FR2986796A1 - METHODS AND COMPOSITIONS FOR THE TREATMENT OF CANCER - Google Patents

Abstract

The present invention relates to uses or methods for the treatment of proliferative pathologies, in particular cancers, using osmium compounds and compositions containing them.

Description

The present invention relates to uses or methods for the treatment of proliferative pathologies, in particular cancers, using osmium compounds and compositions containing them. Platinum complexes are known to have significant antitumor activity. The best known of these is cisplatin, which is commonly used for the clinical treatment of many cancers. The resistance of certain cancer cells and the intrinsic toxicity of platinum are some of the problems encountered when using this compound. Since the 1970s, research has intensified to find molecules that can replace cisplatin and in recent years, compounds containing osmium have emerged as an interesting alternative to those containing platinum. Some complexes of osmium have thus already been described as being an alternative for cancer treatments. There is therefore a need for new anti-cancer agents which could be an alternative to those currently used, and advantageously more effective, and / or which would have less undesirable side effects. The present invention describes osmium compounds which have particularly advantageous anti-tumor properties. These compounds are organometallic compounds, that is to say they contain at least one covalent carbon-osmium bond. In addition, this C-Os bond is stabilized by another intramolecular nitrogen-osmium (N-Os) bond, the nitrogen atom being an element of the organic moiety bonded to osmium by the carbon atom. In this type of arrangement of atoms, osmium is therefore part of a cyclic entity and this class of compounds is commonly called by the chemists of the discipline the class of cyclometallic compounds. The cyclic entity containing the osmium is called a metallocycle. In such a metallocycle, the osmium is thus bound to an organic ligand by both a carbon-osmium covalent bond and a donor-acceptor (acid-Lewis base, or coordination link) nitrogen-osmium bond. The existence of such a metallocycle in an organometallic molecule gives it particular properties in terms of reactivity and thermodynamic stability. Various types of carbon atoms (aromatic, benzylic or aliphatic) can be metallated and the nature of the bond between the donor atom (nitrogen) and the carbon atom can be varied in many ways. According to a first aspect, the subject of the present invention is therefore a pharmaceutical composition comprising, in a pharmaceutically acceptable carrier, at least one osmium complex compound of the following general formula: L5, I6,1 \ 1) OL ( IS, C L3 wherein: between C and N, represented by a curved line, there is a succession of atoms forming, with C, N and Os represented on the formula, a ring (said metallocycle) which consists of 5 to 8 atoms, L3 and L4, identical or different, represent an aromatic ligand or a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom L5 and L6, present or absent simultaneously, identical or different, represent, when present, a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom, m is 0 or 1 and Y- is a counter-ion, when m = 1, each of L3, L4, L5 and L6 can covalently bonded to at least one other L3, L4, L5 and L6 ligand, and / or be covalently bonded to at least one metallocycle atom other than the osmium atom, when L5 and L6 are absent simultaneously, one of L3 and L4 is an aromatic ligand. L5 and L6 may be absent or present. If L5 is absent, so is L6, and vice versa. In all cases, the osmium atom has a coordination number of 6. Thus, L5 and L6 may be absent simultaneously if one of L3 and L4 is an aromatic ligand such as benzene or p-cymene, for example. L3 and L4, and L5 and L6, when present, are called ancillary ligands. Their main role is to complete the coordination sphere of the osmium atom.

The presence in the compounds according to the invention of the metallocycle comprising both an Os-N bond and an Os-C bond confers on the complexes according to the invention a significant anti-proliferative activity. In the context of the invention, the term "pharmaceutically acceptable carrier" means substances such as excipients, vehicles, adjuvants, buffers which are conventionally used for the preparation of a medicament, and physiologically acceptable for the subject. The choice of such supports depends essentially on the intended route of administration. The pharmaceutically acceptable carrier in which the compounds according to the invention can be employed, as well as its constituents, their amount, the dosage form of the composition, its method of preparation, and its mode of administration may be selected by the a person skilled in the art on the basis of his general knowledge according to the type of composition sought. The compounds of the invention may be in the form of pharmaceutically acceptable salts, solvates and / or prodrugs. The pro-drugs are variants of the compounds of the invention which can be converted in vivo into compounds of the general formula according to the invention. Ligands By "halogen atom" is meant in the present invention a fluorine, chlorine, bromine or iodine atom. Advantageously, the halogen atom is a chlorine atom. Ligands donating two electrons by an oxygen atom include, for example, H 2 O, di ((C 1-6) alkyl (O), di ((C 1-6) alkyl) C = O and (C 1-6) alkylCCO 2. The electron donating ligands of one sulfur atom include, for example, di ((C 1-6) alkyl) S, di ((C 1-6) alkyl) S (O) and (C 1-6) alkyl-503-. Preferably, the two-electron donor ligands by a sulfur atom are di ((C 1-6) alkyl) S (O) ligands, in particular the dimethylsulfoxide ligand.

The ligands that give two electrons via a nitrogen atom include, in particular, nitrile ligands, for example ligands of formula (C 1-6) alkylCN (in particular CH 3 CN) and optionally substituted pyridine ligands, on one or more carbon atoms of pyridine rings, with a halogen atom, an alkyl, aryl, hydroxyl, alkoxyl (O-alkyl), aryloxyl (O-aryl), carboxylic acid, ester (CO2-alkyl), thiol, thioether (S-alkyl) radicals , sulfinic acid, sulphonic acid, nitro, nitroxyl, amine (N (alkyl or aryl), (112, where x is an integer ranging from 0 to 2), trialkylammonium (N (alkyl or aryl) yH3_y + where y is an integer ranging from 0 to 3), hydroxylamine (N (OH), (alkyl or aryl) 2, where z is an integer ranging from 1 to 2), hydrazine, azo (N = N- (alkyl or aryl)), diazonium, amide (C0-1 \ 111, (alkyl or aryl) 2-, where w is an integer ranging from 0 to 2) or cyano, preferably the ligands donating two electrons by one atom; zote are CH3CN ligands, unsubstituted pyridine ligands, or pyridine ligands substituted by aryl, ester or amine radicals. Preferably, the pyridine ligands are substituted by a phenyl radical, a methoxycarbonyl radical, an ethoxycarbonyl radical or an amine NH 2 radical. The definitions of chemical radicals given in these paragraphs apply to all uses of these terms in this application. Among other ligands giving two electrons by a nitrogen atom, there may be mentioned primary amines (C 1-6) alkylNH 2, such as methylamine or ethylamine, and heterocycles such as oxazole, dihydrooxazole, imidazole or dihydroimidazole. Preferably, the two-electron donor ligands via a nitrogen atom are dihydrooxazole, imidazole or dihydroimidazole ligands. Ligands donating two electrons by a phosphorus atom include phosphine ligands. Advantageously, they are of formula P (Ph) alkyl, where x represents 0, 1 or 2, preferably x represents 2, and Ph represents the phenyl group. Among these ligands, there may be mentioned PPh3 or P (Ph) (CH3) 2. The aromatic ligands include arene ligands, in particular benzene and p-cymene (1-methyl-4- (1-methylethyl) benzene), optionally substituted with an ester (CO2-alkyl), alkyl or amine radical. In the case of aromatic ligands, one skilled in the art knows that the bond between the osmium atom and the aromatic ligand is not a covalent bond, it is in particular an n-type interaction, the aromatic contributing to 6 electrons to the electronic counting of osmium. Preferably, the benzene ligands are substituted by a methoxycarbonyl radical, an ethoxycarbonyl radical, a methyl radical or a dimethylamine radical. According to the invention, the term "alkyl" denotes a linear or branched hydrocarbon radical, saturated or unsaturated, advantageously having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, n-hexyl, etc. Groups having 1 to 4 carbon atoms are preferred. The alkyl groups may be substituted with an aryl group, in which case it is referred to as an arylalkyl group. Examples of arylalkyl groups include benzyl and phenethyl. The alkyl or arylalkyl groups may optionally have one or more substituents, chosen in particular from a halogen atom, an alkyl, aryl, hydroxyl, alkoxyl (O-alkyl), aryloxyl (O-aryl), carboxylic acid, ester (CO2) radical. -alkyl), thiol, thioether (S-alkyl), sulfinic acid, sulphonic acid, nitro, nitroxyl, amine, monoalkylamine, dialkylamine, trialkylammonium, mono- or dihydroxylamine, hydrazine, azo, diazonium, amide or cyano. The "aryl" groups are mono-, bi- or tri-cyclic aromatic hydrocarbon systems, optionally interrupted by at least one heteroatom (in particular O, S or N). Preferably, the aryl groups include monocyclic or bicyclic aromatic hydrocarbon systems having from 6 to 18 carbon atoms, more preferably 6 carbon atoms. Mention may be made, for example, of phenyl, naphthyl and biphenyl groups. When interrupted by hetero atoms, the aryl groups include pyridyl, imidazoyl, pyrrolyl and furanyl rings. The aryl groups may optionally have one or more substituents, chosen in particular from a halogen atom, an alkyl, aryl, hydroxyl, alkoxyl (O-alkyl), aryloxyl (O-aryl), carboxylic acid or ester (CO2-alkyl radical) radical. ), thiol, thioether (S-alkyl), sulfinic acid, sulphonic acid, nitro, nitroxyl, amine, monoalkylamine, dialkylamine, trialkylammonium, mono- or dihydroxylamine, hydrazine, azo, diazonium, amide or cyano.

