CA2915817C - Substituted (e)-n'-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors - Google Patents

Substituted (e)-n'-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors Download PDF

Info

Publication number
CA2915817C
CA2915817C CA2915817A CA2915817A CA2915817C CA 2915817 C CA2915817 C CA 2915817C CA 2915817 A CA2915817 A CA 2915817A CA 2915817 A CA2915817 A CA 2915817A CA 2915817 C CA2915817 C CA 2915817C
Authority
CA
Canada
Prior art keywords
compound
further aspect
mmol
mao
compounds
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
CA2915817A
Other languages
English (en)
French (fr)
Other versions
CA2915817A1 (en
Inventor
Hariprasad Vankayalapati
Venkataswamy SORNA
Steve L. Warner
David J. Bearss
Sunil Sharma
Bret STEPHENS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Utah Research Foundation Inc
Original Assignee
University of Utah Research Foundation Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US13/921,895 external-priority patent/US9266838B2/en
Application filed by University of Utah Research Foundation Inc filed Critical University of Utah Research Foundation Inc
Publication of CA2915817A1 publication Critical patent/CA2915817A1/en
Application granted granted Critical
Publication of CA2915817C publication Critical patent/CA2915817C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26Sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96Sulfur atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86Hydrazides; Thio or imino analogues thereof
    • C07D213/87Hydrazides; Thio or imino analogues thereof in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2915817A 2013-06-19 2014-06-19 Substituted (e)-n'-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors Active CA2915817C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13/921,895 2013-06-19
US13/921,895 US9266838B2 (en) 2011-08-15 2013-06-19 Substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors
PCT/US2014/043179 WO2014205213A1 (en) 2013-06-19 2014-06-19 Substituted (e)-n'-(1-phenylethylidene) benzohydrazide analogs as histone demethylase inhibitors

Publications (2)

Publication Number Publication Date
CA2915817A1 CA2915817A1 (en) 2014-12-24
CA2915817C true CA2915817C (en) 2022-12-13

Family

ID=52105283

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2915817A Active CA2915817C (en) 2013-06-19 2014-06-19 Substituted (e)-n'-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors

Country Status (13)

