JP4669225B2 - キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物 - Google Patents

キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物 Download PDF

Info

Publication number
JP4669225B2
JP4669225B2 JP2003587532A JP2003587532A JP4669225B2 JP 4669225 B2 JP4669225 B2 JP 4669225B2 JP 2003587532 A JP2003587532 A JP 2003587532A JP 2003587532 A JP2003587532 A JP 2003587532A JP 4669225 B2 JP4669225 B2 JP 4669225B2
Authority
JP
Japan
Prior art keywords
alkyl
optionally substituted
substituted
phenyl
heterocyclo
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
JP2003587532A
Other languages
English (en)
Japanese (ja)
Other versions
JP2005523338A (ja
JP2005523338A5 (enExample
Inventor
アラリク・ダイクマン
ジョン・ハインズ
カテリナ・レフセリス
リュー・チュンジャン
スティーブン・ティ・ローブルスキー
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.)
Bristol Myers Squibb Co
Original Assignee
Bristol Myers Squibb Co
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 Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of JP2005523338A publication Critical patent/JP2005523338A/ja
Publication of JP2005523338A5 publication Critical patent/JP2005523338A5/ja
Application granted granted Critical
Publication of JP4669225B2 publication Critical patent/JP4669225B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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 two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • 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
    • 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
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Diabetes (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Communicable Diseases (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Molecular Biology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
JP2003587532A 2002-04-23 2003-04-15 キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物 Expired - Fee Related JP4669225B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US37493802P 2002-04-23 2002-04-23
PCT/US2003/012426 WO2003090912A1 (en) 2002-04-23 2003-04-15 Pyrrolo-triazine aniline compounds useful as kinase inhibitors

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2010007097A Division JP5226018B2 (ja) 2002-04-23 2010-01-15 キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物

Publications (3)

Publication Number Publication Date
JP2005523338A JP2005523338A (ja) 2005-08-04
JP2005523338A5 JP2005523338A5 (enExample) 2006-04-27
JP4669225B2 true JP4669225B2 (ja) 2011-04-13

Family

ID=29270573

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2003587532A Expired - Fee Related JP4669225B2 (ja) 2002-04-23 2003-04-15 キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物
JP2010007097A Expired - Fee Related JP5226018B2 (ja) 2002-04-23 2010-01-15 キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2010007097A Expired - Fee Related JP5226018B2 (ja) 2002-04-23 2010-01-15 キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物

Country Status (30)

Country Link
US (5) US7160883B2 (enExample)
EP (2) EP2289894A3 (enExample)
JP (2) JP4669225B2 (enExample)
KR (1) KR101025675B1 (enExample)
CN (2) CN102093363B (enExample)
AR (1) AR039649A1 (enExample)
AU (1) AU2003231034B2 (enExample)
BR (1) BR0309669A (enExample)
CA (1) CA2483164C (enExample)
DK (1) DK1497019T3 (enExample)
ES (1) ES2543711T3 (enExample)
GE (1) GEP20074148B (enExample)
HR (1) HRP20040988A2 (enExample)
HU (1) HUE025353T2 (enExample)
IL (2) IL164573A (enExample)
IS (1) IS7505A (enExample)
MX (1) MXPA04010379A (enExample)
MY (1) MY132094A (enExample)
NO (1) NO329503B1 (enExample)
NZ (1) NZ536014A (enExample)
PE (1) PE20040590A1 (enExample)
PL (1) PL219736B1 (enExample)
PT (1) PT1497019E (enExample)
RS (1) RS92004A (enExample)
RU (1) RU2375363C2 (enExample)
SI (1) SI1497019T1 (enExample)
TW (1) TWI312782B (enExample)
UA (1) UA78562C2 (enExample)
WO (1) WO2003090912A1 (enExample)
ZA (1) ZA200408541B (enExample)