According to one particular embodiment, two or three of the groups L3, L4, L5 and L6 may be connected to one another by at least one covalent bond. In this context, mention may be made in particular of the bipyridine, phenanthroline or terpyridine units, which are optionally substituted, in particular by at least one halogen atom, an alkyl, aryl, hydroxyl, alkoxyl (O-alkyl) or aryloxyl (O-aryl) radical. carboxylic acid, ester (CO2-alkyl), thiol, thioether (S-alkyl), sulfinic acid, sulphonic acid, nitro, nitroxyl, amine, monoalkylamine, dialkylamine, trialkylammonium, mono- or dihydroxylamine, hydrazine, azo, diazonium, amide or cyano. Preferably, the terpyridine units are substituted by an aryl radical or an ester radical. In particular, the terpyridine units are substituted with a toluyl (4-methylphenyl), methoxycarbonyl or ethoxycarbonyl radical. Preferably, the compounds of the invention have one, two, three or four L3, L4, L5 and L6 groups representing a donor ligand of two electrons by a nitrogen atom. L3, L4, L5 and / or L6 can be taken alone (named ligand monodentate), two by two (named bidentate ligand), by three (named tridentate ligand), or by four (named ligand tetradentate). When they are bi- or tri-dentate ligands, they may in particular represent a pyridine, bipyridine, phenanthroline or terpyridine group, said groups being optionally substituted, in particular by at least one halogen atom, an alkyl radical, aryl, hydroxyl, alkoxyl (O-alkyl), aryloxyl (O-aryl), carboxylic acid, ester (CO2-alkyl), dialkylsulfoxide, thiol, thioether (S-alkyl), sulfinic acid, sulphonic acid, nitro, nitroxyl, amine , monoalkylamine, dialkylamine, trialkylammonium, mono- or dihydroxylamine, hydrazine, azo, diazonium, amide or cyano. More specifically, the compounds according to the invention are such that the L 3, L 4 and L 5 groups together form a tridentate ligand, for example the L 3, L 4 and L 5 groups may together form terpyridine or 2- ( 2-pyridyl) - 1,10-phenanthroline, optionally substituted, on one or more carbon atoms of its pyridine rings, with at least one halogen atom, an alkyl, aryl, hydroxyl or alkoxyl (O-alkyl) radical, aryloxyl (O-aryl), carboxylic acid, ester (CO2alkyl), thiol, thioether (S-alkyl), sulfinic acid, sulphonic acid, nitro, nitroxyl, amine, monoalkylamine, dialkylamine, trialkylammonium, mono- or dihydroxylamine, hydrazine, azo , diazonium, amide or cyano. Preferably, the substituent is an aryl radical, preferably phenyl, advantageously itself substituted by a methyl or methoxyl radical. According to the invention, the terms "bipyridine", "phenanthroline", "terpyridine" and "2- (2-pyridyl) -1,10-phenanthroline" are as defined below, corresponding respectively to the ligands 5, 6, 7 and 8: NN (5) (6) The metallocycle comprises from 5 to 8 atoms in the ring represented in formula (I). Preferably, the metallocycle comprises 5 atoms in the ring. The metallocycle is optionally substituted. The atoms of the metallocycle - other than the Os, C and N atoms present in the formula (I) - are preferably chosen from carbon, nitrogen, oxygen, sulfur or phosphorus atoms. Advantageously, the atoms of the metallocycle - other than the Os, C and N atoms present in formula (I) are carbon atoms, and possibly at least one oxygen and nitrogen atom. The metallocycle may be optionally substituted by at least one halogen atom, an alkyl, aryl, hydroxyl, alkoxyl (O-alkyl), aryloxyl (O-aryl), carboxylic acid, ester (CO2-alkyl), thiol, thioether radical. (S-alkyl), sulfinic acid, sulphonic acid, nitro, nitroxyl, amine, monoalkylamine, dialkylamine, trialkylammonium, mono- or dihydroxylamine, hydrazine, azo, diazonium, amide or cyano. According to one particular embodiment of the invention, the metallocycle may in particular be chosen from: The cycles indicated above are named in the present document. In these formulas, only the cycle is shown, the osmium is of course also connected to L3, L4, L5 and L6 according to formula (I) defined above. The N 2 CH 4 rings may be substituted according to the substituents defined above, more specifically they may be substituted by an amine (NH 2), monoalkylamine or dialkylamine radical. In particular, the substituted ring may be a ring selected from: NH2 When the metallocycle is covalently linked to L3, it may in particular be selected from: and The two metallocycles indicated above are named herein. ^ CH ^ I \ I and I \ I ^ N ^ CH respectively. In these formulas, only the cycle is shown, the osmium is of course also connected to L4, L5 and L6 according to formula (I) defined above. The cycles I or CH may be substituted according to the substituents defined above, more specifically they may be substituted by at least one carboxylic acid, ester (CO2-alkyl) radical. or alkyl, in particular CH3, -COOCH3, -COOC2H5. In particular, the substituted metallocycles may be a ring selected from: and according to a particular embodiment of the invention, m is equal to 1. Y- in the compounds of the invention is a counter-ion and is only present in the compound when the osmium complex bears a positive charge. Y- is preferably a weakly nucleophilic anion, such as for example BF4-, B (C6H5) 4-, PF6-, CF3SO3-, tosylate (p-tolyl1SO3-), mesylate (MeSO3-), 5042-, CF3CO2-, CH3CO2-, bicarbonate (HCO3-), C104-, or NO3-, in particular PF6-. According to a first embodiment, the compounds of the invention have the formula (I) in which L5 and L6 are absent, L3 is an aromatic ligand and L4 represents a donor ligand of 2 electrons by a nitrogen atom, oxygen, phosphorus or sulfur, or a halogen atom, and in particular the metallocycle is a N CH cycle as indicated above. According to one particular embodiment, L3 is a benzene or p-cymene ligand, L4 is a chlorine atom, a di ((C16) alkyl) S (O) ligand (in particular (CH3) 2S (O)) or a ligand (C 1-6) alkylCN (especially CH 3 CN). According to this first embodiment, the compounds according to the invention are in particular chosen from: G -O PF 6 PF 6 G ODC 1 ODC 4 ODC 26 O PF 6 ODC 32 ODC 36 O PF 6 H2N ODC 27 ODC 39 -0 PF 6 ODC 37 ODC 38 O PF6 According to a second embodiment, the compounds of the invention have the formula (I) in which L3 and L4 are covalently connected and together form a bidentate ligand, in particular an electron donor ligand by nitrogen atoms, L5 and L6 are either covalently connected and together form a bidentate ligand, particularly an electron donor ligand by nitrogen atoms, or taken alone represent a monodentate ligand, in particular a donor ligand of 2 electrons per atom of nitrogen, oxygen, phosphorus or sulfur, or a halogen atom, and in particular the metallocycle is a NACH type cycle as indicated above. In a more particular embodiment, L3 and L4 together represent a bipyridine or phenanthroline unit and L5 and L6 together represent a bipyridine or phenanthroline unit. According to another more particular embodiment, L3 and L4 together represent a bipyridine or phenanthroline unit and L5 and L6, taken alone, represent a donor ligand of 2 electrons by a nitrogen atom, in particular a ligand (C 1-6) alkylCN (in particular CH 3 CN). According to a third embodiment, the compounds of the invention have the formula (I) in which L3, L4 and L5 are covalently connected and together form a tridentate ligand, in particular an electron donor ligand by nitrogen atoms L6 represents a monodentate ligand, in particular a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom, and in particular the metallocycle is an N-type ring ^ CH as indicated above. According to a more particular embodiment, L3, L4 and L5 together represent a terpyridine or 2- (2-pyridyl) -1,10-phenanthroline unit and L6 represents a donor ligand of 2 electrons by a nitrogen atom, in particular a ligand. (C1_6) alkylCN (in particular CH3CN). According to these second and third modes, the compounds according to the invention may be chosen in particular from: According to a fourth embodiment, the compounds of the invention have the formula (I) in which the metallocycle is covalently linked to L3 , in particular, the ring is of the type N 1 CH 2 N and N 1 N 2 CH 2 as described above, L 4 and L 5 are either covalently connected and together form a bidentate ligand, in particular an electron donor ligand by means of Nitrogen atoms, taken alone, represent a monodentate ligand, in particular a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom, and L6 represents a ligand monodentate, in particular a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom. According to a more particular embodiment, L4 and L5 together represent a bipyridine or phenanthroline unit and L6 represents a donor ligand of 2 electrons by a nitrogen atom, in particular a (C 1-6) alkylCN ligand (in particular CH 3 CN). In another mode 9 PFP ODC 33 Pe 13 PFP PFP ODC 2 ODC 3 ODC 5 9 9 pF, H2N PFP ODC 6 ODC 28 ODC 29 O ODC 34 ODC 35 e PF6 N Met ODC 30 O P more specific, L4, L5 and L6, taken alone, represent a donor ligand of 2 electrons by a nitrogen atom, in particular a ligand (C 1-6) alkylCN (in particular CH 3 CN). According to a fifth embodiment, the compounds of the invention have the formula (I) in which the metallocycle is covalently linked to L3, in particular the ring is of the type N ^ CH ^ N and N ^ N ^ CH such as described above, and L4, L5 and L6 are covalently connected and together form a tridentate ligand, particularly an electron donor ligand by nitrogen atoms. In a more particular embodiment, L4, L5 and L6 together represent a terpyridine or 2- (2-pyridyl) -1,10-phenanthroline unit. According to these fourth and fifth modes, the compounds of the invention may in particular be chosen from: PF6o PF6o ODC 7 ODC 8 ODC 9 PF, 0 PF6o PF6o ODC 10 ODC 11 ODC 12 Ô PF6o PF6o o ODC 13 ODC 14 ODC 15 PF6o PF6o The compositions or compounds according to the invention are particularly useful in the treatment of diseases related to cellular hyperproliferation, in particular cancers. Cancers include those with solid or liquid tumors. The cancers correspond in particular to melanomas, glioblastomas, neuroblastomas, leukemias, cancers of the prostate, kidneys, ovaries, lungs, breasts, head and neck, digestive tract, in particular of the liver. , pancreas, colon, and non-Hodgkin's lymphoma. The compounds of the invention exhibit an antiproliferative effect against tumor cells. They are particularly useful for treating cancers by accumulation of tumor cells in the GO / G1 or G2 / M phase and possibly by induction of apoptosis or another type of cell death of the tumor cells. Indeed, without wishing to be bound to any theory of the invention, the compounds of the invention appear in particular capable of accumulating tumor cells in the GO / G1 or G2 / M phase and thus by blocking their cell cycle, but also seem capable of generating their death rapidly, especially when their concentration is increased, sign of a dose-dependent toxicity. In addition, and without wishing to be bound to any theory of the invention, the compounds of the invention are capable of inducing different molecular mechanisms or modes of action that can explain anticancer properties. Indeed, on the one hand, the compounds of the invention can bind to the DNA and induce damage to it. On the other hand, they can induce early production of oxygen reactive derivatives and regulation of signaling pathways associated with cellular metabolism. These compounds can suppress phosphorylation of the S6 protein which is a marker of mTOR pathway activity. Conversely, they can induce the expression of the CHOP protein, which is a marker of the UPR (unfolded protein response) pathway. In addition, the compositions or compounds according to the invention are particularly useful in the treatment of tumors resistant to cisplatin or other anticancer drugs. The compositions or compounds according to the invention can be administered in different ways and in different forms. Thus, they can be administered systemically, orally, by inhalation or by injection, for example intravenously, intramuscularly, subcutaneously, trans-dermally, intra- arterially, etc., the intravenous routes, intramuscular, subcutaneous, oral and inhalation being preferred. For injections, the compositions are generally in the form of liquid suspensions, which can be injected by means of syringes or infusions, for example. In this respect, the compounds are generally dissolved in saline, physiological, isotonic, buffered, etc. solutions compatible with pharmaceutical use and known to those skilled in the art. Thus, the compositions according to the invention may contain one or more agents or vehicles chosen from dispersants, solubilizers, stabilizers, preservatives, etc. Agents or vehicles that can be used in liquid and / or injectable formulations include methylcellulose, hydroxymethylcellulose, carboxymethylcellulose, polysorbate 80, mannitol, gelatin, lactose, vegetable oils, acacia, etc. The compositions may also be administered in the form of gels, oils, tablets, suppositories, powders, capsules, aerosols, etc., possibly by means of dosage forms or devices providing sustained and / or delayed release. For this type of formulation, an agent such as cellulose, carbonates or starches is advantageously used. It is understood that the injection rate and / or the injected dose may be adapted by those skilled in the art depending on the patient, the pathology concerned, the mode of administration, etc. Typically, the compounds of the invention are administered at doses that can vary between 0.1 μg and 100 mg / kg of body weight, more generally between 0.01 and 10 mg / kg, typically between 0.1 and 10 mg / kg. kg. In addition, repeated injections can be performed. On the other hand, for chronic treatments, sustained release and / or delayed release systems may be advantageous. The invention also relates to a method for treating a pathology related to cellular hyperproliferation, in particular cancer, by administering to a subject afflicted with such a pathology an effective amount of a composition or a compound according to the invention. The subject of the present invention is also the use of at least one compound of formula (I), as defined above, in the context of the preparation of a pharmaceutical composition intended to treat diseases linked to cellular hyperproliferation. , especially cancers.

Among the other types of cell hyperproliferation whose treatment may be envisaged according to the invention may be mentioned benign tumors. In the context of the invention, the term "treatment" refers to the preventive, curative and palliative treatment, as well as the management of the patients (reduction of the suffering, improvement of the lifespan, slowing of the progression of the disease , reduction of tumor growth, etc.). The treatment may also be carried out in combination with other chemical or physical agents or treatments (chemotherapy, radiotherapy, gene therapy, etc.). The treatments and medicaments of the invention are particularly intended for humans but may also be intended for the animal (horse, dog, cat, sheep, cattle, ...). Thus, the compositions or compounds according to the invention can advantageously be used in combination with an anti-cancer treatment involving radiation, such as radiotherapy. According to another aspect of the invention, the compositions or compounds according to the invention can be used with other chemical agents or therapeutic anti-cancer treatments, such as the following therapeutic chemical agents: cisplatin, carboplatin, oxaliplatin , taxotere, taxol, irinotecan or rapamicine. The compounds of the invention are preferably packaged and administered in a combined, separate or sequential manner with respect to other therapeutic agents or treatments. The present invention also relates to a method for inhibiting the proliferation of tumor cells in vivo, in vitro or ex vivo, comprising contacting said tumor cells with a compound of formula (I) as defined above or a composition according to the invention. 'invention. The tumor cells can be in particular those of the pathologies specified above. According to another aspect, the subject of the present invention is an osmium complex compound corresponding to the general formula (I) as defined above, as well as all the specific, specific or preferred modes mentioned above.

In particular, the osmium complex according to the present invention is chosen from the compounds represented in FIG. 1. According to one particular embodiment of the invention, the compounds according to the invention are chosen from the compounds ODC4 -ODC24, ODC26-ODC37 and ODC39 Preparation methods: There are several methods for synthesizing the compounds of the invention. Preferably, the compounds according to the invention are synthesized by means of the cyclometallation reaction which makes it possible to obtain the metallocyclic unit by reacting an Osmium (II) complex such as the dinuclear compound [(r16-benzene) OsC12] 2 with the ligand N ^ CH or N ^ CH ^ N or N ^ N ^ CH in the presence of a base. From these compounds, the desired compounds are obtained by conventional substitution reactions of ancillary ligands. These reactions take place either in a non-coordinating solvent such as dichloromethane or in acetonitrile in the presence of stoichiometric amounts of the ligands which must be grafted onto the osmium atom. DESCRIPTION OF THE FIGURES In the figures and examples that follow, the terms "ODC" mean "compound derived from Osmium". FIG. 1: Examples of Complexes According to the Invention - FIGS. 1A and 1B FIG. 2A: The AM50 IC50 obtained for each of the compounds on the A172 line are presented in the table, with the IC50 in. the same line for ruthenium equivalents (named RDC for compounds derived from ruthenium). The IC50s obtained for the RIN line m5F, HCT116 and OVCAR3 are also shown in the table of Figure 2A. 2B: The diagrams represent the cell proliferation rate of the A172 line treated with increasing concentration ranges of osmium-derived compounds chosen from the 3 structural classes. The ranges include 8 concentrations ranging from 0.2 to 225 1.1M depending on the activity of each compound and each concentration results from the average of 8 individual points. An untreated control and the RDC11 at its IC50 (51.1M) constitute the internal controls. The thick red line sets the level of 50% growth. The amount of cells present in the wells was evaluated by an MTT test (MTT, Sigma) whose reaction products are quantified with an Elisa plate reader (Metertech, USA) (490-650 nm). The results obtained were related to the values of the control condition (100% viability). Table 2: Summary of IC50s obtained on various human cancer cell lines: HL60 and MOLT-4 (promyelocytic leukemia), A549 (lung carcinoma), HCT116 (colorectal carcinoma), U251 and SF295 (glioblastoma), OVCAR3 (adenocarcinoma) ovary), SK-MEL-5 (melanoma), PC3 (adenocarcinoma of the prostate), A498 (carcinoma of the kidney) and MCF7 (mammary adenocarcinoma) are cultured in RPMI 1640 medium, 5% fetal calf serum and 2mM L-glutamine. After 2 days of treatment, the use of a solution of sulforhodamine B allows the quantification of proteins by a colorimetric assay. Figure 3: Survival curve of C57Black 6 females after repeated dose administration of Osmium ODC3 compound. Four groups of four 8-week-old females receive repeated doses of ODC3 intraperitoneally according to the following protocol: OJ; J7, J10, J14, J17, J21; J24. Their weight is tracked and reflects the survival of the animals during the experiment. Figure 4: Upper panel: Growth curve of syngeneic lung tumors 3LL grafted subcutaneously on 2 groups of 8 female mice C57Black6 8 weeks treated with ODC4 (30 μM / kg 2x / week) and untreated. Lower panel: Representation of individual tumor volumes at D35 in ODC4-treated and untreated mice. Figure 5: Structures (ORTEP images) of ODC1, ODC4, ODC37, ODC32, ODC16, ODC9, ODC12 and ODC13. Figure 6: AI ODCs interact with DNA. 500 ng of circular double-stranded plasmid DNA (5000 bp) was incubated overnight with increasing amounts of ODC or RDC compounds to obtain the indicated compound / 10 base pair ratios. After incubation, the complexes were migrated on 1% agarose gel until the complexes were separated. These were then labeled with ethidium bromide. B ODCs induce phosphorylation of H2AX, a DNA damage marker. HCT116 cells were treated for 16h with the indicated compounds and at the indicated concentrations. Phosphorylation of the H2AX protein was then detected by Western blotting via a phosphospecific antibody to serine 137 (Millipore®). Actin has been used as an indicator of gel loading.

C ODCs induce DNA damage in cancer cells. The breaks in the DNA were visualized by comet assay. The HCT116 cancer cells were treated for one hour with ODC2, RDC11 or cisplatin (cis) at a concentration of 10 μM. After treatment, the cells are fixed and placed in a soft agarose gel. The set is then placed in an electric field. After a 30 minute migration, the DNA is labeled with propidium ionide. The damaged DNA comes out of the nucleus. The area occupied by the fluorescent DNA released is quantified by the Image J program and a percentage relative to the control was calculated. All images are taken at the same magnification X20. Figure 7: AI ODCs induce the production of oxygen radicals. HCT116 cells were treated with ODC2 and ODC3 at the indicated times. The presence of oxygen-reactive derivatives was detected by the carboxyH2DCFDA fluorescent probe. The bars indicate the average of eight wells and are percentages vis-à-vis the control condition. Standard errors are indicated. Asterisks indicate a statistically significant difference (p <0.001). B ODCs induce the expression of CHOP, a marker of the UPR pathway. HCT116 cells were treated for 16h with the indicated compounds and at the indicated concentrations. The expression of the CHOP protein was then detected by Western blotting via a specific antibody (Santacruz, USA, 1/1000). Actin has been used as an indicator of gel loading. C ODCs repress the phosphorylation of the S6 protein, a marker of the mTOR pathway. HCT116 cells were treated for 16h with the indicated compounds and at the indicated concentrations. Phosphorylation of the S6 protein was then detected by Western blotting via specific antibody (S235, 236, 1/1000, Cell Signaling Technology). Actin has been used as an indicator of gel loading. Other aspects and advantages of the present application will appear on reading the examples which follow, which should be considered as illustrative and not limiting.

