RU2702343C2 - Полиморфная форма [5-фтор-3-({ 2-[(4-фторбензол) сульфонил]пиридин-3-ил} метил)-2-метилиндол-1-ил]-уксусной кислоты - Google Patents
Полиморфная форма [5-фтор-3-({ 2-[(4-фторбензол) сульфонил]пиридин-3-ил} метил)-2-метилиндол-1-ил]-уксусной кислоты Download PDFInfo
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- RU2702343C2 RU2702343C2 RU2016142519A RU2016142519A RU2702343C2 RU 2702343 C2 RU2702343 C2 RU 2702343C2 RU 2016142519 A RU2016142519 A RU 2016142519A RU 2016142519 A RU2016142519 A RU 2016142519A RU 2702343 C2 RU2702343 C2 RU 2702343C2
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- asthma
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- eosinophilic
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| EP0054417A1 (en) * | 1980-12-15 | 1982-06-23 | Pfizer Limited | Indole thromboxane synthetase inhibitors, processes for their preparation, and pharmaceutical compositions containing them |
| WO2005102338A1 (en) * | 2004-04-20 | 2005-11-03 | Pfizer Limited | Method of treating neuropathic pain using a crth2 receptor antagonist |
| RU2503672C2 (ru) * | 2008-01-18 | 2014-01-10 | Оксаген Лимитед | Соединения, обладающие активностью антагонистов crth2 |
Family Cites Families (70)
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| BE790679A (fr) | 1971-11-03 | 1973-04-27 | Ici Ltd | Derives de l'indole |
| DK151884C (da) | 1979-03-07 | 1988-06-13 | Pfizer | Analogifremgangsmaade til fremstilling af 3-(1-imidazolylalkyl)indolderivater eller farmaceutisk acceptable syreadditionssalte deraf |
| US4478842A (en) | 1981-11-19 | 1984-10-23 | Ciba-Geigy Corporation | N-Substituted-2-pyridylindoles |
| GB8607294D0 (en) | 1985-04-17 | 1986-04-30 | Ici America Inc | Heterocyclic amide derivatives |
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| GB9122590D0 (en) | 1991-10-24 | 1991-12-04 | Lilly Industries Ltd | Pharmaceutical compounds |
| KR950701317A (ko) | 1992-05-08 | 1995-03-23 | 오오쓰까 아끼히꼬 | 인돌 유도체(Indole Derivative) |
| IL109309A (en) | 1993-04-16 | 2000-06-29 | Lilly Co Eli | 1-H-indole-3-acetic acid hydrazide SPLA2 inhibitors and pharmaceutical compositions containing them |
| GB9317764D0 (en) | 1993-08-26 | 1993-10-13 | Pfizer Ltd | Therapeutic compound |
| US5641800A (en) | 1994-07-21 | 1997-06-24 | Eli Lilly And Company | 1H-indole-1-functional sPLA2 inhibitors |
| US5532237A (en) | 1995-02-15 | 1996-07-02 | Merck Frosst Canada, Inc. | Indole derivatives with affinity for the cannabinoid receptor |
| EP0851030B9 (en) | 1996-06-05 | 2007-10-31 | BML Inc. | PROTEIN SPECIFIC TO HUMAN Th2, GENE (B19) ENCODING THE SAME, AND TRANSFORMANT, RECOMBINANT VECTOR AND MONOCLONAL ANTIBODY RELATING THERETO |
| US6828344B1 (en) | 1998-02-25 | 2004-12-07 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| US6916841B2 (en) | 1998-02-25 | 2005-07-12 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| US6500853B1 (en) | 1998-02-28 | 2002-12-31 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| CA2383983C (en) | 1998-03-31 | 2009-09-29 | The Institutes For Pharmaceutical Discovery, Llc | Substituted indolealkanoic acids |
| TR200003130T2 (tr) | 1998-04-28 | 2001-01-22 | Arzneimittelwerk Dresden Gmbh | Yeni hidroksiindoller, bunların fosfodiesteraz 4 inhibitörleri olarak kullanımları ve hazırlanmaları için işlemler |
