ES2689484T3 - Compuestos terapéuticos - Google Patents
Compuestos terapéuticos Download PDFInfo
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- ES2689484T3 ES2689484T3 ES14173039.0T ES14173039T ES2689484T3 ES 2689484 T3 ES2689484 T3 ES 2689484T3 ES 14173039 T ES14173039 T ES 14173039T ES 2689484 T3 ES2689484 T3 ES 2689484T3
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms
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- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Un compuesto de Fórmula 2:**Fórmula** para uso en el tratamiento de la glomeruloesclerosis segmentaria focal; en donde R1 y R2, 20 que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en un C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino y una cadena que contiene un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; X1 y X2 son iguales o diferentes y se seleccionan del grupo que consiste en un enlace, O, N y S; T es un enlace simple o doble; R3 se selecciona del grupo que consiste en H, C3 a C10 alqueno, C3 a C10 alquino y una cadena que contiene un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; R4 se selecciona del grupo que consiste en H, OH, OR6, NHR6 y NR6R7; R5 se selecciona del grupo que consiste en H, NHR6, NR6R7, OR, halógeno, C3 a C10 alqueno, C3 a C10 alquino y una cadena que consiste en un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; R6 y R7, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en H, C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino, arilo, C5 a C20 alcarilo, y una cadena hidrocarbonada que contiene un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; R8 se selecciona del grupo que consiste en H, C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino, arilo, C5 a C20 alcarilo y una cadena hidrocarbonada que contiene un heterociclo o anillo fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; y n es un número entero entre 0 y 4; o sales farmacéuticamente aceptables de los mismos; con la condición de que cuando X1 y X2 son ambos O o un enlace, y uno de R1 o R2 es un alquilo de C1 a C4, el otro de R1 o R2 es un alquilo de C4 a C10, cicloalquilo de C3 a C10, cicloalquilmetilo de C3 a C10, C3 a C10 alquino, o una cadena que contiene un anillo heterocíclico o fusionado; y con la condición de que el compuesto no sea Tranilast.
Description
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DESCRIPCION
Compuestos terapéuticos Campo de la invención
[0001] La presente invención se refiere a compuestos para el tratamiento de trastornos médicos. La presente invención se refiere además al uso de los compuestos para el tratamiento de trastornos médicos, en particular estados asociados con la fibrosis tisular.
Antecedentes de la invención
[0002] El tranilast (ácido n-[3,4-dimetoxicinnamoílo]antranílico) es un agente antifibrótico utilizado en Japón para el tratamiento de trastornos fibróticos de la piel tales como queloides [8] y esclerodermia [9]. Aunque los mecanismos precisos y modo de acción se conocen por completo, su capacidad para inhibir fosforilación de ERK [20], un importante intermedio en la vía de señalización de TGF-p, puede ser la base de sus efectos antifibróticos, con acciones conocidas de tranilast incluyendo la inhibición de la producción de matriz extracelular inducida por TGF-p en un rango de tipos de células [10, 11, 14, 16]. También se ha demostrado que Tranilast atenúa la síntesis de colágeno inducida por TGF-p en fibroblastos cardíacos utilizando un modelo experimental de enfermedad diabética por cáncer [15].
[0003] La fibrosis es una respuesta común a una gama de insultos de tejidos que pueden conducir a la disfunción orgánica. Las enfermedades que se caracterizan por dicha fibrosis patológica incluyen cirrosis hepática, fibrosis intersticial pulmonar, glomerulonefritis, insuficiencia cardíaca (isquémica y no isquémica), nefropatía diabética, esclerodermia, exceso de tejido cicatricial después de la cirugía o inserción del dispositivo, enfermedad renal progresiva, glomerulonefritis, hipertensión, insuficiencia cardíaca debido a cardiopatía isquémica, enfermedad cardíaca valvular o enfermedad cardíaca hipertensiva y cicatrices hipertróficas. Además, la elaboración de la matriz patológica también tiene un papel en la progresión fibroproliferativa del tumor y la metástasis.