Country Link
EP (1) EP3010915B1 (enExample)
JP (1) JP6525162B2 (enExample)
KR (1) KR102288648B1 (enExample)
CN (2) CN105555784B (enExample)
AU (1) AU2014281398B2 (enExample)
BR (1) BR112015032113B1 (enExample)
CA (1) CA2915817C (enExample)
ES (1) ES2739814T3 (enExample)
IL (1) IL243200B (enExample)
MX (1) MX366949B (enExample)
NZ (1) NZ715331A (enExample)
SG (2) SG11201510376QA (enExample)
WO (1) WO2014205213A1 (enExample)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2014281398B2 (en) * 2013-06-19 2018-10-04 University Of Utah Research Foundation Substituted (E)-N'-(1-phenylethylidene) benzohydrazide analogs as histone demethylase inhibitors
PT3105218T (pt) 2014-02-13 2019-12-05 Incyte Corp Ciclopropilaminas como inibidores de lsd1
US9527835B2 (en) 2014-02-13 2016-12-27 Incyte Corporation Cyclopropylamines as LSD1 inhibitors
DK3105226T3 (da) 2014-02-13 2019-10-14 Incyte Corp Cyclopropylaminer som lsd1-inhibitorer
EP3105219B9 (en) 2014-02-13 2018-10-03 Incyte Corporation Cyclopropylamines as lsd1 inhibitors
TW201613925A (en) 2014-07-10 2016-04-16 Incyte Corp Imidazopyrazines as LSD1 inhibitors
US9758523B2 (en) 2014-07-10 2017-09-12 Incyte Corporation Triazolopyridines and triazolopyrazines as LSD1 inhibitors
WO2016007722A1 (en) 2014-07-10 2016-01-14 Incyte Corporation Triazolopyridines and triazolopyrazines as lsd1 inhibitors
TWI687419B (zh) 2014-07-10 2020-03-11 美商英塞特公司 作為lsd1抑制劑之咪唑并吡啶及咪唑并吡嗪
WO2016119031A1 (pt) * 2015-01-29 2016-08-04 Fundação De Amparo À Pesquisa Do Estado De Minas Gerais - Fapemig Composto, processo de síntese do composto, uso, composição farmacêutica, método de tratamento de inflamações ou de doença neurodegenerativa, forma de dosagem oral e método de inibição de enzima acetilcolinesterase
EP3626720A1 (en) 2015-04-03 2020-03-25 Incyte Corporation Heterocyclic compounds as lsd1 inhibitors
EP3307909A1 (en) 2015-06-12 2018-04-18 Oryzon Genomics, S.A. Biomarkers associated with lsd1 inhibitors and uses thereof
WO2017013061A1 (en) 2015-07-17 2017-01-26 Oryzon Genomics, S.A. Biomarkers associated with lsd1 inhibitors and uses thereof
KR102710120B1 (ko) 2015-08-12 2024-09-27 인사이트 홀딩스 코포레이션 Lsd1 저해제의 염
JP2019500394A (ja) 2015-12-30 2019-01-10 ノバルティス アーゲー 有効性が増強された免疫エフェクター細胞治療
SG11201807965YA (en) 2016-03-15 2018-10-30 Oryzon Genomics Sa Combinations of lsd1 inhibitors for use in the treatment of solid tumors
ES3042059T3 (en) 2016-03-16 2025-11-18 Oryzon Genomics Sa Methods to determine kdm1a target engagement and chemoprobes useful therefor
PE20190377A1 (es) 2016-04-22 2019-03-08 Incyte Corp Formulaciones de un inhibidor de lsd 1
EP3535420A1 (en) 2016-11-03 2019-09-11 Oryzon Genomics, S.A. Biomarkers for determining responsiveness to lsd1 inhibitors
WO2018083138A1 (en) 2016-11-03 2018-05-11 Oryzon Genomics, S.A. Pharmacodynamic biomarkers for personalized cancer care using epigenetic modifying agents
CN108727377A (zh) * 2017-04-14 2018-11-02 四川大学 3-氰基吡唑并[1,5-a]嘧啶衍生物及其制备方法和用途
DK3661510T3 (da) 2017-08-03 2025-01-02 Oryzon Genomics Sa Fremgangsmåder til behandling af adfærdsændringer
WO2019068326A1 (en) 2017-10-05 2019-04-11 Université D'aix-Marseille INHIBITORS OF LSD1 FOR THE TREATMENT AND PREVENTION OF CARDIOMYOPATHIES
CN108689960B (zh) * 2018-06-07 2022-03-04 济南大学 5-苯亚甲基-2-苯基噻唑酮类化合物及其制备和应用
US10968200B2 (en) 2018-08-31 2021-04-06 Incyte Corporation Salts of an LSD1 inhibitor and processes for preparing the same
SG11202109159VA (en) 2019-03-20 2021-10-28 Oryzon Genomics Sa Methods of treating borderline personality disorder
JP7535797B2 (ja) 2019-03-20 2024-08-19 オリソン ヘノミクス,ソシエダ アノニマ 化合物バフィデムスタット(vafidemstat)などkdm1a阻害剤を使用した注意欠陥多動性障害の処置方法
JP2022546908A (ja) 2019-07-05 2022-11-10 オリゾン・ゲノミクス・ソシエダッド・アノニマ Kdm1a阻害剤を使用した小細胞肺がんの個別化された処置のためのバイオマーカーおよび方法
CN111426850B (zh) * 2020-01-15 2021-12-21 上海众启生物科技有限公司 用于阿尔茨海默症自身抗体检测的含dnajc8蛋白片段的组合物
EP3964204A1 (en) 2020-09-08 2022-03-09 Université d'Aix-Marseille Lsd1 inhibitors for use in the treatment and prevention of fibrosis of tissues
CA3231846A1 (en) 2021-04-08 2022-10-13 Tamara Maes Combinations of lsd1 inhibitors for treating myeloid cancers
CN119497613A (zh) 2022-05-09 2025-02-21 奥莱松基因组股份有限公司 使用lsd1抑制剂治疗nf1-突变肿瘤的方法
JP2025516647A (ja) 2022-05-09 2025-05-30 オリゾン・ゲノミクス・ソシエダッド・アノニマ Lsd1阻害薬を用いる悪性末梢神経鞘腫(mpnst)の治療法
WO2024110649A1 (en) 2022-11-24 2024-05-30 Oryzon Genomics, S.A. Combinations of lsd1 inhibitors and menin inhibitors for treating cancer
CN116444437B (zh) * 2023-03-08 2025-09-16 曲靖师范学院 抗癌医药达洛鲁胺的合成方法
CN116813569B (zh) * 2023-07-10 2024-07-02 衡阳市中心医院 一种抗癌药中间体的制备方法和抗癌药的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE602005022113D1 (de) * 2005-01-07 2010-08-12 Hoffmann La Roche Phenyl)methanon-derivate als glycin-transporter 1 (glyt-1) hemmer zur behandlung von neurologischen und neuropsychiatrischen erkrankungen
WO2006136008A1 (en) * 2005-05-24 2006-12-28 University Health Network Salicylic acid hydrazones as inhibitors of the erk mapkinase pathway and for the treatment of cancer
US20080214495A1 (en) * 2005-07-08 2008-09-04 Astrazeneca Ab Heterocyclic Sulfonamide Derivatives as Inhibitors of Factor Xa
WO2010083318A2 (en) * 2009-01-14 2010-07-22 Dow Agrosciences Llc Fungicidal compositions including hydrazone derivatives and copper
US9051296B2 (en) * 2009-11-16 2015-06-09 Raqualia Pharma Inc. Aryl carboxamide derivatives as TTX-S blockers
US20110189306A1 (en) * 2010-01-13 2011-08-04 Norbert Kartner COMPOUNDS, COMPOSITIONS AND TREATMENTS FOR V-ATPase RELATED DISEASES
WO2012062704A1 (en) * 2010-11-09 2012-05-18 Cellzome Limited Pyridine compounds and aza analogues thereof as tyk2 inhibitors
BR112014003382B1 (pt) * 2011-08-15 2022-03-15 University Of Utah Research Foundation Análogos de (e)-n-(1-feniletilideno) benzo-hidrazida substituída como inibidores de histona desmetilase e composições farmacêuticas compreendendo-os
AU2014281398B2 (en) * 2013-06-19 2018-10-04 University Of Utah Research Foundation Substituted (E)-N'-(1-phenylethylidene) benzohydrazide analogs as histone demethylase inhibitors

