PL210514B1 - Preparat farmaceutyczny zawierający modyfikator odpowiedzi immunologicznej - Google Patents
Preparat farmaceutyczny zawierający modyfikator odpowiedzi immunologicznejInfo
- Publication number
- PL210514B1 PL210514B1 PL373303A PL37330302A PL210514B1 PL 210514 B1 PL210514 B1 PL 210514B1 PL 373303 A PL373303 A PL 373303A PL 37330302 A PL37330302 A PL 37330302A PL 210514 B1 PL210514 B1 PL 210514B1
- Authority
- PL
- Poland
- Prior art keywords
- weight
- hydrophobic
- formulation according
- fatty acid
- imidazo
- Prior art date
Links
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Families Citing this family (130)
| Publication number | Priority date | Publication date | Assignee | Title |
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| UA67760C2 (uk) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
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| WO2005082334A1 (ja) * | 2004-02-27 | 2005-09-09 | Hisamitsu Pharmaceutical Co., Inc. | 徐放性クリーム剤 |
| ES2665342T3 (es) | 2004-03-15 | 2018-04-25 | Meda Ab | Formulaciones y métodos para modificadores de la respuesta inmune |
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| US20050267145A1 (en) * | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
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| AU2005283085B2 (en) * | 2004-06-18 | 2012-06-21 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| EP1786450A4 (en) * | 2004-08-27 | 2009-11-11 | 3M Innovative Properties Co | HIV IMMUNOSTIMATORY COMPOSITIONS |
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| CA2592904C (en) | 2004-12-30 | 2015-04-07 | 3M Innovative Properties Company | Chiral fused [1,2]imidazo[4,5-c] ring compounds |
| US8436176B2 (en) * | 2004-12-30 | 2013-05-07 | Medicis Pharmaceutical Corporation | Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine |
| KR20070102728A (ko) * | 2005-02-04 | 2007-10-19 | 다케다 야쿠힌 고교 가부시키가이샤 | 1-(2-메틸프로필)-1H-이미다조[4,5-c][1,5]나프티리딘-4-아민을 함유하는 수성 겔 제제 |
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| AU2006216799A1 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazonaphthyridines |
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| WO2006098852A2 (en) | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| EP1865957A4 (en) * | 2005-03-14 | 2009-05-06 | Meda Ab | METHOD FOR TREATING RADIATION KERATOSIS |
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| CA2621831A1 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of n-{2-[4-amino-2- (ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| US8889154B2 (en) * | 2005-09-15 | 2014-11-18 | Medicis Pharmaceutical Corporation | Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation |
| CN101309687A (zh) | 2005-11-04 | 2008-11-19 | 科勒制药集团公司 | 经羟基和烷氧基取代的1h-咪唑并喹啉及其方法 |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2007106854A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods |
| WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| CA2659095C (en) | 2006-07-14 | 2015-04-28 | Stiefel Research Australia Pty Ltd | Fatty acid pharmaceutical foam |
| JP2009543866A (ja) * | 2006-07-18 | 2009-12-10 | ウイラ アイピー プロプライエタリー リミテッド | 免疫応答修飾製剤 |
| US8124096B2 (en) * | 2006-07-31 | 2012-02-28 | 3M Innovative Properties Company | Immune response modifier compositions and methods |
| WO2008030511A2 (en) | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| CA2664548C (en) * | 2006-12-29 | 2014-04-08 | Graceway Pharmaceuticals, Llc | Packaging for 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine-containing formulation |
