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)
  • 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 (OSRAM)
EP (1) EP2054401B1 (OSRAM)
JP (1) JP5259592B2 (OSRAM)
CN (1) CN101541778B (OSRAM)
AU (1) AU2007283404B2 (OSRAM)
CA (1) CA2660133C (OSRAM)
ES (1) ES2421453T3 (OSRAM)
WO (1) WO2008017164A1 (OSRAM)

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EP2460787A1 (en) * 2007-07-03 2012-06-06 Astellas Pharma Inc. Amide compounds and their use as PGE2 antagonists.
US20100204487A1 (en) * 2007-08-09 2010-08-12 Ian Davies Process for making thiophene carboxamide derivatives
RU2479576C9 (ru) 2008-05-14 2014-03-10 Астеллас Фарма Инк. Амидное соединение
EP2320906B1 (en) * 2008-08-14 2016-02-24 Beta Pharma Canada Inc. Heterocyclic amide derivatives as ep4 receptor antagonists
KR20120093955A (ko) 2009-10-14 2012-08-23 젬머스 파마 인코포레이티드 바이러스 감염에 대한 병용 요법 치료
CN102770159A (zh) * 2010-02-22 2012-11-07 拉夸里亚创药株式会社 Ep-4受体拮抗剂在治疗il-23介导疾病中的用途
SMT201700008T1 (it) 2010-09-21 2017-03-08 Eisai R&D Man Co Ltd Composizione farmaceutica
ES2545110T3 (es) 2010-12-10 2015-09-08 Rottapharm Biotech S.R.L. Derivados de piridinamida como antagonistas del receptor EP4
UA115576C2 (uk) 2012-12-06 2017-11-27 Байєр Фарма Акцієнгезелльшафт Похідні бензимідазолу як антагоністи ер4
US10391086B2 (en) 2013-03-19 2019-08-27 Askat Inc. Use of EP4 receptor antagonists in the treatment of cartilage disease
BR112015023663A2 (pt) * 2013-03-19 2020-10-20 Askat Inc. uso de um composto com atividade antagonística de ep4 ou um sal farmaceuticamente aceitável deste, uso de um composto da fórmula (i), (ii), (iii), (iv), (va) ou (vb) ou um sal farmaceuticamente aceitável deste, composição farmacêutica para o tratamento de doença de cartilagem, método para o tratamento de doenças de cartilagem em um indivíduo animal, incluindo um indivíduo mamífero e composto da fórmula (i), (ii),(iii), (iv), (va) ou (vb) ou um sal farmaceuticamente aceitável deste
HUE039015T2 (hu) 2013-06-12 2018-12-28 Kaken Pharma Co Ltd 4-Alkinil-imidazol-származék és ezt hatóanyagként tartalmazó gyógyszerkészítmény
JP6694385B2 (ja) 2013-08-09 2020-05-13 アーデリクス，インコーポレーテッド リン酸塩輸送阻害のための化合物及び方法
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
CN110354266A (zh) * 2014-05-23 2019-10-22 卫材 R&D 管理有限公司 用于治疗癌症的组合疗法
TR201905436T4 (tr) * 2014-06-06 2019-05-21 Allergan Inc Terapötik bileşikler olarak yeni ep4 agonistleri.
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
WO2018210992A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Pyrimidine derivatives
AU2018268311B2 (en) 2017-05-18 2022-02-10 Idorsia Pharmaceuticals Ltd Pyrimidine derivatives as PGE2 receptor modulators
EP3625224B1 (en) 2017-05-18 2021-08-04 Idorsia Pharmaceuticals Ltd N-substituted indole derivatives
US11325899B2 (en) 2017-05-18 2022-05-10 Idorsia Pharmaceuticals Ltd Benzofurane and benzothiophene derivatives as PGE2 receptor modulators
WO2018210994A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Phenyl derivatives as pge2 receptor modulators
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
EP3972599B1 (en) 2019-05-21 2025-10-22 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
BR112023002660A2 (pt) * 2020-08-18 2023-03-14 Hutchison Medipharma Ltd Compostos de pirimidinona e usos dos mesmos
WO2022102731A1 (ja) 2020-11-13 2022-05-19 小野薬品工業株式会社 Ｅｐ４拮抗薬と免疫チェックポイント阻害物質との併用によるがん治療

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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
DE69635254T2 (de) * 1995-07-07 2006-07-13 Astrazeneca Ab Ortho-substituierte aromatische Verbindungen, die drei (Het)aryl-Ringe enthalten, deren Herstellung und deren Verwendung als Prostaglandin-E2-(PGE2)-Antagonisten
CA2436551A1 (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
CA2536870C (en) * 2003-09-03 2009-10-27 Pfizer Inc. Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists
GB0324269D0 (en) * 2003-10-16 2003-11-19 Pharmagene Lab Ltd EP4 receptor antagonists
RU2006137076A (ru) * 2004-04-20 2008-04-27 Пфайзер Продактс Инк. (Us) Комбинации, содержащие лиганды рецептора альфа-2-дельта
CN1950333A (zh) * 2004-05-04 2007-04-18 辉瑞大药厂 取代的甲基芳基或杂芳基酰胺化合物
EP1756043B1 (en) * 2004-05-04 2009-07-01 RaQualia Pharma 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
EP2054401A4 (en) 2010-10-13
CN101541778B (zh) 2014-10-08
JP2010500293A (ja) 2010-01-07
AU2007283404A1 (en) 2008-02-14
CA2660133A1 (en) 2008-02-14
CN101541778A (zh) 2009-09-23
AU2007283404B2 (en) 2013-04-18
EP2054401B1 (en) 2013-05-01
US8969394B2 (en) 2015-03-03
ES2421453T3 (es) 2013-09-02
EP2054401A1 (en) 2009-05-06
JP5259592B2 (ja) 2013-08-07
WO2008017164A1 (en) 2008-02-14
US20090247596A1 (en) 2009-10-01

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Effective date: 20180810