CA2873963C - Carboline and carbazole based imaging agents for detecting neurological dysfunction - Google Patents

Carboline and carbazole based imaging agents for detecting neurological dysfunction Download PDF

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Publication number
CA2873963C
CA2873963C CA2873963A CA2873963A CA2873963C CA 2873963 C CA2873963 C CA 2873963C CA 2873963 A CA2873963 A CA 2873963A CA 2873963 A CA2873963 A CA 2873963A CA 2873963 C CA2873963 C CA 2873963C
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mmol
ethoxy
reaction
optionally replaced
compound
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CA2873963A
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English (en)
French (fr)
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CA2873963A1 (en
Inventor
Anna Katrin Szardenings
Hartmuth C. Kolb
Joseph C. Walsh
Gang Chen
Umesh B. Gangadharmath
Dhanalakshmi Kasi
Changhui Liu
Anjana Sinha
Eric Wang
Chul Yu
Wei Zhang
Kai Chen
Vani P. Mocharla
Peter J.H. Scott
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Eli Lilly and Co
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Eli Lilly and Co
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Priority claimed from US13/477,095 external-priority patent/US8932557B2/en
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of CA2873963A1 publication Critical patent/CA2873963A1/en
Application granted granted Critical
Publication of CA2873963C publication Critical patent/CA2873963C/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • C07D209/82Carbazoles; Hydrogenated carbazoles
    • C07D209/88Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • 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
    • A61K51/0446Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K51/0455Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • 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
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
    • C07D209/82Carbazoles; Hydrogenated carbazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/18Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14Ortho-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)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Optics & Photonics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Physics & Mathematics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Proteomics, Peptides & Aminoacids (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)
  • Indole Compounds (AREA)
CA2873963A 2012-05-22 2012-10-25 Carboline and carbazole based imaging agents for detecting neurological dysfunction Active CA2873963C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13/477,095 US8932557B2 (en) 2008-02-14 2012-05-22 Imaging agents for detecting neurological dysfunction
US13/477,095 2012-05-22
PCT/US2012/061912 WO2013176698A1 (en) 2012-05-22 2012-10-25 Carboline and carbazole based imaging agents for detecting neurological dysfunction

Publications (2)

Publication Number Publication Date
CA2873963A1 CA2873963A1 (en) 2013-11-28
CA2873963C true CA2873963C (en) 2017-04-11

Family

ID=47146722

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2873963A Active CA2873963C (en) 2012-05-22 2012-10-25 Carboline and carbazole based imaging agents for detecting neurological dysfunction

Country Status (9)