| MX2008010860A (es) * | 2006-12-29 | 2009-02-25 | Graceway Pharmaceuticals Llc | Formulaciones del modificador de inmunorespuesta que contienen acido oleico y metodos. |
| CN103396415B (zh) * | 2008-03-24 | 2016-08-10 | 4Sc股份有限公司 | 新的取代的咪唑并喹啉化合物 |
| US20100160368A1 (en) | 2008-08-18 | 2010-06-24 | Gregory Jefferson J | Methods of Treating Dermatological Disorders and Inducing Interferon Biosynthesis With Shorter Durations of Imiquimod Therapy |
| KR20110090892A (ko) * | 2008-10-31 | 2011-08-10 | 모베르그 데르마 아베 | 두 개 이상의 침투 증강제의 조합으로 구성되는 국소 조성물 |
| RS58566B1 (sr) | 2008-12-19 | 2019-05-31 | Medicis Pharmaceutical Corp | Formulacije imikuimoda niže dozne jačine i kratkih režima doziranja za lečenje aktinične keratoze |
| BR112012000797A2 (pt) | 2009-07-13 | 2016-08-09 | Medicis Pharmaceutical Corp | formulações de imiquimode de intensidade de dosagem inferior e regimes curtos de dosagem para tratamento de verrugas genitais e perianais |
| CN104940225A (zh) * | 2009-08-24 | 2015-09-30 | 谭国梁 | 可使病变组织及病原体溶解消除的药物 |
| WO2011051971A2 (en) * | 2009-10-27 | 2011-05-05 | Lupin Limited | Solid dispersion of rifaximin |
| WO2012024284A1 (en) | 2010-08-17 | 2012-02-23 | 3M Innovative Properties Company | Lipidated immune response modifier compound compositions, formulations, and methods |
| JP6460789B2 (ja) | 2011-06-03 | 2019-01-30 | スリーエム イノベイティブ プロパティズ カンパニー | ポリエチレングリコールセグメントを有するヘテロ2官能性リンカー及び該リンカーから調製された免疫反応調節複合体 |
| JP6415979B2 (ja) | 2011-06-03 | 2018-10-31 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドラジノ1h−イミダゾキノリン−4−アミン及びこれから調製された複合体 |
| US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
| RU2687279C2 (ru) * | 2013-11-05 | 2019-05-13 | 3М Инновейтив Пропертиз Компани | Инъекционные композиции на основе кунжутного масла |
| GB201321242D0 (en) | 2013-12-02 | 2014-01-15 | Immune Targeting Systems Its Ltd | Immunogenic compound |
| CA3029902A1 (en) | 2016-07-07 | 2018-01-11 | The Board Of Trustees Of The Leland Stanford Junior University | Antibody adjuvant conjugates |
| JP2020511501A (ja) | 2016-12-13 | 2020-04-16 | ボルト バイオセラピューティクス、インコーポレーテッド | 抗体アジュバント複合体 |
| US11306083B2 (en) | 2017-12-20 | 2022-04-19 | 3M Innovative Properties Company | Amide substituted imidazo[4,5-C]quinoline compounds with a branched chain linking group for use as an immune response modifier |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) * | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| US4722941A (en) * | 1978-06-07 | 1988-02-02 | Kali-Chemie Pharma Gmbh | Readily absorbable pharmaceutical compositions of per se poorly absorbable pharmacologically active agents and preparation thereof |
| ZA848968B (en) * | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 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 |
| US4595586A (en) * | 1985-08-30 | 1986-06-17 | Eli Lilly And Company | Moisturizing lotion |
| US4800076A (en) * | 1987-03-13 | 1989-01-24 | Johnson & Johnson Consumer Products, Inc. | Skin care compositions |
| 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 |
| US5756747A (en) * | 1989-02-27 | 1998-05-26 | Riker Laboratories, Inc. | 1H-imidazo 4,5-c!quinolin-4-amines |
| US4996193A (en) * | 1989-03-03 | 1991-02-26 | The Regents Of The University Of California | Combined topical and systemic method of administration of cyclosporine |
| US4973468A (en) * | 1989-03-22 | 1990-11-27 | Cygnus Research Corporation | Skin permeation enhancer compositions |
| 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 |
