WO2009155017A3 - Novel substituted azabenzoxazoles - Google Patents

Novel substituted azabenzoxazoles Download PDF

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Publication number
WO2009155017A3
WO2009155017A3 PCT/US2009/045376 US2009045376W WO2009155017A3 WO 2009155017 A3 WO2009155017 A3 WO 2009155017A3 US 2009045376 W US2009045376 W US 2009045376W WO 2009155017 A3 WO2009155017 A3 WO 2009155017A3
Authority
WO
WIPO (PCT)
Prior art keywords
relates
compounds
present
novel
amyloid
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.)
Ceased
Application number
PCT/US2009/045376
Other languages
French (fr)
Other versions
WO2009155017A2 (en
Inventor
James C. Barrow
Scott Harrison
James Mulhearn
Cyrille Sur
David L. Williams
Scott Wolkenberg
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.)
Organon Pharma UK Ltd
Merck Sharp and Dohme LLC
Original Assignee
Merck Sharp and Dohme Ltd
Merck Sharp and Dohme LLC
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 Merck Sharp and Dohme Ltd, Merck Sharp and Dohme LLC filed Critical Merck Sharp and Dohme Ltd
Priority to JP2011511794A priority Critical patent/JP2011524864A/en
Priority to ES09767329.7T priority patent/ES2554772T3/en
Priority to CA2725940A priority patent/CA2725940A1/en
Priority to AU2009260519A priority patent/AU2009260519A1/en
Priority to US12/995,314 priority patent/US8530483B2/en
Priority to EP09767329.7A priority patent/EP2300481B1/en
Publication of WO2009155017A2 publication Critical patent/WO2009155017A2/en
Publication of WO2009155017A3 publication Critical patent/WO2009155017A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04Ortho-condensed systems
    • 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
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention relates to novel amyloid binding compounds of formula (I) and methods for measuring effects of the compounds, by measuring changes of amyloid plaque level in living patients. More specifically, the present invention relates to a method of using the compounds of this invention as tracers in positron emission tomography (PET/) imaging to study amyloid deposits in brain in vivo to allow diagnosis of Alzheimer's disease. Thus, the present invention relates to use of the novel amyloid binding compounds as a diagnostic. The invention further relates to a method of measuring clinical efficacy of Alzheimer's disease therapeutic agents. Specifically, the present invention relates to novel aryl or heteroaryl substituted azabenzoxazole derivatives, compositions, and therapeutic uses and processes for making such compounds. or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, wherein: X is O or S; A and Y independently are N, or CH;
PCT/US2009/045376 2008-05-30 2009-05-28 Novel substituted azabenzoxazoles Ceased WO2009155017A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2011511794A JP2011524864A (en) 2008-05-30 2009-05-28 Novel substituted azabenzoxazole
ES09767329.7T ES2554772T3 (en) 2008-05-30 2009-05-28 Novel Azabenzoxazoles Substituted
CA2725940A CA2725940A1 (en) 2008-05-30 2009-05-28 Novel substituted azabenzoxazoles
AU2009260519A AU2009260519A1 (en) 2008-05-30 2009-05-28 Novel substituted azabenzoxazoles
US12/995,314 US8530483B2 (en) 2008-05-30 2009-05-28 Substituted azabenzoxazoles
EP09767329.7A EP2300481B1 (en) 2008-05-30 2009-05-28 Novel substituted azabenzoxazoles

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US13039908P 2008-05-30 2008-05-30
US61/130,399 2008-05-30
US19802208P 2008-10-31 2008-10-31
US61/198,022 2008-10-31

Publications (2)

Publication Number Publication Date
WO2009155017A2 WO2009155017A2 (en) 2009-12-23
WO2009155017A3 true WO2009155017A3 (en) 2010-02-18

Family

ID=40999812

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/045376 Ceased WO2009155017A2 (en) 2008-05-30 2009-05-28 Novel substituted azabenzoxazoles

Country Status (7)

