AU2019417418B2 - (pyridin-2-yl)amine derivatives as ΤGFβR1 (Alk5) inhibitors for the treatment of cancer - Google Patents

(pyridin-2-yl)amine derivatives as ΤGFβR1 (Alk5) inhibitors for the treatment of cancer Download PDF

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Publication number
AU2019417418B2
AU2019417418B2 AU2019417418A AU2019417418A AU2019417418B2 AU 2019417418 B2 AU2019417418 B2 AU 2019417418B2 AU 2019417418 A AU2019417418 A AU 2019417418A AU 2019417418 A AU2019417418 A AU 2019417418A AU 2019417418 B2 AU2019417418 B2 AU 2019417418B2
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compound
mixture
ring
pharmaceutically acceptable
phenyl
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AU2019417418A1 (en
Inventor
Qihui Jin
Tom Yao-Hsiang Wu
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Nexys Therapeutics Inc
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Nexys Therapeutics Inc
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    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2019417418A 2018-12-27 2019-12-17 (pyridin-2-yl)amine derivatives as ΤGFβR1 (Alk5) inhibitors for the treatment of cancer Active AU2019417418B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862785616P 2018-12-27 2018-12-27
US62/785,616 2018-12-27
PCT/US2019/066993 WO2020139636A1 (en) 2018-12-27 2019-12-17 (pyridin-2-yl)amine derivatives as tgf-beta r1 (alk5) inhibitors for the treatment of cancer

Publications (2)

Publication Number Publication Date
AU2019417418A1 AU2019417418A1 (en) 2021-04-15
AU2019417418B2 true AU2019417418B2 (en) 2025-02-27

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AU2019417418A Active AU2019417418B2 (en) 2018-12-27 2019-12-17 (pyridin-2-yl)amine derivatives as ΤGFβR1 (Alk5) inhibitors for the treatment of cancer

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US (2) US12102626B2 (cg-RX-API-DMAC7.html)
EP (1) EP3902796B1 (cg-RX-API-DMAC7.html)
JP (2) JP7515049B2 (cg-RX-API-DMAC7.html)
KR (1) KR102832376B1 (cg-RX-API-DMAC7.html)
CN (1) CN113348167B (cg-RX-API-DMAC7.html)
AR (1) AR117539A1 (cg-RX-API-DMAC7.html)
AU (1) AU2019417418B2 (cg-RX-API-DMAC7.html)
BR (1) BR112021007006A2 (cg-RX-API-DMAC7.html)
CA (1) CA3117838A1 (cg-RX-API-DMAC7.html)
EA (1) EA202191619A1 (cg-RX-API-DMAC7.html)
ES (1) ES2972516T3 (cg-RX-API-DMAC7.html)
IL (1) IL284266B2 (cg-RX-API-DMAC7.html)
MX (1) MX2021007738A (cg-RX-API-DMAC7.html)
SG (1) SG11202103457PA (cg-RX-API-DMAC7.html)
TW (1) TWI884934B (cg-RX-API-DMAC7.html)
WO (1) WO2020139636A1 (cg-RX-API-DMAC7.html)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021216454A1 (en) 2020-04-21 2021-10-28 Lexicon Pharmaceuticals, Inc. 4-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine for use in the the treatment of cov-229e or cov-oc43 coronaviruses infections
JP2023522688A (ja) 2020-04-21 2023-05-31 レクシコン ファーマシューティカルズ インコーポレイテッド ウイルス感染症の治療に使用されるaak1阻害剤
CN113214111A (zh) * 2021-04-30 2021-08-06 上海立科化学科技有限公司 3-(2-氰基苯基)丙酸及4-氰基-1-茚满酮的制备方法
US12263576B2 (en) 2021-08-19 2025-04-01 Hyundai Mobis Co., Ltd. Robot system for automated assembly of modular component
EP4464694A4 (en) * 2022-01-14 2026-04-01 Shanghai Hansoh Biomedical Co Ltd POLYCYCLIC DERIVATIVE CONTAINING PYRIDINE, ITS PREPARATION PROCESS AND ITS USE
CN121554469B (zh) * 2026-01-23 2026-04-17 四川大学华西医院 一种alk5 protac化合物及其应用

Citations (2)

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WO2009022171A1 (en) * 2007-08-13 2009-02-19 Astrazeneca Ab Pyridinyiioxy pyridines as alk5 inhibitors
WO2016057278A1 (en) * 2014-10-07 2016-04-14 Eli Lilly And Company Aminopyridyloxypyrazole compounds

