CA2748705C - Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof - Google Patents

Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof Download PDF

Info

Publication number
CA2748705C
CA2748705C CA2748705A CA2748705A CA2748705C CA 2748705 C CA2748705 C CA 2748705C CA 2748705 A CA2748705 A CA 2748705A CA 2748705 A CA2748705 A CA 2748705A CA 2748705 C CA2748705 C CA 2748705C
Authority
CA
Canada
Prior art keywords
ethoxy
pyridin
methyl
vinyl
radiolabeled
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2748705A
Other languages
English (en)
French (fr)
Other versions
CA2748705A1 (en
Inventor
Tyler Benedum
Geoff Golding
Nathaniel Lim
Wei Zhang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Avid Radiopharmaceuticals Inc
Original Assignee
Avid Radiopharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Avid Radiopharmaceuticals Inc filed Critical Avid Radiopharmaceuticals Inc
Publication of CA2748705A1 publication Critical patent/CA2748705A1/en
Application granted granted Critical
Publication of CA2748705C publication Critical patent/CA2748705C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365Lactones
    • A61K31/375Ascorbic acid, i.e. vitamin C; Salts thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61MDEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M37/00Other apparatus for introducing media into the body; Percutany, i.e. introducing medicines into the body by diffusion through the skin
    • A61M37/0069Devices for implanting pellets, e.g. markers or solid medicaments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Anesthesiology (AREA)
  • Hematology (AREA)
  • Psychology (AREA)
  • Dermatology (AREA)
  • Medical Informatics (AREA)
  • Hospice & Palliative Care (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychiatry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2748705A 2008-12-31 2009-12-29 Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof Active CA2748705C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14188508P 2008-12-31 2008-12-31
US61/141,885 2008-12-31
PCT/US2009/069741 WO2010078370A1 (en) 2008-12-31 2009-12-29 Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof

Publications (2)

Publication Number Publication Date
CA2748705A1 CA2748705A1 (en) 2010-07-08
CA2748705C true CA2748705C (en) 2017-05-02

Family

ID=42310197

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2748705A Active CA2748705C (en) 2008-12-31 2009-12-29 Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof

Country Status (35)

