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DK3231793T3 - Dihydropyromidin-2-on-forbindelser og medicinske anvendelser deraf - Google Patents

Dihydropyromidin-2-on-forbindelser og medicinske anvendelser deraf Download PDF

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Publication number
DK3231793T3
DK3231793T3 DK15866802.0T DK15866802T DK3231793T3 DK 3231793 T3 DK3231793 T3 DK 3231793T3 DK 15866802 T DK15866802 T DK 15866802T DK 3231793 T3 DK3231793 T3 DK 3231793T3
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Denmark
Prior art keywords
dihydropyromidin
compounds
medical applications
medical
applications
Prior art date
Application number
DK15866802.0T
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English (en)
Inventor
Masahiro Yokota
Taku Ikenogami
Eiichi Watanabe
Noriyoshi Seki
Takayuki Sakai
Shingo Fujioka
Makoto Shiozaki
Katsunori Suwa
Yosuke Ogoshi
Masato Noguchi
Katsuya Maeda
Original Assignee
Japan Tobacco Inc
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Publication of DK3231793T3 publication Critical patent/DK3231793T3/da

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    • 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
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • 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
    • A61K31/695—Silicon compounds
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
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    • 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
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    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
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    • 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
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P37/00—Drugs for immunological or allergic disorders
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
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    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • 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
    • C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • 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
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • C07D405/10—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 linked by a carbon chain containing aromatic 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Dermatology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Transplantation (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
DK15866802.0T 2014-12-12 2015-12-11 Dihydropyromidin-2-on-forbindelser og medicinske anvendelser deraf DK3231793T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014251771 2014-12-12
PCT/JP2015/084791 WO2016093342A1 (ja) 2014-12-12 2015-12-11 ジヒドロピリミジン－２－オン化合物およびその医薬用途

Publications (1)

Publication Number Publication Date
DK3231793T3 true DK3231793T3 (da) 2020-05-11

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ID=56107519

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DK15866802.0T DK3231793T3 (da) 2014-12-12 2015-12-11 Dihydropyromidin-2-on-forbindelser og medicinske anvendelser deraf

Country Status (33)

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US (4) US10196363B2 (da)
EP (2) EP3231793B1 (da)
JP (4) JP6757565B2 (da)
KR (1) KR102551018B1 (da)
CN (1) CN107001286B (da)
AR (1) AR102972A1 (da)
AU (1) AU2015362394C1 (da)
BR (1) BR112017010471B1 (da)
CA (1) CA2965804C (da)
CL (1) CL2017001467A1 (da)
CO (1) CO2017005732A2 (da)
CY (1) CY1122971T1 (da)
DK (1) DK3231793T3 (da)
ES (1) ES2787700T3 (da)
HR (1) HRP20200584T1 (da)
HU (1) HUE048503T2 (da)
IL (2) IL251940B (da)
LT (1) LT3231793T (da)
ME (1) ME03760B (da)
MX (1) MX371128B (da)
MY (1) MY193671A (da)
PE (1) PE20171119A1 (da)
PH (1) PH12017501071A1 (da)
PL (1) PL3231793T3 (da)
PT (1) PT3231793T (da)
RS (1) RS60352B1 (da)
RU (1) RU2770061C2 (da)
SA (1) SA517381678B1 (da)
SG (2) SG11201703885TA (da)
SI (1) SI3231793T1 (da)
TW (2) TWI739206B (da)
WO (1) WO2016093342A1 (da)
ZA (1) ZA201703976B (da)

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Publication number Priority date Publication date Assignee Title
EP3231793B1 (en) * 2014-12-12 2020-03-11 Japan Tobacco Inc. Dihydropyrimidine-2-one compounds and medicinal uses thereof
CN106496008A (zh) * 2016-10-20 2017-03-15 上海毕得医药科技有限公司 一种合成4‑(4‑氯苯基)环己酮的方法
WO2019167981A1 (ja) * 2018-02-28 2019-09-06 日本たばこ産業株式会社 ４－メチルジヒドロピリミジノン化合物及びその医薬用途
JP7200005B2 (ja) * 2018-02-28 2023-01-06 日本たばこ産業株式会社 飽和環縮合ジヒドロピリミジノン又はジヒドロトリアジノン化合物及びその医薬用途
CN110294762B (zh) * 2019-06-14 2020-12-15 深圳市疾病预防控制中心（深圳市卫生检验中心、深圳市预防医学研究所） 检测米酵菌酸中毒的人工抗原及应用
WO2021149786A1 (en) 2020-01-24 2021-07-29 Japan Tobacco Inc. Methods of treating cancer using dihydropyrimidin-2-one compounds
WO2023232870A1 (en) 2022-05-31 2023-12-07 Immunic Ag Rorg/rorgt modulators for the treatment of virus infections like covid-19

