CA2660133C - Thiophenecarboxamide derivatives as ep4 receptor ligands - Google Patents

Thiophenecarboxamide derivatives as ep4 receptor ligands Download PDF

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Publication number
CA2660133C
CA2660133C CA2660133A CA2660133A CA2660133C CA 2660133 C CA2660133 C CA 2660133C CA 2660133 A CA2660133 A CA 2660133A CA 2660133 A CA2660133 A CA 2660133A CA 2660133 C CA2660133 C CA 2660133C
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CA
Canada
Prior art keywords
group
pharmaceutically acceptable
acceptable salt
compound according
formula
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
CA2660133A
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English (en)
French (fr)
Other versions
CA2660133A1 (en
Inventor
Marc Blouin
Jason Burch
Han Yongxin
Christophe Mellon
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.)
Merck Canada Inc
Original Assignee
Merck Canada Inc
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 Merck Canada Inc filed Critical Merck Canada Inc
Publication of CA2660133A1 publication Critical patent/CA2660133A1/en
Application granted granted Critical
Publication of CA2660133C publication Critical patent/CA2660133C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (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)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
CA2660133A 2006-08-11 2007-08-10 Thiophenecarboxamide derivatives as ep4 receptor ligands Expired - Fee Related CA2660133C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US83725206P 2006-08-11 2006-08-11
US60/837,252 2006-08-11
PCT/CA2007/001404 WO2008017164A1 (en) 2006-08-11 2007-08-10 Thiophenecarboxamide derivatives as ep4 receptor ligands

Publications (2)

Publication Number Publication Date
CA2660133A1 CA2660133A1 (en) 2008-02-14
CA2660133C true CA2660133C (en) 2015-10-27

Family

ID=39032586

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2660133A Expired - Fee Related CA2660133C (en) 2006-08-11 2007-08-10 Thiophenecarboxamide derivatives as ep4 receptor ligands

Country Status (8)

Country Link
US (1) US8969394B2 (Direct)
EP (1) EP2054401B1 (Direct)
JP (1) JP5259592B2 (Direct)
CN (1) CN101541778B (Direct)
AU (1) AU2007283404B2 (Direct)
CA (1) CA2660133C (Direct)
ES (1) ES2421453T3 (Direct)
WO (1) WO2008017164A1 (Direct)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009005076A1 (ja) * 2007-07-03 2009-01-08 Astellas Pharma Inc. アミド化合物
AU2008284303A1 (en) * 2007-08-09 2009-02-12 Merck & Co., Inc. Process for making thiophene carboxamide derivative
DK2565191T3 (da) * 2008-05-14 2014-11-10 Astellas Pharma Inc 4-(Indol-7-ylcarbonylaminomethyl)cyclohexancarboxylsyrederivater som EP4-receptorantagonister der er anvendelige til behandlingen af kronisk nyresvigt eller diabetisk nephropati
US8404736B2 (en) * 2008-08-14 2013-03-26 Beta Pharma Canada Inc. Heterocyclic amide derivatives as EP4 receptor antagonists
CA2777384A1 (en) 2009-10-14 2011-04-21 Gemmus Pharma, Inc. Combination therapy treatment for viral infections
ES2600355T3 (es) * 2010-02-22 2017-02-08 Raqualia Pharma Inc. Uso de un antagonista del receptor EP4 en el tratamiento de dermatitis de contacto alérgica y psoriasis
KR101911105B1 (ko) 2010-09-21 2018-10-23 에자이 알앤드디 매니지먼트 가부시키가이샤 제약 조성물
US8828987B2 (en) 2010-12-10 2014-09-09 Rottapharm Biotech S.R.L. Pyridine amide derivatives as EP4 receptor antagonists
UA115576C2 (uk) 2012-12-06 2017-11-27 Байєр Фарма Акцієнгезелльшафт Похідні бензимідазолу як антагоністи ер4
RU2663620C2 (ru) 2013-03-19 2018-08-07 Аскат Инк. Применение рецептора антагониста ер4 для лечения хрящевой болезни
US10391086B2 (en) 2013-03-19 2019-08-27 Askat Inc. Use of EP4 receptor antagonists in the treatment of cartilage disease
DK3009426T3 (en) 2013-06-12 2018-05-28 Kaken Pharma Co Ltd 4-ALKYNYL-IMIDAZOLE DERIVATIVE AND MEDICINE COMPREHENSIVE AS AN ACTIVE INGREDIENT
US20160184387A1 (en) 2013-08-09 2016-06-30 Dominique Charmot Compounds and methods for inhibiting phosphate transport
TW201607943A (zh) 2013-12-19 2016-03-01 拜耳製藥公司 作為ｅｐ４配體之新穎苯并咪唑衍生物
TW201623277A (zh) 2014-03-26 2016-07-01 安斯泰來製藥股份有限公司 醯胺化合物
US20170182003A1 (en) * 2014-05-23 2017-06-29 Eisai R&D Management Co., Ltd. Combination therapies for the treatment of cancer
KR20170010059A (ko) * 2014-06-06 2017-01-25 알러간, 인코포레이티드 치료적 화합물로서 신규한 ep4 작용제
CN105037186A (zh) * 2015-06-17 2015-11-11 苏州敬业医药化工有限公司 一种氨甲苯酸的制备方法
CR20180323A (es) 2015-11-20 2018-08-06 Idorsia Pharmaceuticals Ltd Derivados de indol n-sustituídos como moduladores de los receptores de pge2
WO2018162562A1 (en) 2017-03-10 2018-09-13 Bayer Pharma Aktiengesellschaft Use of an ep4 antagonist for the treatment of inflammatory pain
PE20191811A1 (es) 2017-05-18 2019-12-26 Idorsia Pharmaceuticals Ltd Derivados de pirimidina como moduladores del receptor de pge2
CA3063632A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Benzofurane and benzothiophene derivatives as pge2 receptor modulators
CA3060597A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Phenyl derivatives as pge2 receptor modulators
SG11201908660RA (en) 2017-05-18 2019-10-30 Idorsia Pharmaceuticals Ltd N-substituted indole derivatives
AR111874A1 (es) 2017-05-18 2019-08-28 Idorsia Pharmaceuticals Ltd Derivados de pirimidina
WO2019038156A1 (en) 2017-08-22 2019-02-28 Bayer Pharma Aktiengesellschaft USE OF AN EP4 ANTAGONIST FOR THE TREATMENT OF ARTHRITIS
US10202415B1 (en) 2017-10-19 2019-02-12 King Saud University Method of synthesizing of 3-oxolupenal nanoparticles
WO2020237096A1 (en) 2019-05-21 2020-11-26 Ardelyx, Inc. Combination for lowering serum phosphate in a patient
CN112552200B (zh) * 2019-09-10 2024-03-12 烟台药物研究所 一种光学纯4-(1-氨基)乙基苯甲酸酯及其盐的制备方法
JP7775288B2 (ja) * 2020-08-18 2025-11-25 ハチメド リミテッド ピリミジノン化合物およびその使用
EP4245301A4 (en) 2020-11-13 2024-08-21 ONO Pharmaceutical Co., Ltd. TREATMENT OF CANCER BY COMBINED USE OF AN EP4 ANTAGONIST AND AN IMMUNE CHECKPOINT INHIBITOR

