[go: up one dir, main page]

ES2564179T3 - Derivados de 4-(p-quinonil)-2-hidroxibutanamida para tratamiento de enfermedades mitocondriales - Google Patents

Derivados de 4-(p-quinonil)-2-hidroxibutanamida para tratamiento de enfermedades mitocondriales

Info

Publication number
ES2564179T3
ES2564179T3 ES08847883.9T ES08847883T ES2564179T3 ES 2564179 T3 ES2564179 T3 ES 2564179T3 ES 08847883 T ES08847883 T ES 08847883T ES 2564179 T3 ES2564179 T3 ES 2564179T3
Authority
ES
Spain
Prior art keywords
alkyl
aryl
group
hydrogen
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
ES08847883.9T
Other languages
English (en)
Inventor
Orion D. Jankowski
Kieron E. Wesson
Paul Mollard
William D. Shrader
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Edison Phamaceuticals Inc
Original Assignee
Edison Phamaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Edison Phamaceuticals Inc filed Critical Edison Phamaceuticals Inc
Application granted granted Critical
Publication of ES2564179T3 publication Critical patent/ES2564179T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/80—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • 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
    • 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
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/51—Acetal radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/10—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
    • C07D295/112—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C07D295/116—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
    • C07D295/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/66—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Neurology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrane Compounds (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto que es de la fórmula I:**Fórmula** en la que R se selecciona entre el grupo que consiste en:**Fórmula** en la que * indica el punto de unión de R al resto de la molécula; R1, R2 y R3 se seleccionan independientemente entre el grupo que consiste en hidrógeno y alquilo-C1-C6; R4 es alquilo-C1-C6; R5 y R6 se seleccionan independientemente entre el grupo que consiste en hidrógeno, hidroxi, alcoxi, alquilo-C1-C40, alquenilo-C1-C40, alquinilo-C1-C4 y arilo; donde los grupos alquilo, alquenilo, alquinilo o arilo están opcionalmente sustituidos con -OR10, -S(O)0-2R10, -CN, -F, -Cl, -Br, -I, -NR10R10', oxo, cicloalquilo-C3-C6, arilo, aril-alquilo-C1-C6, heteroarilo, heterociclilo, -C(O)-R11, -C(O)-alquil-C0-C6-arilo, -C(O)-O-R11, -C(O)-O-alquil-C0-C6-arilo, -C(O)-N-R11R11', -C(O)- NH-alquil-C0-C6-arilo, -NH-C(O)-R11 o -NH-C(O)-alquil-C0-C6-arilo; donde los sustituyentes de los anillos de arilo, heteroarilo y heterociclilo están opcionalmente sustituidos adicionalmente con alquilo-C1-C6, haloalquilo-C1-C6, oxo, hidroxi, alcoxi-C1-C6, -C(O)-alquilo-C1-C6 y -C(O)-O-alquilo-C1-C6; y donde uno de los carbonos de los grupos alquilo, alquenilo o alquinilo está opcionalmente sustituido con un heteroátomo seleccionado del grupo que consiste en -O-, -N- y -S-; o R5 y R6 junto con el átomo al cual están unidos forman un anillo de 3-8 miembros saturado o insaturado, que incorpora opcionalmente 1, 2 o 3 átomos adicionales de N, O o S, opcionalmente sustituidos con oxo, -OR10, - SR10, -CN, -F, -Cl, -Br, -I, -NR10R10', alquilo-C1-C6, haloalquilo-C1-C6; hidroxi-alquilo-C1-C6, -C(O)-H, -C(O)- alquilo-C1-C6, -C(O)-arilo, -C(O)-OH o -C(O)-O-alquilo-C1-C6; o R5 y R6 junto con el átomo de nitrógeno al cual están unidos forman una N,N'-piperazina disustituida donde la sustitución de nitrógeno en la posición 4 es un grupo idéntico a la sustitución en la posición 1 formando un compuesto de la fórmula Iaa o Ibb, donde R1, R2, R3 y R4 son como se han definido anteriormente:**Fórmula** R10 y R10' se seleccionan independientemente entre el grupo que consiste en hidrógeno, alquilo-C1-C6, haloalquilo-C1-C6, arilo, aril-alquilo-C1-C6, heteroarilo, heterociclilo, -C(O)-H, -C(O)-alquilo-C1-C6, -C(O)-arilo y - C(O)-alquil-C1-C6-arilo; R11 y R11' se seleccionan entre el grupo que consiste en hidrógeno y alquilo-C1-C6; y M y M' se seleccionan independientemente entre el grupo que consiste en hidrógeno, -C(O)-R12-C(O)- alquenilo-C1-C6, -C(O)-alquinilo-C1-C6, -C(O)-arilo, -C(O)-heteroarilo, -C(O)O-R12, -C(O)NR12R12, -SO2OR12, -SO2-alquilo-C1-C6, -SO2-halo-alquilo-C1-C6, -SO2-arilo, -SO2-NR12R12, -P(O)(OR12)(OR12) y mono o di-péptido ligado a C, donde R12 es hidrógeno o alquilo-C1-C6 sustituido opcionalmente con -OH, -NH2, -NH(alquilo-C1-C4), - N(alquilo-C1-C4)2, -C(O)-OH, -C(O)-O-alquilo-C1-C4 o halógeno; o una sal, un estereoisómero o una mezcla de estereoisómeros de los mismos.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
imagen9
imagen10
imagen11
imagen12
imagen13
imagen14
imagen15
imagen16
imagen17
imagen18
imagen19
imagen20
imagen21
imagen22
imagen23
imagen24
imagen25
imagen26
imagen27
imagen28
imagen29
imagen30
imagen31
imagen32
imagen33
imagen34
imagen35
imagen36
imagen37
imagen38
imagen39
imagen40
imagen41
imagen42
imagen43

