CA2948721C - Deuterated compounds and uses thereof - Google Patents

Deuterated compounds and uses thereof Download PDF

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Publication number
CA2948721C
CA2948721C CA2948721A CA2948721A CA2948721C CA 2948721 C CA2948721 C CA 2948721C CA 2948721 A CA2948721 A CA 2948721A CA 2948721 A CA2948721 A CA 2948721A CA 2948721 C CA2948721 C CA 2948721C
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CA
Canada
Prior art keywords
compound
pharmaceutically acceptable
acceptable salt
animal
deuterated
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CA2948721A
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English (en)
French (fr)
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CA2948721A1 (en
Inventor
Jan Marik
Joseph P. Lyssikatos
Simon Williams
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F Hoffmann La Roche AG
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F Hoffmann La Roche AG
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Publication of CA2948721A1 publication Critical patent/CA2948721A1/en
Application granted granted Critical
Publication of CA2948721C publication Critical patent/CA2948721C/en
Active legal-status Critical Current
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    • 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • A61K51/041Heterocyclic compounds
    • A61K51/044Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K51/0459Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
    • 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
    • A61P25/28Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2948721A 2014-05-13 2015-05-12 Deuterated compounds and uses thereof Active CA2948721C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201461992717P 2014-05-13 2014-05-13
US61/992,717 2014-05-13
PCT/EP2015/060447 WO2015173225A1 (en) 2014-05-13 2015-05-12 Deuterated heterocyclic compounds and their use as imaging agents

Publications (2)

Publication Number Publication Date
CA2948721A1 CA2948721A1 (en) 2015-11-19
CA2948721C true CA2948721C (en) 2023-03-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2948721A Active CA2948721C (en) 2014-05-13 2015-05-12 Deuterated compounds and uses thereof

Country Status (21)

Country Link
US (4) US10076581B2 (enExample)
EP (2) EP3143011B1 (enExample)
JP (2) JP6529986B2 (enExample)
KR (2) KR102530129B1 (enExample)
CN (2) CN110483522B (enExample)
AU (2) AU2015261008B2 (enExample)
CA (1) CA2948721C (enExample)
DK (1) DK3143011T3 (enExample)
ES (1) ES2867814T3 (enExample)
HR (1) HRP20210641T1 (enExample)
HU (1) HUE053939T2 (enExample)
IL (3) IL280791B2 (enExample)
LT (1) LT3143011T (enExample)
MX (2) MX376163B (enExample)
PL (1) PL3143011T3 (enExample)
PT (1) PT3143011T (enExample)
RS (1) RS61810B1 (enExample)
RU (1) RU2696492C2 (enExample)
SG (2) SG10201805628TA (enExample)
SI (1) SI3143011T1 (enExample)
WO (1) WO2015173225A1 (enExample)

