CA2976776C - Phenothiazine analogues as mitochondrial therapeutic agents - Google Patents

Phenothiazine analogues as mitochondrial therapeutic agents Download PDF

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Publication number
CA2976776C
CA2976776C CA2976776A CA2976776A CA2976776C CA 2976776 C CA2976776 C CA 2976776C CA 2976776 A CA2976776 A CA 2976776A CA 2976776 A CA2976776 A CA 2976776A CA 2976776 C CA2976776 C CA 2976776C
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Prior art keywords
alkyl
optionally substituted
compound according
aryl
cycloalkyl
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CA2976776A
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English (en)
French (fr)
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CA2976776A1 (en
Inventor
Sidney Hecht
Omar Khdour
Sandipan Roy Chowdhury
Indrajit BANDYOPADHAY
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Arizona State University Downtown Phoenix campus
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Arizona State University Downtown Phoenix campus
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Publication of CA2976776A1 publication Critical patent/CA2976776A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P25/14—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurology (AREA)
  • Public Health (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2976776A 2015-02-17 2016-02-17 Phenothiazine analogues as mitochondrial therapeutic agents Active CA2976776C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562117205P 2015-02-17 2015-02-17
US62/117,205 2015-02-17
PCT/US2016/018233 WO2016133995A1 (en) 2015-02-17 2016-02-17 Phenothiazine analogues as mitochondrial therapeutic agents

Publications (2)

Publication Number Publication Date
CA2976776A1 CA2976776A1 (en) 2016-08-25
CA2976776C true CA2976776C (en) 2023-06-20

Family

ID=56692740

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2976776A Active CA2976776C (en) 2015-02-17 2016-02-17 Phenothiazine analogues as mitochondrial therapeutic agents

Country Status (7)

Country Link
US (3) US10472340B2 (enExample)
EP (1) EP3258938B1 (enExample)
JP (3) JP6807337B2 (enExample)
AU (3) AU2016220096B2 (enExample)
CA (1) CA2976776C (enExample)
DK (1) DK3258938T3 (enExample)
WO (1) WO2016133995A1 (enExample)

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CA2976937C (en) 2015-02-17 2023-04-04 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
CA2976776C (en) 2015-02-17 2023-06-20 Arizona Board Of Regents On Behalf Of Arizona State University Phenothiazine analogues as mitochondrial therapeutic agents
WO2017218537A1 (en) 2016-06-15 2017-12-21 Arizona Board Of Regents On Behalf Of Arizona State University Prodrug and profluorescent compounds for selective mitochondrial imaging and therapeutic targeting
US11390605B2 (en) 2016-08-25 2022-07-19 Arizona Board Of Regents On Behalf Of Arizona State University Substituted pyrimidine compounds as multifunctional radical quenchers and their uses
US12570622B2 (en) 2016-08-25 2026-03-10 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
WO2018039487A1 (en) 2016-08-25 2018-03-01 Arizona Board Of Regents On Behalf Of Arizona State University Therapeutic compounds
WO2018129411A1 (en) * 2017-01-06 2018-07-12 Bioelectron Technology Corporation Aryl- and heteroaryl-resorufin derivatives for treatment of oxidative stress disorders and liver and kidney disorders
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CN108484527B (zh) * 2018-04-27 2022-01-14 成都恒昊创新科技有限公司 一种10h-吩噻嗪类铁死亡抑制剂及其制备方法与应用
US12502408B2 (en) 2018-07-22 2025-12-23 Minovia Therapeutics Ltd. Mitochondrial augmentation therapy for primary mitochondrial diseases
BR112021000802A2 (pt) * 2018-07-26 2021-04-13 Wista Laboratories Ltd. Dosagem otimizada de diaminofenotiazinas em populações
US12110313B2 (en) 2019-02-28 2024-10-08 Arizona Board Of Regents On Behalf Of Arizona State University Engineered bacterial ribosome compositions and methods
WO2022171265A1 (en) * 2021-02-09 2022-08-18 Boehringer Ingelheim International Gmbh Modulators of complex i
CN119504646A (zh) * 2024-11-07 2025-02-25 长春工业大学 新型含有吩噻嗪结构药物小分子的合成及抗肿瘤活性研究

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Also Published As

Publication number Publication date
JP6807337B2 (ja) 2021-01-06
DK3258938T3 (da) 2021-02-01
JP7113055B2 (ja) 2022-08-04
US20220081404A1 (en) 2022-03-17
EP3258938B1 (en) 2020-12-02
AU2020202836B2 (en) 2020-12-17
AU2021201137A1 (en) 2021-03-11
US20200115355A1 (en) 2020-04-16
JP2021006573A (ja) 2021-01-21
EP3258938A4 (en) 2018-10-31
AU2020202836A1 (en) 2020-05-21
AU2016220096A1 (en) 2017-08-31
US20180065941A1 (en) 2018-03-08
WO2016133995A1 (en) 2016-08-25
JP2018505228A (ja) 2018-02-22
US10472340B2 (en) 2019-11-12
AU2016220096B2 (en) 2020-01-30
JP2022141896A (ja) 2022-09-29
US11034662B2 (en) 2021-06-15
CA2976776A1 (en) 2016-08-25
EP3258938A1 (en) 2017-12-27

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