JP2005509632A5 - - Google Patents
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- Publication number
- JP2005509632A5 JP2005509632A5 JP2003537631A JP2003537631A JP2005509632A5 JP 2005509632 A5 JP2005509632 A5 JP 2005509632A5 JP 2003537631 A JP2003537631 A JP 2003537631A JP 2003537631 A JP2003537631 A JP 2003537631A JP 2005509632 A5 JP2005509632 A5 JP 2005509632A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- group
- ethyl
- oxopyrazolidin
- benzoic acid
- 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.)
- Granted
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 9
- 241000124008 Mammalia Species 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims 8
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims 7
- 239000005711 Benzoic acid Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 235000010233 benzoic acid Nutrition 0.000 claims 6
- 125000002837 carbocyclic group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 3
- 125000002723 alicyclic group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000035558 fertility Effects 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000004118 muscle contraction Effects 0.000 claims 2
- -1 1-ethylcyclobutyl Chemical group 0.000 claims 1
- SIGCFCMKKRESGW-UHFFFAOYSA-N 4-[2-[2-(3-cyclobutyl-3-hydroxypropyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C1CCC1C(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 SIGCFCMKKRESGW-UHFFFAOYSA-N 0.000 claims 1
- JVPGVILOMSPMMY-UHFFFAOYSA-N 4-[2-[2-(3-hydroxy-4-phenylbutyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C=1C=CC=CC=1CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 JVPGVILOMSPMMY-UHFFFAOYSA-N 0.000 claims 1
- FXEVKFYZRMILMZ-UHFFFAOYSA-N 4-[2-[2-(3-hydroxy-5-methylhexyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CC(C)CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 FXEVKFYZRMILMZ-UHFFFAOYSA-N 0.000 claims 1
- PAVYSSGJRYCIIJ-UHFFFAOYSA-N 4-[2-[2-(3-hydroxyoctyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCCCC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 PAVYSSGJRYCIIJ-UHFFFAOYSA-N 0.000 claims 1
- UFNLOWRQRUZWKF-UHFFFAOYSA-N 4-[2-[2-(4-ethyl-4-hydroxyoctyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCCC(O)(CC)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 UFNLOWRQRUZWKF-UHFFFAOYSA-N 0.000 claims 1
- CALFSRIGIOMZFM-UHFFFAOYSA-N 4-[2-[2-(4-hydroxy-4,7-dimethyloctyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CC(C)CCC(C)(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 CALFSRIGIOMZFM-UHFFFAOYSA-N 0.000 claims 1
- LBGUNFMRRVJPSG-UHFFFAOYSA-N 4-[2-[2-(4-hydroxy-4-methylheptyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCC(C)(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 LBGUNFMRRVJPSG-UHFFFAOYSA-N 0.000 claims 1
- ZLJYTBPSXYKRKL-UHFFFAOYSA-N 4-[2-[2-(4-hydroxy-5-methyloctyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCC(C)C(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 ZLJYTBPSXYKRKL-UHFFFAOYSA-N 0.000 claims 1
- INOWIYUOGGMVDM-UHFFFAOYSA-N 4-[2-[2-(4-hydroxy-6-methylheptyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CC(C)CC(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 INOWIYUOGGMVDM-UHFFFAOYSA-N 0.000 claims 1
- XZWDACYVXIULCX-UHFFFAOYSA-N 4-[2-[2-(4-hydroxynonyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCCCC(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 XZWDACYVXIULCX-UHFFFAOYSA-N 0.000 claims 1
