WO2015124824A1 - Uso de complejos metálicos miméticos de sod como agentes alimentarios y como cosméticos - Google Patents
Uso de complejos metálicos miméticos de sod como agentes alimentarios y como cosméticos Download PDFInfo
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- WO2015124824A1 WO2015124824A1 PCT/ES2015/070125 ES2015070125W WO2015124824A1 WO 2015124824 A1 WO2015124824 A1 WO 2015124824A1 ES 2015070125 W ES2015070125 W ES 2015070125W WO 2015124824 A1 WO2015124824 A1 WO 2015124824A1
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- WIPO (PCT)
- Prior art keywords
- sod
- mimetic
- food
- formula
- superoxide dismutase
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3544—Organic compounds containing hetero rings
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/358—Inorganic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/16—Inorganic salts, minerals or trace elements
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/16—Inorganic salts, minerals or trace elements
- A23L33/165—Complexes or chelates
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/58—Metal complex; Coordination compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
Definitions
- the present invention relates to the use of the mimetic metal complexes of the enzyme superoxide dismutase (SOD) described in patent ES2355784, and obtained from polyazapyridinophane macrocyclic compounds, as food agents, as well as their use as cosmetics.
- SOD superoxide dismutase
- Antioxidants play an important role in skin protection and repair mechanisms. They can be consumed as food or in the form of food supplements, or they can be applied to the skin as topical formulations.
- the enzyme superoxide dismutase - SOD - belongs to the group of substances with more relevance among natural antioxidants.
- SOD performs important functions in the body such as, for example, protection against cellular oxidative stress and against inflammatory or degenerative processes.
- SOD protects the cell from harmful reactions of radical 0 2 " .
- SOD SOD
- Some plants naturally produce SOD such as broccoli, wheat, barley, but when SOD is ingested by the human body, it is quickly destroyed by stomach acids and intestinal enzymes, so it barely reaches the bloodstream.
- the human organism has the maximum peak of SOD production at the age of approximately 10 years. It is possible to raise blood levels of SOD by consuming supplements in appropriate amounts of suitable precursor molecules. And it is known for example that wheat sprouts are a rich source of these precursors. However, the same problem of the destruction of SOD by the digestive process remains.
- the synthesis of mimetic compounds of the SOD enzyme is necessary to be able to replace the possible deficiencies in the activity of the endogenous SOD, or the lack thereof and, thus, to be able to treat not only the numerous pathologies or diseases that present as a common etiology the lack or deficient activity of said enzyme, but take advantage of its ability to be used as food or cosmetic agents.
- the synthesized mimetic compounds should have a reduced toxicity and, in addition, be able to carry out the dismutation reaction from the lowest possible compound concentration.
- the use of lower concentrations or doses of SOD mimetics would reduce the cost of treatments, as well as the risk associated with the development of side effects and the triggering of immunogenicity.
- SOD mimetic used as a cosmetic is lipochroman-6 (EP21 13242), or that described in patent application US20130287696, which discloses a method to prevent food spoilage and oxidation, by the application thereto of an effective amount of a pegylated SOD mimetic compound, optionally in combination with a second preservative additive.
- a concrete example of SOD mimetic according to this patent is the one shown below:
- the metal complexes described in the main patent have reduced toxicity, low IC 50 values and do not cause the development of immunogenicity.
- the low value of the IC 50 index of these metal complexes has important implications because the lower said value, the smaller the amount of compound necessary to cause the desired mimetic effect. Therefore, the use of a smaller amount of complex to achieve the dismutation reaction will significantly reduce the side effects.
- the mentioned metal complexes have a high half-life due to their stability in plasma and do not present distribution problems in the tissues after administration. Description of the invention
- the present invention relates to the use as cosmetics, or as food agents, of the mimetic metal complexes of SOD, obtained from intermediary compounds that are polyazapyridinophane macrocycles with a quinoline heterocycle attached to the central structure of the molecule, and already described in ES2355784.
