ES2577514T3 - Antagonistas de TLR - Google Patents
Antagonistas de TLR Download PDFInfo
- Publication number
- ES2577514T3 ES2577514T3 ES06813535.9T ES06813535T ES2577514T3 ES 2577514 T3 ES2577514 T3 ES 2577514T3 ES 06813535 T ES06813535 T ES 06813535T ES 2577514 T3 ES2577514 T3 ES 2577514T3
- Authority
- ES
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- Prior art keywords
- alkyl
- compound according
- substituted
- aryl
- alkoxy
- Prior art date
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- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
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Applications Claiming Priority (3)
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| US71033705P | 2005-08-22 | 2005-08-22 | |
| US710337P | 2005-08-22 | ||
| PCT/US2006/032371 WO2007024707A2 (en) | 2005-08-22 | 2006-08-21 | Tlr agonists |
Publications (1)
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| ES2577514T3 true ES2577514T3 (es) | 2016-07-15 |
Family
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| ES06813535.9T Active ES2577514T3 (es) | 2005-08-22 | 2006-08-21 | Antagonistas de TLR |
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| JP (2) | JP2009504803A (https=) |
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| CA (1) | CA2620182A1 (https=) |
| ES (1) | ES2577514T3 (https=) |
| WO (1) | WO2007024707A2 (https=) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003271064B2 (en) * | 2002-09-27 | 2010-06-17 | Dainippon Sumitomo Pharma Co., Ltd. | Novel adenine compound and use thereof |
| WO2005092893A1 (ja) | 2004-03-26 | 2005-10-06 | Dainippon Sumitomo Pharma Co., Ltd. | ９置換−８−オキソアデニン化合物 |
| ES2577514T3 (es) | 2005-08-22 | 2016-07-15 | The Regents Of The University Of California | Antagonistas de TLR |
| EP1939202A4 (en) * | 2005-09-22 | 2010-06-16 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| EP2029597A4 (en) | 2006-05-31 | 2011-11-23 | Univ California | purine analogs |
| EP2041135A4 (en) * | 2006-07-05 | 2010-12-01 | Astrazeneca Ab | As TLR7 MODULATORS, 8-OXOADENINE DERIVATIVES WORK |
| TW200831105A (en) * | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| ES2552471T3 (es) | 2007-02-07 | 2015-11-30 | The Regents Of The University Of California | Conjugados de agonistas de TLR sintéticos y usos de los mismos |
| US20100120799A1 (en) * | 2007-02-19 | 2010-05-13 | Smithkline Beecham Corporation | Purine derivatives as immunomodulators |
| EP2132209B8 (en) * | 2007-03-19 | 2014-04-16 | AstraZeneca AB | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7 ) modulators |
| EP2139894B1 (en) * | 2007-03-19 | 2011-10-26 | AstraZeneca AB | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7) modulators |
| AR065784A1 (es) * | 2007-03-20 | 2009-07-01 | Dainippon Sumitomo Pharma Co | Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas. |
| WO2008114819A1 (ja) * | 2007-03-20 | 2008-09-25 | Dainippon Sumitomo Pharma Co., Ltd. | 新規アデニン化合物 |
| KR20100016289A (ko) * | 2007-05-08 | 2010-02-12 | 아스트라제네카 아베 | 면역-조정 특성의 이미다조퀴놀린 |
| CA2691444C (en) * | 2007-06-29 | 2016-06-14 | Gilead Sciences, Inc. | Purine derivatives and their use as modulators of toll-like receptor 7 |
| WO2009034386A1 (en) * | 2007-09-13 | 2009-03-19 | Astrazeneca Ab | Derivatives of adenine and 8-aza-adenine and uses thereof-796 |
| UY31531A1 (es) | 2007-12-17 | 2009-08-03 | Sales derivadas de 8-oxoadenina composiciones farmacéuticas que las contienen y su uso en terapia como moduladores de receptor tipo toll (tlr) | |