Also Published As

Publication number Publication date
CN110015984A (zh) 2019-07-16
ES2739814T3 (es) 2020-02-04
BR112015032113A2 (pt) 2017-03-21
CA2915817A1 (en) 2014-12-24
CN105555784A (zh) 2016-05-04
AU2014281398B2 (en) 2018-10-04
IL243200A0 (en) 2016-02-29
JP6525162B2 (ja) 2019-06-05
JP2016523256A (ja) 2016-08-08
BR112015032113B1 (pt) 2019-01-29
SG10201710543PA (en) 2018-02-27
IL243200B (en) 2020-10-29
MX366949B (es) 2019-07-30
EP3010915B1 (en) 2019-05-08
SG11201510376QA (en) 2016-01-28
EP3010915A1 (en) 2016-04-27
WO2014205213A1 (en) 2014-12-24
KR20160024929A (ko) 2016-03-07
AU2014281398A1 (en) 2016-01-21
NZ715331A (en) 2019-09-27
CN105555784B (zh) 2019-03-15
EP3010915A4 (en) 2016-12-28
KR102288648B1 (ko) 2021-08-12
MX2015018032A (es) 2016-10-03

Similar Documents

Publication Publication Date Title
CA2915817C (en) Substituted (e)-n'-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors
CA2843609C (en) Substituted (e)-n'-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors
US20170001970A1 (en) Substituted benzohydrazide analogs as histone demethylase inhibitors
US9642857B2 (en) Substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors
CA3106860C (en) 1-methyl-4-[(4-phenylphenyl)sulfonylmethyl]cyclohexanol and 1-methyl-4-[[4-(2-pyridyl)phenyl]sulfonylmethyl]cyclohexanol compounds and their therapeutic use
EP3956030B1 (en) N-acyl-{4-[(4-aryl-phenyl)sulfonylmethyl]piperidine} compounds and their therapeutic use
WO2020190912A1 (en) Quinoline and quinazoline compounds and methods of use thereof
NZ621078B2 (en) Substituted (e)-n'-(1-phenylethylidene) benzohydrazide analogs as histone demethylase inhibitors

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190401

EEER Examination request

Effective date: 20190401

EEER Examination request

Effective date: 20190401

EEER Examination request

Effective date: 20190401

EEER Examination request

Effective date: 20190401

EEER Examination request

Effective date: 20190401

EEER Examination request

Effective date: 20190401