CA2722131A1 - Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors - Google Patents

Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors Download PDF

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Publication number
CA2722131A1
CA2722131A1 CA2722131A CA2722131A CA2722131A1 CA 2722131 A1 CA2722131 A1 CA 2722131A1 CA 2722131 A CA2722131 A CA 2722131A CA 2722131 A CA2722131 A CA 2722131A CA 2722131 A1 CA2722131 A1 CA 2722131A1
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CA
Canada
Prior art keywords
alkyl
pyridin
imidazo
alkoxy
ylamino
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.)
Abandoned
Application number
CA2722131A
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English (en)
French (fr)
Inventor
Catherine Leblanc
Cathy Ritchie
Duncan Shaw
Nikolaus Johannes Stiefl
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Novartis AG
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Novartis AG
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Filing date
Publication date
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Publication of CA2722131A1 publication Critical patent/CA2722131A1/en
Abandoned legal-status Critical Current

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    • 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
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/16—Central respiratory analeptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A—HUMAN NECESSITIES
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    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Pulmonology (AREA)
  • Virology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Molecular Biology (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Hematology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Biotechnology (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Vascular Medicine (AREA)
  • Immunology (AREA)
CA2722131A 2008-04-29 2009-04-27 Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors Abandoned CA2722131A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08155405 2008-04-29
EP08155405.7 2008-04-29
PCT/EP2009/055066 WO2009133070A1 (en) 2008-04-29 2009-04-27 Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors

Publications (1)

Publication Number Publication Date
CA2722131A1 true CA2722131A1 (en) 2009-11-05

Family

ID=40043988

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2722131A Abandoned CA2722131A1 (en) 2008-04-29 2009-04-27 Imidazo-pyridine derivatives as activin-like receptor kinase (alk4 or alk5) inhibitors

Country Status (14)

Country Link
US (1) US9079897B2 (https=)
EP (1) EP2307402B1 (https=)
JP (1) JP5507543B2 (https=)
KR (1) KR20100130226A (https=)
CN (1) CN102015691B (https=)
AU (1) AU2009242145B2 (https=)
BR (1) BRPI0911490A2 (https=)
CA (1) CA2722131A1 (https=)
EA (1) EA201001687A1 (https=)
ES (1) ES2399175T3 (https=)
MX (1) MX2010011867A (https=)
PL (1) PL2307402T3 (https=)
PT (1) PT2307402E (https=)
WO (1) WO2009133070A1 (https=)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2010344973B2 (en) 2010-02-05 2016-06-16 Merck Patent Gmbh Hetaryl-[1,8]naphthyridine derivatives
ES2528441T3 (es) 2010-02-22 2015-02-10 Merck Patent Gmbh Hetarilaminonaftiridinas
US9073918B2 (en) 2010-05-20 2015-07-07 Takeda Pharmaceutical Company Limited Pyrazolo[4,3-b]pyridine-7-amine inhibitors of ALK5
US8871744B2 (en) 2010-07-21 2014-10-28 B & G Partyers, LLC Compounds and methods for selectively targeting tumor-associated mucins
CN103328535B (zh) 2010-11-08 2016-01-20 Sk化学株式会社 聚乳酸树脂、其制备方法以及包含所述聚乳酸树脂的包装膜
WO2012138223A2 (en) * 2011-04-05 2012-10-11 Academisch Ziekenhuis Leiden H.O.D.N. Lumc Compounds and methods for altering activin receptor-like kinase signalling
JP2016510764A (ja) 2013-03-07 2016-04-11 カリフィア バイオ, インク.Califia Bio, Inc. 混合系キナーゼ阻害剤および治療法
CN107531697A (zh) * 2015-04-16 2018-01-02 默克专利股份公司 3‑(1h‑苯并咪唑‑2‑基)‑1h‑吡啶‑2‑酮衍生物
WO2017053657A1 (en) * 2015-09-23 2017-03-30 Dana-Farber Cancer Institute, Inc. Inhibitors of alk and srpk and methods of use
RU2642456C2 (ru) * 2016-06-29 2018-01-25 Федеральное государственное бюджетное образовательное учреждение высшего образования "Ярославский государственный университет им. П.Г. Демидова" Способ получения N-арилзамещенных 3H-имидазо[4,5-b]пиридинов
EP3492461B1 (en) 2016-07-29 2024-10-23 Shanghai Yingli Pharmaceutical Co. Ltd. Nitrogenous heterocyclic aromatic compound, preparation method therefor, pharmaceutical composition thereof, and application thereof
CN106831770A (zh) * 2017-03-13 2017-06-13 牡丹江医学院 一种药物组合物及其用于治疗肝硬化的用途
CN110066277B (zh) 2018-01-24 2021-07-23 上海璎黎药业有限公司 芳香杂环取代烯烃化合物、其制备方法、药物组合物和应用
CN110066276B (zh) 2018-01-24 2020-09-18 上海璎黎药业有限公司 芳香杂环化合物、其中间体、制备方法、药物组合物和应用
US20200247812A1 (en) * 2018-07-10 2020-08-06 Integral Biosciences Private Limited Heterocyclic compounds and methods of use
JP7640458B2 (ja) 2018-10-05 2025-03-05 アンナプルナ バイオ インコーポレイテッド Ａｐｊ受容体活性に関連する状態を処置するための化合物および組成物
AU2021205893A1 (en) 2020-01-08 2022-06-23 Synthis Therapeutics, Inc. ALK5 inhibitor conjugates and uses thereof
EP4142769A4 (en) 2020-04-28 2024-05-15 Acceleron Pharma Inc. ACTRII PROTEINS AND USE IN THE TREATMENT OF POSTCAPILLARY PULMONARY HYPERTENSION
KR20230041003A (ko) 2020-07-15 2023-03-23 키에시 파르마슈티시 엣스. 피. 에이. Alk5 억제제로서 피리도 옥사진 아미노 유도체
ES2982017T3 (es) 2020-07-15 2024-10-14 Chiesi Farm Spa Derivados de pirido-oxazina como inhibidores de ALK5
PT4182308T (pt) 2020-07-15 2024-12-04 Chiesi Farm Spa Derivados de piridazinil amino como inibidores de alk5
US20240116948A1 (en) 2020-12-23 2024-04-11 Chiesi Farmaceutici S.P.A. Pyrido oxazine derivatives as alk5 inhibitors
AU2022351219A1 (en) 2021-09-21 2024-05-02 Chiesi Farmaceutici S.P.A. Pyridazinyl amino derivatives as alk5 inhibitors
US20250270215A1 (en) 2022-04-27 2025-08-28 Chiesi Farmaceutici S.P.A. Imidazole derivatives as alk5 inhibitors
CN121712526A (zh) 2023-06-13 2026-03-20 辛瑟斯治疗股份有限公司 抗cd5抗体及其用途

