JP2017532357A - ジヘテロアリールヒストンデアセチラーゼインヒビターおよび治療におけるその使用 - Google Patents

ジヘテロアリールヒストンデアセチラーゼインヒビターおよび治療におけるその使用 Download PDF

Info

Publication number
JP2017532357A
JP2017532357A JP2017522844A JP2017522844A JP2017532357A JP 2017532357 A JP2017532357 A JP 2017532357A JP 2017522844 A JP2017522844 A JP 2017522844A JP 2017522844 A JP2017522844 A JP 2017522844A JP 2017532357 A JP2017532357 A JP 2017532357A
Authority
JP
Japan
Prior art keywords
alkyl
mmol
compound according
heteroaryl
independently selected
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.)
Pending
Application number
JP2017522844A
Other languages
English (en)
Japanese (ja)
Other versions
JP2017532357A5 (enExample
Inventor
スティーブン ジョセフ シャトルワース，
スティーブン ジョセフ シャトルワース，
アレクサンダー リチャード リアム セシル，
アレクサンダー リチャード リアム セシル，
ソマール マクコーミック，
ソマール マクコーミック，
ウィリアム ジョン ノーズ，
ウィリアム ジョン ノーズ，
シリル デイビー トマッシ，
シリル デイビー トマッシ，
フランク アレクサンドル シルバ，
フランク アレクサンドル シルバ，
Original Assignee
カルス セラピューティクス リミテッド
カルス セラピューティクス リミテッド
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 カルス セラピューティクス リミテッド, カルス セラピューティクス リミテッド filed Critical カルス セラピューティクス リミテッド
Publication of JP2017532357A publication Critical patent/JP2017532357A/ja
Publication of JP2017532357A5 publication Critical patent/JP2017532357A5/ja
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • 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
    • 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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines 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
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/519—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
    • A61K31/535—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
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Obesity (AREA)
  • Oncology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Reproductive Health (AREA)
  • Hospice & Palliative Care (AREA)
  • Emergency Medicine (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
JP2017522844A 2014-10-29 2015-10-29 ジヘテロアリールヒストンデアセチラーゼインヒビターおよび治療におけるその使用 Pending JP2017532357A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB1419228.0A GB201419228D0 (en) 2014-10-29 2014-10-29 Compounds
GB1419228.0 2014-10-29
PCT/GB2015/053260 WO2016067040A1 (en) 2014-10-29 2015-10-29 Diheteroaryl histone deacetylase inhibitors and their use in therapy

Publications (2)

Publication Number Publication Date
JP2017532357A true JP2017532357A (ja) 2017-11-02
JP2017532357A5 JP2017532357A5 (enExample) 2018-08-30

Family

ID=52103566

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2017522844A Pending JP2017532357A (ja) 2014-10-29 2015-10-29 ジヘテロアリールヒストンデアセチラーゼインヒビターおよび治療におけるその使用

Country Status (13)

Country Link
US (1) US10407435B2 (enExample)
EP (1) EP3212625A1 (enExample)
JP (1) JP2017532357A (enExample)
KR (1) KR20170081194A (enExample)
CN (1) CN107001340A (enExample)
AU (1) AU2015340305B2 (enExample)
BR (1) BR112017008794A2 (enExample)
CA (1) CA2966072A1 (enExample)
GB (1) GB201419228D0 (enExample)
IL (1) IL251860A0 (enExample)
MX (1) MX2017005422A (enExample)
SG (1) SG11201703492RA (enExample)
WO (1) WO2016067040A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112237994A (zh) * 2020-09-21 2021-01-19 昆明冶金研究院有限公司 一种多金属硫化矿硫化锌高效抑制剂及其制备方法与应用

