ES2227225T3 - Compuestos de rutenio (ii) para utilizar en la terapia del cancer. - Google Patents
Compuestos de rutenio (ii) para utilizar en la terapia del cancer.Info
- Publication number
- ES2227225T3 ES2227225T3 ES01945472T ES01945472T ES2227225T3 ES 2227225 T3 ES2227225 T3 ES 2227225T3 ES 01945472 T ES01945472 T ES 01945472T ES 01945472 T ES01945472 T ES 01945472T ES 2227225 T3 ES2227225 T3 ES 2227225T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- represent
- ring
- carbocyclic
- aryl
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 84
- 238000011275 oncology therapy Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 27
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 26
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 19
- -1 Ruthenium (II) compound Chemical class 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 15
- 239000003446 ligand Substances 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 6
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- SPIPKVJLGXVNNN-UHFFFAOYSA-N 1,4,9,10-tetrahydroanthracene Chemical compound C1C2=CC=CC=C2CC2=C1CC=CC2 SPIPKVJLGXVNNN-UHFFFAOYSA-N 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- FTDLXZYXJAJLIP-UHFFFAOYSA-N 1,4-dihydroanthracene Chemical compound C1=CC=C2C=C3CC=CCC3=CC2=C1 FTDLXZYXJAJLIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229910001868 water Inorganic materials 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000012327 Ruthenium complex Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 4
- 229960000282 metronidazole Drugs 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- LNRAWXJRDXDHJN-UHFFFAOYSA-N 1,4,5,8,9,10-hexahydroanthracene Chemical compound C1C=CCC(C2)=C1CC1=C2CC=CC1 LNRAWXJRDXDHJN-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000002001 anti-metastasis Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- 229910017673 NH4PF6 Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- YYQQMZOBERDROY-UHFFFAOYSA-N n,n'-bis(2-aminoethyl)hexane-1,6-diamine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.NCCNCCCCCCNCCN YYQQMZOBERDROY-UHFFFAOYSA-N 0.000 description 2
- ATIZXQXXUBAQOD-UHFFFAOYSA-N n,n'-bis[2-(tritylamino)ethyl]hexane-1,6-diamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)NCCNCCCCCCNCCNC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ATIZXQXXUBAQOD-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
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- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ARPANWHHRGVXBN-UHFFFAOYSA-N 1,2,3,4,4a,10-hexahydroanthracene Chemical compound C1=CC=C2CC(CCCC3)C3=CC2=C1 ARPANWHHRGVXBN-UHFFFAOYSA-N 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000004881 tumor cell Anatomy 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0016052 | 2000-06-30 | ||
| GBGB0016052.3A GB0016052D0 (en) | 2000-06-30 | 2000-06-30 | Ruthenium (II) compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2227225T3 true ES2227225T3 (es) | 2005-04-01 |
Family
ID=9894730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01945472T Expired - Lifetime ES2227225T3 (es) | 2000-06-30 | 2001-06-26 | Compuestos de rutenio (ii) para utilizar en la terapia del cancer. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6936634B2 (enExample) |
| EP (1) | EP1294732B1 (enExample) |
| JP (1) | JP2004502696A (enExample) |
| AT (1) | ATE273985T1 (enExample) |
| AU (1) | AU2001267687A1 (enExample) |
| BR (1) | BR0112122A (enExample) |
| CA (1) | CA2414446A1 (enExample) |
| DE (1) | DE60105028T2 (enExample) |
| DK (1) | DK1294732T3 (enExample) |
| ES (1) | ES2227225T3 (enExample) |
| GB (1) | GB0016052D0 (enExample) |
| MX (1) | MXPA02012911A (enExample) |
| PT (1) | PT1294732E (enExample) |
| WO (1) | WO2002002572A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1224192B1 (en) * | 1999-10-27 | 2005-08-31 | The University Court, The University Of Edinburgh | Half-sandwich ruthenium (ii) compounds comprising nitrogen containing ligands for treatment of cancer |
| AU2002346686A1 (en) * | 2001-12-07 | 2003-06-23 | Intermune, Inc. | Compositions and method for treating hepatitis virus infection |