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SI1397364T1 (sl) 2001-05-24 2007-12-31 Lilly Co Eli Novi pirolni derivati kot farmacevtske uäśinkovine
UA80571C2 (en) 2002-11-22 2007-10-10 Lilly Co Eli Quinolinyl-pyrrolopyrazoles
TW200538120A (en) 2004-02-20 2005-12-01 Kirin Brewery Compound having TGF-beta inhibitory activity and pharmaceutical composition containing same
US8080568B1 (en) 2010-06-29 2011-12-20 Ewha University - Industry Collaboration Foundation 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors
US20140296248A1 (en) 2011-04-04 2014-10-02 Stichting het Nederlands Kanker Instiuut-Antoni van Leeuwenhoek ziekenhuis Methods and compositions for predicting resistance to anticancer treatment
WO2012151137A1 (en) * 2011-05-04 2012-11-08 Merck Sharp & Dohme Corp. Amino-pyridine-containing spleen tyrosine kinase (syk) inhibitors
WO2014048065A1 (en) * 2012-09-28 2014-04-03 Merck Sharp & Dohme Corp. Triazolyl derivatives as syk inhibitors
EP2934525B1 (en) * 2012-12-21 2019-05-08 Merck Sharp & Dohme Corp. Thiazole-substituted aminopyridines as spleen tyrosine kinase inhibitors
WO2014155300A2 (en) * 2013-03-28 2014-10-02 Aurigene Discovery Technologies Limited Substitued pyrimidine amine derivatives as tak-1 inhibitors
PL3089971T3 (pl) * 2014-01-01 2021-01-25 Medivation Technologies Llc Związki i sposoby ich zastosowania
JP6767875B2 (ja) 2014-04-08 2020-10-14 ライジェル ファーマシューティカルズ, インコーポレイテッド Tgf−ベータ阻害剤としての2,3−二置換ピリジン化合物および使用方法
CA2986441A1 (en) * 2015-06-12 2016-12-15 Dana-Farber Cancer Institute, Inc. Combination therapy of transcription inhibitors and kinase inhibitors
CN108026105B (zh) 2015-07-23 2020-10-16 百时美施贵宝公司 TGFβ受体拮抗剂
WO2020103817A1 (zh) 2018-11-20 2020-05-28 南京圣和药业股份有限公司 TGF-βR1抑制剂及其应用
KR102816656B1 (ko) 2019-06-25 2025-06-02 인벤티스바이오 컴퍼니 리미티드 헤테로고리 화합물, 이의 제조방법 및 이의 사용방법
CN112707902B (zh) 2020-03-23 2022-04-15 杭州阿诺生物医药科技有限公司 TGF-β受体抑制剂

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WO2009022171A1 (en) * 2007-08-13 2009-02-19 Astrazeneca Ab Pyridinyiioxy pyridines as alk5 inhibitors
WO2016057278A1 (en) * 2014-10-07 2016-04-14 Eli Lilly And Company Aminopyridyloxypyrazole compounds

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Publication number Publication date
CN113348167A (zh) 2021-09-03
TW202039436A (zh) 2020-11-01
IL284266B1 (en) 2024-02-01
AR117539A1 (es) 2021-08-11
BR112021007006A2 (pt) 2021-08-10
IL284266B2 (en) 2024-06-01
KR20210110316A (ko) 2021-09-07
WO2020139636A1 (en) 2020-07-02
TWI884934B (zh) 2025-06-01
AU2019417418A1 (en) 2021-04-15
EP3902796A1 (en) 2021-11-03
CN113348167B (zh) 2026-01-09
KR102832376B1 (ko) 2025-07-09
NZ775362A (en) 2025-02-28
US20240398776A1 (en) 2024-12-05
EA202191619A1 (ru) 2021-09-28
IL284266A (en) 2021-08-31
CA3117838A1 (en) 2020-07-02
EP3902796C0 (en) 2024-02-07
ES2972516T3 (es) 2024-06-13
US12102626B2 (en) 2024-10-01
JP2022517730A (ja) 2022-03-10
EP3902796B1 (en) 2024-02-07
SG11202103457PA (en) 2021-05-28
JP2023052437A (ja) 2023-04-11
JP7515049B2 (ja) 2024-07-12
MX2021007738A (es) 2021-08-05
US20220054465A1 (en) 2022-02-24

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Date Code Title Description
DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE INVENTION TITLE TO READ (PYRIDIN-2-YL)AMINE DERIVATIVES AS GFSSR1 (ALK5) INHIBITORS FOR THE TREATMENT OF CANCER

FGA Letters patent sealed or granted (standard patent)