| WO2009091032A1 (ja) | 2008-01-17 | 2009-07-23 | Dainippon Sumitomo Pharma Co., Ltd. | アデニン化合物の製造方法 |
| US20110054168A1 (en) * | 2008-01-17 | 2011-03-03 | Ayumu Kurimoto | Method for preparing adenine compound |
| EA201001264A1 (ru) * | 2008-02-07 | 2011-04-29 | Дзе Регентс Оф Дзе Юниверсити Оф Калифорния | Способ лечения заболеваний мочевого пузыря с помощью активатора tlr7 |
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| ES2467108T3 (es) | 2008-12-09 | 2014-06-11 | Gilead Sciences, Inc. | Moduladores de receptores tipo toll |
| US20110293565A1 (en) * | 2009-01-30 | 2011-12-01 | Idera Pharmaceuticals, Inc. | Novel synthetic agonists of tlr9 |
| WO2010088924A1 (en) | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| KR20110117705A (ko) | 2009-02-11 | 2011-10-27 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 톨-유사 수용체 조정제 및 질병의 치료 |
| US8962652B2 (en) | 2009-10-22 | 2015-02-24 | Gilead Sciences, Inc. | Derivatives of purine or deazapurine useful for the treatment of (inter alia) viral infections |
| JP2013512859A (ja) * | 2009-12-03 | 2013-04-18 | 大日本住友製薬株式会社 | トール様受容体（ｔｌｒ）を介して作用するイミダゾキノリン |
| WO2011079016A1 (en) * | 2009-12-22 | 2011-06-30 | Gilead Sciences, Inc. | Methods of treating hbv and hcv infection |
| US9050319B2 (en) | 2010-04-30 | 2015-06-09 | Telormedix, Sa | Phospholipid drug analogs |
| WO2011134669A1 (en) * | 2010-04-30 | 2011-11-03 | Telormedix Sa | Methods for inducing an immune response |
| NZ603155A (en) * | 2010-04-30 | 2014-06-27 | Telormedix Sa | Phospholipid drug analogs |
| AU2011258165B2 (en) | 2010-05-26 | 2016-11-17 | Selecta Biosciences, Inc. | Dose selection of adjuvanted synthetic nanocarriers |
| US20120083473A1 (en) | 2010-09-21 | 2012-04-05 | Johanna Holldack | Treatment of conditions by toll-like receptor modulators |
| WO2012061717A1 (en) | 2010-11-05 | 2012-05-10 | Selecta Biosciences, Inc. | Modified nicotinic compounds and related methods |
| JP5978225B2 (ja) | 2010-12-16 | 2016-08-24 | 大日本住友製薬株式会社 | 治療に有用なイミダゾ［４，５−ｃ］キノリン−１−イル誘導体 |
| ES2627433T3 (es) | 2010-12-17 | 2017-07-28 | Sumitomo Dainippon Pharma Co., Ltd. | Derivados de purina |
| TW201247706A (en) * | 2011-03-08 | 2012-12-01 | Baylor Res Inst | Novel vaccine adjuvants based on targeting adjuvants to antibodies directly to antigen-presenting cells |
| SI2734186T1 (sl) | 2011-07-22 | 2018-11-30 | Glaxosmithkline Llc | Sestavek |
| AU2012287024A1 (en) * | 2011-07-22 | 2014-02-20 | Pawel Kalinski | Tumor selective chemokine modulation |
| ES2653254T3 (es) | 2012-08-24 | 2018-02-06 | Glaxosmithkline Llc | Compuestos de pirazolopirimidina |
| WO2014052828A1 (en) | 2012-09-27 | 2014-04-03 | The Regents Of The University Of California | Compositions and methods for modulating tlr4 |
| US9550785B2 (en) | 2012-11-20 | 2017-01-24 | Glaxosmithkline Llc | Pyrrolopyrimidines as therapeutic agents for the treatment of diseases |
| KR20150085081A (ko) | 2012-11-20 | 2015-07-22 | 글락소스미스클라인 엘엘씨 | 신규 화합물 |
| MX358025B (es) | 2012-11-20 | 2018-08-02 | Glaxosmithkline Llc Star | Compuestos novedosos. |
| EP2958889B1 (en) * | 2013-02-25 | 2017-03-22 | The Scripps Research Institute | Neoseptins: small molecule adjuvants |
| PT3166607T (pt) | 2014-07-11 | 2022-12-07 | Gilead Sciences Inc | Moduladores de receptores de tipo toll para o tratamento do vih |
| US9918959B2 (en) | 2014-08-06 | 2018-03-20 | The Board Of Regents Of The University Of Texas System | TLR-independent small molecule adjuvants |