| EP0984012A3 (en) | 1998-08-31 | 2001-01-10 | Pfizer Products Inc. | Nitric oxide releasing oxindole prodrugs with analgesic and anti-inflammatory properties |
| TNSN99224A1 (fr) | 1998-12-01 | 2005-11-10 | Inst For Pharm Discovery Inc | Methodes de reduction des niveaux de glucose et triglyceride en serum et pour suppression de l'antigenese utilisant les acides la indolealkanoique |
| US6884593B1 (en) | 1999-08-23 | 2005-04-26 | Bml, Inc. | Method of identifying properties of substance with respect to human prostaglandin D2 receptors |
| US20010044437A1 (en) | 2000-01-14 | 2001-11-22 | Dale Robinson | Methods for reducing uric acid levels |
| WO2001064205A2 (en) | 2000-03-02 | 2001-09-07 | The Institutes For Pharmaceutical Discovery, Llc | Compositions containing a substituted indolealkanoic acid and an angiotensin converting enzyme inhibitor |
| JP2001247570A (ja) | 2000-03-08 | 2001-09-11 | Japan Tobacco Inc | インドール酢酸化合物及びその製造方法 |
| US6878522B2 (en) | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| US6797708B2 (en) | 2001-12-03 | 2004-09-28 | Wyeth | Inhibitors of cytosolic phospholipase A2 |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| WO2003097598A1 (en) | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Compound exhibiting pgd 2 receptor antagonism |
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| MXPA05006701A (es) | 2002-12-20 | 2006-03-30 | Amgen Inc | Moduladores de asma y de inflacion alergica. |
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| MXPA06004642A (es) | 2003-11-05 | 2006-06-27 | Hoffmann La Roche | Derivados de heteroaril como activadores de los receptores activados de proliferadores de peroxisoma (ppar). |
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| JP4793692B2 (ja) | 2004-04-26 | 2011-10-12 | 小野薬品工業株式会社 | 新規なｂｌｔ２介在性疾患、ｂｌｔ２結合剤および化合物 |
| GB0412914D0 (en) | 2004-06-10 | 2004-07-14 | Oxagen Ltd | Compounds |
| US7405215B2 (en) | 2004-09-21 | 2008-07-29 | Wyeth | Indole acetic acids exhibiting CRTH2 receptor antagonism and uses thereof |
| GB2422829A (en) | 2005-02-04 | 2006-08-09 | Oxagen Ltd | Pyrrolopyridines and their use in the treatment of diseases mediated by PGD2 at the CRTH2 receptor |
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| GB0504150D0 (en) | 2005-03-01 | 2005-04-06 | Oxagen Ltd | Microcrystalline material |
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| US7956082B2 (en) | 2005-07-22 | 2011-06-07 | Shionogi & Co., Ltd | Indole derivative having PGD2 receptor antagonist activity |
| AU2006281937B2 (en) | 2005-08-12 | 2011-11-17 | Merck Canada Inc. | Indole derivatives as CRTH2 receptor antagonists |
| GB0518783D0 (en) | 2005-09-14 | 2005-10-26 | Argenta Discovery Ltd | Indolizine compounds |
| GB0605743D0 (en) | 2006-03-22 | 2006-05-03 | Oxagen Ltd | Salts with CRTH2 antagonist activity |
| GB0614066D0 (en) | 2006-07-14 | 2006-08-23 | Glaxo Group Ltd | Compounds |
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| AU2007279079A1 (en) | 2006-07-22 | 2008-01-31 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| WO2009037503A2 (en) | 2007-09-18 | 2009-03-26 | Astrazeneca Ab | New combination - 012 for the treatment of respiratory diseases |
