JP5103381B2 - フタロシアニン誘導体、その調製方法、これを有する医薬組成物、及びその使用 - Google Patents
フタロシアニン誘導体、その調製方法、これを有する医薬組成物、及びその使用 Download PDFInfo
- Publication number
- JP5103381B2 JP5103381B2 JP2008509453A JP2008509453A JP5103381B2 JP 5103381 B2 JP5103381 B2 JP 5103381B2 JP 2008509453 A JP2008509453 A JP 2008509453A JP 2008509453 A JP2008509453 A JP 2008509453A JP 5103381 B2 JP5103381 B2 JP 5103381B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phthalocyanine
- solvent
- process according
- zinc
- 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
Links
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims description 47
- 239000008194 pharmaceutical composition Substances 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 239000000047 product Substances 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003456 ion exchange resin Substances 0.000 claims description 8
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001226 reprecipitation Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 238000007069 methylation reaction Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 4
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 3
- 230000005526 G1 to G0 transition Effects 0.000 claims description 3
- 239000008098 formaldehyde solution Substances 0.000 claims description 3
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 238000003780 insertion Methods 0.000 claims description 2
- 230000037431 insertion Effects 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 10
- 229960002887 deanol Drugs 0.000 claims 4
- 239000012022 methylating agents Substances 0.000 claims 2
- 238000006485 reductive methylation reaction Methods 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 16
- 238000002428 photodynamic therapy Methods 0.000 abstract description 14
- 208000035143 Bacterial infection Diseases 0.000 abstract description 5
- 208000022362 bacterial infectious disease Diseases 0.000 abstract description 5
- 208000015181 infectious disease Diseases 0.000 abstract description 4
- 239000003504 photosensitizing agent Substances 0.000 abstract description 2
- 230000002165 photosensitisation Effects 0.000 abstract 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 208000007578 phototoxic dermatitis Diseases 0.000 description 3
- 231100000018 phototoxicity Toxicity 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000003642 reactive oxygen metabolite Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- WTSJLYWSCIPJNI-UHFFFAOYSA-N 3-(4-aminophenoxy)benzene-1,2-dicarbonitrile Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(C#N)=C1C#N WTSJLYWSCIPJNI-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 208000003322 Coinfection Diseases 0.000 description 2
- FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- -1 zinc (II) salt Chemical class 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- UZJZIZFCQFZDHP-UHFFFAOYSA-N 3-nitrobenzene-1,2-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C#N)=C1C#N UZJZIZFCQFZDHP-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010024774 Localised infection Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/315—Zinc compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000092A ITFI20050092A1 (it) | 2005-05-05 | 2005-05-05 | Derivati ftalocianinici, processo per la loro preparazione, composizioni farmaceutiche che li contengono e loro uso |
| ITFI2005A000092 | 2005-05-05 | ||
| PCT/EP2006/062062 WO2006117399A1 (en) | 2005-05-05 | 2006-05-04 | Phthalocyanine derivatives, process for their preparation, pharmaceutical compositions containing them, and their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008540384A JP2008540384A (ja) | 2008-11-20 |
| JP2008540384A5 JP2008540384A5 (enExample) | 2012-10-11 |
| JP5103381B2 true JP5103381B2 (ja) | 2012-12-19 |
Family
ID=36926810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008509453A Expired - Fee Related JP5103381B2 (ja) | 2005-05-05 | 2006-05-04 | フタロシアニン誘導体、その調製方法、これを有する医薬組成物、及びその使用 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8067404B2 (enExample) |
| EP (1) | EP1883641B1 (enExample) |
| JP (1) | JP5103381B2 (enExample) |
| CN (1) | CN101198611A (enExample) |
| AT (1) | ATE415405T1 (enExample) |
| AU (1) | AU2006243217B2 (enExample) |
| CA (1) | CA2607572C (enExample) |
