KR102833588B1 - 무스카린성 m1 및/또는 m4 수용체의 작용제로서의 옥사디아졸 - Google Patents

무스카린성 m1 및/또는 m4 수용체의 작용제로서의 옥사디아졸

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Publication number
KR102833588B1
KR102833588B1 KR1020217001748A KR20217001748A KR102833588B1 KR 102833588 B1 KR102833588 B1 KR 102833588B1 KR 1020217001748 A KR1020217001748 A KR 1020217001748A KR 20217001748 A KR20217001748 A KR 20217001748A KR 102833588 B1 KR102833588 B1 KR 102833588B1
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Prior art keywords
methyl
oxadiazol
azabicyclo
octan
diazaspiro
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KR20210024036A (ko
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길스 앨버트 브라운
배리 존 테오발드
벤자민 제랄드 테한
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넥세라 파마 유케이 리미티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
    • 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
    • C07D471/08—Bridged systems
    • 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
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic 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
    • C07D498/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic 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
    • C07D498/10—Spiro-condensed systems
    • 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
    • C07B2200/07—Optical isomers
    • 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
    • C07B2200/09—Geometrical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
KR1020217001748A 2018-06-22 2019-06-24 무스카린성 m1 및/또는 m4 수용체의 작용제로서의 옥사디아졸 Active KR102833588B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1810245.9 2018-06-22
GBGB1810245.9A GB201810245D0 (en) 2018-06-22 2018-06-22 Pharmaceutical compounds
PCT/GB2019/051778 WO2019243850A1 (en) 2018-06-22 2019-06-24 Oxadiazoles as agonists of the muscarinic m1 and/or m4 receptor

Publications (2)

Publication Number Publication Date
KR20210024036A KR20210024036A (ko) 2021-03-04
KR102833588B1 true KR102833588B1 (ko) 2025-07-16

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KR1020217001748A Active KR102833588B1 (ko) 2018-06-22 2019-06-24 무스카린성 m1 및/또는 m4 수용체의 작용제로서의 옥사디아졸

Country Status (14)

Country Link
US (2) US10858352B2 (enExample)
EP (1) EP3810607A1 (enExample)
JP (3) JP7389762B2 (enExample)
KR (1) KR102833588B1 (enExample)
CN (2) CN119039284A (enExample)
AU (1) AU2019289216B2 (enExample)
BR (1) BR112020026437A2 (enExample)
CA (1) CA3104085A1 (enExample)
GB (1) GB201810245D0 (enExample)
MX (1) MX2020014156A (enExample)
SG (1) SG11202012570TA (enExample)
TW (1) TWI872024B (enExample)
WO (1) WO2019243850A1 (enExample)
ZA (1) ZA202007986B (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2619829T3 (es) 2011-11-18 2017-06-27 Heptares Therapeutics Limited Agonistas del receptor muscarínico M1
GB201404922D0 (en) 2014-03-19 2014-04-30 Heptares Therapeutics Ltd Pharmaceutical compounds
GB201513743D0 (en) 2015-08-03 2015-09-16 Heptares Therapeutics Ltd Muscarinic agonists
GB201519352D0 (en) 2015-11-02 2015-12-16 Heptares Therapeutics Ltd Pharmaceutical compounds
GB201617454D0 (en) 2016-10-14 2016-11-30 Heptares Therapeutics Limited Pharmaceutical compounds
GB201810245D0 (en) 2018-06-22 2018-08-08 Heptares Therapeutics Ltd Pharmaceutical compounds
GB201810239D0 (en) 2018-06-22 2018-08-08 Heptares Therapeutics Ltd Pharmaceutical compounds
GB201819961D0 (en) 2018-12-07 2019-01-23 Heptares Therapeutics Ltd Pharmaceutical compounds
GB201819960D0 (en) 2018-12-07 2019-01-23 Heptares Therapeutics Ltd Pharmaceutical compounds
GB202020191D0 (en) * 2020-12-18 2021-02-03 Heptares Therapeutics Ltd Pharmaceutical compounds
PH12022550860A1 (en) 2019-10-09 2023-06-14 Novartis Ag 5-oxa-2-azaspiro[3.4]octane derivatives as m4 agonists
UY38906A (es) 2019-10-09 2021-05-31 Novartis Ag Compuestos 2- derivados de azaspiro[3,4]octano como agonistas de m4 y composiciones de los mismos

