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
Other languages
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)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (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 (enExample)
EP (1) EP2054401B1 (enExample)
JP (1) JP5259592B2 (enExample)
CN (1) CN101541778B (enExample)
AU (1) AU2007283404B2 (enExample)
CA (1) CA2660133C (enExample)
ES (1) ES2421453T3 (enExample)
WO (1) WO2008017164A1 (enExample)

Families Citing this family (31)

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WO2009005076A1 (ja) * 2007-07-03 2009-01-08 Astellas Pharma Inc. アミド化合物
JP2010535765A (ja) * 2007-08-09 2010-11-25 メルク・シャープ・エンド・ドーム・コーポレイション チオフェンカルボキサミド誘導体の製造方法
PL2565191T3 (pl) 2008-05-14 2015-03-31 Astellas Pharma Inc Pochodne kwasu 4-(indol-7-ilokarbonyloaminometylo)cykloheksanokarboksylowego jako antagoniści receptora EP4 użyteczni do leczenia przewlekłej niewydolności nerek lub nefropatii cukrzycowej
CA2733247C (en) * 2008-08-14 2018-04-03 Beta Pharma Canada Inc. Heterocyclic amide derivatives as ep4 receptor antagonists
JP2013508282A (ja) 2009-10-14 2013-03-07 ジェンムス ファーマ インコーポレイティド ウイルス感染のための併用療法処置
BR112012020236A2 (pt) * 2010-02-22 2016-05-17 Raqualia Pharma Inc uso de um composto com atividade antagonística de ep4 ou um sal farmaceuticamente aceitável do mesmo, uso de um composto da fórmula (i), (ii), (iii), (iv), (va) ou (vb), ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica e método para o tratamento de doenças mediadas por il-23 em um sujeito animal, incluindo um sujeito mamífero
KR101911105B1 (ko) 2010-09-21 2018-10-23 에자이 알앤드디 매니지먼트 가부시키가이샤 제약 조성물
WO2012076063A1 (en) 2010-12-10 2012-06-14 Rottapharm S.P.A. Pyridine amide derivatives as ep4 receptor antagonists
UA115576C2 (uk) 2012-12-06 2017-11-27 Байєр Фарма Акцієнгезелльшафт Похідні бензимідазолу як антагоністи ер4
US20160317514A1 (en) 2013-03-19 2016-11-03 Askat Inc. Use of ep4 receptor antagonists in the treatment of cartilage disease
US10391086B2 (en) 2013-03-19 2019-08-27 Askat Inc. Use of EP4 receptor antagonists in the treatment of cartilage disease
WO2014200075A1 (ja) 2013-06-12 2014-12-18 科研製薬株式会社 ４－アルキニルイミダゾール誘導体およびそれを有効成分として含有する医薬
AU2014305843B2 (en) 2013-08-09 2019-08-29 Ardelyx, Inc. 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
KR102535283B1 (ko) * 2014-05-23 2023-05-22 에자이 알앤드디 매니지먼트 가부시키가이샤 암의 치료를 위한 조합 요법
AU2015269064B2 (en) * 2014-06-06 2020-02-13 Allergan, Inc. Novel EP4 agonists as therapeutic compounds
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
HRP20211533T1 (hr) 2017-05-18 2022-01-07 Idorsia Pharmaceuticals Ltd Derivati fenila kao modulatori receptora pge2
TWI768043B (zh) 2017-05-18 2022-06-21 瑞士商愛杜西亞製藥有限公司 N-取代吲哚衍生物
US11325899B2 (en) 2017-05-18 2022-05-10 Idorsia Pharmaceuticals Ltd Benzofurane and benzothiophene derivatives as PGE2 receptor modulators
ES2896476T3 (es) 2017-05-18 2022-02-24 Idorsia Pharmaceuticals Ltd Derivados de pirimidina
AR111808A1 (es) 2017-05-18 2019-08-21 Idorsia Pharmaceuticals Ltd Derivados de pirimidina como moduladores del receptor de pge2
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
US20200368223A1 (en) 2019-05-21 2020-11-26 Ardelyx, Inc. Methods for inhibiting phosphate transport
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
IL300471A (en) * 2020-08-18 2023-04-01 Hutchison Medipharma Ltd Pyrimidinone compounds and their uses
KR20230107228A (ko) 2020-11-13 2023-07-14 오노 야꾸힝 고교 가부시키가이샤 Ep4 길항약과 면역 체크포인트 저해 물질의 병용에 의한 암 치료

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
WO2002060898A1 (en) * 2001-01-31 2002-08-08 Pfizer Products Inc. Thiazolyl-, oxazolyl-, pyrrolyl-, and imidazolyl-acid amide derivatives useful as inhibitors of pde4 isozymes
WO2004099127A1 (en) * 2003-05-07 2004-11-18 Novo Nordisk A/S Novel compounds as kinase inhibitors
EP1663979B1 (en) 2003-09-03 2013-10-09 RaQualia Pharma Inc. Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists
GB0324269D0 (en) 2003-10-16 2003-11-19 Pharmagene Lab Ltd EP4 receptor antagonists
US20090036495A1 (en) 2004-04-20 2009-02-05 Pfizer, Inc. Combinations Comprising Alpha-2-Delta Ligands and Ep4 Receptor Antagonists
AP2006003785A0 (en) * 2004-05-04 2006-10-31 Pfizer Substituted methylaryl or heteroaryl amide compounds
AU2005238292A1 (en) 2004-05-04 2005-11-10 Pfizer Inc. Ortho substituted aryl 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
JP2010500293A (ja) 2010-01-07
AU2007283404B2 (en) 2013-04-18
EP2054401B1 (en) 2013-05-01
CN101541778A (zh) 2009-09-23
CN101541778B (zh) 2014-10-08
ES2421453T3 (es) 2013-09-02
US8969394B2 (en) 2015-03-03
US20090247596A1 (en) 2009-10-01
EP2054401A4 (en) 2010-10-13
JP5259592B2 (ja) 2013-08-07
EP2054401A1 (en) 2009-05-06
CA2660133A1 (en) 2008-02-14
AU2007283404A1 (en) 2008-02-14
WO2008017164A1 (en) 2008-02-14

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Effective date: 20180810