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SI3143011T1 (sl) * 2014-05-13 2021-08-31 F. Hoffmann-La Roche Ag Devterirane heterociklične spojine in njihova uporaba kot kontrastna sredstva
JP7059270B2 (ja) 2016-07-22 2022-04-25 エーシー・イミューン・エス・アー タウタンパク質凝集体を画像化するための化合物
IL264239B (en) 2016-07-22 2022-08-01 Ac Immune Sa Compounds for imaging tau protein aggregates
EP3535265A4 (en) * 2016-11-01 2020-07-08 Arvinas, Inc. PROTACS TARGETING ON TAU PROTEIN AND RELATED METHODS FOR USE
SG11202001684PA (en) 2017-10-06 2020-03-30 Forma Therapeutics Inc Inhibiting ubiquitin specific peptidase 30
EP3743423A1 (en) 2018-01-24 2020-12-02 AC Immune SA Gamma-carboline compounds for the detection of tau aggregates
EP3743426A1 (en) 2018-01-24 2020-12-02 AC Immune SA Azacarboline compounds for the detection of tau aggregates
EP3758696B1 (en) 2018-03-02 2026-02-25 The Trustees of the University of Pennsylvania [1,2,4]triazolo[1,5-a]pyrimidine compounds and use in stabilizing microtubules
ES2988920T3 (es) 2018-05-17 2024-11-22 Forma Therapeutics Inc Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina
US11707452B2 (en) 2018-08-20 2023-07-25 Arvinas Operations, Inc. Modulators of alpha-synuclein proteolysis and associated methods of use
WO2020061103A1 (en) 2018-09-18 2020-03-26 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as src homology-2 phosphatase inhibitors
PL3860989T3 (pl) 2018-10-05 2023-07-10 Forma Therapeutics, Inc. Sprzężone piroliny, które działają jako inhibitory proteazy 30 swoistej dla ubikwityny (usp30)
PT3860998T (pt) 2018-10-05 2024-04-02 Annapurna Bio Inc Compostos e composições para o tratamento de condições associadas à atividade do recetor apj
TWI767148B (zh) 2018-10-10 2022-06-11 美商弗瑪治療公司 抑制脂肪酸合成酶(fasn)
JP7119978B2 (ja) * 2018-12-20 2022-08-17 オムロン株式会社 制御装置およびプログラム
US11325912B2 (en) 2019-05-09 2022-05-10 Genentech, Inc. Regio-selective synthesis of imidazo[1,2-a]pyrimidines
WO2021011913A1 (en) 2019-07-17 2021-01-21 Arvinas Operations, Inc. Tau-protein targeting compounds and associated methods of use
CN113526526A (zh) * 2021-07-12 2021-10-22 苏州大学 氘代氨制备方法及以其作为氘源参与的氘代反应
MX2024002295A (es) 2021-08-27 2024-03-07 Genentech Inc Metodos para tratar las patologias de tau.
WO2023245008A1 (en) 2022-06-13 2023-12-21 Genentech, Inc. Methods of delaying or preventing the onset of alzheimer's disease using crenezumab
WO2025155625A1 (en) * 2024-01-16 2025-07-24 Eli Lilly And Company Novel compounds for tau imaging
CN118957609B (zh) * 2024-07-23 2025-09-09 无锡绿能电合科技有限公司 一种氟代芳环的氘代方法

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DE76515C (de) F. MORA in Mailand Verfahren zur Herstellung imitirter Ledertapete aus Baumwollstoff
DD76515A (enExample) *
EP1340759A1 (en) 2002-02-28 2003-09-03 Sanofi-Synthelabo 1-[alkyl], 1-[(heteroaryl)alkyl] and 1-[(aryl)alkyl]-7-(pyrimidin-4-yl)-imidazo[1,2-a]pyrimidin-5(1H)-one derivatives
US6875784B2 (en) 2002-10-09 2005-04-05 Pharmacia & Upjohn Company Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives
ES2628882T3 (es) * 2006-03-30 2017-08-04 The Trustees Of The University Of Pennsylvania Derivados de estirilpiridina, y su uso para unir y formar imágenes de placas amiloides
JP5647519B2 (ja) * 2007-09-13 2014-12-24 コンサート ファーマシューティカルズ インコーポレイテッド 重水素化カテコールおよびベンゾ[d][1,3]ジオキソールおよびその誘導体の合成
LT2247558T (lt) 2008-02-14 2022-04-11 Eli Lilly And Company Nauji vizualizavimo agentai neurologinės disfunkcijos aptikimui
US8932557B2 (en) 2008-02-14 2015-01-13 Eli Lilly And Company Imaging agents for detecting neurological dysfunction
US20100144657A1 (en) * 2008-12-09 2010-06-10 Auspex Pharmaceuticals, Inc. PHENYLPIPERIDINE MODULATORS OF mu-OPIOID RECEPTORS
US8691187B2 (en) 2009-03-23 2014-04-08 Eli Lilly And Company Imaging agents for detecting neurological disorders
EP2411057B1 (en) 2009-03-23 2020-05-06 Eli Lilly and Company Imaging agents for detecting neurological disorders
EP2450332A1 (en) 2010-10-22 2012-05-09 Bayer Pharma Aktiengesellschaft Compounds for use in Imaging, diagnosing and/or treatment of diseases of the central nervous system (F-D2-Deprenyl)
BR112013011737A2 (pt) * 2010-11-15 2016-08-09 Univ Leuven Kath composto, uso de um composto composição farmacêutica, e, método de tratamento ou prevenção de uma infecção por hiv
KR101609504B1 (ko) * 2012-05-22 2016-04-05 일라이 릴리 앤드 캄파니 신경계 기능장애를 검출하기 위한 카르볼린계 및 카르바졸계 영상화제
NO3055308T3 (enExample) * 2013-10-08 2018-04-21
SI3143011T1 (sl) 2014-05-13 2021-08-31 F. Hoffmann-La Roche Ag Devterirane heterociklične spojine in njihova uporaba kot kontrastna sredstva