Families Citing this family (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6867300B2 (en) 2000-11-17 2005-03-15 Bristol-Myers Squibb Company Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors
US6670357B2 (en) * 2000-11-17 2003-12-30 Bristol-Myers Squibb Company Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors
BR0309669A (pt) * 2002-04-23 2005-03-01 Bristol Myers Squibb Co Compostos de anilina de pirrolo-triazina úteis como inibidores de cinase
TW200400034A (en) 2002-05-20 2004-01-01 Bristol Myers Squibb Co Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors
TW200401638A (en) * 2002-06-20 2004-02-01 Bristol Myers Squibb Co Heterocyclic inhibitors of kinases
TWI329112B (en) * 2002-07-19 2010-08-21 Bristol Myers Squibb Co Novel inhibitors of kinases
AU2003265349A1 (en) * 2002-08-02 2004-02-23 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
TW200420565A (en) * 2002-12-13 2004-10-16 Bristol Myers Squibb Co C-6 modified indazolylpyrrolotriazines
KR20050099525A (ko) * 2003-02-05 2005-10-13 브리스톨-마이어스 스큅 컴퍼니 피롤로트리아진 키나제 억제제의 제조 방법
WO2005030128A2 (en) * 2003-09-23 2005-04-07 Merck & Co., Inc. Pyrazole modulators of metabotropic glutamate receptors
US7419978B2 (en) * 2003-10-22 2008-09-02 Bristol-Myers Squibb Company Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors
US7309708B2 (en) * 2003-11-20 2007-12-18 Birstol-Myers Squibb Company Hepatitis C virus inhibitors
EP1692110A1 (en) * 2003-12-10 2006-08-23 MERCK PATENT GmbH Diacylhydrazine derivatives
US7102001B2 (en) 2003-12-12 2006-09-05 Bristol-Myers Squibb Company Process for preparing pyrrolotriazine
US7569571B2 (en) * 2003-12-23 2009-08-04 Novartis Ag Substituted pyrazolo [3,4-d]pyrimidines as cytokine modulators
US7064203B2 (en) 2003-12-29 2006-06-20 Bristol Myers Squibb Company Di-substituted pyrrolotriazine compounds
MY145634A (en) 2003-12-29 2012-03-15 Bristol Myers Squibb Co Pyrrolotriazine compounds as kinase inhibitors
US7459562B2 (en) * 2004-04-23 2008-12-02 Bristol-Myers Squibb Company Monocyclic heterocycles as kinase inhibitors
TW200538453A (en) * 2004-04-26 2005-12-01 Bristol Myers Squibb Co Bicyclic heterocycles as kinase inhibitors
US7102002B2 (en) 2004-06-16 2006-09-05 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
US7439246B2 (en) * 2004-06-28 2008-10-21 Bristol-Myers Squibb Company Fused heterocyclic kinase inhibitors
US20050288290A1 (en) * 2004-06-28 2005-12-29 Borzilleri Robert M Fused heterocyclic kinase inhibitors
US7432373B2 (en) * 2004-06-28 2008-10-07 Bristol-Meyers Squibb Company Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors
TW200600513A (en) 2004-06-30 2006-01-01 Bristol Myers Squibb Co A method for preparing pyrrolotriazine compounds
US7253167B2 (en) * 2004-06-30 2007-08-07 Bristol-Myers Squibb Company Tricyclic-heteroaryl compounds useful as kinase inhibitors
US7102003B2 (en) 2004-07-01 2006-09-05 Bristol-Myers Squibb Company Pyrrolotriazine compounds
US7504521B2 (en) 2004-08-05 2009-03-17 Bristol-Myers Squibb Co. Methods for the preparation of pyrrolotriazine compounds
TW200618803A (en) * 2004-08-12 2006-06-16 Bristol Myers Squibb Co Process for preparing pyrrolotriazine aniline compounds useful as kinase inhibitors
US7151176B2 (en) 2004-10-21 2006-12-19 Bristol-Myers Squibb Company Pyrrolotriazine compounds
PT1807431E (pt) * 2004-10-26 2010-11-18 Novartis Ag Pirrolo[1,2-d][1,2-4]triazina como inibidores das quinases c-jun n terminal (jnk) e das quinases p-38
US7534882B2 (en) 2005-04-06 2009-05-19 Bristol-Myers Squibb Company Method for preparing pyrrolotriazine compounds via in situ amination of pyrroles
US20060235020A1 (en) * 2005-04-18 2006-10-19 Soojin Kim Process for preparing salts of 4-[[5-[(cyclopropylamino)carbonyl]-2-methylphenyl]amino]-5-methyl-N-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide and novel stable forms produced therein
US7442700B2 (en) * 2005-07-01 2008-10-28 Bristol-Myers Squibb Company Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith
US7405213B2 (en) * 2005-07-01 2008-07-29 Bristol-Myers Squibb Company Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith
US7402582B2 (en) * 2005-07-01 2008-07-22 Bristol-Myers Squibb Company Pyrrolotriazine compounds useful as kinase inhibitors and methods of treating kinase-associated conditions therewith
US7348325B2 (en) 2005-11-30 2008-03-25 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
US8063208B2 (en) 2006-02-16 2011-11-22 Bristol-Myers Squibb Company Crystalline forms of (3R,4R)-4-amino-1-[[4-[(3-methoxyphenyl)amino]pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol
MX2008011136A (es) 2006-03-07 2008-09-08 Squibb Bristol Myers Co Compuestos de profamarco de pirrolotriazina anilina utiles como inhibidores de cinasa.
US7531539B2 (en) * 2006-08-09 2009-05-12 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
US7982033B2 (en) 2006-11-03 2011-07-19 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
US8268998B2 (en) 2006-11-03 2012-09-18 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
TW201035100A (en) 2008-12-19 2010-10-01 Cephalon Inc Pyrrolotriazines as ALK and JAK2 inhibitors
US8399451B2 (en) * 2009-08-07 2013-03-19 Bristol-Myers Squibb Company Heterocyclic compounds
WO2011133734A1 (en) 2010-04-23 2011-10-27 Bristol-Myers Squibb Company 4 - (5 - isoxazolyl or 5 - pyrrazolyl -1,2,4- oxadiazol - 3 - yl) -mandelic acid amides as sphingosin- 1 - phosphate 1 rreceptor agonists
WO2012031057A1 (en) 2010-09-01 2012-03-08 Bristol-Myers Squibb Company Bms- 582949 for the treatment of resistant rheumatic disease
US9187437B2 (en) 2010-09-24 2015-11-17 Bristol-Myers Squibb Company Substituted oxadiazole compounds
WO2014082230A1 (zh) * 2012-11-28 2014-06-05 上海希迈医药科技有限公司 吡咯并三嗪类衍生物、其制备方法及其在医药上的应用
CN103848833B (zh) * 2012-11-28 2016-08-31 上海希迈医药科技有限公司 吡咯并三嗪类衍生物、其制备方法及其在医药上的应用
WO2014115171A1 (en) 2013-01-24 2014-07-31 Council Of Scientific & Industrial Research Triazine compounds and a process for preparation thereof
CN103601722B (zh) * 2013-09-13 2016-03-02 南京华威医药科技开发有限公司 新型抗肿瘤化合物
ES2678877T3 (es) 2013-10-11 2018-08-20 Bristol-Myers Squibb Company Inhibidores de pirrolotriazina quinasa
RS57542B1 (sr) 2013-10-17 2018-10-31 Blueprint Medicines Corp Kompozicije korisne za lečenje poremećaja povezanih sa kit-om
WO2015091156A1 (en) 2013-12-17 2015-06-25 Boehringer Ingelheim International Gmbh Sulfoximine substituted pyrrolotriazines for pharmaceutical compositions
WO2018129301A1 (en) * 2017-01-05 2018-07-12 Biodesix, Inc. Method for identification of cancer patients with durable benefit from immunotherapy in overall poor prognosis subgroups
WO2018183712A1 (en) 2017-03-31 2018-10-04 Blueprint Medicines Corporation Pyrrolo[1,2-b]pyridazine compounds and compositions useful for treating disorders related to kit and pdgfr
CA3127373A1 (en) 2017-10-05 2019-04-11 Fulcrum Therapeutics, Inc. P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd
US10342786B2 (en) 2017-10-05 2019-07-09 Fulcrum Therapeutics, Inc. P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD
US11760701B2 (en) 2018-02-27 2023-09-19 The Research Foundation For The State University Of New Yrok Difluoromethoxylation and trifluoromethoxylation compositions and methods for synthesizing same
CA3093189A1 (en) 2018-03-07 2019-09-12 Bayer Aktiengesellschaft Identification and use of erk5 inhibitors
CN113966334B (zh) 2019-04-12 2025-01-21 缆图药品公司 化合物(i)的晶体形式
MA55604B1 (fr) 2019-04-12 2024-08-30 Blueprint Medicines Corporation Dérivés de pyrrolotriazine pour le traitement de maladies liées au kit- and pdgfra
TW202112368A (zh) 2019-06-13 2021-04-01 荷蘭商法西歐知識產權股份有限公司 用於治療有關dux4表現之疾病的抑制劑組合
CN110483439B (zh) * 2019-08-28 2022-12-30 郑州手性药物研究院有限公司 6-氨基甲基-1,1-二氧-1,2-苯并噻唑-3-酮的合成方法
CN110483497B (zh) * 2019-08-28 2022-12-30 郑州手性药物研究院有限公司 6-氨基甲基-1,1-二氧-1,2-苯并噻唑-3-酮中间体及其合成方法
CN110627706B (zh) * 2019-08-28 2023-02-10 郑州手性药物研究院有限公司 2-(4-甲基苄基)-1h-异吲哚-1,3-二酮衍生物及其合成方法