- LTKCOAAEGIFTID-UHFFFAOYSA-N 4-[2-[2-(4-hydroxyoctyl)-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCCC(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 LTKCOAAEGIFTID-UHFFFAOYSA-N 0.000 claims 1
- KEQOYEUKTHDSDS-FNORWQNLSA-N 4-[2-[2-[(e)-4-hydroxynon-2-enyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCCCC(O)\C=C\CN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 KEQOYEUKTHDSDS-FNORWQNLSA-N 0.000 claims 1
- KEQOYEUKTHDSDS-ALCCZGGFSA-N 4-[2-[2-[(z)-4-hydroxynon-2-enyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CCCCCC(O)\C=C/CN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 KEQOYEUKTHDSDS-ALCCZGGFSA-N 0.000 claims 1
- KDVFFCPULSQTQN-UHFFFAOYSA-N 4-[2-[2-[3-hydroxy-4-(3-iodophenyl)butyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C=1C=CC(I)=CC=1CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 KDVFFCPULSQTQN-UHFFFAOYSA-N 0.000 claims 1
- KALXDWPKUYNCLA-UHFFFAOYSA-N 4-[2-[2-[3-hydroxy-4-(3-methylphenyl)butyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound CC1=CC=CC(CC(O)CCN2N(C(=O)CC2)CCC=2C=CC(=CC=2)C(O)=O)=C1 KALXDWPKUYNCLA-UHFFFAOYSA-N 0.000 claims 1
- UCAFZBFLCPWPLH-UHFFFAOYSA-N 4-[2-[2-[3-hydroxy-4-[3-(trifluoromethyl)phenyl]butyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 UCAFZBFLCPWPLH-UHFFFAOYSA-N 0.000 claims 1
- NJNRRASCYIZRMY-UHFFFAOYSA-N 4-[2-[2-[4-(1,3-benzodioxol-5-yl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C=1C=C2OCOC2=CC=1CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 NJNRRASCYIZRMY-UHFFFAOYSA-N 0.000 claims 1
- MMKYRZFPISEJKE-UHFFFAOYSA-N 4-[2-[2-[4-(3-bromophenyl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C=1C=CC(Br)=CC=1CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 MMKYRZFPISEJKE-UHFFFAOYSA-N 0.000 claims 1
- HVIXFTUMIDKUHX-UHFFFAOYSA-N 4-[2-[2-[4-(3-chlorophenyl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C=1C=CC(Cl)=CC=1CC(O)CCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 HVIXFTUMIDKUHX-UHFFFAOYSA-N 0.000 claims 1
- GNZZMSRREAKILT-UHFFFAOYSA-N 4-[2-[2-[4-[1-(cyclopropylmethyl)cyclobutyl]-4-hydroxybutyl]-5-oxopyrazolidin-1-yl]ethyl]benzoic acid Chemical compound C1CCC1(CC1CC1)C(O)CCCN1CCC(=O)N1CCC1=CC=C(C(O)=O)C=C1 GNZZMSRREAKILT-UHFFFAOYSA-N 0.000 claims 1
- 208000005171 Dysmenorrhea Diseases 0.000 claims 1
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 1
- 208000027004 Eosinophilic disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims 1
- 102000008866 Prostaglandin E receptors Human genes 0.000 claims 1
- 108010088540 Prostaglandin E receptors Proteins 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- 230000035800 maturation Effects 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33604801P | 2001-10-23 | 2001-10-23 | |
| PCT/US2002/033964 WO2003035064A1 (en) | 2001-10-23 | 2002-10-23 | Pyrazolidinone compounds as ligands of the prostaglandin ep2 and/or ep4 receptors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005509632A JP2005509632A (ja) | 2005-04-14 |
| JP2005509632A5 true JP2005509632A5 (enExample) | 2006-01-05 |
| JP4550417B2 JP4550417B2 (ja) | 2010-09-22 |
Family
ID=23314338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003537631A Expired - Fee Related JP4550417B2 (ja) | 2001-10-23 | 2002-10-23 | プロスタグランジンｅｐ２及び／又はｅｐ４受容体のリガンドとしてのポリアゾリジノン化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7410991B2 (enExample) |
| EP (1) | EP1439837B1 (enExample) |
| JP (1) | JP4550417B2 (enExample) |
