CA2948528C - Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles - Google Patents

Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles Download PDF

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Publication number
CA2948528C
CA2948528C CA2948528A CA2948528A CA2948528C CA 2948528 C CA2948528 C CA 2948528C CA 2948528 A CA2948528 A CA 2948528A CA 2948528 A CA2948528 A CA 2948528A CA 2948528 C CA2948528 C CA 2948528C
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Prior art keywords
mmol
pyrrolo
pyridin
compound
synthesis
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CA2948528A
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English (en)
French (fr)
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CA2948528A1 (en
Inventor
Abbas M. Walji
Eric Hostetler
Thomas Greshock
Jing Li
Keith P. Moore
Idriss BENNACEF
James Mulhearn
Harold Selnick
Yaode Wang
Kun Yang
Jianmin Fu
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Merck Sharp & Dohme LLC
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Merck Sharp & Dohme LLC
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations 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
    • A61K51/04—Organic compounds
    • A61K51/041—Heterocyclic compounds
    • A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K51/0455—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations 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
    • A61K51/04—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations 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
    • A61K51/04—Organic compounds
    • A61K51/041—Heterocyclic compounds
    • A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K51/0459—Heterocyclic 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Optics & Photonics (AREA)
  • Hospice & Palliative Care (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
CA2948528A 2014-06-13 2015-06-09 Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles Active CA2948528C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CNPCT/CN2014/079834 2014-06-13
PCT/CN2014/079834 WO2015188368A1 (en) 2014-06-13 2014-06-13 Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles
PCT/US2015/034794 WO2015191506A2 (en) 2014-06-13 2015-06-09 Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles

Publications (2)

Publication Number Publication Date
CA2948528A1 CA2948528A1 (en) 2015-12-17
CA2948528C true CA2948528C (en) 2022-05-31

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CA2948528A Active CA2948528C (en) 2014-06-13 2015-06-09 Pyrrolo[2,3-c]pyridines as imaging agents for neurofibrilary tangles

Country Status (15)

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US (2) US9808542B2 (enExample)
EP (1) EP3154970B1 (enExample)
JP (1) JP6513107B2 (enExample)
KR (1) KR102478430B1 (enExample)
CN (1) CN106661018B (enExample)
AU (1) AU2015274843B2 (enExample)
BR (1) BR112016028345B1 (enExample)
CA (1) CA2948528C (enExample)
DK (1) DK3154970T3 (enExample)
ES (1) ES2763095T3 (enExample)
HU (1) HUE048395T2 (enExample)
MX (1) MX375282B (enExample)
PL (1) PL3154970T3 (enExample)
RU (1) RU2695373C2 (enExample)
WO (2) WO2015188368A1 (enExample)

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US11541033B2 (en) 2017-06-02 2023-01-03 Fujifilm Toyama Chemical Co., Ltd. Agent for preventing or treating Alzheimer's disease
RU2728717C1 (ru) 2017-06-02 2020-07-30 ФУДЖИФИЛМ Тояма Кемикал Ко., Лтд. Средство для профилактики или лечения спиноцеребеллярной атаксии
CN110691594A (zh) * 2017-06-02 2020-01-14 富士胶片富山化学株式会社 Tau蛋白病预防或治疗剂
JP7282028B2 (ja) 2017-06-02 2023-05-26 富士フイルム富山化学株式会社 脳萎縮予防または治療剤
KR20200003102A (ko) 2017-06-02 2020-01-08 후지필름 도야마 케미컬 가부시키가이샤 아밀로이드 β 단백질량 감소제
JP7227914B2 (ja) 2017-10-30 2023-02-22 富士フイルム富山化学株式会社 エモパミル結合タンパク質結合剤およびその利用
EP3743426A1 (en) 2018-01-24 2020-12-02 AC Immune SA Azacarboline compounds for the detection of tau aggregates
WO2019145291A1 (en) 2018-01-24 2019-08-01 Ac Immune Sa Gamma-carboline compounds for the detection of tau aggregates
CN111770924B (zh) * 2018-04-04 2023-05-09 深圳福沃药业有限公司 用于治疗乳腺癌的雌激素受体降解剂
KR102017324B1 (ko) * 2018-04-30 2019-09-02 경북대학교 산학협력단 신규한 asm 활성 직접 억제 화합물 2-아미노-2-(1,2,3-트리아졸-4-일)프로판-1,3-디올 유도체 및 이의 용도
CN112384517B (zh) * 2018-05-09 2023-07-14 新旭生技股份有限公司 杂芳基化合物及其用途
JP7478142B2 (ja) 2018-06-07 2024-05-02 ディスアーム セラピューティクス, インコーポレイテッド Sarm1阻害剤
CN108676007B (zh) * 2018-06-22 2020-06-26 厦门大学 放射性核素标记的苯并蝶啶类衍生物及其制备方法和应用
CA3123215C (en) 2018-12-19 2024-04-02 Disarm Therapeutics, Inc. Inhibitors of sarm1 in combination with neuroprotective agents
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US20220008563A1 (en) * 2020-07-10 2022-01-13 The Regents Of The University Of California Radiolabelled and nonradiolabelled pegylated compounds and uses thereof
BR112023002139A2 (pt) * 2020-08-06 2023-04-18 Chdi Foundation Inc Compostos de heterobiarila e agentes de imageamento para proteína huntingtina
CN112939753B (zh) * 2020-09-15 2022-04-05 浙江大学 一种1-茚酮类化合物的合成方法
KR102240400B1 (ko) * 2020-11-19 2021-04-15 한국원자력연구원 베타-아밀로이드 검출용 수용성 화합물
CN112745299B (zh) * 2021-01-07 2022-01-25 温州大学 4-氰基-7,8-二氢异喹啉衍生物及其制备方法和应用
TWI782769B (zh) * 2021-10-28 2022-11-01 行政院原子能委員會核能研究所 一種新穎神經纖維糾結微管相關蛋白質Tau造影化合物、其製備方法及用途
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Also Published As

Publication number Publication date
MX375282B (es) 2025-03-06
RU2016150404A3 (enExample) 2018-11-30
KR102478430B1 (ko) 2022-12-15
EP3154970A4 (en) 2017-11-15
RU2019115483A (ru) 2019-06-13
KR20170016481A (ko) 2017-02-13
AU2015274843B2 (en) 2018-11-22
PL3154970T3 (pl) 2020-04-30
CA2948528A1 (en) 2015-12-17
ES2763095T3 (es) 2020-05-27
US9808542B2 (en) 2017-11-07
WO2015188368A1 (en) 2015-12-17
WO2015191506A3 (en) 2016-02-04
US20180071412A1 (en) 2018-03-15
HUE048395T2 (hu) 2020-08-28
RU2016150404A (ru) 2018-07-18
BR112016028345B1 (pt) 2022-11-29
CN106661018A (zh) 2017-05-10
AU2015274843A1 (en) 2016-11-10
RU2695373C2 (ru) 2019-07-23
MX2016016384A (es) 2017-05-01
JP2017521387A (ja) 2017-08-03
BR112016028345A2 (pt) 2017-08-22
US10022461B2 (en) 2018-07-17
JP6513107B2 (ja) 2019-05-15
US20170119912A1 (en) 2017-05-04
DK3154970T3 (da) 2020-01-20
WO2015191506A2 (en) 2015-12-17
BR112016028345A8 (pt) 2021-06-29
EP3154970A2 (en) 2017-04-19
EP3154970B1 (en) 2019-11-06
CN106661018B (zh) 2019-07-19

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