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017021730A1 (en) 2015-08-03 2017-02-09 Heptares Therapeutics Limited Muscarinic agonists
WO2018069732A1 (en) 2016-10-14 2018-04-19 Heptares Therapeutics Limited Heterocyclic compounds having activity as modulators of muscarinic m1 and/or m4 receptors in the treatment of cns diseases and pains.

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AU2307899A (en) * 1997-12-23 1999-07-12 Alcon Laboratories, Inc. Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions
US7786141B2 (en) 2004-08-19 2010-08-31 Vertex Pharmaceuticals Incorporated Dihydrospiroindene modulators of muscarinic receptors
CA2634456A1 (en) 2005-12-22 2007-07-05 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors
RU2008137583A (ru) 2006-02-22 2010-03-27 Вертекс Фармасьютикалз Инкорпорейшн (Us) Спиропиперидины в качестве модуляторов мускариновых рецепторов
CN101553231A (zh) 2006-08-15 2009-10-07 弗特克斯药品有限公司 毒蕈碱受体调节剂
WO2008117229A1 (en) * 2007-03-23 2008-10-02 Ranbaxy Laboratories Limited Muscarinic receptor antagonists
CN103221046A (zh) * 2010-09-17 2013-07-24 阵列生物制药公司 作为gpr119调节剂的哌啶基取代的内酰胺
EP2897948B1 (en) * 2012-09-18 2016-08-31 Heptares Therapeutics Limited Bicyclic aza compounds as muscarinic m1 receptor agonists
US9593106B2 (en) * 2013-02-07 2017-03-14 Heptares Therapeutics Limited Piperidin-1-yl and azepin-1-yl carboxylates as muscarinic M4 receptor agonists
RU2685230C2 (ru) * 2014-02-06 2019-04-17 Хептарес Терапьютикс Лимитед Бициклические азотсодержащие соединения как агонисты М1 мускариновых рецепторов
GB201404922D0 (en) * 2014-03-19 2014-04-30 Heptares Therapeutics Ltd Pharmaceutical compounds
GB201513743D0 (en) * 2015-08-03 2015-09-16 Heptares Therapeutics Ltd Muscarinic agonists
GB201810245D0 (en) * 2018-06-22 2018-08-08 Heptares Therapeutics Ltd Pharmaceutical compounds

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
WO2017021730A1 (en) 2015-08-03 2017-02-09 Heptares Therapeutics Limited Muscarinic agonists
WO2018069732A1 (en) 2016-10-14 2018-04-19 Heptares Therapeutics Limited Heterocyclic compounds having activity as modulators of muscarinic m1 and/or m4 receptors in the treatment of cns diseases and pains.

Also Published As

Publication number Publication date
ZA202007986B (en) 2021-10-27
WO2019243850A1 (en) 2019-12-26
US10858352B2 (en) 2020-12-08
MX2020014156A (es) 2021-03-09
CA3104085A1 (en) 2019-12-26
JP7389762B2 (ja) 2023-11-30
JP2026002915A (ja) 2026-01-08
CN112585135B (zh) 2024-08-02
TWI872024B (zh) 2025-02-11
US20210101893A1 (en) 2021-04-08
AU2019289216B2 (en) 2023-04-06
KR20210024036A (ko) 2021-03-04
EP3810607A1 (en) 2021-04-28
TW202019918A (zh) 2020-06-01
BR112020026437A2 (pt) 2021-03-23
GB201810245D0 (en) 2018-08-08
AU2019289216A1 (en) 2021-01-14
JP2021528447A (ja) 2021-10-21
SG11202012570TA (en) 2021-01-28
US11319312B2 (en) 2022-05-03
CN112585135A (zh) 2021-03-30
US20190389849A1 (en) 2019-12-26
JP2023164721A (ja) 2023-11-10
CN119039284A (zh) 2024-11-29

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