Country Link
US (1) US20100172836A1 (https=)
EP (1) EP2381967B1 (https=)
JP (1) JP5717650B2 (https=)
KR (1) KR20110119670A (https=)
CN (1) CN102271716B (https=)
AU (1) AU2009335049B2 (https=)
BR (1) BRPI0923890A2 (https=)
CA (1) CA2748705C (https=)
CO (1) CO6341578A2 (https=)
CR (1) CR20110410A (https=)
CY (1) CY1118658T1 (https=)
DK (1) DK2381967T3 (https=)
DO (1) DOP2011000210A (https=)
EA (1) EA023014B1 (https=)
EC (1) ECSP11011242A (https=)
ES (1) ES2620402T3 (https=)
HN (1) HN2011001810A (https=)
HR (1) HRP20170453T1 (https=)
HU (1) HUE033649T2 (https=)
IL (1) IL213674A (https=)
LT (1) LT2381967T (https=)
MA (1) MA33004B1 (https=)
MX (1) MX2011007063A (https=)
MY (1) MY162312A (https=)
NZ (1) NZ593848A (https=)
PE (1) PE20120007A1 (https=)
PL (1) PL2381967T3 (https=)
PT (1) PT2381967T (https=)
RS (1) RS55674B1 (https=)
SG (1) SG172439A1 (https=)
SI (1) SI2381967T1 (https=)
TN (1) TN2011000318A1 (https=)
UA (1) UA105914C2 (https=)
WO (1) WO2010078370A1 (https=)
ZA (1) ZA201104824B (https=)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9987379B2 (en) * 2008-09-30 2018-06-05 Case Western Reserve University Molecular probes for imaging of myelin
SG185782A1 (en) 2010-06-04 2013-01-30 Piramal Imaging Sa Method for production of f-18 labeled amyloid beta ligands
TWI504414B (zh) * 2010-06-04 2015-10-21 Bayer Schering Pharma Ag 生產F-18標記之Aβ配位體之方法
WO2011151282A1 (en) * 2010-06-04 2011-12-08 Bayer Pharma Aktiengesellschaft Method for production of f-18 labeled amyloid beta ligand
EP2699157B1 (en) * 2011-04-21 2018-03-14 The Regents of The University of California Functionalized magnetic nanoparticles and use in imaging amyloid deposits and neurofibrillary tangles
BR112013032610B1 (pt) * 2011-06-21 2022-05-31 Life Molecular Imaging Sa Formulações de estilbeno fluorado adequadas para imagiologia pet, e seus métodos de preparação, obtenção e filtração estéril
EP2768790A1 (en) 2011-10-19 2014-08-27 Piramal Imaging SA IMPROVED METHOD FOR PRODUCTION OF F-18 LABELED Aß LIGANDS
CN102432529B (zh) * 2011-11-14 2014-03-26 江苏省原子医学研究所 一种苯乙烯基吡啶二硫二氮衍生物的制备方法
US20150004100A1 (en) * 2011-12-15 2015-01-01 Ge Healthcare Limited Heterocyclic compounds as imaging probes of tau pathology
CN102526765B (zh) * 2011-12-31 2014-07-30 郑州泰基鸿诺药物科技有限公司 一种Aβ斑块显像剂及其制备方法
CN103965105A (zh) * 2013-01-29 2014-08-06 中山大学 苯乙烯基喹啉衍生物及其在治疗阿尔茨海默病症中的应用
CN103645254B (zh) * 2013-11-28 2015-01-07 江苏省原子医学研究所 一种Aβ斑块显像剂前体AV45的含量分析方法
WO2017014599A1 (ko) * 2015-07-22 2017-01-26 주식회사 씨코헬스케어 [18f]플루오로-도파의 방사화학적 순도를 안정화시키는 조성물 및 이의 제조방법
CA3003884C (en) * 2015-11-13 2020-04-21 Eli Lilly And Company Azetidine derivatives for tau imaging
WO2017156303A1 (en) * 2016-03-09 2017-09-14 Case Western Reserve University Radioligands for myelin
CN107198780A (zh) * 2016-03-18 2017-09-26 南京江原安迪科正电子研究发展有限公司 放射性药物组合物及其制备方法、应用
CN106018575B (zh) * 2016-05-05 2018-10-19 江苏省原子医学研究所 一种PET显像剂前体TsOP-(+)-DTBZ及其光学异构体的分离测定方法
US10695450B2 (en) * 2016-07-26 2020-06-30 Laboratoires Cyclopharma Synthesis of a radioactive agent composition
JP2019534284A (ja) * 2016-11-08 2019-11-28 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 臨床設定用[f−18]fddnpの複数ドーズ合成方法
TW201906818A (zh) * 2017-05-31 2019-02-16 美商511製藥公司 新穎氘取代之正子發射斷層掃描(pet)顯影劑及其藥理應用
EP3743115A1 (en) * 2018-01-24 2020-12-02 AC Immune SA Diagnostic compositions for pet imaging, a method for manufacturing the diagnostic composition and its use in diagnostics
CN111499570B (zh) * 2019-01-31 2023-05-16 中国医学科学院放射医学研究所 一种av-45中间体的合成方法
CN111499544B (zh) * 2019-01-31 2022-12-02 中国医学科学院放射医学研究所 一种一锅法制备N-Boc-N-甲基-4-氨基苯乙烯的合成方法
WO2020202831A1 (ja) * 2019-03-29 2020-10-08 国立研究開発法人量子科学技術研究開発機構 放射性医薬の製造方法及び放射性医薬
CN115400232A (zh) * 2021-05-26 2022-11-29 汉中汉核医疗科技有限公司 一种放射性药物合成方法
CN115403434A (zh) * 2021-05-26 2022-11-29 汉中汉核医疗科技有限公司 一种放射性药物的合成方法
CN113582885B (zh) * 2021-08-30 2023-04-21 南京克米斯璀新能源科技有限公司 一种烷基磺酸钠的生产方法
CN114805190A (zh) * 2022-06-08 2022-07-29 吉林大学第一医院 一种甲基苯胺类Aβ蛋白显像剂的双柱合成方法
WO2024107620A1 (en) * 2022-11-14 2024-05-23 Eli Lilly And Company Polymorphic forms of florbetapir precursor av-105
CN119080714A (zh) * 2024-09-12 2024-12-06 四川大学 一种偶氮苯磺酸酯化合物及其制备方法和应用、放射性探针的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007525211A (ja) * 2004-01-19 2007-09-06 テクニオン リサーチ アンド ディベロップメント ファウンデーション リミテッド パーキンソン病の診断検査
EP2213652B1 (en) * 2004-12-17 2014-10-22 The Trustees of The University of Pennsylvania Stilbene derivatives and their use for binding and imaging amyloid plaques
PL1999109T3 (pl) * 2006-03-30 2012-05-31 Univ Pennsylvania Pochodne styrylopirydyny i ich zastosowanie do wiązania i obrazowania blaszek amyloidowych