EXAMPLES Example 1 Synthesis of the Complexes According to the Invention Generalities for the Synthesis of the Compounds The syntheses were carried out under argon atmosphere using a vacuum ramp. The solvents were distilled under an argon atmosphere under the following conditions: diethyl ether and pentane on sodium / benzophenone, dichloromethane and acetonitrile on calcium hydride and methanol and ethanol on magnesium. The chromatographic columns were prepared using alumina oxide (standardized neutral Merk 90). The following compounds were used as such: Aldrich: 1,3-cyclohexadiene, aphellandrene, 2-phenylpyridine, 2,2 bipyridine; Strem: osmium trichloride, 2,2 ', 6', 2 "-terpyridine, Alfa Aesar: 1,10-phenanthroline, Lancaster: potassium hexafluorophosphate The following compounds were synthesized following procedures already described: [(r16-bz) OsC12] 2, (Peacock, AF, Habtemariam, A, Fernandez, R., Walland, V., Fabbiani, FBA, Parsons, S., Aird, RE, Jodrell, I., Sadler, PJ I Am Chem Soc., 2006, 128, 1739-1748) [(p-cym) OsCl2] 2, (Werner, H., Zenkert, K. Organomet Chem, 1988, 345, 151-166) ODC 1: [Os (o-C6H4py-KC, N) (r / 6-C6H6) (NCMe)] PF6, (Ceron-Camacho, R. Morales-Morales, D. Hernandez, S. The Lagadec, R Ryabov, AD Inorg Chem 2008, 47, 4988-4995) ODC 2: [Os (o-C6H4py-KC, N) (phen) (NCMe) 2] PF6.3 ODC 3: [Os (o- C6H4py-KC, N) (phen) 21PF6.3 ODC 38: [Os (o-C6H4py-KC, N) (r / 6-C6H6) (Cl)] PF6,3 methyl-3,5-di (2- pyridyl) benzoate (IVIeO2C-N4C (H) ^ 1N), (Williams, G .; Beeby, A; Davies, ES; Weinstein, JA; Wilson, C. Inorg Chem., 2003, 42, 8609-8611; ) 3,5-di (2-pyridyl) toluene (Me-N ^C (H) NN), 4 ethoxycarbonyl-2,2 ': 6', 2 "-terpyridine, (Wadman, S.H .; Kroon, J.M .; Bakker, K; Havenith R. W. A .; Van Klink, G .; Van Koten, G. Organometallics, 2010, 29, 1569-1579) 2,2 ': 6', 2 "-terpyridine-4'-4'-4" tricarboxylate, (Nazeeruddin, MK; Pechy, P. Renouard, T, Zakeeruddin, SM, Humphry-Baker, R, Comte, P. Liska, P., Cevey, L., Costa, E., Shklover, V., Spiccia, L., Deacon, GB, Bignozzi, CA, Grâtzel, M. Am Am Chem Soc 2001, 123, 16131624) 4 '- (4-methylphenyl) -2,2': 6 ', 2 "-terpyridine, (Bhaumik, C., Das, S. , Saha, D., Dutta, S., Baitalik, S. Inorg Chem 2010, 49, 4049-4062) 4-Ethoxycarbonyl-6-phenyl-2,2'-bipyridine (IN1N- (EtO2)) C (H)), (Wadman, SH, Kroon, JM, Bakker, K., Havenith RWA, Van Klink, G., Van Koten, G. Organometallics, 2010, 29, 15691579) (Lu, W .; , MCW, Zhu, N, Che, C.M., Li, C, Hui, ZJ Am, Chem Soc., 2004, 126, 7639-7651) 4,4'-Di (methoxycarbonyl) -6- phenyl-2,2'-bipyridine (MeO 2 C) nN (IVIeO 2 C) 1N-C (H)), (Wadman, SH, Kroon, JM, Bakker, K, Havenith RWA, Van Klink, G, Van Koten , G. Organometallics, 2010, 29, 1569-1579) N, Ndimethyl-4- ( pyridin-2-yl) benzenamine, (Gosmini, C .; Bassene-Ernst, C .; Mirande et al. Tetrahedron, 2009, 65, 6141-6146 Gosmini, C .; Lasry, S .; Nedelec, J.-Y .; Perichonn, J. Tetrahedron, 1998, 54, 1289-1298) 4-amino-2-phenylpyridine. (Streef, J.W. Den Hertog, H.J. Tetrahedron Lett., 1968, 57, 5945-5948). 4'-methoxycarbonyl-2,2 ': 6', 2 "-terpyridine was synthesized using the same method as for 4'-ethoxycarbonyl-2,2 ': 6', 2" -terpyridine (Wadman, SH Kroon, JM, Bakker, K. Havenith RWA, Van Klink, G., Van Koten, G. Organometallics, 2010, 29, 15691579) using methanol instead of ethanol for final esterification. NMR spectra were obtained at room temperature on Brucker type spectrometers. 1E1 NMR spectra were recorded at 300.13 MHz (AC-300) or 400.13 MHz (AM-400) and referenced to SiMe4. 13CI1HI spectra were recorded at 75.48 MHz (AC-300) or 100.62 MHz (AC-400) and also referenced to SiMe4. Signal assignment was assisted by COZY experiments. The chemical shifts (δ) were referenced to the peak of the residual solvent and are expressed in ppm. The coupling constants (JHH) were expressed in Hz. The multiplicities of the signals were expressed as follows: s = singlet, d = doublet, t = triplet, q = quadruplet, seven = septuplet, m = multiplet. The infrared spectra were recorded on an ATR spectrometer (Brucker Optics) and analyzed with the OPUS software. The ES-MS spectra and the elementary analyzes were carried out respectively by the services of the Institute of Chemistry (University of Strasbourg) and the Central Analysis Service of the CNRS (Vernaison) (ODC 4): 10s (p-cymene) (NCMe) (2-C6H4-2-py-KC, N) 1PF6-PF? ODC 4 2-phenylpyridine (311 mg, 2.0 mmol) is added to a suspension of [OsCl (p-Cl) (p-cym)] (795 mg, 1.0 mmol), NaOH (80 mg, 2.0 mmol). ) and KPF6 (369 mg, 4.0 mmol) in 120 mL of acetonitrile. The medium is stirred at 40 ° C. for 48 h. After evaporation of the solvents and volatile products, the residue is dissolved in 20 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The bright yellow fraction is collected and concentrated to about 5 mL. Addition of 50 mL of diethyl ether causes precipitation of a yellow solid (962 mg, 75%). Anal. calc. for C23H25F6N2POs: C, 41.56; H, 3.79; N, 4.21. Found: C, 41.64; H, 3.85; N, 4.21 MS (ES, m / z): Calc. for C23H25N2192O5: 521.1633 (M); Found: 521.164 IR (cm-1): 2287 (weak, v1x1C), 837 (intense, vPF), 575 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.13 (dd, 1H, 3HHH = 5.7 , 4JHH = 1.2), 8.03-8.98 (m, 2H), 7.90 (td, 1H, 3./11E1 = 7.3, 4JHH = 1.5), 7.84 (dd, 1H, 3./xx = 7.3, 4./xx = 1.8), 7.24-7.10 (m, 3H), 5.86 (d, 1H, 3HH=5.7,), 5.83 (d, 1H, 3/1-1E1- 5.7), 5.73 (d, 1H, 3. /HH=5.7), 5.51 (d, 1H, 3HH = 5.7), 2.32 (q, 1H, 3HH = 6.9), 2.23 (s, 3H), 2.16 (s, 3H), 0.92 (d, 3H, 3HHH); 6.9), 0.86 (d, 3H, 3./HH = 6.9) 13c NMR (78 MHz, CD3CN, 300K): 156.2, 139.7, 138.9, 130.5, 124.3, 123.6, 123.4, 119.4, 83.2, 79.8, 74.8, 30.8 (ODC 5): 10s (terpy) (NC1VIe) (2-C6H4-2-py-KC, N) 1PF6 PF6 ODC A solution of ODC 1 (20 mg, 0.033 mmol) containing 2.2 ' 6 ', 2 "-terpyridine (7.28 mg, 0.031 mmol) in acetonitrile (5 mL) is stirred at reflux for 24 h, after evaporation of the solvents and volatile products, the residue is dissolved in 10 mL of CH 2 Cl 2 then filtered on A1203 (90:10 CH2C12 / NCMe) The purple color fraction is collected then evaporated to dryness. Recrystallization of this solid from a mixture of acetone / pentane (slow diffusion) or dichloromethane / pentane causes the precipitation of purple crystals (20 mg, 80%) which are then washed with pentane and then dried under vacuum.

Anal. calc. for C28H22F6N5POs: C, 44.04; H, 2.90; N, 9.17. Found: C, 43.81; H, 2.89; N, 8.97 MS (ES, m / z): Calc. for C28H22N5192O6: 620.1490 (M); Found: 620.154 IR (cm-1): 2287 (low, vNC), 830 (intense, vPF), 562 (average, vPF) 111 NMR (400 MHz, CD3CN, 300K): 8.44 (d, 2H, 3HHH = 8.14) ), 8.28 (d, 2H, 3HH = 8.2), 8.24 (d, 1H, 3HH = 7.5), 7.98 (d, 1H, 3HHH = 7.5), 7.82-7.87 (m, 3H), 7.68 (td, 2H, 3HH = 8.2, 4HH = 1.4), 7.6 (dd, 1H, 3HH = 8.1), 7.35 (td, 1H, 3HH = 7.5, 4HH = 1.2), 7.24 (td, 1H, 3HH = 7.5, 4HH = 1.5), 7.15 (td, 2H, 3JHH = 8.2, 4JHH = 1.5), 6.96 (td, 1H, 3JHH = 7.5, 4JHH = 1.5), 6.63 (d, 1H, 3JHH = 7.5), 6.42 (td, 1H, 3JHH = 7.5 , 4HH = 1.5), 2.11 (s, 3H) 13C (H) NMR (100.62 MHz, CD3CN, 300K): 156.2, 149.0, 135.5, 135.2, 135.0, 132.8, 129.4, 128.5, 123.6, 120.8, 120.7, 119.9 (ODC 6): 10s (bipy) (NCMe) 2 (2-C6H4-2-py-KC, N) 1PF6pF, ODC 6 Procedure similar to that for obtaining ODC 5, using a 2,2'-bipyridine ligand instead of 2,2 ', 6', 2 "-terpyridine (80% yield) Anal Calcd for C25H22F6N5POs: C, 41.26, H, 3.05, N, 9.62 Found: C, 41.05; 2.95; N, 9.52 MS (ES, m / z): Calc for C25H22NS192Qs: 584.1490 (M); Found: 584.158 IR ( cm-1): 2287 (weak, vNC), 830 (intense, vPF), 570 (average, vPF) 111 NMR (400 MHz, CD3CN, 300K): 9.23 (d, 1H, 3HH = 5.4), 8.39 (d , 1H, 3HH = 8.2), 8.20 (d, 1H, 3HH = 8.0), 7.92-8.00 (m, 3H), 7.85 (d, 1H, 3HH = 8.6), 7.81 (d, 1H, 3HHH = 7.2), 7.71 (td, 1H, 3HH = 6.7, 4HH = 1.3), 7.50 (td, 1H, 3HH = 7.9, 4HH = 1.4), 7.41 (td, 1H, 3HHH = 7.8, 4HH = 1.5), 7.32 (d, 1H , 3HH = 5.7), 7.18 (td, 1H, 3HH = 7.3.4JHH = 1.3), 6.90-6.99 (m, 2H,), 6.67 (td, 1H, 3HH = 6.7, 4HH = 1.3), 2.54 (s, 3H), 2.43 (s, 3H) 13C (H) NMR (100.62 MHz, CD3CN, 300K): 154.8, 150.4, 149.0, 136.0, 135.8, 135.3, 133.9, 129.5, 127.7, 126.2, 124.4, 123.2, 123.0, 121.4, 120.0 (ODC 7): 10s (phen) (NC1V1e) (1V1eO2C-N4C1N) 1PF6pF? ODC 7 A solution of ODC 21 (57 mg, 0.076 mmol) containing 1,10-phenanthroline (15 mg, 0.076 mmol) in methanol (5 mL) is stirred at reflux for 48 h. After evaporation of the solvents and volatile products, the dark brown residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 0.5 CH 2 Cl 2 / NCME). The purple fraction is collected and then evaporated to dryness. Recrystallization of this solid from a mixture of acetone / pentane (slow diffusion) or dichloromethane / pentane causes the precipitation of purple crystals (43 mg, 68%) which are then washed with diethyl ether and then dried under vacuum. Anal. calc. for C32H24F6N5O2P05: C, 45.44; H, 2.86; N, 8.28. Found: C, 45.25; H, 2.91; N, 8.18 MS (ES, m / z): Calc. for C32H24N5O2192O5: 702.1545 (M); Found: 702.159 IR (cm-1): 2249 (low, v1 TC), 1688 (mean vC = O), 831 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K) : 9.83 (dd, 1H, 3HH = 5.5, 4HH = 1.1), 8.69 (s, 2H), 8.50 (dd, 1H, 3HH = 8.1, 4HH = 1.1), 8.21-8.26 (m, 4H), 8.00 (d , 1H, 3HH = 9.0), 7.85 (dd, 1H, 3HH = 8.1, 4HH = 1.1), 7.63 (td, 2H, 3HH = 5.9, 4.41 = 1.5), 7.57 (d, 2H, 3HHH = 5.9), 7.21 (dd, 1H, 3HH = 5.5, 4HH = 1.1), 7.07 (dd, 1H, 3HH = 8.1.3JHH = 5.5), 6.78 (td, 2H, 3HH = 5.9, 4HH = 1.5), 4.00 (s, 3H) , 2.34 (s, 3H) 13 C (H) NMR (78 MHz, CD3CN, 300K): 171.4, 169.0, 155.9, 154.3, 149.6, 144.1, 137.0, 134.5, 133.9, 132.0, 131.3, 128.9, 128.6, 127.3, 125.0, 123.8, 121.5, 120.8, 120.0, 51.5 (ODC 8): 10s (bpy) (NCMe) (1VIeO2C-N6C1N) 1PF6 - \ ° NC EN 0 N pF? ODC 8 Similar procedure to that to obtain ODC 7, using a 2,2'-bipyridine ligand in place of 1,10-phenanthroline (65% yield). Anal. calc. for C30H24F6N5O2POs: C, 43.85; H, 2.94; N, 8.52. Found: C, 43.55; H, 2.91; N, 8.39 MS (ES, m / z): Calc. for C30H24N5O2192O5: 678.1545 (M); Found: 678.150 IR (cm-1): 2251 (weak, vNC), 1696 (mean vC = O), 834 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.51 (d, 1H, 3HH = 5.7), 8.64 (s, 2H), 8.52 (d, 1H, 3HH = 7.5), 8.19-8.26 (m, 3H), 7.95 (td, 1H, 3HHH = 7.5, 4HHH = 1.3). ), 7.80 (dd, 1H, 3HH = 5.7, 4HH = 1.3), 7.63-7.70 (m, 4H), 7.33 (dd, 1H, 3HH = 7.5, 4HH = 1.3), 6.88-6.95 (m, 3H), 6.67 (dd, 1H, 3HH = 5.5, 4HH = 1.3), 3.98 (s, 3H), 2.26 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 153.8, 153.0, 147.8, 142.9. , 136.0, 133.9, 133.1, 127.6, 125.9, 124.0, 123.5, 122.9, 119.8, 51.5 (ODC 9): 10s (terpy) (1V1e02C-N1CN) 1PF6 PFP ODC 9 Procedure similar to that for obtaining ODC 7 using a 2,2 ', 6', 2 "- terpyridine ligand in place of 1,10-phenanthroline (65% yield) Anal Calc for C33H24F6N5O2POs: C, 46.21; H, 2.82; N, 8.16 Found: C, 46.05, H, 2.83, N, 8.06 MS (ES, m / z): Calc for C33H24N5O2192Os: 714.1545 (M), Found: 714.155 IR (cm-1): 1698 (average vC = O) ), 834 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.91 (s, 2H), 8.73 (d, 2H, 3HH = 8.1), 8.42 (d, 2H, 3HH = 8.1), 8.30 (d, 2H, 3HHH = 8.1), 7.81 (t, 1H, 3HHH = 8.1), 7.50-7.59 (m, 4H), 7.06 (d, 2H, 3HH = 5.9), 6.91 (d, 2H, 3HH = 5.9), 6.85 (td, 2H, 3HHH = 5.9 , 4HH = 1.5), 6.64 (td, 2H, 3HH = 5.9, 4HH = 1.5), 4.04 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 155.4, 151.9, 135.3, 134.7, 131.0, 127.1, 124.3, 123.7, 122.1, 120.9, 120.1, 51.5 (ODC 10): 10s (phen) (NCMe) (Me-N-C-N) 1PF6 pF6 ODC A solution of ODC 22 (65mg, 0.092 mmol) containing 1,10-phenanthroline (18.3 mg, 0.092 mmol) in methanol (5 mL) is stirred at reflux for 48 h. After evaporation of the solvents and volatile products, the brown residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 0.5 CH 2 Cl 2 / NCME). The purple fraction is collected and evaporated to dryness. Recrystallization of this solid from a mixture of acetone / pentane (slow diffusion) or dichloromethane / pentane causes the precipitation of purple crystals (50 mg, 68%) which are then washed with diethyl ether and then dried under vacuum. Anal. calc. for C31H24F6N5POs: C, 46.44; H, 3.01; N, 8.74. Found: C, 46.25; H, 3.02; N, 8.65 MS (ES, m / z): Calc. for C31H24N51920s: 658.1647 (M); Found: 658.165 IR (cm-1): 2248 (low, v1 TC), 835 (intense, vPF), 575 (medium, vPF) 1H NMR (300 MHz, CD3CN, 300K): 9.85 (dd, 1H, 3HHH) = 5.5, 4HH = 1.1), 8.40 (dd, 1H, 3HH = 8.1, 4HH = 1.1), 8.20 (d, 1H, 3HH = 8.8), 8.17 (dd, 1H, 3HH = 8.1, 3HH = 5.5), 8.07 (d, 2H, 3HHH = 7.5), 7.98 (d, 1H, 3HHH = 8.8), 7.97 (s, 2H), 7.79 (dd, 1H, 3HH = 8.1, 4HH = 1.1), 7.56 (td, 2H, 3HHH); = 7.5, 4HH = 1.5), 7.48 (d, 2H, 3HH = 7.5, 4HH = 1.1), 7.28 (dd, 1H, 3HH = 5.5, 4HH = 1.1), 7.08 (dd, 1H, 3HHH = 8.1, 4HHH = 5.5), 6.68 (td, 2H, 3HH = 7.3, 4HH = 2.1), 2.73 (s, 3H), 2.39 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 171.2, 155.3, 153.1, 148.05, 142.7, 135.5, 132.5, 132.0, 131.1, 130.2, 128.7, 127.8, 127.5, 126.3, 124.3, 122.0, 119.2, 21.0, 3.58 (ODC 11): 10s (bpy) (NC1V1e) (1VIe-N) A procedure similar to that for obtaining ODC 10 using a 2,2'-bipyridine ligand in place of 1,10-phenanthroline (65% yield).

