CA3191172A1 - Quinoline cgas antagonist compounds - Google Patents

Quinoline cgas antagonist compounds

Info

Publication number
CA3191172A1
CA3191172A1 CA3191172A CA3191172A CA3191172A1 CA 3191172 A1 CA3191172 A1 CA 3191172A1 CA 3191172 A CA3191172 A CA 3191172A CA 3191172 A CA3191172 A CA 3191172A CA 3191172 A1 CA3191172 A1 CA 3191172A1
Authority
CA
Canada
Prior art keywords
compound
4alkyl
4a1ky1
4co2h
formula
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.)
Pending
Application number
CA3191172A
Other languages
English (en)
French (fr)
Inventor
Jian Qiu
Qi Wei
Matt Tschantz
Heping Shi
Youtong Wu
Huiling TAN
Lijun Sun
Chuo Chen
Zhijian Chen
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.)
University of Texas System
Immunesensor Therapeutics Inc
Original Assignee
University of Texas System
Immunesensor Therapeutics 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 University of Texas System, Immunesensor Therapeutics Inc filed Critical University of Texas System
Publication of CA3191172A1 publication Critical patent/CA3191172A1/en
Pending 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
    • A61K31/435—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
    • A61K31/535—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
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61P25/28—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • 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
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA3191172A 2020-09-03 2021-09-03 Quinoline cgas antagonist compounds Pending CA3191172A1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US202063074446P 2020-09-03 2020-09-03
US63/074,446 2020-09-03
US202063124713P 2020-12-11 2020-12-11
US63/124,713 2020-12-11
US202163196146P 2021-06-02 2021-06-02
US63/196,146 2021-06-02
PCT/US2021/049084 WO2022051634A1 (en) 2020-09-03 2021-09-03 Quinoline cgas antagonist compounds

Publications (1)

Publication Number Publication Date
CA3191172A1 true CA3191172A1 (en) 2022-03-10

Family

ID=78086041

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3191172A Pending CA3191172A1 (en) 2020-09-03 2021-09-03 Quinoline cgas antagonist compounds

Country Status (13)

Country Link
US (3) US11873291B2 (https=)
EP (1) EP4208452A1 (https=)
JP (1) JP2023540081A (https=)
KR (1) KR20230062845A (https=)
CN (1) CN116234802A (https=)
AU (1) AU2021336977A1 (https=)
BR (1) BR112023003948A2 (https=)
CA (1) CA3191172A1 (https=)
IL (1) IL300976A (https=)
MX (1) MX2023002553A (https=)
TW (1) TW202227407A (https=)
WO (1) WO2022051634A1 (https=)
ZA (1) ZA202304064B (https=)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021209473A1 (en) * 2020-04-16 2021-10-21 F. Hoffmann-La Roche Ag Biphenyl derivatives
KR20230062845A (ko) 2020-09-03 2023-05-09 이뮨센서 테라퓨틱스, 인코포레이티드 퀴놀린 cgas 길항제 화합물
WO2022137085A1 (en) 2020-12-22 2022-06-30 Novartis Ag Indole derivatives useful in treating conditions associated with cgas
IL315346A (en) 2022-03-02 2024-11-01 Immunesensor Therapeutics Inc CGAS agonistic quinoline compounds
CN118265696A (zh) * 2022-11-07 2024-06-28 深圳博瑞医药科技有限公司 一种芳基羧酸类化合物及其制备Mrgpr X4抑制剂的用途
WO2024099135A1 (zh) * 2022-11-11 2024-05-16 杭州中美华东制药有限公司 1,5-萘啶类cGAS抑制剂及其用途
AU2024326748A1 (en) 2023-08-18 2026-04-02 Katholieke Universiteit Leuven 1,3-dihydro-2h-pyrrolo[3,4-c]quinoline derivatives as cgas inhibitors for the treatment of inflammatory and/or autoimmune diseases
GB202314609D0 (en) * 2023-09-22 2023-11-08 Univ College Cardiff Consultants Ltd Iminosugar prodrug compounds
WO2025147600A1 (en) * 2024-01-05 2025-07-10 Dewpoint Therapeutics, Inc. Amino quinoline compounds and uses thereof
WO2026057087A1 (zh) * 2024-09-14 2026-03-19 杭州英创医药科技有限公司 作为cGAS抑制剂的化合物