Family Cites Families (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3629301A (en) 1969-10-24 1971-12-21 Du Pont 3 3-difluoro-2-substituted steroids and their preparation
US4200750A (en) 1977-01-07 1980-04-29 Westwood Pharmaceuticals Inc. 4-Substituted imidazo [1,2-a]quinoxalines
IL107041A (en) * 1992-09-25 2000-02-17 Lilly Co Eli Process for preparing omega(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo-6-¬2,3-d¾pyrimidin-5-YL)alkarylcarboxylic acids and N-(omega-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo¬2,3-d¾pyrimidin-5-YL)alk-aroyl-4-glutamic acids
IL118544A (en) 1995-06-07 2001-08-08 Smithkline Beecham Corp History of imidazole, the process for their preparation and the pharmaceutical preparations containing them
NZ327044A (en) 1996-01-11 2000-01-28 Smithkline Beecham Corp Substituted imidazole compounds
US6191131B1 (en) * 1997-07-23 2001-02-20 Dupont Pharmaceuticals Company Azolo triazines and pyrimidines
US6147080A (en) 1996-12-18 2000-11-14 Vertex Pharmaceuticals Incorporated Inhibitors of p38
US5945418A (en) 1996-12-18 1999-08-31 Vertex Pharmaceuticals Incorporated Inhibitors of p38
US6087496A (en) 1998-05-22 2000-07-11 G. D. Searle & Co. Substituted pyrazoles suitable as p38 kinase inhibitors
PL336990A1 (en) 1997-05-22 2000-07-31 Searle & Co 3(5)-heteroaryl group substituted pyrazoles as inhibitors of kinase p 38
EP1019396A1 (en) 1997-07-02 2000-07-19 SmithKline Beecham Corporation Novel cycloalkyl substituted imidazoles
WO1999024033A1 (en) * 1997-11-12 1999-05-20 Shionogi & Co., Ltd. Method for the treatment of disorders associated with apoptosis using n-heterocyclic glyoxylamide compounds
US6130235A (en) 1998-05-22 2000-10-10 Scios Inc. Compounds and methods to treat cardiac failure and other disorders
EP1107758A2 (en) 1998-08-28 2001-06-20 Scios Inc. Use of piperidines and/or piperazines as inhibitors of p38-alpha kinase
US6184226B1 (en) 1998-08-28 2001-02-06 Scios Inc. Quinazoline derivatives as inhibitors of P-38 α
AU762245B2 (en) * 1998-09-18 2003-06-19 Vertex Pharmaceuticals Incorporated Inhibitors of p38
ES2191462T3 (es) 1998-10-01 2003-09-01 Astrazeneca Ab Derivados de quinolina y quinazolina y su uso como inhibidores de enfermedades mediadas por citoquinas.
CA2346334A1 (en) * 1998-10-14 2000-04-20 Shionogi & Co., Ltd. Composition for treating or preventing ischemia reperfusion injury
GB9906566D0 (en) 1999-03-23 1999-05-19 Zeneca Ltd Chemical compounds
US6982265B1 (en) 1999-05-21 2006-01-03 Bristol Myers Squibb Company Pyrrolotriazine inhibitors of kinases
WO2000071129A1 (en) * 1999-05-21 2000-11-30 Bristol-Myers Squibb Company Pyrrolotriazine inhibitors of kinases
JP4623483B2 (ja) 1999-08-23 2011-02-02 塩野義製薬株式会社 ｓＰＬＡ２阻害作用を有するピロロトリアジン誘導体
GB9924092D0 (en) 1999-10-13 1999-12-15 Zeneca Ltd Pyrimidine derivatives