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9676765B2 (en) * 2012-11-07 2017-06-13 Karus Therapeutics Limited Histone deacetylase inhibitors and their use in therapy
NZ714283A (en) 2013-05-10 2020-04-24 Karus Therapeutics Ltd Novel histone deacetylase inhibitors
GB201419228D0 (en) 2014-10-29 2014-12-10 Karus Therapeutics Ltd Compounds
GB201419264D0 (en) 2014-10-29 2014-12-10 Karus Therapeutics Ltd Compounds
WO2016094307A1 (en) 2014-12-08 2016-06-16 The Research Foundation For The State University Of New York Anti-fungals targeting the synthesis of fungal shingolipids
EP3638649A4 (en) 2017-06-16 2021-03-17 The Research Foundation for The State University of New York Anti-fungals compounds targeting the synthesis of fungal sphingolipids
CA3144985A1 (en) 2019-06-27 2020-12-30 The George Washington University, A Congressionally Chartered Not-For-Profit Corporation Hdac6-activated macrophages, compositions, and uses thereof
US11850233B2 (en) 2019-10-28 2023-12-26 Matibur Rahaman Zamadar Reduced adaptive microbial resistance treatment for flesh eating disease (necrotizing fasciitis)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55118472A (en) * 1979-03-03 1980-09-11 Hoechst Ag Triazole substituted hydroatropic acid derivative*its manufacture and plant protecting agent containing same
WO1992022536A1 (de) * 1991-06-14 1992-12-23 Schering Aktiengesellschaft, Berlin Und Bergkamen Bicyclisch substituierte vinylimidazole, -triazole und -tetrazole
JPH0532662A (ja) * 1990-11-09 1993-02-09 Nissan Chem Ind Ltd 置換ピラゾール誘導体および農園芸用殺菌剤
JPH07285953A (ja) * 1994-03-30 1995-10-31 F Hoffmann La Roche Ag 新規な、単環式又は二環式ｄｎａジャイレース阻害剤
WO2007085540A1 (en) * 2006-01-27 2007-08-02 Glaxo Group Limited 1h-indaz0l-4-yl-2 , 4-pyrimidinediamine derivatives
WO2009063240A1 (en) * 2007-11-16 2009-05-22 Arrow Therapeutics Limited 2,4-diaminopyrimidine derivatives useful as inhibitors of aurora kinase
JP2010523601A (ja) * 2007-04-09 2010-07-15 メシルジーン インコーポレイテッド ヒストンデアセチラーゼ阻害剤
JP2012516317A (ja) * 2009-01-28 2012-07-19 カルス セラピューティクス リミテッド スクリプタイドアイソスター（ｓｃｒｉｐｔａｉｄｉｓｏｓｔｅｒｅｓ）およびその治療における使用
WO2014072714A1 (en) * 2012-11-07 2014-05-15 Karus Therapeutics Ltd Novel histone deacetylase inhibitors and their use in therapy

