CA2451279C - Derivatives of triazolyl-imidazopyridine and of the triazolylpurines useful as ligands of the adenosine a2a receptor and their use as medicaments - Google Patents

Derivatives of triazolyl-imidazopyridine and of the triazolylpurines useful as ligands of the adenosine a2a receptor and their use as medicaments Download PDF

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Publication number
CA2451279C
CA2451279C CA2451279A CA2451279A CA2451279C CA 2451279 C CA2451279 C CA 2451279C CA 2451279 A CA2451279 A CA 2451279A CA 2451279 A CA2451279 A CA 2451279A CA 2451279 C CA2451279 C CA 2451279C
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Canada
Prior art keywords
compound
pharmaceutically acceptable
acceptable salt
treatment
disease
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
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CA2451279A
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English (en)
French (fr)
Other versions
CA2451279A1 (en
Inventor
Giorgio Tarzia
Giovanni Piersanti
Patrizia Minetti
Maria Assunta Di Cesare
Grazia Gallo
Fabrizio Giorgi
Luca Giorgi
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Sigma Tau Industrie Farmaceutiche Riunite SpA
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Sigma Tau Industrie Farmaceutiche Riunite SpA
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Publication of CA2451279A1 publication Critical patent/CA2451279A1/en
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Publication of CA2451279C publication Critical patent/CA2451279C/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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • 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
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • C07D473/34—Nitrogen atom attached in position 6, e.g. adenine

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2451279A 2001-07-31 2002-07-25 Derivatives of triazolyl-imidazopyridine and of the triazolylpurines useful as ligands of the adenosine a2a receptor and their use as medicaments Expired - Fee Related CA2451279C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT2001RM000465A ITRM20010465A1 (it) 2001-07-31 2001-07-31 Derivati della triazolil-imidazopiridina e delle triazolilpurine utili come ligandi del recettore a2a dell'adenosina e loro uso come medicam
ITRM01A000465 2001-07-31
PCT/IT2002/000489 WO2003011864A1 (en) 2001-07-31 2002-07-25 DERIVATIVES OF TRIAZOLYL-IMIDAZOPYRIDINE AND OF THE TRIAZOLYLPURINES USEFUL AS LIGANDS OF THE ADENOSINE A2a RECEPTOR AND THEIR USE AS MEDICAMENTS

Publications (2)

Publication Number Publication Date
CA2451279A1 CA2451279A1 (en) 2003-02-13
CA2451279C true CA2451279C (en) 2011-05-10

Family

ID=11455703

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2451279A Expired - Fee Related CA2451279C (en) 2001-07-31 2002-07-25 Derivatives of triazolyl-imidazopyridine and of the triazolylpurines useful as ligands of the adenosine a2a receptor and their use as medicaments

Country Status (18)

