CA2931313C - Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform - Google Patents

Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform Download PDF

Info

Publication number
CA2931313C
CA2931313C CA2931313A CA2931313A CA2931313C CA 2931313 C CA2931313 C CA 2931313C CA 2931313 A CA2931313 A CA 2931313A CA 2931313 A CA2931313 A CA 2931313A CA 2931313 C CA2931313 C CA 2931313C
Authority
CA
Canada
Prior art keywords
compounds
compound
era
agonist
formula
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
CA2931313A
Other languages
English (en)
French (fr)
Other versions
CA2931313A1 (en
Inventor
William A. DONALDSON
Daniel S. Sem
Terrence S. NEUMANN
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.)
Marquette University
Concordia University
Original Assignee
Marquette University
Concordia University
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 Marquette University, Concordia University filed Critical Marquette University
Publication of CA2931313A1 publication Critical patent/CA2931313A1/en
Application granted granted Critical
Publication of CA2931313C publication Critical patent/CA2931313C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30—Oestrogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Psychiatry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2931313A 2013-11-21 2014-11-21 Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform Active CA2931313C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361963031P 2013-11-21 2013-11-21
US61/963,031 2013-11-21
PCT/US2014/066896 WO2015077611A1 (en) 2013-11-21 2014-11-21 Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform

Publications (2)

Publication Number Publication Date
CA2931313A1 CA2931313A1 (en) 2015-05-28
CA2931313C true CA2931313C (en) 2022-04-05

Family

ID=53180206

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2931313A Active CA2931313C (en) 2013-11-21 2014-11-21 Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform

Country Status (6)

Country Link
US (1) US10570077B2 (enExample)
EP (1) EP3071541B1 (enExample)
JP (1) JP6431538B2 (enExample)
AU (1) AU2014352830B2 (enExample)
CA (1) CA2931313C (enExample)
WO (1) WO2015077611A1 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018183800A1 (en) * 2017-03-30 2018-10-04 Marquette University Substituted (4'-hydroxyphenyl)cycloalkane and (4'-hydroxyphenyl)cycloalkene compounds and uses thereof as selective agonists of the estrogen receptor beta isoform for enhanced memory consolidation
CN112341320A (zh) * 2020-11-02 2021-02-09 烟台丰鲁精细化工有限责任公司 一种对（反式-4-羟基环己基）酚的新型合成方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1086530A (en) 1965-08-04 1967-10-11 Du Pont 4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-amines
US3564060A (en) 1967-12-08 1971-02-16 Du Pont Pharmaceutically active derivatives of 4 - phenyl - bicyclo (2,2,2)octane and oct-2-ene-1-carbinols and carboxaldehydes
DE4035961A1 (de) 1990-11-02 1992-05-07 Thomae Gmbh Dr K Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
US6288050B1 (en) 1997-07-18 2001-09-11 Duquesne University Of The Holy Ghost Steroid sulfatase inhibitors and methods for making and using the same
GB9810862D0 (en) 1998-05-20 1998-07-22 Hoechst Schering Agrevo Gmbh Substitutedn pyridine and pyrimidines, processes for their preparation and their use as pesticides
MXPA02009659A (es) 2000-04-26 2003-03-10 Warner Lambert Co Derivado de ciclohexilamina como subtipo de los antagonistas del receptor selectivo nmda.
AR069802A1 (es) * 2007-12-20 2010-02-17 Astrazeneca Ab Compuestos de carbamoilo como inhibidores de dgat1 190
RS54165B1 (sr) * 2008-04-16 2015-12-31 Karo Bio Ab Novi ligandi za estrogenski receptor
EA201170983A1 (ru) * 2009-01-28 2012-03-30 Санофи Производные тиадиазолов и оксадиазолов, их получение и их применение в терапии
US9242948B2 (en) 2009-09-03 2016-01-26 Sumitomo Chemical Company, Limited Diepoxy compound, process for producing same, and composition containing the diepoxy compound
WO2012112364A1 (en) 2011-02-14 2012-08-23 Merck Sharp & Dohme Corp. Lactam derivatives as dgat-1 inhibitors
US9271969B2 (en) * 2012-02-07 2016-03-01 Kainos Medicine, Inc. Compounds as inhibitors of diacylglycerol O-acyltransferase type 1 enzyme

