JP6289485B2 - Ｐｄｅ４のヘテロアリール阻害剤 - Google Patents

Ｐｄｅ４のヘテロアリール阻害剤 Download PDF

Info

Publication number
JP6289485B2
JP6289485B2 JP2015539801A JP2015539801A JP6289485B2 JP 6289485 B2 JP6289485 B2 JP 6289485B2 JP 2015539801 A JP2015539801 A JP 2015539801A JP 2015539801 A JP2015539801 A JP 2015539801A JP 6289485 B2 JP6289485 B2 JP 6289485B2
Authority
JP
Japan
Prior art keywords
formula
compound according
pde4
certain embodiments
lower alkyl
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
JP2015539801A
Other languages
English (en)
Japanese (ja)
Other versions
JP2016505512A5 (show.php
JP2016505512A (ja
Inventor
マーク イー ガーニー
マーク イー ガーニー
ティモシー ジェイ ハーゲン
ティモシー ジェイ ハーゲン
シュエシェン モー
シュエシェン モー
エー ベレクープ
エー ベレクープ
ドナ エル ロメロ
ドナ エル ロメロ
ロバート エフ キャンベル
ロバート エフ キャンベル
ジョエル アール ウォーカー
ジョエル アール ウォーカー
レイ ジュー
レイ ジュー
Original Assignee
テトラ ディスカバリー パートナーズ エルエルシー
テトラ ディスカバリー パートナーズ エルエルシー
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 テトラ ディスカバリー パートナーズ エルエルシー, テトラ ディスカバリー パートナーズ エルエルシー filed Critical テトラ ディスカバリー パートナーズ エルエルシー
Publication of JP2016505512A publication Critical patent/JP2016505512A/ja
Publication of JP2016505512A5 publication Critical patent/JP2016505512A5/ja
Application granted granted Critical
Publication of JP6289485B2 publication Critical patent/JP6289485B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • 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
    • 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
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/69—Boron compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • 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
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • 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
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
JP2015539801A 2012-10-25 2013-10-24 Ｐｄｅ４のヘテロアリール阻害剤 Active JP6289485B2 (ja)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201261718285P 2012-10-25 2012-10-25
US61/718,285 2012-10-25
US201261733675P 2012-12-05 2012-12-05
US61/733,675 2012-12-05
US201361776937P 2013-03-12 2013-03-12
US61/776,937 2013-03-12
PCT/US2013/066645 WO2014066659A1 (en) 2012-10-25 2013-10-24 Heteroaryl inhibitors of pde4

Publications (3)

Publication Number Publication Date
JP2016505512A JP2016505512A (ja) 2016-02-25
JP2016505512A5 JP2016505512A5 (show.php) 2016-12-15
JP6289485B2 true JP6289485B2 (ja) 2018-03-07

Family

ID=50545269

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2015539801A Active JP6289485B2 (ja) 2012-10-25 2013-10-24 Ｐｄｅ４のヘテロアリール阻害剤

Country Status (22)