Anal. calc. for C29H24F6N5POs: C, 44.79; H, 3.11; N, 9.00. Found: C, 44.45; H, 3.08; N, 8.95 MS (ES, m / z): Calc. for C29H24N5192O6 634.1647 (M); Found: 634.166 IR (cm-1): 2244 (weak, vNC), 830 (intense, vPF), 575 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.53 (d, 1H, 3HHH = 5.7 ), 8.48 (d, 1H, 3HH = 8.2), 8.20 (d, 1H, 3HH = 8.2), 8.07 (dd, 2H, 3HH = 8.4, 4HH = 1.6), 7.95 (s, 2H), 7.87 (td, 1H, 3HH = 8.2, 4HH = 1.5), 7.76 (td, 1H, 3HH = 5.7, 4HH = 1.5), 7.57-7.64 (m, 4H), 7.30 (dd, 1H, 3HH = 8.2, 4HH = 1.5), 6.99 (d, 1H, 3HH = 5.7), 6.83 (td, 2H, 3HH = 8.4, 4HH = 1.5), 6.68 (td, 1H, 3HH = 5.7, 4HH = 1.5), 2.69 (s, 3H), 2.31 ( s, 3H) 13C {H} NMR (78 MHz, CD3CN, 300K): 153.8, 152.9, 147.6, 142.7, 135.6, 132.8, 132.2, 127.5, 125.6, 124.3, 123.5, 122.7, 122.2, 119.3, 21.0, 3.51 (ODC 12): 10s (tpy) (NC1V1e) (1VIe-N2CN) 1PF6P F6 ODC 12 Similar procedure as for obtaining ODC 10, using a ligand 2,2 '; 6', 2 "- terpyridine in place of 1,10-phenanthroline (65% yield) Anal calc for C32H24F6N5POs: C, 47.23, H, 2.97, N, 8.61 Found: C, 46.93, H, 2.98, N, 8.61 MS (ES, m / z): Calcd for C32H24N5192Os: 670.1647 (M); Found: 670. 163 IR (cm-1): 836 (intense, vPF), 560 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.70 (d, 2H, 3HH = 8.0), 8.41 (d, 2H, 3HHH) = 8.2), 8.22 (s, 2H), 8.12 (d, 2H, 3HH = 8.2), 7.70 (t, 1H, 3HH = 8.0), 7.55 (td, 2H, 3HH = 8.5, 4HH = 1.5), 7.45 ( td, 2H, 3HH = 8.5, 4HH = 1.5), 7.55 (d, 2H, 3HH = 5.5), 6.88 (td, 2H, 3HH = 5.5, 4HH = 1.5), 6.76 (d, 2H, 3HHH = 5.5), 6.51 (td, 2H, 3HH = 5.5, 4HH = 1.5), 2.90 (s, 3H) 13C (1H) NMR (78 MHz, CD3CN, 300K): 170.8, 160.7, 155.3, 152.7, 151.8, 139.8, 134.9, 133.9, 129.5, 127.0, 124.3, 123.5, 121.3, 120.7, 119.6, 20.8 (ODC 13): 10s (4'-methoxycarbonyl) -2,2 ': 6', 2 "-terpyridine) (Me-N ^C ^N) ) Procedure similar to that for obtaining ODC 10, using a 4'-methoxycarbonyl-2, 2 ': 6', 2 "-terpyridine ligand in place of 1,10-phenanthroline. The reaction time is 72h instead of 48h (65% yield). Anal. calc. for C34H26F6N5O2POs: C, 46.84; H, 3.01; N, 8.03. Found: C, 46.78; H, 3.01; N, 8.05 MS (ES, m / z): Calc. for C34H26N5O2192O5: 728.1701 (M); Found: 728.163 IR (cm-1): 1700 (mean vC = O), 836 (intense, vPF), 570 (average, vPF) 11I NMR (300 MHz, CD3CN, 300K): 9.10 (s, 2H), 8.59 (d, 2H, 3HHH = 8.1), 8.25 (s, 2H), 8.13 (d, 2H, 3HH = 8.1), 7.61 (td, 2H, 3HHH = 8.1, 4HH = 1.4), 7.45 (td, 2H, 3HHH); = 8.1, 4HH = 1.4), 7.18 (d, 2H, 3HH = 5.5), 6.98 (td, 2H, 3HH = 5.5, 4HH = 1.3), 6.69 (d, 2H, 3HH = 5.5), 6.49 (td, 2H) , 3HH = 5.5.4JHH = 1.3), 4.13 (s, 3H), 2.90 (s, 3H) 13C (rH) NMR (78 MHz, CD3CN, 300K): 171.7, 162.0, 157.0, 153.5, 153.0, 140.6, 138.2 , 136.9, 136.0, 131.9, 128.6, 128.4, 125.9, 125.0, 122.9, 122.7, 121.2, 54.0, 22.0, 15.2 (ODC 14): 10s (4'-ethoxycarbonyl) -2,2 ': 6', 2 "-terpyridine (Procedure) similar to that for obtaining ODC 10, using a 4'-ethoxycarbonyl-2, 2 ': 6', 2 "-terpyridine ligand in place of the 1 10-phenanthroline. The medium is stirred under reflux of dichloromethane (yield 45%). Anal. calc. for C35H28F6N5O2POs: C, 47.46; H, 3.19; N, 7.91. Found: C, 47.35; H, 3.33; N, 7.97 MS (ES, m / z): Calc. for C35H28N5O2192O5: 742.1858 (M); Found: 743.187 IR (cm-1): 1695 (mean vC = O), 834 (intense, vPF), 572 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.10 (s, 2H), 8.60 (d, 2H, 3HH = 8.2), 8.25 (s, 2H), 8.13 (d, 2H, 3HH = 8.2), 7.61 (td, 2H, 3HH = 8.2, 4HH = 1.5), 7.45 (td, 2H, 3HHH); = 8.2, 4HH = 1.5), 7.18 (d, 2H, 3HH = 5.9), 6.99 (td, 2H, 3HH = 5.9, 4HH = 1.5), 6.69 (d, 2H, 3HH = 5.9), 6.49 (td, 2H) , 3HH = 5.9, 4HH = 1.5), 4.59 (q, 3HH = 7.1), 2.92 (s, 3H), 1.56 (3H, t, 3HH = 7.1) 13C (H) NMR (78MHz, CD3CN, 300K) 171.8, 166.4, 163.2, 157.0, 153.5, 143.9, 141.8, 136.9, 136.0, 130.7, 128.9, 128.5, 125.9, 125.0, 122.9, 122.8, 121.2, 63.3, 32.9, 22.0, 15.2 (ODC15): 10s (trimethy12, 2 ': 6'2 "-terpyridine-4-4'-4" tricarboxylate) (1H-N-C-N) 1PF6; ODC Procedure similar to that for obtaining ODC 10, using a 2,2 ': 6', 2 "-terpyridine-4-4'-4" -tricarboxylate trimethyl ligand in place of 1,10-phenanthroline. The reaction time is 72h instead of 48h (25% yield). Anal. calc. for C38H30F6N5O6POs: C, 46.20; H, 3.06; N, 7.09. Found: C, 46.10; H, 3.08; N, 7.12 MS (ES, m / z): Calc. for C38H30N5O6192O4: 844.1811 (M); Found: 844.184 IR (cm-1): 1695 (mean vC = O), 828 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.35 (s, 2H), 9.07 (s, 2H), 8.26 (s, 2H), 8.12 (d, 2H, 3HH = 8.1), 7.61 (td, 2H, 3HH = 7.1.4HH = 1.6), 7.45 (d, 2H, 3HHH = 8.1), 7.38 (dd, 2H, 3HH = 7.1, 4HH = 1.6), 6.54 (d, 2H, 3HH = 7.1), 6.46 (ddd, 2H, 3HH = 7.1, 4HH = 1.6), 4.16 (s, 3H), 3.91 (s, 6H), 2.97 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 178.6, 166.4, 163.2, 157.0, 153.5, 145.4, 141.8, 136.9, 132.0, 130.7, 128.9, 128.5 , 125.9, 125.0, 122.9, 122.8, 121.2.99.4, 63.3, 56.4, 46.5, 32.9, 22.0, 15.2 (ODC 16): 10s (4 '- (4-methylphenyl) -2,2': 6 ', 2 " The procedure is similar to that for obtaining ODC 10, using a trimethyl 4 '- (4-methylphenyl) -2,2': 6 ', 2 "-terpyridine ligand (MeN 2 C-N) 1PF 6 G ODC 16 PFP. instead of 1,10-phenanthroline. The reaction time is 72h instead of 48h (60% yield). Anal. calc. for C39H30F6N5POs: C, 51.82; H, 3.35; N, 7.75. Found: C, 51.57; H, 3.34; N, 7.80 MS (ES, m / z): Calc. for C39H30N5192O5: 760.2116 (M); Found: 760.212 IR (cm-1): 837 (intense, vPF), 575 (average, vPF) 11I NMR (300 MHz, CD3CN, 300K): 8.98 (s, 2H), 8.56 (d, 2H, 3JHH = 8.2 ), 8.24 (s, 2H), 8.14 (d, 2H, 3HH = 8.2), 8.07 (d, 2H, 3HH = 8.1), 7.58 (td, 2H, 3HHH = 8.1.4JHH = 1.3), 7.53 (d, 2H, 3HH = 8.1), 7.46 (td, 2H, 3HH = 8.1, 4HH = 1.3), 7.10 (d, 2H, 3HH = 5.6), 6.89 (td, 2H, 3HHH = 8.1.4JHH = 1.3), 6.84 ( d, 2H, 3HH = 5.6), 6.52 (td, 2H, 3HH = 8.1.4JHH = 1.3), 2.92 (s, 3H), 2.53 (s, 3H) 13C (rH) NMR (78MHz, CD3CN, 300K) 171.6, 161.7, 155.6, 151.8, 134.9, 133.9, 129.9, 127.7, 127.0, 124.1, 123.6, 121.3, 119.7, 118.3, 117.3, 63.7, 59.8, 20.7, 20.3 (ODC 17): 10s (4'-methoxycarbonyl) 2.2 ': 6', 2 "-terpyridine) (MeO 2 C-N 2 C 4 N) 1PF 6 PFP ODC 17 Procedure similar to that for obtaining ODC 7, using a 4'-methoxycarbonyl-2, 2 'ligand: 6 2-terpyridine in place of 1,10-phenanthroline. The reaction time is 72h instead of 48h (45% yield). Anal. calc. for C35H26F6N5O4POs: C, 45.90; H, 2.86; N, 7.65. Found: C, 45.56; H, 2.91; N, 7.69 MS (ES, m / z): Calc. for C35H26N5O4192Os: 772.1600 (M); Found: 772.157 IR (cm-1): 1705 (mean vC = O), 835 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.14 (s, 2H), 8.93 (s, 2H), 8.59 (d, 2H, 3HH = 8.1), 8.29 (d, 2H, 3HH = 8.1), 7.61 (td, 2H, 3HH = 8.1, 4HH = 1.4), 7.52 (td, 2H, 3HHH). = 8.1, 4HH = 1.4), 7.16 (d, 2H, 3HH = 5.5), 6.95 (td, 2H, 3HH = 5.5, 4HH = 1.3), 6.82 (d, 2H, 3HH = 5.5), 6.61 (td, 2H) , 3HH = 5.5, 4HH = 1.3), 4.14 (s, 3H), 4.05 (s, 3H) 13C (1H) NMR (78 MHz, CD3CN, 300K): 169.6, 163.2, 159.9, 155.7, 152.1, 151.3, 135.9, 135.2, 127.2, 124.5, 123.9, 122.2, 121.5, 120.3, 54.3, 51.6, 48.9 (ODC 18): 10s (4'-ethoxycarbonyl) -2,2 ': 6', 2 "-terpyridine) (MeO2C-N) A procedure similar to that for obtaining ODC 7, using a 4'-ethoxycarbonyl-2, 2 ': 6', 2 "-terpyridine ligand in place of 1,10-phenanthroline. The medium is stirred at reflux of dichloromethane for 72h instead of 48h (10% yield). Anal. calc. for C36H28F6N5O4POs: C, 46.50; H, 3.04; N, 7.53. Found: C, 46.40; H, 3.07; N, 7.58 MS (ES, m / z): Calc. for C36H28N5O4192O5: 786.1756 (M); Found: 786.174 IR (cm-1): 1698 (mean vC = O), 836 (intense, vPF), 575 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.14 (s, 2H), 8.93 (s, 2H), 8.61 (d, 2H, 3HHH = 8.2), 8.30 (d, 2H, 3HH = 8.2), 7.62 (td, 2H, 3HH = 8.2, 4HH = 1.5), 7.53 (td, 2H, 3HHH); = 8.2.4HH = 1.5), 7.16 (d, 2H, 3HH = 5.5), 6.95 (td, 2H, 3HH = 5.5, 4HH = 1.5), 6.83 (d, 2H, 3HH = 5.5), 6.61 (td, 2H) , 3HH = 5.5, 4HH = 1.5), 4.61 (q, 3HH = 7.1), 4.05 (s, 3H), 1.56 (3H, t, 3HH = 7.1) 13C (H) NMR (78MHz, CD3CN, 300K) : 171.8, 166.4, 163.2, 158.7, 155.7, 152.2, 137.9, 138.8, 135.8, 135.1, 136.0, 130.7, 128.9, 127.1, 124.7, 124.4, 123.9, 122.1, 121.4, 120.3, 106.4, 62.1, 51.5, 19.9 (ODC 19): [0s (trimethyl 2,2 ': 6'2 "-terpyridine-4-4'-4" tricarboxylate) (1VIe02C-N'UN)] PF6 PFP ODC 19 Procedure similar to that for obtaining ODC 7, in using a 2,2 ': 6', 2 "-terpyridine-4-4'-4" tricarboxylate trimethyl ligand in place of 1,10-phenanthroline. The reaction time is 72h instead of 48h (45% yield). Anal. calc. for C39H30F6N5O8POs: C, 45.39; H, 2.93; N, 6.79. Found: C, 45.76; H, 3.31; N, 6.88 MS (ES, m / z): Calc. for C39H30N5O8192O5: 888.1709 (M); Found: 888.167 IR (cm-1): 1695 (mean vC = O), 834 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.37 (s, 2H), 9.07 (s, 2H), 9.06 (s, 2H), 8.95 (s, 2H), 8.29 (d, 2H, 3HH = 8.1), 7.55 (td, 2H, 3HHH = 7.3.4JHH = 1.6), 7.42 (d, 2H, 3HH = 8.1), 7.33 (dd, 2H, 3HH = 7.3, 4HH = 1.6), 6.69 (d, 2H, 3HH = 7.3), 6.59 (d td, 2H, 3HHH = 7.3, 4HH = 1.6), 4.17 (s, 3H), 4.05 (s, 3H), 3.91 (s, 6H) 13C (rH) NMR (78 MHz, CD3CN, 300K): 181.7, 167.4, 162.5, 157.5, 153.9, 141.0, 138.0, 128.2, 127.1 124.5, 123.8, 123.0, 121.9, 120.6, 115.5, 54.2, 54.0, 53.0, 15.8 (ODC 20): 10s (4 '- (4-methylphenyl) -2,2': 6 ', 2 "-terpyridine) ( MeO2C-N4C1N) 1PF6 PFP ODC Procedure similar to that for obtaining ODC 7, using a 2,2 ': 6', 2 "-terpyridine-4-4'-4" tricarboxylate trimethyl ligand instead 1,10-Phenanthroline The reaction time is 72h instead of 48h (65% yield) Anal Calcd for C40H30F6N5O2POs: C, 50.68, H, 3.19, N, 7.39 Found: C, 50.19; H, 3.25, N, 7.50 MS (ES, m / z): Calc for C4 0H30N5O2192Os: 804.2014 (M); Found: 804.199 IR (cm-1): 835 (intense, vPF), 572 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.99 (s, 2H), 8.91 (s, 2H), 8.57 ( d, 2H, 3HH = 8.2), 8.31 (d, 2H, 3HH = 8.2), 8.06 (d, 2H, 3HH = 8.1), 7.59 (td, 2H, 3HHH = 8.1, 4HH = 1.3), 7.55 (d, 2H, 3HHH = 8.1), 7.53 (td, 2H, 3JHH = 8.1, 4HH = 1.3), 7.07 (d, 2H, 3./11E1 = 5.6), 6.99 (d, 2H, 3HHH = 5.6), 6.86 (td , 2H, 3HH = 8.1, 4HH = 1.3), 6.66 (td, 2H, 3HH = 8.1.4JHH = 1.3), 4.04 (s, 3H), 2.54 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 171.6, 161.7, 156.9, 153.7, 153.3, 141.2, 136.7, 136.0, 131.4, 129.1, 128.4, 125.7, 125.2, 123.5, 121.5, 119.9, 51.5, 41.0 (ODC 21): [Os (NCMe) 3 (MeO 2 C -N 2 C 4 N)] PF 6 PF 6 ODC 21 Methyl-3,5- (2-pyridyl) benzoate (85 mg, 0.294 mmol) is added to a suspension of [OsCl (p-Cl) (r). / 6-C6H6)] 2 (100 mg, 0.147 mmol), NaOH (12 mg, 0.294 mmol) and KPF6 (91 mg, 0.588 mmol) in 10 mL of acetonitrile. The medium is stirred under reflux for 72 hours under irradiation of an incandescent lamp (60W). After evaporation of the solvents and volatile products, the dark residue is dissolved in 10 ml of CH 2 Cl 2 and then is filtered through Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The yellow fraction is collected and concentrated to about 1 mL. The addition of 10 mL of diethyl ether causes the precipitation of a yellow solid (164 mg, 75%). Anal. calc. for C24H22F6N5O2P05: C, 38.55; H, 2.97; N, 9.37. Found: C, 38.54; H, 3.01; N, 9.43 MS (ES, m / z): Calc. for C24H22N5O2192O5: 604.1388 (M); Found: 604.143 IR (cm-1): 2258 (average, v1 TC), 1686 (average, vC = O), 830 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K ): 8.98 (d, 2H, 3HH = 5.5), 8.43 (s, 2H), 8.19 (d, 2H, 3HH = 8.0), 7.84 (td, 2H, 3HHH = 8.0, 4HH = 1.5), 7.33 (td, 2H, 3HH = 5.5.4JHH = 1.5), 3.93 (s, 3H), 1.98 (s, 3H), 1.97 (s, 6H) 13C (H) NMR (78 MHz, CD3CN, 300K): 226.2, 168.9, 168.3, 154.7, 146.6, 137.5, 123.7, 123.6, 122.7, 120.3, 52.4, 3.27 (ODC 22): 10s (NCMe) 3 (Me-N2 C4 N) 1 PF6 PF? ODC 22 3,5-di (2-pyridyl) toluene (73 mg, 0.294 mmol) is added to a suspension of [OsCl (p-Cl) (r / 6-C6H6)] 2 (100 mg, 0.147 mmol) , NaOH (12 mg, 0.294 mmol) and KPF6 (91 mg, 0.588 mmol) in 10 mL of acetonitrile. The medium is stirred under reflux of acetonitrile for 72 hours under irradiation of an incandescent lamp (60W). After evaporation of the solvents and volatile products, the residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The yellow fraction is collected and then concentrated to 1 mL. The addition of 10 mL of diethyl ether causes the precipitation of a yellow solid (151 mg, 73%). Anal. calc. for C23H22F6N5POs: C, 39.26; H, 3.15; N, 9.95. Found: C, 39.16; H, 2.35; N, 9.86 MS (ES, m / z): Calc. for C23H22N5192O5: 560.1490 (M); Found: 560.153 IR (cm-1): 2240 (average, v1 TC), 827 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.99 (d, 2H, 3HHH) = 5.5), 8.00 (d, 2H, 3HH = 8.2), 7.76 (td, 2H, 3HH = 8.0, 4HH = 1.5), 7.74 (s, 2H), 7.24 (td, 2H, 3HH = 5.5, 4JHH = 1.5) ), 2.59 (s, 3H), 2.00 (s, 3H), 1.96 (s, 6H) 13C (H) NMR (78 MHz, CD3CN, 300K): 171.2, 155.3, 151.9, 145.6, 140.0, 135.8, 128.7 , 123.4, 122.7, 120.0, 118.7, 112.2, 20.8, 2.61 (ODC 23): 10s (NCMe) 3 (N1 N- (EtO2C) 4C) 1PF6G PF6 ODC 23 4-Ethoxycarbonyl-6-phenyl- 2,2'-bipyridine (179 mg, 0.588 mmol) is added to a suspension of [OsCl (p-Cl) (r / 6-C6H6)] 2 (200 mg, 0.294 mmol), NaOH (24 mg, 0.588 mmol) and KPF6 (108 mg, 0.588 mmol) in 10 mL of acetonitrile. The medium is stirred under reflux for 72 hours under irradiation of an incandescent lamp (60 W). After evaporation of the solvents and volatile products, the residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The orange / brown fraction is collected and then concentrated to 1 mL. Addition of 10 mL of diethyl ether causes the precipitation of a brown solid (110 mg, 25%). Anal. calc. for C25H24F6N5O2POs: C, 39.42; H, 3.18; N, 9.19. Found: C, 39.56; H, 3.38; N, 9.09 MS (ES, m / z): Calc. for C25H24N5O2192O6: 618.1545 (M); Found: 618.154 IR (cm-1): 1700 (mean vC = O), 2238 (average, v1 TC), 828 (intense, vPF), 570 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K) : 8.89 (d, 1H, 3HH = 5.5), 8.41 (d, 1H, 3HH = 8.1), 8.18 (m, 2H), 7.79 (td, 1H, 3HHH = 8.1, 4HH = 1.5), 7.46-7.51 (m.p. , 3H), 7.39 (td, 1H, 3HH = 6.1, 4HH = 1.5), 7.30 (td, 1H, 3HH = 6.1, 4HH = 1.5), 4.35 (q, 2H, 3HH = 7.1), 2.75 (s, 3H). ), 2.29 (s, 6H), 1.37 (t, 3H, 3HH = 7.1) 13C (H) NMR (78 MHz, CD3CN, 300K): 153.5, 141.0, 138.0, 130.1, 129.4, 127.0, 125.2, 122.1, 61.8, 15.2, 5.1, 4.2 (ODC 24): 10s (NCMe) 3 ((1VIeO2C) ^ N- (1VIeO2C) ^ NC) 1PF6 N -pF6 N ODC 24 4,4'-Di (methoxycarbonyl) -6 phenyl-2,2'-bipyridine (204 mg, 0.588 mmol) is added to a suspension of [OsCl (p-Cl) (r / 6-C6H6)] 2 (200 mg, 0.294 mmol), NaOH (24 mg, 0.588 mmol) and KPF6 (108 mg, 0.588 mmol) in 10 mL of acetonitrile. The medium is stirred under reflux for 72 hours under the irradiation of an incandescent lamp (60W). After evaporation of the solvents and volatile products, the residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCM). The orange / brown fraction is collected and then concentrated to 1 mL. The addition of 10 mL of diethyl ether causes the precipitation of a brown solid (118 mg, 25%). Anal. calc. for C26H24F6N5O4P0s: C, 38.76; H, 3.00; N, 8.69. Found: C, 38.96; H, 3.10; N, 8.75 MS (ES, m / z): Calc. for C26H24N5O4192Os: 662.1443 (M); Found: 662.144 IR (cm-1): 2240 (average, v1 TC), 1700 (mean vC = O), 827 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K) : 9.08 (d, 1H, 3HH = 5.9), 8.75 (d, 1H, 3HH = 2.0), 8.17 (m, 2H), 7.67 (dd, 1H, 3HH = 5.9, 3HHH = 2.0), 7.48-7.56 (m.p. , 3H), 7.41 (td, 1H, 3HH = 7.1), 4.0 (s, 3H), 3.9 (s, 3H), 2.79 (s, 3H), 2.28 (s, 6H), 13C (H) NMR (78), MHz, CD3CN, 300K): 155.8, 142.5, 139.0, 128.2, 129.5, 126.0, 124.8, 121.2, 68.5, 62.3, 15.8, 18.4, 5.3, 4.5 (ODC 26): 10s (16-C6H6) (NC1VIe) (3) , N, N-dimethyl-4- (pyridin-2-yl) benzenamine (200 mg, 1.010 mmol) is added to a suspension [OsCl (p-Cl) (r / 6-C6H6)] 2 (343 mg, 0.504 mmol), NaOH (40 mg, 1.010 mmol) and KPF6 (371 mg, 2.010 mmol) in 50 mL of acetonitrile. . The medium is stirred at 40 ° C. for 48 h. After evaporation of the solvents and volatile products, the residue is dissolved in 20 ml of CH 2 Cl 2. Then filtered through filtered on A1203 (10: 1 CH2C12 / NCMe). The yellow fraction is collected and then concentrated to about 5 mL. The addition of diethyl ether causes the precipitation of a yellow solid (489 mg, 75%). Anal. calc. for C21H122F6N3P05: C, 38.71; H, 3.40; N, 6.45. Found: C, 38.60; H, 3.42; N, 6.40 MS (ES, m / z): Calc. for C21H22N31920s: 508.1429 (M); Found: 508.145 IR (cm-1): 2289 (low, v1 TC), 836 (intense, vPF), 562 (medium, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.01 (d, 1H, 3HHH) = 5.9), 7.69-7.78 (m, 2H), 7.61 (d, 1H, 3HH = 8.8), 7.35 (d, 1H, 3HH = 2.6), 6.97 (td, 1H, 3HH = 6.2, 4HH = 2.4), 6.51 (dd, 1H, 3HH = 8.8, 3HH = 2.6), 5.73 (s, 6H), 3.07 (s, 6H), 2.22 (s, 3H) 13C (1H) NMR (78MHz, CD3CN, 300K): 168.8, 160.8, 157.0, 153.4, 139.5, 134.7, 127.0, 122.9, 121.8, 120.4, 119.2, 109.5, 81.1, 40.9 pF6 (ODC 27): 10s (16-C6H6) (NCMe) 1 (2-phenyl) -4- aminopyridine-KC, N) PF 6 H 2 N ODC 27 PFP 4-Amino-2-phenylpyridine (300 mg, 1.762 mmol) is added to a suspension of [OsCl (p-Cl) (17-C6H6)] 2 (599 mg 0.881 mmol), NaOH (70 mg, 1.762 mmol) and KPF6 (649 mg, 3.525 mmol) in 50 mL of acetonitrile. The medium is stirred at 40 ° C. for 48 h. After evaporation of the solvents and volatile products, the residue is dissolved in 20 ml of CH 2 Cl 2 and then filtered through Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The yellow fraction is collected and then concentrated to 5 mL. Addition of 50 mL of diethyl ether causes precipitation of a yellow solid (768 mg, 70%). Anal. calc. for C 19 H 18 F 6 N 3 PO 5: C, 36.60; H, 2.91; N, 6.74. Found: C, 36.32; H, 2.87; N, 6.69 MS (ES, m / z): Calc. for C19H18N31920s: 480.1116 (M); Found: 480.110 IR (cm-1): 2289 (low, TC), 836 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.58 (d, 1H, 3HHH) = 6.6), 8.01 (d, 1H, 3HH = 8.8, 4HH = 2.0), 7.60 (d, 1H, 3HH = 8.8, 4HH = 2.0), 7.04-7.14 (m, 3H), 6.43 (dd, 1H, 3HHH) = 6.6, 3HH = 2.0), 5.67 (s, 6H), 5.45 (s, 6H), 2.22 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 167.4, 158.3, 157.3, 156.9; , 147.3, 140.9, 131.2, 124.9, 124.7, 110.3, 104.5, 80.6 (ODC 28): 10s (phen) 2 (3,6-C6H3NMe2-2-py-KC, N) 1PF6 PF? ODC A solution of ODC 26 (100 mg, 0.153 mmol) in the presence of 1,10-phenanthroline (61 mg, 0.307) in methanol (10 mL) is stirred at reflux for 48 h. After evaporation of the solvents and volatile products, the brown residue is dissolved in 10 ml of CH2Cl2 and then filtered on Al2O3 (10: 0.5 CH2Cl2 / NCMe). The purple fraction is collected and then evaporated to dryness. Recrystallization of this solid from a mixture of CH 2 Cl 2 / pentane or acetone / pentane (slow diffusion) causes the precipitation of purple crystals which are then washed with diethyl ether and then dried under vacuum (87 mg, 65%).

