CA2501322C - Quinolinyl-pyrrolopyrazoles - Google Patents

Quinolinyl-pyrrolopyrazoles Download PDF

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Publication number
CA2501322C
CA2501322C CA2501322A CA2501322A CA2501322C CA 2501322 C CA2501322 C CA 2501322C CA 2501322 A CA2501322 A CA 2501322A CA 2501322 A CA2501322 A CA 2501322A CA 2501322 C CA2501322 C CA 2501322C
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CA
Canada
Prior art keywords
tgf
cancer
cell
pyridin
tumor
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.)
Expired - Fee Related
Application number
CA2501322A
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English (en)
French (fr)
Other versions
CA2501322A1 (en
Inventor
Douglas Wade Beight
Jason Scott Sawyer
Jonathan Michael Yingling
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.)
Eli Lilly and Co
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Eli Lilly and Co
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Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of CA2501322A1 publication Critical patent/CA2501322A1/en
Application granted granted Critical
Publication of CA2501322C publication Critical patent/CA2501322C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • 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
    • C07D487/04—Ortho-condensed 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4162—1,2-Diazoles condensed with heterocyclic 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
    • A61K31/435—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
    • 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
    • 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
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • 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
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • 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
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Neurology (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pulmonology (AREA)
  • Urology & Nephrology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Psychiatry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • AIDS & HIV (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2501322A 2002-11-22 2003-11-10 Quinolinyl-pyrrolopyrazoles Expired - Fee Related CA2501322C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US42889302P 2002-11-22 2002-11-22
US60/428,893 2002-11-22
PCT/US2003/032747 WO2004048382A1 (en) 2002-11-22 2003-11-10 Quinolinyl-pyrrolopyrazoles

Publications (2)

Publication Number Publication Date
CA2501322A1 CA2501322A1 (en) 2004-06-10
CA2501322C true CA2501322C (en) 2011-05-10

Family

ID=32393478

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2501322A Expired - Fee Related CA2501322C (en) 2002-11-22 2003-11-10 Quinolinyl-pyrrolopyrazoles

Country Status (28)

Country Link
US (2) US7265225B2 (enExample)
EP (1) EP1565471B1 (enExample)
JP (1) JP4542906B2 (enExample)
KR (1) KR101057282B1 (enExample)
CN (1) CN100345852C (enExample)
AT (1) ATE341550T1 (enExample)
AU (1) AU2003291643B2 (enExample)
BR (1) BR0315337A (enExample)
CA (1) CA2501322C (enExample)
CO (1) CO5570677A2 (enExample)
CR (1) CR7830A (enExample)
CY (1) CY1106283T1 (enExample)
DE (1) DE60308893T2 (enExample)
DK (1) DK1565471T3 (enExample)
EA (1) EA008387B1 (enExample)
EC (1) ECSP055807A (enExample)
EG (1) EG25822A (enExample)
ES (1) ES2273046T3 (enExample)
HR (1) HRP20050436B1 (enExample)
IL (1) IL168190A (enExample)
MX (1) MXPA05005432A (enExample)
NO (1) NO331403B1 (enExample)
NZ (1) NZ538942A (enExample)
PL (1) PL227840B1 (enExample)
PT (1) PT1565471E (enExample)
UA (1) UA80571C2 (enExample)
WO (1) WO2004048382A1 (enExample)
ZA (1) ZA200503121B (enExample)

