CN101541778B - 作为ep4受体配体的噻吩甲酰胺衍生物 - Google Patents
作为ep4受体配体的噻吩甲酰胺衍生物 Download PDFInfo
- Publication number
- CN101541778B CN101541778B CN200780037574.4A CN200780037574A CN101541778B CN 101541778 B CN101541778 B CN 101541778B CN 200780037574 A CN200780037574 A CN 200780037574A CN 101541778 B CN101541778 B CN 101541778B
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- alkyl
- compounds
- methyl
- 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
Links
- 0 CC(NS(*)(=O)=O)=O Chemical compound CC(NS(*)(=O)=O)=O 0.000 description 2
- QKXHUJWMBUCTPH-UHFFFAOYSA-N CC(c(cc1)ccc1-c1nccnn1)NC(c([s]1)c(CC2=CC(C3)C3C(Cl)=C2)cc1Cl)O Chemical compound CC(c(cc1)ccc1-c1nccnn1)NC(c([s]1)c(CC2=CC(C3)C3C(Cl)=C2)cc1Cl)O QKXHUJWMBUCTPH-UHFFFAOYSA-N 0.000 description 1
- KECPRZHCNCDSET-UHFFFAOYSA-N CC(c(cc1)ccc1Br)NC(OC(C)(C)C)=O Chemical compound CC(c(cc1)ccc1Br)NC(OC(C)(C)C)=O KECPRZHCNCDSET-UHFFFAOYSA-N 0.000 description 1
- LEDRUOYYPNYUKR-UHFFFAOYSA-N CC(c(cc1)ccc1C(NS(C)(=O)=O)=O)NC(c1c(C)[s]c(C)c1CC1C=CC(C(F)(F)F)=CC1C)=O Chemical compound CC(c(cc1)ccc1C(NS(C)(=O)=O)=O)NC(c1c(C)[s]c(C)c1CC1C=CC(C(F)(F)F)=CC1C)=O LEDRUOYYPNYUKR-UHFFFAOYSA-N 0.000 description 1
- OKRPFRUXMOYTDV-UHFFFAOYSA-N CC(c(cc1)ccc1C(O)=O)NC(OC(C)(C)C)=O Chemical compound CC(c(cc1)ccc1C(O)=O)NC(OC(C)(C)C)=O OKRPFRUXMOYTDV-UHFFFAOYSA-N 0.000 description 1
- OKXWTILSPGNEBA-UHFFFAOYSA-N CCCc1ccc(C(F)(F)F)cc1 Chemical compound CCCc1ccc(C(F)(F)F)cc1 OKXWTILSPGNEBA-UHFFFAOYSA-N 0.000 description 1
- PXNRSYKOHWZGSK-UHFFFAOYSA-N Cc1cc(Cc2ccc(C(F)(F)F)cc2)c(C)[s]1 Chemical compound Cc1cc(Cc2ccc(C(F)(F)F)cc2)c(C)[s]1 PXNRSYKOHWZGSK-UHFFFAOYSA-N 0.000 description 1
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)
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 |
|---|---|
| CN101541778A CN101541778A (zh) | 2009-09-23 |
| CN101541778B true CN101541778B (zh) | 2014-10-08 |
Family
ID=39032586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200780037574.4A Expired - Fee Related CN101541778B (zh) | 2006-08-11 | 2007-08-10 | 作为ep4受体配体的噻吩甲酰胺衍生物 |
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005021508A1 (en) * | 2003-09-03 | 2005-03-10 | Pfizer Inc. | Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists |
| WO2005102389A2 (en) * | 2004-04-20 | 2005-11-03 | Pfizer Products Inc. | Combinations comprising alpha-2-delta ligands and ep4 receptor antagonists |
| WO2005105732A1 (en) * | 2004-05-04 | 2005-11-10 | Pfizer Japan Inc. | Substituted methyl aryl or heteroaryl amide compounds |
| WO2005105733A1 (en) * | 2004-05-04 | 2005-11-10 | Pfizer Japan 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 |
Family Cites Families (5)
| 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 |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
-
2007
- 2007-08-10 CN CN200780037574.4A patent/CN101541778B/zh not_active Expired - Fee Related
- 2007-08-10 US US12/309,941 patent/US8969394B2/en active Active
- 2007-08-10 EP EP07815782.3A patent/EP2054401B1/en active Active
- 2007-08-10 WO PCT/CA2007/001404 patent/WO2008017164A1/en not_active Ceased
- 2007-08-10 JP JP2009523120A patent/JP5259592B2/ja not_active Expired - Fee Related
- 2007-08-10 CA CA2660133A patent/CA2660133C/en not_active Expired - Fee Related
- 2007-08-10 ES ES07815782T patent/ES2421453T3/es active Active
- 2007-08-10 AU AU2007283404A patent/AU2007283404B2/en not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005021508A1 (en) * | 2003-09-03 | 2005-03-10 | Pfizer Inc. | Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists |
| WO2005102389A2 (en) * | 2004-04-20 | 2005-11-03 | Pfizer Products Inc. | Combinations comprising alpha-2-delta ligands and ep4 receptor antagonists |
| WO2005105732A1 (en) * | 2004-05-04 | 2005-11-10 | Pfizer Japan Inc. | Substituted methyl aryl or heteroaryl amide compounds |
| WO2005105733A1 (en) * | 2004-05-04 | 2005-11-10 | Pfizer Japan 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 |
| 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 |
| CA2660133C (en) | 2015-10-27 |
| CA2660133A1 (en) | 2008-02-14 |
| AU2007283404A1 (en) | 2008-02-14 |
| WO2008017164A1 (en) | 2008-02-14 |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent for invention or patent application | ||
| CB02 | Change of applicant information |
Address after: Quebec Applicant after: Merck Canada Inc. Address before: Quebec Applicant before: Merck Frosst Canada Ltd. |
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| COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: MERCK FROSST CANADA LTD. TO: MERCK (CANADA) CO., LTD. |
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20141008 Termination date: 20170810 |
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| CF01 | Termination of patent right due to non-payment of annual fee |