CA2970574C - Bicycloheteroaryl-heteroaryl-benzoic acid compounds as retinoic acid receptor beta (rar.beta.) agonists - Google Patents

Bicycloheteroaryl-heteroaryl-benzoic acid compounds as retinoic acid receptor beta (rar.beta.) agonists Download PDF

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Publication number
CA2970574C
CA2970574C CA2970574A CA2970574A CA2970574C CA 2970574 C CA2970574 C CA 2970574C CA 2970574 A CA2970574 A CA 2970574A CA 2970574 A CA2970574 A CA 2970574A CA 2970574 C CA2970574 C CA 2970574C
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bhba
compound according
neuropathy
independently
injury
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English (en)
French (fr)
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CA2970574A1 (en
Inventor
Alan David Borthwick
Mark Trevor MILLS
Jane Theresa Brown
Jonathan Patrick Thomas Corcoran
Maria Beatriz DE CASTRO VASCONCELOS GONCALVES
Sarkis Barret Kalindjian
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Kings College London
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Kings College London
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4245Oxadiazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10Drugs for genital or sexual disorders; Contraceptives for impotence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Psychology (AREA)
  • Epidemiology (AREA)
  • Reproductive Health (AREA)
  • Gynecology & Obstetrics (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2970574A 2014-12-17 2015-12-16 Bicycloheteroaryl-heteroaryl-benzoic acid compounds as retinoic acid receptor beta (rar.beta.) agonists Active CA2970574C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB201422472 2014-12-17
GB1422472.9 2014-12-17
PCT/EP2015/080029 WO2016097004A1 (en) 2014-12-17 2015-12-16 BICYCLOHETEROARYL-HETEROARYL-BENZOIC ACID COMPOUNDS AS RETINOIC ACID RECEPTOR BETA (RARβ) AGONISTS

Publications (2)

Publication Number Publication Date
CA2970574A1 CA2970574A1 (en) 2016-06-23
CA2970574C true CA2970574C (en) 2023-09-19

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2970574A Active CA2970574C (en) 2014-12-17 2015-12-16 Bicycloheteroaryl-heteroaryl-benzoic acid compounds as retinoic acid receptor beta (rar.beta.) agonists

Country Status (11)

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US (4) US9994559B2 (https=)
EP (1) EP3233842B1 (https=)
JP (1) JP6596090B2 (https=)
KR (1) KR102526625B1 (https=)
CN (1) CN107207488B (https=)
AU (1) AU2015367531B2 (https=)
BR (1) BR112017012588B8 (https=)
CA (1) CA2970574C (https=)
ES (1) ES3029609T3 (https=)
IL (1) IL252882B (https=)
WO (1) WO2016097004A1 (https=)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107207488B (zh) 2014-12-17 2020-11-17 伦敦皇家学院 作为视黄酸受体β(RARβ)激动剂的双环杂芳基-杂芳基-苯甲酸化合物
GB201610867D0 (en) * 2016-06-22 2016-08-03 King S College London Crystalline forms of a therapeutic compound and processes for their preparation
CN111892591A (zh) * 2019-05-06 2020-11-06 南京科技职业学院 一种维奈托克关键中间体的合成方法
GB201907647D0 (en) * 2019-05-30 2019-07-17 King S College London Therapeutic methods
CN115427401B (zh) 2020-05-29 2025-04-11 巴斯夫欧洲公司 取代4-(n′-羟基甲脒基)苯甲酸的制备
CN112552252B (zh) * 2020-09-30 2024-01-02 浙江美诺华药物化学有限公司 一种氟雷拉纳中间体的制备方法
CN113264832A (zh) * 2021-05-13 2021-08-17 南京爱可德夫科技开发有限公司 一种合成高纯度2-氟-4-溴苯甲酸叔丁酯的方法
CN116640071B (zh) * 2023-05-04 2024-08-30 四川青木制药有限公司 一种制备2-甲基4-甲醛肟基苯甲酸及其酯类衍生物的方法

