetate Chemical compound C#CCOC(OC(=O)C)C1=CC=CC=C1 CGIHTNAMBYTYDB-UHFFFAOYSA-N 0.000 claims description 2
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 238000002390 rotary evaporation Methods 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
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- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- GKOZUEZYRPOHIO-IGMARMGPSA-N iridium-192 Chemical compound [192Ir] GKOZUEZYRPOHIO-IGMARMGPSA-N 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
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- 239000011733 molybdenum Substances 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- 238000002638 palliative care Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 1
- 229940097886 phosphorus 32 Drugs 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229930188006 polyphyllin Natural products 0.000 description 1
- RIZZXCJMFIGMON-UHFFFAOYSA-N prop-2-ynyl acetate Chemical compound CC(=O)OCC#C RIZZXCJMFIGMON-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
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- 239000012485 toluene extract Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- 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
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
-
- 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
- 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
-
- 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
- C07F5/02—Boron compounds
- C07F5/05—Cyclic compounds having at least one ring containing boron but no carbon in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0427589.7A GB0427589D0 (en) | 2004-12-16 | 2004-12-16 | Process for the preparation of a substituted porphyrin |
| PCT/GB2005/004784 WO2006064205A2 (en) | 2004-12-16 | 2005-12-13 | Process for the preparation of a boron-substituted porphyrin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008524182A true JP2008524182A (ja) | 2008-07-10 |
| JP2008524182A5 JP2008524182A5 (enExample) | 2009-02-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007546167A Pending JP2008524182A (ja) | 2004-12-16 | 2005-12-13 | 置換ポルフィリンの調製方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8680265B2 (enExample) |
| EP (1) | EP1830882B1 (enExample) |
| JP (1) | JP2008524182A (enExample) |
| KR (1) | KR20070100745A (enExample) |
| CN (1) | CN101098713A (enExample) |
| AU (1) | AU2005315446A1 (enExample) |
| BR (1) | BRPI0518951A2 (enExample) |
| CA (1) | CA2591042A1 (enExample) |
| GB (2) | GB0427589D0 (enExample) |
| RU (1) | RU2007126569A (enExample) |
| WO (1) | WO2006064205A2 (enExample) |
| ZA (1) | ZA200705767B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8287839B2 (en) | 2006-12-04 | 2012-10-16 | Brookhaven Science Associates, Llc | Carboranylporphyrins and uses thereof |
| WO2009105210A2 (en) * | 2008-02-19 | 2009-08-27 | Health Research, Inc. | B ring reduced-d ring oxidized tetrapyrollic photosensitizers for photodynamic therapy and tumor imaging |
| JP2017503755A (ja) * | 2013-11-22 | 2017-02-02 | エオルス サイエンシズ，インコーポレイテッド | ポルフィリン化合物の合成及び製剤化 |