Claims (1)

  1. imagen1
    imagen2
    imagen3
    imagen4
    imagen5
    imagen6
ES08847883.9T 2007-11-06 2008-11-04 Derivados de 4-(p-quinonil)-2-hidroxibutanamida para tratamiento de enfermedades mitocondriales Active ES2564179T3 (es)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US212607P 2007-11-06 2007-11-06
US212707P 2007-11-06 2007-11-06
US2127 2007-11-06
US2126 2007-11-06
PCT/US2008/082374 WO2009061744A2 (en) 2007-11-06 2008-11-04 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases

Publications (1)

Publication Number Publication Date
ES2564179T3 true ES2564179T3 (es) 2016-03-18

Family

ID=40474999

Family Applications (1)

Application Number Title Priority Date Filing Date
ES08847883.9T Active ES2564179T3 (es) 2007-11-06 2008-11-04 Derivados de 4-(p-quinonil)-2-hidroxibutanamida para tratamiento de enfermedades mitocondriales

Country Status (12)

Country Link
US (7) US7968746B2 (es)
EP (4) EP3018122B1 (es)
JP (8) JP5755881B2 (es)
CA (1) CA2704473C (es)
DK (2) DK2220030T3 (es)
EA (2) EA028911B1 (es)
ES (1) ES2564179T3 (es)
HU (1) HUE028502T2 (es)
MX (3) MX2010004622A (es)
PL (2) PL3456707T3 (es)
SI (2) SI2220030T1 (es)
WO (1) WO2009061744A2 (es)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005032544A1 (en) 2003-09-19 2005-04-14 Galileo Pharmaceuticals, Inc. Treatment of mitochondrial diseases
EP2564842A1 (en) 2005-06-01 2013-03-06 Edison Pharmaceuticals, Inc. Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
CA2635280C (en) 2006-02-22 2017-12-12 Edison Pharmaceuticals, Inc. Side chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
HUE028502T2 (en) 2007-11-06 2016-12-28 Edison Pharmaceuticals Inc 4- (P-Quinonyl) -2-hydroxybutanamide derivatives for the treatment of mitochondrial diseases
WO2009089224A1 (en) * 2008-01-08 2009-07-16 Edison Pharmaceuticals, Inc. (HET) ARYL-p-QUINONE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES
JP2011513420A (ja) * 2008-03-05 2011-04-28 エジソン ファーマシューティカルズ， インコーポレイテッド レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置
WO2009111576A2 (en) 2008-03-05 2009-09-11 Edison Pharmaceuticals, Inc. 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES
JP5798481B2 (ja) 2008-06-25 2015-10-21 エジソン ファーマシューティカルズ， インコーポレイテッド 酸化ストレス疾患を治療するための２−ヘテロシクリルアミノアルキル−（ｐ−キノン）誘導体
LT3827815T (lt) 2008-09-10 2023-10-10 Ptc Therapeutics, Inc. Psichologinių raidos sutrikimų gydymas oksidacijos redukcijos atžvilgiu aktyviais vaistais
CA2740773A1 (en) 2008-10-14 2010-04-22 Edison Pharmaceuticals, Inc. Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells
EA201692046A1 (ru) 2008-10-28 2017-06-30 Эдисон Фармасьютикалз, Инк. СПОСОБ ПОЛУЧЕНИЯ α-ТОКОТРИЕНОЛА И ЕГО ПРОИЗВОДНЫХ
CA2777479C (en) 2009-04-28 2017-10-17 Edison Pharmaceuticals, Inc. Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones
AU2010286704B2 (en) * 2009-08-26 2016-10-20 Ptc Therapeutics, Inc. Methods for the prevention and treatment of cerebral ischemia
US9452189B2 (en) 2010-10-07 2016-09-27 California Institute Of Technology Probiotic therapies for autism
EP2692862B1 (en) 2011-03-31 2019-03-06 Triplex Therapeutics Inc. Polyamide compound and pharmaceutical composition for treating mitochondrial genetic diseases
WO2012173952A1 (en) * 2011-06-13 2012-12-20 Emory University Piperazine derivatives, compositions, and uses related thereto
EP2720689A4 (en) 2011-06-14 2014-11-26 Edison Pharmaceuticals Inc CATECHOL DERIVATIVES FOR THE TREATMENT OF DISEASES ASSOCIATED WITH OXIDATIVE STRESS
WO2013013078A1 (en) 2011-07-19 2013-01-24 Edison Pharmeceuticals, Inc. Methods for selective oxidation of alpha tocotrienol in the presence of non-alpha tocotrienols
RS55813B2 (sr) * 2012-07-12 2019-12-31 Khondrion Ip B V Hromanil derivati za tretiranje mitohondrijalne bolesti
US9388156B2 (en) 2012-07-12 2016-07-12 Khondiron IP B.V. Chromanyl derivatives for treating mitochondrial disease