Family Cites Families (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017500A (en) 1973-07-16 1977-04-12 Schering Corporation Certain 8-amino-1,7-naphthyridines
US4792562A (en) 1985-12-04 1988-12-20 Hoechst-Roussel Pharmaceuticals, Inc. N-(pyrrol-1-yl)pyridinamines having memory enhancing activity
US5214038A (en) 1991-04-15 1993-05-25 Hoechst-Roussel Pharmaceuticals Inc. 1-(pyrido[3,4-b]-1,4-oxazinyl-4-yl)-1H-indoles and intermediates for the preparation thereof
JP2000511883A (ja) 1996-04-19 2000-09-12 ノボ ノルディスク アクティーゼルスカブ ホスホチロシン認識ユニットを有する分子のモジュレーター
EP0887348A1 (en) 1997-06-25 1998-12-30 Boehringer Mannheim Italia S.p.A. Bis-Indole derivatives having antimetastatic activity, a process for their preparation and pharmaceutical compositions containing them
JP3712529B2 (ja) 1998-04-24 2005-11-02 大鵬薬品工業株式会社 ３，３−ジピリジルアクリル酸アミド誘導体又はその薬学的に許容される塩
JP5278983B2 (ja) 1999-11-17 2013-09-04 塩野義製薬株式会社 アミド化合物の新規用途
GB9929988D0 (en) 1999-12-17 2000-02-09 Celltech Therapeutics Ltd Chemical compounds
US6608053B2 (en) 2000-04-27 2003-08-19 Yamanouchi Pharmaceutical Co., Ltd. Fused heteroaryl derivatives
CN1186324C (zh) 2000-04-27 2005-01-26 山之内制药株式会社 稠合杂芳基衍生物
AU2001270260A1 (en) 2000-06-30 2002-01-14 Sugen, Inc. 4-heteroaryl-3-heteroarylidenyl-2-indolinones and their use as protein kinase inhibitors
JP2002255964A (ja) 2000-10-24 2002-09-11 Sankyo Co Ltd イミダゾピリジン誘導体
WO2002034748A1 (fr) 2000-10-24 2002-05-02 Sankyo Company, Limited Derives d'imidazopyridine
US6905669B2 (en) 2001-04-24 2005-06-14 Supergen, Inc. Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase
US7429593B2 (en) 2001-09-14 2008-09-30 Shionogi & Co., Ltd. Utilities of amide compounds
ES2322950T3 (es) 2002-03-13 2009-07-02 Janssen Pharmaceutica Nv Derivados de aminocarbonilo como nuevos inhibidores de histona-desacetilasa.
JP2003313126A (ja) 2002-04-23 2003-11-06 Sankyo Co Ltd イミダゾピリジン誘導体を有効成分とする医薬
JP2004002826A (ja) 2002-04-24 2004-01-08 Sankyo Co Ltd 高分子イミダゾピリジン誘導体
JP4235726B2 (ja) 2002-11-19 2009-03-11 国立大学法人 奈良先端科学技術大学院大学 大きな二光子吸収特性を示すアセチレン結合により連結されたビス（イミダゾリルポルフィリン金属錯体）を構成単位とするポルフィリン連鎖体及びその製造方法
AU2003900608A0 (en) 2003-02-11 2003-02-27 Fujisawa Pharmaceutical Co., Ltd. Hdac inhibitor
EP1724267B1 (en) 2004-02-26 2013-11-06 ASKA Pharmaceutical Co., Ltd. Pyrimidine derivative
MXPA06014018A (es) 2004-06-01 2007-02-08 Hoffmann La Roche 3-amino-1-arilpropil-indoles como inhibidores de reabsorcion de monoaminas.
US20090110720A1 (en) 2004-10-06 2009-04-30 Anders Nykjaer Use of compounds for the prevention of drug-induced cell toxicity
GB0423653D0 (en) 2004-10-25 2004-11-24 Piramed Ltd Pharmaceutical compounds
JP2008530136A (ja) 2005-02-14 2008-08-07 ミイカナ セラピューティクス インコーポレイテッド ヒストンデアセチラーゼの阻害剤として有用な縮合複素環化合物
EP2491926B1 (en) 2005-03-22 2018-05-09 President and Fellows of Harvard College Treatment of protein degradation disorders
JP2008545660A (ja) 2005-05-20 2008-12-18 バーテックス ファーマシューティカルズ インコーポレイテッド プロテインキナーゼ阻害剤として有用なピロロピリジン化合物
TW200716545A (en) 2005-06-10 2007-05-01 Sigma Tau Ind Farmaceuti Indole derivatives having anti-tumor activity
WO2007050348A2 (en) 2005-10-21 2007-05-03 Merck & Co., Inc. Potassium channel inhibitors
WO2007084667A2 (en) 2006-01-19 2007-07-26 Osi Pharmaceutical, Inc. Fused heterobicyclic kinase inhibitors
JP5302186B2 (ja) 2006-04-26 2013-10-02 エフ．ホフマン−ラ ロシュ アーゲー Ｐｉ３ｋ阻害剤としてのピリミジン誘導体
CN101511840A (zh) 2006-04-26 2009-08-19 吉宁特有限公司 磷酸肌醇3-激酶抑制剂化合物及其使用方法
WO2008007780A1 (fr) 2006-07-13 2008-01-17 Kyowa Hakko Kirin Co., Ltd. Dérivé du pentadiènamide
CN101534831B (zh) 2006-09-11 2013-07-17 柯瑞斯公司 包含锌结合基团的取代的酪氨酸抑制剂
ES2532899T3 (es) 2006-10-28 2015-04-01 Methylgene Inc. Derivados de dibenzo[b,f][1,4]oxazepina como inhibidores de histona desacetilasa
JP5178731B2 (ja) 2006-11-22 2013-04-10 カルス セラピューティクス リミテッド デプシペプチドおよびその治療的使用
JP2010518014A (ja) 2007-01-31 2010-05-27 バーテックス ファーマシューティカルズ インコーポレイテッド キナーゼ阻害剤として有用な２−アミノピリジン誘導体
CN101663276A (zh) 2007-01-31 2010-03-03 沃泰克斯药物股份有限公司 用作激酶抑制剂的2-氨基吡啶衍生物
WO2008139987A1 (ja) 2007-04-26 2008-11-20 Japan Science And Technology Agency Ｇタンパク質共役型レセプタ－作動剤
WO2008137270A1 (en) 2007-05-04 2008-11-13 H. Lundbeck A/S Methods of diagnosing and monitoring of npy y5 based disorders
EP2154965A4 (en) 2007-05-29 2011-08-17 Glaxosmithkline Llc NAPHTHYRIDINE DERIVATIVES AS P13 KINASE INHIBITORS
GB0710528D0 (en) 2007-06-01 2007-07-11 Glaxo Group Ltd Novel compounds
WO2009137462A2 (en) 2008-05-05 2009-11-12 Envivo Pharmaceuticals, Inc. Methods for treating cognitive disorders using inhibitors of histone deacetylase
JP2011529932A (ja) 2008-08-05 2011-12-15 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 置換ナフチリジン及び医薬としてのその使用
US20110257170A1 (en) 2008-10-03 2011-10-20 Merck Serono Sa 4-morpholino-pyrido[3,2-d]pyrimidines
GB2465405A (en) 2008-11-10 2010-05-19 Univ Basel Triazine, pyrimidine and pyridine analogues and their use in therapy
BR112012003955A2 (pt) 2009-08-20 2017-09-26 Karus Therapeutics Ltd compostos heterocíclicos tricíclicos como inibidores da fosfoinositídeos 3-quinase
GB201007347D0 (en) 2010-04-30 2010-06-16 Karus Therapeutics Ltd Compounds
ES2647368T3 (es) 2010-10-08 2017-12-21 Vib Vzw Inhibidores de HDAC para tratar la enfermedad de Charcot-Marie-Tooth
AR084312A1 (es) 2010-12-16 2013-05-08 Genentech Inc Compuestos triciclicos inhibidores de la pi3k y composiciones farmaceuticas
CA2825599C (en) 2011-02-01 2021-07-13 The Board Of Trustees Of The University Of Illinois 4-methyl-n-hydroxybenzamide compounds as histone deacetylase (hdac) inhibitors
EP2508510A1 (en) 2011-04-06 2012-10-10 Ikerchem, S.L. Hydroxyphenyl pyrrole compounds containing an hydroxamic acid as hdac inhibitors and medicinal applications thereof
JP6169076B2 (ja) 2011-07-20 2017-07-26 ザ ジェネラル ホスピタル コーポレイション 骨疾患の処置のためのヒストン脱アセチル化酵素６選択的阻害剤
CA2850757A1 (en) 2011-10-03 2013-04-11 The Trustees Of Columbia University In The City Of New York Novel molecules that selectively inhibit histone deacetylase 6 relative to histone deacetylase 1
PH12014500724A1 (en) 2011-10-04 2014-05-19 Institute For Hepatitis And Virus Res Substituted aminothiazoles as inhibitors of cancers, including hepatocellular carcinoma, and as inhibitors of hepatitis virus replication
EP2790705B1 (en) 2011-12-15 2017-12-06 Novartis AG Use of inhibitors of the activity or function of pi3k
KR101415742B1 (ko) 2011-12-21 2014-07-04 영남대학교 산학협력단 6―아미노피리딘―3―올 유도체 또는 이의 약제학적 허용가능한 염 및 이를 유효성분으로 함유하는 혈관신생으로 인한 질환의 예방 또는 치료용 약학조성물
GB201204125D0 (en) 2012-03-08 2012-04-25 Karus Therapeutics Ltd Compounds
WO2014032019A2 (en) 2012-08-23 2014-02-27 Georgetown University Compounds and methods of use thereof for treating tumors
CA2889905A1 (en) 2012-11-08 2014-05-15 Rhizen Pharmaceuticals Sa Pharmaceutical compositions containing a pde4 inhibitor and a pi3 delta or dual pi3 delta-gamma kinase inhibitor
US9169214B2 (en) 2012-12-21 2015-10-27 The Board Of Trustees Of The Leland Stanford Junior University Compounds and compositions that bind and stabilize transthyretin and their use for inhibiting transthyretin amyloidosis and protein-protein interactions
US20160052926A1 (en) 2013-03-15 2016-02-25 Hutchison Medipharma Limited Novel pyrimidine and pyridine compounds and usage thereof
WO2014153280A1 (en) 2013-03-22 2014-09-25 Merck Sharp & Dohme Corp. 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors
NZ714283A (en) 2013-05-10 2020-04-24 Karus Therapeutics Ltd Novel histone deacetylase inhibitors
GB201402431D0 (en) 2014-02-12 2014-03-26 Karus Therapeutics Ltd Compounds
JP6556146B2 (ja) 2014-08-26 2019-08-07 武田薬品工業株式会社 複素環化合物
GB201419228D0 (en) 2014-10-29 2014-12-10 Karus Therapeutics Ltd Compounds
GB201419264D0 (en) 2014-10-29 2014-12-10 Karus Therapeutics Ltd Compounds
GB201609786D0 (en) 2016-06-03 2016-07-20 Karus Therapeutics Ltd Compounds and method of use
WO2017222952A1 (en) 2016-06-23 2017-12-28 Merck Sharp & Dohme Corp. 3- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histone deacetylase 6 (hdac6) inhibitors
EP3475275B1 (en) 2016-06-23 2024-04-10 Merck Sharp & Dohme LLC 3-aryl and heteroaryl substituted 5-trifluoromethyl oxadiazoles as histone deacetylase 6 (hdac6) inhibitors
WO2017222950A1 (en) 2016-06-23 2017-12-28 Merck Sharp & Dohme Corp. 3-heterocyclyl substituted 5-trifluoromethyl oxadiazoles as histone deacetylase 6 (hdac6) inhibitors

