DK0880524T3 - Adenosine antagonists, processes for their preparation and their use as drugs - Google Patents

Adenosine antagonists, processes for their preparation and their use as drugs

Info

Publication number
DK0880524T3
DK0880524T3 DK97933683T DK97933683T DK0880524T3 DK 0880524 T3 DK0880524 T3 DK 0880524T3 DK 97933683 T DK97933683 T DK 97933683T DK 97933683 T DK97933683 T DK 97933683T DK 0880524 T3 DK0880524 T3 DK 0880524T3
Authority
DK
Denmark
Prior art keywords
optionally substituted
alkyl
alkenyl
alkynyl
cycloalkyl
Prior art date
Application number
DK97933683T
Other languages
Danish (da)
Inventor
Ulrike Kuefner-Muehl
Werner Kummer
Gerald Pohl
Wolfram Gaida
Erich Lehr
Joachim Mierau
Thomas Weiser
Original Assignee
Boehringer Ingelheim Pharma
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Boehringer Ingelheim Pharma filed Critical Boehringer Ingelheim Pharma
Priority claimed from CA002242097A external-priority patent/CA2242097C/en
Application granted granted Critical
Publication of DK0880524T3 publication Critical patent/DK0880524T3/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12Heterocyclic 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 three hetero rings
    • C07D487/14Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/36Antigestagens
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10Antioedematous agents; Diuretics

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Endocrinology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

1,2,4-TriazoloÄ1,5-aÜpurin-9-one derivatives of formula (I), and their racemates, enantiomers, diastereomers and/or acid addition salts are new. R1 or R3 and R4 or R5 = H, Z, COOZ, SO2Z, SO2A, COZ, aralkyl, aralkenyl, aralkynyl, A, COOA, SO2A, COA, CONHR or (all optionally substituted) benzyloxycarbonyl, benzylsulphonyl, 4-8C cycloalkenyl, 6-8C cycloalkynyl, benzyl, or benzylcarbonyl; Z = 1-10C alkyl, 3-8C cycloalkyl, 6-10C aryl, heteroaryl (all optionally substituted), 2-10C alkenyl or 2-10C alkynyl; A = optionally substituted 5-7 membered heterocycle (containing one or more of N, S and O as heteroatom(s) and bonded via C); R = H, or phenyl, benzyl or 3-6C cycloalkyl (all optionally substituted), or alkyl, alkenyl or alkynyl (all of up to 10C and optionally substituted by OH, optionally substituted phenyl or optionally substituted amino); R2 = H, OH, NH2, halo, NO2, CF3, COOH, SH, 1-6C alkylthio, SO2Z, benzylsulphonyl, OSO2Z, NHSO2Z, CONHZ, di-(1-10C alkyl or 2-10C alkenyl)-aminocarbonyl, N-(1-10C alkyl)-N-(2-10C alkenyl or alkynyl)-aminocarbonyl, NHCOOZ, OCONHZ, C(=NH)NHZ, OZ, COOZ, OCOZ, SZ, optionally substituted amino, preferably NR8R9, or (all optionally substituted) 1-10C alkyl, 2-10C alkenyl, 2-10C alkynyl, 3-8C cycloalkyl, 5-8C cycloalkanone, 4-8C cycloalkenyl, 6-8C cycloalkynyl, 6-10C aryl, aryl-(1-6C)alkyl, aryl-(2-6C)alkenyl, aryl-(2-6C)alkynyl, cycloalkyl-(1-6C)alkyl, cycloalkyl-(2-6C)alkenyl, cycloalkyl-(2-6C)alkynyl, 5-7 membered heterocycle (containing one or more of O, S and optionally substituted N as heteroatom(s) and linked via C- or N- or via a 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl bridge), or (all optionally substituted) 1-10C alkyl, 2-10C alkenyl, 2-10C alkynyl, 3-8C cycloalkyl, 5-8C cycloalkanone, 4-8C cycloalkenyl, 6-8C cycloalkynyl, 6-10C aryl, aryl-(1-6C)alkyl, aryl-(2-6C)alkenyl, aryl-(2-6C)alkynyl, cycloalkyl-(1-6C)alkyl, cycloalkyl-(2-6C)alkenyl, cycloalkyl-(2-6C)alkynyl, 5-7 membered heterocycle (containing one or more of O, S and optionally substituted N as heteroatom(s) and linked via C- or N- or via a 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl bridge), methylenedioxyphenyl, ethylenedioxyphenyl, fluorenyl or optionally substituted group of formula (a)-(e); R6 = as for R2 or CHO; x = 1 or 2; y = 0-2; dotted lines in (a) = optional bonds; Q = H or 1-6C alkyl, but cannot be alkyl if the ring system in (a) contains two double bonds; Y = bond, 1-6C alkylene, 2-6C alkenylene or 2-6C alkynylene; R8, R9 = 1-10C alkyl, 2-10C alkenyl or 2-10C alkynyl (optionally substituted by OH, optionally substituted phenyl, optionally substituted benzyl, optionally substituted amino or 1-6C alkoxy), H, optionally substituted 3-6C cycloalkyl, (CH2)mNHCOOR4; or NR8R9 = saturated or unsaturated 5- or 6- membered ring (optionally containing another O, S or N heteroatom and optionally substituted by 1-4C alkyl, (CH2)nPh, (CH2)nNH2, oxo, ketal (preferably OCH2CH2O), (CH2)nNH-(1-4C alkyl), (CH2)nN(1-8C alkyl)2, (CH2)nNHCOOR10, halo, OR10, CN, NO2, NH2, CH2NR8R9 (sic), OH, COOH, SO3H, COOR10, CONR8R9 (sic) or SO2R10); m = 1-4; n = 2-4; R10 = H, 1-4C alkyl, 2-4C alkenyl, 2-4C alkynyl, or benzyl or phenyl (both optionally substituted by one or more OMe).
DK97933683T 1996-07-20 1997-07-17 Adenosine antagonists, processes for their preparation and their use as drugs DK0880524T3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19629378A DE19629378A1 (en) 1996-07-20 1996-07-20 New triazolopurines, process for their preparation and their use as medicaments
PCT/EP1997/003841 WO1998003511A1 (en) 1996-07-20 1997-07-17 New triazolopurines, method of preparing them and their use as drugs
CA002242097A CA2242097C (en) 1996-07-20 1998-06-26 Imidazotriazolopyrimidines, process for preparing them and their use as pharmaceutical compositions