EP2890808A4 (en) 2012-08-29 2016-09-28 California Inst Of Techn DIAGNOSIS AND TREATMENT OF AUTISTICAL DISEASES
JP2015533794A (ja) * 2012-09-07 2015-11-26 エジソン ファーマシューティカルズ， インコーポレイテッド 酸化ストレス障害を処置するためのベンゾキノン誘導体
JP6405312B2 (ja) * 2012-10-23 2018-10-17 ニコックス サイエンス アイルランド 眼科用のキノン系一酸化窒素供与化合物
NL2010010C2 (en) 2012-12-19 2014-06-23 Sulfateq B V Compounds for protection of cells.
US9868711B2 (en) 2013-03-15 2018-01-16 Bioelectron Technology Corporation Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders
US9670170B2 (en) 2013-03-15 2017-06-06 Bioelectron Technology Corporation Resorufin derivatives for treatment of oxidative stress disorders
US9296712B2 (en) 2013-03-15 2016-03-29 Edison Pharmaceuticals, Inc. Resorufin derivatives for treatment of oxidative stress disorders
CA2906145A1 (en) 2013-03-15 2014-09-18 Edison Pharmaceuticals, Inc. Alkyl-heteroaryl substituted quinone derivatives for treatment of oxidative stress disorders
KR102511878B1 (ko) 2014-10-30 2023-03-20 캘리포니아 인스티튜트 오브 테크놀로지 신경발달 장애에서의 행동을 개선하기 위한 박테리아를 포함하는 조성물 및 방법
BR112017009004A2 (pt) 2014-10-30 2017-12-19 California Inst Of Techn composições e métodos compreendendo bactérias para melhorar o comportamento em distúrbios do desenvolvimento neurológico
US20180002247A1 (en) * 2014-12-16 2018-01-04 Bioelectron Technology Corporation Methods for chiral resolution of trolox
CN107531616B (zh) 2014-12-16 2022-04-26 Ptc医疗公司 (r)-2羟基-2-甲基-4-(2，4，5-三甲基-3，6-二氧环己-1，4-二烯基)丁酰胺的多晶型和无定形形式
US10815211B2 (en) * 2015-10-08 2020-10-27 Khondrion Ip B.V. Compounds for treating mitochondrial disease
JP7117241B2 (ja) 2015-12-16 2022-08-12 ピーティーシー セラピューティクス， インコーポレイテッド 混合されたトコール組成物からアルファ－トコトリエノールを富化するための改良された方法
CA3008849A1 (en) 2015-12-17 2017-06-22 Bioelectron Technology Corporation Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders
WO2017172914A1 (en) 2016-03-30 2017-10-05 Wisconsin Alumni Research Foundation Methods and compositions for modulating frataxin expression
CN109642904A (zh) 2016-05-23 2019-04-16 加州理工学院 调节肠微生物群来治疗神经退行性病症
JP2018083799A (ja) 2016-11-15 2018-05-31 バイオエレクトロン テクノロジー コーポレイション ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩
WO2018183679A1 (en) 2017-03-29 2018-10-04 Wisconsin Alumni Research Foundation Methods and compositions for modulating gene expression
MX2019011692A (es) * 2017-04-05 2020-02-10 Khondrion Ip B V Nuevo tratamiento de enfermedades mitocondriales.
JP7266304B2 (ja) 2017-04-21 2023-04-28 ユニヴァーシティー オブ タスマニア 治療化合物および方法
US11147792B2 (en) 2017-05-15 2021-10-19 Axial Therapeutics, Inc. Inhibitors of microbially induced amyloid
MX2020005238A (es) 2017-11-22 2020-08-24 Khondrion Ip B V Compuestos novedosos como inhibidores mpges-1.
CA3105542A1 (en) 2018-07-31 2020-02-06 Novartis Ag Crystalline forms of a lta4h inhibitor
JP7586815B2 (ja) 2018-10-17 2024-11-19 ピーティーシー セラピューティクス， インコーポレイテッド α－シヌクレイノパチー、タウオパチー、および他の障害を抑制および処置するための２，３，５－トリメチル－６－ノニルシクロヘキサ－２，５－ジエン－１，４－ジオン
NL2024431B1 (en) * 2019-12-11 2021-09-07 Sulfateq Bv Compounds for treatment of alzheimer’s disease
US20230029044A1 (en) 2020-02-21 2023-01-26 Sumitomo Pharma Co., Ltd. Optically resolved trolox intermediate and method for producing same
AU2022306868A1 (en) 2021-07-08 2024-02-22 Ptc Therapeutics, Inc. Pharmaceutical compositions comprising 2,3,5-trimethyl-6-nonylcyclohexa-2,5-diene-1,4-dione
JP7648009B2 (ja) 2022-06-09 2025-03-18 コニカミノルタ株式会社 モデル管理装置、モデル管理システム及びモデル管理方法
CN115417789B (zh) * 2022-09-03 2023-08-04 郑州大学 一种治疗帕金森氏病的化合物、其制备方法以及复方药物组合物和应用
CR20250133A (es) 2022-09-12 2025-06-26 Ptc Therapeutics Inc Granulos para suspension
KR20250073630A (ko) 2022-09-30 2025-05-27 피티씨 테라퓨틱스, 인크. 트롤록스 아미드의 산화적 절단 방법
WO2025117870A1 (en) 2023-12-01 2025-06-05 Ptc Therapeutics, Inc. Method of electrolytic oxidative cleavage of trolox amide
WO2025193975A1 (en) 2024-03-13 2025-09-18 Ptc Therapeutics, Inc. Formulations for stabilizing dissolution of medicaments