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55118472A (en) * 1979-03-03 1980-09-11 Hoechst Ag Triazole substituted hydroatropic acid derivative*its manufacture and plant protecting agent containing same
JPH0532662A (ja) * 1990-11-09 1993-02-09 Nissan Chem Ind Ltd 置換ピラゾール誘導体および農園芸用殺菌剤
WO1992022536A1 (de) * 1991-06-14 1992-12-23 Schering Aktiengesellschaft, Berlin Und Bergkamen Bicyclisch substituierte vinylimidazole, -triazole und -tetrazole
JPH07285953A (ja) * 1994-03-30 1995-10-31 F Hoffmann La Roche Ag 新規な、単環式又は二環式ｄｎａジャイレース阻害剤
WO2007085540A1 (en) * 2006-01-27 2007-08-02 Glaxo Group Limited 1h-indaz0l-4-yl-2 , 4-pyrimidinediamine derivatives
JP2010523601A (ja) * 2007-04-09 2010-07-15 メシルジーン インコーポレイテッド ヒストンデアセチラーゼ阻害剤
WO2009063240A1 (en) * 2007-11-16 2009-05-22 Arrow Therapeutics Limited 2,4-diaminopyrimidine derivatives useful as inhibitors of aurora kinase
JP2012516317A (ja) * 2009-01-28 2012-07-19 カルス セラピューティクス リミテッド スクリプタイドアイソスター（ｓｃｒｉｐｔａｉｄｉｓｏｓｔｅｒｅｓ）およびその治療における使用
WO2014072714A1 (en) * 2012-11-07 2014-05-15 Karus Therapeutics Ltd Novel histone deacetylase inhibitors and their use in therapy