[0004] Los sujetos diabéticos tienen un riesgo de dos o cinco veces mayor de desarrollar insuficiencia cardíaca [1]. Además de la cardiopatía isquémica, la insuficiencia cardíaca en la diabetes también se asocia con una miocardiopatía, independiente de la enfermedad arterial coronaria [2]. Esta denominada "miocardiopatía diabética" se caracteriza histológicamente por fibrosis miocárdica con elasticidad miocárdica reducida, contractilidad alterada y disfunción cardíaca manifiesta [3-6]. En consecuencia, las estrategias que reducen la acumulación patológica de la matriz extracelular se han defendido como posibles terapias para el tratamiento y prevención de la insuficiencia cardíaca en estados diabéticos y no diabéticos [7].
[0005] El tratamiento actual de la insuficiencia cardíaca crónica se centra en la modulación de la activación neurohormonal que típicamente se desarrolla en respuesta a las anomalías funcionales en evolución. Sin embargo, a pesar de dicha terapia, frecuentemente utilizada en combinación, la disfunción cardíaca continúa progresando en la mayoría de los pacientes. Dada la importancia de la fibrosis patológica en la remodelación cardíaca adversa, se ha sugerido un posible papel de los agentes antifibróticos [16]. Los estudios realizados durante más de una década han indicado consistentemente un papel importante para el factor de crecimiento prosclelerótico, transformando el factor de crecimiento p (TGF-p) en la fibrosis y disfunción del órgano [17], de modo que el bloqueo de su expresión y acción representa una diana importante terapéutica.
[0006] También se ha demostrado que Tranilast reduce la inflamación en enfermedades alérgicas, como la rinitis alérgica y el asma bronquial, etc. [42].
[0007] Además, se ha demostrado que tranilast tiene actividad antiproliferativa [43, 44].
[0008] Sin embargo, recientemente se ha demostrado [19] que los factores genéticos en ciertos pacientes, específicamente una variante UGT1A1 de síndrome de Gilbert, confiere susceptibilidad a hiperbilirrubinemia inducida por tranilast. Dicha hiperbilirrubinemia puede asociarse con el tranilast mismo o la formación, in vivo, del siguiente metabolito tranilast
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[0009] Sería útil proporcionar compuestos adicionales con potencial actividad antifibrótica, antiinflamatoria y antiproliferativa o antineoplásica para el tratamiento o la prevención de enfermedades asociadas con enfermedades de la fibrosis caracterizadas por inflamación y enfermedad neoplásica (tanto benignas como malignas), y como alternativas/adjuntos a tranilast.
[0010] El documento JP H10 306024 A describe ciertos derivados de 2-acilaminobenzamida como agentes preventivos y terapéuticos contra enfermedades glomerulares tales como glomerulonefritis y nefritis diabética.
[0011] Es un objeto de la presente invención superar o al menos aliviar una o más de las dificultades y/o deficiencias relacionadas con la técnica anterior.
Sumario de la invención
[0012] La presente invención proporciona un compuesto de la Fórmula 2
Fórmula 2
para uso en el tratamiento de la glomeruloesclerosis segmentaria focal;
en donde R1 y R2, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en un C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino y una cadena que
contiene un anillo heterocíclico o fusionado; cualquiera de los cuales puede estar opcionalmente sustituido;
X1 y X2 son iguales o diferentes y se seleccionan del grupo que consiste en un enlace, O, N y S;
T es un enlace simple o doble;
R3 se selecciona del grupo que consiste en H, C3 a C10 alqueno, C3 a C10 alquino y una cadena que contiene un
anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido;
R4 se selecciona del grupo que consiste en H, OH, OR6, NHR6 o NR6R7;
R5 se selecciona del grupo que consiste en H, NHR6, NR6R7, OR8, halógeno, C3 a C10 alqueno, C3 a C10 alquino y
una cadena que consiste en un anillo heterocíclico o fusionado; cualquiera de los cuales puede estar opcionalmente sustituido;
R6 y R7, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en H, C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino, arilo, C5 a C20 alcarilo, y una cadena hidrocarbonada que contiene un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido;
R8 se selecciona del grupo que consiste en H, C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino, arilo, C5 a C20 alcarilo y una cadena hidrocarbonada que contiene un heterociclo o anillo fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; y
n es un número entero entre 0 y 4;
o sales farmacéuticamente aceptables de los mismos;
con la condición de que cuando X1 y X2 son ambos O o un enlace, y uno de R1 o R2 es un C1 a C4 alquilo, el otro de R1 o R2 es C4 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alquino, o una cadena que contiene un anillo heterocíclico o fusionado; y
con la condición de que el compuesto no sea Tranilast.
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[0013] Sorprendentemente, se ha descubierto que los compuestos de la Fórmula 2 anterior pueden exhibir actividad antifibrótica y, en ciertos casos, actividad antifibrótica mejorada significativa.
[0014] Los compuestos preferidos son aquellos en los que X1 y X2 son O. Los compuestos preferidos son también aquellos en los que X1 y X2 son O y R1 o R2 es metilo. Los compuestos preferidos son también aquellos en los que X1 y X2 son O, R1 o R2 es metilo, y R3 es H. Los compuestos preferidos son también aquellos en los que X1 y X2 son O, R1 o R2 es metilo, R3 es H y R4 es OH o NHR5. Los compuestos preferidos son también aquellos en los que X1 y X2 son O, R1 o R2 es metilo, R3 es H, R4 es OH o NHR5R, y Rs es H o halógeno. Los compuestos preferidos son también aquellos en los que X1 y X2 son O y R1 o R2 es un alquino o una cadena que contiene un triazol. Los compuestos preferidos son también aquellos en los que X1 y X2 son O y R1 o R2 es un C3 a C8 alquino terminal o no terminal, preferiblemente el alquino es propargilo. Los compuestos preferidos son también aquellos en los que X1 y X2 son O y R1 o R2 es una cadena que contiene un 1,4-disustituido-1,2,3-triazol. Los compuestos preferidos son también aquellos en los que X1 y X2 son O y R1 o R2 incluyen un grupo ciclopentilo, ciclohexilo, ciclopentilmetilo o ciclohexilmetilo.
[0015] Más preferiblemente, esos compuestos son aquellos en los que:
X1 y X2 son O;
R1 o R2 es metilo;
R3 es H;
R4 es OH o NHRa;
R5 es preferiblemente H o un halógeno, por ejemplo, Br, I, Cl o F, más preferiblemente Br;
R1 o R2 es un alquino, una cadena que contiene un triazol, un grupo ciclopentilo, un grupo ciclohexilo, un grupo ciclopentilmetilo o un grupo ciclohexilmetilo; y
R6 es H.
[0016] En una forma particularmente preferida, los compuestos se pueden seleccionar de aquellos en los que R1 o R2 es metilo.
[0017] Preferiblemente uno de R1 y R2 es metilo y el otro de R1 y R2 es un C3 a C10 cicloalquilo, C3 a C10 cicloalquilo- metilo, C3 a C10 alquino o una cadena que contiene un triazol. Preferiblemente, el triazol es un 1,2,3-triazol 1,4- disustituido.
[0018] Cuando R1 o R2 es un alquino, preferiblemente el alquino es un terminal C5 a C8 o alquino no terminal, lo más preferiblemente propargilo.
Descripción detallada de la invención
[0019] El término "alquilo" como se usa en este documento incluye radicales alquilo lineales y ramificados, por ejemplo, metilo, etilo, propilo, isopropilo, butilo, isobutilo, sec-butilo, terc-butilo, etc.
[0020] El término "arilo", como se usa en el presente documento, se refiere a anillos aromáticos sustituidos o no sustituidos que están condensados, sin fusionar o unidos y pueden incluir uno o más heteroátomos.
[0021] El término "anillo fusionado" como se usa en el presente documento se refiere a dos o más anillos unidos entre sí a través de uno o más átomos. El término incluye anillos fusionados sustituidos o no sustituidos.
[0022] Los compuestos preferidos de la presente invención para uso en el tratamiento de la glomeruloesclerosis segmentaria focal son de la Fórmula 3
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donde Rg o R10, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en C8 alquino o alquino no terminal, ciclopentilo, ciclohexilo, ciclohexilmetilo y ciclopentilmetilo; o sales farmacéuticamente aceptables de los mismos;
con la condición de que cuando uno de R9 o R10 es un C1 a C4 alquilo, el otro de R9 o R10 es un C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alquino o una cadena que contiene un fusionado, o cualquiera de los cuales está opcionalmente sustituido; y con la condición de que el compuesto no sea Tranilast.
[0023] En una realización preferida, la presente invención proporciona un compuesto de la Fórmula 3 para uso en el tratamiento de glomeruloesclerosis segmentaria focal, en donde uno de R9 o R10 incluye un C3 a C8 alquino y el otro de R9 o R10 es metilo. El alquino puede ser un alquino terminal o no terminal.
