CA2578280A1 - Composes arene-ruthenium (ii) et leur utilisation dans la therapie du cancer. - Google Patents
Composes arene-ruthenium (ii) et leur utilisation dans la therapie du cancer. Download PDFInfo
- Publication number
- CA2578280A1 CA2578280A1 CA002578280A CA2578280A CA2578280A1 CA 2578280 A1 CA2578280 A1 CA 2578280A1 CA 002578280 A CA002578280 A CA 002578280A CA 2578280 A CA2578280 A CA 2578280A CA 2578280 A1 CA2578280 A1 CA 2578280A1
- Authority
- CA
- Canada
- Prior art keywords
- compound according
- carbocyclic
- alkyl
- compound
- ring
- 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.)
- Abandoned
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- -1 Arene ruthenium (ii) compounds Chemical class 0.000 title claims abstract description 52
- 238000011275 oncology therapy Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 56
- 239000003446 ligand Substances 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 150000002148 esters Chemical class 0.000 claims abstract description 27
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 22
- 229940002612 prodrug Drugs 0.000 claims abstract description 13
- 239000000651 prodrug Substances 0.000 claims abstract description 13
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 150000003568 thioethers Chemical class 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 claims abstract description 9
- 125000003368 amide group Chemical group 0.000 claims abstract description 9
- MSOONVMMTIVQIJ-UHFFFAOYSA-N S(=O)(=O)(O)S(=O)(=O)NONS(=O)(=O)S(=O)(=O)O Chemical compound S(=O)(=O)(O)S(=O)(=O)NONS(=O)(=O)S(=O)(=O)O MSOONVMMTIVQIJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims abstract description 5
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002540 isothiocyanates Chemical group 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001540 azides Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007944 thiolates Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 238000009472 formulation Methods 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 21
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 21
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 125000006413 ring segment Chemical group 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- 125000005488 carboaryl group Chemical group 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000006071 cream Substances 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- GHCAUEMXBSLMGU-UHFFFAOYSA-N oxadiazole;1,2,5-oxadiazole Chemical compound C=1C=NON=1.C1=CON=N1 GHCAUEMXBSLMGU-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- 229910017673 NH4PF6 Inorganic materials 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical class N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000012937 correction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000000155 isotopic effect Effects 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 238000011200 topical administration Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 3
- 241000220479 Acacia Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 229930194542 Keto Natural products 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
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- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
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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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 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
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0418643.3 | 2004-08-20 | ||
| GBGB0418643.3A GB0418643D0 (en) | 2004-08-20 | 2004-08-20 | Ruthenium (II) compounds |
| PCT/GB2005/003242 WO2006018649A1 (fr) | 2004-08-20 | 2005-08-19 | Composes arene-ruthenium (ii) et leur utilisation dans la therapie du cancer. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2578280A1 true CA2578280A1 (fr) | 2006-02-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002578280A Abandoned CA2578280A1 (fr) | 2004-08-20 | 2005-08-19 | Composes arene-ruthenium (ii) et leur utilisation dans la therapie du cancer. |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1786412A1 (fr) |