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
BRUIJNINCX, P. C. A. ET AL., EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, JPN6019008882, 2005, pages 779 - 787, ISSN: 0003995134 *
ENRIQUE DIEZ-BARRA, TETRAHEDRON LETTERS, vol. V45 N37, JPN5015011267, 1 September 2004 (2004-09-01), pages 6937 - 6939, ISSN: 0003995137 *
MARIA, L. ET AL., DALTON TRANSACTIONS, JPN7019000736, 2007, pages 3010 - 3019, ISSN: 0003995138 *
MOELANDS, M. A. H. ET AL., INORGANIC CHEMISTRY, vol. 52, JPN6019008883, 2013, pages 7394 - 7410, ISSN: 0003995136 *
PETERS, L. ET AL: "Synthesis and transition metal complexes of 3,3-bis(1-vinylimidazol-2-yl)propionic acid, a new N,N,O", INORGANICA CHIMICA ACTA, vol. 374(1), JPN6017030249, 2011, pages 392 - 405, ISSN: 0003995135 *
PRASANNA, P. ET AL., GREEN CHEMISTRY, vol. 15, JPN7019000737, 2013, pages 1292 - 1299, ISSN: 0003995140 *
SAUDI, M. N. S. ET AL., LETTERS IN DRUG DESIGN & DISCOVERY, vol. 6, JPN6019008881, 2009, pages 268 - 277, ISSN: 0003995133 *
TARDITO, S. ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, JPN6019008884, 2011, pages 6235 - 6242, ISSN: 0003995139 *
XU, Z. ET AL., MOLECULAR DIVERSITY, vol. 16, JPN7019000738, 2012, pages 73 - 79, ISSN: 0003995141 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112237994A (zh) * 2020-09-21 2021-01-19 昆明冶金研究院有限公司 一种多金属硫化矿硫化锌高效抑制剂及其制备方法与应用

