CA2465757C - Triazole derivatives as cyclooxygenase (cox) inhibitors - Google Patents

Triazole derivatives as cyclooxygenase (cox) inhibitors Download PDF

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Publication number
CA2465757C
CA2465757C CA2465757A CA2465757A CA2465757C CA 2465757 C CA2465757 C CA 2465757C CA 2465757 A CA2465757 A CA 2465757A CA 2465757 A CA2465757 A CA 2465757A CA 2465757 C CA2465757 C CA 2465757C
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CA
Canada
Prior art keywords
compound
salt
mmol
methoxyphenyl
mixture
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
CA2465757A
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English (en)
French (fr)
Other versions
CA2465757A1 (en
Inventor
Satoshi Aoki
Toshiya Nakagawa
Nobukiyo Konishi
Katsuya Nakamura
Hiroki Omori
Ariyoshi Kubota
Norio Hashimoto
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.)
Astellas Pharma Inc
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Astellas Pharma Inc
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Filing date
Publication date
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Publication of CA2465757A1 publication Critical patent/CA2465757A1/en
Application granted granted Critical
Publication of CA2465757C publication Critical patent/CA2465757C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • A61P19/06—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/04—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Transplantation (AREA)
  • Psychiatry (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2465757A 2001-11-09 2002-10-30 Triazole derivatives as cyclooxygenase (cox) inhibitors Expired - Fee Related CA2465757C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AUPR8782 2001-11-09
AUPR8782A AUPR878201A0 (en) 2001-11-09 2001-11-09 New compounds
PCT/JP2002/011314 WO2003040110A1 (en) 2001-11-09 2002-10-30 Triazole derivatives as cyclooxygenase (cox) inhibitors

Publications (2)

Publication Number Publication Date
CA2465757A1 CA2465757A1 (en) 2003-05-15
CA2465757C true CA2465757C (en) 2011-11-29

Family

ID=3832601

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2465757A Expired - Fee Related CA2465757C (en) 2001-11-09 2002-10-30 Triazole derivatives as cyclooxygenase (cox) inhibitors

Country Status (15)

Country Link
US (1) US6927230B2 (enExample)
EP (1) EP1442026B9 (enExample)
JP (2) JP3972208B2 (enExample)
KR (1) KR100511884B1 (enExample)
CN (1) CN100338042C (enExample)
AR (1) AR037347A1 (enExample)
AT (1) ATE427940T1 (enExample)
AU (1) AUPR878201A0 (enExample)
CA (1) CA2465757C (enExample)
DE (1) DE60231897D1 (enExample)
DK (1) DK1442026T3 (enExample)
ES (1) ES2325318T3 (enExample)
PT (1) PT1442026E (enExample)
TW (1) TWI300713B (enExample)
WO (1) WO2003040110A1 (enExample)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002055502A1 (en) * 2001-01-02 2002-07-18 Fujisawa Pharmaceutical Co., Ltd. Pyridine derivatives useful as cyclooxygenase inhibitor
AUPR878201A0 (en) * 2001-11-09 2001-12-06 Fujisawa Pharmaceutical Co., Ltd. New compounds
KR100470076B1 (ko) 2002-11-27 2005-02-05 씨제이 주식회사 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물
WO2004050632A1 (en) 2002-12-02 2004-06-17 Fujisawa Pharmaceutical Co., Ltd. Pyrazole derivatives useful as cox-i inhibitors
WO2004060367A1 (en) * 2002-12-30 2004-07-22 Fujisawa Pharmaceutical Co., Ltd. Imidazole and triazole derivatives useful as selective cox-1 inhibitors
RU2332412C2 (ru) 2003-02-07 2008-08-27 Дайити Фармасьютикал Ко., Лтд. Производные пиразола
EP1620406A2 (en) * 2003-05-08 2006-02-01 Astellas Pharma Inc. 1,2-diarylimidazoles useful as inhibitors of cox
EP1803719A4 (en) * 2004-10-19 2008-07-02 Daiichi Seiyaku Co 1,5-DIHETEROCYCLUS-1H-triazole
KR20100137448A (ko) * 2008-04-01 2010-12-30 아스텔라스세이야쿠 가부시키가이샤 혈관성 질병의 예방제 및/또는 치료제
WO2011152297A1 (ja) * 2010-05-31 2011-12-08 アステラス製薬株式会社 トリアゾール化合物の固体分散体
UA112418C2 (uk) * 2010-09-07 2016-09-12 Астеллас Фарма Інк. Терапевтичний болезаспокійливий засіб
KR101178947B1 (ko) * 2011-04-29 2012-09-03 한국생명공학연구원 올레아놀린산 아세테이트를 유효성분으로 포함하는 ｔｌｒ 및 ｉｌ-6 매개성 질환 예방 또는 치료용 약학적 조성물
WO2012170839A2 (en) * 2011-06-09 2012-12-13 Cardeus Pharmaceuticals, Inc. Treatment of neuroinflammatory disease with selective cox1 inhibitors
EA201590916A1 (ru) * 2012-11-09 2016-02-29 Корнэлл Юниверсити Низкомолекулярные ингибиторы malt1
CN113329754A (zh) 2018-11-20 2021-08-31 麻雀制药股份有限公司 用于施用皮质类固醇的方法
CN115611901B (zh) * 2021-07-16 2024-04-30 华南理工大学 一种氮杂䓬类化合物或其药学上可接受的盐及其制备方法和应用
IL316907A (en) 2022-05-16 2025-01-01 Sparrow Pharmaceuticals Inc METHODS AND COMPOSITIONS FOR TREATING GLUCOCORTICOD EXCESS