Country Link
US (8) US9221843B2 (show.php)
EP (2) EP3842420B1 (show.php)
JP (1) JP6289485B2 (show.php)
KR (1) KR102189560B1 (show.php)
CN (1) CN104768932B (show.php)
AU (1) AU2013334236B2 (show.php)
BR (1) BR112015009168B1 (show.php)
CA (1) CA2886263C (show.php)
CL (1) CL2015001068A1 (show.php)
DK (1) DK2912019T3 (show.php)
ES (1) ES2871821T3 (show.php)
HR (1) HRP20230162T1 (show.php)
HU (1) HUE056251T2 (show.php)
IL (1) IL238409A (show.php)
LT (1) LT3842420T (show.php)
MX (1) MX368959B (show.php)
NZ (1) NZ705881A (show.php)
PL (1) PL2912019T3 (show.php)
PT (1) PT2912019T (show.php)
SG (1) SG11201502050XA (show.php)
SI (1) SI3842420T1 (show.php)
WO (1) WO2014066659A1 (show.php)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2014DN09346A (show.php) 2012-06-13 2015-07-17 Hoffmann La Roche
MA37940B1 (fr) 2012-09-25 2018-09-28 Hoffmann La Roche Derives d'octahydro-cyclopenta(c)pyrrole substitues inhibiteurs de l'autotaxine, utiles pour traiter les affections renales, hepatiques et inflammatoires, les affections du systeme nerveux, les maladies fibreuses.
LT3842420T (lt) 2012-10-25 2023-02-27 Tetra Discovery Partners Llc Pde4 heteroarilo inhibitoriai
BR112015018355A8 (pt) * 2013-02-04 2018-01-23 Gruenenthal Gmbh novos compostos de pirimidina condensados substituídos
EP2951161A1 (en) * 2013-02-04 2015-12-09 Grünenthal GmbH 4-amino substituted condensed pyrimidine compounds as pde4 inhibitors
AR095079A1 (es) 2013-03-12 2015-09-16 Hoffmann La Roche Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo
UA118201C2 (uk) 2013-11-26 2018-12-10 Ф. Хоффманн-Ля Рош Аг НОВИЙ ОКТАГІДРОЦИКЛОБУТА[1,2-c;3,4-c']ДИПІРОЛ-2-ІЛ
WO2015144609A1 (en) 2014-03-26 2015-10-01 F. Hoffmann-La Roche Ag Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors
EP3590939A1 (en) 2014-03-26 2020-01-08 F. Hoffmann-La Roche AG Bicyclic compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors
WO2016161268A1 (en) 2015-04-01 2016-10-06 Enanta Pharmaceuticals, Inc. Hepatitis b antviral agents
MA41898A (fr) 2015-04-10 2018-02-13 Hoffmann La Roche Dérivés de quinazolinone bicyclique
WO2016183266A1 (en) 2015-05-13 2016-11-17 Enanta Pharmaceuticals, Inc. Ehpatitis b antiviral agents
WO2017011552A1 (en) 2015-07-13 2017-01-19 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
US10301255B2 (en) 2015-07-22 2019-05-28 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
PE20180479A1 (es) 2015-09-04 2018-03-07 Hoffmann La Roche Nuevos derivados de fenoximetilo
PE20180451A1 (es) 2015-09-24 2018-03-05 Hoffmann La Roche Nuevos compuestos biciclicos como inhibidores de atx
MX2018002217A (es) 2015-09-24 2018-03-23 Hoffmann La Roche Nuevos compuestos biciclicos como inhibidores de autotaxina (atx).
CR20180057A (es) 2015-09-24 2018-04-02 Hoffmann La Roche Nuevos compuestos biciclicos como inhibidores duales de atx/ca.
CA2984585A1 (en) 2015-09-24 2017-03-30 F. Hoffmann-La Roche Ag New bicyclic compounds as dual atx/ca inhibitors
WO2017136403A1 (en) 2016-02-02 2017-08-10 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
BR112018067964B1 (pt) 2016-03-07 2024-01-16 Enanta Pharmaceuticals, Inc Composto, composição farmacêutica que o compreende e uso do referido composto
EP3468561A4 (en) * 2016-06-10 2019-12-04 Enanta Pharmaceuticals, Inc. ANTIVIRAL AGENTS AGAINST HEPATITIS B
EP3596060B1 (en) 2017-03-16 2023-09-20 F. Hoffmann-La Roche AG New bicyclic compounds as atx inhibitors