| HUE054672T2 (hu) * | 2014-08-15 | 2021-09-28 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | TLR7 agonistaként alkalmazott pirrolopirimidin vegyületek |
| CA2960436C (en) | 2014-09-16 | 2021-01-05 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| CA3004173C (en) | 2015-11-05 | 2020-07-14 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | 7-(thiazol-5-yl)pyrrolopyrimidine compound as tlr7 agonist |
| CN107043380A (zh) | 2016-02-05 | 2017-08-15 | 正大天晴药业集团股份有限公司 | 一种tlr7激动剂的马来酸盐、其晶型c、晶型d、晶型e、制备方法和用途 |
| CN107043379A (zh) * | 2016-02-05 | 2017-08-15 | 正大天晴药业集团股份有限公司 | 一种tlr7激动剂的晶型a、其制备方法和医药用途 |
| US11697851B2 (en) | 2016-05-24 | 2023-07-11 | The Regents Of The University Of California | Early ovarian cancer detection diagnostic test based on mRNA isoforms |
| KR102726248B1 (ko) | 2016-07-07 | 2024-11-05 | 더 보드 어브 트러스티스 어브 더 리랜드 스탠포드 주니어 유니버시티 | 항체-애쥬번트 접합체 |
| US10610104B2 (en) | 2016-12-07 | 2020-04-07 | Progenity, Inc. | Gastrointestinal tract detection methods, devices and systems |
| CN110290810A (zh) | 2016-12-13 | 2019-09-27 | 博尔特生物治疗药物有限公司 | 抗体佐剂缀合物 |
| CA3046019A1 (en) | 2016-12-14 | 2018-06-21 | Progenity Inc. | Treatment of a disease of the gastrointestinal tract with a tlr modulator |
| DK3609540T5 (da) | 2017-04-14 | 2024-09-02 | Bolt Biotherapeutics Inc | Fremgangsmåde til immunkonjugatsyntese |
| JP2021035910A (ja) * | 2017-11-01 | 2021-03-04 | 大日本住友製薬株式会社 | 置換プリン化合物 |
| WO2019196918A1 (zh) * | 2018-04-13 | 2019-10-17 | 罗欣药业(上海)有限公司 | 五元杂环并嘧啶类化合物、药物组合物及用途 |
| WO2019222676A1 (en) | 2018-05-17 | 2019-11-21 | Bolt Biotherapeutics, Inc. | Immunoconjugates |
| CN109608462B (zh) * | 2018-12-15 | 2021-11-23 | 华南理工大学 | 一种7-烃基-9-烷氧/硫基嘌呤-8-酮类化合物及其合成方法与在药物中的应用 |
| AU2020241686A1 (en) | 2019-03-15 | 2021-11-04 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting HER2 |
| WO2021046347A1 (en) | 2019-09-04 | 2021-03-11 | Bolt Biotherapeutics, Inc. | Immunoconjugate synthesis method |
| US20230107927A1 (en) | 2020-02-28 | 2023-04-06 | First Wave Bio, Inc. | Methods of treating iatrogenic autoimmune colitis |
| AU2021300632A1 (en) | 2020-07-02 | 2023-02-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Method of achieving HIV viral remission using long-acting antiretroviral agents |
| CN114315861A (zh) * | 2020-09-27 | 2022-04-12 | 上海维申医药有限公司 | 大环tlr7激动剂、其制备方法、药物组合物及其用途 |
| CA3196221A1 (en) | 2020-10-21 | 2022-04-28 | Univerza V Ljubljani | Conjugated tlr7 and nod2 agonists |
| CN115819215B (zh) * | 2022-11-08 | 2024-09-13 | 广东省科学院化工研究所 | 一种路易斯酸催化合成羧酸衍生物的方法 |
| WO2025040743A1 (en) | 2023-08-22 | 2025-02-27 | Univerza V Ljubljani | Conjugated tlr7 and rig-i agonists |
| WO2025093657A1 (en) | 2023-10-31 | 2025-05-08 | Univerza V Ljubljani | Conjugated tlr7 and tlr4 agonists |
| TW202602849A (zh) * | 2024-03-28 | 2026-01-16 | 日商日產化學股份有限公司 | 石墨烯連接化合物及場效電晶體生物檢測器 |
Family Cites Families (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| CA1271477A (en) | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| US5238944A (en) * | 1988-12-15 | 1993-08-24 | Riker Laboratories, Inc. | Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine |
| US5736553A (en) * | 1988-12-15 | 1998-04-07 | Riker Laboratories, Inc. | Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo 4,5-C!quinolin-4-amine |
| US5037986A (en) * | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
| US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| NZ232740A (en) | 1989-04-20 | 1992-06-25 | Riker Laboratories Inc | Solution for parenteral administration comprising a 1h-imidazo(4,5-c) quinolin-4-amine derivative, an acid and a tonicity adjuster |