[0024] En una realización adicional, el compuesto para uso en el tratamiento de glomeruloesclerosis segmentaria focal tiene la Fórmula 4 o Fórmula 5
C1 a C10 alquilo, C3 a
C4 a C10 alquilo, C3 a anillo heterocíclico o
en donde p es un número entero entre 1 y 10, preferiblemente entre 1 y 6; y R se selecciona del grupo que consiste en H y C1 a C10 alquilo;
o sales farmacéuticamente aceptables de los mismos.
[0025] En una realización adicional, el compuesto para uso en el tratamiento de glomeruloesclerosis segmentaria focal tiene la Fórmula 6 o Fórmula 7
donde G es un anillo de ciclopentilo, un anillo de ciclohexilo o un 1,2,3-triazol 1,4-disustituido; y q es un número entero entre 0 y 6 o sales farmacéuticamente aceptables de los mismos.
[0026] Los compuestos para uso en el tratamiento de la glomeruloesclerosis segmentaria focal de la presente invención se pueden seleccionar de uno o más del grupo que consiste en
Claims (13)
- 51015202530354045505560651. Un compuesto de Fórmula 2:
imagen1 para uso en el tratamiento de la glomeruloesclerosis segmentaria focal;en donde R1 y R2, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en un C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino y una cadena quecontiene un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido;X1 y X2 son iguales o diferentes y se seleccionan del grupo que consiste en un enlace, O, N y S;T es un enlace simple o doble;R3 se selecciona del grupo que consiste en H, C3 a C10 alqueno, C3 a C10 alquino y una cadena que contiene unanillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido;R4 se selecciona del grupo que consiste en H, OH, OR6, NHR6 y NR6R7;R5 se selecciona del grupo que consiste en H, NHR6, NR6R7, OR, halógeno, C3 a C10 alqueno, C3 a C10 alquino yuna cadena que consiste en un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido;R6 y R7, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en H, C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino, arilo, C5 a C20 alcarilo, y una cadena hidrocarbonada que contiene un anillo heterocíclico o fusionado, cualquiera de los cuales puede estar opcionalmente sustituido;R8 se selecciona del grupo que consiste en H, C1 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alqueno, C3 a C10 alquino, arilo, C5 a C20 alcarilo y una cadena hidrocarbonada que contiene un heterociclo o anillo fusionado, cualquiera de los cuales puede estar opcionalmente sustituido; y n es un número entero entre 0 y 4; o sales farmacéuticamente aceptables de los mismos;con la condición de que cuando X1 y X2 son ambos O o un enlace, y uno de R1 o R2 es un alquilo de C1 a C4, el otro de R1 o R2 es un alquilo de C4 a C10, cicloalquilo de C3 a C10, cicloalquilmetilo de C3 a C10, C3 a C10 alquino, o una cadena que contiene un anillo heterocíclico o fusionado; y con la condición de que el compuesto no sea Tranilast. - 2. Un compuesto para su uso según la reivindicación 1 que tiene la Fórmula 3:
imagen2 en donde Rg o R10, que pueden ser iguales o diferentes, se seleccionan del grupo que consiste en C1 a C10 alquilo, C3 a C8 alquino o alquino no terminal, ciclopentilo, ciclohexilo, ciclohexilmetilo y ciclopentilmetilo; o sales farmacéuticamente aceptables de los mismos;con la condición de que cuando uno de Rg o R10 es un alquilo de C1 a C4, el otro de Rg o R10 es un C4 a C10 alquilo, C3 a C10 cicloalquilo, C3 a C10 cicloalquilmetilo, C3 a C10 alquino o una cadena que contiene un heterociclo5101520253035404550556065o anillo fusionado, cualquiera de los cuales está opcionalmente sustituido; y con la condición de que el compuesto no sea Tranilast. - 3. El compuesto para su uso de acuerdo con la reivindicación 1, en el que X1 y X2 son O.
- 4. El compuesto para su uso de acuerdo con la reivindicación 3, en el que R1 o R2 es metilo.
- 5. El compuesto para su uso de acuerdo con la reivindicación 4, en el que R3 es H.
