KR100270284B1 - 킬레이트착물, 이를 포함하는 약제학적 조성물 및 이의 제조방법 및 이의 제조방법 - Google Patents
킬레이트착물, 이를 포함하는 약제학적 조성물 및 이의 제조방법 및 이의 제조방법 Download PDFInfo
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- KR100270284B1 KR100270284B1 KR1019930002814A KR930002814A KR100270284B1 KR 100270284 B1 KR100270284 B1 KR 100270284B1 KR 1019930002814 A KR1019930002814 A KR 1019930002814A KR 930002814 A KR930002814 A KR 930002814A KR 100270284 B1 KR100270284 B1 KR 100270284B1
- Authority
- KR
- South Korea
- Prior art keywords
- germanium
- phthalocyanine
- carbon atoms
- bis
- yloxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 12
- -1 Stearyloxy Chemical group 0.000 claims abstract description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims abstract description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
- 125000001931 aliphatic group Chemical class 0.000 claims abstract description 12
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002512 chemotherapy Methods 0.000 claims abstract description 11
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims abstract description 8
- 229910021480 group 4 element Inorganic materials 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 6
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 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 10
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- JWNFARDFOZLECD-UHFFFAOYSA-N COCCO[Ge](OCCOCCOC(C)=O)OCCOCCOC(C)=O Chemical compound COCCO[Ge](OCCOCCOC(C)=O)OCCOCCOC(C)=O JWNFARDFOZLECD-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000013522 chelant Substances 0.000 abstract description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 abstract description 2
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- 125000004429 atom Chemical group 0.000 abstract description 2
- 229910052733 gallium Inorganic materials 0.000 abstract description 2
- 229910052738 indium Inorganic materials 0.000 abstract description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 abstract description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
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- 239000000203 mixture Substances 0.000 description 36
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- 238000010992 reflux Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
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- 239000002244 precipitate Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
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- 239000012043 crude product Substances 0.000 description 4
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- 208000017983 photosensitivity disease Diseases 0.000 description 4
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
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- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960000271 arbutin Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- WZQSBCHNVPAYOC-UHFFFAOYSA-N chloro(trihexyl)silane Chemical compound CCCCCC[Si](Cl)(CCCCCC)CCCCCC WZQSBCHNVPAYOC-UHFFFAOYSA-N 0.000 description 1
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- CUUJVBDPSUOTIQ-UHFFFAOYSA-N hydroxy-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)O CUUJVBDPSUOTIQ-UHFFFAOYSA-N 0.000 description 1
- IKSRMYRCWBAVIQ-UHFFFAOYSA-N hydroxy-octadecoxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O)(OCCCCCCCCCCCCCCCCCC)C1=CC=CC=C1 IKSRMYRCWBAVIQ-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QXHRJCQMYAREHW-UHFFFAOYSA-N n,n-dimethylformamide;tetrachlorogermane Chemical compound CN(C)C=O.Cl[Ge](Cl)(Cl)Cl QXHRJCQMYAREHW-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 101150015886 nuc-1 gene Proteins 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- 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
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Medicines Containing Plant Substances (AREA)
- Polyethers (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH00600/92-1 | 1992-02-27 | ||
| CH60092 | 1992-02-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR930017912A KR930017912A (ko) | 1993-09-20 |
| KR100270284B1 true KR100270284B1 (ko) | 2000-10-16 |