Also Published As

Publication number Publication date
ES2867814T3 (es) 2021-10-20
US20160250358A1 (en) 2016-09-01
CN106459059B (zh) 2019-09-24
AU2019203369A1 (en) 2019-06-06
WO2015173225A1 (en) 2015-11-19
RU2016147742A3 (enExample) 2018-10-08
BR112016026443A8 (pt) 2021-07-06
HUE053939T2 (hu) 2021-08-30
JP2017515856A (ja) 2017-06-15
CN110483522A (zh) 2019-11-22
RU2016147742A (ru) 2018-06-18
US20200297875A1 (en) 2020-09-24
IL280791A (en) 2021-04-29
US20190201561A1 (en) 2019-07-04
JP6529986B2 (ja) 2019-06-12
IL280791B1 (en) 2023-11-01
CA2948721A1 (en) 2015-11-19
PT3143011T (pt) 2021-04-26
MX2016014615A (es) 2017-03-06
JP2019147825A (ja) 2019-09-05
LT3143011T (lt) 2021-05-10
EP3143011A1 (en) 2017-03-22
NZ726208A (en) 2023-11-24
EP3143011B1 (en) 2021-03-03
SI3143011T1 (sl) 2021-08-31
KR20170002639A (ko) 2017-01-06
US10675367B2 (en) 2020-06-09
AU2019203369B2 (en) 2020-06-04
MX384604B (es) 2025-03-14
US11504440B2 (en) 2022-11-22
RU2696492C2 (ru) 2019-08-02
SG10201805628TA (en) 2018-08-30
CN106459059A (zh) 2017-02-22
IL248692A0 (en) 2017-01-31
IL271631B (en) 2021-05-31
KR20230035445A (ko) 2023-03-13
CN110483522B (zh) 2022-05-03
KR102618139B1 (ko) 2023-12-27
AU2015261008A1 (en) 2016-11-17
IL280791B2 (en) 2024-03-01
IL271631A (en) 2020-02-27
US10076581B2 (en) 2018-09-18
IL248692B (en) 2020-01-30
KR102530129B1 (ko) 2023-05-10
AU2015261008B2 (en) 2019-02-14
PL3143011T3 (pl) 2021-07-19
SG11201609281UA (en) 2016-12-29
NZ764181A (en) 2023-11-24
JP6681498B2 (ja) 2020-04-15
HRP20210641T1 (hr) 2021-05-28
DK3143011T3 (da) 2021-05-03
US12214058B2 (en) 2025-02-04
MX376163B (es) 2025-03-07
US20230218782A1 (en) 2023-07-13
RS61810B1 (sr) 2021-06-30
MX2020010847A (es) 2021-07-16
EP3901145A1 (en) 2021-10-27
BR112016026443A2 (pt) 2017-08-15

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