AU3695597A - New triazolopurines, method of preparing them and their use as drugs - Google Patents

New triazolopurines, method of preparing them and their use as drugs

Info

Publication number
AU3695597A
AU3695597A AU36955/97A AU3695597A AU3695597A AU 3695597 A AU3695597 A AU 3695597A AU 36955/97 A AU36955/97 A AU 36955/97A AU 3695597 A AU3695597 A AU 3695597A AU 3695597 A AU3695597 A AU 3695597A
Authority
AU
Australia
Prior art keywords
optionally substituted
alkyl
alkenyl
alkynyl
cycloalkyl
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
AU36955/97A
Inventor
Wolfram Gaida
Werner Kummer
Erich Lehr
Joachim Mierau
Gerald Pohl
Thomas Weiser
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.)
Boehringer Ingelheim International GmbH
Original Assignee
Boehringer Ingelheim International GmbH
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 International GmbH filed Critical Boehringer Ingelheim International GmbH
Publication of AU3695597A publication Critical patent/AU3695597A/en
Priority to CA002242097A priority Critical patent/CA2242097C/en
Priority claimed from CA002242097A external-priority patent/CA2242097C/en
Priority to AU17418/99A priority patent/AU1741899A/en
Abandoned legal-status Critical Current

Links

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

Landscapes

  • 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)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Hospice & Palliative Care (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Psychology (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).
AU36955/97A 1996-07-20 1997-07-17 New triazolopurines, method of preparing them and their use as drugs Abandoned AU3695597A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002242097A CA2242097C (en) 1996-07-20 1998-06-26 Imidazotriazolopyrimidines, process for preparing them and their use as pharmaceutical compositions
AU17418/99A AU1741899A (en) 1996-07-20 1999-02-19 New imidazotriazolopyrimidinones, processes for preparing them and their use as pharmaceutical compositions

Applications Claiming Priority (4)

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
DE19629378 1996-07-20
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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU17418/99A Division AU1741899A (en) 1996-07-20 1999-02-19 New imidazotriazolopyrimidinones, processes for preparing them and their use as pharmaceutical compositions

Publications (1)

Publication Number Publication Date
AU3695597A true AU3695597A (en) 1998-02-10

Family

ID=32963000

Family Applications (1)

Application Number Title Priority Date Filing Date
AU36955/97A Abandoned AU3695597A (en) 1996-07-20 1997-07-17 New triazolopurines, method of preparing them and their use as drugs

Country Status (25)

Country Link
EP (2) EP0978517A3 (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 (11)

* 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
AU9347498A (en) * 1998-08-27 2000-03-21 Boehringer Ingelheim Pharma Kg Imidazotriazolopyrimidines
US7329668B2 (en) 2003-02-25 2008-02-12 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
CN101466714B (en) 2006-06-23 2013-02-06 英赛特股份有限公司 Purinone derivatives as HM74A agonists
CN112384515A (en) 2018-02-27 2021-02-19 因赛特公司 Imidazopyrimidines and triazolopyrimidines as A2A/A2B inhibitors
US11168089B2 (en) 2018-05-18 2021-11-09 Incyte Corporation Fused pyrimidine derivatives as A2A / A2B inhibitors
GEP20237548B (en) 2018-07-05 2023-10-10 Incyte Corp Fused pyrazine derivatives as a2a /a2b inhibitors
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
AU623755B2 (en) * 1989-03-29 1992-05-21 Merrell Pharmaceuticals Inc. 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
HUP9902311A3 (en) 2000-06-28
CA2256736A1 (en) 1998-01-29
CZ265498A3 (en) 1998-12-16
DK0880524T3 (en) 2000-07-17
HRP970395A2 (en) 1998-08-31
EP0978517A2 (en) 2000-02-09
DE59701467D1 (en) 2000-05-25
NO983860D0 (en) 1998-08-21
DE19629378A1 (en) 1998-01-29
ATE191913T1 (en) 2000-05-15
CN1219936A (en) 1999-06-16
JP2000501420A (en) 2000-02-08
ID19106A (en) 1998-06-18
TR199801659T2 (en) 1998-12-21
JP3020281B2 (en) 2000-03-15
EP0880524A1 (en) 1998-12-02
GR3033842T3 (en) 2000-10-31
PL328824A1 (en) 1999-02-15
EP0978517A3 (en) 2003-11-12
ES2147453T3 (en) 2000-09-01
PT880524E (en) 2000-07-31
ZA976331B (en) 1999-01-25
IL126453A0 (en) 1999-08-17
WO1998003511A1 (en) 1998-01-29
HUP9902311A2 (en) 1999-10-28
BG102707A (en) 1999-09-30
EP0880524B1 (en) 2000-04-19
NO983860L (en) 1998-10-21
EE9800451A (en) 1999-06-15
SK114498A3 (en) 1999-02-11
BR9710747A (en) 1999-08-17

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