GB956242A - New metal complexes of 1,10-phenanthrolines or bipyridines - Google Patents
New metal complexes of 1,10-phenanthrolines or bipyridinesInfo
- Publication number
- GB956242A GB956242A GB291861A GB291861A GB956242A GB 956242 A GB956242 A GB 956242A GB 291861 A GB291861 A GB 291861A GB 291861 A GB291861 A GB 291861A GB 956242 A GB956242 A GB 956242A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- phenanthroline
- substituted
- positions
- complex
- 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
Links
- 150000005045 1,10-phenanthrolines Chemical class 0.000 title abstract 6
- 229910052751 metal Inorganic materials 0.000 title abstract 4
- 239000002184 metal Substances 0.000 title abstract 4
- 239000003446 ligand Substances 0.000 abstract 15
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000003944 tolyl group Chemical group 0.000 abstract 6
- 125000005023 xylyl group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 4
- 230000007935 neutral effect Effects 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- 150000002500 ions Chemical class 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 238000011282 treatment Methods 0.000 abstract 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001905 inorganic group Chemical group 0.000 abstract 2
- 125000000962 organic group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 2
- LQJNQNGNLFTFEF-UHFFFAOYSA-N 1H-indeno[1,2-b]pyridin-5-ylmethanimine Chemical compound N=Cc1c2ccccc2c2[nH]cccc12 LQJNQNGNLFTFEF-UHFFFAOYSA-N 0.000 abstract 1
- UJAQYOZROIFQHO-UHFFFAOYSA-N 5-methyl-1,10-phenanthroline Chemical compound C1=CC=C2C(C)=CC3=CC=CN=C3C2=N1 UJAQYOZROIFQHO-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007824 aliphatic compounds Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 125000005594 diketone group Chemical group 0.000 abstract 1
- 150000004662 dithiols Chemical class 0.000 abstract 1
- IMJKDXBMGVHEPL-UHFFFAOYSA-N ethane-1,2-diamine;pentane-2,4-dione Chemical compound NCCN.CC(=O)CC(C)=O.CC(=O)CC(C)=O IMJKDXBMGVHEPL-UHFFFAOYSA-N 0.000 abstract 1
- 229940012356 eye drops Drugs 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- -1 mercaptans thioureas Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229940100662 nasal drops Drugs 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 229910052762 osmium Chemical group 0.000 abstract 1
- WDTAXVWFNQNNEZ-UHFFFAOYSA-N osmium 2,3,4,6-tetrachloro-5-methyl-1,10-phenanthroline Chemical compound [Os].ClC=1C(=C2C(=C(C(=NC2=C2N=CC=CC12)Cl)Cl)Cl)C WDTAXVWFNQNNEZ-UHFFFAOYSA-N 0.000 abstract 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000000197 pyrolysis Methods 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F15/0013—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
- C07F19/005—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00 without metal-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises metal complexes <FORM:0956242/C2/1> (B) where M represents ruthenium or osmium in the valency states II or III or Bis a bidentate ligand provided by 1,10-phenanthroline, substituted 1,10-phenanthroline and 2,21-bipyridine; X ligand groups (at least one being different from B) occupying the four remaining co-ordination positions associated with the metal the ligand groups being uni-, bi-, tri- or quadri-dentate or mixtures of unibi-and tridentate ligands, in the case where B is 1,10-phenanthroline and two of the remaining co-ordination positions of X are filled with 1,10-phenanthroline, the further two remaining co-ordinating positions are filled with substituted 1,10-phenanthroline or substituted 2,21-bi-pyridine or bidentate ligands which reduce the positive electrical charge m on the complex; m is the electrical charge on the complex, m being +2, +1, 0, -1 or -2, Y a cation for negative values of m and an anion for positive values of m; p is a number determined by the value of m and the valency of Y; Fe (III) is ferric iron; B1 a bidentate ligand provided by a substituted 1,10-phenanthroline or substituted 2,21-bipyridine; Z