JP2010504913A - 炎症及び免疫関連使用のための縮合環化合物 - Google Patents
炎症及び免疫関連使用のための縮合環化合物 Download PDFInfo
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- JP2010504913A JP2010504913A JP2009529277A JP2009529277A JP2010504913A JP 2010504913 A JP2010504913 A JP 2010504913A JP 2009529277 A JP2009529277 A JP 2009529277A JP 2009529277 A JP2009529277 A JP 2009529277A JP 2010504913 A JP2010504913 A JP 2010504913A
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Applications Claiming Priority (3)
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| PCT/US2007/020864 WO2008039520A2 (en) | 2006-09-26 | 2007-09-26 | Fused ring compounds for inflammation and immune-related uses |
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| CA (1) | CA2664301A1 (enExample) |
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Cited By (3)
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| JP2011509261A (ja) * | 2008-01-07 | 2011-03-24 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連用途向けの化合物 |
| JP2011517457A (ja) * | 2008-03-31 | 2011-06-09 | ジェネンテック， インコーポレイテッド | ベンゾピランおよびベンゾキセピンｐｉ３ｋ阻害剤化合物および使用方法 |
| JP2016510752A (ja) * | 2013-03-06 | 2016-04-11 | ヤンセン ファーマシューティカ エヌ．ベー． | ヒスタミンｈ４受容体のベンゾイミダゾール−２−イルピリミジンモジュレータ |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5781441A (en) * | 1980-09-16 | 1982-05-21 | Werk Fernsehelektronik Veb | Liquid crystal substance of dihydrophenanthrenes |
| JPH11240832A (ja) * | 1997-10-13 | 1999-09-07 | Yamanouchi Pharmaceut Co Ltd | アミド若しくはアミン誘導体 |
| WO2003099827A1 (en) * | 2002-05-23 | 2003-12-04 | Pliva - Istrazivacki Institut D.O.O. | 1-thia-3-aza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| WO2005005438A1 (en) * | 2003-07-08 | 2005-01-20 | Cyclacel Limited | Thiazolo-, oxazalo and imidazolo-quinazoline compounds capable of inhibiting prot ein kinases |
| WO2006040279A1 (de) * | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | Pi3-kinasen |
| WO2006040281A1 (de) * | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-indazole |
| WO2006081389A1 (en) * | 2005-01-25 | 2006-08-03 | Synta Pharmaceuticals Corp. | Thiophene compounds for inflammation and immune-related uses |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536809A (en) | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| DE3131625A1 (de) | 1980-09-16 | 1982-06-09 | VEB Werk für Fernsehelektronik im VEB Kombinat Mikroelektronik, DDR 1160 Berlin | Kristallin-fluessige substanzen des dihydrophenanthrens |
| IE58110B1 (en) | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US5073543A (en) | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
| IT1229203B (it) | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
| US5120548A (en) | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
| US5733566A (en) | 1990-05-15 | 1998-03-31 | Alkermes Controlled Therapeutics Inc. Ii | Controlled release of antiparasitic agents in animals |
| US5580578A (en) | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| RU2098418C1 (ru) * | 1992-09-14 | 1997-12-10 | Яманоути Фармасьютикал Ко., Лтд. | Конденсированное производное тиазола или его фармацевтически приемлемая соль, фармацевтическая композиция, проявляющая активность агониста 5-нт*003-рецептора на его основе |
| US5591767A (en) | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| TW260664B (enExample) | 1993-02-15 | 1995-10-21 | Otsuka Pharma Factory Inc | |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| US6274171B1 (en) | 1996-03-25 | 2001-08-14 | American Home Products Corporation | Extended release formulation of venlafaxine hydrochloride |
| KR20020069183A (ko) | 1999-07-26 | 2002-08-29 | 시오노기세이야쿠가부시키가이샤 | 트롬보포이에틴 작동성을 나타내는 의약 조성물 |
| US20030176454A1 (en) | 2000-05-15 | 2003-09-18 | Akira Yamada | N-coating heterocyclic compounds |
| JP2004018489A (ja) | 2002-06-19 | 2004-01-22 | Otsuka Pharmaceut Factory Inc | Ａｃａｔ−１阻害剤 |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| AU2004259347B2 (en) | 2003-07-23 | 2011-02-24 | Synta Pharmaceuticals, Corp. | Method for modulating calcium ion-release-activated calcium ion channels |
| RU2371438C2 (ru) | 2004-08-05 | 2009-10-27 | Ф.Хоффманн-Ля Рош Аг | Замещенные 2-ацил-2-аминотиазолы |
| EP1809294A4 (en) | 2004-09-21 | 2008-08-06 | Synta Pharmaceuticals Corp | COMPOUNDS AGAINST INFLAMMATION AND IMMUNE-RELEVANT USES |
| MX2007008290A (es) | 2005-01-07 | 2008-02-15 | Synta Pharmaceuticals Corp | Compuestos para inflamacion y usos inmuno-relacionados. |