Country Link
US (2) US7230102B2 (cg-RX-API-DMAC7.html)
EP (1) EP1412354B1 (cg-RX-API-DMAC7.html)
JP (1) JP4366186B2 (cg-RX-API-DMAC7.html)
KR (1) KR100884818B1 (cg-RX-API-DMAC7.html)
CN (1) CN1271070C (cg-RX-API-DMAC7.html)
AT (1) ATE325796T1 (cg-RX-API-DMAC7.html)
AU (1) AU2002326146B2 (cg-RX-API-DMAC7.html)
BR (1) BR0211550A (cg-RX-API-DMAC7.html)
CA (1) CA2451279C (cg-RX-API-DMAC7.html)
DE (1) DE60211343T2 (cg-RX-API-DMAC7.html)
DK (1) DK1412354T3 (cg-RX-API-DMAC7.html)
ES (1) ES2263810T3 (cg-RX-API-DMAC7.html)
HU (1) HU228985B1 (cg-RX-API-DMAC7.html)
IT (1) ITRM20010465A1 (cg-RX-API-DMAC7.html)
MX (1) MXPA04000886A (cg-RX-API-DMAC7.html)
PL (1) PL217269B1 (cg-RX-API-DMAC7.html)
PT (1) PT1412354E (cg-RX-API-DMAC7.html)
WO (1) WO2003011864A1 (cg-RX-API-DMAC7.html)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100883292B1 (ko) * 2001-06-29 2009-02-11 씨브이 쎄러퓨틱스, 인코포레이티드 Ａ２ｂ 아데노신 수용체 길항제로서의 퓨린 유도체
ITRM20010465A1 (it) * 2001-07-31 2003-01-31 Sigma Tau Ind Farmaceuti Derivati della triazolil-imidazopiridina e delle triazolilpurine utili come ligandi del recettore a2a dell'adenosina e loro uso come medicam
US7189730B2 (en) * 2001-12-18 2007-03-13 Cv Therapeutics, Inc. A2A adenosine receptor antagonists
CA2559036C (en) 2004-03-26 2013-08-20 Dainippon Sumitomo Pharma Co., Ltd. 9-substituted 8-oxoadenine compound
US8063063B2 (en) * 2006-03-23 2011-11-22 Novartis Ag Immunopotentiating compounds
US8138172B2 (en) 2006-07-05 2012-03-20 Astrazeneca Ab 8-oxoadenine derivatives acting as modulators of TLR7
TW200831105A (en) 2006-12-14 2008-08-01 Astrazeneca Ab Novel compounds
ES2373616T3 (es) 2007-03-19 2012-02-07 Astrazeneca Ab Compuestos de 8-oxo-adenina 9 sustituidos como moduladores del receptor de tipo toll (tlr7).
JP5480637B2 (ja) 2007-03-19 2014-04-23 アストラゼネカ・アクチエボラーグ Ｔｏｌｌ様受容体（ｔｌｒ７）モジュレーターとしての９−置換−８−オキソ−アデニン化合物
TW200902018A (en) * 2007-03-20 2009-01-16 Dainippon Sumitomo Pharma Co Novel adenine compound
HRP20130910T1 (hr) * 2007-03-20 2013-10-25 Curis, Inc. Kondenzirani aminopiridin kao inhibitori hsp90
WO2008114819A1 (ja) 2007-03-20 2008-09-25 Dainippon Sumitomo Pharma Co., Ltd. 新規アデニン化合物
JP5400763B2 (ja) * 2007-05-08 2014-01-29 アストラゼネカ・アクチエボラーグ 免疫調節特性を有するイミダゾキノリン類
PE20091156A1 (es) 2007-12-17 2009-09-03 Astrazeneca Ab Sales de (3-{[[3-(6-amino-2-butoxi-8-oxo-7,8-dihidro-9h-purin-9-il)propil](3-morfolin-4-ilpropil)amino]metil}fenil)acetato de metilo
JPWO2009091031A1 (ja) * 2008-01-17 2011-05-26 大日本住友製薬株式会社 アデニン化合物の製造方法
CA2711769A1 (en) 2008-01-17 2009-07-23 Dainippon Sumitomo Pharma Co. Ltd. Method for preparing adenine compound
TWI473614B (zh) * 2008-05-29 2015-02-21 Kyowa Hakko Kirin Co Ltd Anti-analgesic inhibitors
US8846947B2 (en) 2008-07-03 2014-09-30 Glaxosmithkline Llc Benzimidazoles and related analogs as sirtuin modulators
AU2009274876C1 (en) 2008-07-23 2016-08-18 Kyowa Kirin Co., Ltd. Therapeutic agent for migraine
PT2408775E (pt) 2009-03-20 2015-08-05 Sigma Tau Ind Farmaceuti Derivados oxidados de triazolil purinas úteis como ligandos do recetor a2a de adenosina e a sua utilização como medicamentos
TWI398255B (zh) 2009-11-13 2013-06-11 Academia Sinica 結合至腺苷酸ａａ受體和腺苷酸轉運子以預防及治療神經退化疾病的雙功能化合物
WO2011068233A1 (en) * 2009-12-03 2011-06-09 Dainippon Sumitomo Pharma Co., Ltd. Imidazoquinolines which act via toll - like receptors (tlr)
WO2012070601A1 (ja) * 2010-11-24 2012-05-31 ヤマサ醤油株式会社 新規な２－アルキニル－ｎ９－プロパギルアデニンおよびその医薬用途
WO2012080728A1 (en) 2010-12-16 2012-06-21 Astrazeneca Ab Imidazo [4, 5 -c] quinolin- 1 -yl derivative useful in therapy
DK2651943T3 (en) 2010-12-17 2017-06-06 Sumitomo Dainippon Pharma Co Ltd purine derivatives
US9512120B2 (en) 2013-03-15 2016-12-06 Syngenta Participations Ag Microbicidally active imidazopyridine derivatives
CN105622495A (zh) * 2016-03-23 2016-06-01 叶芳 4-氯-3-硝基吡啶及其制备方法
US20190111069A1 (en) * 2016-04-15 2019-04-18 Oxford University Innovation Limited Adenosine Receptor Modulators for the Treatment of Circadian Rhythm Disorders
WO2025080645A1 (en) * 2023-10-10 2025-04-17 Regranion, Llc Methods and compositions for treating bullous pemphigoid
GB202319534D0 (en) * 2023-12-19 2024-01-31 Circadian Therapeutics Ltd Dosage regimen

