JP5259592B2 - Ep4受容体リガンドとしてのチオフェンカルボキサミド誘導体 - Google Patents
Ep4受容体リガンドとしてのチオフェンカルボキサミド誘導体 Download PDFInfo
- Publication number
- JP5259592B2 JP5259592B2 JP2009523120A JP2009523120A JP5259592B2 JP 5259592 B2 JP5259592 B2 JP 5259592B2 JP 2009523120 A JP2009523120 A JP 2009523120A JP 2009523120 A JP2009523120 A JP 2009523120A JP 5259592 B2 JP5259592 B2 JP 5259592B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- group
- acceptable salt
- 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
Links
- 0 CBc1c(C(NC(*)(*)c2ccc(*)cc2)=O)[s]c(*)c1* Chemical compound CBc1c(C(NC(*)(*)c2ccc(*)cc2)=O)[s]c(*)c1* 0.000 description 3
- PYWZJCKVQWUVPO-UHFFFAOYSA-N CC(c(cc1)ccc1-c1n[nH]nn1)NC(c([s]1)c(Cc2cc(Cl)ccc2)cc1Cl)=O Chemical compound CC(c(cc1)ccc1-c1n[nH]nn1)NC(c([s]1)c(Cc2cc(Cl)ccc2)cc1Cl)=O PYWZJCKVQWUVPO-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
- FADNAZBPTQVMPQ-ZDUSSCGKSA-N C[C@@H](c(cc1)ccc1C(O)=O)NC(c1c(C)[s]c(C)c1Cc(cc1)ccc1Cl)=O Chemical compound C[C@@H](c(cc1)ccc1C(O)=O)NC(c1c(C)[s]c(C)c1Cc(cc1)ccc1Cl)=O FADNAZBPTQVMPQ-ZDUSSCGKSA-N 0.000 description 1
- NWYUIYYDNDZXBK-UHFFFAOYSA-N Cc([s]c(C)c1Br)c1Br Chemical compound Cc([s]c(C)c1Br)c1Br NWYUIYYDNDZXBK-UHFFFAOYSA-N 0.000 description 1
- NNNHDNZOOJUIKG-UHFFFAOYSA-N Cc1c(Cc2cc(C(F)(F)F)ccc2)c(C(NC2(CC2)c(cc2)ccc2C(N=N[NH+]2[O-])=[N+]2[O-])=O)c(C)[s]1 Chemical compound Cc1c(Cc2cc(C(F)(F)F)ccc2)c(C(NC2(CC2)c(cc2)ccc2C(N=N[NH+]2[O-])=[N+]2[O-])=O)c(C)[s]1 NNNHDNZOOJUIKG-UHFFFAOYSA-N 0.000 description 1
- BEWXZMDKZCMEJP-UHFFFAOYSA-N Cc1c(Cc2ccc(C(F)(F)F)cc2)c(C(NC2(CC2)c(cc2)ccc2C#N)=O)c(C)[s]1 Chemical compound Cc1c(Cc2ccc(C(F)(F)F)cc2)c(C(NC2(CC2)c(cc2)ccc2C#N)=O)c(C)[s]1 BEWXZMDKZCMEJP-UHFFFAOYSA-N 0.000 description 1
- BMYCTTRDGGWIPP-UHFFFAOYSA-N Cc1c(Cc2ccc(C(F)(F)F)cc2)c(C(NC2(CC2)c(cc2)ccc2C(N=N[NH+]2[O-])=[N+]2[O-])=O)c(C)[s]1 Chemical compound Cc1c(Cc2ccc(C(F)(F)F)cc2)c(C(NC2(CC2)c(cc2)ccc2C(N=N[NH+]2[O-])=[N+]2[O-])=O)c(C)[s]1 BMYCTTRDGGWIPP-UHFFFAOYSA-N 0.000 description 1
- WBADBJDOSDVJBE-UHFFFAOYSA-N Cc1c(Cc2ccc(C(F)(F)F)cc2)c(C(O)=O)c(C)[s]1 Chemical compound Cc1c(Cc2ccc(C(F)(F)F)cc2)c(C(O)=O)c(C)[s]1 WBADBJDOSDVJBE-UHFFFAOYSA-N 0.000 description 1
- DDAZHNWCORZWHX-UHFFFAOYSA-N Clc([s]1)c(C(c2cccc(Cl)c2)OC2OCCCC2)c(Br)c1Cl Chemical compound Clc([s]1)c(C(c2cccc(Cl)c2)OC2OCCCC2)c(Br)c1Cl DDAZHNWCORZWHX-UHFFFAOYSA-N 0.000 description 1
- HBYGBJDMFWFILO-UHFFFAOYSA-N OC(c(c(C(c1cc(Cl)ccc1)OC1OCCCC1)c([s]1)Cl)c1Cl)=O Chemical compound OC(c(c(C(c1cc(Cl)ccc1)OC1OCCCC1)c([s]1)Cl)c1Cl)=O HBYGBJDMFWFILO-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)
- 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)
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2010500293A JP2010500293A (ja) | 2010-01-07 |
| JP2010500293A5 JP2010500293A5 (en:Method) | 2010-09-16 |
| JP5259592B2 true JP5259592B2 (ja) | 2013-08-07 |
Family
ID=39032586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009523120A Expired - Fee Related JP5259592B2 (ja) | 2006-08-11 | 2007-08-10 | Ep4受容体リガンドとしてのチオフェンカルボキサミド誘導体 |
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)
| 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)
| 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 |
-
2007
- 2007-08-10 AU AU2007283404A patent/AU2007283404B2/en not_active Ceased
- 2007-08-10 JP JP2009523120A patent/JP5259592B2/ja not_active Expired - Fee Related
- 2007-08-10 EP EP07815782.3A patent/EP2054401B1/en active Active
- 2007-08-10 US US12/309,941 patent/US8969394B2/en active Active
- 2007-08-10 WO PCT/CA2007/001404 patent/WO2008017164A1/en not_active Ceased
- 2007-08-10 ES ES07815782T patent/ES2421453T3/es active Active
- 2007-08-10 CN CN200780037574.4A patent/CN101541778B/zh not_active Expired - Fee Related
- 2007-08-10 CA CA2660133A patent/CA2660133C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2054401A4 (en) | 2010-10-13 |
| CA2660133C (en) | 2015-10-27 |
| 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 |
| CN101541778A (zh) | 2009-09-23 |
| US8969394B2 (en) | 2015-03-03 |
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