JP5755881B2 - ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体 - Google Patents

ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体 Download PDF

Info

Publication number
JP5755881B2
JP5755881B2 JP2010532329A JP2010532329A JP5755881B2 JP 5755881 B2 JP5755881 B2 JP 5755881B2 JP 2010532329 A JP2010532329 A JP 2010532329A JP 2010532329 A JP2010532329 A JP 2010532329A JP 5755881 B2 JP5755881 B2 JP 5755881B2
Authority
JP
Japan
Prior art keywords
hydroxy
methyl
alkyl
trimethyl
dienyl
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
JP2010532329A
Other languages
English (en)
Japanese (ja)
Other versions
JP2011503005A (ja
JP2011503005A5 (https=
Inventor
オリオン ディー. ヤンコウスキー,
オリオン ディー. ヤンコウスキー,
キーロン イー. ウェッソン,
キーロン イー. ウェッソン,
ポール モーラード,
ポール モーラード,
ウィリアム ディー. シュレーダー,
ウィリアム ディー. シュレーダー,
Original Assignee
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
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
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 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, 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 filed Critical 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
Publication of JP2011503005A publication Critical patent/JP2011503005A/ja
Publication of JP2011503005A5 publication Critical patent/JP2011503005A5/ja
Application granted granted Critical
Publication of JP5755881B2 publication Critical patent/JP5755881B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70Carboxylic 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
    • C07C235/72Carboxylic 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
    • C07C235/80Carboxylic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/16Amides, e.g. hydroxamic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02Carboxylic 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
    • C07C235/32Carboxylic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70Carboxylic 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
    • C07C235/72Carboxylic 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
    • C07C235/76Carboxylic 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
    • C07C235/78Carboxylic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/26Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28Sulfones; 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic 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
    • C07D207/18Heterocyclic 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
    • C07D207/22Heterocyclic 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
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic 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
    • C07D207/18Heterocyclic 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
    • C07D207/22Heterocyclic 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
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • C07D207/2632-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/272-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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic 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
    • C07D211/36Heterocyclic 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
    • C07D211/40Oxygen atoms
    • C07D211/44Oxygen atoms attached in position 4
    • C07D211/46Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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
    • C07D213/36Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40Acylated substituent nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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
    • C07D213/44Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46Oxygen atoms
    • C07D213/50Ketonic radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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
    • C07D213/44Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46Oxygen atoms
    • C07D213/51Acetal radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D223/00Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic 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
    • C07D233/56Heterocyclic 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
    • C07D233/60Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic 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
    • C07D233/56Heterocyclic 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
    • C07D233/61Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/301,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/02Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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
    • C07D295/10Heterocyclic 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
    • C07D295/112Heterocyclic 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
    • C07D295/116Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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
    • C07D295/12Heterocyclic 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
    • C07D295/125Heterocyclic 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
    • C07D295/13Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/16Heterocyclic 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
    • C07D295/18Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/16Heterocyclic 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
    • C07D295/18Heterocyclic 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
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/16Heterocyclic 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
    • C07D295/18Heterocyclic 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
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/192Radicals derived from carboxylic acids from aromatic carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/22Heterocyclic 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
    • C07D295/24Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic 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
    • C07D307/10Heterocyclic 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
    • C07D307/14Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/66Benzo[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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/02Systems containing only non-condensed rings with a three-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems 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)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (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)
JP2010532329A 2007-11-06 2008-11-04 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体 Active JP5755881B2 (ja)

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
US61/002,126 2007-11-06
US61/002,127 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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2014029395A Division JP2014098025A (ja) 2007-11-06 2014-02-19 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体

Publications (3)

Publication Number Publication Date
JP2011503005A JP2011503005A (ja) 2011-01-27
JP2011503005A5 JP2011503005A5 (https=) 2012-12-20
JP5755881B2 true JP5755881B2 (ja) 2015-07-29

Family

ID=40474999

Family Applications (8)