Family Cites Families (125)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US683982A (en) * 1901-04-29 1901-10-08 George Dudley Pogue Incandescent-lamp attachment.
US3947473A (en) 1972-12-22 1976-03-30 Hoffman-La Roche Inc. Antioxidant chroman compounds
US4026907A (en) 1973-11-19 1977-05-31 Hoffmann-La Roche Inc. Antioxidant chroman compounds
US4018799A (en) 1973-11-19 1977-04-19 Hoffmann-La Roche Inc. Antioxidant chroman compounds
JPS5640651A (en) 1979-09-12 1981-04-16 Takeda Chem Ind Ltd Quinone compound and its preparation
CA1338012C (en) 1987-04-27 1996-01-30 John Michael Mccall Pharmaceutically active amines
US5272180A (en) 1987-07-29 1993-12-21 Takeda Chemical Industries, Ltd. Cell proliferation inhibitor
AT395947B (de) 1989-02-03 1993-04-26 Tyrolia Freizeitgeraete Skibindung
JPH02250831A (ja) * 1989-03-23 1990-10-08 Kuraray Co Ltd ３，４―ジヒドロ―２ｈ―ベンゾピラン誘導体及びそれを有効成分とする抗消化性潰瘍剤
DE4000397A1 (de) * 1990-01-09 1991-07-11 Hoechst Ag Lipidselektive antioxidantien sowie deren herstellung und verwendung
US5348973A (en) 1990-10-09 1994-09-20 Rhone-Poulenc Chimie Resolution of hydroxychroman-2-carboxylic acid esters by enantiomeric hydrolysis
FR2676056B1 (fr) 1991-05-03 1993-07-16 Adir Nouveaux derives du benzopyranne leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
FR2696743B1 (fr) * 1992-10-12 1994-12-23 Adir Nouveaux composés de thiazolidine dione, leur procédé de préparation et les compositions pharmaceutiques les contenant.
JPH08104685A (ja) * 1993-09-03 1996-04-23 Takeda Chem Ind Ltd ラクトール誘導体、その製造法および用途
US6150402A (en) 1994-08-15 2000-11-21 Loma Linda University Medical Center Natriuretic compounds
KR100264348B1 (ko) 1994-12-28 2000-08-16 디르크 반테 항-죽종형성제로서 네비볼롤을 함유하는 조성물
AU6709896A (en) 1995-08-21 1997-03-12 Takeda Chemical Industries Ltd. Quinone compound, its production and use
US6232060B1 (en) 1996-01-19 2001-05-15 Galileo Laboratories, Inc. Assay system for anti-stress agents
US5801159A (en) 1996-02-23 1998-09-01 Galileo Laboratories, Inc. Method and composition for inhibiting cellular irreversible changes due to stress
AU3458997A (en) 1996-07-11 1998-02-09 Takeda Chemical Industries Ltd. Anti-beta-amyloid protein-induced cytotoxicity composition
JP3093170B2 (ja) * 1996-09-19 2000-10-03 株式会社ジャパンエナジー ヒドロキノン誘導体及びその医薬用途
US5821247A (en) 1996-09-19 1998-10-13 Japan Energy Corporation Hydroquinone derivative and pharmaceutical use thereof
FR2756284B1 (fr) * 1996-11-26 2000-04-28 Adir Nouveaux derives du benzopyrane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US6291464B1 (en) * 1997-02-17 2001-09-18 Fujisawa Pharmaceutical Co., Ltd. Aminopiperazine derivatives
JP3913329B2 (ja) 1997-09-11 2007-05-09 株式会社クラレ （±）−クロマンカルボン酸の光学分割法
JP2000281656A (ja) * 1998-08-05 2000-10-10 Nippon Soda Co Ltd フェニルアゾール化合物、製造法および抗高脂血症薬
FR2783519B1 (fr) 1998-09-23 2003-01-24 Sod Conseils Rech Applic Nouveaux derives d'amidines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant
EP1006108A1 (en) * 1998-12-01 2000-06-07 Cerebrus Pharmaceuticals Limited 3-Hydroxy-2(1H)-pyridinone or 3-hydroxy-4(1H)-pyridinone derivatives useful as reactive oxygen species (ROS) scavengers
JP2000191616A (ja) * 1998-12-24 2000-07-11 Senju Pharmaceut Co Ltd 新規ジペプチジルアルデヒド誘導体およびそれを含有する医薬
WO2000078296A2 (en) 1999-06-17 2000-12-28 Basf Aktiengesellschaft Tocotrienol and/or tocotrienol derivatives for the treatment or prophylaxis of glutamate- and/or calcium-induced disorders
US6426362B1 (en) 1999-10-08 2002-07-30 Galileo Laboratories, Inc. Formulations of tocopherols and methods of making and using them
US6528042B1 (en) 1999-10-08 2003-03-04 Galileo Laboratories, Inc. Compositions of flavonoids for use as cytoprotectants and methods of making and using them
IL149177A0 (en) * 1999-11-05 2002-11-10 Sod Conseils Rech Applic Novel heterocyclic compounds and their use as medicines
EP1381397B1 (en) * 2000-10-24 2007-02-28 CIS bio international Stabilisation of radiopharmaceutical compositions using a hydrophilic thioether or a hydrophilic 6-hydroxy chroman