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP9802290A3 (en) 1995-06-07 2002-02-28 Nippon Shinyaku Co Ltd Pyrrole derivatives and pharmaceutical compositions containing them
JP3964478B2 (ja) 1995-06-30 2007-08-22 エーザイ・アール・アンド・ディー・マネジメント株式会社 ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬
KR100485642B1 (ko) 1996-03-18 2005-09-30 에자이 가부시키가이샤 축합고리함유카르복실산유도체
JPH10158192A (ja) 1996-10-03 1998-06-16 Eisai Co Ltd 移植片対宿主疾患(gvhd)の治療および臓器移植時の移植片拒絶反応抑制のための医薬組成物
GB9907461D0 (en) 1999-03-31 1999-05-26 King S College London Neurite regeneration
JP2000154150A (ja) * 1997-10-22 2000-06-06 Eisai Co Ltd 腎炎予防・治療剤としてのレチノイン酸アゴニスト
CA2307613A1 (en) 1997-10-22 1999-04-29 Eisai Co., Ltd. Retinoic acid agonist as a prophylactic and therapeutic agent for nephritis
US6809107B1 (en) * 1999-07-09 2004-10-26 Ortho-Mcneil Pharmaceutical, Inc. Neurotrophic pyrrolidines and piperidines, and related compositions and methods
US20020048580A1 (en) * 2000-06-07 2002-04-25 Institut National De La Sante Et De La Recherche Medicale Method of inducing lung branching
KR20040004705A (ko) 2001-06-08 2004-01-13 시토비아 인크. 카스파제의 활성제 및 아폽토시스의 유도제로서의 치환된3-아릴-5-아릴-[1,2,4]-옥사디아졸과 유사체 및 이의 용도
JP2003081832A (ja) 2001-06-26 2003-03-19 Takeda Chem Ind Ltd レチノイド関連受容体機能調節剤
WO2003062230A1 (en) * 2002-01-21 2003-07-31 Eisai Co., Ltd. Conbinatorial library of heterocycle compounds
IL166510A0 (en) 2002-08-09 2006-01-15 Nps Pharma Inc 1,2,4"oxadiazole as modulators of metabotropic glutamate receptor-5
EP4101846B1 (en) * 2003-04-11 2023-08-02 PTC Therapeutics, Inc. 1,2,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease
WO2005077373A2 (en) 2004-02-03 2005-08-25 Astrazeneca Ab Treatment of gastro-esophageal reflux disease (gerd)
EP1799659A1 (en) * 2004-10-13 2007-06-27 PTC Therapeutics, Inc. Compounds for nonsense suppression, and methods for their use
US20090176837A1 (en) 2005-07-12 2009-07-09 Sony Corporation Compounds with activity at retinoic acid receptors
CN102047061A (zh) 2008-05-30 2011-05-04 福斯特韦勒能源股份公司 通过氧化燃料燃烧发电的方法和系统
KR101220182B1 (ko) * 2009-02-25 2013-01-11 에스케이바이오팜 주식회사 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법
GB0915196D0 (en) * 2009-09-01 2009-10-07 King S College London Therapeutic compounds and their use
US20120289476A1 (en) 2009-12-11 2012-11-15 Jay Allan Barth Methods for treating methylmalonic acidemia
GB201403093D0 (en) 2014-02-21 2014-04-09 Cancer Rec Tech Ltd Therapeutic compounds and their use
CN107207488B (zh) * 2014-12-17 2020-11-17 伦敦皇家学院 作为视黄酸受体β(RARβ)激动剂的双环杂芳基-杂芳基-苯甲酸化合物

Also Published As

Publication number Publication date
US10385044B2 (en) 2019-08-20
CA2970574A1 (en) 2016-06-23
US20210130337A1 (en) 2021-05-06
EP3233842B1 (en) 2025-03-26
IL252882B (en) 2020-04-30
US20200131165A1 (en) 2020-04-30
US9994559B2 (en) 2018-06-12
WO2016097004A1 (en) 2016-06-23
EP3233842C0 (en) 2025-03-26
US20170327489A1 (en) 2017-11-16
BR112017012588B1 (pt) 2023-11-07
IL252882A0 (en) 2017-08-31
KR102526625B1 (ko) 2023-04-27
EP3233842A1 (en) 2017-10-25
KR20170097125A (ko) 2017-08-25
CN107207488B (zh) 2020-11-17
JP2017537967A (ja) 2017-12-21
AU2015367531A1 (en) 2017-07-06
US20190010146A1 (en) 2019-01-10
BR112017012588B8 (pt) 2024-02-15
US10752616B2 (en) 2020-08-25
BR112017012588A2 (pt) 2018-11-13
JP6596090B2 (ja) 2019-10-23
AU2015367531B2 (en) 2020-04-30
US11401265B2 (en) 2022-08-02
CN107207488A (zh) 2017-09-26
ES3029609T3 (en) 2025-06-24

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