Application Number Title Priority Date Filing Date
JP2010532329A Active JP5755881B2 (ja) 2007-11-06 2008-11-04 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2014029395A Withdrawn JP2014098025A (ja) 2007-11-06 2014-02-19 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2016006830A Withdrawn JP2016065103A (ja) 2007-11-06 2016-01-18 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2017213638A Withdrawn JP2018021080A (ja) 2007-11-06 2017-11-06 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2019091932A Withdrawn JP2019131618A (ja) 2007-11-06 2019-05-15 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2020152918A Pending JP2020200344A (ja) 2007-11-06 2020-09-11 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2022075910A Withdrawn JP2022093638A (ja) 2007-11-06 2022-05-02 ミトコンドリア病を治療するための4-(p-キノリル)-2-ヒドロキシブタンアミド誘導体
JP2022075911A Active JP7291831B2 (ja) 2007-11-06 2022-05-02 ミトコンドリア病を治療するための4-(p-キノリル)-2-ヒドロキシブタンアミド誘導体

Family Applications After (7)

Application Number Title Priority Date Filing Date
JP2014029395A Withdrawn JP2014098025A (ja) 2007-11-06 2014-02-19 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2016006830A Withdrawn JP2016065103A (ja) 2007-11-06 2016-01-18 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2017213638A Withdrawn JP2018021080A (ja) 2007-11-06 2017-11-06 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2019091932A Withdrawn JP2019131618A (ja) 2007-11-06 2019-05-15 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2020152918A Pending JP2020200344A (ja) 2007-11-06 2020-09-11 ミトコンドリア病を治療するための4−(p−キノリル)−2−ヒドロキシブタンアミド誘導体
JP2022075910A Withdrawn JP2022093638A (ja) 2007-11-06 2022-05-02 ミトコンドリア病を治療するための4-(p-キノリル)-2-ヒドロキシブタンアミド誘導体
JP2022075911A Active JP7291831B2 (ja) 2007-11-06 2022-05-02 ミトコンドリア病を治療するための4-(p-キノリル)-2-ヒドロキシブタンアミド誘導体

Country Status (12)