Anal. calc. for C37H26F6N6POs: C, 49.77; H, 3.27; N, 9.41. Found: C, 49.53; H, 3.31; N, 9.41 MS (ES, m / z): Calcd. for C37H26N6192O4: 749.2069 (M); Found: 749.207 IR (cm-1): 836 (intense, vPF), 562 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.54 (d, 1H, 3HH = 5.2), 8.38 (d, 1H) , 3HH = 5.2), 8.23 (d, 1H, 3HH = 8.1), 8.09 (d, 2H, 3HH = 20.0), 8.01 (d, 2H, 3HH = 20.0), 9.91-8.14 (m, 5H), 7.75 ( dd, 1H, 3HH = 8.6, 4./1111=1.4), 7.62 (d, 1H, 3HH = 8.6), 7.58 (dd, 1H, 3HH = 5.2, 3HHH = 8.1), 7.49 (dd, 1H, 3 / HH = 5.2, 3HH = 8.1), 7.48 (dd, 1H, 3 / HH = 5.2, 3HH = 8.1), 7.36 (dd, 1H, 3HH = 8.6, 3HH = 1.4), 7.22 (dd, 1H, 3HHH = 5.2 , 3HH = 8.1), 7.19 (dd, 1H, 3HH = 8.6, 3HH = 1.4), 6.54 (dd, 1H, 3HH = 8.6, 4HH = 1.4), 6.19 (dd, 1H, 3JHH = 8.6, 3./11E1 = 2.4), 5.26 (d, 1H, 3HH = 2.4), 2.51 (s, 1H) 13C (1H) NMR (78 MHz, CD3CN, 300K): 156.3, 153.4, 153.3, 153.1, 152.7, 152.4, 151.9, 151.5, 151.3, 150.8, 145.4, 136.9, 136.6, 134.7, 133.6, 133.4, 133.3, 133.2, 132.4, 132.3, 132.2, 132.1, 132.0, 130.1, 129.9, 129.8, 129.7, 129.6, 129.4, 129.1, 129.0, 128.1, 128.0, 127.5, 121.4, 40.2, 31.2 (ODC 29): 10s (phen) 2 (4-amino-2-C6H4py-KC, N) 1PF6 PF? ODC 29 A solution of ODC 27 (100 mg, 0.160 mmol) in the presence of 1,10-phenanthroline (63 mg, 0.320) in methanol (10 mL) is stirred under reflux for 48 h. After evaporation of the solvents and volatile products, the brown residue is dissolved in 10 ml of CH2Cl2 and then filtered on Al2O3 (10: 0.5 CH2Cl2 / NCMe). The purple fraction is collected and then evaporated to dryness. Recrystallization of this solid from a mixture of CH 2 Cl 2 / pentane or acetone / pentane (slow diffusion) causes the precipitation of purple crystals which are then washed with diethyl ether and then dried under vacuum (91 mg, 66%). Anal. calc. for C35H25F6N6POs: C, 48.61; H, 2.91; N, 9.72. Found: C, 48.53; H, 3.04; N, 10.12 MS (ES, m / z): Calc. for C35H25N6192O5: 721.1756 (M); Found: 721.176 IR (cm-1): 836 (intense, vPF), 568 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.43 (d, 1H, 3HH = 5.5), 8.38 (d, 1H) , 3HH = 5.5), 8.19 (d, 1H, 3HH = 7.9, Ho), 8.38 (d, 1H, 3HH = 5.5), 8.07 (d, 4H, 3HHH = 19.6), 7.97 (d, 1H, 3HHH = 7.9 ), 7.94 (d, 2H, 3HHH = 7.9), 7.88 (d, 1H, 3HH = 5.5), 8.85 (d, 1H, 3HH = 5.5), 7.66 (m, 1H), 7.53 (dd, 1H, 3HHH = 5.5, 3HH = 7.9), 7.52 (dd, 1H, 3HH = 5.5, 3HH = 7.9), 7.43 (dd, 1H, 3HH = 5.5, 3HHH = 7.9), 7.21 (d, 1H, 3HH = 2.1), 7.17 ( dd, 1H, 3HH = 5.5, 3HH = 7.9), 6.72 (dd, 1H, 3HH = 6.4, 3HH = 2.1), 6.65 (m, 2H), 6.06 (dd, 1H, 3HH = 6.4, 4HH = 2.1), 5.84 (m, 1H) 13C {H) NMR (78 MHz, CD3CN, 300K): 169.8, 167.3, 156.1, 155.7, 154.0, 152.9, 152.6, 152.4, 151.8, 151.3, 150.9, 150.7, 150.3, 147.6, 141.3 , 136.2, 134.1, 133.4, 133.2, 132.4, 132.3, 132.1, 132.0, 129.9, 129.8, 129.4, 129.2, 129.0, 127.3, 127.1, 127.0, 124.6, 122.7, 110.1, 104.9 (ODC 30): 10s (terPY) ( NC1VIe) (3,6-C6H3N1VIe2-2-py-KC, N) 11T6 -ON Me2 pF6 ODC A solution of ODC 26 (100 mg, 0.153 mmol) The presence of 2,2 ', 6', 2 "-terpyridine (25 mg, 0.153) in acetonitrile (10 mL) is stirred at reflux for 72 h. After evaporation of the solvents and volatile products, the brown residue is dissolved in 10 mL of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 0.5 CH 2 Cl 2 / NCMe). The purple fraction is collected and then evaporated to dryness. Recrystallization of this solid from a mixture of CH 2 Cl 2 / pentane or acetone / pentane (slow diffusion) causes the precipitation of purple crystals which are then washed with diethyl ether and then dried under vacuum (74 mg, 60%). Anal. calc. for C30H27F6N6POs: C, 44.66; H, 3.37; N, 10.42. Found: C, 44.63; H, 3.40; N, 10.43 MS (ES, m / z): Calc. for C30H27N6192O6: 663.1912 (M); Found: 663.192 IR (cm-1): 836 (intense, vPF), 565 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.43 (d, 2H, 3JHH = 8.1), 8.28 (d, 2H) , 3JHH = 8.1), 8.00 (d, 2H, 3JHH = 5.3), 7.86 (d, 1H, 3JHH = 8.8), 7.68 (dd, 2H, 3JHH = 8.1, 3JHH = 5.6), 7.517.58 (m, 2H ), 7.35 (m, 1H), 7.22 (dd, 2H, 3HH = 5.6), 7.10 (t, 1H, 3HHH = 8.8), 6.40 (d, 1H, 3HH = 5.8), 6.33 (m, 1H), 7.10. (t, 1H, 3HH = 6.3), 3.16 (s, 6H), 2.12 (s, 3H) 13C (H) NMR (78 MHz, CD3CN, 300K): 163.6, 159.6, 149.5, 136.7, 135.8, 133.7, 130.1, 124.8, 121.9, 119.7, 117.6, 41.0, 4.2 (ODC31): 10s (4'-ethoxycarbonyl) -2,2 ': 6', 2 "-terpyridine (NCMe) (3,6-C6H3NMe2-2-py) KC, N) 1PF6 pF6 ODC 31 Procedure similar to that for obtaining ODC30, using 4'-ethoxycarbonyl2,2 ': 6', 2 "-terpyridine instead of 2,2 '; 6', 2" - terpyridine (55% yield) Anal Calcd for C33H31F6N6POs: C, 45.10, H, 3.56, N, 9.56 Found: C, 45.08, H, 3.65, N, 9.34 MS (ES, m / z): Calc. for C33H31N61920s: 735.2123 (M); Found: 735.211 IR (cm-1): 2260 (weak, vNC), 1702 (medium, vC); = O), 838 (intense, vPF), 555 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.81 (s, 2H), 8.47 (d, 2H, 3.HH), 7.99 (d, 2H, 3HHH = 5.1), 7.88 (d, 1H, 3HH = 8.8), 7.74 (dd, 2H, 3HH = 8.1, 3.HH = 5.1), 7.57 (d, 1H, 3HHH). = 7.9), 7.38 (m, 1H), 7.29 (dd, 2H, 3HH = 5.1, 3./HH = 8.1), 7.10 (dd, 1H, 3HH = 8.8, 3HHH = 7.9), 6.45 (m, 1H), 6.30 (d, 1H, 3HH = 5.3), 7.10 (dd, 1H, 3H11 = 7.9, 3./11E1 = 8.8), 4.55 (q, 2H, 3HH = 7.1), 3.17 (s, 6H). ), 2.11 (s, 3H), 1.52 (t, 3H, 3HH = 7.1) 13C (H) NMR (78 MHz, CD3CN, 300K): 163.2, 159.5, 158.0, 149.7, 137.3, 136.3, 132.3, 130.2, 125.1, 122.2, 119.7, 63.4, 41.0, 15.1, 4.2 (ODC 32): 10s (16-C6H6) (NCMe) (C6H4-oxazoline-KC, N) 11T6 pF6 Ose 1 \ 1, OJ ODC 32 From 2- phenyloxazoline (389 mg, 2.6 mmol) is added to a suspension of [OsCl (p-Cl) (p-cym)] (900 mg, 1.32 mmol), NaOH (105 mg, 2.64 mmol) and KPF6 (974). mg, 5.29 mmol) in 120 mL of acetonitrile. The reaction medium is stirred at 40 ° C. for 48 h. After evaporation of the solvents and volatile products, the residue is dissolved in 20 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The yellow fraction is collected and concentrated to 5 mL. Addition of 50 mL of diethyl ether causes precipitation of a yellow / brown solid (1144 mg, 72%). Anal. calc. for C17H17F6N2OPO5: C, 34.00; H, 2.85; N, 4.66. Found: C, 34.24; H, 2.88; N, 4.82 MS (ES, m / z): Calc. for C17H17N2O1920s: 457.0956 (M); Found: 457.094 IR (cm-1): 2258 (low, v1 TC), 1686 (medium, vC = 0), 836 (intense, vPF), 560 (medium, vPF) 111 NMR (300 MHz, CD3CN, 300K ): 8.05 (d, 1H, 3HH = 7.5), 7.42 (d, 1H, 3HH = 7.5), 7.22 (dd, 1H, 3HHH = 7.5), 7.09 (dd, 1H, 3HHH = 7.5), 5.71 (s, 6H), 4.83-4.91 (m, 2H), 4.834.91 (m, 2H), 4.12-4.22 (m, 1H), 3.93-4.03 (m, 1H) 13C (1H) NMR (78MHz, CD3CN, m.p. 300K): 187.4, 181.5, 173.8, 160.4, 141.1, 133.4, 132.6, 127.8, 124.8, 120.8, 80.0, 73.9, 56.7 (ODC 33): 10s (phen) (NCMe) 2 (C6H4-oxazoline-KC, N) 11 T6 pF6 ODC 33 A solution of ODC 32 (80 mg, 0.133 mmol) in the presence of 1,10-phenanthroline (26.5 mg, 0.133) in acetonitrile (10 mL) is stirred at reflux for 72 h. After evaporation of the solvents and volatile products, the residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The purple fraction is collected and then evaporated to dryness. Crystallization of this solid in a CH 2 Cl 2 / pentane mixture causes the precipitation of dark red crystals which are then washed with diethyl ether and then dried under vacuum (63 mg, 64%). Anal. calc. for C25H22F6N5OPOs: C, 40.38; H, 2.98; N, 9.42. Found: C, 40.48; H, 3.20; N, 9.35 MS (ES, m / z): Calc. for C25H22N5O92020: 600.1439 (M); Found: 600.144 IR (cm-1): 2258 (low, v1 TC), 840 (intense, vPF), 560 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.50 (d, 1H, 3HHH) = 5.1), 8.39 (dd, 1H, 3HH = 8.1, 4HH = 1.1), 8.25 (d, 1H, 3HH = 5.1), 8.11 (d, 1H, 3HHH = 8.8), 8.04 (d, 1H, 3HHH = 8.8 ), 8.03 (dd, 1H, 3JHH = 8.1, 4JHH = 1.1), 7.96 (dd, 2H, 3JHH = 8.1, 3JHH = 5.1), 7.37-7.42 (m, 2H), 7.24 (dd, 1H, 3JHH = 7.5 ), 7.24 (dd, 1H, 3HH = 7.5), 6.89 (dd, 1H, 3HH = 7.5), 4.49-4.58 (m, 1H), 4.18-4.28 (m, 1H), 4.12-4.23 (m, 1H) , 2.82 (s, 1H), 2.38 (s, 1H), 2.22-2.38 (m, 1H) 13C (1H) NMR (78 MHz, CD3CN, 300K): 183.5, 157.7, 154.6, 151.5, 150.8, 138.3, 135.7, 134.5, 132.1, 131.7, 131.5, 128.8, 128.7, 127.4, 127.0, 126.3, 71.8, 51.3, 5.0, 4.4 (ODC 34): 10s (phen) 2 (C6H4-oxazoline-KC, N) 1PF6 A solution of ODC 32 (80 mg, 0.133 mmol) in the presence of 1,10-phenanthroline (54 mg, 0.268) in methanol (10 mL) is stirred at reflux for 72 h. After evaporation of solvents and volatiles, the brown residue is dissolved in 10 mL of CH2Cl2 and then filtered through Al2O3 (10: 1 CH2Cl2 / NCMe). The purple fraction is collected and then evaporated to dryness. Crystallization of this solid in a CH 2 Cl 2 / pentane mixture causes the precipitation of dark red crystals which are then washed with diethyl ether and then dried under vacuum (94 mg, 84%). Anal. calc. for C33H24F6N5OPOs: C, 47.09; H, 2.87; N, 8.32. Found: C, 47.33; H, 3.13; N, 8.08 MS (ES, m / z): Calc. for C33H24N5O1920s: 698.1596 (M); Found: 698.160 IR (cm-1): 836 (intense, vPF), 560 (average, vPF) 111 NMR (300 MHz, CD3CN, 300K): 9.50 (d, 1H, 3HH = 5.5), 8.47 (d, 1H) , 3HH = 5.5), 8.18 (d, 1H, 3HH = 8.1), 8.01-8.16 (m, 7H), 7.99 (d, 1H, 3HH = 5.5), 7.95 (d, 1H, 3HHH = 8.1), 7.70 ( dd, 1H, 3HH = 8.1, 3HH = 5.5), 7.64 (dd, 1H, 3HH = 8.1, 3HH = 5.5), 7.41 (dd, 1H, 3HHH = 8.1, 3HHH = 5.5), 7.35 (dd, 1H, 3HHH) = 6.8, 4JHH = 2.2), 7.22 (dd, 1H, 3JHH = 8.1, 3JHH = 5.5), 6.63-6.71 (m, 2H), 6.03 (dd, 1H, 3JHH = 6.8, 4JHH = 2.2), 4.81-4.90 (m, 1H), 4.44-4.53 (m, 1H), 3.59-3.69 (m, 1H), 2.49-2.59 (m, 1H) 13C (H) NMR (78 MHz, CD3CN, 300K): 182.3, 146.9 , 154.3, 153.8, 153.1, 152.5, 152.3, 151.5, 151.4, 150.8, 150.7, 136.0, 135.8, 134.9, 134.3, 133.6, 132.9, 132.5, 132.2, 132.1, 132.0, 131.9, 129.2, 129.1, 129.0, 129.9, 127.9 , 127.3, 127.2, 127.1, 126.8, 121.8, 72.4 PF? G ODC 34; 1NN (ODC 35): 10s (C6H4-oxazoline-KC, N) (4'-ethoxycarbonyl) -2,2 ': 6', 2 "-terpyridine) (NCMe)] PF6 PF6e ODC 35 A solution of ODC 32 (80 mg, 0.133 mmol) in the presence of 4'-ethoxycarbonyl2,2 ': 6', 2 "-terpyridine (41 mg, 0.133) in acetonitrile (10 mL) is stirred at reflux for 72 h. . After evaporation of the solvents and volatile products, the brown residue is dissolved in 10 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The purple fraction is collected and then evaporated to dryness. Crystallization of this solid in a CH 2 Cl 2 / pentane mixture causes the precipitation of dark red crystals which are then washed with diethyl ether and then dried under vacuum (66 mg, 60%). Anal. calc. for C29H26F6N5O3P0s: C, 42.08; H, 3.17; N, 8.46. Found: C, 42.24; H, 3.21; N, 8.54 MS (ES, m / z): Calc. for C29H26N5O3192O6: 684.1650 (M); Found: 684.164 IR (cm-1): 2250 (low, v1 TC), 1685 (medium, vC = 0), 836 (intense, vPF), 560 (medium, vPF) 111 NMR (300 MHz, CD3CN, 300K ): 8.75 (s, 2H), 8.44 (d, 2H, 3HH = 8.2), 8.17 (d, 1H, 3./11E1 = 7.5), 7.97 (d, 2H, 3HH = 5.9), 7.76 (dd, 2H); , 3 JHH = 8.2, 3./11E1=5.9), 7.52 (d, 1H, 3./11E1=7.7), 7.44 (dd, 1H, 3 / HH = 7.5, 3./11E1=7.7), 7.35 ( dd, 2H, 3 / HH = 8.2, 3./11E1 = 5.9), 6.89 (dd, 1H, 3HH = 7.5, 3.HH = 7.7), 4.52 (q, 2H, 3HH = 7.1) , 4.21 (t, 2H, 3HH = 9.3), 2.17 (t, 2H, 3 / HH = 9.3), 2.11 (s, 3H), 1.50 (t, 3H, 3 / HH = 7.1) 13C (H) NMR (78 MHz, CD3CN, 300K): 182.8, 181.7, 165.5, 163.3, 159.2, 158.4, 137.1, 136.6, 132.7, 131.7, 130.5, 130.1, 127.7, 124.4, 121.9, 121.7, 71.7, 63.3, 48.4, 15.0, 4.2 (ODC 36): 10s (16-C6H6) (NCMe) (C6H4-imidazole-KC, N) 11T6 pF6 ODC 36 2-Phenylimidazole (382 mg, 2.6 mmol) is added to a suspension of [OsCl C1) (p-cym)] 2 (900 mg, 1.32 mmol), NaOH (105 mg, 2.64 mmol) and KPF6 (974 mg, 5.29 mmol) in 120 mL of acetonitrile. The reaction medium is stirred at 40 ° C. for 48 h. After evaporation of the solvents and volatile products, the residue is dissolved in 20 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The yellow fraction is collected and then concentrated to 5 mL. Addition of 50 mL of diethyl ether causes precipitation of a yellow / brown solid (640 mg, 45%). Anal. calc. for C 17 H 16 F 6 N 3 PO 5: C, 34.17; H, 2.70; N, 7.03. Found: C, 34.12; H, 2.71; N, 7.05 MS (ES, m / z): Calc. for C17H16N31920s: 454.0959 (M); Found: 454.098 IR (cm-1): 2258 (low, v1 TC), 835 (intense, vPF), 565 (intense, vPF) 111 NMR (300 MHz, CD3CN, 300K): 8.03-8.05 (m, 1H) ), 7.52-7.55 (m, 1H), 7.36 (d, 1H, 3HH = 1.7), 7.15 (d, 1H, 3HH = 1.7), 7.08-7.11 (m, 2H), 5.70 (s, 6H), 2.18 (m, 1H), 1.96 (s, 3H) 13C (1H) NMR (78 MHz, CD3CN, 300K): 159.9, 156.1, 141.3, 136.8, 131.7, 130.4, 125.0, 123.1, 119.0, 79.9 (ODC 37) 10s (16-C6H6) (NCMe) (C6H4-imidazoline-KC, N) 11T6-o PFee ODC 2-Phenylimidazoline (387 mg, 2.6 mmol) is added to a suspension of [OsCl (p-C1) (p-cym)] 2 (900 mg, 1.32 mmol), NaOH (105 mg, 2.64 mmol) and KPF6 (974 mg, 5.29 mmol) in 120 mL of acetonitrile. The reaction medium is stirred at 40 ° C. for 48 h. After evaporation of the solvents and volatile products, the residue is dissolved in 20 ml of CH 2 Cl 2 and then filtered on Al 2 O 3 (10: 1 CH 2 Cl 2 / NCME). The yellow fraction is collected and then concentrated to 5 mL. Addition of 50 mL of diethyl ether causes precipitation of a yellow / brown solid (1031 mg, 65%). Anal. calc. for C 17 H 18 F 6 N 3 PO 5: C, 34.06; H, 3.03; N, 7.01. Found: C, 34.16; H, 3.02; N, 7.07 MS (ES, m / z): Calc. for C17H18N31920s: 456.1116 (M); Found: 456.109 IR (cm-1): 2259 (low, v1 TC), 838 (intense, vPF), 565 (intense, vPF) 11I NMR (300 MHz, CD3CN, 300K): 8.02 (d, 1H, 3HHH) = 7.3), 7.35 (d, 1H, 3HHH = 7.3), 7.16 (dd, 1H, 3HHH = 7.3), 7.06 (dd, 1H, 3HHH = 7.3), 6.45 (m, 1H), 5.63 (s, 6H). , 3.79-4.12 (m, 4H), 1.96 (s, 3H) 13C (rH) NMR (78 MHz, CD3CN, 300K): 178.6, 161.0, 141.1, 136.6, 132.3, 126.5, 124.5, 79.6, 57.7, 47.1, 2.1 (ODC 38): 10s (16-C6H6) (2-C6H4-2-py-KC, N) (C1)]... COC ODC 38 The ODC 38 can be synthesized by following the protocol of reference 3. Another method was also developed: A suspension of [OsCl (p-C1) (r / 6-C6H6)] 2, (200 mg, 294 mmol), 2-phenylpyridine (100.3 mg 646 mmol) and sodium acetate (60 mg, 740 mmol) in 10 ml of CH 2 Cl 2 is stirred under reflux for 6 h The solution is filtered through Celite and evaporated to dryness The product is then recrystallized from CH 2 Cl 2 / pentane causing the appearance of yellow crystals which are washed with diethyl ether and then dried under vacuum (190 mg, 70%). Anal. calc. for C17H14ClNOS: C, 44.58; H, 3.08; N, 3.06. Found: C, 44.46; H, 3.07; N, 3.13 MS (ES, m / z): Calc. for C17H14ClN1920: 459.0430 (M); Found: 459.04011I NMR (300 MHz, CDCl3, 300K): 9.20 (d, 1H, 3HH = 5.2), 8.10 (d, 1H, 3HHH = 7.4), 7.79 (d, 1H, 3HHH = 8.1), 7.61-7.70 (m, 2H), 7.14 (dd, 1H, 3HH = 8.1), 6.98-7.06 (m, 2H), 5.54 (s, 6H) 13C (rH) NMR (78 MHz, CD3CN, 300K): 166.9, 165.7, 155.3, 144.4, 139.2, 137.3, 130.7, 124.4, 123.1, 122.5, 119.2, 77.6 (ODC 39): 10s (16-C6H6) (DMSO) (2-C6H4-2-py-KC, N)] PF6 PF? To a suspension of ODC 38 (100 mg, 0.22 mmol) in 5 mL of CH2Cl2 was added AgPF6 (56 mg, 0.22 mmol) and dimethyl sulfoxide (201.1E, 0.22 mmol). The medium is stirred at ambient temperature for 15 min and then filtered through Celite using CH 2 Cl 2. The pale yellow fraction is collected and then concentrated to 5 mL. The addition of 50 ML of pentane causes the precipitation of a beige solid (128 mg, 90%), which is washed with ether and dried under vacuum. Anal. calc. for C19H20F6NOPS05: C, 35.35; H, 3.12; N, 2.17. Found: C, 35.30; H, 3.01; N, 2.12 MS (ES, m / z): Calc. for C19H20NOS1920s: 502.0880 (M); Found: 502.089 IR (cm-1): 838 (intense, vPF), 562 (intense, vPF) 