RU2019132254A (ru) 2017-03-16 2021-04-16 Ф. Хоффманн-Ля Рош Аг Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca
TWI811236B (zh) 2017-08-28 2023-08-11 美商因那塔製藥公司 B型肝炎抗病毒試劑
CN111108109A (zh) 2017-09-20 2020-05-05 利奥制药有限公司 取代的二氢噻吩并嘧啶及其作为磷酸二酯酶抑制剂的用途
WO2019113173A1 (en) 2017-12-06 2019-06-13 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
TW201936192A (zh) 2017-12-06 2019-09-16 美商因那塔製藥公司 B 型肝炎抗病毒試劑
PT3724196T (pt) 2017-12-15 2023-01-13 Union Therapeutics As Azetidina di-hidrotienopiridinas substituídas e a sua utilização como inibidores de fosfodiesterase
CN111712502B (zh) 2017-12-15 2023-10-27 联合疗法公司 取代的氮杂环丁烷二氢噻吩并嘧啶类化合物及其作为磷酸二酯酶抑制剂的用途
US11058678B2 (en) 2018-01-22 2021-07-13 Enanta Pharmaceuticals, Inc. Substituted heterocycles as antiviral agents
US10729688B2 (en) 2018-03-29 2020-08-04 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
US20210145838A1 (en) * 2018-04-05 2021-05-20 Universiteit Hasselt Selective pde4d inhibitors against demyelinating diseases
CN108997394A (zh) * 2018-06-12 2018-12-14 广州百霆医药科技有限公司 苯并氧杂硼杂环戊烷类化合物及其制备方法
CA3113235A1 (en) 2018-09-21 2020-03-26 Enanta Pharmaceuticals, Inc. Functionalized heterocycles as antiviral agents
EP3861001B1 (en) * 2018-10-05 2023-12-13 Pfizer Inc. Boron containing pde4 inhibitors
US11198693B2 (en) 2018-11-21 2021-12-14 Enanta Pharmaceuticals, Inc. Functionalized heterocycles as antiviral agents
CN111635400A (zh) 2019-03-02 2020-09-08 察略盛医药科技(上海)有限公司 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途
US11028050B2 (en) * 2019-04-18 2021-06-08 Tetra Discovery Partners, Inc. Salts and polymorphs of a PDE4 inhibitor
WO2020232470A1 (en) 2019-05-13 2020-11-19 Boragen, Inc. Chemical compounds
US11236111B2 (en) 2019-06-03 2022-02-01 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
WO2020247575A1 (en) 2019-06-04 2020-12-10 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
WO2020247561A1 (en) 2019-06-04 2020-12-10 Enanta Pharmaceuticals, Inc, Hepatitis b antiviral agents
JP7597781B2 (ja) * 2019-07-03 2024-12-10 ボラ，インコーポレーテッド 化学化合物
WO2021007488A1 (en) 2019-07-11 2021-01-14 Enanta Pharmaceuticals, Inc. Substituted heterocycles as antiviral agents
WO2021055425A2 (en) 2019-09-17 2021-03-25 Enanta Pharmaceuticals, Inc. Functionalized heterocycles as antiviral agents
US11802125B2 (en) 2020-03-16 2023-10-31 Enanta Pharmaceuticals, Inc. Functionalized heterocyclic compounds as antiviral agents
CN114149410B (zh) * 2020-09-07 2025-02-25 四川科伦博泰生物医药股份有限公司 吡啶并环类化合物及其制备方法和用途
WO2022099284A1 (en) * 2020-11-05 2022-05-12 Young Biopharma, Llc Novel capsaicin analogs and uses thereof
CN116133666A (zh) * 2020-12-25 2023-05-16 瑞石生物医药有限公司 一种硼酸酯衍生物及其用途
CN115521946B (zh) * 2022-10-14 2024-06-21 浙江玖世生物科技有限公司 一种TiOx基光酶催化剂合成(R)-1-[3,5-二(三氟甲基)]苯乙醇的方法
EP4640219A1 (en) * 2022-12-23 2025-10-29 Shionogi & Co., Ltd. Capsule or granules containing pde4 inhibitor
IL322980A (en) * 2023-02-28 2025-10-01 Innovstone Therapeutics Ltd Dihydrothionopyrimidine derivatives and their uses
WO2024213089A1 (zh) 2023-04-13 2024-10-17 上海壹迪生物技术有限公司 取代的二氢噻吩并嘧啶类化合物、其制备方法和应用
GB202306663D0 (en) 2023-05-05 2023-06-21 Union Therapeutics As Combination therapy
WO2025080415A1 (en) 2023-10-12 2025-04-17 Alto Neuroscience, Inc. Treatment of neuropsychiatric disorders with tilivapram
CN120398908A (zh) * 2024-02-01 2025-08-01 艾派克斯生物科技有限公司 Pde4b抑制剂及其药物组合物和用途
WO2025221488A1 (en) 2024-04-16 2025-10-23 Alto Neuroscience, Inc. Transdermal administration of pde4 inhibitors for reduction in adverse events