Country Link
EP (1) EP2852572B1 (https=)
JP (1) JP5976206B2 (https=)
KR (1) KR101609504B1 (https=)
CN (2) CN107011342A (https=)
AU (1) AU2012381042B2 (https=)
CA (1) CA2873963C (https=)
CO (1) CO7131359A2 (https=)
ES (1) ES2792830T3 (https=)
WO (1) WO2013176698A1 (https=)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015110263A1 (en) * 2014-01-21 2015-07-30 Ac Immune Sa Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins
CA2946446C (en) * 2014-04-22 2020-11-03 Universite De Montreal Pyrido-pyrrolo-pyrimidine and pyrido-indole compounds, pharmaceutical compositions containing same and their use thereof in the expansion of hematopoietic stem cells and/or hematopoietic progenitor cells
RS61810B1 (sr) * 2014-05-13 2021-06-30 Hoffmann La Roche Deuterisana heterociklična jedinjenja i njihova upotreba kao sredstva za snimanje
US20180022748A1 (en) * 2015-02-02 2018-01-25 Ucb Biopharma Sprl 9h-pyrrolo-dipyridine derivatives
CN107207499A (zh) * 2015-03-04 2017-09-26 国立大学法人京都大学 经放射性碘标记的吡啶并[1,2‑a]苯并咪唑衍生物化合物
TW201707726A (zh) * 2015-08-19 2017-03-01 國立大學法人京都大學 放射性鹵素標誌吡啶并[1,2-a]苯并咪唑衍生物化合物
CA3003884C (en) 2015-11-13 2020-04-21 Eli Lilly And Company Azetidine derivatives for tau imaging
EP3487545A1 (en) 2016-07-22 2019-05-29 AC Immune S.A. Compounds for imaging tau protein aggregates
KR102472003B1 (ko) 2016-07-22 2022-11-29 에이씨 이뮨 에스에이 타우 단백질 응집체를 이미징하기 위한 화합물
WO2018024643A1 (en) 2016-08-02 2018-02-08 Ucb Biopharma Sprl 9h-pyrrolo-dipyridine derivatives
WO2018024642A1 (en) 2016-08-02 2018-02-08 Ucb Biopharma Sprl 9h-pyrrolo-dipyridine derivatives
IL290809B2 (en) * 2016-11-01 2024-01-01 Arvinas Operations Inc Tau-protein targeting protacs and associated methods of use
CN109884194A (zh) * 2017-12-06 2019-06-14 新疆维吾尔药业有限责任公司 一种药用植物的分离方法及其产品和应用
WO2019145291A1 (en) 2018-01-24 2019-08-01 Ac Immune Sa Gamma-carboline compounds for the detection of tau aggregates
WO2019145292A1 (en) 2018-01-24 2019-08-01 Ac Immune Sa Azacarboline compounds for the detection of tau aggregates
CN108409634B (zh) * 2018-05-10 2021-04-27 曲阜师范大学 咔唑类荧光胺类化合物标记试剂、合成和应用
EP3841100A1 (en) 2018-08-20 2021-06-30 Arvinas Operations, Inc. Proteolysis targeting chimeric (protac) compound with e3 ubiquitin ligase binding activity and targeting alpha-synuclein protein for treating neurodegenerative diseases
KR102215255B1 (ko) * 2019-06-12 2021-02-15 한국과학기술연구원 타우 응집체에 선택적으로 결합하는 형광 탐침자로서 유효한 신규 화합물 및 이의 제조 방법
CN119954801A (zh) 2019-07-17 2025-05-09 阿尔维纳斯运营股份有限公司 Tau蛋白靶向化合物及相关使用方法
US11618751B1 (en) 2022-03-25 2023-04-04 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives
US11319319B1 (en) 2021-04-07 2022-05-03 Ventus Therapeutics U.S., Inc. Compounds for inhibiting NLRP3 and uses thereof
CN116003402B (zh) * 2021-11-02 2025-08-29 上海如絮生物科技有限公司 一种三环类化合物、其中间体、制备方法和应用
CN114539250B (zh) * 2022-03-04 2023-08-29 上海裕兰生物科技有限公司 一种阿尔兹海默症PET-tau示踪剂的制备方法
US12331048B2 (en) 2022-10-31 2025-06-17 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors
JP2026504445A (ja) 2023-02-02 2026-02-05 イーライ リリー アンド カンパニー タウイメージングのための新規化合物
CN117050070B (zh) * 2023-07-05 2025-10-14 湘潭大学 一种荧光探针及其制备方法和在Aβ检测中的应用
WO2025155625A1 (en) 2024-01-16 2025-07-24 Eli Lilly And Company Novel compounds for tau imaging

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090170882A1 (en) * 2004-06-30 2009-07-02 Dashyant Dhanak Methods and compositions
FR2885905A1 (fr) * 2005-05-23 2006-11-24 Trophos Sa Nouveaux composes chimiques et leurs utilisations comme medicament
DE102006062203A1 (de) * 2006-12-22 2008-06-26 Curacyte Discovery Gmbh Substituierte 5H-Pyrimido[5,4-b]indole als Induktoren der Apoptose bei B-CLL Zellen
WO2008132454A1 (en) * 2007-04-26 2008-11-06 Ge Healthcare Limited Carbolines and their use as imaging agents
US20110046378A1 (en) * 2008-02-14 2011-02-24 Siemens Medical Solutions Usa, Inc. Novel Imaging Agents for Detecting Neurological Dysfunction
CA2731738A1 (en) * 2008-07-24 2010-01-28 Siemens Medical Solutions Usa, Inc. Imaging agents useful for identifying ad pathology
JP2012051804A (ja) * 2008-12-26 2012-03-15 Kyoto Univ Eg5阻害剤
US8691187B2 (en) * 2009-03-23 2014-04-08 Eli Lilly And Company Imaging agents for detecting neurological disorders
CN103739605B (zh) * 2009-03-23 2016-08-17 伊莱利利公司 用于检测神经障碍的显像剂
US10639608B2 (en) * 2010-04-08 2020-05-05 Siemens Medical Solutions Usa, Inc. System, device and method for preparing tracers and transferring materials during radiosynthesis
JP5585382B2 (ja) * 2010-10-22 2014-09-10 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置

Also Published As

Publication number Publication date
JP2015517572A (ja) 2015-06-22
KR101609504B1 (ko) 2016-04-05
EP2852572B1 (en) 2020-04-01
EP2852572A1 (en) 2015-04-01
ES2792830T3 (es) 2020-11-12
CN107011342A (zh) 2017-08-04
CA2873963A1 (en) 2013-11-28
AU2012381042A1 (en) 2014-11-20
CO7131359A2 (es) 2014-12-01
KR20150002854A (ko) 2015-01-07
AU2012381042B2 (en) 2015-10-01
WO2013176698A1 (en) 2013-11-28
JP5976206B2 (ja) 2016-08-23
CN104781234A (zh) 2015-07-15

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