| US4988815A (en) * | 1989-10-26 | 1991-01-29 | Riker Laboratories, Inc. | 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines |
| DE69108920T2 (de) * | 1990-10-05 | 1995-11-30 | Minnesota Mining And Mfg. Co., Saint Paul, Minn. | Verfahren zur herstellung von imidazo[4,5-c]chinolin-4-aminen. |
| 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 |
| US5389640A (en) * | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5268376A (en) * | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5266575A (en) * | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| 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 |
| CZ288182B6 (en) * | 1993-07-15 | 2001-05-16 | Minnesota Mining & Mfg | Imidazo[4,5-c]pyridine-4-amines and pharmaceutical preparations based thereon |
| US5482936A (en) * | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| SE9503143D0 (sv) * | 1995-09-12 | 1995-09-12 | Astra Ab | New preparation |
| JPH09208584A (ja) | 1996-01-29 | 1997-08-12 | Terumo Corp | アミド誘導体、およびそれを含有する医薬製剤、および合成中間体 |
| US5741908A (en) * | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| US5693811A (en) * | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| IL129319A0 (en) * | 1996-10-25 | 2000-02-17 | Minnesota Mining & Mfg | Immune response modifier compounds for treatment of TH2 mediated and related diseases |
| US5728732A (en) * | 1996-11-27 | 1998-03-17 | Elizabeth Arden Company, Division Of Conopco, Inc. | Skin treatment with salicylic acid esters and retinoids |
| US5939090A (en) * | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| EP0894797A4 (en) * | 1997-01-09 | 2001-08-16 | Terumo Corp | NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS |
| US5939080A (en) * | 1997-01-10 | 1999-08-17 | The Procter & Gamble Company | Hydrophobic agents and non-polymeric surfactants use in oral care products |
| TW450810B (en) | 1997-02-20 | 2001-08-21 | Fujisawa Pharmaceutical Co | Macrolides antibiotic pharmaceutical composition for preventing and treating skin diseases |
| US6248763B1 (en) * | 1998-05-19 | 2001-06-19 | Scivoletto Rosemarie | Composition for treating skin conditions |
| US6372234B1 (en) * | 1997-05-27 | 2002-04-16 | Sembiosys Genetics Inc. | Products for topical applications comprising oil bodies |
| UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| JPH11222432A (ja) | 1998-02-03 | 1999-08-17 | Terumo Corp | インターフェロンを誘起するアミド誘導体を含有する外用剤 |
| JPH11255926A (ja) | 1998-03-13 | 1999-09-21 | Toray Ind Inc | シリコーン成型品およびその製造方法 |
| US6110929A (en) * | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | 1h―イミダゾピリジン誘導体 |
| WO2000025732A1 (en) | 1998-11-03 | 2000-05-11 | Bristol-Myers Squibb Company | Skin moisturizer compositions containing a sebum control agent |
| US20020058674A1 (en) * | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| SK287112B6 (sk) * | 1999-01-08 | 2009-12-07 | 3M Innovative Properties Company | Použitie zlúčeniny modifikujúcej imunitnú odpoveď pri liečení cervikálnej dysplázie |
| 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 |
| US6558951B1 (en) | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| EP1029977A1 (en) * | 1999-02-18 | 2000-08-23 | SCA Hygiene Products GmbH | Composition for treating an absorbent paper product and an absorbent paper product treated with said composition |
| JP2000247884A (ja) | 1999-03-01 | 2000-09-12 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| JP4521899B2 (ja) | 1999-08-27 | 2010-08-11 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | クロタミトン含有皮膚外用液剤 |