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US3542785A (en) 1967-05-15 1970-11-24 Ciba Geigy Corp 2-hydroxy-4-aryl-quinolines
US3668207A (en) 1970-01-22 1972-06-06 Ciba Geigy Corp 2-amino-4-aryl-quinolines
BR0312204A (pt) 2002-06-27 2005-04-26 Schering Ag Antagonista de receptor ccr5 de quinolina substituìda
WO2009005677A2 (en) * 2007-06-29 2009-01-08 Gilead Sciences, Inc. Antiviral compounds
CA2699697A1 (en) 2007-09-27 2009-04-02 F. Hoffmann-La Roche Ag Quinoline derivatives as 5ht5a receptor antagonists
US20190127354A1 (en) 2015-12-14 2019-05-02 Fundación Para La Investigación Médica Aplicada 2,4,6,7-tetrasubstituted quinoline compounds as inhibitors of dna methyltransferases
CN109111426B (zh) * 2017-06-23 2021-12-14 中国科学院上海药物研究所 一类稠合双环杂芳基或芳基化合物，及其用途
KR20240151869A (ko) * 2017-09-08 2024-10-18 더 보드 어브 트러스티스 어브 더 리랜드 스탠포드 주니어 유니버시티 Enpp1 저해제 및 암의 치료용의 이의 용도
WO2019241787A1 (en) 2018-06-15 2019-12-19 The Regents Of The University Of Colorado A Body Corporate Novel cyclic gmp-amp synthase (cgas) inhibitors and their method of use
PL3829581T3 (pl) * 2018-07-27 2024-07-01 Arcus Biosciences, Inc. Antagoniści pirydonu a2r
EP3620164A1 (en) 2018-09-05 2020-03-11 Genoscience Pharma SAS Substituted 2,4 diamino-quinoline as new medicament for fibrosis, autophagy and cathepsins b (ctsb), l (ctsl) and d (ctsd) related diseases
CA3125626A1 (en) 2019-01-04 2020-07-09 Bellbrook Labs, Llc Inhibitors of cgas activity as therapeutic agents
US11245538B2 (en) * 2019-09-28 2022-02-08 Intel Corporation Methods and apparatus to aggregate telemetry data in an edge environment
AU2021211437A1 (en) 2020-01-20 2022-09-15 Crescenta Biosciences Novel cell metabolism modulating compounds and uses thereof
WO2022010948A1 (en) 2020-07-06 2022-01-13 Crescenta Biosciences Novel cell metabolism modulating compounds and uses thereof for the treatment of viral diseases
KR20230062845A (ko) 2020-09-03 2023-05-09 이뮨센서 테라퓨틱스, 인코포레이티드 퀴놀린 cgas 길항제 화합물
IL315346A (en) 2022-03-02 2024-11-01 Immunesensor Therapeutics Inc CGAS agonistic quinoline compounds

Also Published As

Publication number Publication date
JP2023540081A (ja) 2023-09-21
ZA202304064B (en) 2024-09-25
US20240092760A1 (en) 2024-03-21
US11873291B2 (en) 2024-01-16
KR20230062845A (ko) 2023-05-09
EP4208452A1 (en) 2023-07-12
TW202227407A (zh) 2022-07-16
BR112023003948A2 (pt) 2023-04-11
WO2022051634A1 (en) 2022-03-10
MX2023002553A (es) 2023-05-09
US20230081291A1 (en) 2023-03-16
AU2021336977A1 (en) 2023-03-23
US20250115579A1 (en) 2025-04-10
IL300976A (en) 2023-04-01
US12134609B2 (en) 2024-11-05
CN116234802A (zh) 2023-06-06

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