| CN112010320B (zh) * | 2020-08-12 | 2023-05-23 | 河南师范大学 | 一种b取代氰基硼氢化钠的制备方法 |
| CN114790289B (zh) * | 2022-04-24 | 2023-08-11 | 中国船舶重工集团公司第七一八研究所 | 一种耐高温聚酰亚胺树脂的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002098417A1 (en) * | 2001-06-06 | 2002-12-12 | Brookhaven Science Associates | Novel metalloporphyrins and their uses as radiosensitizers for radiation therapy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5877165A (en) * | 1995-11-02 | 1999-03-02 | Brookhaven Science Associates | Boronated porhyrins and methods for their use |
| US6995260B2 (en) | 2004-05-20 | 2006-02-07 | Brookhaven Science Associates, Llc | Carboranylporphyrins and uses thereof |
-
2004
- 2004-12-16 GB GBGB0427589.7A patent/GB0427589D0/en not_active Ceased
-
2005
- 2005-12-13 RU RU2007126569/04A patent/RU2007126569A/ru not_active Application Discontinuation
- 2005-12-13 CA CA002591042A patent/CA2591042A1/en not_active Abandoned
- 2005-12-13 KR KR1020077016364A patent/KR20070100745A/ko not_active Withdrawn
- 2005-12-13 WO PCT/GB2005/004784 patent/WO2006064205A2/en not_active Ceased
- 2005-12-13 CN CNA2005800459882A patent/CN101098713A/zh active Pending
- 2005-12-13 JP JP2007546167A patent/JP2008524182A/ja active Pending
- 2005-12-13 BR BRPI0518951-9A patent/BRPI0518951A2/pt not_active IP Right Cessation
- 2005-12-13 AU AU2005315446A patent/AU2005315446A1/en not_active Abandoned
- 2005-12-13 EP EP05818446.6A patent/EP1830882B1/en not_active Expired - Lifetime
- 2005-12-13 US US11/721,865 patent/US8680265B2/en not_active Expired - Fee Related
-
2007
- 2007-07-13 ZA ZA200705767A patent/ZA200705767B/xx unknown
- 2007-07-16 GB GB0713798A patent/GB2436767A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002098417A1 (en) * | 2001-06-06 | 2002-12-12 | Brookhaven Science Associates | Novel metalloporphyrins and their uses as radiosensitizers for radiation therapy |
Non-Patent Citations (3)
| Title |
|---|
| JPN6012011893; ＭＩＵＲＡ，Ｍ． ｅｔ ａｌ: 'Ｂｏｒｏｎ Ｎｅｕｔｒｏｎ Ｃａｐｔｕｒｅ Ｔｈｅｒａｐｙ ｏｆ ａ Ｍｕｒｉｎｅ Ｍａｍｍａｒｙ Ｃａｒｃｉｎｏｍａ ｕｓｉｎｇ ａ Ｌｉｐｏｐｈｉｌｉｃ Ｃａｒｂｏｒａｎｙｌｔｅｔｒａｐｈｅｎｙｌ' Ｒａｄｉａｔ Ｒｅｓ Ｖｏｌ．１５５， Ｎｏ．４, 2001, ｐ．６０３-６１０ * |
| JPN6012011895; ＭＩＵＲＡ，Ｍ． ｅｔ ａｌ: 'Ｓｙｎｔｈｅｓｉｓ ｏｆ ｃｏｐｐｅｒ ｏｃｔａｂｒｏｍｏｔｅｔｒａｃａｒｂｏｒａｎｙｌｐｈｅｎｙｌｐｏｒｐｈｙｒｉｎ ｆｏｒ ｂｏｒｏｎ ｎｅｕｔｒｏｎ ｃａｐｔｕｒｅ ｔｈｅｒａｐｙ ａｎｄ ｉｔ' Ｂｒｉｔｉｓｈ Ｊｏｕｒｎａｌ ｏｆ Ｒａｄｉｏｌｏｇｙ Ｖｏｌ．７７， Ｎｏ．９１９, 2004, ｐ．５７３-５８０ * |
| JPN6012011897; ＭＩＵＲＡ，Ｍ． ｅｔ ａｌ: 'Ｅｖａｌｕａｔｉｏｎ ｏｆ ｃａｒｂｏｒａｎｅ-ｃｏｎｔａｉｎｉｎｇ ｐｏｒｐｈｙｒｉｎｓ ａｓ ｔｕｍｏｒ ｔａｒｇｅｔｉｎｇ ａｇｅｎｔｓ ｆｏｒ ｂｏｒｏｎ ｎｅｕｔｒｏｎ ｃａｐｔｕｒｅ ｔｈ' Ｂｒｉｔｉｓｈ Ｊｏｕｒｎａｌ ｏｆ Ｒａｄｉｏｌｏｇｙ Ｖｏｌ．７１, 1998, ｐ．７７３-７８１ * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1830882A2 (en) | 2007-09-12 |
| US20100016613A1 (en) | 2010-01-21 |
| EP1830882B1 (en) | 2016-10-26 |
| WO2006064205A3 (en) | 2007-02-01 |
| WO2006064205A2 (en) | 2006-06-22 |
| CN101098713A (zh) | 2008-01-02 |
| ZA200705767B (en) | 2008-09-25 |
| GB0713798D0 (en) | 2007-08-22 |
| GB2436767A (en) | 2007-10-03 |
| KR20070100745A (ko) | 2007-10-11 |
| US8680265B2 (en) | 2014-03-25 |
| AU2005315446A1 (en) | 2006-06-22 |
| CA2591042A1 (en) | 2006-06-22 |
| RU2007126569A (ru) | 2009-01-27 |
| BRPI0518951A2 (pt) | 2008-12-16 |
| GB0427589D0 (en) | 2005-01-19 |
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