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0051084A1 (en) 1980-11-04 1982-05-12 American Cyanamid Company Substituted 1H-1,2,4-triazoles
HU193891B (en) * 1984-02-07 1987-12-28 Gyogyszerkutato Intezet Process for production of new derivatives of 1,2,4-triasole
FI850995A7 (fi) 1984-03-16 1985-09-17 Ciba Geigy Ag Menetelmä uusien 3-merkapto-1,2,4 -triatsasykloalkadieenijohdannaisten valmistamiseksi.
FI850994L (fi) 1984-03-16 1985-09-17 Ciba Geigy Ag Foerfarande foer framstaellning av nya 1,2,4-triazacykloalkadienderivat.
AU581216B2 (en) 1984-04-17 1989-02-16 Henkel Corporation Production of d-alpha-tocopherol from natural plant sources
JPS60233066A (ja) * 1984-05-07 1985-11-19 Nippon Nohyaku Co Ltd １．５−ジフエニルトリアゾ−ル誘導体及びその製造方法
CA2327185A1 (en) 1998-04-08 1999-10-14 Abbott Laboratories Pyrazole inhibitors of cytokine production
ES2221426T3 (es) 1998-08-20 2004-12-16 Smithkline Beecham Corporation Nuevos compuestos de triazol sustituidos.
EP1099695A1 (en) 1999-11-09 2001-05-16 Laboratoire Theramex S.A. 5-aryl-1H-1,2,4-triazole compounds as inhibitors of cyclooxygenase-2 and pharmaceutical compositions containing them
AUPR878201A0 (en) * 2001-11-09 2001-12-06 Fujisawa Pharmaceutical Co., Ltd. New compounds

Also Published As

Publication number Publication date
US20030191155A1 (en) 2003-10-09
AR037347A1 (es) 2004-11-03
EP1442026B9 (en) 2009-11-18
CN100338042C (zh) 2007-09-19
CA2465757A1 (en) 2003-05-15
JP2007169290A (ja) 2007-07-05
KR20030060878A (ko) 2003-07-16
JP3972208B2 (ja) 2007-09-05
ES2325318T3 (es) 2009-09-01
CN1612865A (zh) 2005-05-04
PT1442026E (pt) 2009-06-25
JP2004521964A (ja) 2004-07-22
EP1442026B1 (en) 2009-04-08
EP1442026A1 (en) 2004-08-04
KR100511884B1 (ko) 2005-09-05
WO2003040110A1 (en) 2003-05-15
US6927230B2 (en) 2005-08-09
ATE427940T1 (de) 2009-04-15
DK1442026T3 (da) 2009-07-06
AUPR878201A0 (en) 2001-12-06
TWI300713B (en) 2008-09-11
DE60231897D1 (de) 2009-05-20

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