111 NMR (300 MHz, DMSO, 300K): 9.30 (d, 1H, 3HH = 5.4), 8.10 (d, 1H) , 3HH = 7.4), 7.92-8.04 (m, 3H), 7.29 (dd, 1H, 3HH = 7.9), 7.14-7.20 (m, 2H), 6.14 (s, 6H), 3.37 (s, 3H), 2.80 (s, 3H) 13 C (R H) NMR (78 MHz, DMSO, 300 K): 167.0, 156.9, 154.4, 145.9, 140.2, 139.3, 130.3, 125.0, 123.8, 123.5, 120.1, 50.5, 45.9 Example 2: Proliferation test compounds according to the invention on tumor cell lines Cells The products are tested on different cell lines. The cells used are the A172 line (human glioblastoma), the OVCAR3 (human ovarian cancer), the RIN m5F (rat insulinoma) and the HCT116 (human colon cancer). A172 cells are cultured in DMEM medium (PAN biotech) (DMEM (1%), NaHCO3 (25mM), Glucose (25.5mM), Glutamine (2mM), HEPES (10mM), pH 7.3 in H2O) containing 10% fetal bovine serum and 0.5% penicillin and streptomycin. OVCAR3 cells were cultured in RPMI-1640 medium (PAN biotech) (RPMI (10%), NaHCO3 (23.80mM) Glucose (2.7mM), insulin (60mM) Hepes (10mM), glutamine (2mM), 20% bovine fetal serum, 0.5% Gentamycin The RIN m5F cells are cultured in RPMI-1640 medium (PAN Biotech), 10% fetal bovine serum, 1% Penicillin-Streptavidin, HCT116 cells are cultured in DMEM medium (PAN biotech ), 10% fetal bovine serum, 1% PenicillinStreptavidin The cells are cultured at 37 ° C with a 5% CO2 atmosphere Proliferation test: MTT test This colorimetric test makes it possible to estimate the number of living cells via the quantification of their mitochondrial activity which converts the MTT substrate into Formazan by the action of mitochondrial dehydrogenases A172, RIN m5F and HCT116 cells are incubated for 48 hours and the OVCAR3 are incubated for 72 hours in 96-well plates (MicrotestTM 96, Falcon) in the presence of compounds to increasing concentrations. The medium is then replaced with 1001_11 of solution containing MTT (final concentration 0.5 mg / ml, Sigma M-2128). After one hour of incubation, the purple precipitates corresponding to Formazan are solubilized in 100 l of 0.04 N HCl / isopropanol and the plates are read at 550 nm (Model 680, Bio-Rad). Proliferation test of the A172 line with each compound The selection of the potential anti-cancer drugs is made, initially, on the A172 line. The effect of the various compounds derived from osmium on cell viability is first determined by a proliferation test as a function of product concentration. The activity of the compounds derived from Osmium is compared with that of cisplatin. The exposure of A172 cells to these derivatives results in a dose-dependent decrease in their proliferation. The effect therefore depends on the organic complex that surrounds the Osmium nucleus. The growth inhibition concentration of 50% of the cells (IC 50) at 1. μM is determined for each of the products (FIG. 2A). Figure 2B shows the diagrams of some ODCs from the 3 families of compounds described on the basis of their families of ligands. Of the compounds tested, ODCs 13, 16, 20 and 9 appear to be the most active with an IC50 of between 0.25 μM and 0.8 μM. Osmium derivatives showing too high IC50 (> 251.1M) were removed from the biological study. The RDC compounds are as follows: RDC 11: [Ruthenium (1,10-phenanthroline) bis- (acetonitrile) (2-phenylpyridyl, KC, N)] hexafluorophosphate RDC 36: [Ruthenium bis- (1,10-phenanthroline) ( N, N-dimethyl-4- (2-pyridinyl) aniline, KC, N)] hexafluorophosphate RDC 37: [Ruthenium bis- (1,10-phenanthroline) (2-phenylpyridyl, KC, N)] hexafluorophosphate RDC 49: [ Ruthenium (q6- (1-methyl-4- (1-methylethyl) benzene) (acetonitrile) (2-phenylpyridyl, KC, N)] hexafluorophosphate RDC 49-0: [Ruthenium (q6- (1-methyl-4- (1-methylethyl) benzene) (chloro) (2-phenylpyridyl, KC, N)] hexafluorophosphate RDC 49-DMSO: [Ruthenium (q6- (1-methyl-4- (1-methylethyl) benzene) (dimethyl) sulfoxide, KS) (2-phenylpyridyl, KC, N)] hexafluorophosphate RDC 54: [Ruthenium (2,2 ': 6', 2 "-terpyridine) (methyl 3,5-di (pyridin-2-yl) parabenzoate , KN, C, N)] hexafluorophosphate RDC 55: [Ruthenium (1,10-phenanthroline) (acetonitrile) (methyl 3,5-di (pyridin-2-yl) parabenzoate, KN, C, N)] Hexafluorophosphate phosphate RDC 56: [Ruthenium (1,10-phenanthroline) (acetonitrile) (2- (4-methyl-6- (pyridin-2-yl) phenyl) pyridyl, KN, C, N)] hexafluorophosphate RDC 57: [Ruthenium ([2,2 ', 6', 2 "-terpyridine] -4'-ethyl carboxylate) (methyl 6-phenyl- [2,2'-bipyridine] -4-carboxylate, KN, N, C) ] hexafluorophosphate Conclusion: The data of Figure 2A show that all of the compounds according to the invention have anticancer activity on the lines tested. In addition, the substitution of ruthenium with osmium is not sufficient to systematically increase the anticancer activity of the compounds according to the invention on this line. It therefore seems that the cytotoxic potential results from the association of metal and ligands. Proliferation assay on a large panel of human cancer lines On the basis of the IC50s obtained on the A172 line, the most active compounds are tested on a larger number of human cancer lines. At D-1, the cells are seeded in a 96-well plate at 5,000 and 40,000 cells / well depending on the proliferation rate of each line and incubated at 37 ° C / 5% CO2. At 0, the number of cells is counted in the control plate (C) and the test compounds are added to the other plates in the following concentration range: 10-8; 10-7; 10-6; 10-5; 10-4 M in quadruplicate -. At D + 2, the cells are fixed at 1 ° C. at 4 ° C. by adding TCA at the final concentration of 10%. The proliferation rate is correlated with the evaluation of the amount of protein. A solution of Sulforhodamine B 0.4% in 1% acetic acid is added to each well. The precipitate is resuspended in 10 mM Trisma Base and the absorbance is read at 515 nm. The cell growth rate is correlated with the cell number difference between J2 (Ti) and OJ (Tz) according to the following formulas: [(Ti-Tz) / (C-Tz)] X 100 for cell numbers where TiTz [(Ti-Tz) / Tz] X 100 for the numbers of cells where Ti <Tz For each indication studied, several cancer lines are tested. Table 2 summarizes 1050 AM for one line of each indication. These results demonstrate that the mere presence of the Osmium atom is not sufficient to induce the cytotoxic activity since within the same line, the effects are very variable from one compound to another: for example in the colorectal line HCT116, ODC19 and OCD13 have a 1050> 1 micromolar, while the other compounds are more active with 1050 <1 micromolar. In addition, for the same compound, the activities are specific from one line to another: for example ODC19 is more active on HL60 leukemia and MCF7 breast lines with a 1050 Micromolar, whereas it is less on the other lines with a 1050 micromolar. Finally, the substitution of the ruthenium metal with osmium alone, keeping the same ligands (RDC11 vs ODC2), shows a cytotoxic activity gain ranging from x2 (PC3 line) to x10 (MCF7 line). Conclusion: The compounds of the invention have anticancer activity on a large panel of human cancer lines. This panel offers a broader view of the impact of metal change and associated ligands. Example 3 In Vivo Safety Study of the Compounds According to the Invention on Black6 Mice In order to determine the concentrations to be administered during studies of cancer activity on tumors implanted in the mouse, tolerance studies based on the administration of Increasing concentrations of compounds of the invention are achieved. The 50μM ODC3-DMSO stock solution is stored at -20 ° C. The compounds are formulated in Cremophore EL (Fluka 27963) 10% - PBS extemporaneously to their intraperitoneal injection. Four groups of four 8 week old C57Black6 females receive 4 product concentrations (5 μmol / kg, 7.5 μmol / kg, 15 μmol / kg and 30 μmol / kg) according to the following scheme: ## EQU1 ## The behavior, weight and survival of the animals are evaluated twice a week. Figure 3 illustrates the survival of animals within each group. Conclusion: In acute toxicity, the maximum tolerated dose of ODC3 is between 7.5 and 15 μmol / kg and the lethal dose 50 is between 15 and 30 μmol / kg. In chronic treatment, the data show that the dose of 5 μmol / kg is tolerated at the rate of 2 injections / week. EXAMPLE 4 Study of the Anticancer Activity of the Compounds According to the Invention on Syngeneous Tumor Implanted Subcutaneously The anticancer activity of the compounds of the invention is determined by monitoring the slowing down of the growth of a syngeneic tumor induced by subcutaneous injection of 3LL cells (Lewis carcinoma). Tumor induction is achieved by injection of 120,000 3LL cells suspended in 0.5% Penicillin / Streptomycin DMEM on the flank of 8 week old C57 / Black6 females. After approximately 2 weeks, when the tumors reached an average of 80 mm 3, the mice are randomized in groups of 8 animals and receive either 30 μmol / kg of ODC4 or the formulation only (non-treated group) intraperitoneally 2x /week. Before each injection, the tumors are measured by an electronic caliper and the volume is determined according to the formula V (mm3) = axb2 / 2 where a = width (in mm) and b = length (in mm) of the tumor Figure 4 (top graph) shows the slowdown in the growth of a model of syngeneic lung tumor (3LL) treated with ODC4 versus untreated. Each point is the average of 8 tumors. The Treatment / Control ratio is 52% after 3 weeks of treatment, ie 35 days after the implantation of the cancer cells. The lower graph shows the volume distribution of each tumor after 3 weeks of treatment. The tumor volume of the ODC4 treated group is homogeneous and significantly lower compared to the untreated group, which presents tumors of more heterogeneous and globally larger volumes. Conclusion: In vivo, ODC4 demonstrated anticancer activity on an implanted tumor model. EXAMPLE 5 Study of the Interaction of the Compounds According to the Invention with the DNA In Vitro Interaction Between the Compounds of the Invention and of the Plasmid DNA In order to approach the mode of action of the compounds of the invention Invention, the ability of these to interact with DNA was tested using double-stranded plasmid DNA. These experiments were conducted compared to ruthenium equivalent derivatives (RDC11 for ODC2 and RDC34 for ODC3). The compounds were incubated overnight at room temperature with naked plasmid DNA with molar ratios of compounds for 10 base pairs ranging from 1 to 20. After incubation, the mixtures were deposited on 1% agarose gel. and migrated in an electric field until separation of the various forms of plasmid (supercoiled, cut, linear). The DNA is then labeled with ethidium bromide under a UV lamp. The interaction between the compounds and the plasmid DNA results in a slowing of the migration of the DNA on gel that can be induced by the formation of the heavier complex and / or by the induction of breakage in the supercoiled plasmid DNA. FIG. 6A shows that the ODC2 and ODC3 compounds slow down the migration of the plasmid DNA into the gel, indicating an interaction between these compounds and the DNA. This slowdown begins to be significant with a ratio of 2.5 molecules of ODC to 10 base pairs. Under the same experimental conditions, the equivalent ruthenium compounds have a significant effect from 5 molecules per 10 base pairs. Conclusion: The compounds of the invention interact in vitro with the plasmid DNA. Substitution of the ruthenium atom by the osmium atom seems to favor the interaction with DNA for the cases presented here. There is little difference between the ability of ODC2 and ODC3 to interact with DNA in vitro, whereas ODC3 is more cytotoxic. Thus, it is likely that the cytotoxic activity of the compounds of the invention does not depend solely on their ability to interact with the DNA, although this is likely to participate in the process. Study of the phosphorylation of the protein H2AX, a marker of damage to the DNA In order to understand the repercussions of an interaction between the compounds of the invention and the DNA, the phosphorylation of the protein H2AX was followed by western blot . Phosphorylation of H2AX is a recognized marker of the existence of DNA damage in a cell. HCT116 cells (colorectal cancer line) were treated with the various compounds for 16 hours and the proteins were extracted, separated on SDS acrylamide gel, transferred to nitrocellulose and identified using antibodies specific for the phosphorylated protein H2AX and for actin. Actin serves as a reference for the amounts of protein loaded on the gel. Figure 6B shows that the compounds ODC2 and ODC3 moderately induce phosphorylation of H2AX. Few differences are visible after treatment of the cells with the equivalent ruthenium compounds (RDC11 and RDC34). Conclusion: The compounds of the invention induce phosphorylation of the H2AX protein, suggesting that these compounds can induce DNA damage. The substitution of ruthenium with osmium does not seem to significantly affect this activity for the examples presented here. Study of the induction of damage to DNA in cancer cells treated with the compounds of the invention. In order to demonstrate the ability of the compounds of the invention to cause damage to the DNA of cancer cells, a so-called comet assay approach has been undertaken. This approach consists in evaluating the state of the genomic DNA of the cells. Cancer cells HCT116 were treated for one hour with ODC2, RDC11 or cisplatin (cis) at a concentration of 101.1M. After treatment, the cells are fixed and placed in a soft agarose gel. The set is then placed in an electric field. After a 30 minute migration, the DNA is labeled with propidium ionide. The damaged DNA comes out of the nucleus. Figure 6C shows that ODC2 very significantly increases the amount of DNA exiting the nucleus, indicating the presence of DNA damage. In addition, the amount of DNA released after treatment of cells with ODC2 is greater than that induced by RDC11 or by cisplatin. Conclusion: These results indicate that the compounds of the invention induce DNA damage in cancer cells. In addition, the replacement of the ruthenium atom not the osmium atom modifies the properties of the compounds with respect to their ability to interact with DNA and to induce DNA damage. Example 6 Study of the Regulation of Signaling Pathways Linked to Cell Metabolism Analysis of the Production of Oxygen-reactive Derivatives Since one of the particular characteristics of osmium-based compounds is their redox potential, the effect of these compounds on the production of oxygen-reactive derivatives has been studied. Indeed, it is possible that the redox properties of ruthenium compounds alter the activity of oxidoreductase enzymes involved in cell metabolism, thus leading to the production of oxygen reactive derivatives. To measure the production of these oxygen-reactive derivatives, a fluorescent probe (carboxy-H2DCFDA) was used. The HCT116 cells were treated at different times and concentrations of ODC before being incubated for 15 minutes with the fluorescent probe. The signal was then quantified with a fluorimeter. Menadione (men) was used as a positive control. Figure 7A shows that the compounds ODC2 and ODC3 induce the formation of oxygen reactive derivatives. In particular, ODC3 induces these radicals very significantly from 4 hours of treatment.