is an anion of an inorganic or organic acid and q is a number determined by the valency of Z; the substituted 1,10-phenanthrolines B and B1 being substituted by one to six alkyl, phenyl, tolyl, or xylyl groups in the 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-positions and the substituted 2,21-bipyridine by one to four alkyl, phenyl, tolyl or xylyl groups in the 4-, 5-, 6-, 41-, 51 or 61-positions, there being alkyl groups in one to six of the specified positions of the substituted 1,10-phenanthroline and phenyl, tolyl and xylyl groups in one or two of the positions, such alkyl substituents totalling one to fourteen carbon atoms and where di-substitution involves the 3-, 4- and 7-, 8-positions either pairs of carbon atoms may form part of 5-membered or 6-membered cycloalkane ring system and such phenyl, tolyl and xylyl mono- and di-substitutents totalling from six to sixteen carbon atoms and there being alkyl groups in one to four of the specified positions of the 2,21-bipyridine and mono- and di-substitution in the 5- and 51 positions with phenyl, tolyl and xylyl groups, the alkyl groups totalling from one to ten carbon atoms and phenyl, tolyl and xylyl groups from six to sixteen carbon atoms, avoiding steric hindrance in the case where the 1,10-phenanthroline is substituted in the 2- and 9-positions and the 2,21-bipyridine in the 6-and 61-positions; the preparation of compounds (A) by reacting together in a liquid medium under conditions in which reduction may occur to produce A, a complex (MBL4) (C) where L is a halogen atom or mixtures of halogen atoms and unidentate ligands, halogen atoms and a bidentate ligand, a halogen atoms and a tridentate ligand with an amount of substituting ligand or ligands to introduce the desired ligand group X by replacement of groups L or by heating, under conditions that will produce the desired complex, a complex BH+ (MBL14) (D) where L1 is a halogen atom to introduce the ligand B into the complex (1) by replacement of two of the groups L1 and the preparation of compounds (B) by reacting together in an acid medium a ferric salt with a base B1. Unidentate biligands X may be any organic or inorganic group capable of coordinating to the metal M such as organic compounds containing nitrogen or sulphur, including heterocyclics, thioethers, mercaptans thioureas and nitriles; inorganic and organic ions including hydroxyl, halide, thiocyanate, and acetate; neutral inorganic groups which donate electrons to form co-ordinate bonds including water and ammonia. Bidentate ligands are aliphatic compounds, substituted and unsubstituted aromatic and heterocyclic compounds and may be neutral groups, including diamines, dithiols, mercapto alkanols, substituted or unsubstituted 2,21-bipyridine or 1,10-phenanthroline; groups capable of losing one or more protons, causing reduction in the charge on the complex ion, including, diketones, glycine and b -hydroxy-quinoline and its derivatives; ions such as oxalate and tartrate. Tridentate ligands may be neutral groups including triamines, and 2,21,211-terpyridine; or charge reducing groups including a ,b -diaminopropionic acid. Quadridentate are organic groups and may be neutral groups including tetra-amines and charge reducing groups including 1,8-diamino-3, 6-dithiooctane, and ethylenediamine bis(acetylacetone). 5-Methyl-1, 10-phenanthroline and K2 (OS (IV)Cl6) react to give K(C13H11N2)(OS (IV)Cl6) which on pyrolysis forms the starting material (OS (IV) (C13H10N2)Cl4), tetrachloro (5-methyl -1,10-phenanthroline) osmium (IV). 1,10-Phenanthroline and K(Ru(III)Cl5H2O) may be reacted together to give the salt Phen H+ (Ru(III)PhenCl4) ('Phen' represents 1,10-phenanthroline) which on oxidation with chlorine gives (Ru(IV)PhCl4) and this on reduction and treatment with ammonium chloride gives NH4 (Ru (III) Phen Cl4). Therapeutic compositions comprise a metal complex of the invention and a carrier. The compositions are presented in forms suitable for the treatment of bacterial infections in humans, e.g. saline solutions, creams, lotions eye or nose drops, pessaries, suppositories, tablets and lozenges; for veterinary treatments, e.g. in a carrier such as paraffin and wax base or in anthelmintic preparations as a drench, preferably as an aqueous solution or suspension; or as plant fungicides or virocides as aqueous solutions or dispersible powders.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU56846/60A AU251889B2 (en) | 1960-01-25 | New metal complexes with homogeneous ligands, and their preparation | |