| US6376669B1 (en) * | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20020055517A1 (en) * | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| JP2002145777A (ja) | 2000-11-06 | 2002-05-22 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| UA74852C2 (en) | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| EP1360486A2 (en) | 2000-12-08 | 2003-11-12 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| EP1401437A1 (en) | 2001-06-15 | 2004-03-31 | 3M Innovative Properties Company | Immune response modifiers for the treatment of periodontal disease |
-
2002
- 2002-11-27 CA CA2467828A patent/CA2467828C/en not_active Expired - Fee Related
- 2002-11-27 JP JP2003546893A patent/JP4447914B2/ja not_active Expired - Fee Related
- 2002-11-27 HR HRP20040474AA patent/HRP20040474B1/hr not_active IP Right Cessation
- 2002-11-27 PL PL373303A patent/PL210514B1/pl unknown
- 2002-11-27 AT AT02798470T patent/ATE406164T1/de active
- 2002-11-27 WO PCT/US2002/038190 patent/WO2003045391A1/en not_active Ceased
- 2002-11-27 MX MXPA04005023A patent/MXPA04005023A/es active IP Right Grant
- 2002-11-27 IL IL16178602A patent/IL161786A0/xx unknown
- 2002-11-27 CN CNB028237056A patent/CN100473384C/zh not_active Expired - Fee Related
- 2002-11-27 EP EP02798470A patent/EP1450804B9/en not_active Expired - Lifetime
- 2002-11-27 BR BR0214566-9A patent/BR0214566A/pt not_active Application Discontinuation
- 2002-11-27 NZ NZ532769A patent/NZ532769A/en not_active IP Right Cessation
- 2002-11-27 DE DE60228611T patent/DE60228611D1/de not_active Expired - Lifetime
- 2002-11-27 AU AU2002363954A patent/AU2002363954B2/en not_active Ceased
- 2002-11-27 RU RU2004116474/15A patent/RU2327460C2/ru active
- 2002-11-27 DK DK02798470T patent/DK1450804T3/da active
- 2002-11-27 US US10/306,019 patent/US20030199538A1/en not_active Abandoned
- 2002-11-27 ES ES02798470T patent/ES2312659T3/es not_active Expired - Lifetime
- 2002-11-27 KR KR1020047008119A patent/KR100962751B1/ko not_active Expired - Fee Related
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2004
- 2004-05-05 IL IL161786A patent/IL161786A/en active IP Right Grant
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- 2008-07-14 US US12/172,712 patent/US7968562B2/en not_active Expired - Fee Related
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| NZ532769A (en) | 2005-12-23 |
| US20080275077A1 (en) | 2008-11-06 |
| AU2002363954B2 (en) | 2008-04-03 |
| WO2003045391A1 (en) | 2003-06-05 |
| JP2005510540A (ja) | 2005-04-21 |
| KR100962751B1 (ko) | 2010-06-09 |
| EP1450804B1 (en) | 2008-08-27 |
| CN100473384C (zh) | 2009-04-01 |
| DE60228611D1 (de) | 2008-10-09 |
| IL161786A (en) | 2012-02-29 |
| HRP20040474B1 (hr) | 2014-08-15 |
| CA2467828A1 (en) | 2003-06-05 |
| HK1073778A1 (zh) | 2005-10-21 |
| PL373303A1 (en) | 2005-08-22 |
| CA2467828C (en) | 2011-10-04 |
| KR20040062974A (ko) | 2004-07-09 |
| RU2004116474A (ru) | 2005-06-10 |
| BR0214566A (pt) | 2005-11-01 |
| US20030199538A1 (en) | 2003-10-23 |
| JP4447914B2 (ja) | 2010-04-07 |
| CN1610550A (zh) | 2005-04-27 |
| IL161786A0 (en) | 2005-11-20 |
| AU2002363954A1 (en) | 2003-06-10 |
| EP1450804B9 (en) | 2009-04-01 |
| MXPA04005023A (es) | 2004-08-11 |
| RU2327460C2 (ru) | 2008-06-27 |
| US7968562B2 (en) | 2011-06-28 |
| EP1450804A1 (en) | 2004-09-01 |
| ES2312659T3 (es) | 2009-03-01 |
| ATE406164T1 (de) | 2008-09-15 |
| DK1450804T3 (da) | 2009-01-05 |
| HRP20040474A2 (en) | 2004-12-31 |
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