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK40192D0 (da) * 1992-03-26 1992-03-26 Neurosearch As Imidazolforbindelser, deres fremstilling og anvendelse
GB9921150D0 (en) * 1999-09-07 1999-11-10 Merck Sharp & Dohme Therapeutic agents
GB0217783D0 (en) 2002-07-31 2002-09-11 Glaxo Group Ltd Compounds
WO2005023246A1 (en) * 2003-09-04 2005-03-17 Aventis Pharmaceuticals Inc. Substituted indoles as inhibitors of poly (adp-ribose) polymerase (parp)
CA2576765C (en) * 2004-09-03 2013-05-28 Applied Research Systems Ars Holding N.V. Pyridine methylene azolidinones and use thereof phosphoinositide inhibitors
BRPI0714409A2 (pt) * 2006-07-14 2013-03-12 Novartis Ag derivados de pirimidina como inibidores de alk-5
CN101522682A (zh) * 2006-10-30 2009-09-02 诺瓦提斯公司 作为抗炎剂的杂环化合物

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Publication number Publication date
EP2307402A1 (en) 2011-04-13
US9079897B2 (en) 2015-07-14
EP2307402B1 (en) 2012-11-07
ES2399175T3 (es) 2013-03-26
JP5507543B2 (ja) 2014-05-28
AU2009242145B2 (en) 2012-07-05
WO2009133070A1 (en) 2009-11-05
CN102015691B (zh) 2014-01-08
AU2009242145A1 (en) 2009-11-05
PT2307402E (pt) 2013-02-15
EA201001687A1 (ru) 2011-06-30
CN102015691A (zh) 2011-04-13
BRPI0911490A2 (pt) 2016-01-05
MX2010011867A (es) 2010-11-26
JP2011518856A (ja) 2011-06-30
US20110060004A1 (en) 2011-03-10
KR20100130226A (ko) 2010-12-10
PL2307402T3 (pl) 2013-05-31

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