Publications (1)

Publication Number Publication Date
DK0880524T3 true DK0880524T3 (en) 2000-07-17

Family

ID=32963000

Family Applications (1)

Application Number Title Priority Date Filing Date
DK97933683T DK0880524T3 (en) 1996-07-20 1997-07-17 Adenosine antagonists, processes for their preparation and their use as drugs

Country Status (25)

Country Link
EP (2) EP0880524B1 (en)
JP (1) JP3020281B2 (en)
CN (1) CN1219936A (en)
AT (1) ATE191913T1 (en)
AU (1) AU3695597A (en)
BG (1) BG102707A (en)
BR (1) BR9710747A (en)
CA (1) CA2256736A1 (en)
CZ (1) CZ265498A3 (en)
DE (2) DE19629378A1 (en)
DK (1) DK0880524T3 (en)
EE (1) EE9800451A (en)
ES (1) ES2147453T3 (en)
GR (1) GR3033842T3 (en)
HR (1) HRP970395A2 (en)
HU (1) HUP9902311A3 (en)
ID (1) ID19106A (en)
IL (1) IL126453A0 (en)
NO (1) NO983860L (en)
PL (1) PL328824A1 (en)
PT (1) PT880524E (en)
SK (1) SK114498A3 (en)
TR (1) TR199801659T2 (en)
WO (1) WO1998003511A1 (en)
ZA (1) ZA976331B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19826843A1 (en) * 1998-06-16 1999-12-23 Boehringer Ingelheim Pharma Novel imidazotriazolopyrimidines, process for their preparation and their use as medicaments
US6492377B1 (en) 1998-06-25 2002-12-10 Boehringer Ingelheim Pharma Kg Imidazotriazolopyrimidines with adenosine-antagonistic activity
WO2000012511A1 (en) * 1998-08-27 2000-03-09 Boehringer Ingelheim Pharma Kg Imidazotriazolopyrimidines
WO2004075846A2 (en) 2003-02-25 2004-09-10 Bristol-Myers Squibb Company Pyrazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same
US7071333B2 (en) 2003-07-30 2006-07-04 Bristol-Myers Squibb Company Triazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same
EP2044074A2 (en) * 2006-06-23 2009-04-08 Incyte Corporation Purinone derivatives as hm74a agonists
IL303087B1 (en) 2018-02-27 2024-08-01 Incyte Corp Imidazopyrimidines and triazolopyrimidines as a2a / a2b inhibitors
US11168089B2 (en) 2018-05-18 2021-11-09 Incyte Corporation Fused pyrimidine derivatives as A2A / A2B inhibitors
CN113166153A (en) 2018-07-05 2021-07-23 因赛特公司 Fused pyrazine derivatives as A2A/A2B inhibitors
JP7241871B2 (en) 2018-11-30 2023-03-17 メルク・シャープ・アンド・ドーム・エルエルシー 9-substituted aminotriazoloquinazoline derivatives, pharmaceutical compositions and their use as adenosine receptor antagonists
TWI829857B (en) 2019-01-29 2024-01-21 美商英塞特公司 Pyrazolopyridines and triazolopyridines as a2a / a2b inhibitors
CN112778311B (en) * 2019-11-01 2024-06-04 上海翰森生物医药科技有限公司 Nitrogen-containing fused ring derivative inhibitor, preparation method and application thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA902282B (en) * 1989-03-29 1990-12-28 Merrell Dow Pharma Selective adenosine receptor compounds
IT1264901B1 (en) * 1993-06-29 1996-10-17 Schering Plough S P A HETEROCYCLIC ANALOGUES OF 1,2,4-TRIAZOLE(15-C)PYRIMIDINES WITH ANTAGONIST ACTIVITY FOR THE ADENOSINE A2 RECEPTOR
JPH083169A (en) * 1994-06-15 1996-01-09 Yamasa Shoyu Co Ltd 4-methyl-1h-(1,2,4)triazolo(1,5-a)purin-9(4h)-ones

Also Published As

Publication number Publication date
DE59701467D1 (en) 2000-05-25
NO983860D0 (en) 1998-08-21
BG102707A (en) 1999-09-30
ES2147453T3 (en) 2000-09-01
ID19106A (en) 1998-06-18
PT880524E (en) 2000-07-31
NO983860L (en) 1998-10-21
JP2000501420A (en) 2000-02-08
EP0978517A3 (en) 2003-11-12
PL328824A1 (en) 1999-02-15
ATE191913T1 (en) 2000-05-15
HUP9902311A2 (en) 1999-10-28
BR9710747A (en) 1999-08-17
AU3695597A (en) 1998-02-10
EP0880524A1 (en) 1998-12-02
CZ265498A3 (en) 1998-12-16
JP3020281B2 (en) 2000-03-15
CA2256736A1 (en) 1998-01-29
TR199801659T2 (en) 1998-12-21
IL126453A0 (en) 1999-08-17
HUP9902311A3 (en) 2000-06-28
GR3033842T3 (en) 2000-10-31
WO1998003511A1 (en) 1998-01-29
EE9800451A (en) 1999-06-15
HRP970395A2 (en) 1998-08-31
ZA976331B (en) 1999-01-25
EP0978517A2 (en) 2000-02-09
EP0880524B1 (en) 2000-04-19
CN1219936A (en) 1999-06-16
DE19629378A1 (en) 1998-01-29
SK114498A3 (en) 1999-02-11

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