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK23392D0 (da) 1992-02-24 1992-02-24 Novo Nordisk As Heterocykliske forbindelser, deres anvendelse og fremstilling
FR2754260B1 (fr) 1996-10-04 1998-10-30 Adir Nouveaux derives substitues de biphenyle ou de phenylpyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO2000015645A1 (fr) 1998-09-11 2000-03-23 Kyorin Pharmaceutical Co., Ltd. Derives d'esters phosphoniques et leur procede de production
MXPA04008671A (es) 2002-03-08 2004-12-06 Lilly Co Eli Derivados de pirrol-2,5-diona y su uso como inhibidores de gsk-3.
US20050014767A1 (en) 2003-01-29 2005-01-20 Magnus Pfahl Benzoxazole, benzothiazole, and benzimidazole derivatives for the treatment of cancer and other diseases
JP2006123639A (ja) 2004-10-27 2006-05-18 Mitsubishi Electric Corp ホームドア状態認識システム
US20060293343A1 (en) * 2005-05-18 2006-12-28 Asahi Kasei Pharma Corporation Pyrimidine derivatives
WO2006123639A1 (ja) * 2005-05-18 2006-11-23 Asahi Kasei Pharma Corporation ピリミジン誘導体
US7919519B2 (en) 2005-11-23 2011-04-05 Epix Pharmaceuticals Inc. S1P receptor modulating compounds and use thereof
WO2009146388A1 (en) 2008-05-28 2009-12-03 The Trustees Of Columbia University In The City Of New York Voxel-based methods for assessing subjects using positron emission tomography
EP2348863A4 (en) * 2008-09-04 2012-03-07 Anacor Pharmaceuticals Inc BORN SMALL MOLECULES
RU2380890C1 (ru) 2008-10-17 2010-02-10 Государственное образовательное учреждение высшего профессионального образования Марийский государственный технический университет Способ испытания травяного покрова на прирусловой пойме реки
WO2010059838A2 (en) 2008-11-20 2010-05-27 Decode Genetics Ehf Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects
US9161927B2 (en) * 2009-02-27 2015-10-20 Boehringer Ingelheim International Gmbh Drug combinations containing PDE4 inhibitors and NSAIDs
EP2380890A1 (en) * 2010-04-23 2011-10-26 Almirall, S.A. New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors
US8889123B2 (en) * 2010-08-19 2014-11-18 Allergan, Inc. Compositions and soft tissue replacement methods
LT3842420T (lt) * 2012-10-25 2023-02-27 Tetra Discovery Partners Llc Pde4 heteroarilo inhibitoriai
BR112015018355A8 (pt) * 2013-02-04 2018-01-23 Gruenenthal Gmbh novos compostos de pirimidina condensados substituídos
WO2015048407A1 (en) 2013-09-26 2015-04-02 Tetra Discovery Partners, LLC Heteroaryl inhibitors of pde4
WO2016049595A1 (en) 2014-09-26 2016-03-31 Tetra Discovery Partners, LLC Heteroaryl inhibitors of pde4
US11028050B2 (en) * 2019-04-18 2021-06-08 Tetra Discovery Partners, Inc. Salts and polymorphs of a PDE4 inhibitor