- food agent means herein any of the following alternatives: food additive, functional food, dietary supplement or functional drink.
- a metal complex is understood herein as any molecular association of the intermediary compounds of Formula 1, with at least one metal ion, preferably Cu (ll), Fe (ll) or Mn (ll), and more preferably even more Metallic ion is Mn (ll).
- the mimetic complex of the SOD is understood as that metal complex capable of imitating, supplying, and eventually improving, the activity as a cosmetic, personal hygiene product or food agent, and / or functions of the endogenous SOD enzyme .
- the metal complexes described in ES2355784 can be included in formulations for food or cosmetic use, and administered according to the knowledge in the state of the art, in different ways such as: by intradermal injection or orally by capsules, dragees or tablets .
- formulations for cosmetic use or personal hygiene products they can be part of deodorants, antiperspirants, hair and skin care products, and can be, for example, moisturizers, cleansers, or combinations of both.
- Formulations for cosmetic use or personal hygiene products may also be in the form of powders or a solid bar, or in addition to solid forms, they may be, by way of example, in the form of: creams, milks, lotions, emulsions , pastes, liquids, gels, aerosols, solid forms, jellies, ointments, masks, dispersions, suspensions, shampoos, foams, sprays or anhydrous liquids.
- solid forms for cosmetic use can be made in the presence of the necessary excipients selected from the group comprising, but not limited to, mannitol, polyvinyl pyrrolidone, microcrystalline cellulose, silica gel, talcum, magnesium stearate, titanium oxide, dyes. and antioxidants
- the present invention relates more specifically to the use as a cosmetic, or as a food agent, of a mimetic metal complex of the superoxide dismutase of Formula 1
- metal ion is preferably selected from: Cu (ll), Fe (ll) and Mn (ll), and Mn (II) is especially preferred.
- the present invention also relates to the use of the mentioned SOD mimetic metal complexes of Formula I with at least one metal ion, for the preparation of a food agent, which can be a food additive, functional food, a dietary supplement or a beverage functional, or for the elaboration of a product of personal hygiene or a cosmetic formulation.
- a food agent which can be a food additive, functional food, a dietary supplement or a beverage functional, or for the elaboration of a product of personal hygiene or a cosmetic formulation.
- Said metal ion is preferably selected from: Cu (ll), Fe (ll) and Mn (ll), and Mn (II) is especially preferred.
- the present invention also has a cosmetic formulation or a personal hygiene product comprising at least one mimetic metal complex of SOD of Formula I with at least one metal ion, as defined above.
- Said cosmetic formulation or personal hygiene product may be formulated as a cream, a paste, a milk, a gel, a lotion, an ointment, a suspension, a dispersion, a powder, a shampoo, a foam, a spray or a solid bar
- the present invention is directed to a food additive, dietary supplement, a functional food or a functional beverage comprising at least one mimetic metal complex of SOD of Formula I with at least one metal ion, as defined above.
- the metal complexes of the invention overcome the problems cited in the state of the art by having a decreased toxicity and low IC 50 values.
- the low value of the IC 50 index of the metal complexes of the present invention has important implications because the lower said value, the smaller the amount of complex necessary to cause the desired mimetic effect. Therefore, the use of a smaller amount of complex to achieve the dismutation reaction considerably reduces the side effects.
- the metal complexes of the invention have high stability as shown in the main patent ES2355784, and half-life, avoiding problems of distribution in the tissues after administration, as well as the development of immunogenicity.
- a preferred embodiment of the invention relates to the use of mimetic compounds in which the metal ions that bind to the compound of Formula 1 are selected from: Cu (ll), Fe (ll) and Mn (ll). Description of the figures
- Fig. 1 Graphical representation of the results obtained after incubation of Medaka embryos in stage 8 with the oxidant H 2 0 2 and the Pytren-4Q + Mn compound for 72 hours, as detailed in the example.