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WO1990009178A1 (en) 1989-01-31 1990-08-23 Whitby Research, Inc. N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists
US5670501A (en) * 1994-09-01 1997-09-23 Discovery Therapeutics, Inc. N-substituted 9-alkyladenines
EP1054012B1 (en) 1998-01-05 2003-06-11 Eisai Co., Ltd. Purine derivatives and adenosine a2 receptor antagonists serving as preventives/remedies for diabetes
GB9915437D0 (en) * 1999-07-01 1999-09-01 Cerebrus Ltd Chemical compounds III
KR100883292B1 (ko) * 2001-06-29 2009-02-11 씨브이 쎄러퓨틱스, 인코포레이티드 Ａ２ｂ 아데노신 수용체 길항제로서의 퓨린 유도체
ITRM20010465A1 (it) 2001-07-31 2003-01-31 Sigma Tau Ind Farmaceuti Derivati della triazolil-imidazopiridina e delle triazolilpurine utili come ligandi del recettore a2a dell'adenosina e loro uso come medicam

Also Published As

Publication number Publication date
EP1412354A1 (en) 2004-04-28
CN1271070C (zh) 2006-08-23
CN1525974A (zh) 2004-09-01
ES2263810T3 (es) 2006-12-16
HUP0401987A3 (en) 2012-12-28
US20040204428A1 (en) 2004-10-14
ATE325796T1 (de) 2006-06-15
DE60211343D1 (de) 2006-06-14
JP4366186B2 (ja) 2009-11-18
PL368409A1 (en) 2005-03-21
ITRM20010465A0 (it) 2001-07-31
US7230102B2 (en) 2007-06-12
KR20040023641A (ko) 2004-03-18
WO2003011864A1 (en) 2003-02-13
PL217269B1 (pl) 2014-06-30
CA2451279A1 (en) 2003-02-13
MXPA04000886A (es) 2004-06-03
DE60211343T2 (de) 2007-05-10
DK1412354T3 (da) 2006-09-18
US20070249638A1 (en) 2007-10-25
AU2002326146B2 (en) 2008-05-01
HU228985B1 (en) 2013-07-29
KR100884818B1 (ko) 2009-02-20
EP1412354B1 (en) 2006-05-10
ITRM20010465A1 (it) 2003-01-31
BR0211550A (pt) 2004-07-13
HK1068334A1 (en) 2005-04-29
HUP0401987A2 (hu) 2005-01-28
PT1412354E (pt) 2006-09-29
US7528252B2 (en) 2009-05-05
JP2005500355A (ja) 2005-01-06

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