Also Published As

Publication number Publication date
US20190055269A1 (en) 2019-02-21
US20200354384A1 (en) 2020-11-12
AU2013334236A1 (en) 2015-04-02
US20230024240A1 (en) 2023-01-26
US20230348501A1 (en) 2023-11-02
SG11201502050XA (en) 2015-04-29
EP2912019A4 (en) 2016-04-20
EP3842420A1 (en) 2021-06-30
WO2014066659A1 (en) 2014-05-01
US9221843B2 (en) 2015-12-29
EP3842420B1 (en) 2022-12-07
US20150119362A1 (en) 2015-04-30
WO2014066659A9 (en) 2015-02-12
US20160137672A1 (en) 2016-05-19
HRP20230162T1 (hr) 2023-04-14
DK2912019T3 (da) 2021-05-25
KR20150074004A (ko) 2015-07-01
LT3842420T (lt) 2023-02-27
CL2015001068A1 (es) 2016-01-04
HUE056251T2 (hu) 2022-02-28
EP2912019B1 (en) 2021-03-24
EP2912019A1 (en) 2015-09-02
US20170342094A1 (en) 2017-11-30
MX368959B (es) 2019-10-23
US11401286B2 (en) 2022-08-02
KR102189560B1 (ko) 2020-12-11
IL238409A0 (en) 2015-06-30
US20190270759A1 (en) 2019-09-05
SI3842420T1 (sl) 2023-04-28
US12264169B2 (en) 2025-04-01
AU2013334236B2 (en) 2018-04-05
US11767334B2 (en) 2023-09-26
NZ705881A (en) 2018-04-27
IL238409A (en) 2017-08-31
US10093686B2 (en) 2018-10-09
BR112015009168B1 (pt) 2022-09-27
US9777024B2 (en) 2017-10-03
BR112015009168A2 (pt) 2017-07-04
HK1208026A1 (en) 2016-02-19
CA2886263A1 (en) 2014-05-01
CA2886263C (en) 2021-04-13
CN104768932A (zh) 2015-07-08
JP2016505512A (ja) 2016-02-25
PT2912019T (pt) 2021-05-25
US10626129B2 (en) 2020-04-21
CN104768932B (zh) 2018-08-07
PL2912019T3 (pl) 2021-11-02
ES2871821T3 (es) 2021-11-02
MX2015005015A (es) 2015-11-23
US10364258B2 (en) 2019-07-30

Similar Documents

Publication Publication Date Title
US12264169B2 (en) Heteroaryl inhibitors of PDE4
US10723711B2 (en) 1,1,1-trifluoro-3-hydroxypropan-2-yl carbamate derivatives and 1,1,1-trifluoro-4-hydroxybutan-2-yl carbamate derivatives as MAGL inhibitors
AU2019416589B2 (en) Heterocyclic compound intermediate, preparation method therefor and application thereof
US20080021026A1 (en) Benzothiophene inhibitors of rho kinase
CN104725359B (zh) 取代的哌嗪化合物及其使用方法和用途
EP3080121A1 (en) Fused tricyclic benzimidazoles derivatives as modulators of tnf activity
TW201217362A (en) Heteroaryls and uses thereof
JP2017519025A (ja) チオフェン−２−イル−ピリジン−２−イル−１ｈ−ピラゾール−４−カルボン酸誘導体、および可溶性グアニル酸シクラーゼ活性化剤としてのその使用
CN106243088A (zh) 取代的哌嗪化合物及其使用方法和用途
HK40055452B (en) Heteroaryl inhibitors of pde4
HK40055452A (en) Heteroaryl inhibitors of pde4
TW202413357A (zh) 用於治療ＴＲＰＭ３介導之病症的吡唑并［１，５－ａ］吡啶衍生物

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20161024

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20161024

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20170906

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20171010

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20171220

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: 20180109

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20180206

R150 Certificate of patent or registration of utility model

Ref document number: 6289485

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

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

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250