Also Published As

Publication number Publication date
SG11201703492RA (en) 2017-05-30
CA2966072A1 (en) 2016-05-06
MX2017005422A (es) 2017-08-24
AU2015340305A1 (en) 2017-05-18
IL251860A0 (en) 2017-06-29
CN107001340A (zh) 2017-08-01
GB201419228D0 (en) 2014-12-10
EP3212625A1 (en) 2017-09-06
US10407435B2 (en) 2019-09-10
WO2016067040A1 (en) 2016-05-06
KR20170081194A (ko) 2017-07-11
BR112017008794A2 (pt) 2017-12-26
AU2015340305B2 (en) 2018-12-06
US20170313712A1 (en) 2017-11-02

Similar Documents

Publication Publication Date Title
US11753404B2 (en) Aminothiazole compounds as c-Kit inhibitors
JP2017532357A (ja) ジヘテロアリールヒストンデアセチラーゼインヒビターおよび治療におけるその使用
US12257254B2 (en) Compositions comprising phosphoinositide 3-kinase inhibitors and a second antiproliferative agent
ES2673278T3 (es) Compuestos heterocíclicos tricíclicos como inhibidores de la fosfoinositol 3-cinasa
EP3456355A1 (en) Compositions comprising a pi3k inhibitor and an hdac inhibitor
US10150763B2 (en) Histone deacetylase inhibitors and their use in therapy
US10533003B2 (en) Polyheteroarl histone deacetylase inhibitors and their use in therapy
NZ795496A (en) Aminothiazole compounds as c-Kit inhibitors
HK1251467B (en) Compositions comprising phosphoinositide 3-kinase inhibitors and a second antiproliferative agent

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180718

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20180718

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20190228

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20190312

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190611

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190807

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190912

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20200129