Also Published As

Publication number Publication date
AU2014352830B2 (en) 2018-12-13
CA2931313A1 (en) 2015-05-28
WO2015077611A1 (en) 2015-05-28
US10570077B2 (en) 2020-02-25
JP2017504567A (ja) 2017-02-09
AU2014352830A1 (en) 2016-07-07
EP3071541A1 (en) 2016-09-28
US20160340279A1 (en) 2016-11-24
JP6431538B2 (ja) 2018-11-28
EP3071541A4 (en) 2017-07-19
EP3071541B1 (en) 2023-06-07

Similar Documents

Publication Publication Date Title
JP5203712B2 (ja) 選択的アンドロゲン受容体モジュレータとしてのアミノフェニル誘導体
JP6920295B2 (ja) テトラヒドロナフタレンエストロゲン受容体モジュレーター及びその使用
TWI357904B (en) Antagonists of the vanilloid receptor subtype 1 (v
NO317978B1 (no) Anti-ostrogeniske steroider og farmasoytisk preparat inneholdende samme, samt anvendelse derav
Feng et al. Design, synthesis and biological evaluation of novel potent STAT3 inhibitors based on BBI608 for cancer therapy
JP2013501006A (ja) 認知機能低下の阻害剤
Schmidt et al. De novo design, synthesis, and evaluation of novel nonsteroidal phenanthrene ligands for the estrogen receptor
JP2025081398A (ja) 置換（４’－ヒドロキシフェニル）シクロアルカンおよび（４’－ヒドロキシフェニル）シクロアルケン化合物ならびに記憶固定を向上させるためのエストロゲン受容体βアイソフォームの選択的アゴニストとしてのそれらの使用方法
EP3071541B1 (en) Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform
Collina et al. Design, synthesis, and SAR analysis of novel selective σ1 ligands
JP4381810B2 (ja) 選択的エストロゲン受容体βアゴニストとしての置換ベンゾピラン
JP2014511373A (ja) ウコン油から単離された化合物およびその使用方法
Gitto et al. Development of 3-substituted-1H-indole derivatives as NR2B/NMDA receptor antagonists
McCullough et al. Probing the human estrogen receptor-α binding requirements for phenolic mono-and di-hydroxyl compounds: A combined synthesis, binding and docking study
JP2000136173A (ja) シクロアルキレン鎖を有する新規環式化合物、その製造法、及びそれを含有する製剤組成物
JP2010529080A (ja) 皮質カテコールアミン作動性神経伝達の調節因子としての新規な二置換フェニルピロリジン
JP2011512414A5 (enExample)
US20240351965A1 (en) Synthesis and Evaluation of Novel (4-Hydroxyphenyl) Substituted Carbocycles as Potent and Selective Estrogen Receptor Beta Agonists
WO2002058639A2 (en) Pyranoflavonoid compounds and their use as estrogen receptor modulators
DeLeon Novel G Protein-Coupled Estrogen Receptor (GPER) Specific Ligands as Probes in Deciphering the Complex Pharmacology Associated with Estrogen Signaling
KR101634758B1 (ko) 에스트로겐 수용체 리간드로서의 2-하이드록시-7-메틸 옥타하이드로페난트렌 유도체 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 약학 조성물
Dixon Part I: the synthesis of C3 heteroadamantyl cannabinoids Part II: the synthesis of C3 heteroaroyl cannabinoids
Lu Novel cannabinergic agents and molecular probes
HK1106514A (en) Novel chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors
JP2010535175A (ja) Ｎ−アリール−ｎ−ピペリジン−４−イルメチルアミド誘導体及びモノアミン神経伝達物質再取り込み阻害薬としてのその使用

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20191114