- Fig. 2 Graphical representation of the results obtained after incubation of Medaka embryos in stage 8 with the oxidant H 2 0 2 and the Pytren-4Q + Mn compound for 14 days, as detailed in the example.
- Fertilized eggs were collected daily, deposited in Yamamoto solution (0.13 M NaCI, 2.7 mM KCI, 1.8 mM CaCI2 and 0.24 mM NaHC0 3 , pH 7.3) (Yamamoto T Medaka (killfish): Biology and strains. 1975, Tokyo: Keigaku Pub. Co), and kept in the incubator at 26 ° C. The stage of the embryos was determined according to the description of Iwamatsu (Iwamatsu T. Stages of normal development in the medaka Oryzyas latipes. Mech Dev. 2004, Vol. 121, pages 605-618).
- Medaka embryos that were in stage 8 were separated into 2 groups of 60 embryos and a group of 30 embryos.
- a group of 60 embryos was treated for 4 days with Pytren-4Q + Mn dissolved in Yamamoto solution at a concentration of 250 ⁇ .
- the other group of 60 embryos was incubated for 4 days in Yamamoto solution. This group was used as a negative control.
- the group of 30 embryos, positive control group was treated for 4 days with a Yamamoto solution of vitamin C, antioxidant compound, at a concentration of 100 ⁇ . After 4 days of embryo incubation They were washed with Yamamoto solution.
- the groups of 60 embryos were separated into two groups of 30 embryos each.
- the embryos of all the groups were placed individually in 96-well plate wells containing each well 200 ⁇ of Yamamoto solution with H 2 0 2 , at different concentrations depending on the incubation period that elapsed until mortality was observed.
- the concentration of H 2 0 2 used was 22.5 mM
- the concentration of H 2 0 2 used was 7.5 mM.
- Thirty embryos from each initial group of 60 embryos were treated with the Yamamoto solution of H 2 0 2 at a concentration of 7.5 mM. This entire experiment was replicated 6 times in the study at 72 hours and 3 times in the study at 14 days.
- Tests were carried out with the Pytren-4Q + Mn compound at a non-toxic concentration for embryos of 250 ⁇ , and its antioxidant capacity was measured in two different assays.
- mortality was observed after 72 h of incubation with H 2 0 2 at 22.5 ⁇ (illustrated in Figure 1).
- mortality was observed after 14 days of incubation with H 2 0 2 at 7.5 mM (illustrated in Figure 2). Both trials showed a significant decrease in mortality, in response to oxidative stress caused by H 2 0 2 .
- the data obtained show that the Pytren-4Q + Mn compound has an antioxidant character, at a concentration of 250 ⁇ , similar to that of vitamin C at 100 ⁇ .
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JP2016570189A JP2017507179A (ja) | 2014-02-24 | 2015-02-24 | スーパーオキシドジスムターゼの金属錯体模倣物の食品薬剤および化粧品としての使用 |
EP15752897.7A EP3112367A4 (en) | 2014-02-24 | 2015-02-24 | Use of metal complexes which are mimetics of sod as food agents and as cosmetics |
US15/121,030 US9750677B2 (en) | 2014-02-24 | 2015-02-24 | Use of metal complexes which are mimetics of SOD as food agents and as cosmetics |
CN201580010034.1A CN106132961A (zh) | 2014-02-24 | 2015-02-24 | 是sod模拟物的金属络合物作为食品试剂和作为化妆品的应用 |
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ESP201400148 | 2014-02-24 | ||
ES201400148A ES2543850B1 (es) | 2014-02-24 | 2014-02-24 | Uso de complejos metálicos miméticos de SOD como agentes alimentarios y como cosméticos |
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EP (1) | EP3112367A4 (es) |
