CA2660133C - Thiophenecarboxamide derivatives as ep4 receptor ligands - Google Patents

Thiophenecarboxamide derivatives as ep4 receptor ligands Download PDF

Info

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
Authority
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

Links

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 (en:Method)
EP (1) EP2054401B1 (en:Method)
JP (1) JP5259592B2 (en:Method)
CN (1) CN101541778B (en:Method)
AU (1) AU2007283404B2 (en:Method)
CA (1) CA2660133C (en:Method)
ES (1) ES2421453T3 (en:Method)
WO (1) WO2008017164A1 (en:Method)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5408434B2 (ja) * 2007-07-03 2014-02-05 アステラス製薬株式会社 アミド化合物
AU2008284303A1 (en) * 2007-08-09 2009-02-12 Merck & Co., Inc. Process for making thiophene carboxamide derivative
WO2009139373A1 (ja) * 2008-05-14 2009-11-19 アステラス製薬株式会社 アミド化合物
WO2010019796A1 (en) * 2008-08-14 2010-02-18 Chemietek, Llc Heterocyclic amide derivatives as ep4 receptor antagonists
EP2488168A1 (en) 2009-10-14 2012-08-22 Gemmus Pharma Inc. Combination therapy treatment for viral infections
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
PE20131343A1 (es) 2010-09-21 2013-11-18 Eisai Randd Man Co Ltd Derivados de acido benzoico
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
CN105163761B (zh) * 2013-03-19 2018-12-21 株式会社AskAt Ep4受体拮抗剂在软骨疾病的治疗中的用途
US10391086B2 (en) 2013-03-19 2019-08-27 Askat Inc. Use of EP4 receptor antagonists in the treatment of cartilage disease
SG11201510121RA (en) 2013-06-12 2016-01-28 Kaken Pharma Co Ltd 4-alkynyl imidazole derivative and medicine comprising same as active ingredient
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
US9926262B2 (en) * 2014-06-06 2018-03-27 Allergan, Inc. 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
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
WO2018210987A1 (en) 2017-05-18 2018-11-22 Idorsia Pharmaceuticals Ltd Benzofurane and benzothiophene derivatives as pge2 receptor modulators
EP3625223B1 (en) 2017-05-18 2021-08-11 Idorsia Pharmaceuticals Ltd Pyrimidine derivatives
KR102632028B1 (ko) 2017-05-18 2024-01-31 이도르시아 파마슈티컬스 리미티드 Pge2 수용체 조절제로서의 페닐 유도체
PE20191811A1 (es) 2017-05-18 2019-12-26 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
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
US20230390303A1 (en) 2020-11-13 2023-12-07 Ono Pharmaceutical Co., Ltd. Cancer treatment by combination of ep4 antagonist and 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
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
PL365443A1 (en) * 2001-01-31 2005-01-10 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
WO2005021508A1 (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
AU2005235248A1 (en) * 2004-04-20 2005-11-03 Pfizer Products Inc. Combinations comprising alpha-2-delta ligands and EP4 receptor antagonists
BRPI0510598A (pt) 2004-05-04 2007-11-20 Pfizer compostos de amida de aril ou heteroaril substituìdos
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
EP2054401A4 (en) 2010-10-13
AU2007283404A1 (en) 2008-02-14
CA2660133A1 (en) 2008-02-14
EP2054401A1 (en) 2009-05-06
CN101541778B (zh) 2014-10-08
AU2007283404B2 (en) 2013-04-18
ES2421453T3 (es) 2013-09-02
EP2054401B1 (en) 2013-05-01
JP2010500293A (ja) 2010-01-07
WO2008017164A1 (en) 2008-02-14
US20090247596A1 (en) 2009-10-01
JP5259592B2 (ja) 2013-08-07
CN101541778A (zh) 2009-09-23
US8969394B2 (en) 2015-03-03

Similar Documents

Publication Publication Date Title
CA2660133C (en) Thiophenecarboxamide derivatives as ep4 receptor ligands
CA2679175C (en) Indole and indoline cyclopropyl amide derivatives as ep4 receptor antagonists
US7968578B2 (en) Indole amide derivatives as EP4 receptor antagonists
US7705035B2 (en) Indoline amide derivatives as EP4 receptor ligands
US8003661B2 (en) Naphthalene and quinoline sulfonylurea derivatives as EP4 receptor antagonists
US8013159B2 (en) Quinoline derivatives as EP4 antagonists
JP2012503605A (ja) Ｅｐ４受容体アンタゴニストとしてのベータ−カルボリンスルホニルウレア誘導体
GB2264115A (en) 1h-2-methylimidazo(4,5-c)pyridinyl derivatives as paf antagonists

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20180810