Country Link
US (7) US7968746B2 (https=)
EP (4) EP3456707B1 (https=)
JP (8) JP5755881B2 (https=)
CA (1) CA2704473C (https=)
DK (2) DK3456707T3 (https=)
EA (2) EA028911B1 (https=)
ES (1) ES2564179T3 (https=)
HU (1) HUE028502T2 (https=)
MX (3) MX2010004622A (https=)
PL (2) PL3456707T3 (https=)
SI (2) SI2220030T1 (https=)
WO (1) WO2009061744A2 (https=)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005033092A1 (en) 2003-09-19 2005-04-14 Galileo Pharmaceuticals, Inc. Chroman derivatives
EP2471530B1 (en) * 2005-06-01 2017-01-11 Edison Pharmaceuticals, Inc. Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
US9278085B2 (en) 2006-02-22 2016-03-08 Edison Pharmaceuticals, Inc. Side-chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
WO2009061744A2 (en) 2007-11-06 2009-05-14 Edison Pharmaceuticals, Inc. 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
EA023618B1 (ru) * 2008-01-08 2016-06-30 Эдисон Фармасьютикалз, Инк. Производные (гет)арил-п-хинона для лечения митохондриальных болезней
WO2009111576A2 (en) 2008-03-05 2009-09-11 Edison Pharmaceuticals, Inc. 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES
EP2262519A4 (en) * 2008-03-05 2011-03-23 Edison Pharmaceuticals Inc TREATMENT OF HEARING AND BALANCING DISORDERS WITH REDOXACTIVE THERAPEUTICS
WO2009158348A1 (en) * 2008-06-25 2009-12-30 Edison Pharmaceuticals, Inc. 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases
EP2344142B1 (en) 2008-09-10 2024-06-26 PTC Therapeutics, Inc. Treatment of pervasive developmental disorders with redox-active therapeutics
EP2362726B1 (en) 2008-10-14 2018-08-08 Bioelectron Technology Corporation Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells
CA2741767C (en) 2008-10-28 2017-09-12 Ptc Therapeutics, Inc. Process for the production of alpha-tocotrienol and derivatives
PL2424495T3 (pl) 2009-04-28 2018-06-29 Bioelectron Technology Corporation Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu
DK2470168T3 (en) * 2009-08-26 2018-05-07 Bioelectron Tech Corp PROCEDURES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCAM
JP5931884B2 (ja) 2010-10-07 2016-06-08 カリフォルニア インスティチュート オブ テクノロジー 自閉症の生菌療法
WO2012133896A1 (ja) 2011-03-31 2012-10-04 YANO Takamitsu ポリアミド化合物及びミトコンドリア遺伝子疾患治療用医薬組成物
US9428478B2 (en) 2011-06-13 2016-08-30 Emory University Piperazine derivatives, compositions, and uses related thereto
WO2012174286A1 (en) 2011-06-14 2012-12-20 Edison Pharmaceuticals, Inc. Catechol derivatives for treatment of oxidative stress diseases
JP2014520894A (ja) 2011-07-19 2014-08-25 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 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法
HRP20170532T4 (hr) 2012-07-12 2019-12-27 Khondrion Ip B.V. Derivati kromanila za liječenje mitohondrijske bolesti
HUE033757T2 (en) * 2012-07-12 2017-12-28 Khondrion Ip B V Chromanyl derivatives for treating mitochondrial disease
WO2014036182A2 (en) 2012-08-29 2014-03-06 California Institute Of Technology Diagnosis and treatment of autism spectrum disorder
CA2883879A1 (en) 2012-09-07 2014-03-13 Edison Pharmaceuticals, Inc. Quinone derivatives for use in the modulation of redox status of individuals
US9446015B2 (en) * 2012-10-23 2016-09-20 Nicox Science Ireland Quinone based nitric oxide donating compounds for ophthalmic use
NL2010010C2 (en) * 2012-12-19 2014-06-23 Sulfateq B V Compounds for protection of cells.
US9670170B2 (en) 2013-03-15 2017-06-06 Bioelectron Technology Corporation Resorufin derivatives for treatment of oxidative stress disorders
US10189830B2 (en) 2013-03-15 2019-01-29 Bioelectron Technology Corporation 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
EA201790811A1 (ru) 2014-10-30 2017-11-30 Калифорния Инститьют Оф Текнолоджи Содержащие бактерии композиции и способы для улучшения видов поведения при нарушениях неврологического развития
WO2016069801A1 (en) 2014-10-30 2016-05-06 California Institute Of Technology Compositions and methods comprising bacteria for improving behavior in neurodecelopmental disorders
US20180002247A1 (en) * 2014-12-16 2018-01-04 Bioelectron Technology Corporation Methods for chiral resolution of trolox
AU2015364640B2 (en) * 2014-12-16 2020-08-13 Ptc Therapeutics, Inc. Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide
ES3033538T3 (en) * 2015-10-08 2025-08-05 Khondrion Ip B V Novel compounds for treating mitochondrial disease
EP3390377B1 (en) 2015-12-16 2026-03-25 PTC Therapeutics, Inc. Improved methods for enriching alpha-tocotrienol from mixed tocol compositions
WO2017106803A1 (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
EP4707410A3 (en) 2016-05-23 2026-03-25 California Institute of Technology Regulate gut microbiota to treat neurodegenerative disorders
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
KR102660473B1 (ko) * 2017-04-05 2024-04-24 콘드리온 아이피 비.브이. 미토콘드리아 질환의 신규 치료
CN110582480B (zh) 2017-04-21 2023-11-10 塔斯马尼亚大学 治疗化合物和方法
WO2018213204A1 (en) 2017-05-15 2018-11-22 Axial Biotherapeutics, Inc. Inhibitors of microbially induced amyloid
CA3079483A1 (en) * 2017-11-22 2019-05-31 Khondrion Ip B.V. Compounds as mpges-1 inhibitors
ES2984584T3 (es) 2018-07-31 2024-10-30 Novartis Ag Formas cristalinas de un inhibidor de LTA4H
KR20210076956A (ko) 2018-10-17 2021-06-24 피티씨 테라퓨틱스, 인크. α-시누클레인병증, 타우병증 및 기타 장애를 억제 및 치료하기 위한 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온
NL2024431B1 (en) * 2019-12-11 2021-09-07 Sulfateq Bv Compounds for treatment of alzheimer’s disease
KR20220143897A (ko) 2020-02-21 2022-10-25 스미토모 파마 가부시키가이샤 광학 분할된 트롤록스 중간체 및 그 제조 방법
PE20240893A1 (es) 2021-07-08 2024-04-24 Ptc Therapeutics Inc Composiciones farmaceuticas que comprenden 2,3,5-trimetil-6-nonilciclohexa-2,5-dien-1,4-diona
US20250363412A1 (en) 2022-06-09 2025-11-27 Konica Minolta, Inc. Model management device, model management system, and model management method
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
EP4588473A1 (en) 2022-09-12 2025-07-23 PTC Therapeutics, Inc. Granules for suspension
EP4596530A1 (en) 2022-09-30 2025-08-06 PTC Therapeutics, Inc. Oxidative cleavage method of trolox amide
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
SK282144B6 (sk) 1994-12-28 2001-11-06 Janssen Pharmaceutica N. V. Liečivo na terapeutické a profylaktické ošetrenie degeneratívnych chorôb vaskulárneho systému a nervovej sústavy, ktoré súvisia s oxidačným stresom
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
DE69712888D1 (de) * 1996-07-11 2002-07-04 Takeda Chemical Industries Ltd ZUSAMMENSTELLUNGEN DIE beta-AMYLOID PROTEIN BEDINGTE ZYTOTOXIZITÄT VERHINDERN
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
EP0968201A2 (en) * 1997-02-17 2000-01-05 Fujisawa Pharmaceutical Co., Ltd. New 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
DE60026348T2 (de) 1999-11-05 2006-10-19 Societe De Conseils De Recherches Et D`Applications Scientifiques (S.C.R.A.S.) Heterocyclische verbindungen und ihre verwendung als medikamente
AU2002249863A1 (en) * 2000-10-24 2002-08-12 Diatide, Inc. Stabilization of radiopharmaceutical compositions using hydrophilic thioether or a hydrophilic 6-hydroxy chroman
US7034054B2 (en) 2000-12-15 2006-04-25 Galileo Pharmaceuticals, Inc. Methods for the prevention and treatment of cerebral ischemia using non-alpha tocopherols
WO2002047680A2 (en) 2000-12-15 2002-06-20 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
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)
WO2003015494A2 (en) 2001-08-21 2003-02-27 Galileo Pharmaceuticals, Inc. Tocopherol enriched compositions and amelioration of inflammatory symptoms
AU2002352726A1 (en) 2001-11-15 2003-06-10 Galileo Laboratories, Inc. Formulations and methods for treatment or amelioration of inflammatory conditions
JP4412586B2 (ja) * 2002-01-08 2010-02-10 エーザイ・アール・アンド・ディー・マネジメント株式会社 エポネマイシンおよびエポキソマイシン類似物およびそれらの用途
US6667330B2 (en) 2002-01-31 2003-12-23 Galileo Pharmaceuticals, Inc. Furanone derivatives
US6653346B1 (en) 2002-02-07 2003-11-25 Galileo Pharmaceuticals, Inc. Cytoprotective benzofuran derivatives
US7078541B2 (en) 2002-02-07 2006-07-18 Galileo Pharmaceuticals, Inc. Benzofuran derivatives
GB0204232D0 (en) 2002-02-22 2002-04-10 Isis Innovation Assay
DE60211875T2 (de) 2002-07-01 2006-10-26 Santhera Pharmaceuticals (Schweiz) Ag Screeningverfahren und Verbindungen zur Behandlung von Friedreich ataxia
JP4599292B2 (ja) 2002-10-30 2010-12-15 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 物理的−化学的特性に基づく治療用化合物の同定
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
WO2005033092A1 (en) 2003-09-19 2005-04-14 Galileo Pharmaceuticals, Inc. Chroman derivatives
EP1678145A2 (en) * 2003-10-28 2006-07-12 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
EP2471530B1 (en) 2005-06-01 2017-01-11 Edison Pharmaceuticals, Inc. Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
CA2622523C (en) * 2005-09-15 2014-02-18 Edison Pharmaceuticals, Inc. Tail variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
WO2007095630A2 (en) * 2006-02-15 2007-08-23 The Regents Of The University Of California New ubiquinone analogs and methods of use
US9278085B2 (en) * 2006-02-22 2016-03-08 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
EP2088144B1 (en) 2006-10-26 2011-12-28 Mitsubishi Gas Chemical Company, Inc. Method of producing s-(-)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid
WO2008086025A2 (en) 2007-01-10 2008-07-17 Edison Pharmaceuticals, Inc. Treatment of respiratory chain disorders using compounds having erythropoietin or thrombopoietin activity
US7745665B2 (en) 2007-06-04 2010-06-29 Auspex Pharmaceuticals, Inc. Substituted phenethylamines
WO2009061744A2 (en) * 2007-11-06 2009-05-14 Edison Pharmaceuticals, Inc. 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
WO2009088572A2 (en) 2008-01-07 2009-07-16 Centocor, Inc. Method of treating erythropoietin hyporesponsive anemias
EA023618B1 (ru) 2008-01-08 2016-06-30 Эдисон Фармасьютикалз, Инк. Производные (гет)арил-п-хинона для лечения митохондриальных болезней
CN105295954A (zh) 2008-01-14 2016-02-03 默克专利股份有限公司 液晶介质
WO2009111576A2 (en) 2008-03-05 2009-09-11 Edison Pharmaceuticals, Inc. 2-SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES
EP2262519A4 (en) 2008-03-05 2011-03-23 Edison Pharmaceuticals Inc TREATMENT OF HEARING AND BALANCING DISORDERS WITH REDOXACTIVE THERAPEUTICS
CA2723621A1 (en) 2008-05-15 2009-11-19 Edison Pharmaceuticals, Inc Treatment of hearing and balance impairments using compounds having erythropoietin activity
WO2009143268A2 (en) 2008-05-22 2009-11-26 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
WO2009158348A1 (en) 2008-06-25 2009-12-30 Edison Pharmaceuticals, Inc. 2-heterocyclylaminoalkyl-(p-quinone) derivatives for treatment of oxidative stress diseases
WO2010005989A1 (en) 2008-07-09 2010-01-14 Edison Pharmaceuticals, Inc. 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
WO2010014758A1 (en) 2008-07-30 2010-02-04 Edison Pharmaceuticals, Inc. Use of hydrogenated pyrido[4,3-b] indoles for the treatment of oxidative stress
EP2344142B1 (en) 2008-09-10 2024-06-26 PTC Therapeutics, Inc. Treatment of pervasive developmental disorders with redox-active therapeutics
EP2362726B1 (en) 2008-10-14 2018-08-08 Bioelectron Technology Corporation Treatment of oxidative stress disorders including contrast nephropathy, radiation damage and disruptions in the function of red cells
CA2741767C (en) 2008-10-28 2017-09-12 Ptc Therapeutics, Inc. Process for the production of alpha-tocotrienol and derivatives
KR101496340B1 (ko) 2008-10-31 2015-03-04 삼성전자주식회사 프로세서 및 메모리 제어 방법
PL2424495T3 (pl) 2009-04-28 2018-06-29 Bioelectron Technology Corporation Leczenie dziedzicznej neuropatii nerwów wzrokowych lebera i dominującego zaniku nerwu wzrokowego chinonami tokotrienolu
JP2012525397A (ja) 2009-04-28 2012-10-22 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 眼科疾患を治療するためのトコトリエノールキノンの製剤
EP2424360A4 (en) 2009-04-28 2012-10-03 Ampere Life Sciences Inc TOPICAL, PERIOCULAR OR INTRAOCULAR USE OF TOCOTRIENOLS FOR THE TREATMENT OF OPHTHALMIC DISEASES
EP2609921A1 (en) 2009-06-25 2013-07-03 Ampere Life Sciences, Inc. Treatment of pervasive developmental disorders with tocotrienols or tocotrienol enriched extracts
DK2470168T3 (en) 2009-08-26 2018-05-07 Bioelectron Tech Corp PROCEDURES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCAM
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
AU2011238525A1 (en) 2010-04-06 2012-11-08 Edison Pharmaceuticals, Inc. Treatment of Ataxia Telangiectasia
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
EA201300215A1 (ru) 2010-08-06 2013-07-30 Эдисон Фармасьютикалз, Инк. Лечение митохондриальных болезней нафтохинонами
EP2601168A4 (en) 2010-08-06 2013-12-04 Ampere Life Sciences Inc TREATMENT OF MITOCHONDRIAL DISEASES BY VITAMIN K