AU2002239748A1 (en) 2000-12-15 2002-06-24 Galileo Laboratories, Inc. Use of tocopherol, metabolites or derivatives thereof or flavonoid metabolites or derivatives thereof in the manufacture of a medicament for the treatment of tissue ischemia
US7034054B2 (en) 2000-12-15 2006-04-25 Galileo Pharmaceuticals, Inc. Methods for the prevention and treatment of cerebral ischemia using non-alpha tocopherols
US6608196B2 (en) 2001-05-03 2003-08-19 Galileo Pharmaceuticals, Inc. Process for solid supported synthesis of pyruvate-derived compounds
NZ513547A (en) * 2001-08-13 2002-09-27 Antipodean Biotechnology Ltd Synthesis of triphenylphosphonium quinols (e.g. mitoquinol) and/or quinones (e.g. mitoquinone)
US7119117B2 (en) 2001-08-21 2006-10-10 Galileo Pharmaceuticals, Inc. Tocopherol enriched compositions and amelioration of inflammatory symptoms
EP1450787A4 (en) 2001-11-15 2006-01-25 Galileo Pharmaceuticals Inc FORMULATIONS AND METHODS FOR THE TREATMENT OR AMELIORATION OF INFLAMMATORY CONDITIONS
EP1463719A2 (en) * 2002-01-08 2004-10-06 Eisai Co., Ltd Eponemycin and epoxomicin analogs and uses thereof
US6667330B2 (en) 2002-01-31 2003-12-23 Galileo Pharmaceuticals, Inc. Furanone derivatives
US7078541B2 (en) 2002-02-07 2006-07-18 Galileo Pharmaceuticals, Inc. Benzofuran derivatives
US6653346B1 (en) 2002-02-07 2003-11-25 Galileo Pharmaceuticals, Inc. Cytoprotective benzofuran derivatives
GB0204232D0 (en) 2002-02-22 2002-04-10 Isis Innovation Assay
ATE328283T1 (de) 2002-07-01 2006-06-15 Santhera Pharmaceuticals Ch Screeningverfahren und verbindungen zur behandlung von friedreich ataxia
CA2504334A1 (en) 2002-10-30 2004-05-21 Galileo Pharmaceuticals, Inc. Identifying therapeutic compounds based on their physical-chemical properties
US20040097433A1 (en) 2002-11-15 2004-05-20 Sekhar Boddupalli Chroman derivatives for the reduction of inflammation symptoms
EP1454627A1 (en) 2003-03-06 2004-09-08 MyoContract Ltd. Alpha-Keto carbonyl calpain inhibitors
WO2005032544A1 (en) 2003-09-19 2005-04-14 Galileo Pharmaceuticals, Inc. Treatment of mitochondrial diseases
WO2005042497A2 (en) * 2003-10-28 2005-05-12 Vertex Pharmaceuticals, Incorporated Benzimidazoles useful as modulators of ion channels
US7393662B2 (en) 2004-09-03 2008-07-01 Centocor, Inc. Human EPO mimetic hinge core mimetibodies, compositions, methods and uses
FR2875803B1 (fr) 2004-09-24 2006-11-24 Catalys Sarl Preparation de composes phenol-amides a proprietes antioxydantes
GB0503434D0 (en) * 2005-02-18 2005-03-30 Senexis Ltd Amyloid-binding peptides, analogues and uses thereof
EP2564842A1 (en) 2005-06-01 2013-03-06 Edison Pharmaceuticals, Inc. Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
LT1933821T (lt) 2005-09-15 2020-11-10 Ptc Therapeutics, Inc. Šoninės grandinės variantai redoks aktyviųjų terapijos priemonių, skirtų mitochondrinių ligų ir kitokių būklių gydymui ir energijos biologinių žymenų moduliavimui
WO2007095630A2 (en) * 2006-02-15 2007-08-23 The Regents Of The University Of California New ubiquinone analogs and methods of use
CA2635280C (en) 2006-02-22 2017-12-12 Edison Pharmaceuticals, Inc. Side chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
US7786100B2 (en) 2006-03-20 2010-08-31 The Regents Of The University Of Michigan Composition and method of treating hearing loss
US8080676B2 (en) 2006-10-26 2011-12-20 Mitsubishi Gas Chemical Company, Inc. Method of producing S-(−)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid and product obtained by the method
CN101610782A (zh) 2007-01-10 2009-12-23 爱迪生药物公司 使用具有促红细胞生成素或血小板生成素活性的化合物治疗呼吸链紊乱
US7745665B2 (en) 2007-06-04 2010-06-29 Auspex Pharmaceuticals, Inc. Substituted phenethylamines
HUE028502T2 (en) * 2007-11-06 2016-12-28 Edison Pharmaceuticals Inc 4- (P-Quinonyl) -2-hydroxybutanamide derivatives for the treatment of mitochondrial diseases
WO2009088572A2 (en) 2008-01-07 2009-07-16 Centocor, Inc. Method of treating erythropoietin hyporesponsive anemias
WO2009089224A1 (en) 2008-01-08 2009-07-16 Edison Pharmaceuticals, Inc. (HET) ARYL-p-QUINONE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES
DE102008062858A1 (de) 2008-01-14 2009-07-16 Merck Patent Gmbh Flüssigkristallines Medium
WO2009111576A2 (en) 2008-03-05 2009-09-11 Edison Pharmaceuticals, Inc. 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES
JP2011513420A (ja) 2008-03-05 2011-04-28 エジソン ファーマシューティカルズ， インコーポレイテッド レドックス活性治療薬を用いる聴覚機能障害および平衡機能障害の処置
CA2723621A1 (en) 2008-05-15 2009-11-19 Edison Pharmaceuticals, Inc Treatment of hearing and balance impairments using compounds having erythropoietin activity
EP2303309A2 (en) 2008-05-22 2011-04-06 Edison Pharmaceuticals, Inc. Treatment of mitochondrial diseases with an erythropoietin mimetic
JP5266875B2 (ja) 2008-05-23 2013-08-21 三菱瓦斯化学株式会社 有機カルボン酸エステルからの光学活性有機カルボン酸の製造方法
JP5798481B2 (ja) 2008-06-25 2015-10-21 エジソン ファーマシューティカルズ， インコーポレイテッド 酸化ストレス疾患を治療するための２−ヘテロシクリルアミノアルキル−（ｐ−キノン）誘導体
US20100010100A1 (en) 2008-07-09 2010-01-14 Hinman Andrew W Dermatological compositions with anti-aging and skin even-toning properties
US20100029784A1 (en) 2008-07-30 2010-02-04 Hinman Andrew W Naphthoquinone compositions with anti-aging, anti-inflammatory and skin even-toning properties
US20100029706A1 (en) 2008-07-30 2010-02-04 Edison Parmaceuticals, Inc. a Delaware Corporation HYDROGENATED PYRIDO[4,3-b]INDOLES FOR THE TREATMENT OF OXIDATIVE STRESS
LT3827815T (lt) 2008-09-10 2023-10-10 Ptc Therapeutics, Inc. Psichologinių raidos sutrikimų gydymas oksidacijos redukcijos atžvilgiu aktyviais vaistais
CA2740773A1 (en) 2008-10-14 2010-04-22 Edison Pharmaceuticals, Inc. Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells
EA201692046A1 (ru) 2008-10-28 2017-06-30 Эдисон Фармасьютикалз, Инк. СПОСОБ ПОЛУЧЕНИЯ α-ТОКОТРИЕНОЛА И ЕГО ПРОИЗВОДНЫХ
KR101496340B1 (ko) 2008-10-31 2015-03-04 삼성전자주식회사 프로세서 및 메모리 제어 방법
US20120136048A1 (en) 2009-04-28 2012-05-31 Miller Guy M Topical, periocular, or intraocular use of tocotrienols for the treatment of ophthalmic diseases
CA2777479C (en) 2009-04-28 2017-10-17 Edison Pharmaceuticals, Inc. Treatment of leber's hereditary optic neuropathy and dominant optic atrophy with tocotrienol quinones
EA201101576A1 (ru) 2009-04-28 2012-04-30 Эдисон Фармасьютикалз, Инк. Лекарственная форма токотриенол хинонов для лечения офтальмических (глазных) заболеваний
JP2012531411A (ja) 2009-06-25 2012-12-10 アンペア ライフ サイエンシーズ，インコーポレイテッド トコトリエノールまたはトコトリエノール濃縮抽出物を用いた広汎性発達障害の処置
AU2010286704B2 (en) 2009-08-26 2016-10-20 Ptc Therapeutics, Inc. Methods for the prevention and treatment of cerebral ischemia
WO2011041452A2 (en) 2009-10-01 2011-04-07 Ampere Life Sciences, Inc. Mouse model for identifying compounds for the treatment of oxidative stress
US20110172312A1 (en) 2009-12-31 2011-07-14 Miller Guy M Treatment of leigh syndrome and leigh-like syndrome with tocotrienol quinones
US8464722B2 (en) 2010-03-04 2013-06-18 Medline Industries, Inc. Folded telescopic equipment drape and method of folding and using the same
SG184787A1 (en) 2010-03-09 2012-11-29 Edison Pharmaceuticals Inc Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same
WO2011113018A1 (en) 2010-03-12 2011-09-15 Ampere Life Sciences, Inc. Measurement and control of biological time
JP2013523816A (ja) 2010-04-06 2013-06-17 エジソン ファーマシューティカルズ， インコーポレイテッド 毛細血管拡張性運動失調症の治療
CA2797581A1 (en) 2010-04-27 2011-11-03 Edison Pharmaceuticals, Inc. Formulations of quinones for the treatment of ophthalmic diseases
US20120101169A1 (en) 2010-07-14 2012-04-26 Penwest Pharmaceuticals Co. Methods of providing anticoagulation effects in subjects
US20140031432A1 (en) 2010-08-06 2014-01-30 Ampere Life Sciences, Inc. Treatment of mitochondrial diseases with vitamin k
SG187744A1 (en) 2010-08-06 2013-03-28 Edison Pharmaceuticals Inc Treatment of mitochondrial diseases with naphthoquinones
US20120295985A1 (en) 2010-11-19 2012-11-22 Miller Guy M Methods for improving blood glucose control
WO2012154613A1 (en) 2011-05-06 2012-11-15 Edison Pharmaceuticals, Inc. Improved process for the preparation of d-alpha-tocotrienol from natural extracts