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AR039241A1 (es) 2002-04-04 2005-02-16 Biogen Inc Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos
US7405299B2 (en) * 2002-11-27 2008-07-29 Eli Lilly And Company Compounds as pharmaceutical agents
CA2616196C (en) * 2005-07-22 2012-08-21 Eli Lilly And Company A pyridin quinolin substituted pyrrolo [1,2-b] pyrazole monohydrate as tgf-beta inhibitor
WO2007039151A1 (en) * 2005-09-28 2007-04-12 Universität Zürich Blockers of transforming growth factor beta and its receptors for the treatment of infectious diseases
CN101553254A (zh) 2006-10-03 2009-10-07 建新公司 TGF-β拮抗物治疗具有罹患支气管肺发育不良风险的婴儿的用途
EP2527345B1 (en) * 2006-10-16 2015-12-16 Thesan Pharmaceuticals, Inc. Therapeutic pyrazolyl thienopyridines
CN103140474A (zh) 2010-07-02 2013-06-05 吉里德科学公司 治疗aids的萘-2-基乙酸衍生物
EP2588455B1 (en) 2010-07-02 2018-04-04 Gilead Sciences, Inc. 2-quinolinyl-acetic acid derivatives as hiv antiviral compounds
US8871744B2 (en) 2010-07-21 2014-10-28 B & G Partyers, LLC Compounds and methods for selectively targeting tumor-associated mucins
MX2013012266A (es) 2011-04-21 2013-11-22 Gilead Sciences Inc Compuestos de benzotiazol y su uso farmaceutico.
WO2013014262A1 (en) 2011-07-27 2013-01-31 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for diagnosing and treating myhre syndrome
US9468612B2 (en) 2011-10-26 2016-10-18 Seattle Children's Hospital Cysteamine in the treatment of fibrotic disease
US9782452B2 (en) 2011-11-22 2017-10-10 Cornell University Methods for stimulating hematopoietic recovery by inhibiting TGFβ signaling
US9284323B2 (en) 2012-01-04 2016-03-15 Gilead Sciences, Inc. Naphthalene acetic acid derivatives against HIV infection
US9376392B2 (en) 2012-01-04 2016-06-28 Gilead Sciences, Inc. 2-(tert-butoxy)-2-(7-methylquinolin-6-yl) acetic acid derivatives for treating AIDS
ES2571479T3 (es) 2012-04-20 2016-05-25 Gilead Sciences Inc Derivados del ácido benzotiazol-6-il acético y su uso para tratar una infección por VIH
CN105007939B (zh) 2012-10-05 2018-10-19 卡德门企业有限公司 人抗vegfr-2/kdr抗体
EP2917365B1 (en) 2012-11-12 2020-03-11 Institució Catalana de Recerca i Estudis Avançats Methods and kits for the prognosis of colorectal cancer
JO3336B1 (ar) 2014-10-07 2019-03-13 Lilly Co Eli مركبات أمينو بيريديلوكسي بيرازول
TWI704151B (zh) 2014-12-22 2020-09-11 美商美國禮來大藥廠 Erk抑制劑
WO2016123573A1 (en) 2015-01-30 2016-08-04 President And Fellows Of Harvard College Peritumoral and intratumoral materials for cancer therapy
EP3277673B1 (en) 2015-04-01 2022-05-04 Rigel Pharmaceuticals, Inc. Tgf-beta inhibitors
US10450318B2 (en) 2015-12-15 2019-10-22 Bristol-Myers Squibb Company CXCR4 receptor antagonists
US10604528B2 (en) 2016-07-07 2020-03-31 Crystal Pharmaceutical (Suzhou) Co., Ltd. Galunisertib crystalline form, preparation method thereof and use thereof
WO2018165979A1 (zh) * 2017-03-17 2018-09-20 杭州领业医药科技有限公司 2-(6-甲基-吡啶-2-基)-3-基-[6-酰胺基-喹啉-4-基]-5,6-二氢-4H-吡咯并[1,2-b]吡唑的晶型及其制备方法和药物组合物
WO2018170724A1 (zh) * 2017-03-21 2018-09-27 杭州领业医药科技有限公司 2-(6-甲基-吡啶-2-基)-3-基-[6-酰胺基-喹啉-4-基]-5,6-二氢-4H-吡咯并[1,2-b]吡唑的共晶,其制备方法和药物组合物
WO2019042383A1 (zh) * 2017-08-31 2019-03-07 苏州科睿思制药有限公司 Galunisertib的晶型及其制备方法和用途
WO2019105082A1 (zh) * 2017-11-30 2019-06-06 苏州科睿思制药有限公司 Galunisertib的晶型及其制备方法和用途
WO2019137027A1 (zh) * 2018-01-12 2019-07-18 苏州科睿思制药有限公司 Galunisertib的晶型及其制备方法和用途
EP3827010B1 (en) 2018-07-23 2025-08-27 Brise Pharmaceuticals Co., Ltd. Bisphosphonate drug conjugates
SG11202103457PA (en) 2018-12-27 2021-05-28 Nexys Therapeutics Inc (pyridin-2-yl)amine derivatives as tgf-beta r1 (alk5) inhibitors for the treatment of cancer
WO2020201362A2 (en) 2019-04-02 2020-10-08 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods of predicting and preventing cancer in patients having premalignant lesions
CN113557236B (zh) * 2019-06-10 2022-05-10 中国科学院广州生物医药与健康研究院 一种双功能免疫调节剂及其在药学上可接受的盐、药物组合物
CN115052663B (zh) 2020-01-08 2026-06-09 辛瑟斯治疗股份有限公司 Alk5抑制剂缀合物及其用途
JP7842690B2 (ja) 2020-02-19 2026-04-08 ナミ セラピューティクス, インコーポレイテッド がんの処置において有用なTFGβアンタゴニストプロドラッグを含有する製剤化および/または共製剤化リポソーム組成物ならびにその方法
WO2024258967A1 (en) 2023-06-13 2024-12-19 Synthis Therapeutics, Inc. Anti-cd5 antibodies and their uses
GB202309553D0 (en) 2023-06-24 2023-08-09 Ucl Business Ltd Compostions and uses thereof