Also Published As

Publication number Publication date
MX2011007063A (es) 2011-12-16
BRPI0923890A2 (pt) 2015-07-28
CR20110410A (es) 2011-12-08
AU2009335049A1 (en) 2011-07-21
IL213674A0 (en) 2011-07-31
EP2381967A1 (en) 2011-11-02
RS55674B1 (sr) 2017-06-30
PT2381967T (pt) 2017-02-24
TN2011000318A1 (en) 2012-12-17
HRP20170453T1 (hr) 2017-06-02
DOP2011000210A (es) 2011-09-15
ES2620402T3 (es) 2017-06-28
ECSP11011242A (es) 2011-10-31
HK1162951A1 (en) 2012-09-07
CN102271716B (zh) 2014-11-19
IL213674A (en) 2016-04-21
PE20120007A1 (es) 2012-01-16
JP5717650B2 (ja) 2015-05-13
JP2012514007A (ja) 2012-06-21
MY162312A (en) 2017-05-31
MA33004B1 (fr) 2012-01-02
SI2381967T1 (sl) 2017-03-31
WO2010078370A1 (en) 2010-07-08
EA201170911A1 (ru) 2011-12-30
CA2748705A1 (en) 2010-07-08
DK2381967T3 (en) 2017-03-27
LT2381967T (lt) 2017-04-25
US20100172836A1 (en) 2010-07-08
ZA201104824B (en) 2013-01-30
EA023014B1 (ru) 2016-04-29
PL2381967T3 (pl) 2017-06-30
EP2381967A4 (en) 2013-01-02
NZ593848A (en) 2013-09-27
HUE033649T2 (en) 2017-12-28
CY1118658T1 (el) 2017-07-12
KR20110119670A (ko) 2011-11-02
CN102271716A (zh) 2011-12-07
EP2381967B1 (en) 2017-01-18
HN2011001810A (es) 2013-08-12
UA105914C2 (uk) 2014-07-10
CO6341578A2 (es) 2011-11-21
AU2009335049B2 (en) 2015-07-16
SG172439A1 (en) 2011-07-28

Similar Documents

Publication Publication Date Title
CA2748705C (en) Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof
JP7500551B2 (ja) 前立腺特異的膜抗原(psma)の標識化阻害剤、画像化剤としてのそれらの使用、及びpsma発現がんの処置のための医薬剤
JP2019218371A (ja) 造影剤の合成および使用のための組成物、方法およびシステム
KR101602912B1 (ko) [18f]플루오르메틸기가 도입된 뇌신경염증 표적 양성자방출단층촬영 방사성추적자, 이의 합성 및 그를 이용한 생물학적 결과 평가 방법
CN103298789A (zh) 作为τ蛋白病理成像探针的杂环化合物
EP2218464A1 (en) Compounds for non-invasive measurement of aggregates of amyloid peptides
US20080219922A1 (en) Alzheimer's Disease Imaging Agents
EP3835293B1 (en) Monoamine oxidase b imaging probe
HK1162951B (en) Synthesis of 18f-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof
WO2014184682A1 (en) Radiolabeled gnrh antagonists as pet imaging agents
WO2010135493A2 (en) Alzheimer's disease imaging agents
HK40120870A (en) Labeled inhibitors of prostate specific membrane antigen (psma), their use as imaging agents and pharmaceutical agents for the treatment of psma-expressing cancers
JP2021102593A (ja) タウを画像化する新規化合物
HK1200030B (en) Compositions, methods, and systems for the synthesis and use of imaging agents

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20141222

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 15TH ANNIV.) - STANDARD

Year of fee payment: 15

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241209

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250826

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 16TH ANNIV.) - STANDARD

Year of fee payment: 16

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251124

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251124