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)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (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)

Families Citing this family (31)

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EP2460787A1 (en) * 2007-07-03 2012-06-06 Astellas Pharma Inc. Amide compounds and their use as PGE2 antagonists.
AU2008284303A1 (en) * 2007-08-09 2009-02-12 Merck & Co., Inc. Process for making thiophene carboxamide derivative
EP2565191B1 (en) 2008-05-14 2014-10-08 Astellas Pharma Inc. 4-(Indol-7-ylcarbonylaminomethyl)cyclohexanecarboxylic acid derivatives as EP4 receptor antagonists useful for the treatment of chronic renal failure or diabetic nephropathy
US8404736B2 (en) * 2008-08-14 2013-03-26 Beta Pharma Canada Inc. Heterocyclic amide derivatives as EP4 receptor antagonists
US20120190637A1 (en) 2009-10-14 2012-07-26 Gemmus Pharma, Inc. Combination therapy treatment for viral infections
US9457084B2 (en) * 2010-02-22 2016-10-04 Raqualia Pharma Inc. Use of EP4 receptor antagonists in the treatment of IL-23 mediated diseases
PT2619182T (pt) 2010-09-21 2017-01-17 Eisai R&D Man Co Ltd Composição farmacêutica
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
HK1220386A1 (zh) 2013-03-19 2017-05-05 Askat Inc. Ep4受体拮抗剂在软骨疾病的治疗中的用途
CN105431416B (zh) 2013-06-12 2019-01-08 科研制药株式会社 4-炔基咪唑衍生物和含有其作为有效成分的药物
WO2015021358A2 (en) 2013-08-09 2015-02-12 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
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
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
SI3625224T1 (sl) 2017-05-18 2021-11-30 Idorsia Pharmaceuticals Ltd N-substituirani indolni derivati
WO2018210988A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Pyrimidine derivatives as pge2 receptor modulators
WO2018210992A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Pyrimidine derivatives
JP7093791B2 (ja) 2017-05-18 2022-06-30 イドーシア ファーマシューティカルズ リミテッド Ｐｇｅ２レセプター調節剤としてのベンゾフラン及びベンゾチオフェン誘導体
MA49126B1 (fr) 2017-05-18 2021-10-29 Idorsia Pharmaceuticals Ltd Dérivés de phényle utilisés en tant que modulateurs des récepteurs des 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
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
WO2022037585A1 (en) * 2020-08-18 2022-02-24 Hutchison Medipharma Limited Pyrimidinone compounds and uses thereof
TW202228674A (zh) 2020-11-13 2022-08-01 日商小野藥品工業股份有限公司 藉由併用ｅｐ４拮抗藥與免疫檢查點抑制物質而進行之癌症治療

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
EP0752421B1 (en) 1995-07-07 2005-10-12 AstraZeneca AB Ortho-substituted aromatic compounds, containing three (het)aryl moieties, their preparation and their use as prostaglandin E2-(PGE2)-antagonists
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
ES2441206T3 (es) 2003-09-03 2014-02-03 Raqualia Pharma Inc. Compuestos de fenil o piridilamida como antagonistas de la prostaglandina E2
GB0324269D0 (en) 2003-10-16 2003-11-19 Pharmagene Lab Ltd EP4 receptor antagonists
MXPA06012172A (es) 2004-04-20 2007-01-17 Pfizer Prod Inc Combinaciones que comprenden ligandos alfa-2-delta y antagonistas del receptor ep4.
ATE435198T1 (de) * 2004-05-04 2009-07-15 Raqualia Pharma Inc Orthosubstituierte aryl- oder heteroarylamidverbindungen
CA2565813C (en) * 2004-05-04 2010-10-26 Pfizer Inc. Substituted methyl 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
US20090247596A1 (en) 2009-10-01
EP2054401A4 (en) 2010-10-13
AU2007283404B2 (en) 2013-04-18
EP2054401A1 (en) 2009-05-06
CN101541778B (zh) 2014-10-08
US8969394B2 (en) 2015-03-03
WO2008017164A1 (en) 2008-02-14
JP2010500293A (ja) 2010-01-07
EP2054401B1 (en) 2013-05-01
AU2007283404A1 (en) 2008-02-14
JP5259592B2 (ja) 2013-08-07
CA2660133A1 (en) 2008-02-14
CN101541778A (zh) 2009-09-23
ES2421453T3 (es) 2013-09-02

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Effective date: 20180810