| NZ590359A (en) | 2005-01-25 | 2012-08-31 | Synta Pharmaceuticals Corp | Pyrazine compounds for inflammation and immune-related uses |
| WO2007087442A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted biaryl compounds for inflammation and immune-related uses |
| TWI417096B (zh) | 2006-01-25 | 2013-12-01 | Synta Pharmaceuticals Corp | 用於發炎及免疫相關用途之苯基及吡啶基化合物 |
| CA2639910A1 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| TW200806292A (en) | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| EP1983971A4 (en) | 2006-01-25 | 2010-11-24 | Synta Pharmaceuticals Corp | SUBSTITUTED AROMATIC COMPOUNDS FOR USE AGAINST INFLAMMATION AND IMMUNE DISORDERS |
| US20070254926A1 (en) | 2006-01-31 | 2007-11-01 | Jun Jiang | Pyridylphenyl compounds for inflammation and immune-related uses |
| EP2001476A4 (en) | 2006-03-20 | 2010-12-22 | Synta Pharmaceuticals Corp | BENZOIMIDAZOLYL-PARAZINE-BASED COMPOUNDS FOR INFLAMMATION USES AND IMMUNE DISORDERS |
| JP2009530409A (ja) | 2006-03-23 | 2009-08-27 | シンタ ファーマシューティカルズ コーポレーション | 炎症及び免疫関連使用用のベンゾイミダゾリル−ピリジン化合物 |
| EP2086326B1 (en) | 2006-11-13 | 2014-01-08 | Synta Pharmaceuticals Corp. | Cyclohexenyl-aryl compounds for inflammation and immune-related uses |
| AU2008219115A1 (en) | 2007-02-16 | 2008-08-28 | Synta Pharmaceuticals Corp. | Substituted fused-ring compounds for inflammation and immune-related uses |
| AU2008282737A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Vinyl-aryl derivatives for inflammation and immune-related uses |
| WO2009017819A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Pyridine compounds for inflammation and immune-related uses |
| CA2695143A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Heterocycle-aryl compounds for inflammation and immune-related uses |
| US8324219B2 (en) | 2007-09-20 | 2012-12-04 | Synta Pharmaceuticals Corp. | Substituted benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses |
| EP2240029A4 (en) | 2008-01-07 | 2012-08-22 | Synta Pharmaceuticals Corp | COMPOUNDS FOR USE AGAINST INFLAMMATORY AND IMMUNOMIC DISEASES |
-
2007
- 2007-09-25 US US11/861,278 patent/US8779154B2/en not_active Expired - Fee Related
- 2007-09-26 EP EP07861381A patent/EP2086983A4/en not_active Withdrawn
- 2007-09-26 JP JP2009529277A patent/JP2010504913A/ja not_active Ceased
- 2007-09-26 CA CA002664301A patent/CA2664301A1/en not_active Abandoned
- 2007-09-26 WO PCT/US2007/020864 patent/WO2008039520A2/en not_active Ceased
- 2007-09-26 AU AU2007300450A patent/AU2007300450B2/en not_active Ceased
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5781441A (en) * | 1980-09-16 | 1982-05-21 | Werk Fernsehelektronik Veb | Liquid crystal substance of dihydrophenanthrenes |
| JPH11240832A (ja) * | 1997-10-13 | 1999-09-07 | Yamanouchi Pharmaceut Co Ltd | アミド若しくはアミン誘導体 |
| WO2003099827A1 (en) * | 2002-05-23 | 2003-12-04 | Pliva - Istrazivacki Institut D.O.O. | 1-thia-3-aza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
| WO2005005438A1 (en) * | 2003-07-08 | 2005-01-20 | Cyclacel Limited | Thiazolo-, oxazalo and imidazolo-quinazoline compounds capable of inhibiting prot ein kinases |
| WO2006040279A1 (de) * | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | Pi3-kinasen |
| WO2006040281A1 (de) * | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-indazole |
| WO2006081389A1 (en) * | 2005-01-25 | 2006-08-03 | Synta Pharmaceuticals Corp. | Thiophene compounds for inflammation and immune-related uses |
Non-Patent Citations (1)
| Title |
|---|
| JPN6012055576; Ｄ． Ｖｉｊａｙａ Ｐｒａｓａｄ ｅｔ ａｌ．: Ｓｕｌｆｕｒ Ｌｅｔｔｅｒｓ Ｖｏｌ．４（３）, 1986, ｐ．８７-９２ * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011509261A (ja) * | 2008-01-07 | 2011-03-24 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連用途向けの化合物 |
| JP2011517457A (ja) * | 2008-03-31 | 2011-06-09 | ジェネンテック， インコーポレイテッド | ベンゾピランおよびベンゾキセピンｐｉ３ｋ阻害剤化合物および使用方法 |
| JP2016510752A (ja) * | 2013-03-06 | 2016-04-11 | ヤンセン ファーマシューティカ エヌ．ベー． | ヒスタミンｈ４受容体のベンゾイミダゾール−２−イルピリミジンモジュレータ |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007300450A1 (en) | 2008-04-03 |
| WO2008039520A3 (en) | 2008-11-13 |
| EP2086983A2 (en) | 2009-08-12 |
| US20080132513A1 (en) | 2008-06-05 |
| CA2664301A1 (en) | 2008-04-03 |
| WO2008039520A2 (en) | 2008-04-03 |
| US8779154B2 (en) | 2014-07-15 |
| AU2007300450A2 (en) | 2009-06-04 |
| EP2086983A4 (en) | 2011-12-21 |
| AU2007300450B2 (en) | 2014-01-23 |
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