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WO2019007996A1 (en) | 2017-07-04 | 2019-01-10 | Bionos Biotech, S.L | USE OF METALLIC COMPLEXES OF MACROAZAPYRIDINOPHANES IN THE TREATMENT OF DISEASES |
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US11904863B2 (en) | 2018-10-26 | 2024-02-20 | AutoBrains Technologies Ltd. | Passing a curve |
US11700356B2 (en) * | 2018-10-26 | 2023-07-11 | AutoBrains Technologies Ltd. | Control transfer of a vehicle |
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US6794371B1 (en) * | 1999-10-18 | 2004-09-21 | The Dow Chemical Company | Aminoalkylenephosphonates for treatment of bone disorders |
US20070298354A1 (en) * | 2006-06-27 | 2007-12-27 | Ni Ding | Carbon coating on an implantable device |
ES2414291A1 (es) * | 2011-12-16 | 2013-07-18 | Universitat De Valencia | Compuestos macrocíclicos de tipo escorpiando y su uso como antiparasitarios. |
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US20120301403A1 (en) * | 2007-06-21 | 2012-11-29 | Galera Therapeutics, Llc | Polyethylene glycolated superoxide dismutase mimetics |
EP2113242A1 (en) | 2008-05-02 | 2009-11-04 | Pangaea Laboratories Limited | Antioxidant for use in cosmetic, medicated and pharmaceutical preparations |
ES2355784B1 (es) | 2009-09-21 | 2012-02-03 | Universitat De Valencia | Complejos metalicos mimeticos de sod |
PL2433640T3 (pl) * | 2010-09-24 | 2020-06-01 | Omnivision Gmbh | Kompozycja zawierająca SOD, luteinę i zeaksantynę |
-
2014
- 2014-02-24 ES ES201400148A patent/ES2543850B1/es active Active
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2015
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- 2015-02-24 CN CN201580010034.1A patent/CN106132961A/zh active Pending
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US6794371B1 (en) * | 1999-10-18 | 2004-09-21 | The Dow Chemical Company | Aminoalkylenephosphonates for treatment of bone disorders |
US20070298354A1 (en) * | 2006-06-27 | 2007-12-27 | Ni Ding | Carbon coating on an implantable device |
ES2414291A1 (es) * | 2011-12-16 | 2013-07-18 | Universitat De Valencia | Compuestos macrocíclicos de tipo escorpiando y su uso como antiparasitarios. |
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CLARES MA PAZ ET AL.: "Manganese(II) complexes of scorpiand-like azamacrocycles as MnSOD mimics..", CHEMICAL COMMUNICATIONS, vol. 47, no. 21, 7 June 2011 (2011-06-07), pages 5988 - 5990, XP055220982, ISSN: 1364-548X * |
OLMO FRANCISCO ET AL.: "Scorpiand-like azamacrocycles prevent the chronic establishment ofTrypanosoma cruziin a murine model.", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY EDITIONS SCIENTIFIQUE ELSEVIER, vol. 70, PARIS, FR, pages 189 - 198, XP028794141, ISSN: 0223-5234 * |
See also references of EP3112367A4 * |
Cited By (2)
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WO2019007996A1 (en) | 2017-07-04 | 2019-01-10 | Bionos Biotech, S.L | USE OF METALLIC COMPLEXES OF MACROAZAPYRIDINOPHANES IN THE TREATMENT OF DISEASES |
US11013732B2 (en) | 2017-07-04 | 2021-05-25 | Bionos Biotech, S.L. | Use of macroazapyridinophanes metal complexes in the treatment of diseases |
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EP3112367A1 (en) | 2017-01-04 |
CN106132961A (zh) | 2016-11-16 |
US9750677B2 (en) | 2017-09-05 |
ES2543850B1 (es) | 2016-06-16 |
JP2017507179A (ja) | 2017-03-16 |
ES2543850R2 (es) | 2015-09-07 |
EP3112367A4 (en) | 2017-05-03 |
ES2543850A2 (es) | 2015-08-24 |
US20170007521A1 (en) | 2017-01-12 |
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