CA2401241C - 2-amino-3-(alkyl)-pyrimidone derivatives as gsk3.beta. inhibitors - Google Patents

2-amino-3-(alkyl)-pyrimidone derivatives as gsk3.beta. inhibitors Download PDF

Info

Publication number
CA2401241C
CA2401241C CA2401241A CA2401241A CA2401241C CA 2401241 C CA2401241 C CA 2401241C CA 2401241 A CA2401241 A CA 2401241A CA 2401241 A CA2401241 A CA 2401241A CA 2401241 C CA2401241 C CA 2401241C
Authority
CA
Canada
Prior art keywords
group
pyridin
methyl
amino
pyrimidin
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
CA2401241A
Other languages
English (en)
French (fr)
Other versions
CA2401241A1 (en
Inventor
Antonio Almario Garcia
Ryoichi Ando
Keiichi Aritomo
Jonathan Reid Frost
Adrien Tak Li
Aya Shoda
Fumiaki Uehara
Kazutoshi Watanabe
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.)
Sanofi Aventis France
Mitsubishi Tanabe Pharma Corp
Original Assignee
Sanofi Synthelabo SA
Mitsubishi Pharma Corp
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 Sanofi Synthelabo SA, Mitsubishi Pharma Corp filed Critical Sanofi Synthelabo SA
Publication of CA2401241A1 publication Critical patent/CA2401241A1/en
Application granted granted Critical
Publication of CA2401241C publication Critical patent/CA2401241C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • 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
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/14Drugs for dermatological disorders for baldness or alopecia
    • 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
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/26Psychostimulants, e.g. nicotine, cocaine
    • 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
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • A61P27/06Antiglaucoma agents or miotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Dermatology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Virology (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Reproductive Health (AREA)
  • Cardiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2401241A 2000-03-23 2001-03-22 2-amino-3-(alkyl)-pyrimidone derivatives as gsk3.beta. inhibitors Expired - Fee Related CA2401241C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP00400800A EP1136482A1 (en) 2000-03-23 2000-03-23 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors
EP00400800.9 2000-03-23
PCT/EP2001/003640 WO2001070729A1 (en) 2000-03-23 2001-03-22 2-amino-3-(alkyl)-pyrimidone derivatives as gsk3.beta. inhibitors

Publications (2)

Publication Number Publication Date
CA2401241A1 CA2401241A1 (en) 2001-09-27
CA2401241C true CA2401241C (en) 2011-11-29

Family

ID=8173604

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2401241A Expired - Fee Related CA2401241C (en) 2000-03-23 2001-03-22 2-amino-3-(alkyl)-pyrimidone derivatives as gsk3.beta. inhibitors

Country Status (16)