| DK0553202T3 (da) | 1990-10-05 | 1995-07-03 | Minnesota Mining & Mfg | Fremgangsmåde til fremstilling af imidazo(4,5-c)quinolin-4-aminer |
| US5175296A (en) | 1991-03-01 | 1992-12-29 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5648516A (en) * | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5525606A (en) * | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| DE19505168A1 (de) | 1995-02-16 | 1996-08-22 | Boehringer Mannheim Gmbh | Spezifische Lipidkonjugate von Nucleosid-Diphosphonaten und deren Verwendung als Arzneimittel |
| US5624677A (en) * | 1995-06-13 | 1997-04-29 | Pentech Pharmaceuticals, Inc. | Controlled release of drugs delivered by sublingual or buccal administration |
| US5693811A (en) | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| US5741908A (en) * | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| DE19637209B4 (de) * | 1996-09-12 | 2006-12-14 | Siemens Ag | Verfahren zum Steuern des Antriebsstrangs eines Kraftfahrzeugs und integrierte Antriebsstrangsteuerung |
| KR100518903B1 (ko) | 1996-10-25 | 2005-10-06 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | Ｔｈ2 매개 질병 및 관련 질병의 치료용 면역 반응 조절 화합물 |
| DE69735292T2 (de) | 1996-10-25 | 2006-10-19 | Gilead Sciences, Inc., Foster City | Gefaesszellen wachstumsfaktor (vegf) nukleinsäureligand-komplexe |
| JPH10298181A (ja) | 1997-04-25 | 1998-11-10 | Sumitomo Pharmaceut Co Ltd | タイプ２ヘルパーｔ細胞選択的免疫応答抑制剤 |
| WO1999024432A1 (fr) * | 1997-11-12 | 1999-05-20 | Mitsubishi Chemical Corporation | Derives de purine et medicament les renfermant en tant qu'ingredient actif |
| NZ504800A (en) | 1997-11-28 | 2001-10-26 | Sumitomo Pharma | 6-Amino-9-benzyl-8-hydroxy-purine derivatives and interferon inducers, antiviral agents, anticancer agents and therapeutic agents for immunologic diseases thereof |
| JP4189048B2 (ja) * | 1997-12-26 | 2008-12-03 | 大日本住友製薬株式会社 | 複素環化合物 |
| US7001609B1 (en) * | 1998-10-02 | 2006-02-21 | Regents Of The University Of Minnesota | Mucosal originated drug delivery systems and animal applications |
| TR200101943T2 (tr) * | 1999-01-08 | 2002-04-22 | 3M Innovative Properties Company | Bir immun cevap modifayeri ile mukoza ile ilgili durumların tedavisine yönelik formülasyonlar ve metodlar. |
| US20020058674A1 (en) * | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6486168B1 (en) * | 1999-01-08 | 2002-11-26 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| CZ27399A3 (cs) * | 1999-01-26 | 2000-08-16 | Ústav Experimentální Botaniky Av Čr | Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv |
| ATE345349T1 (de) | 1999-12-17 | 2006-12-15 | Ariad Pharma Inc | Purinderivate |
| DE60028253T2 (de) | 1999-12-17 | 2007-03-08 | Ariad Pharmaceuticals, Inc., Cambridge | Neue purine |
| ATE322494T1 (de) | 2000-01-07 | 2006-04-15 | Universitaire Instelling Antwe | Purin derivate, ihre herstellung und verwendung |
| US6733764B2 (en) * | 2000-06-14 | 2004-05-11 | Alain Martin | Immunostimulator anti-cancer compounds and methods for their use in the treatment of cancer |
| AU2002212273B2 (en) * | 2000-09-15 | 2007-06-14 | Aaron Diamond Aids Research Centre | System and method for optimizing drug therapy for the treatment of diseases |
| GB0023008D0 (en) | 2000-09-20 | 2000-11-01 | Glaxo Group Ltd | Improvements in vaccination |
| US20020127224A1 (en) | 2001-03-02 | 2002-09-12 | James Chen | Use of photoluminescent nanoparticles for photodynamic therapy |
| ATE348097T1 (de) * | 2001-04-09 | 2007-01-15 | Chiron Corp | Guanidinoverbindungen als melanocortin-4-rezeptor (mc4-r) agonisten |
| US7157465B2 (en) * | 2001-04-17 | 2007-01-02 | Dainippon Simitomo Pharma Co., Ltd. | Adenine derivatives |
| EP1572067A4 (en) | 2001-05-18 | 2009-05-13 | Sirna Therapeutics Inc | CONJUGATES AND COMPOSITIONS FOR CELLULAR RELEASE |
| DE60206756T2 (de) | 2001-06-29 | 2006-07-13 | CV Therapeutics, Inc., Palo Alto | Purin derivate als a2b adenosin rezeptor antagonisten |
| US7241890B2 (en) * | 2001-10-30 | 2007-07-10 | Conforma Therapeutics Corporation | Purine analogs having HSP90-inhibiting activity |
| GB0206461D0 (en) | 2002-03-19 | 2002-05-01 | Glaxo Group Ltd | Improvements in vaccination |
| NZ538812A (en) * | 2002-08-15 | 2009-02-28 | 3M Innovative Properties Co | Immunostimulatory compositions and methods of stimulating an immune response |
| AU2003271064B2 (en) * | 2002-09-27 | 2010-06-17 | Dainippon Sumitomo Pharma Co., Ltd. | Novel adenine compound and use thereof |
| JP2004137157A (ja) | 2002-10-16 | 2004-05-13 | Sumitomo Pharmaceut Co Ltd | 新規アデニン誘導体を有効成分として含有する医薬 |
| US20040265351A1 (en) * | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| WO2005016235A2 (en) * | 2003-04-14 | 2005-02-24 | The Regents Of The University Of California | Combined use of impdh inhibitors with toll-like receptor agonists |
| US20050059613A1 (en) * | 2003-07-08 | 2005-03-17 | Bahram Memarzadeh | Compositions and methods for the enhanced uptake of therapeutic agents through the bladder epithelium |
| WO2005020892A2 (en) * | 2003-08-08 | 2005-03-10 | Mitochroma Research, Inc. | Pharmaceutical compositions and methods for metabolic modulation |
| EP1667694B1 (en) * | 2003-09-05 | 2010-04-28 | Anadys Pharmaceuticals, Inc. | Tlr7 ligands for the treatment of hepatitis c |
| JP2005089334A (ja) * | 2003-09-12 | 2005-04-07 | Sumitomo Pharmaceut Co Ltd | ８−ヒドロキシアデニン化合物 |
| KR20060070572A (ko) * | 2003-09-18 | 2006-06-23 | 콘포마 세러퓨틱스 코포레이션 | Ｈｓｐ90-저해제로서의 신규 헤테로시클릭 화합물 |
| FR2863890B1 (fr) | 2003-12-19 | 2006-03-24 | Aventis Pasteur | Composition immunostimulante |
| JP2007526322A (ja) * | 2004-03-02 | 2007-09-13 | マサチューセッツ インスティテュート オブ テクノロジー | ナノセル薬物送達系 |
| US20070225303A1 (en) | 2004-03-26 | 2007-09-27 | Haruhisa Ogita | 8-Oxoadenine Compound |
| WO2005092893A1 (ja) | 2004-03-26 | 2005-10-06 | Dainippon Sumitomo Pharma Co., Ltd. | ９置換−８−オキソアデニン化合物 |
| CA2587676A1 (en) * | 2004-11-19 | 2006-05-26 | Institut Gustave Roussy | Improved treatment of cancer by double-stranded rna |
| PT1819230E (pt) | 2004-12-07 | 2012-08-07 | Univ Miami | Micropartículas derivadas de células vermelhas como agentes hemostáticos para o controlo da hemorragia e para o tratamento de patologias hemorrágicas |
| DK1879893T3 (da) | 2005-03-21 | 2010-09-13 | Ferrer Int | Fremgangsmåde til fremstilling af 1-substituerede 1H-imidazo[4,5-c]quinolin-4-aminforbindelser og mellemprodukter dertil |
| US20070292418A1 (en) * | 2005-04-26 | 2007-12-20 | Eisai Co., Ltd. | Compositions and methods for immunotherapy |
| ES2577514T3 (es) | 2005-08-22 | 2016-07-15 | The Regents Of The University Of California | Antagonistas de TLR |
| EP1939202A4 (en) | 2005-09-22 | 2010-06-16 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| WO2007034917A1 (ja) | 2005-09-22 | 2007-03-29 | Dainippon Sumitomo Pharma Co., Ltd. | 新規なアデニン化合物 |
| KR20080059595A (ko) | 2005-09-27 | 2008-06-30 | 콜리 파마슈티칼 게엠베하 | 어댑터 올리고뉴클레오티드를 사용하는 ｔｌｒ-매개 면역반응의 조절 |
| US20070100146A1 (en) * | 2005-11-03 | 2007-05-03 | Trevor Dzwiniel | Process for the preparation of imidazo[4,5-c]-quinolin-4-amines |
| EP2029597A4 (en) | 2006-05-31 | 2011-11-23 | Univ California | purine analogs |
| EP2038290B1 (en) | 2006-07-07 | 2013-09-04 | Gilead Sciences, Inc. | Modulators of toll-like receptor 7 |
| TW200831104A (en) * | 2006-10-04 | 2008-08-01 | Pharmacopeia Inc | 6-substituted 2-(benzimidazolyl)purine and purinone derivatives for immunosuppression |
| US7902187B2 (en) * | 2006-10-04 | 2011-03-08 | Wyeth Llc | 6-substituted 2-(benzimidazolyl)purine and purinone derivatives for immunosuppression |
| ES2552471T3 (es) | 2007-02-07 | 2015-11-30 | The Regents Of The University Of California | Conjugados de agonistas de TLR sintéticos y usos de los mismos |
| CA2691444C (en) * | 2007-06-29 | 2016-06-14 | Gilead Sciences, Inc. | Purine derivatives and their use as modulators of toll-like receptor 7 |
| JP2011500716A (ja) | 2007-10-16 | 2011-01-06 | ギリアード・パロ・アルト・インコーポレイテッド | Ａ３アデノシン受容体アンタゴニスト |
| EA201001264A1 (ru) | 2008-02-07 | 2011-04-29 | Дзе Регентс Оф Дзе Юниверсити Оф Калифорния | Способ лечения заболеваний мочевого пузыря с помощью активатора tlr7 |
| WO2010088924A1 (en) * | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| KR20110117705A (ko) | 2009-02-11 | 2011-10-27 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | 톨-유사 수용체 조정제 및 질병의 치료 |
| US8962652B2 (en) | 2009-10-22 | 2015-02-24 | Gilead Sciences, Inc. | Derivatives of purine or deazapurine useful for the treatment of (inter alia) viral infections |
| WO2011134669A1 (en) | 2010-04-30 | 2011-11-03 | Telormedix Sa | Methods for inducing an immune response |
| US20130202629A1 (en) | 2010-04-30 | 2013-08-08 | The Regents Of The University Of California | Uses of phospholipid conjugates of synthetic tlr7 agonists |
| NZ603155A (en) | 2010-04-30 | 2014-06-27 | Telormedix Sa | Phospholipid drug analogs |
| ES2458355T3 (es) | 2010-09-01 | 2014-05-05 | Novartis Ag | Adsorción de inmunopotenciadores sobre sales metálicas insolubles |
| US20120083473A1 (en) | 2010-09-21 | 2012-04-05 | Johanna Holldack | Treatment of conditions by toll-like receptor modulators |
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2006
- 2006-08-21 ES ES06813535.9T patent/ES2577514T3/es active Active
- 2006-08-21 EP EP06813535.9A patent/EP1931352B1/en not_active Not-in-force
- 2006-08-21 JP JP2008528017A patent/JP2009504803A/ja active Pending
- 2006-08-21 WO PCT/US2006/032371 patent/WO2007024707A2/en not_active Ceased
- 2006-08-21 CA CA002620182A patent/CA2620182A1/en not_active Abandoned
- 2006-08-21 CN CNA200680038761XA patent/CN101304748A/zh active Pending
- 2006-08-21 US US12/064,529 patent/US20090324551A1/en not_active Abandoned
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2012
- 2012-11-20 US US13/682,208 patent/US9359360B2/en active Active
- 2012-11-20 JP JP2012254043A patent/JP2013040209A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009504803A (ja) | 2009-02-05 |
| WO2007024707A3 (en) | 2007-09-20 |
| EP1931352B1 (en) | 2016-04-13 |
| CA2620182A1 (en) | 2007-03-01 |
| US9359360B2 (en) | 2016-06-07 |
| AU2006283524A1 (en) | 2007-03-01 |
| EP1931352A2 (en) | 2008-06-18 |
| JP2013040209A (ja) | 2013-02-28 |
| EP1931352A4 (en) | 2011-11-23 |
| AU2006283524A2 (en) | 2008-06-05 |
| US20130165455A1 (en) | 2013-06-27 |
| CN101304748A (zh) | 2008-11-12 |
| WO2007024707A2 (en) | 2007-03-01 |
| US20090324551A1 (en) | 2009-12-31 |
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