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962490A (en) * 1987-09-25 1999-10-05 Texas Biotechnology Corporation Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
US5834468A (en) * 1995-07-07 1998-11-10 Zeneca Limited Substituted aryl and heteroaryl compounds as E-type prostaglandin antagonists
BR0116850A (pt) * 2001-01-31 2004-02-25 Pfizer Prod Inc Derivados de amida de ácido tiazolil-, oxazolil-, pirrolil- e imidazolil- úteis como inibidores de isoenzimas de pde4
WO2004099127A1 (en) 2003-05-07 2004-11-18 Novo Nordisk A/S Novel compounds as kinase inhibitors
BRPI0414130B8 (pt) * 2003-09-03 2021-05-25 Askat Inc compostos de fenilamida ou piridilamida, seu uso e composições farmacêuticas que os compreendem.
GB0324269D0 (en) * 2003-10-16 2003-11-19 Pharmagene Lab Ltd EP4 receptor antagonists
JP2007533723A (ja) * 2004-04-20 2007-11-22 ファイザー・プロダクツ・インク α２δリガンドを含む組合せ
EA200601830A1 (ru) 2004-05-04 2007-04-27 Пфайзер Инк. Ортозамещённые арильные или гетероарильные амидные соединения
AP2006003785A0 (en) * 2004-05-04 2006-10-31 Pfizer Substituted methylaryl or heteroaryl amide compounds
WO2005116010A1 (en) * 2004-05-26 2005-12-08 Merck Frosst Canada Ltd. Ep4 receptor agonist, compositions and methods thereof

Also Published As

Publication number Publication date
EP2054401B1 (en) 2013-05-01
JP5259592B2 (ja) 2013-08-07
EP2054401A4 (en) 2010-10-13
CN101541778B (zh) 2014-10-08
CA2660133A1 (en) 2008-02-14
AU2007283404A1 (en) 2008-02-14
US20090247596A1 (en) 2009-10-01
JP2010500293A (ja) 2010-01-07
US8969394B2 (en) 2015-03-03
EP2054401A1 (en) 2009-05-06
AU2007283404B2 (en) 2013-04-18
ES2421453T3 (es) 2013-09-02
WO2008017164A1 (en) 2008-02-14
CN101541778A (zh) 2009-09-23

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Effective date: 20180810