Country Link
US (2) US6844335B2 (enExample)
EP (2) EP1136482A1 (enExample)
JP (1) JP4778657B2 (enExample)
KR (1) KR100820543B1 (enExample)
CN (2) CN1247567C (enExample)
AR (1) AR028280A1 (enExample)
AT (1) ATE380806T1 (enExample)
AU (1) AU2001281487A1 (enExample)
CA (1) CA2401241C (enExample)
CY (1) CY1107236T1 (enExample)
DE (1) DE60131844T2 (enExample)
DK (1) DK1276738T3 (enExample)
ES (1) ES2296783T3 (enExample)
PT (1) PT1276738E (enExample)
SI (1) SI1276738T1 (enExample)
WO (1) WO2001070729A1 (enExample)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI241298B (en) 1998-09-25 2005-10-11 Mitsubishi Chem Corp Pyrimidone derivatives
EP1136482A1 (en) * 2000-03-23 2001-09-26 Sanofi-Synthelabo 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors
SE518184C2 (sv) 2000-03-31 2002-09-03 Perstorp Flooring Ab Golvbeläggningsmaterial innefattande skivformiga golvelement vilka sammanfogas med hjälp av sammankopplingsorgan
ATE284712T1 (de) 2000-04-26 2005-01-15 Eisai Co Ltd Medizinische zusammensetzungen zur förderung der aktivierung der eingeweide
IL160701A0 (en) 2001-09-21 2004-08-31 Mitsubishi Pharma Corp 3-substituted-4-pyrimidone derivatives
MXPA04002662A (es) * 2001-09-21 2004-11-22 Sanofi Aventis Derivados de 3-substituida-4-pirimidona.
TW201041580A (en) * 2001-09-27 2010-12-01 Alcon Inc Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma
TWI330183B (enExample) 2001-10-22 2010-09-11 Eisai R&D Man Co Ltd
TWI301834B (en) * 2001-10-22 2008-10-11 Eisai R&D Man Co Ltd Pyrimidone compound and pharmaceutical composition including the same
EA009027B1 (ru) * 2002-12-16 2007-10-26 Мицубиси Фарма Корпорейшн Производные 3-замещенного-4-пиримидона
EP1460075A1 (en) * 2003-03-21 2004-09-22 Sanofi-Synthelabo Substituted 8-Pyridinyl-6,7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 8-Phenyl-6-7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one derivatives
EP1460076A1 (en) * 2003-03-21 2004-09-22 Sanofi-Synthelabo Substituted 8-perfluoroalkyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one derivatives
US7550590B2 (en) 2003-03-25 2009-06-23 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors
TWI357408B (en) * 2003-03-26 2012-02-01 Mitsubishi Tanabe Pharma Corp 3-substituted-4-pyrimidone derivatives
WO2005016911A1 (en) 2003-08-13 2005-02-24 Takeda Pharmaceutical Company Limited 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors
EP1699777B1 (en) 2003-09-08 2012-12-12 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors
EP1713793A4 (en) * 2004-02-04 2009-09-02 Smithkline Beecham Corp PYRIMIDINONE COMPOUNDS SUITED AS KINASEINHIBITORS
UA85871C2 (uk) 2004-03-15 2009-03-10 Такеда Фармасьютікал Компані Лімітед Інгібітори дипептидилпептидази
CN1980681A (zh) * 2004-07-09 2007-06-13 新加坡科技研究局 GSK-3β的调节及治疗增殖性病变的方法
TW200621760A (en) 2004-09-09 2006-07-01 Mitsubishi Pharma Corp 2-morpholino-4-pyrimidone compound
CA2581179A1 (en) * 2004-09-29 2006-04-06 Mitsubishi Pharma Corporation 6-(pyridinyl)-4 pyrimidone derivatives as tau protein kinase 1 inhibitors
JP2008524331A (ja) 2004-12-21 2008-07-10 武田薬品工業株式会社 ジペプチジルペプチダーゼ阻害剤
US20080207594A1 (en) 2005-05-04 2008-08-28 Davelogen Aktiengesellschaft Use of Gsk-3 Inhibitors for Preventing and Treating Pancreatic Autoimmune Disorders
EP2258359A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis by muscarinic receptor modulation with sabcomelin
US7678363B2 (en) 2005-08-26 2010-03-16 Braincells Inc Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs
WO2007033350A1 (en) 2005-09-14 2007-03-22 Takeda Pharmaceutical Company Limited Dipeptidyl peptidase inhibitors for treating diabetes
EP1924567B1 (en) 2005-09-16 2012-08-22 Takeda Pharmaceutical Company Limited Process for the preparation of pyrimidinedione derivatives
WO2007047978A2 (en) 2005-10-21 2007-04-26 Braincells, Inc. Modulation of neurogenesis by pde inhibition
AU2006308889A1 (en) 2005-10-31 2007-05-10 Braincells, Inc. GABA receptor mediated modulation of neurogenesis
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
TW200813015A (en) 2006-03-15 2008-03-16 Mitsubishi Pharma Corp 2-(cyclic amino)-pyrimidone derivatives
CA2651813A1 (en) 2006-05-09 2007-11-22 Braincells, Inc. Neurogenesis by modulating angiotensin
ATE530540T1 (de) * 2006-08-23 2011-11-15 Pfizer Prod Inc Pyrimidonverbindungen als gsk-3-inhibitoren
US8324383B2 (en) 2006-09-13 2012-12-04 Takeda Pharmaceutical Company Limited Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
TW200838536A (en) 2006-11-29 2008-10-01 Takeda Pharmaceutical Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor
US8093236B2 (en) 2007-03-13 2012-01-10 Takeda Pharmaceuticals Company Limited Weekly administration of dipeptidyl peptidase inhibitors
WO2010099217A1 (en) 2009-02-25 2010-09-02 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
AR076014A1 (es) * 2009-04-02 2011-05-11 Sanofi Aventis Derivados de 3- (1,4) oxazepan -4-pirimidona
US8940738B2 (en) 2009-08-13 2015-01-27 Mitsubishi Tanabe Pharma Corporation Pyrimidone compounds
JP5535310B2 (ja) 2009-08-13 2014-07-02 田辺三菱製薬株式会社 タウプロテインキナーゼ1阻害剤としてのピリミドン誘導体
WO2016008966A1 (en) 2014-07-17 2016-01-21 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for treating neuromuscular junction-related diseases
WO2016207366A1 (en) 2015-06-26 2016-12-29 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods and pharmaceutical compositions for the treatment of viral infections
WO2018217766A1 (en) 2017-05-22 2018-11-29 Whitehead Institute For Biomedical Research Kcc2 expression enhancing compounds and uses thereof
WO2025215108A1 (en) * 2024-04-10 2025-10-16 Universitat De Barcelona DUAL G9A/GSK-3ß INHIBITORS