WO2012068552A1 (en) 2010-11-19 2012-05-24 Edison Pharmaceuticals, Inc. 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
WO2012174286A1 (en) 2011-06-14 2012-12-20 Edison Pharmaceuticals, Inc. Catechol derivatives for treatment of oxidative stress diseases
US20150057363A1 (en) 2011-07-06 2015-02-26 Guy M. Miller Treatment of methylmalonic aciduria, isovaleric aciduria, and other organic acidurias with tocotrienol quinones
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
JP2014520894A (ja) 2011-07-19 2014-08-25 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 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法
MY166036A (en) 2011-07-20 2018-05-21 Hospira Inc Methods of treating pain
CA2883879A1 (en) 2012-09-07 2014-03-13 Edison Pharmaceuticals, Inc. Quinone derivatives for use in the modulation of redox status of individuals
EA031098B1 (ru) 2013-03-08 2018-11-30 Юнилевер Н.В. Соединения резорцина для дерматологического применения
US9670170B2 (en) 2013-03-15 2017-06-06 Bioelectron Technology Corporation Resorufin derivatives for treatment of oxidative stress disorders
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
US9296712B2 (en) 2013-03-15 2016-03-29 Edison Pharmaceuticals, Inc. Resorufin 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
US10189830B2 (en) 2013-03-15 2019-01-29 Bioelectron Technology Corporation Alkyl-heteroaryl substituted quinone derivatives for treatment of oxidative stress disorders
AU2014273891A1 (en) 2013-05-31 2015-12-24 Bioelectron Technology Corporation Carboxylic acid derivatives for treatment of oxidative stress disorders
AU2015364640B2 (en) 2014-12-16 2020-08-13 Ptc Therapeutics, Inc. Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide
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
EP3390377B1 (en) 2015-12-16 2026-03-25 PTC Therapeutics, Inc. Improved methods for enriching alpha-tocotrienol from mixed tocol compositions
WO2017106803A1 (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
JP2019501974A (ja) 2016-01-12 2019-01-24 バイオエレクトロン テクノロジー コーポレイション チオスルフェートレベルを増加させるためのまたは硫化水素レベルを低下させるためのトコフェロールキノン誘導体およびトコトリエノールキノン誘導体
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
US20180333389A1 (en) 2017-04-14 2018-11-22 Bioelectron Technology Corporation Vitamin e compositions and methods of use therefor
WO2018191732A1 (en) 2017-04-14 2018-10-18 Bioelectron Technology Corporation Methods and compositions for treatment of inflammation and oxidative stress
KR20210076956A (ko) 2018-10-17 2021-06-24 피티씨 테라퓨틱스, 인크. α-시누클레인병증, 타우병증 및 기타 장애를 억제 및 치료하기 위한 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온
WO2020252414A1 (en) 2019-06-13 2020-12-17 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
MX338572B (es) 2016-04-22
EP3733642B1 (en) 2024-05-08
EA201000756A1 (ru) 2010-12-30
MX2010004622A (es) 2010-05-20
JP2020200344A (ja) 2020-12-17
EP3018122B1 (en) 2018-10-10
WO2009061744A3 (en) 2009-06-25
US11840497B2 (en) 2023-12-12
JP2022093639A (ja) 2022-06-23
ES2564179T3 (es) 2016-03-18
EP3733642A1 (en) 2020-11-04
JP7291831B2 (ja) 2023-06-15
HK1143804A1 (zh) 2011-01-14
WO2009061744A2 (en) 2009-05-14
US20130289034A1 (en) 2013-10-31
US7968746B2 (en) 2011-06-28
EA028911B1 (ru) 2018-01-31
US10968166B2 (en) 2021-04-06
SI3456707T1 (sl) 2020-10-30
DK2220030T3 (en) 2016-04-11
US20120122934A1 (en) 2012-05-17
EP3456707B1 (en) 2020-04-15
EA201791981A1 (ru) 2018-01-31
PL3456707T3 (pl) 2020-09-21
JP2018021080A (ja) 2018-02-08
US20160075638A1 (en) 2016-03-17
JP2016065103A (ja) 2016-04-28
US9169196B2 (en) 2015-10-27
JP2011503005A (ja) 2011-01-27
EP3018122A1 (en) 2016-05-11
EA038941B1 (ru) 2021-11-12
US9546132B2 (en) 2017-01-17
US8519001B2 (en) 2013-08-27
CA2704473C (en) 2016-10-04
US20190270699A1 (en) 2019-09-05
PL2220030T3 (pl) 2016-07-29
EP3456707A1 (en) 2019-03-20
DK3456707T3 (da) 2020-07-20
JP2014098025A (ja) 2014-05-29
US20210179542A1 (en) 2021-06-17
HUE028502T2 (en) 2016-12-28
SI2220030T1 (sl) 2016-04-29
EP2220030A2 (en) 2010-08-25
JP2019131618A (ja) 2019-08-08
CA2704473A1 (en) 2009-05-14
US20170313649A1 (en) 2017-11-02
US20090118257A1 (en) 2009-05-07
US10167251B2 (en) 2019-01-01
JP2022093638A (ja) 2022-06-23
MX2020004146A (es) 2020-08-13
EP2220030B1 (en) 2016-01-13

