DE60022372T2 - Halbsandwich ruthenium(ii)-verbindungen mit einem stickstoff-haltigen liganden zur krebstherapie - Google Patents
Halbsandwich ruthenium(ii)-verbindungen mit einem stickstoff-haltigen liganden zur krebstherapie Download PDFInfo
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- DE60022372T2 DE60022372T2 DE60022372T DE60022372T DE60022372T2 DE 60022372 T2 DE60022372 T2 DE 60022372T2 DE 60022372 T DE60022372 T DE 60022372T DE 60022372 T DE60022372 T DE 60022372T DE 60022372 T2 DE60022372 T2 DE 60022372T2
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- sup
- compound according
- pyridine
- alkyl
- mmol
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- 239000003446 ligand Substances 0.000 title claims description 10
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000011275 oncology therapy Methods 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 16
- -1 cylcoalkyl Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 4
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims 3
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 claims 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims 2
- WYHXNQXDQQMTQI-UHFFFAOYSA-N n-benzylpyridin-2-amine Chemical compound C=1C=CC=CC=1CNC1=CC=CC=N1 WYHXNQXDQQMTQI-UHFFFAOYSA-N 0.000 claims 2
- HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 claims 2
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 claims 1
- 229910017008 AsF 6 Inorganic materials 0.000 claims 1
- ZKEMPJKEOSLZCF-UHFFFAOYSA-N OC(=O)C1=CC=NC=C1C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl Chemical compound OC(=O)C1=CC=NC=C1C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl ZKEMPJKEOSLZCF-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002524 organometallic group Chemical group 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002001 anti-metastasis Effects 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 3
- 229960000282 metronidazole Drugs 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 150000003303 ruthenium Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- 239000012327 Ruthenium complex Substances 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- AOLZGHVIBHTDNC-UHFFFAOYSA-N cyclohexa-2,5-dien-1-ylbenzene Chemical group C1=CCC=CC1C1=CC=CC=C1 AOLZGHVIBHTDNC-UHFFFAOYSA-N 0.000 description 2
- SITZRXZBFQSDJO-UHFFFAOYSA-N cyclohexa-2,5-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CCC=C1 SITZRXZBFQSDJO-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- DCLCXHDQESOFBQ-UHFFFAOYSA-N methyl cyclohexa-2,5-diene-1-carboxylate Chemical compound COC(=O)C1C=CCC=C1 DCLCXHDQESOFBQ-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 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
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
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- 238000000746 purification Methods 0.000 description 2
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- 229910052707 ruthenium Inorganic materials 0.000 description 2
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 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
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OOLUVSIJOMLOCB-UHFFFAOYSA-N 1633-22-3 Chemical class C1CC(C=C2)=CC=C2CCC2=CC=C1C=C2 OOLUVSIJOMLOCB-UHFFFAOYSA-N 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- QYBFRILKKAVWEP-UHFFFAOYSA-L benzene;2-(2-methyl-5-nitroimidazol-1-yl)ethanol;ruthenium(2+);dichloride Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1.CC1=NC=C([N+]([O-])=O)N1CCO QYBFRILKKAVWEP-UHFFFAOYSA-L 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- OGBDBLQBNVXCJX-UHFFFAOYSA-N hexane tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.CCCCCC OGBDBLQBNVXCJX-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
- DYUCNAMTUNGLAB-UHFFFAOYSA-N n,n'-bis(2-aminoethyl)hexane-1,6-diamine Chemical compound NCCNCCCCCCNCCN DYUCNAMTUNGLAB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical class [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000011581 secondary neoplasm Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical class NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910006400 μ-Cl Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9925274.4A GB9925274D0 (en) | 1999-10-27 | 1999-10-27 | Ruthenium (II) compounds |
| GB9925274 | 1999-10-27 | ||
| GB0016054A GB0016054D0 (en) | 2000-06-30 | 2000-06-30 | Ruthenium (II) compounds |
| GB0016054 | 2000-06-30 | ||
| PCT/GB2000/004144 WO2001030790A1 (en) | 1999-10-27 | 2000-10-26 | Half-sandwich ruthenium (ii) compounds comprising nitrogen containing ligands for treatment of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60022372D1 DE60022372D1 (de) | 2005-10-06 |
| DE60022372T2 true DE60022372T2 (de) | 2006-06-08 |
Family
