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
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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 (cg-RX-API-DMAC7.html)
EP (1) EP2054401B1 (cg-RX-API-DMAC7.html)
JP (1) JP5259592B2 (cg-RX-API-DMAC7.html)
CN (1) CN101541778B (cg-RX-API-DMAC7.html)
AU (1) AU2007283404B2 (cg-RX-API-DMAC7.html)
CA (1) CA2660133C (cg-RX-API-DMAC7.html)
ES (1) ES2421453T3 (cg-RX-API-DMAC7.html)
WO (1) WO2008017164A1 (cg-RX-API-DMAC7.html)

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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
JP5536773B2 (ja) * 2008-08-14 2014-07-02 ベータ・ファーマ・カナダ・インコーポレイテッド Ｅｐ４受容体アンタゴニストとしてのヘテロ環式アミド誘導体
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
CA2789665C (en) * 2010-02-22 2020-06-16 Raqualia Pharma Inc. Use of ep4 receptor antagonists in the treatment of il-23 mediated diseases
JP5956448B2 (ja) 2010-09-21 2016-07-27 エーザイ・アール・アンド・ディー・マネジメント株式会社 医薬組成物
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
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
US10391086B2 (en) 2013-03-19 2019-08-27 Askat Inc. Use of EP4 receptor antagonists in the treatment of cartilage disease
LT3009426T (lt) 2013-06-12 2018-07-25 Kaken Pharmaceutical Co., Ltd. 4-alkinilimidazolo darinys ir jį, kaip veiklųjį ingredientą, apimantis vaistas
CA2920856A1 (en) 2013-08-09 2015-02-12 Ardelyx, Inc. Ph modulating compounds for inhibiting gastrointestinal phosphate uptake
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
WO2015179615A1 (en) * 2014-05-23 2015-11-26 Eisai R&D Management Co., Ltd Combination therapies for the treatment of cancer
RU2016150902A (ru) * 2014-06-06 2018-07-17 Аллерган, Инк. Новые агонисты ep4 в качестве терапевтических соединений
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
KR102626982B1 (ko) 2017-05-18 2024-01-18 이도르시아 파마슈티컬스 리미티드 Pge2 수용체 조절제로서의 피리미딘 유도체
PE20191787A1 (es) 2017-05-18 2019-12-24 Idorsia Pharmaceuticals Ltd Derivados de indol n-sustituidos
CA3063632A1 (en) 2017-05-18 2018-11-22 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
ES2896476T3 (es) 2017-05-18 2022-02-24 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
CN114340631A (zh) 2019-05-21 2022-04-12 阿德利克斯股份有限公司 用于降低患者的血清磷酸盐的组合
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
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

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US5834468A (en) * 1995-07-07 1998-11-10 Zeneca Limited Substituted aryl and heteroaryl compounds as E-type prostaglandin antagonists
IL156412A0 (en) * 2001-01-31 2004-01-04 Pfizer Prod 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
AU2004268839A1 (en) * 2003-09-03 2005-03-10 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
CN1946391A (zh) * 2004-04-20 2007-04-11 辉瑞产品公司 包含α－2－δ配体的组合
ES2327760T3 (es) 2004-05-04 2009-11-03 Raqualia Pharma Inc Compuestos de aril-heteroaril-amida ortosustituidos.
KR20070006891A (ko) * 2004-05-04 2007-01-11 화이자 인코포레이티드 치환된 메틸 아릴 또는 헤테로아릴 아미드 화합물
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
AU2007283404A1 (en) 2008-02-14
JP2010500293A (ja) 2010-01-07
US20090247596A1 (en) 2009-10-01
EP2054401B1 (en) 2013-05-01
CN101541778B (zh) 2014-10-08
WO2008017164A1 (en) 2008-02-14
EP2054401A1 (en) 2009-05-06
ES2421453T3 (es) 2013-09-02
CN101541778A (zh) 2009-09-23
JP5259592B2 (ja) 2013-08-07
EP2054401A4 (en) 2010-10-13
CA2660133A1 (en) 2008-02-14
US8969394B2 (en) 2015-03-03
AU2007283404B2 (en) 2013-04-18

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Effective date: 20180810