| GB0215526D0 (en) * | 2002-07-05 | 2002-08-14 | Univ Edinburgh | Anticancer compounds |
| AU2004234127A1 (en) | 2003-04-30 | 2004-11-11 | The University Court Of The University Of Edinburgh | Ruthenium (II) complexes for the treatment of tumors |
| GB0418643D0 (en) * | 2004-08-20 | 2004-09-22 | Univ Edinburgh | Ruthenium (II) compounds |
| GB0604602D0 (en) * | 2006-03-07 | 2006-04-19 | Univ Edinburgh | Ruthenium (II) compounds |
| GB0610062D0 (en) * | 2006-05-19 | 2006-06-28 | Univ Edinburgh | Ruthenium (ll) compounds |
| CN101851256B (zh) * | 2010-04-30 | 2013-01-09 | 广东药学院 | 一种以柔性碳链联接的钌(ⅱ)卟啉配合物及其制备方法和应用 |
| CN101863925B (zh) * | 2010-05-21 | 2012-08-29 | 广东药学院 | 一种芳基钌(ⅱ)配合物及其制备方法和应用 |
| US9751081B2 (en) | 2014-12-01 | 2017-09-05 | Clemson University | Self-regenerating antioxidant catalysts and methods of using the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980472A (en) | 1983-06-23 | 1990-12-25 | American Cyanamid Company | Method of making (3-amino-1H-pyrazol-4-yl) (aryl)methanones |
| AU570826B2 (en) | 1984-07-24 | 1988-03-24 | Asta-Pharma Aktiengesellschaft | Ruthenium compounds having a tumor inhibiting activity |
| WO1986000804A1 (fr) | 1984-07-24 | 1986-02-13 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | Compositions de ruthenium a effet inhibiteur de tumeurs |
| US4980473A (en) * | 1985-01-18 | 1990-12-25 | The Trustees Of Columbia University In The City Of New York | Chemical probes for left-handed DNA and chiral metal complexes as Z-specific anti-tumor agents |
| US5225556A (en) | 1985-01-18 | 1993-07-06 | The Trustees Of Columbia University In The City Of New York | Chemical probes for left-handed DNA and for A-DNA; chiral metal complexes as Z-specific antitumor agents and as double strand cleavers |
| US4699978A (en) | 1985-01-18 | 1987-10-13 | The Trustees Of Columbia University In The City Of New York | Site-specific chiral ruthenium (II) and cobalt (III) antitumor agents |
| AU4017695A (en) | 1994-10-28 | 1996-05-23 | Procept, Inc. | Ruthenium complexes and their use as immunosuppressive agents |
| JPH11209314A (ja) | 1997-09-30 | 1999-08-03 | Takasago Internatl Corp | シクロオクタジエン類の製造方法 |
| JP3488103B2 (ja) * | 1998-11-12 | 2004-01-19 | 高砂香料工業株式会社 | ４−メチル−５−ヘキセン−１−アールを含有する香料組成物 |
| GB0028025D0 (en) | 2000-11-17 | 2001-01-03 | Univ York | Compounds |
-
2000
- 2000-06-30 GB GBGB0016052.3A patent/GB0016052D0/en not_active Ceased
-
2001
- 2001-06-26 US US10/312,940 patent/US6936634B2/en not_active Expired - Fee Related
- 2001-06-26 DE DE60105028T patent/DE60105028T2/de not_active Expired - Fee Related
- 2001-06-26 AU AU2001267687A patent/AU2001267687A1/en not_active Abandoned
- 2001-06-26 CA CA002414446A patent/CA2414446A1/en not_active Abandoned
- 2001-06-26 JP JP2002507824A patent/JP2004502696A/ja active Pending
- 2001-06-26 MX MXPA02012911A patent/MXPA02012911A/es active IP Right Grant
- 2001-06-26 EP EP01945472A patent/EP1294732B1/en not_active Expired - Lifetime
- 2001-06-26 AT AT01945472T patent/ATE273985T1/de not_active IP Right Cessation
- 2001-06-26 BR BR0112122-7A patent/BR0112122A/pt not_active Application Discontinuation
- 2001-06-26 PT PT01945472T patent/PT1294732E/pt unknown
- 2001-06-26 WO PCT/GB2001/002824 patent/WO2002002572A1/en not_active Ceased
- 2001-06-26 DK DK01945472T patent/DK1294732T3/da active
- 2001-06-26 ES ES01945472T patent/ES2227225T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK1294732T3 (da) | 2004-12-06 |
| MXPA02012911A (es) | 2004-07-30 |
| US20040029852A1 (en) | 2004-02-12 |
| PT1294732E (pt) | 2004-12-31 |
| BR0112122A (pt) | 2003-05-13 |
| US6936634B2 (en) | 2005-08-30 |
| JP2004502696A (ja) | 2004-01-29 |
| DE60105028D1 (de) | 2004-09-23 |
| WO2002002572A1 (en) | 2002-01-10 |
| ATE273985T1 (de) | 2004-09-15 |
| EP1294732A1 (en) | 2003-03-26 |
| DE60105028T2 (de) | 2005-08-18 |
| EP1294732B1 (en) | 2004-08-18 |
| CA2414446A1 (en) | 2002-01-10 |
| AU2001267687A1 (en) | 2002-01-14 |
| GB0016052D0 (en) | 2000-08-23 |
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