ID=26244569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60022372T Expired - Fee Related DE60022372T2 (de) | 1999-10-27 | 2000-10-26 | Halbsandwich ruthenium(ii)-verbindungen mit einem stickstoff-haltigen liganden zur krebstherapie |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6750251B2 (enExample) |
| EP (1) | EP1224192B1 (enExample) |
| JP (1) | JP2003512471A (enExample) |
| AT (1) | ATE303393T1 (enExample) |
| DE (1) | DE60022372T2 (enExample) |
| DK (1) | DK1224192T3 (enExample) |
| ES (1) | ES2248136T3 (enExample) |
| WO (1) | WO2001030790A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1224192T3 (da) * | 1999-10-27 | 2006-01-02 | Univ Court The University Of E | Halvsandwich-ruthenium (II)-forbindelser omfattende nitrogenholdige ligander til behandling af cancer |
| GB0215526D0 (en) * | 2002-07-05 | 2002-08-14 | Univ Edinburgh | Anticancer compounds |
| DE602004014125D1 (de) * | 2003-04-30 | 2008-07-10 | Univ Edinburgh | Ruthenium(ii)-komplexe zur behandlung von tumoren |
| 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 |
| EP2016085B9 (en) | 2006-05-09 | 2015-12-30 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Transition metal complexes for inhibiting resistance in the treatment of cancer and metastasis |
| GB0610062D0 (en) * | 2006-05-19 | 2006-06-28 | Univ Edinburgh | Ruthenium (ll) compounds |
| CA2775356C (en) | 2009-10-08 | 2016-04-26 | Angus Chemical Company | Low-voc polyamines |
| US8383673B2 (en) * | 2010-03-19 | 2013-02-26 | City University Of Hong Kong | Nitridoosmium(VI) complexes for treatment of cancer |
| WO2013038395A1 (en) | 2011-09-16 | 2013-03-21 | Universidade De Lisboa | Transition metal complexes for pharmaceutical applications |
| WO2013136296A2 (en) | 2012-03-14 | 2013-09-19 | Universidade De Lisboa | Water-soluble organometallic ruthenium and iron compunds presenting heteroaromatic ligands |
| US9290528B1 (en) | 2013-03-15 | 2016-03-22 | University Of Kentucky Research Foundation | Light-activated compounds |
| US9751081B2 (en) | 2014-12-01 | 2017-09-05 | Clemson University | Self-regenerating antioxidant catalysts and methods of using the same |
| US10053480B1 (en) | 2017-10-11 | 2018-08-21 | King Saud University | Anti-quorum and DNA cleaving agent |
Family Cites Families (14)
| 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 |
| US4843069A (en) | 1984-07-24 | 1989-06-27 | Asta Pharma Ag | Medicament formulations containing ruthenium compounds with an antitumoral action |
| WO1986000804A1 (fr) | 1984-07-24 | 1986-02-13 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | Compositions de ruthenium a effet inhibiteur de tumeurs |
| 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 |
| 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 |
| 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 |
| US5386044A (en) | 1993-11-30 | 1995-01-31 | E. I. Du Pont De Nemours And Company | Polyhaloaromatic ruthenium complexes and reactions thereof |
| WO1996013510A1 (en) | 1994-10-28 | 1996-05-09 | Procept, Inc. | Ruthenium complexes and their use as immunosuppressive agents |
| US5708022A (en) | 1994-10-28 | 1998-01-13 | Procept, Inc. | Method for inhibiting immune response |
| 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 |
| DK1224192T3 (da) * | 1999-10-27 | 2006-01-02 | Univ Court The University Of E | Halvsandwich-ruthenium (II)-forbindelser omfattende nitrogenholdige ligander til behandling af cancer |
| GB0016052D0 (en) * | 2000-06-30 | 2000-08-23 | Univ Edinburgh | Ruthenium (II) compounds |
| GB0028025D0 (en) | 2000-11-17 | 2001-01-03 | Univ York | Compounds |
| GB0215526D0 (en) * | 2002-07-05 | 2002-08-14 | Univ Edinburgh | Anticancer compounds |
-
2000
- 2000-10-26 DK DK00971599T patent/DK1224192T3/da active
- 2000-10-26 DE DE60022372T patent/DE60022372T2/de not_active Expired - Fee Related
- 2000-10-26 WO PCT/GB2000/004144 patent/WO2001030790A1/en not_active Ceased
- 2000-10-26 AT AT00971599T patent/ATE303393T1/de not_active IP Right Cessation
- 2000-10-26 EP EP00971599A patent/EP1224192B1/en not_active Expired - Lifetime
- 2000-10-26 JP JP2001533142A patent/JP2003512471A/ja active Pending
- 2000-10-26 ES ES00971599T patent/ES2248136T3/es not_active Expired - Lifetime
-
2002
- 2002-04-26 US US10/134,404 patent/US6750251B2/en not_active Expired - Fee Related
-
2004
- 2004-05-18 US US10/848,416 patent/US6979681B2/en not_active Expired - Fee Related
-
2005
- 2005-06-23 US US11/165,372 patent/US20050239765A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20040220166A1 (en) | 2004-11-04 |
| EP1224192A1 (en) | 2002-07-24 |
| EP1224192B1 (en) | 2005-08-31 |
| DK1224192T3 (da) | 2006-01-02 |
| US6979681B2 (en) | 2005-12-27 |
| DE60022372D1 (de) | 2005-10-06 |
| US20050239765A1 (en) | 2005-10-27 |
| ATE303393T1 (de) | 2005-09-15 |
| WO2001030790A1 (en) | 2001-05-03 |
| US6750251B2 (en) | 2004-06-15 |
| JP2003512471A (ja) | 2003-04-02 |
| US20030023088A1 (en) | 2003-01-30 |
| ES2248136T3 (es) | 2006-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |