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WO2024141660A3 - Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases - Google Patents

Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases Download PDF

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Publication number
WO2024141660A3
WO2024141660A3 PCT/EP2023/088020 EP2023088020W WO2024141660A3 WO 2024141660 A3 WO2024141660 A3 WO 2024141660A3 EP 2023088020 W EP2023088020 W EP 2023088020W WO 2024141660 A3 WO2024141660 A3 WO 2024141660A3
Authority
WO
WIPO (PCT)
Prior art keywords
benzothiazine
quinazoline
dihydro
benzoxazine derivatives
treating
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/EP2023/088020
Other languages
French (fr)
Other versions
WO2024141660A2 (en
Inventor
Eric Konofal
Anh Tuan Lormier
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.)
Aexon Labs Inc
Original Assignee
Aexon Labs 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 Aexon Labs Inc filed Critical Aexon Labs Inc
Priority to EP23841600.2A priority Critical patent/EP4642460A2/en
Priority to CN202380094819.6A priority patent/CN121127244A/en
Publication of WO2024141660A2 publication Critical patent/WO2024141660A2/en
Publication of WO2024141660A3 publication Critical patent/WO2024141660A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/536—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with carbocyclic ring 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
    • C07D265/22—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
    • C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Psychiatry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention is directed to dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives for use in the prevention or treatment of neurological, psychiatric, sleep disorders and diseases, advantageously in which central orexin neurotransmission is compromised or in which central and peripheral orexin receptors are involved. The present invention is also directed to pharmaceutical compositions comprising these compounds for use in the prevention and/or treatment of neurological disorders and diseases. The present invention is also directed to dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and the use of these compounds as a medicament.
PCT/EP2023/088020 2022-12-30 2023-12-29 Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases Ceased WO2024141660A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP23841600.2A EP4642460A2 (en) 2022-12-30 2023-12-29 Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases
CN202380094819.6A CN121127244A (en) 2022-12-30 2023-12-29 Dihydroquinazoline, dihydrobenzothiazide, and dihydrobenzoxazine derivatives, and their uses as orexin receptor agonists for the treatment or prevention of neurological disorders.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22307075 2022-12-30
EP22307075.6 2022-12-30

Publications (2)

Publication Number Publication Date
WO2024141660A2 WO2024141660A2 (en) 2024-07-04
WO2024141660A3 true WO2024141660A3 (en) 2024-08-29

Family

ID=85018905

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/EP2023/088020 Ceased WO2024141660A2 (en) 2022-12-30 2023-12-29 Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases
PCT/EP2023/088019 Ceased WO2024115797A2 (en) 2022-12-30 2023-12-29 Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP2023/088019 Ceased WO2024115797A2 (en) 2022-12-30 2023-12-29 Dihydro-quinazoline, -benzothiazine and -benzoxazine derivatives and use thereof as orexin receptors agonists for treating or preventing neurological diseases

Country Status (3)

Country Link
EP (2) EP4642459A2 (en)
CN (2) CN121127244A (en)
WO (2) WO2024141660A2 (en)

Citations (10)

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US2943087A (en) * 1960-06-28 n naoh
WO1999042456A2 (en) * 1998-02-18 1999-08-26 Neurosearch A/S Novel compounds and their use as positive ampa receptor modulators
WO2005117876A1 (en) * 2004-06-01 2005-12-15 University Of Virginia Patent Foundation Dual small molecule inhibitors of cancer and angiogenesis
US20130005666A1 (en) * 2011-06-29 2013-01-03 Cornell University Reporter system for high throughput screening of compounds and uses thereof
WO2015154047A1 (en) * 2014-04-03 2015-10-08 Restorgenex Corporation Novel methods
WO2016201257A2 (en) * 2015-06-10 2016-12-15 The Johns Hopkins University Compositions and methods for identifying adp-ribosylated sites by mass spectrometry
WO2017167989A1 (en) * 2016-03-31 2017-10-05 Centre National De La Recherche Scientifique Cytidine deaminase expression level in cancer as a new therapeutic target
WO2018044136A1 (en) * 2016-09-05 2018-03-08 충남대학교 산학협력단 Novel compound, preparation method therefor and pharmaceutical composition containing same as active ingredient for preventing or treating diseases associated with poly(adp-ribose) polymerase-1 (parp-1)
CN111635369A (en) * 2020-06-19 2020-09-08 宁夏大学 A kind of preparation method of dihydroquinazolinone derivative
CN116178283A (en) * 2023-01-18 2023-05-30 武汉科技大学 2-Phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives and their preparation and application

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CR20220310A (en) 2019-11-27 2022-09-23 Sumitomo Pharma Co Ltd CYCLOALKYLUREA DERIVATIVE
US11760747B2 (en) 2020-12-21 2023-09-19 Alkermes, Inc. Substituted piperidino compounds and related methods of treatment

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2943087A (en) * 1960-06-28 n naoh
WO1999042456A2 (en) * 1998-02-18 1999-08-26 Neurosearch A/S Novel compounds and their use as positive ampa receptor modulators
WO2005117876A1 (en) * 2004-06-01 2005-12-15 University Of Virginia Patent Foundation Dual small molecule inhibitors of cancer and angiogenesis
US20130005666A1 (en) * 2011-06-29 2013-01-03 Cornell University Reporter system for high throughput screening of compounds and uses thereof
WO2015154047A1 (en) * 2014-04-03 2015-10-08 Restorgenex Corporation Novel methods
WO2016201257A2 (en) * 2015-06-10 2016-12-15 The Johns Hopkins University Compositions and methods for identifying adp-ribosylated sites by mass spectrometry
WO2017167989A1 (en) * 2016-03-31 2017-10-05 Centre National De La Recherche Scientifique Cytidine deaminase expression level in cancer as a new therapeutic target
WO2018044136A1 (en) * 2016-09-05 2018-03-08 충남대학교 산학협력단 Novel compound, preparation method therefor and pharmaceutical composition containing same as active ingredient for preventing or treating diseases associated with poly(adp-ribose) polymerase-1 (parp-1)
CN111635369A (en) * 2020-06-19 2020-09-08 宁夏大学 A kind of preparation method of dihydroquinazolinone derivative
CN116178283A (en) * 2023-01-18 2023-05-30 武汉科技大学 2-Phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives and their preparation and application

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
COX SARAH J. ET AL: "High-Throughput Screening at the Membrane Interface Reveals Inhibitors of Amyloid-[beta]", BIOCHEMISTRY, vol. 59, no. 24, 29 May 2020 (2020-05-29), pages 2249 - 2258, XP093050043, ISSN: 0006-2960, DOI: 10.1021/acs.biochem.0c00328 *
CUI LI-JING ET AL: "Synthesis and Anticonvulsant Activity Evaluation of 2-Phenyl-2H-benzo[e][1,3]oxazin-4(3H)-ones", ASIAN JOURNAL OF CHEMISTRY, vol. 26, no. 9, 29 April 2014 (2014-04-29), IN, pages 2553 - 2556, XP093186107, ISSN: 0970-7077, DOI: 10.14233/ajchem.2014.15725 *
DATABASE CAPLUS [online] Chemical Abstract Service, Columbus, Ohio, US; 1 January 1969 (1969-01-01), COVELLO MARIO ET AL: "New iodoorganic compounds. Iodinated 2,3-dihydro-4H-1,3-benzoxazin-4-ones", XP093186488, retrieved from https://stn.org/stn/# Database accession no. 1970:3446 *
DATABASE CAPLUS [online] Chemical Abstract Service, Columbus, Ohio, US; 1 January 1985 (1985-01-01), SHUKLA J. S. ET AL: "Synthesis of 6,8-disubstituted 2-methyl/phenyl-3-[4-(3-phthalimidoacetamido/propionamido)]phenylquinazolin-4-ones as anthelmintic agents", XP093186485, retrieved from https://stn.org/stn/# Database accession no. 1986:81557 *
DATABASE CAPLUS [online] Chemical Abstract Service, Columbus, Ohio, US; 1 January 2007 (2007-01-01), KIDWAI MAZAAHIR ET AL: "One-pot heterocondensation for benzoxazinone derivatives using sodiumperborate as catalyst", XP093186481, retrieved from https://stn.org/stn/# Database accession no. 2007:751054 *
EVANS REBECCA: "Orexin 2 receptor-selective agonist danavorexton improves narcolepsy phenotype in a mouse model and in human patients", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES, vol. 119, no. 35, 22 August 2022 (2022-08-22), pages 1 - 10, XP093050145, Retrieved from the Internet <URL:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9436334/pdf/pnas.202207531.pdf> DOI: 10.1073/pnas.2207531119 *
FLORIAN RÖRSCH ET AL: "Structure-Activity Relationship of Nonacidic Quinazolinone Inhibitors of Human Microsomal Prostaglandin Synthase 1 (mPGES 1)", JOURNAL OF MEDICINAL CHEMISTRY, vol. 55, no. 8, 26 April 2012 (2012-04-26), pages 3792 - 3803, XP055116286, ISSN: 0022-2623, DOI: 10.1021/jm201687d *
GARY M. CHINIGO ET AL: "Asymmetric Synthesis of 2,3-Dihydro-2-arylquinazolin-4-ones: Methodology and Application to a Potent Fluorescent Tubulin Inhibitor with Anticancer Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 15, 1 August 2008 (2008-08-01), US, pages 4620 - 4631, XP055658845, ISSN: 0022-2623, DOI: 10.1021/jm800271c *
P. ANDREWS STEPHEN ET AL: "Orexin Receptor Antagonists: Historical Perspectives and Future Opportunities", CURRENT TOPICS IN MEDICINAL CHEMISTRY, vol. 16, no. 29, 20 October 2016 (2016-10-20), NL, pages 3438 - 3469, XP055958442, ISSN: 1568-0266, DOI: 10.2174/1568026616666150929111607 *
YALE HARRY L: "Substituted 2,3-dihydro-4(1H)-quinazolinones. A new class of inhibitors of cell multiplication", JOURNAL OF MEDICINAL CHEMISTRY, 1 May 1967 (1967-05-01), pages 1 - 3, XP093049795, Retrieved from the Internet <URL:https://pubs.acs.org/doi/pdf/10.1021/jm00315a010> [retrieved on 20230525] *

Also Published As

Publication number Publication date
CN120981232A (en) 2025-11-18
EP4642459A2 (en) 2025-11-05
WO2024141660A2 (en) 2024-07-04
WO2024115797A2 (en) 2024-06-06
CN121127244A (en) 2025-12-12
WO2024115797A3 (en) 2024-09-06
EP4642460A2 (en) 2025-11-05

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