| AU56847/60A AU251582B2 (en) | 1960-01-26 | New metal complexes with heterogeneous ligands, and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB956242A true GB956242A (en) | 1964-04-22 |
Family
ID=25631466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB291861A Expired GB956242A (en) | 1960-01-26 | 1961-01-25 | New metal complexes of 1,10-phenanthrolines or bipyridines |
Country Status (4)
| Country | Link |
|---|---|
| BR (1) | BR6126156D0 (en) |
| CH (1) | CH415657A (en) |
| GB (1) | GB956242A (en) |
| NL (2) | NL260509A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986000905A1 (en) * | 1984-07-24 | 1986-02-13 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | Ruthenium compounds having a tumor inhibiting activity |
| FR2673183A1 (en) * | 1991-02-21 | 1992-08-28 | Asulab Sa | MONO, BIS OR TRIS (2,2'-BIPYRIDINE SUBSTITUTED) COMPLEXES OF A SELECTED METAL AMONG IRON, RUTHENIUM, OSMIUM OR VANADIUM AND THEIR PREPARATION PROCESSES. |
| US5171853A (en) * | 1991-08-05 | 1992-12-15 | North Carolina State University | Process of cleaving nucleic acids with oxoruthenium(IV) complexes |
| US6664462B2 (en) * | 2000-03-13 | 2003-12-16 | National Institute Of Advanced Industrial Science And Technology | Metal complex having β-diketonate, process for production thereof, photoelectric conversion element, and photochemical cell |
| CN111848663A (en) * | 2020-08-27 | 2020-10-30 | 西南大学 | Non-metal organic complex salt of phenanthroline and phenanthroline derivative, and preparation method and application thereof |
-
0
- NL NL260510D patent/NL260510A/xx unknown
- NL NL260509D patent/NL260509A/xx unknown
-
1961
- 1961-01-25 GB GB291861A patent/GB956242A/en not_active Expired
- 1961-01-26 CH CH90861A patent/CH415657A/en unknown
- 1961-01-26 BR BR12615661A patent/BR6126156D0/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986000905A1 (en) * | 1984-07-24 | 1986-02-13 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft M | Ruthenium compounds having a tumor inhibiting activity |
| AU570826B2 (en) * | 1984-07-24 | 1988-03-24 | Asta-Pharma Aktiengesellschaft | Ruthenium compounds having a tumor inhibiting activity |
| FR2673183A1 (en) * | 1991-02-21 | 1992-08-28 | Asulab Sa | MONO, BIS OR TRIS (2,2'-BIPYRIDINE SUBSTITUTED) COMPLEXES OF A SELECTED METAL AMONG IRON, RUTHENIUM, OSMIUM OR VANADIUM AND THEIR PREPARATION PROCESSES. |
| WO1992014741A1 (en) * | 1991-02-21 | 1992-09-03 | Asulab S.A. | Mono, bis or tris (2,2'-substituted bipyridine) complexes of a metal selected amongst iron, ruthenium, osmium or vanadium and preparation methods thereof |
| US5393903A (en) * | 1991-02-21 | 1995-02-28 | Asulab S.A. | Mono, bis or tris(substituted 2,2'-bipyridine) iron, ruthenium, osmium or vanadium complexes and their methods of preparation |
| US5171853A (en) * | 1991-08-05 | 1992-12-15 | North Carolina State University | Process of cleaving nucleic acids with oxoruthenium(IV) complexes |
| US6664462B2 (en) * | 2000-03-13 | 2003-12-16 | National Institute Of Advanced Industrial Science And Technology | Metal complex having β-diketonate, process for production thereof, photoelectric conversion element, and photochemical cell |
| CN111848663A (en) * | 2020-08-27 | 2020-10-30 | 西南大学 | Non-metal organic complex salt of phenanthroline and phenanthroline derivative, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH415657A (en) | 1966-06-30 |
| NL260510A (en) | |
| NL260509A (en) | |
| BR6126156D0 (en) | 1973-05-31 |
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