- 6. El compuesto para su uso de acuerdo con la reivindicación 3, en el que R1 o R2 es un alquino o una cadena quecontiene un triazol.
- 7. Un compuesto para su uso según la reivindicación 1 que tiene la Fórmula 4 o Fórmula 5:
imagen3 oimagen4 donde p es un número entero entre 1 y 10; y R se selecciona del grupo que consiste en H y C1 a C10 alquilo; o sales farmacéuticamente aceptables de los mismos. - 8. Un compuesto para su uso según la reivindicación 1 que tiene la Fórmula 6 o Fórmula 7
imagen5 oimagen6 5101520253035404550556065en donde G es un anillo de ciclopentilo, un anillo de ciclohexilo o un anillo de 1,2,3-triazol 1,4-disustituido; y q es un número entero entre 0 y 6; o sales farmacéuticamente aceptables de los mismos. - 9. Un compuesto para su uso según la reivindicación 1, seleccionado del grupo que consiste en
imagen7 5101520253035404550556065imagen8 imagen9 imagen10 5101520253035404550556065imagen11 imagen12 imagen13 imagen14 imagen15 y5101520253035404550556065o sales farmacéuticamente aceptables de los mismos. - 10. Un compuesto para su uso según la reivindicación 1, seleccionado del grupo que consiste enO
imagen16 imagen17 imagen18 imagen19 imagen20 yimagen21 o sales farmacéuticamente aceptables de los mismos. - 11. Un compuesto para su uso de acuerdo con la reivindicación 1, en el que el compuesto tiene la fórmula:
imagen22 o una sal farmacéuticamente aceptable de los mismos.cpro25000-i20000 -imagen23 O TGF 10, 30 100 1 10 50TG'F + TL{uM) TCF + #11 (uM)#P<0;001 vs O; * P<0.001 vsTGFFIGURA 1imagen24 FIGURA 2imagen25 FIGURA 3imagen26 TGF0 + Compuesto 11 (|¿M)*P«M>1 v* Control; #|*0.00t vo TGF¡ Q.O05 va TGF; ##p*0,0509 va TGF; —pao.011 V»TGFFIGURA 4imagen27 FIGURA 5cooFIGURA 6imagen28 FIGURA 7imagen29 coK)FIGURA 8imagen30 cocoFIGURA 9imagen31 co4^FIGURA 10MtiC ftrfCE /^OlllfifédVL UftÚJ&Limagen32 coenVWtCOl Artoc W»H)t wrtooi W^OC WriOl eca.’djoi 6c*.tioi ourtioi u«tf ííu uiwíjdí kurtJOi% Inhibición©SéSglSéimagen33 imagen34 imagen35 imagen36 imagen37 imagen38 coO)FIGURA 12imagen39 co-viFIGURA 13imagen40 co00FIGURA 14imagen41 coCDFIGURA 15imagen42 100FIGURA 16imagen43 oimagen44 102FIGURA 18OOOOOOOOOOOimagen45 103FIGURA 19WriO£ IfírtCH >¥i£ wrtoc l(\»ict yuncSEfttól 5£*/¿¿OI 3£#rt!J01 Uí/EiOl HffllJOl Ufc’EdOlMOs„ jL ,imagen46 imagen47 imagen48 80-*104FIGURA 20imagen49 mfVtimagen50 FIGURA 21mM/24 horasConcentración de FT011 en orina - 0.12
- 0.1 -
imagen51 SO mg/kg/día 100 mg/kg/día 200 mg/kg/día 400 mg/kg/díaFIGURA 22imagen52 FIGURA 23% / Secciónimagen53 FIGURA 24imagen54 FIGURA 25imagen55 imagen56 FIGURA 26niLZ VidflOIdimagen57 Número/campoimagen58 FIGURA 28imagen59 FIGURA 29114imagen60 mg/díaimagen61 FIGURA 31%/áreaGlomcruloesclcrosisimagen62 Control Control+FTOll Diabético Diabético + FT011Túbulointorsticial colagenoso Iimagen63 Control Control* FTO11 Diabético Diabético ♦ FT011FIGURA 32imagen64 FIGURA 33imagen65 FIGURA 34118
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WO2010071865A1 (en) | 2008-12-19 | 2010-06-24 | Nuon Therapeutics, Inc. | Pharmaceutical compositions and methods for treating hyperuricemia and related disorders |
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