Family
ID=4190744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930002814A Expired - Fee Related KR100270284B1 (ko) | 1992-02-27 | 1993-02-26 | 킬레이트착물, 이를 포함하는 약제학적 조성물 및 이의 제조방법 및 이의 제조방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US5358940A (enExample) |
| EP (1) | EP0558449B1 (enExample) |
| JP (1) | JPH0656839A (enExample) |
| KR (1) | KR100270284B1 (enExample) |
| CN (1) | CN1044476C (enExample) |
| AT (1) | ATE196143T1 (enExample) |
| AU (1) | AU662800B2 (enExample) |
| CA (1) | CA2090772A1 (enExample) |
| DE (1) | DE59310096D1 (enExample) |
| DK (1) | DK0558449T3 (enExample) |
| ES (1) | ES2151502T3 (enExample) |
| FI (1) | FI930831A7 (enExample) |
| GR (1) | GR3034887T3 (enExample) |
| HU (1) | HUT64075A (enExample) |
| IL (1) | IL104874A (enExample) |
| MX (1) | MX9301083A (enExample) |
| NO (1) | NO930719L (enExample) |
| NZ (1) | NZ247000A (enExample) |
| PT (1) | PT558449E (enExample) |
| SG (1) | SG49615A1 (enExample) |
| TW (1) | TW235298B (enExample) |
| ZA (1) | ZA931382B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5484778C1 (en) * | 1990-07-17 | 2001-05-08 | Univ Cleveland Hospitals | Phthalocynine photosensitizers for photodynamic therapy and methods for their use |
| US5179120A (en) * | 1991-06-28 | 1993-01-12 | Cytopharm, Inc. | Porphycene compounds for photodynamic therapy |
| GB9123814D0 (en) * | 1991-11-08 | 1992-01-02 | Johnson Matthey Plc | Photosensitizers |
| TW235298B (enExample) * | 1992-02-27 | 1994-12-01 | Ciba Geigy | |
| GB9405970D0 (en) * | 1994-03-25 | 1994-05-11 | Secr Defence | Substituted phthalocyanines |
| RU2106146C1 (ru) * | 1995-07-17 | 1998-03-10 | Институт элементоорганических соединений РАН | Средство для подавления опухолевого роста |
| US5763602A (en) * | 1996-10-01 | 1998-06-09 | Li; Ying-Syi | Methods of syntheses of phthalocyanine compounds |
| US5872248A (en) * | 1997-03-28 | 1999-02-16 | Case Western Reserve University | Methods for inserting silicon into phthalocyanines and naphthalocyanines |
| IL121440A0 (en) | 1997-07-31 | 1998-01-04 | Yeda Res & Dev | The use of 1,3,4,6-tetrahydroxy-helianthrone and its derivatives in photodynamic therapy and certain such novel derivatives |
| MXPA01008951A (es) * | 1999-03-05 | 2003-07-21 | Univ Case Western Reserve | Fotoblanqueadores liquidos hidrofobos. |
| US8211883B2 (en) * | 2004-04-01 | 2012-07-03 | Case Western Reserve University | Topical delivery of phthalocyanines |
| US7153956B2 (en) * | 2004-08-09 | 2006-12-26 | Silverbrook Research Pty Ltd | Cyanine dye having multifunctional peripheral groups |
| JP2010163473A (ja) * | 2009-01-13 | 2010-07-29 | Konica Minolta Business Technologies Inc | インクジェット記録用シアンインク |
| US8440641B2 (en) * | 2009-03-20 | 2013-05-14 | Case Western Reserve University | Phthalocyanine salt formulations |
| RU2682674C2 (ru) | 2013-03-15 | 2019-03-20 | Шерри Энн МАКФАРЛЭНД | Координационные комплексы на основе металлов в качестве фотодинамических соединений и их применение |
| WO2019188118A1 (ja) * | 2018-03-29 | 2019-10-03 | パナソニックＩｐマネジメント株式会社 | 組成物、光電変換素子および撮像装置 |
| JP6767695B2 (ja) * | 2018-03-29 | 2020-10-14 | パナソニックＩｐマネジメント株式会社 | 組成物、近赤外光電変換素子および撮像装置 |
| CN121001958A (zh) * | 2023-04-25 | 2025-11-21 | 佳能株式会社 | 单线态氧的产生方法、单线态氧的产生系统、单线态氧的产生试剂盒和单线态氧产生剂 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094536A (en) * | 1961-01-03 | 1963-06-18 | Malcolm E Kenney | Silicon phthalocyanines |
| US3094535A (en) * | 1961-01-03 | 1963-06-18 | Malcolm E Kenney | Germanium phthalocyanines |
| CA1337194C (en) * | 1988-04-07 | 1995-10-03 | Koichi Kamijima | Tetraazaporphin, process for producing the same, as well as optical recording media using the same and production processes thereof |
| US5109016A (en) * | 1988-05-23 | 1992-04-28 | Georgia State University Foundation, Inc. | Method for inhibiting infection or replication of human immunodeficiency virus with porphyrin and phthalocyanine antiviral compositions |
| DE3829851A1 (de) * | 1988-09-02 | 1990-03-08 | Basf Ag | Tetraazaporphyrine sowie strahlungsempfindliche beschichtungsfilme |
| US5457195A (en) * | 1989-12-21 | 1995-10-10 | Board Of Regents, The University Of Texas System | Sapphyrin derivatives and conjugates |