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4935631B1 (enExample) 1970-12-28 1974-09-25
JPS4935633B1 (enExample) 1970-12-30 1974-09-25
JPS559099B2 (enExample) * 1972-08-07 1980-03-07
JPS4935633A (enExample) 1972-08-09 1974-04-02
US4460589A (en) * 1980-10-03 1984-07-17 The Upjohn Company Process for treating hypertension
TW229142B (enExample) * 1992-04-15 1994-09-01 Nissan Detrochem Corp
AU4920397A (en) * 1996-10-11 1998-05-11 Chiron Corporation Purine inhibitors of glycogen synthase kinase 3 (gsk3)
BR9713863A (pt) * 1996-12-05 2000-03-14 Amgen Inc Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, processos de profilaxia ou tratamento, para abaixar as concentrações no plasma, para diminuir a produção de prostaglandinas, e, para diminuir a atividade de enzima ciclooxigenase
WO1998024782A2 (en) * 1996-12-05 1998-06-11 Amgen Inc. Substituted pyrimidine compounds and their use
TWI241298B (en) * 1998-09-25 2005-10-11 Mitsubishi Chem Corp Pyrimidone derivatives
EP1136482A1 (en) * 2000-03-23 2001-09-26 Sanofi-Synthelabo 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors

Also Published As

Publication number Publication date
DE60131844T2 (de) 2008-11-27
JP2003528095A (ja) 2003-09-24
JP4778657B2 (ja) 2011-09-21
AR028280A1 (es) 2003-04-30
EP1136482A1 (en) 2001-09-26
WO2001070729A1 (en) 2001-09-27
DE60131844D1 (de) 2008-01-24
CN1891220A (zh) 2007-01-10
US6844335B2 (en) 2005-01-18
ES2296783T3 (es) 2008-05-01
US20030187004A1 (en) 2003-10-02
EP1276738B8 (en) 2008-02-20
CA2401241A1 (en) 2001-09-27
US20050130998A1 (en) 2005-06-16
SI1276738T1 (sl) 2008-06-30
ATE380806T1 (de) 2007-12-15
US7378413B2 (en) 2008-05-27
KR100820543B1 (ko) 2008-04-07
PT1276738E (pt) 2008-02-28
CN1419552A (zh) 2003-05-21
CN1247567C (zh) 2006-03-29
KR20020093848A (ko) 2002-12-16
AU2001281487A1 (en) 2001-10-03
EP1276738B1 (en) 2007-12-12
EP1276738A1 (en) 2003-01-22
CY1107236T1 (el) 2012-05-23
DK1276738T3 (da) 2008-04-21

Similar Documents

Publication Publication Date Title
CA2401241C (en) 2-amino-3-(alkyl)-pyrimidone derivatives as gsk3.beta. inhibitors
WO2001070728A1 (en) 2-[nitrogen-heterocyclic]pyrimidone derivatives
KR100800250B1 (ko) 2-피리디닐-6,7,8,9-테트라히드로피리미도[1,2-α]피리미딘-4-온 및7-피리디닐-2,3-디히드로이미다조[1,2-α]피리미딘-5(1H)온유도체
EP1460075A1 (en) Substituted 8-Pyridinyl-6,7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 8-Phenyl-6-7,8,9-Tetrahydropyrimido[1,2-a]Pyrimidin-4-one derivatives
AU2002212249A1 (en) 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one derivatives
EP1295885A1 (en) Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido(1,2-a)pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo(1,2-a)pyrimidin-5(1H)one derivatives
EP1480981B1 (en) 1-(alkyl), 1-(heteroaryl)alkyl and 1-[(aryl)alkyl]-7-(pyrimidin-4-yl)-imidazo[1,2-a]pyrimidin-5(1h)-one derivatives
EP1136483A1 (en) 2-[Piperazinyl]pyrimidone derivatives
KR100775192B1 (ko) 1-[알킬], 1-[(헤테로아릴)알킬] 및1-[(아릴)알킬]-7-피리디닐-이미다조[1,2-α]피리미딘-5(1H)-온 유도체
AU2002212248A1 (en) 1-(alkyl), 1-((heteroaryl)alkyl) and 1-((aryl)alkyl)-7- pyridinyl-imidazo(1,2-a)pyrimidin-5(1H)-one derivatives
EP1136484A1 (en) 2-(Arylalkylamino)pyrimidone derivatives
EP1136493A1 (en) 2-(Thienopyridinyl)pyrimidone, 2-(furopyridinyl)pyrimidone 2-(isoquinolinyl)pyrimidone, 2-(pyridoindolyl)pyrimidone and 2-(benzofuropyridinyl)pyrimidone derivatives
EP1136099A1 (en) 2-(Indolylalkylamino)pyrimidone derivatives as GSK3beta inhibitors
EP1184383A1 (en) 9-[Alkyl], 9-[(heteroaryl)alkyl] and 9-[(aryl)alkyl]-2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one derivatives

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20140324