Conclusion: The compounds of the invention have the capacity to induce the production of oxygen-reactive derivatives, which are molecules having adverse effects on the cell and which are often products of an alteration of cellular metabolism. Expression analysis of CHOP, a marker of activation of the UPR pathway. The formation of oxygen-reactive derivatives can lead to damage of various kinds, such as DNA breaks or the oxidation of cellular proteins. This protein oxidation induces protein misfolding, leading to activation of the unfolded protein response (UPR) pathway. Activation of this UPR pathway can lead to arrest of cell proliferation or cell death. Moreover, this signaling pathway is also induced during metabolic stress, such as during an alteration of extracellular glucose levels. One of the markers of activation of this UPR pathway is the CHOP transcription factor. In order to know the repercussions and / or the origin of the ODC-induced oxygen reactive derivative production, the expression of CHOP was analyzed by Western blotting after treatment of the HCT116 cells with the compounds of the invention. Figure 7B shows that ODC2 and ODC3 (doses between 2.5 and 101.1M) both induce CHOP expression. ODC3 seems to be slightly more active. However, RDC11 and RDC34 have a greater effect on CHOP expression. Conclusion: The compounds of the invention induce CHOP and therefore presumably the UPR pathway. However, the replacement of ruthenium with osmium does not seem to give an advantage to the compounds of the invention in the activation of this route. Analysis of phosphorylation of S6 protein, a marker of mTOR pathway activity. The formation of oxygen-reactive derivatives being an indicator of an alteration of cellular metabolism, a study of the mTOR pathway was carried out. Indeed, the mTOR pathway is one of the important intracellular signaling pathways that controls the homeostasis of cellular metabolism. One of the recognized markers of this pathway is the phosphorylation of the S6 protein on serines 235 and 236. The mTOR pathway is particularly interesting in anticancer therapy. Its inactivation by compounds such as rapamycin promotes the reduction of tumor growth. Phosphorylation of this protein was followed by Western blotting from HCT116 cell extract treated with ODC or RDC. Figure 7C shows that the compounds ODC2 and ODC3 reduce the phosphorylation of the S6 protein, indicating that these compounds repress the activity of the mTOR pathway. However it is interesting to note that the ODCs are slightly less active than the equivalent RDCs (RDC11 and RDC34). Conclusion: The compounds of the invention repress the mTOR pathway. Replacing the ruthenium atom with an osmium atom reduces the activity of the osmium compounds on the mTOR pathway.