Country Link
US (1) US8530483B2 (en)
EP (1) EP2300481B1 (en)
JP (1) JP2011524864A (en)
AU (1) AU2009260519A1 (en)
CA (1) CA2725940A1 (en)
ES (1) ES2554772T3 (en)
WO (1) WO2009155017A2 (en)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5369854B2 (en) 2008-04-21 2013-12-18 住友化学株式会社 Harmful arthropod control composition and condensed heterocyclic compound
EP2440058A4 (en) 2009-06-12 2012-11-21 Dana Farber Cancer Inst Inc FOUNDED HETEROCYCLIC COMPOUNDS AND USES THEREOF
US9180127B2 (en) 2009-12-29 2015-11-10 Dana-Farber Cancer Institute, Inc. Type II Raf kinase inhibitors
WO2012041292A2 (en) 2010-09-20 2012-04-05 Klinikum Darmstadt Gmbh Compounds for diagnosing neurodegenerative diseases at the retina
DE102010045797A1 (en) 2010-09-20 2012-03-22 Klinikum Darmstadt Gmbh Compounds for the diagnosis of neurodegenerative diseases of the olfactory epithelium
US9321787B2 (en) * 2011-07-07 2016-04-26 Sanofi Carboxylic acid derivatives having an oxazolo[5,4-d]pyrimidine ring
US8580816B2 (en) * 2011-07-07 2013-11-12 Sanofi Carboxylic acid derivatives having an oxazolo[5,4-b]pyridine ring
US8735402B2 (en) * 2011-07-07 2014-05-27 Sanofi Cycloalkyloxycarboxylic acid derivatives
US8907093B2 (en) 2011-07-07 2014-12-09 Sanofi Carboxylic acid derivatives having an oxazolo[4,5-c]pyridine ring
CA2856291C (en) 2011-11-17 2020-08-11 Dana-Farber Cancer Institute, Inc. Inhibitors of c-jun-n-terminal kinase (jnk)
EP2909194A1 (en) 2012-10-18 2015-08-26 Dana-Farber Cancer Institute, Inc. Inhibitors of cyclin-dependent kinase 7 (cdk7)
US10000483B2 (en) 2012-10-19 2018-06-19 Dana-Farber Cancer Institute, Inc. Bone marrow on X chromosome kinase (BMX) inhibitors and uses thereof
US9758522B2 (en) 2012-10-19 2017-09-12 Dana-Farber Cancer Institute, Inc. Hydrophobically tagged small molecules as inducers of protein degradation
US10047070B2 (en) 2013-10-18 2018-08-14 Dana-Farber Cancer Institute, Inc. Polycyclic inhibitors of cyclin-dependent kinase 7 (CDK7)
EP3057955B1 (en) 2013-10-18 2018-04-11 Syros Pharmaceuticals, Inc. Heteroaromatic compounds useful for the treatment of prolferative diseases
US10017477B2 (en) 2014-04-23 2018-07-10 Dana-Farber Cancer Institute, Inc. Janus kinase inhibitors and uses thereof
US9862688B2 (en) 2014-04-23 2018-01-09 Dana-Farber Cancer Institute, Inc. Hydrophobically tagged janus kinase inhibitors and uses thereof
HUE056957T2 (en) * 2014-08-29 2022-04-28 Chdi Foundation Inc Probes for imaging huntingtin protein
AU2015308709B2 (en) 2014-08-29 2020-01-02 Chdi Foundation, Inc. Probes for imaging huntingtin protein
