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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CA
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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Classifications

    • 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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (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
ITRM01A000465 2001-07-31
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
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 (https=)
EP (1) EP1412354B1 (https=)
JP (1) JP4366186B2 (https=)
KR (1) KR100884818B1 (https=)
CN (1) CN1271070C (https=)
AT (1) ATE325796T1 (https=)
AU (1) AU2002326146B2 (https=)
BR (1) BR0211550A (https=)
CA (1) CA2451279C (https=)
DE (1) DE60211343T2 (https=)
DK (1) DK1412354T3 (https=)
ES (1) ES2263810T3 (https=)
HU (1) HU228985B1 (https=)
IT (1) ITRM20010465A1 (https=)
MX (1) MXPA04000886A (https=)
PL (1) PL217269B1 (https=)
PT (1) PT1412354E (https=)
WO (1) WO2003011864A1 (https=)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60206756T2 (de) * 2001-06-29 2006-07-13 CV Therapeutics, Inc., Palo Alto Purin derivate als a2b adenosin rezeptor antagonisten
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
ATE355291T1 (de) * 2001-12-18 2006-03-15 Cv Therapeutics Inc A2a adenosinrezeptorantagonisten
WO2005092893A1 (ja) 2004-03-26 2005-10-06 Dainippon Sumitomo Pharma Co., Ltd. ９置換−８−オキソアデニン化合物
CA2646891A1 (en) * 2006-03-23 2007-09-27 Novartis Ag Immunopotentiating compounds
EP2041135A4 (en) 2006-07-05 2010-12-01 Astrazeneca Ab As TLR7 MODULATORS, 8-OXOADENINE DERIVATIVES WORK
TW200831105A (en) 2006-12-14 2008-08-01 Astrazeneca Ab Novel compounds
EP2132209B8 (en) 2007-03-19 2014-04-16 AstraZeneca AB 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7 ) modulators
EP2139894B1 (en) 2007-03-19 2011-10-26 AstraZeneca AB 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7) modulators
AR065784A1 (es) * 2007-03-20 2009-07-01 Dainippon Sumitomo Pharma Co Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas.
JP5401329B2 (ja) * 2007-03-20 2014-01-29 キュリス，インコーポレイテッド Ｈｓｐ９０インヒビターとしての縮合アミノピリジン
WO2008114819A1 (ja) 2007-03-20 2008-09-25 Dainippon Sumitomo Pharma Co., Ltd. 新規アデニン化合物
KR20100016289A (ko) * 2007-05-08 2010-02-12 아스트라제네카 아베 면역-조정 특성의 이미다조퀴놀린
UY31531A1 (es) 2007-12-17 2009-08-03 Sales derivadas de 8-oxoadenina composiciones farmacéuticas que las contienen y su uso en terapia como moduladores de receptor tipo toll (tlr)
WO2009091032A1 (ja) 2008-01-17 2009-07-23 Dainippon Sumitomo Pharma Co., Ltd. アデニン化合物の製造方法
US20110054168A1 (en) * 2008-01-17 2011-03-03 Ayumu Kurimoto Method for preparing adenine compound
TWI473614B (zh) * 2008-05-29 2015-02-21 Kyowa Hakko Kirin Co Ltd Anti-analgesic inhibitors
AU2009266889B2 (en) 2008-07-03 2013-05-02 Glaxosmithkline Llc Benzimidazoles and related analogs as sirtuin modulators
NZ590793A (en) * 2008-07-23 2012-07-27 Kyowa Hakko Kirin Co Ltd Therapeutic agent for migraine
HRP20150766T1 (hr) * 2009-03-20 2015-08-14 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Oksidirani derivati triazolilpurina, korisni kao ligandi adenozinskog receptora a2a, te namijenjeni upotrebi kao medikamenti
US20120295863A1 (en) * 2009-11-13 2012-11-22 Yun-Lian Lin Dual-Action Compounds Targeting Adenosine A2A Receptor and Adenosine Transporter for Prevention and Treatment of Neurodegenerative Diseases
JP2013512859A (ja) * 2009-12-03 2013-04-18 大日本住友製薬株式会社 トール様受容体（ｔｌｒ）を介して作用するイミダゾキノリン
JP5714602B2 (ja) * 2010-11-24 2015-05-07 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
JP5978225B2 (ja) 2010-12-16 2016-08-24 大日本住友製薬株式会社 治療に有用なイミダゾ［４，５−ｃ］キノリン−１−イル誘導体
ES2627433T3 (es) 2010-12-17 2017-07-28 Sumitomo Dainippon Pharma Co., Ltd. Derivados de purina
CA2902833A1 (en) 2013-03-15 2014-09-18 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
ES2957548T3 (es) * 2016-04-15 2024-01-22 Univ Oxford Innovation Ltd Moduladores del receptor de adenosina para el tratamiento de los trastornos del ritmo circadiano
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

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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AU626983B2 (en) 1989-01-31 1992-08-13 Whitby Research, Inc. N6-substituted 9-methyladenines
US5670501A (en) * 1994-09-01 1997-09-23 Discovery Therapeutics, Inc. N-substituted 9-alkyladenines
AU1688599A (en) * 1998-01-05 1999-07-26 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
DE60206756T2 (de) * 2001-06-29 2006-07-13 CV Therapeutics, Inc., Palo Alto Purin derivate als a2b adenosin rezeptor antagonisten
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
PT1412354E (pt) 2006-09-29
CN1271070C (zh) 2006-08-23
PL217269B1 (pl) 2014-06-30
JP4366186B2 (ja) 2009-11-18
JP2005500355A (ja) 2005-01-06
BR0211550A (pt) 2004-07-13
ITRM20010465A1 (it) 2003-01-31
WO2003011864A1 (en) 2003-02-13
ITRM20010465A0 (it) 2001-07-31
DE60211343T2 (de) 2007-05-10
ATE325796T1 (de) 2006-06-15
US20040204428A1 (en) 2004-10-14
US7230102B2 (en) 2007-06-12
AU2002326146B2 (en) 2008-05-01
CA2451279A1 (en) 2003-02-13
MXPA04000886A (es) 2004-06-03
HK1068334A1 (en) 2005-04-29
EP1412354A1 (en) 2004-04-28
ES2263810T3 (es) 2006-12-16
EP1412354B1 (en) 2006-05-10
PL368409A1 (en) 2005-03-21
KR100884818B1 (ko) 2009-02-20
US7528252B2 (en) 2009-05-05
US20070249638A1 (en) 2007-10-25
DE60211343D1 (de) 2006-06-14
CN1525974A (zh) 2004-09-01
DK1412354T3 (da) 2006-09-18
KR20040023641A (ko) 2004-03-18
HUP0401987A2 (hu) 2005-01-28
HUP0401987A3 (en) 2012-12-28
HU228985B1 (en) 2013-07-29

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