Claims (16)

REVENDICATIONS1. Pharmaceutical composition comprising, in a support CLAIMS. A pharmaceutical composition comprising, in a pharmaceutically acceptable carrier, at least one osmium complex compound of the following general formula: wherein: between C and N, represented by a curved line, there is a succession of atoms forming, with C, N and B represented in the formula, a ring (said metallocycle) which consists of 5 to 8 atoms, L3 and L4, identical or different, represent an aromatic ligand or a donor ligand of 2 electrons by an atom of Nitrogen, oxygen, phosphorus or sulfur, or a halogen atom L5 and L6, present or absent simultaneously, identical or different, represent, when present, a donor ligand of 2 electrons per atom. nitrogen, oxygen, phosphorus or sulfur, or a halogen atom, m is 0 or 1 and Y is a counter-ion, when m = 1, each of L3, L4, L5 and L6 being covalently linked to at least one other ligand from L3, L4, L5 and L6, and / or to be covalently linked to at least one metallocycle atom different from the osmium atom, when L5 and L6 are absent simultaneously, one of L3 and L4 is an aromatic ligand. 2. Composition according to the preceding claim, wherein L5 and L6 are absent, L3 is an aromatic ligand and L4 represents a donor ligand of 2 electrons by a nitrogen atom, oxygen, phosphorus or sulfur, or an atom halogen, and in particular the metallocycle is a NACH cycle. 3. The composition according to claim 1, wherein L3 and L4 are covalently connected and together form a bidentate ligand, particularly an electron donor ligand by nitrogen atoms; L5 and L6 are either covalently linked and together form a bidentate ligand, particularly an electron donor ligand by nitrogen atoms, or taken alone represent a monodentate ligand, in particular a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur, or a halogen atom; and in particular the metallocycle is a NACH cycle. 4. A composition according to claim 1, wherein L3, L4 and L5 are covalently connected and together form a tridentate ligand, particularly an electron donor ligand by nitrogen atoms; L6 represents a monodentate ligand, in particular a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom; and in particular the metallocycle is an N'ACH cycle. The composition of claim 1, wherein the metallocycle is covalently bonded to L3, in particular the ring is of NACHAN and NACHAN type; L4 and L5 are either covalently connected and together form a bidentate ligand, particularly an electron donor ligand by nitrogen atoms, or taken alone represent a monodentate ligand, in particular a donor ligand of 2 electrons by an atom of nitrogen, oxygen, phosphorus or sulfur, or a halogen atom; and L6 represents a monodentate ligand, in particular a donor ligand of 2 electrons by a nitrogen, oxygen, phosphorus or sulfur atom, or a halogen atom. The composition of claim 1, wherein the metallocycle is covalently bonded to L3, in particular the ring is of the NACHAN and NANACH type, and L4, L5 and L6 are covalently connected together to form a tridentate ligand, particularly an electron donor ligand by nitrogen atoms. 7. Composition according to one of the preceding claims, characterized in that m is equal to 1. 8. Composition according to one of the preceding claims, characterized in that Y "is BF4, B (C6H5) 4", PF6, CF3SO3-, tosylate (p-toly1SO3 "), mesylate (MeSO3), SO42-, 25 CF3CO2. , CH3CO2, bicarbonate HCO3), (C104, or NO3-. 9. The composition as claimed in claim 1, wherein the compound of formula (I) is chosen from: 10. Composition according to one of the preceding claims 1-8, characterized in that the compound of formula (I) is chosen from: ODC 30 ODC 31 ODC 33 ODC 34 ODC 35 11. Composition according to one of the preceding claims 1-8, characterized in that the compound of formula (I) is selected from: 00C 7 ODC 8 ODC 9 PF? 00C the 0001! ODC 12 00G 1 $ ODC 20,000 21 ODC 22 ODC 23 OCC 24 12. Osmium compound selected from: PF6 P ODC 4 ODC 5 ODC 6 P ODC 7 ODC 8 ODC 9 ODC 10 ODC 11 ODC 12 ODC 13 pF6 ODC 16 ODC 17 ODC 18 ODC 19 pF6 ODC 20 ODC 21 PFP ODC 22 ODC 23 PF6 ODC 24 ODC 28 ODC 30 ODC 31ODC 28 ODC 2 $ PF6c) Pe ODC 32 ODC 33 ODC 34 ODC 35 Pe PF 6 ODC 36 ODC 37 ODC 39 13. Composition or compound according to one of the preceding claims, for use in the treatment of diseases related to cell hyperproliferation. 14. Composition or compound according to one of the preceding claims, for use in the treatment of cancers. 15. The composition or compound according to one of the preceding claims, for use in the treatment of glioblastomas, neuroblastomas, promyelocytic leukemias, prostate cancers, kidneys, ovaries, lungs, breasts, head and neck, digestive tract, especially liver, pancreas, colon, non-Hodgkin's lymphoma or melanoma. 16. Composition or compound according to one of the preceding claims, for use in the treatment of tumors resistant to cisplatin or other anticancer drugs.