| GB0722216D0 (en) | 2007-11-13 | 2007-12-27 | Oxagen Ltd | Use of crth2 antagonist compounds |
| GB0722203D0 (en) | 2007-11-13 | 2007-12-19 | Oxagen Ltd | Use of CRTH2 antagonist compounds |
| DK2327693T3 (da) | 2007-12-14 | 2012-08-13 | Pulmagen Therapeutics Asthma Ltd | Indoler og terapeutisk anvendelse deraf |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| WO2009090399A1 (en) | 2008-01-18 | 2009-07-23 | Argenta Discovery Limited | Indoles active on crth2 receptor |
| WO2009093029A1 (en) | 2008-01-22 | 2009-07-30 | Oxagen Limited | Compounds having crth2 antagonist activity |
| JP2011509990A (ja) | 2008-01-22 | 2011-03-31 | オキサジェン リミテッド | Ｃｒｔｈ２アンタゴニスト活性を有する化合物 |
| JP2011526281A (ja) | 2008-06-24 | 2011-10-06 | アミラ ファーマシューティカルズ，インク． | プロスタグランジンｄ２受容体のシクロアルカン［ｂ］インドールアンタゴニスト |
| GB201103837D0 (en) | 2011-03-07 | 2011-04-20 | Oxagen Ltd | Amorphous (5-Fluoro-2-Methyl-3-Quinolin-2-Ylmethyl-Indol-1-Yl)-acetic acid |
| GB201121557D0 (en) * | 2011-12-15 | 2012-01-25 | Oxagen Ltd | Process |
| CN104114169A (zh) | 2011-12-16 | 2014-10-22 | 阿托佩斯治疗有限公司 | 用于治疗嗜酸细胞性食管炎的crth2拮抗剂和质子泵抑制剂的组合物 |
| GB201322273D0 (en) | 2013-12-17 | 2014-01-29 | Atopix Therapeutics Ltd | Process |
| GB201407813D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407807D0 (en) * | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
-
2014
- 2014-05-02 GB GBGB1407820.8A patent/GB201407820D0/en not_active Ceased
-
2015
- 2015-05-01 US US15/308,290 patent/US9951042B2/en active Active
- 2015-05-01 UA UAA201612235A patent/UA121476C2/uk unknown
- 2015-05-01 WO PCT/GB2015/051296 patent/WO2015166280A1/en not_active Ceased
- 2015-05-01 JP JP2016565442A patent/JP2017514841A/ja active Pending
- 2015-05-01 EP EP15721032.9A patent/EP3137453B8/en not_active Not-in-force
- 2015-05-01 RU RU2016142519A patent/RU2702343C2/ru active
- 2015-05-01 TR TR2019/07568T patent/TR201907568T4/tr unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054417A1 (en) * | 1980-12-15 | 1982-06-23 | Pfizer Limited | Indole thromboxane synthetase inhibitors, processes for their preparation, and pharmaceutical compositions containing them |
| WO2005102338A1 (en) * | 2004-04-20 | 2005-11-03 | Pfizer Limited | Method of treating neuropathic pain using a crth2 receptor antagonist |
| RU2503672C2 (ru) * | 2008-01-18 | 2014-01-10 | Оксаген Лимитед | Соединения, обладающие активностью антагонистов crth2 |
Non-Patent Citations (2)
| Title |
|---|
| Mino R. Caira, "Crystalline Polymorphism of Organic Compounds", Topics in Current Chemistry, Vol. 198, 1998, рр.163-208. * |
| МОСКВА В.В., "РАСТВОРИТЕЛИ в ОРГАНИЧЕСКОЙ ХИМИИ", Соросовский образовательный журнал, номер 4, 1999, стр.44-50. * |
Also Published As
| Publication number | Publication date |
|---|---|
| UA121476C2 (uk) | 2020-06-10 |
| JP2017514841A (ja) | 2017-06-08 |
| RU2016142519A (ru) | 2018-06-05 |
| EP3137453B8 (en) | 2019-05-15 |
| RU2016142519A3 (enExample) | 2018-11-02 |
| WO2015166280A1 (en) | 2015-11-05 |
| US9951042B2 (en) | 2018-04-24 |
| EP3137453B1 (en) | 2019-02-27 |
| EP3137453A1 (en) | 2017-03-08 |
| GB201407820D0 (en) | 2014-06-18 |
| TR201907568T4 (tr) | 2019-06-21 |
| US20170121306A1 (en) | 2017-05-04 |
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