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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CA2970574A
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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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King's College London
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King's College London
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    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic 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
    • C07D417/02—Heterocyclic 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
    • C07D417/04—Heterocyclic 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
    • 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
    • A61K31/41—Heterocyclic 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
    • 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
    • A61K31/41—Heterocyclic 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
    • A61K31/4245—Oxadiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/28—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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

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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

ID=55027725

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)

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

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
IL298517B2 (en) * 2020-05-29 2025-12-01 Basf Se Preparation of substituted 4-(n'-hydroxycarbamimidoyl)benzoic acids
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
ES2259795T3 (es) 1995-06-07 2006-10-16 Nippon Shinyaku Company, Limited Derivados de pirrol y composicion medicinal.
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
US6355669B1 (en) 1997-10-22 2002-03-12 Eisai Co., Ltd. Retinoic acid agonists as preventive and therapeutic agents for nephritis
CN1382140A (zh) * 1999-07-09 2002-11-27 奥索-麦克尼尔药品公司 具有神经营养活性的吡咯烷和哌啶、以及含有它们的相关组合物
US20020048580A1 (en) * 2000-06-07 2002-04-25 Institut National De La Sante Et De La Recherche Medicale Method of inducing lung branching
US7041685B2 (en) 2001-06-08 2006-05-09 Cytovia, Inc. Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
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
WO2004014881A2 (en) 2002-08-09 2004-02-19 Astra Zeneca Ab '1,2,4'oxadiazoles 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)
JP2008515992A (ja) * 2004-10-13 2008-05-15 ピーティーシー セラピューティクス,インコーポレーテッド 体細胞変異に起因する疾患の阻止/治療用医薬を製造するための規定化合物の使用
JP2009501721A (ja) 2005-07-12 2009-01-22 アカディア ファーマシューティカルズ インコーポレイテッド レチノイン酸受容体における活性を伴う化合物
AU2009253046A1 (en) 2008-05-30 2009-12-03 Foster Wheeler Energia Oy Method of and system for generating power by oxyfuel combustion
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
WO2011072281A1 (en) 2009-12-11 2011-06-16 Ptc Therapeutics, Inc. 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
BR112017012588B8 (pt) 2024-02-15
BR112017012588B1 (pt) 2023-11-07
AU2015367531A1 (en) 2017-07-06
US20200131165A1 (en) 2020-04-30
US20170327489A1 (en) 2017-11-16
US20190010146A1 (en) 2019-01-10
US11401265B2 (en) 2022-08-02
WO2016097004A1 (en) 2016-06-23
AU2015367531B2 (en) 2020-04-30
US9994559B2 (en) 2018-06-12
CN107207488A (zh) 2017-09-26
ES3029609T3 (en) 2025-06-24
IL252882A0 (en) 2017-08-31
KR20170097125A (ko) 2017-08-25
CA2970574A1 (en) 2016-06-23
US10752616B2 (en) 2020-08-25
EP3233842B1 (en) 2025-03-26
EP3233842C0 (en) 2025-03-26
US10385044B2 (en) 2019-08-20
IL252882B (en) 2020-04-30
BR112017012588A2 (pt) 2018-11-13
EP3233842A1 (en) 2017-10-25
JP2017537967A (ja) 2017-12-21
CN107207488B (zh) 2020-11-17
US20210130337A1 (en) 2021-05-06
KR102526625B1 (ko) 2023-04-27
JP6596090B2 (ja) 2019-10-23

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