WO2010043866A3 - Histone lysine demethylase inhibitors - Google Patents

Histone lysine demethylase inhibitors Download PDF

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Publication number
WO2010043866A3
WO2010043866A3 PCT/GB2009/002465 GB2009002465W WO2010043866A3 WO 2010043866 A3 WO2010043866 A3 WO 2010043866A3 GB 2009002465 W GB2009002465 W GB 2009002465W WO 2010043866 A3 WO2010043866 A3 WO 2010043866A3
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WO
WIPO (PCT)
Prior art keywords
inhibitors
derivative
formula
histone lysine
activation
Prior art date
Application number
PCT/GB2009/002465
Other languages
French (fr)
Other versions
WO2010043866A2 (en
Inventor
Christopher Joseph Schofield
Michael Mcdonough
Nathan Rose
Armin Thalhammer
Original Assignee
Isis Innovation Limited
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Filing date
Publication date
Application filed by Isis Innovation Limited filed Critical Isis Innovation Limited
Publication of WO2010043866A2 publication Critical patent/WO2010043866A2/en
Publication of WO2010043866A3 publication Critical patent/WO2010043866A3/en

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    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • 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
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/56—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention provides a compound which is an iV-oxalylglycine derivative of formula (I): a hydroxamic acid derivative of formula (II): or a heteroaryl derivative of fomula (III): wherein n; Z1; Z2; Y1; Y2; A; p; X1; X2; m; R4; B; R5; R6; R7; R8; R9; X3; R10; R11 and R12 are as defined herein, or a pharmaceutically acceptable salt thereof. These compounds are inhibitors of the human 2-oxoglutarate-dependant JMJD2 subfamily of histone demethylases, in particular JMJD2E. Such inhibitors are useful in changing the epigenetic state of cells resulting in the inhibition / activation of chromatin remodelling, multiple gene activation / deactivation, and in treating cancer and other conditions characterised by undesirable cellular proliferation, and psychiatric disorders including depression.
PCT/GB2009/002465 2008-10-15 2009-10-15 Histone lysine demethylase inhibitors WO2010043866A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0818907.8 2008-10-15
GBGB0818907.8A GB0818907D0 (en) 2008-10-15 2008-10-15 Histone lysine demethylase inhibitors

Publications (2)

Publication Number Publication Date
WO2010043866A2 WO2010043866A2 (en) 2010-04-22
WO2010043866A3 true WO2010043866A3 (en) 2010-10-07

Family

ID=40084077

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2009/002465 WO2010043866A2 (en) 2008-10-15 2009-10-15 Histone lysine demethylase inhibitors

Country Status (2)

Country Link
GB (1) GB0818907D0 (en)
WO (1) WO2010043866A2 (en)

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WO2010051188A1 (en) * 2008-10-31 2010-05-06 Merck Sharp & Dohme Corp. P2x3, receptor antagonists for treatment of pain
GB0918862D0 (en) * 2009-10-27 2009-12-09 Glaxo Group Ltd Method of treatment
WO2012007007A1 (en) * 2010-07-15 2012-01-19 Epitherapeutics Aps Inhibitors of hdme
WO2012012627A1 (en) * 2010-07-22 2012-01-26 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Method of preventing or treating viral infection
GB201112607D0 (en) * 2011-07-22 2011-09-07 Glaxo Group Ltd Novel compounds
TWI429637B (en) * 2011-04-01 2014-03-11 Nat Univ Tsing Hua Tridentate ligand deriving from 4,4'-dicarboxy-2,2'-bipyridine basic unit, metal complex and applications thereof
WO2012150042A1 (en) 2011-05-04 2012-11-08 Cellzome Ag Compounds and methods for the identification of histone demethylase interacting molecules and for the purification of histone demethylase proteins
EP2592154A1 (en) 2011-11-09 2013-05-15 Cellzome Ag Immobilization products and methods for the identification of histone demethylase interacting molecules and for the purification of histone demethylase proteins
WO2013143597A1 (en) 2012-03-29 2013-10-03 Glaxo Group Limited Demethylase enzymes inhibitors
ES2834959T3 (en) 2012-12-06 2021-06-21 Celgene Quanticel Res Inc Histone demethylase inhibitors
CA2903081A1 (en) * 2013-03-14 2014-09-25 Quanticel Pharmaceuticals, Inc. Histone demethylase inhibitors
CN109574865A (en) * 2013-08-30 2019-04-05 英属哥伦比亚大学 Monoamine oxidase-B selective depression immunomodulator compounds, its pharmaceutical composition and application
CN105566145A (en) * 2014-11-03 2016-05-11 广州德汇行医药科技有限公司 Amino acid derivative and application thereof
WO2016210292A1 (en) 2015-06-25 2016-12-29 Children's Medical Center Corporation Methods and compositions relating to hematopoietic stem cell expansion, enrichment, and maintenance
EP4049665A1 (en) 2016-03-15 2022-08-31 Children's Medical Center Corporation Methods and compositions relating to hematopoietic stem cell expansion
WO2017207813A1 (en) 2016-06-03 2017-12-07 Oryzon Genomics, S.A. Heteroaryl-carboxylic acids as histone demethylase inhibitors
EP3579834A4 (en) * 2017-02-10 2021-04-28 Temple Otorongo LLC Treatment of diabetes and associated metabolic conditions with epigenetic modulators
WO2018149986A1 (en) * 2017-02-16 2018-08-23 Oryzon Genomics, S.A. 2-(bicyclo-heteroaryl)-isonicotinic derivatives as histone demethylase inhibitors
WO2018219478A1 (en) 2017-06-02 2018-12-06 Oryzon Genomics, S.A. Heteroaryl-carboxamides as histone demethylase inhibitors
CN107540574B (en) * 2017-09-19 2021-06-11 成都西岭源药业有限公司 Preparation method of R-biphenylalaninol
US20210254006A1 (en) 2018-06-06 2021-08-19 Ideaya Biosciences, Inc. Methods of culturing and/or expanding stem cells and/or lineage committed progenitor cells using lactam compounds
CN109438339A (en) * 2018-12-22 2019-03-08 山东大学 RBP2 enzyme inhibitor small molecule compound WXSA-072A and preparation method thereof and anti-gastric cancer application
CN109456262A (en) * 2018-12-22 2019-03-12 山东大学 Based on inhibition of histone demethylation enzyme compound and preparation method thereof and anti-gastric cancer application
CN114409557B (en) * 2022-01-19 2022-08-30 中南民族大学 Carbon keratin with neuroprotective activity and preparation method and application thereof

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Patent Citations (14)

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WO2010043866A2 (en) 2010-04-22
GB0818907D0 (en) 2008-11-19

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