PT1140939E (pt) 1999-11-10 2005-05-31 Ortho Mcneil Pharm Inc 2-aril-3-(heteroaril)- imidazo [1,2-alfa] pirimidinas substituidas, e formulacoes farmaceuticas e metodos relacionados
US6906067B2 (en) 1999-12-28 2005-06-14 Bristol-Myers Squibb Company N-heterocyclic inhibitors of TNF-α expression
US20020065270A1 (en) 1999-12-28 2002-05-30 Moriarty Kevin Joseph N-heterocyclic inhibitors of TNF-alpha expression
EE200300227A (et) * 2000-11-17 2003-10-15 Bristol-Myers Squibb Company P38 kinaasiga seotud haigusseisundite ravimeetodid ja kinaasi inhibiitoritena kasulikud pürrolotriasiiniühendid
US6867300B2 (en) * 2000-11-17 2005-03-15 Bristol-Myers Squibb Company Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors
US6670357B2 (en) 2000-11-17 2003-12-30 Bristol-Myers Squibb Company Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors
JP4510442B2 (ja) 2001-06-26 2010-07-21 ブリストル−マイヤーズ スクイブ カンパニー ＴＮＦ−α発現のＮ−ヘテロ環インヒビター
TW200300350A (en) 2001-11-14 2003-06-01 Bristol Myers Squibb Co C-5 modified indazolylpyrrolotriazines
DE60325469D1 (de) 2002-04-23 2009-02-05 Bristol Myers Squibb Co Als kinase inhibitoren geeignete arylketonpyrrolotriazin-verbindungen
BR0309669A (pt) * 2002-04-23 2005-03-01 Bristol Myers Squibb Co Compostos de anilina de pirrolo-triazina úteis como inibidores de cinase
TW200400034A (en) 2002-05-20 2004-01-01 Bristol Myers Squibb Co Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors
TWI329112B (en) 2002-07-19 2010-08-21 Bristol Myers Squibb Co Novel inhibitors of kinases
US6933386B2 (en) 2002-07-19 2005-08-23 Bristol Myers Squibb Company Process for preparing certain pyrrolotriazine compounds
AU2003265349A1 (en) 2002-08-02 2004-02-23 Bristol-Myers Squibb Company Pyrrolotriazine kinase inhibitors
TW200420565A (en) 2002-12-13 2004-10-16 Bristol Myers Squibb Co C-6 modified indazolylpyrrolotriazines
KR20050099525A (ko) 2003-02-05 2005-10-13 브리스톨-마이어스 스큅 컴퍼니 피롤로트리아진 키나제 억제제의 제조 방법
MY145634A (en) * 2003-12-29 2012-03-15 Bristol Myers Squibb Co Pyrrolotriazine compounds as kinase inhibitors
TW200600513A (en) 2004-06-30 2006-01-01 Bristol Myers Squibb Co A method for preparing pyrrolotriazine compounds
US7504521B2 (en) 2004-08-05 2009-03-17 Bristol-Myers Squibb Co. Methods for the preparation of pyrrolotriazine compounds
US7534882B2 (en) 2005-04-06 2009-05-19 Bristol-Myers Squibb Company Method for preparing pyrrolotriazine compounds via in situ amination of pyrroles
US20060235020A1 (en) 2005-04-18 2006-10-19 Soojin Kim Process for preparing salts of 4-[[5-[(cyclopropylamino)carbonyl]-2-methylphenyl]amino]-5-methyl-N-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide and novel stable forms produced therein
MX2008011136A (es) 2006-03-07 2008-09-08 Squibb Bristol Myers Co Compuestos de profamarco de pirrolotriazina anilina utiles como inhibidores de cinasa.