| CY (1) | CY1108834T1 (enExample) |
| DE (1) | DE602006003887D1 (enExample) |
| DK (1) | DK1883641T3 (enExample) |
| ES (1) | ES2321136T3 (enExample) |
| IL (1) | IL187125A (enExample) |
| IT (1) | ITFI20050092A1 (enExample) |
| PL (1) | PL1883641T3 (enExample) |
| PT (1) | PT1883641E (enExample) |
| SI (1) | SI1883641T1 (enExample) |
| WO (1) | WO2006117399A1 (enExample) |
| ZA (1) | ZA200710362B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104888217B (zh) * | 2009-06-12 | 2018-10-16 | 鹿特丹伊拉斯谟大学医疗中心 | 用于癌症光动力学治疗的靶向纳米光药物 |
| IT1395907B1 (it) * | 2009-07-30 | 2012-11-02 | Molteni E C Dei Flii Alitti Societa Di Esercizio Spa L | Derivato ftalocianinico costituito da una miscela di quattro isomeri |
| CA2806094C (en) * | 2010-07-30 | 2018-06-12 | Advanced Photodynamic Technologies, Inc. | Composition and method for photodynamic disinfection |
| ITFI20110166A1 (it) | 2011-08-05 | 2013-02-06 | Molteni & C | Nuovi fotosensibilizzanti ad uso terapeutico. |
| CN104003994A (zh) * | 2014-06-03 | 2014-08-27 | 南京师范大学 | 一种阳离子酞菁及其制备和应用 |
| CN104003993B (zh) * | 2014-06-03 | 2016-09-14 | 南京师范大学 | 一种多胺类酞菁及其衍生物、它们的制备和应用 |
| CN107686485A (zh) * | 2017-09-29 | 2018-02-13 | 西京学院 | 一种苯撑乙烯金属酞菁化合物及其制备方法 |
| WO2021001445A1 (en) * | 2019-07-01 | 2021-01-07 | Chemical Intelligence Limited | Antimicrobial dyes for healthcare apparel |
| CN112014383B (zh) * | 2020-06-30 | 2024-03-29 | 杜旭忠 | 一种用于均相化学发光的光敏剂及其制备方法和应用 |
| IT202300011709A1 (it) * | 2023-06-08 | 2024-12-08 | L Molteni & C Dei Fratelli Alitti Soc Di Esercizio S P A | Miscela di 3 isomeri di un derivato ftalocianinico |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8431924D0 (en) | 1984-12-18 | 1985-01-30 | Ici Plc | Optical recording medium |
| 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 |
| GB9317881D0 (en) | 1993-08-27 | 1993-10-13 | Secr Defence | Photosensitizers |
| IT1294325B1 (it) | 1997-08-14 | 1999-03-24 | Molteni L E C Dei Fratelli Ali | Zinco-ftalocianine e relativi coniugati, preparazione e uso nella terapia fotodinamica e come diagnostici |
| WO2000012512A1 (en) | 1998-08-28 | 2000-03-09 | Destiny Pharma Limited | Porphyrin derivatives, their use in photodynamic therapy and medical devices containing them |
| ATE259814T1 (de) * | 2000-06-15 | 2004-03-15 | Molteni & C | Substituierte metallphthalocyaninen, ihre herstellung und verwendung |
| PT1381611E (pt) | 2001-03-21 | 2005-11-30 | Molteni & C | Analogos de ftalocianina substituidas com metal sem centro de simetria sua preparacao e uso em terapia fotodinamica e em diagnostico in vivo |
| CN101200469B (zh) | 2001-10-29 | 2011-08-31 | L.莫尔特尼及阿利蒂兄弟联合股份公司 | 金属酞菁区域异构体的分离 |
| ES2244694T3 (es) | 2002-04-25 | 2005-12-16 | L. MOLTENI & C. DEI FRATELLI ALITTI SOCIETA' DI ESERCIZIO SOCIETA' PER AZIONI | Composiciones antibacterianas que comprenden analogos de metal ftalocianina. |
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2005
- 2005-05-05 IT IT000092A patent/ITFI20050092A1/it unknown
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2006
- 2006-05-04 PL PL06755021T patent/PL1883641T3/pl unknown
- 2006-05-04 AU AU2006243217A patent/AU2006243217B2/en not_active Ceased
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- 2006-05-04 DK DK06755021T patent/DK1883641T3/da active
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- 2006-05-04 CN CNA200680015327XA patent/CN101198611A/zh active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2006243217B2 (en) | 2011-07-28 |
| DK1883641T3 (da) | 2009-03-02 |
| ZA200710362B (en) | 2008-12-31 |
| ATE415405T1 (de) | 2008-12-15 |
| ES2321136T3 (es) | 2009-06-02 |
| AU2006243217A1 (en) | 2006-11-09 |
| PL1883641T3 (pl) | 2009-05-29 |
| CN101198611A (zh) | 2008-06-11 |
| IL187125A0 (en) | 2008-02-09 |
| CA2607572C (en) | 2013-10-22 |
| JP2008540384A (ja) | 2008-11-20 |
| WO2006117399A1 (en) | 2006-11-09 |
| EP1883641B1 (en) | 2008-11-26 |
| PT1883641E (pt) | 2009-03-06 |
| CA2607572A1 (en) | 2006-11-09 |
| SI1883641T1 (sl) | 2009-06-30 |
| DE602006003887D1 (de) | 2009-01-08 |
| US8067404B2 (en) | 2011-11-29 |
| CY1108834T1 (el) | 2014-07-02 |
| US20090131392A1 (en) | 2009-05-21 |
| IL187125A (en) | 2011-08-31 |
| ITFI20050092A1 (it) | 2006-11-06 |
| EP1883641A1 (en) | 2008-02-06 |
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