| ES2056617T3 (es) * | 1990-04-03 | 1994-10-01 | Ciba Geigy Ag | Formulacion de liposomas, aplicable de forma parenteral, constituida por lipidos sinteticos. |
| ATE206124T1 (de) * | 1990-05-15 | 2001-10-15 | Diatron Corp | Nachweisbar markierte markerverbindung mit einem fluorophor-rest , eine fluorescenz-probe mit der markerverbindung und verwendungen derselben. |
| US5120649A (en) * | 1990-05-15 | 1992-06-09 | New York Blood Center, Inc. | Photodynamic inactivation of viruses in blood cell-containing compositions |
| US5403928A (en) * | 1990-05-15 | 1995-04-04 | Diatron Corporation | Fluorescent marker components and fluorescent probes |
| US5166197A (en) * | 1990-07-17 | 1992-11-24 | Kenney Malcolm E | Phthalocyanine photosensitizers for photodynamic therapy |
| US5260435A (en) * | 1990-07-23 | 1993-11-09 | Nippon Oil And Fats Co., Ltd. | Derivative of naphthalocyanine containing perfluoroalkyl group, process for preparing the same and optical recording medium |
| GB9123814D0 (en) * | 1991-11-08 | 1992-01-02 | Johnson Matthey Plc | Photosensitizers |
| TW235298B (enExample) * | 1992-02-27 | 1994-12-01 | Ciba Geigy |
-
1993
- 1993-02-04 TW TW082100745A patent/TW235298B/zh active
- 1993-02-18 ES ES93810100T patent/ES2151502T3/es not_active Expired - Lifetime
- 1993-02-18 SG SG1996001068A patent/SG49615A1/en unknown
- 1993-02-18 EP EP93810100A patent/EP0558449B1/de not_active Expired - Lifetime
- 1993-02-18 AT AT93810100T patent/ATE196143T1/de not_active IP Right Cessation
- 1993-02-18 PT PT93810100T patent/PT558449E/pt unknown
- 1993-02-18 DE DE59310096T patent/DE59310096D1/de not_active Expired - Fee Related
- 1993-02-18 DK DK93810100T patent/DK0558449T3/da active
- 1993-02-24 AU AU33768/93A patent/AU662800B2/en not_active Ceased
- 1993-02-24 FI FI930831A patent/FI930831A7/fi unknown
- 1993-02-25 US US08/022,246 patent/US5358940A/en not_active Expired - Fee Related
- 1993-02-25 CA CA002090772A patent/CA2090772A1/en not_active Abandoned
- 1993-02-25 NZ NZ247000A patent/NZ247000A/en unknown
- 1993-02-26 KR KR1019930002814A patent/KR100270284B1/ko not_active Expired - Fee Related
- 1993-02-26 HU HU9300554A patent/HUT64075A/hu unknown
- 1993-02-26 JP JP5038723A patent/JPH0656839A/ja active Pending
- 1993-02-26 IL IL104874A patent/IL104874A/en not_active IP Right Cessation
- 1993-02-26 MX MX9301083A patent/MX9301083A/es not_active IP Right Cessation
- 1993-02-26 ZA ZA931382A patent/ZA931382B/xx unknown
- 1993-02-26 NO NO93930719A patent/NO930719L/no unknown
- 1993-02-26 CN CN93102147A patent/CN1044476C/zh not_active Expired - Fee Related
-
1994
- 1994-06-30 US US08/269,290 patent/US5670491A/en not_active Expired - Fee Related
-
1995
- 1995-12-15 US US08/573,102 patent/US5686439A/en not_active Expired - Fee Related
-
2000
- 2000-11-22 GR GR20000402576T patent/GR3034887T3/el not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Journal of American Chemical Society vol 112 p 8064 (1990년) * |
Also Published As
| Publication number | Publication date |
|---|---|
| PT558449E (pt) | 2001-02-28 |
| KR930017912A (ko) | 1993-09-20 |
| EP0558449B1 (de) | 2000-09-06 |
| TW235298B (enExample) | 1994-12-01 |
| AU3376893A (en) | 1993-09-02 |
| JPH0656839A (ja) | 1994-03-01 |
| ES2151502T3 (es) | 2001-01-01 |
| DK0558449T3 (da) | 2001-01-02 |
| US5358940A (en) | 1994-10-25 |
| NZ247000A (en) | 1995-07-26 |
| FI930831A7 (fi) | 1993-08-28 |
| HU9300554D0 (en) | 1993-05-28 |
| ZA931382B (en) | 1993-08-31 |
| CN1044476C (zh) | 1999-08-04 |
| NO930719D0 (no) | 1993-02-26 |
| MX9301083A (es) | 1993-09-01 |
| CN1075966A (zh) | 1993-09-08 |
| FI930831A0 (fi) | 1993-02-24 |
| CA2090772A1 (en) | 1993-08-28 |
| HUT64075A (en) | 1993-11-29 |
| US5670491A (en) | 1997-09-23 |
| IL104874A (en) | 1998-06-15 |
| SG49615A1 (en) | 2001-01-16 |
| ATE196143T1 (de) | 2000-09-15 |
| DE59310096D1 (de) | 2000-10-12 |
| GR3034887T3 (en) | 2001-02-28 |
| AU662800B2 (en) | 1995-09-14 |
| IL104874A0 (en) | 1993-06-10 |
| US5686439A (en) | 1997-11-11 |
| EP0558449A1 (de) | 1993-09-01 |
| NO930719L (no) | 1993-08-30 |
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