| AT (1) | ATE391503T1 (enExample) |
| AU (1) | AU2002340282B2 (enExample) |
| CA (1) | CA2463102C (enExample) |
| DE (1) | DE60226051T2 (enExample) |
| ES (1) | ES2305310T3 (enExample) |
| IL (2) | IL161581A0 (enExample) |
| WO (1) | WO2003035064A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2465537B1 (en) | 2002-10-10 | 2016-06-29 | ONO Pharmaceutical Co., Ltd. | Microspheres comprising ONO-1301 |
| JP5014978B2 (ja) * | 2005-01-27 | 2012-08-29 | 旭化成ファーマ株式会社 | ヘテロ６員環化合物及びその用途 |
| US7531533B2 (en) | 2005-01-27 | 2009-05-12 | Asahi Kasei Pharma Corporation | 6-Membered heterocyclic compound and use thereof |
| US7893107B2 (en) | 2005-11-30 | 2011-02-22 | Allergan, Inc. | Therapeutic methods using prostaglandin EP4 agonist components |
| US7557095B2 (en) * | 2006-05-12 | 2009-07-07 | Allergan, Inc. | Therapeutic compounds |
| JP2010500976A (ja) * | 2006-08-09 | 2010-01-14 | アラーガン インコーポレイテッド | 治療用アミド類および関連化合物 |
| US7507833B2 (en) * | 2006-08-10 | 2009-03-24 | Allergan, Inc. | Therapeutic N-aryl or N-heteroaryl pyrazolidine and pyrazolidinone derivatives |
| EP2147672A4 (en) | 2007-05-08 | 2011-11-02 | Nat University Corp Hamamatsu University School Of Medicine | CYTOTOXIC T CELL ACTIVATOR WITH AN EP4 AGONIST |
| EP2003118A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Zimtsäurederivate als Modulatoren des EP2-Rezeptors |
| EP2002834A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryl/Hetarylamide als Modulatoren des EP2-Rezeptors |
| EP2002838A1 (de) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma AG | Verwendung von Aryl/Hetarylamid-Derivaten als Modulatoren des EP2-Rezeptors |
| EP2014287A1 (de) * | 2007-06-13 | 2009-01-14 | Bayer Schering Pharma Aktiengesellschaft | Verwendung von Zimtsäurederivaten als Modulatoren des EP2-Rezeptors |
| CN102089285A (zh) * | 2008-05-09 | 2011-06-08 | 阿勒根公司 | 治疗性的n-芳基或n-杂芳基吡唑烷和吡唑烷酮衍生物 |
| EP2149552A1 (de) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma AG | 5,6 substituierte Benzamid-Derivate als Modulatoren des EP2-Rezeptors |
| EP2149554A1 (de) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma Aktiengesellschaft | Indolylamide als Modulatoren des EP2-Rezeptors |
| EP2149551A1 (de) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma AG | N-(Indol-3-ylalkyl)-(hetero)arylamidderivate als Modulatoren des EP2-Rezeptors |
| JP2013529184A (ja) * | 2010-04-08 | 2013-07-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｐｄｅ４阻害剤及びｅｐ４受容体アンタゴニストを含有する医薬の組み合わせ |
| EP2555774B1 (de) * | 2010-04-08 | 2015-10-21 | Boehringer Ingelheim International GmbH | Arnzeimittelkombinationen enthaltend pde4-inhibitoren und ep4-rezeptor-antagonisten |
| TW201326154A (zh) | 2011-11-28 | 2013-07-01 | 拜耳知識產權公司 | 作為ｅｐ２受體拮抗劑之新穎２ｈ－吲唑 |
| NZ704171A (en) | 2012-07-19 | 2017-10-27 | Cayman Chemical Co Inc | Difluorolactam compositions for ep4-mediated osteo related diseases and conditions |
| US20150272874A1 (en) | 2012-10-29 | 2015-10-01 | Cardio Incorporated | Pulmonary disease-specific therapeutic agent |
| EA201591793A1 (ru) | 2013-03-15 | 2016-01-29 | Кайман Кемикал Компани, Инк. | Лактамные соединения в качестве селективных агонистов ep4-рецепторов для применения при лечении опосредованных ep4 заболеваний и состояний |
| US9676712B2 (en) | 2013-03-15 | 2017-06-13 | Cayman Chemical Company, Inc. | Lactam compounds as EP4 receptor-selective agonists for use in the treatment of EP4-mediated diseases and conditions |