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US5356897A (en) * 1991-09-09 1994-10-18 Fujisawa Pharmaceutical Co., Ltd. 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines
ATE267830T1 (de) * 1999-08-27 2004-06-15 Abbott Lab Als cox-hemmer verwendbare sulfonylphenylpyrazol- verbindungen
SI1397364T1 (sl) * 2001-05-24 2007-12-31 Lilly Co Eli Novi pirolni derivati kot farmacevtske uäśinkovine
EP1567528A1 (en) 2002-11-21 2005-08-31 Eli Lilly And Company Mixed lineage kinase modulators

Also Published As

Publication number Publication date
US20080027102A1 (en) 2008-01-31
NO20053045L (no) 2005-06-21
EA200500859A1 (ru) 2005-10-27
US7834029B2 (en) 2010-11-16
WO2004048382A1 (en) 2004-06-10
CR7830A (es) 2005-06-20
KR20050083945A (ko) 2005-08-26
US20060040983A1 (en) 2006-02-23
DE60308893D1 (de) 2006-11-16
JP4542906B2 (ja) 2010-09-15
ECSP055807A (es) 2005-08-11
DE60308893T2 (de) 2007-03-15
UA80571C2 (en) 2007-10-10
CN1714090A (zh) 2005-12-28
HRP20050436B1 (hr) 2013-11-08
NZ538942A (en) 2007-01-26
PL376797A1 (pl) 2006-01-09
JP2006514012A (ja) 2006-04-27
EG25822A (en) 2012-08-23
DK1565471T3 (da) 2007-02-05
CN100345852C (zh) 2007-10-31
CO5570677A2 (es) 2005-10-31
KR101057282B1 (ko) 2011-08-16
EP1565471B1 (en) 2006-10-04
EP1565471A1 (en) 2005-08-24
ES2273046T3 (es) 2007-05-01
US7265225B2 (en) 2007-09-04
AU2003291643B2 (en) 2010-05-13
CA2501322A1 (en) 2004-06-10
ZA200503121B (en) 2006-07-26
MXPA05005432A (es) 2005-08-03
NO331403B1 (no) 2011-12-19
HK1081948A1 (en) 2006-05-26
PL227840B1 (pl) 2018-01-31
HRP20050436A2 (en) 2005-10-31
AU2003291643A1 (en) 2004-06-18
BR0315337A (pt) 2005-08-16
PT1565471E (pt) 2007-01-31
EA008387B1 (ru) 2007-04-27
IL168190A (en) 2011-01-31
CY1106283T1 (el) 2011-10-12
ATE341550T1 (de) 2006-10-15

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