ES2705615T3 (en) * 2014-12-02 2019-03-26 Bayer Cropscience Ag Bicyclic compounds as agents to fight pests
AU2015371251B2 (en) 2014-12-23 2020-06-11 Dana-Farber Cancer Institute, Inc. Inhibitors of cyclin-dependent kinase 7 (CDK7)
HK1246645A1 (en) 2015-03-27 2018-09-14 达纳-法伯癌症研究所股份有限公司 Inhibitors of cyclin-dependent kinases
KR101709731B1 (en) * 2015-05-22 2017-02-23 한국과학기술연구원 Benzoxazole or benzothiazole compound, preparation, and use thereof
US10702527B2 (en) 2015-06-12 2020-07-07 Dana-Farber Cancer Institute, Inc. Combination therapy of transcription inhibitors and kinase inhibitors
EP3347018B1 (en) 2015-09-09 2021-09-01 Dana-Farber Cancer Institute, Inc. Inhibitors of cyclin-dependent kinases
NZ746901A (en) 2016-03-11 2023-06-30 Ac Immune Sa Bicyclic compounds for diagnosis and therapy
JP6831802B2 (en) * 2018-01-12 2021-02-17 上海富吉医療器械有限公司Shanghai Chartwell Medical Instrument Co., Ltd. Radionuclide-labeled compound and imaging agent containing it
IL279219B2 (en) 2018-06-08 2024-08-01 Ac Immune Sa New compounds for diagnosis
US12187701B2 (en) 2018-06-25 2025-01-07 Dana-Farber Cancer Institute, Inc. Taire family kinase inhibitors and uses thereof
HU231414B1 (en) 2018-07-13 2023-08-28 Richter Gedeon Nyrt. Thiadiazine derivatives
HU231333B1 (en) 2018-07-13 2023-01-28 Richter Gedeon Nyrt Spirochroman derivatives
HU231478B1 (en) 2018-07-13 2024-02-28 Richter Gedeon Nyrt. Substituted (aza)indole derivatives
JP7660063B2 (en) 2018-12-28 2025-04-10 ダナ-ファーバー キャンサー インスティテュート, インコーポレイテッド Inhibitors of cyclin-dependent kinase 7 and their uses
GB202001181D0 (en) * 2020-01-28 2020-03-11 Globachem Nv Agricultural Chemicals
EP4146653A1 (en) 2020-05-07 2023-03-15 AC Immune SA Novel compounds for diagnosis
EP4430044A1 (en) 2021-11-10 2024-09-18 AC Immune SA Dihydropyrrolo[3,4-c]pyrazole derivatives and their use in diagnosis
JP2024544539A (en) 2021-11-10 2024-12-03 エーシー・イミューン・エス・アー 4H-IMIDAZO[1,5-B]PYRAZOLE DERIVATIVES FOR DIAGNOSIS - Patent application
WO2023083998A1 (en) 2021-11-10 2023-05-19 Ac Immune Sa Dihydropyrrolo[3,4c]-pyrazole derivatives and their use in diagnosis
AR127972A1 (en) 2021-12-17 2024-03-13 Pi Industries Ltd NOVEL FUSED SUBSTITUTED BICYCLIC CARBOXAMIDE PYRIDINE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI
EP4634190A1 (en) 2022-12-16 2025-10-22 AC Immune SA Novel compounds for diagnosis
EP4634191A1 (en) 2022-12-16 2025-10-22 AC Immune SA Novel compounds for diagnosis
WO2025037013A1 (en) 2023-08-16 2025-02-20 Ac Immune Sa Diagnostic compounds that bind to alpha-synuclein

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4038396A (en) * 1975-02-24 1977-07-26 Merck & Co., Inc. Anti-inflammatory oxazole[4,5-b]pyridines
WO2003048137A1 (en) * 2001-11-30 2003-06-12 Merck & Co., Inc. Metabotropic glutamate receptor-5 modulators
WO2007035405A2 (en) * 2005-09-16 2007-03-29 University Of Pittsburgh In-vivo and in-vitro method for detecting amyloid deposits having at least one amyloidogenic protein
WO2007149030A1 (en) * 2006-06-19 2007-12-27 Astrazeneca Ab Novel heteroaryl substituted benzoxazoles
US20080299041A1 (en) * 2007-06-01 2008-12-04 Seoul National University Industry Foundation Heterocyclic indene derivatives and their radioisotope labeled compounds for imaging beta-amyloid deposition

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899506A (en) 1971-07-22 1975-08-12 Merck & Co Inc 4-(Benzoxazol-2-yl)-phenylacetic acids and derivatives thereof
US4131677A (en) * 1975-05-02 1978-12-26 Merck & Co., Inc. Anti-inflammatory oxazolo [5,4-b]pyridines
FR2581067A1 (en) * 1985-04-24 1986-10-31 Centre Nat Rech Scient Process for the preparation of thiazoles condensed with nitrogenous heterocycles and products obtained
WO1997026919A2 (en) 1996-01-24 1997-07-31 Warner-Lambert Company Method of imaging amyloid deposits
PT1334091E (en) 2000-08-24 2013-01-07 Univ Pittsburgh Thioflavin derivatives and their use in diagnosis and therapy of alzheimer`s disease
WO2002085903A2 (en) 2001-04-23 2002-10-31 The Trustees Of The University Of Pennsylvania Amyloid plaque aggregation inhibitors and diagnostic imaging agents
TW200413009A (en) 2002-10-04 2004-08-01 Univ Pennsylvania Biphenyls and fluorenes as imaging agents in alzheimer's disease
CN1774267A (en) 2003-01-22 2006-05-17 综合医院有限公司 Metal chelators that bind amyloid
CA2438032C (en) 2003-03-14 2013-05-07 University Of Pittsburgh Benzothiazole derivative compounds, compositions and uses
EP1799659A1 (en) 2004-10-13 2007-06-27 PTC Therapeutics, Inc. Compounds for nonsense suppression, and methods for their use
EP1893245A4 (en) 2005-06-24 2009-06-24 Univ Pennsylvania RADIOMARQUE PEGYLATION OF LIGANDS FOR USE AS IMAGING AGENTS
WO2007033080A2 (en) 2005-09-12 2007-03-22 Emory University Alzheimer's disease imaging agents
US8334290B2 (en) 2005-10-31 2012-12-18 Merck Sharp & Dohme Corp. CETP inhibitors
WO2007074786A1 (en) 2005-12-26 2007-07-05 Tohoku University Probe for diagnosis of conformational disease
TW200736252A (en) 2006-01-27 2007-10-01 Astrazeneca Ab Novel heteroaryl substituted benzothiazoles
MX2008010187A (en) * 2006-02-10 2008-10-31 Summit Corp Plc Treatment of duchenne muscular dystrophy.
CA2680055A1 (en) 2007-03-06 2008-09-12 Astrazeneca Ab Novel 2-heteroaryl substituted indoles 695
TW200901998A (en) 2007-03-06 2009-01-16 Astrazeneca Ab Novel 2-heteroaryl substituted benzothiophenes and benzofuranes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4038396A (en) * 1975-02-24 1977-07-26 Merck & Co., Inc. Anti-inflammatory oxazole[4,5-b]pyridines
WO2003048137A1 (en) * 2001-11-30 2003-06-12 Merck & Co., Inc. Metabotropic glutamate receptor-5 modulators
WO2007035405A2 (en) * 2005-09-16 2007-03-29 University Of Pittsburgh In-vivo and in-vitro method for detecting amyloid deposits having at least one amyloidogenic protein
WO2007149030A1 (en) * 2006-06-19 2007-12-27 Astrazeneca Ab Novel heteroaryl substituted benzoxazoles
US20080299041A1 (en) * 2007-06-01 2008-12-04 Seoul National University Industry Foundation Heterocyclic indene derivatives and their radioisotope labeled compounds for imaging beta-amyloid deposition

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ALTENHOFF, G. ET AL: "A domino copper-catalysed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles", ADVANCED SYNTHESIS & CATALYSIS, vol. 346, no. 13-15, 2004, pages 1661 - 1664, XP002544096 *
CLARK, R.L. ET AL.: "2-(Substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines as nonacidic antiinflammatory agents", JOURNAL OF MEDICINAL CHEMISTRY, vol. 21, no. 11, 1978, pages 1158 - 1162, XP002543989 *
ISOMURA, Y. ET AL: "Studies on the synthesis and anti-inflammatory activity of 2,6-di-tert-butylphenols with a heterocyclic group at the 4-position", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 31, no. 9, 1983, pages 3168 - 3178, XP002544095 *
ZHUANG ZHI-PING ET AL: "IBOX (2-(4'-dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER, NY, US, vol. 28, no. 8, 1 November 2001 (2001-11-01), pages 887 - 894, XP002386398, ISSN: 0969-8051 *

Also Published As

Publication number Publication date
EP2300481A2 (en) 2011-03-30
US20110085985A1 (en) 2011-04-14
EP2300481B1 (en) 2015-09-30
ES2554772T3 (en) 2015-12-23
AU2009260519A1 (en) 2009-12-23
US8530483B2 (en) 2013-09-10
CA2725940A1 (en) 2009-12-23
JP2011524864A (en) 2011-09-08
WO2009155017A2 (en) 2009-12-23

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