| JP (1) | JP2008510693A (fr) |
| KR (1) | KR20070060091A (fr) |
| CN (1) | CN101043885A (fr) |
| AU (1) | AU2005273726A1 (fr) |
| BR (1) | BRPI0514430A (fr) |
| CA (1) | CA2578280A1 (fr) |
| GB (1) | GB0418643D0 (fr) |
| MX (1) | MX2007002099A (fr) |
| NO (1) | NO20071481L (fr) |
| WO (1) | WO2006018649A1 (fr) |
| ZA (1) | ZA200702093B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10766915B2 (en) | 2013-03-15 | 2020-09-08 | Sherri Ann McFARLAND | Metal-based coordination complexes as photodynamic compounds and their use |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006017594A1 (de) | 2006-04-13 | 2007-10-18 | Wacker Chemie Ag | Neuartige Ru-Komplexe, deren Herstellung und Verwendung |
| EP2016085B9 (fr) | 2006-05-09 | 2015-12-30 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | COMPLEXES DE MÉTAUX DE TRANSITION PERMETTANT d'INHIBER LA RÉSISTANCE DANS LE TRAITEMENT DU CANCER ET DES MÉTASTASES |
| GB0711849D0 (en) | 2007-06-19 | 2007-07-25 | Oxford Biosensors Ltd | Redox Mediators |
| EP2067771A1 (fr) | 2007-12-03 | 2009-06-10 | EPFL Ecole Polytechnique Fédérale de Lausanne | Dérivés de Dihydroxypyrrolidine en tant que composés anti-cancéreux |
| EP2409697A1 (fr) | 2010-07-20 | 2012-01-25 | Université de Neuchâtel | Médicaments basés sur des complexes dinucléaires de ruthénium, osmium et fer comprenant des ligands à triple pont thiolato, sélénato, alkoxo et/ou amido |
| WO2013038395A1 (fr) | 2011-09-16 | 2013-03-21 | Universidade De Lisboa | Complexes de métaux de transition pour applications pharmaceutiques |
| WO2013136296A2 (fr) | 2012-03-14 | 2013-09-19 | Universidade De Lisboa | Composés de ruthénium et de fer organométalliques solubles dans l'eau présentant des ligands hétéroaromatiques |
| US9751081B2 (en) | 2014-12-01 | 2017-09-05 | Clemson University | Self-regenerating antioxidant catalysts and methods of using the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19736152A1 (de) * | 1997-08-14 | 1999-02-18 | Martin Wehlan | Azido-Aziridinkomplexe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP1224192B1 (fr) * | 1999-10-27 | 2005-08-31 | The University Court, The University Of Edinburgh | Composes de ruthenium (ii) demi-sandwich comprenant de l'azote contenant des ligands utilises dans le traitement du cancer |
| GB0016052D0 (en) * | 2000-06-30 | 2000-08-23 | Univ Edinburgh | Ruthenium (II) compounds |
| GB0215526D0 (en) * | 2002-07-05 | 2002-08-14 | Univ Edinburgh | Anticancer compounds |
-
2004
- 2004-08-20 GB GBGB0418643.3A patent/GB0418643D0/en not_active Ceased
-
2005
- 2005-08-19 EP EP05771813A patent/EP1786412A1/fr not_active Withdrawn
- 2005-08-19 CA CA002578280A patent/CA2578280A1/fr not_active Abandoned
- 2005-08-19 CN CNA2005800355417A patent/CN101043885A/zh active Pending
- 2005-08-19 AU AU2005273726A patent/AU2005273726A1/en not_active Abandoned
- 2005-08-19 BR BRPI0514430-2A patent/BRPI0514430A/pt not_active IP Right Cessation
- 2005-08-19 WO PCT/GB2005/003242 patent/WO2006018649A1/fr active Application Filing
- 2005-08-19 MX MX2007002099A patent/MX2007002099A/es not_active Application Discontinuation
- 2005-08-19 JP JP2007526570A patent/JP2008510693A/ja active Pending
- 2005-08-19 KR KR1020077006364A patent/KR20070060091A/ko not_active Application Discontinuation
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2007
- 2007-03-12 ZA ZA200702093A patent/ZA200702093B/xx unknown
- 2007-03-20 NO NO20071481A patent/NO20071481L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10766915B2 (en) | 2013-03-15 | 2020-09-08 | Sherri Ann McFARLAND | Metal-based coordination complexes as photodynamic compounds and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006018649A1 (fr) | 2006-02-23 |
| CN101043885A (zh) | 2007-09-26 |
| AU2005273726A1 (en) | 2006-02-23 |
| JP2008510693A (ja) | 2008-04-10 |
| GB0418643D0 (en) | 2004-09-22 |
| MX2007002099A (es) | 2007-04-24 |
| EP1786412A1 (fr) | 2007-05-23 |
| ZA200702093B (en) | 2008-08-27 |
| BRPI0514430A (pt) | 2008-05-06 |
| NO20071481L (no) | 2007-05-16 |
| KR20070060091A (ko) | 2007-06-12 |
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