Similar Documents

Publication Publication Date Title
JP7291831B2 (ja) ミトコンドリア病を治療するための4-(p-キノリル)-2-ヒドロキシブタンアミド誘導体
JP2011503005A5 (https=)
JP5710277B2 (ja) 酸化ストレス疾患の処置のための2−置換−p−キノン誘導体
US9486435B2 (en) (Het)aryl-p-quinone derivatives for treatment of mitochondrial diseases
JP2016520621A (ja) 酸化ストレス障害の処置のためのカルボン酸誘導体
HK40010622B (en) 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
HK40010622A (en) 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
ES2805081T3 (es) Derivados de 4-(p-quinonil)-2-hidroxibutanamida para el tratamiento de enfermedades mitocondriales
HK1143804B (en) 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20111104

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20121023

A524 Written submission of copy of amendment under article 19 pct

Free format text: JAPANESE INTERMEDIATE CODE: A524

Effective date: 20121023

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20130808

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20130819

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140219

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140903

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20141203

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20150512

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20150528

R150 Certificate of patent or registration of utility model

Ref document number: 5755881

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

S533 Written request for registration of change of name

Free format text: JAPANESE INTERMEDIATE CODE: R313533

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

S111 Request for change of ownership or part of ownership

Free format text: JAPANESE INTERMEDIATE CODE: R313113

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

S531 Written request for registration of change of domicile

Free format text: JAPANESE INTERMEDIATE CODE: R313531

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250