WO2012170773A1 (en) 2011-06-08 2012-12-13 Edison Pharmaceuticals, Inc. Adjunctive therapy for the treatment of mitochondrial disorders with quinones and naphthoquinones
EP2720689A4 (en) 2011-06-14 2014-11-26 Edison Pharmaceuticals Inc CATECHOL DERIVATIVES FOR THE TREATMENT OF DISEASES ASSOCIATED WITH OXIDATIVE STRESS
WO2013006736A1 (en) 2011-07-06 2013-01-10 Edison Pharmaceuticals, Inc Treatment of leigh syndrome and leigh-like syndrome, including complications of sucla2 mutations, with tocotrienol quinones
JP6728520B2 (ja) 2011-07-06 2020-07-22 ピーティーシー セラピューティクス， インコーポレイテッド メチルマロン酸尿症、イソ吉草酸尿症、および他の有機酸尿症のトコトリエノールキノンによる処置
WO2013013078A1 (en) 2011-07-19 2013-01-24 Edison Pharmeceuticals, Inc. Methods for selective oxidation of alpha tocotrienol in the presence of non-alpha tocotrienols
CN103781484A (zh) 2011-07-20 2014-05-07 赫思公司 治疗疼痛的方法
JP2015533794A (ja) 2012-09-07 2015-11-26 エジソン ファーマシューティカルズ， インコーポレイテッド 酸化ストレス障害を処置するためのベンゾキノン誘導体
EA031098B1 (ru) 2013-03-08 2018-11-30 Юнилевер Н.В. Соединения резорцина для дерматологического применения
US20140275045A1 (en) 2013-03-15 2014-09-18 Edison Pharmaceuticals, Inc. Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders
US9670170B2 (en) 2013-03-15 2017-06-06 Bioelectron Technology Corporation Resorufin derivatives for treatment of oxidative stress disorders
CA2906145A1 (en) 2013-03-15 2014-09-18 Edison Pharmaceuticals, Inc. Alkyl-heteroaryl substituted quinone derivatives for treatment of oxidative stress disorders
US9868711B2 (en) 2013-03-15 2018-01-16 Bioelectron Technology Corporation Phenazine-3-one and phenothiazine-3-one derivatives for treatment of oxidative stress disorders
US9296712B2 (en) 2013-03-15 2016-03-29 Edison Pharmaceuticals, Inc. Resorufin derivatives for treatment of oxidative stress disorders
EP3004071A1 (en) 2013-05-31 2016-04-13 Edison Pharmaceuticals, Inc. Carboxylic acid derivatives for treatment of oxidative stress disorders
CN107531616B (zh) 2014-12-16 2022-04-26 Ptc医疗公司 (r)-2羟基-2-甲基-4-(2，4，5-三甲基-3，6-二氧环己-1，4-二烯基)丁酰胺的多晶型和无定形形式
US20180002247A1 (en) 2014-12-16 2018-01-04 Bioelectron Technology Corporation Methods for chiral resolution of trolox
WO2016114860A1 (en) 2015-01-12 2016-07-21 Edison Pharmaceuticals, Inc. Quinones for protection against radiation exposure
JP7117241B2 (ja) 2015-12-16 2022-08-12 ピーティーシー セラピューティクス， インコーポレイテッド 混合されたトコール組成物からアルファ－トコトリエノールを富化するための改良された方法
CA3008849A1 (en) 2015-12-17 2017-06-22 Bioelectron Technology Corporation Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders
WO2017123823A1 (en) 2016-01-12 2017-07-20 Bioelectron Technology Corporation Alkyl-, acyl-, urea-, and aza-uracil sulfide:quinone oxidoreductase inhibitors
WO2017123820A1 (en) 2016-01-12 2017-07-20 Bioelectron Technology Corporation Methods for diagnosing and treating oxidative stress disorders using biomarkers
WO2018081644A1 (en) 2016-10-28 2018-05-03 Bioelectron Technology Corporation Methods of analyzing p-hydroquinone levels and ratios
JP2018083799A (ja) 2016-11-15 2018-05-31 バイオエレクトロン テクノロジー コーポレイション ２−置換アミノ−ナフト［１，２−ｄ］イミダゾール−５−オン化合物またはその製薬学上許容される塩
WO2018129411A1 (en) 2017-01-06 2018-07-12 Bioelectron Technology Corporation Aryl- and heteroaryl-resorufin derivatives for treatment of oxidative stress disorders and liver and kidney disorders
US20200121618A1 (en) 2017-04-14 2020-04-23 Bioelectron Technology Corporation Methods and compositions for treatment of inflammation and oxidative stress
US20180333389A1 (en) 2017-04-14 2018-11-22 Bioelectron Technology Corporation Vitamin e compositions and methods of use therefor
JP7586815B2 (ja) 2018-10-17 2024-11-19 ピーティーシー セラピューティクス， インコーポレイテッド α－シヌクレイノパチー、タウオパチー、および他の障害を抑制および処置するための２，３，５－トリメチル－６－ノニルシクロヘキサ－２，５－ジエン－１，４－ジオン
US20230002324A1 (en) 2019-06-13 2023-01-05 Ptc Therapeutics, Inc. Naphthoquinone derivatives for treatment of oxidative stress disorders
WO2021077034A1 (en) 2019-10-18 2021-04-22 Ptc Therapeutics, Inc. 2,3,5-trimethyl-6-nonylcyclohexa-2,5-diene-1,4-dione for suppressing and treating hemoglobinopathy, thalassemia, sickle cell disease and other disorders