| CA2910398A1 (en) | 2013-07-19 | 2015-01-22 | Cayman Chemical Company, Inc. | Methods, systems, and compositions for promoting bone growth |
| JP6449166B2 (ja) | 2013-10-15 | 2019-01-09 | 小野薬品工業株式会社 | 薬剤溶出性ステントグラフト |
| KR102446027B1 (ko) | 2017-12-25 | 2022-09-21 | 아사히 가세이 파마 가부시키가이샤 | 함질소 6원환 화합물 |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| US12304897B2 (en) | 2019-01-31 | 2025-05-20 | Kyorin Pharmaceutical Co., Ltd. | 15-PGDH inhibitors |
| GB202211234D0 (en) * | 2022-08-02 | 2022-09-14 | Heptares Therapeutics Ltd | Prostaglandin EP4 receptor agonist compounds |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2323193A1 (de) | 1972-05-10 | 1973-11-22 | Du Pont | Pyrazolidinone |
| US3873566A (en) * | 1973-02-28 | 1975-03-25 | Du Pont | 3-Pyrazolidinones and pyrazolidines |
| DE2451160A1 (de) * | 1973-10-30 | 1975-05-07 | Du Pont | 3-pyrazolidinone und pyrazolidine |
| US4211876A (en) | 1979-06-13 | 1980-07-08 | E. I. Du Pont De Nemours And Company | 3-Pyrazolidinone carboxamides |
| US5605814A (en) | 1993-08-31 | 1997-02-25 | Merck Frosst Canada Inc. | DNA encoding human prostaglandin receptor EP2 |
| GB9514160D0 (en) | 1994-07-25 | 1995-09-13 | Zeneca Ltd | Aromatic compounds |
| GB9417532D0 (en) | 1994-08-31 | 1994-10-19 | Zeneca Ltd | Aromatic compounds |
| TW434240B (en) | 1995-06-20 | 2001-05-16 | Zeneca Ltd | Aromatic compounds, preparation thereof and pharmaceutical composition comprising same |
| TW502026B (en) | 1995-06-20 | 2002-09-11 | Zeneca Ltd | Aromatic compounds useful as antagonists of e-type prostaglandins, processes for the preparation thereof, pharmaceutical compositions comprising the compounds, and intermediates |
| US5834468A (en) | 1995-07-07 | 1998-11-10 | Zeneca Limited | Substituted aryl and heteroaryl compounds as E-type prostaglandin antagonists |
| WO2000015608A1 (fr) * | 1998-09-14 | 2000-03-23 | Ono Pharmaceutical Co., Ltd. | Derives e de phenyl-prostaglandine a substitution-φ et medicaments les contenant comme ingredient actif |
| US6211197B1 (en) | 1998-10-07 | 2001-04-03 | Merck Frosst Canada & Co. | Prostaglandin receptor ligands |
| IL141120A0 (en) | 2000-01-31 | 2002-02-10 | Pfizer Prod Inc | Use of prostaglandin (pge2) receptor 4 (epa) selective agonists for the treatment of acute and chronic renal failure |
| US20010056060A1 (en) * | 2000-02-07 | 2001-12-27 | Cameron Kimberly O. | Treatment of osteoporsis with EP2/EP4 receptor selective agonists |
-
2002
- 2002-10-23 EP EP02778630A patent/EP1439837B1/en not_active Expired - Lifetime
- 2002-10-23 DE DE60226051T patent/DE60226051T2/de not_active Expired - Lifetime
- 2002-10-23 ES ES02778630T patent/ES2305310T3/es not_active Expired - Lifetime
- 2002-10-23 IL IL16158102A patent/IL161581A0/xx unknown
- 2002-10-23 CA CA2463102A patent/CA2463102C/en not_active Expired - Fee Related
- 2002-10-23 WO PCT/US2002/033964 patent/WO2003035064A1/en not_active Ceased
- 2002-10-23 AU AU2002340282A patent/AU2002340282B2/en not_active Ceased
- 2002-10-23 JP JP2003537631A patent/JP4550417B2/ja not_active Expired - Fee Related
- 2002-10-23 US US10/492,910 patent/US7410991B2/en not_active Expired - Fee Related
- 2002-10-23 AT AT02778630T patent/ATE391503T1/de not_active IP Right Cessation
-
2004
- 2004-04-22 IL IL161581A patent/IL161581A/en not_active IP Right Cessation
-
2008
- 2008-05-14 US US12/120,408 patent/US7863312B2/en not_active Expired - Fee Related
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