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US4485107A (en) * 1982-11-01 1984-11-27 Janssen Pharmaceutica N.V. [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones
CN101384261B (zh) * 2005-12-22 2011-12-07 海德拉生物科学公司 治疗疼痛的组合物
DE102006031314A1 (de) * 2006-07-01 2008-01-03 Bayer Healthcare Aktiengesellschaft Verwendung von 1,4-Diaryl-dihydropyrimidin-2-on-Derivaten zur Behandlung der pulmonalen arteriellen Hyptertonie
BRPI0814999A2 (pt) 2007-08-09 2015-02-03 Hoffmann La Roche Derivados de bezoil-piperidina como moduladores duais dos receptores 5-ht2a e d3
US20110201634A1 (en) * 2008-06-13 2011-08-18 Delhi University Dihydropyridimidinone compounds for the treatment of cardiovascular diseases and process for preparing the same
AR086156A1 (es) 2011-04-28 2013-11-20 Japan Tobacco Inc Compuesto de amida y su uso medicinal
EP2682389A1 (en) 2012-07-02 2014-01-08 Commissariat A L'energie Atomique Et Aux Energies Alternatives Dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones as inhibitors of sodium iodide symporter
WO2014062938A1 (en) * 2012-10-19 2014-04-24 Bristol-Myers Squibb Company Rory modulators
US20160137639A1 (en) 2012-10-26 2016-05-19 Japan Tobacco Inc. Triazole-isoxazole compound and medical use thereof
CN103113308B (zh) * 2013-01-25 2014-11-19 浙江大学 一种制备二氢嘧啶酮衍生物的方法
MA41148A (fr) 2014-12-12 2017-10-17 H Lundbeck As Procédé de fabrication d'idalopirdine
EP3231793B1 (en) * 2014-12-12 2020-03-11 Japan Tobacco Inc. Dihydropyrimidine-2-one compounds and medicinal uses thereof
WO2016091997A1 (en) 2014-12-12 2016-06-16 H. Lundbeck A/S A process for the manufacture of idalopirdine
MX2017007372A (es) 2014-12-12 2017-11-06 Merck Patent Gmbh Combinacion de un derivado de 6-oxo-1,6-dihidro-piridazina que tiene actividad anti-cancer con un inhibidor de factor de crecimiento epidermico (egfr).
CA2970500C (en) 2014-12-12 2023-08-29 Acetylon Pharmaceuticals, Inc. Piperidine derivatives as hdac1/2 inhibitors

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EP3231793A4 (en) 2018-09-19
KR20170090497A (ko) 2017-08-07
WO2016093342A1 (ja) 2016-06-16
MX2017007577A (es) 2017-09-28
PL3231793T3 (pl) 2020-07-27
US20210130300A1 (en) 2021-05-06
AR102972A1 (es) 2017-04-05
EP3744713A1 (en) 2020-12-02
RU2017124423A (ru) 2019-01-15
US20190359575A1 (en) 2019-11-28
SA517381678B1 (ar) 2021-12-14
ME03760B (me) 2021-04-20
AU2015362394C1 (en) 2021-01-28
BR112017010471B1 (pt) 2024-02-27
US20160194290A1 (en) 2016-07-07
TW202012377A (zh) 2020-04-01
KR102551018B1 (ko) 2023-07-05
US20230373932A1 (en) 2023-11-23
TWI690515B (zh) 2020-04-11
HUE048503T2 (hu) 2020-07-28
CY1122971T1 (el) 2021-10-29
RU2017124423A3 (da) 2019-08-13
CN107001286A (zh) 2017-08-01
SI3231793T1 (sl) 2020-07-31
EP3231793B1 (en) 2020-03-11
PE20171119A1 (es) 2017-08-08
HRP20200584T1 (hr) 2020-07-10
ZA201703976B (en) 2019-06-26
TW201639820A (zh) 2016-11-16
JP2022116239A (ja) 2022-08-09
IL283335B (en) 2022-04-01
JP2016113455A (ja) 2016-06-23
AU2015362394B2 (en) 2020-07-02
EP3231793A1 (en) 2017-10-18
PH12017501071A1 (en) 2017-12-18
CN107001286B (zh) 2020-07-07
IL283335A (en) 2021-07-29
TWI739206B (zh) 2021-09-11
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CL2017001467A1 (es) 2018-01-05
JP6757565B2 (ja) 2020-09-23
AU2015362394A1 (en) 2017-05-25
RS60352B1 (sr) 2020-07-31
CA2965804A1 (en) 2016-06-16
JP2024133646A (ja) 2024-10-02
BR112017010471A2 (pt) 2017-12-26
IL251940B (en) 2021-06-30
US10196363B2 (en) 2019-02-05
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