Also Published As

Publication number Publication date
SI3456707T1 (sl) 2020-10-30
US9169196B2 (en) 2015-10-27
EP3456707A1 (en) 2019-03-20
MX338572B (es) 2016-04-22
CA2704473C (en) 2016-10-04
JP2014098025A (ja) 2014-05-29
EP3018122A1 (en) 2016-05-11
US10968166B2 (en) 2021-04-06
EA028911B1 (ru) 2018-01-31
PL3456707T3 (pl) 2020-09-21
DK3456707T3 (da) 2020-07-20
US10167251B2 (en) 2019-01-01
EP2220030B1 (en) 2016-01-13
US20090118257A1 (en) 2009-05-07
US20120122934A1 (en) 2012-05-17
EA038941B1 (ru) 2021-11-12
CA2704473A1 (en) 2009-05-14
US20210179542A1 (en) 2021-06-17
EA201000756A1 (ru) 2010-12-30
EP3733642B1 (en) 2024-05-08
MX2020004146A (es) 2020-08-13
WO2009061744A2 (en) 2009-05-14
EA201791981A1 (ru) 2018-01-31
MX2010004622A (es) 2010-05-20
US20190270699A1 (en) 2019-09-05
JP2016065103A (ja) 2016-04-28
US11840497B2 (en) 2023-12-12
JP2018021080A (ja) 2018-02-08
EP2220030A2 (en) 2010-08-25
US20130289034A1 (en) 2013-10-31
US20170313649A1 (en) 2017-11-02
JP2011503005A (ja) 2011-01-27
WO2009061744A3 (en) 2009-06-25
JP2020200344A (ja) 2020-12-17
JP2022093638A (ja) 2022-06-23
JP2022093639A (ja) 2022-06-23
US8519001B2 (en) 2013-08-27
JP7291831B2 (ja) 2023-06-15
PL2220030T3 (pl) 2016-07-29
EP3733642A1 (en) 2020-11-04
US20160075638A1 (en) 2016-03-17
SI2220030T1 (sl) 2016-04-29
JP5755881B2 (ja) 2015-07-29
EP3456707B1 (en) 2020-04-15
EP3018122B1 (en) 2018-10-10
HUE028502T2 (en) 2016-12-28
DK2220030T3 (en) 2016-04-11
HK1143804A1 (zh) 2011-01-14
US7968746B2 (en) 2011-06-28
US9546132B2 (en) 2017-01-17
JP2019131618A (ja) 2019-08-08

Similar Documents

Publication Publication Date Title
ES2564179T3 (es) Derivados de 4-(p-quinonil)-2-hidroxibutanamida para tratamiento de enfermedades mitocondriales
PE20221910A1 (es) Derivados de pirazolilo utiles como agentes anticancerigenos
CO6251251A2 (es) Derivados de pirazinona y su uso en el tratamiento de enfermedades pulmonares
AR070079A1 (es) Derivados de morfolino pirimidina usados en enfermedades relacionadas con mtor quinasa y/o p13k
AR085549A1 (es) DERIVADOS TRIAZOLIL PIPERAZINA Y TRIAZOLIL PIPERIDINA SUSTITUIDOS COMO MODULADORES DE g SECRETASA
CO6210729A2 (es) Derivados de sulfonil-fenil-2h-[1,2,4]oxadiazol-5-ona procedimientos para su preparacion y su uso como agente farmaceutico
AR107616A1 (es) Compuestos de 6,7-dihidro-5h-benzo[7]anuleno sustituidos, procesos para su preparación y usos terapéuticos de los mismos
AR079226A1 (es) Espiroindolinona- pirrolidinas, procesos de preparacion y uso de los mismos para el tratamiento y profilaxis del cancer
AR060401A1 (es) Derivados de cromen-2-ona
CO6251271A2 (es) Derivados de pirimidina trisustituida para el tratamiento de enfermedades proliferativas
AR092269A1 (es) Sulfamoilarilamidas y su uso como medicamentos para el tratamiento de la hepatitis b
AR044402A1 (es) Compuestos heterociclicos y su uso como inmunodepresores. composiciones farmaceuticas que los contienen.
AR077505A1 (es) Compuestos de piridina y sus usos
AR105522A1 (es) Derivados de amida sustituida que tienen actividad multimodal contra el dolor
AR061369A1 (es) Derivados de pirimidina y composiciones farmaceuticas que los comprenden
AR072952A1 (es) Compuestos de 2-imino-3-metilpirrolopirimidinona fenilo-sustituida como inhibidores de bace-1, composiciones y su uso
AR067613A1 (es) Inhibidores de adn-pk, uso y sintesis de los mismos
AR070479A1 (es) Derivado heterociclico fusionado y su uso
AR081426A1 (es) Derivados de pirazol inhibidores del receptor sigma
AR083760A1 (es) Agentes antibacterianos y composiciones farmaceuticas
AR048362A1 (es) Derivados de tetrahidronaftiridina y proceso para la preparacion de los mismos
AR065464A1 (es) Derivados de nicotinamida. composiciones farmaceuticas
AR076850A1 (es) Derivados sustituidos de indazol y aza-indazol como moduladores de la gamma secretasa.
AR059328A1 (es) Derivados de antranilamida-2-amino-heteroareno-carboxamida, un proceso para su obtencion, composiciones farmaceuticas que los contienen y el uso de estos compuestos para la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por cetp
AR075235A1 (es) Derivados de indol como agentes anticancer.