Also Published As

Publication number Publication date
US20070043053A1 (en) 2007-02-22
EP1497019A1 (en) 2005-01-19
GEP20074148B (en) 2007-07-10
JP2010132673A (ja) 2010-06-17
US20110098467A1 (en) 2011-04-28
US7462616B2 (en) 2008-12-09
EP1497019B1 (en) 2015-05-20
RU2004134337A (ru) 2005-06-27
JP2005523338A (ja) 2005-08-04
AU2003231034A1 (en) 2003-11-10
TW200402422A (en) 2004-02-16
IS7505A (is) 2004-10-14
ES2543711T3 (es) 2015-08-21
PT1497019E (pt) 2015-09-10
CN102093363A (zh) 2011-06-15
TWI312782B (en) 2009-08-01
MY132094A (en) 2007-09-28
PL373338A1 (en) 2005-08-22
HRP20040988A2 (en) 2005-06-30
UA78562C2 (en) 2007-04-10
EP2289894A2 (en) 2011-03-02
AU2003231034B2 (en) 2009-03-05
RU2375363C2 (ru) 2009-12-10
US20040082582A1 (en) 2004-04-29
EP1497019A4 (en) 2006-06-14
NO329503B1 (no) 2010-11-01
EP2289894A3 (en) 2011-07-20
CN102093363B (zh) 2016-12-07
KR101025675B1 (ko) 2011-03-30
IL185604A0 (en) 2008-01-06
IL164573A (en) 2010-12-30
IL164573A0 (en) 2005-12-18
HUE025353T2 (en) 2016-02-29
CN1662509A (zh) 2005-08-31
NO20044560L (no) 2004-11-10
NZ536014A (en) 2006-12-22
MXPA04010379A (es) 2005-02-17
PE20040590A1 (es) 2004-08-28
DK1497019T3 (en) 2015-08-03
US20090105243A1 (en) 2009-04-23
US7160883B2 (en) 2007-01-09
RS92004A (sr) 2006-12-15
ZA200408541B (en) 2006-01-25
US7759343B2 (en) 2010-07-20
WO2003090912A1 (en) 2003-11-06
PL219736B1 (pl) 2015-07-31
US20100240646A1 (en) 2010-09-23
JP5226018B2 (ja) 2013-07-03
AR039649A1 (es) 2005-03-02
SI1497019T1 (sl) 2015-08-31
CA2483164A1 (en) 2003-11-06
WO2003090912A9 (en) 2004-01-08
KR20040102157A (ko) 2004-12-03
BR0309669A (pt) 2005-03-01
CA2483164C (en) 2011-06-07

Similar Documents

Publication Publication Date Title
JP4669225B2 (ja) キナーゼ阻害剤として有用なピロロトリアジンアニリン化合物
JP2005529890A (ja) キナーゼ阻害剤として有用なアリールケトンピロロトリアジン化合物
JP4662775B2 (ja) キナーゼ阻害剤として有用なピロロトリアジン化合物の調製方法
DE60117607T2 (de) Verfahren zur Behandlung von mit p38-Kinase assoziierten Leiden und Pyrrolotriazin-Verbindungen als Kinaseinhibitoren.
JP2005531584A (ja) ピラゾロピリミジンアニリン化合物
US20030069244A1 (en) Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors
JP2009535295A (ja) キナーゼ阻害剤として有用なピロロトリアジンアニリンプロドラッグ化合物
AU2002232760A1 (en) Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20060309

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20060309

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20090818

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20091118

RD03 Notification of appointment of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: A7423

Effective date: 20091118

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20091126

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20091217

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20091225

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100115

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100216

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100428

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100921

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20101122

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20101221

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20110114

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20140121

Year of fee payment: 3

R150 Certificate of patent or registration of utility model

Free format text: JAPANESE INTERMEDIATE CODE: R150

Ref document number: 4669225

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees