CN113402518B - 含有取代的胍基团的咪唑并[4,5-c]环化合物 - Google Patents
含有取代的胍基团的咪唑并[4,5-c]环化合物 Download PDFInfo
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Life Sciences & Earth Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- General Chemical & Material Sciences (AREA)
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- Virology (AREA)
- Communicable Diseases (AREA)
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|---|---|---|---|
| CN202110672923.1A CN113402518B (zh) | 2015-08-31 | 2016-08-26 | 含有取代的胍基团的咪唑并[4,5-c]环化合物 |
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| US201562211896P | 2015-08-31 | 2015-08-31 | |
| US62/211,896 | 2015-08-31 | ||
| PCT/US2016/048831 WO2017040234A1 (en) | 2015-08-31 | 2016-08-26 | IMIDAZO[4,5-c] RING COMPOUNDS CONTAINING SUBSTITUTED GUANIDINE GROUPS |
| CN201680049829.8A CN107922416B (zh) | 2015-08-31 | 2016-08-26 | 含有取代的胍基团的咪唑并[4,5-c]环化合物 |
| CN202110672923.1A CN113402518B (zh) | 2015-08-31 | 2016-08-26 | 含有取代的胍基团的咪唑并[4,5-c]环化合物 |
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| CN201680049829.8A Division CN107922416B (zh) | 2015-08-31 | 2016-08-26 | 含有取代的胍基团的咪唑并[4,5-c]环化合物 |
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| CN201680049829.8A Active CN107922416B (zh) | 2015-08-31 | 2016-08-26 | 含有取代的胍基团的咪唑并[4,5-c]环化合物 |
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| EP (1) | EP3344623B1 (https=) |
| JP (1) | JP6956071B2 (https=) |
| CN (2) | CN113402518B (https=) |
| WO (1) | WO2017040234A1 (https=) |
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| CN108026092B (zh) | 2015-08-31 | 2021-01-26 | 3M创新有限公司 | 胍取代的咪唑并[4,5-c]环化合物 |
| KR102726248B1 (ko) | 2016-07-07 | 2024-11-05 | 더 보드 어브 트러스티스 어브 더 리랜드 스탠포드 주니어 유니버시티 | 항체-애쥬번트 접합체 |
| JP7010286B2 (ja) | 2016-08-26 | 2022-01-26 | スリーエム イノベイティブ プロパティズ カンパニー | グアニジノ基で置換された縮合［１，２］イミダゾ［４，５－ｃ］環状化合物 |
| EP3589631B1 (en) | 2017-03-01 | 2021-07-21 | 3M Innovative Properties Company | Imidazo[4,5-c]ring compounds containing guanidine substituted benzamide groups |
| EP3887369B1 (en) * | 2018-11-26 | 2024-05-08 | Solventum Intellectual Properties Company | N-1 branched alkyl ether substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| AU2020241686A1 (en) | 2019-03-15 | 2021-11-04 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting HER2 |
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| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
Family Cites Families (33)
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|---|---|---|---|---|
| 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 |
| EP0708772B1 (en) | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | IMIDAZO [4,5-c]PYRIDIN-4-AMINES |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5994361A (en) * | 1994-06-22 | 1999-11-30 | Biochem Pharma | Substituted purinyl derivatives with immunomodulating activity |
| KR100518903B1 (ko) | 1996-10-25 | 2005-10-06 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | Ｔｈ2 매개 질병 및 관련 질병의 치료용 면역 반응 조절 화합물 |
| EP0894797A4 (en) | 1997-01-09 | 2001-08-16 | Terumo Corp | NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS |
| 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 |
| 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 |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 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 |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6664264B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US7163947B2 (en) | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| CA2534625A1 (en) * | 2003-08-05 | 2005-02-24 | 3M Innovative Properties Company | Infection prophylaxis using immune response modifier compounds |
| BRPI0413558A (pt) | 2003-08-12 | 2006-10-17 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por hidroxilamina |
| EP2939693A1 (en) | 2003-08-14 | 2015-11-04 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| WO2005051317A2 (en) | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| WO2005051380A1 (en) | 2003-11-26 | 2005-06-09 | Biovitrum Ab | Substituted urea-octahydroindols as antagonists of melanin concentrating hormone receptor 1 (mch1r) |
| WO2005094531A2 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| CA2571360C (en) | 2004-06-18 | 2014-11-25 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines useful in inducing cytokine biosynthesis in animals |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| ATE555786T1 (de) * | 2004-09-02 | 2012-05-15 | 3M Innovative Properties Co | 1-alkoxy 1h-imidazo-ringsysteme und verfahren |
| CA2597587A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| WO2006121528A2 (en) * | 2005-04-01 | 2006-11-16 | Coley Pharmaceutical Group, Inc. | Ring closing and related methods and intermediates |
| KR20080083270A (ko) | 2005-11-04 | 2008-09-17 | 콜레이 파마시티컬 그룹, 인코포레이티드 | 하이드록시 및 알콕시 치환된 1에이치 이미다조퀴놀린 및방법 |
| ES2617451T3 (es) | 2010-08-17 | 2017-06-19 | 3M Innovative Properties Company | Composiciones lipidadas de compuestos modificadores de la respuesta inmunitaria, formulaciones, y métodos |
| US8728486B2 (en) | 2011-05-18 | 2014-05-20 | University Of Kansas | Toll-like receptor-7 and -8 modulatory 1H imidazoquinoline derived compounds |
| WO2013033345A1 (en) | 2011-08-30 | 2013-03-07 | Regents Of The University Of Minnesota | Immunomodulators and immunomodulator conjugates |
| CN108026092B (zh) | 2015-08-31 | 2021-01-26 | 3M创新有限公司 | 胍取代的咪唑并[4,5-c]环化合物 |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
Non-Patent Citations (1)
| Title |
|---|
| Nikunj M. Shukla 等.Relationship in Human Toll-Like Receptor 7-Active Imidazoquinoline Analogues .《J.Med.Chem》.2010,第53卷第4450-4465页. * |
Also Published As
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| EP3344623B1 (en) | 2021-02-17 |
| CN107922416B (zh) | 2021-07-02 |
| EP3344623A1 (en) | 2018-07-11 |
| US20180244669A1 (en) | 2018-08-30 |
| US10118925B2 (en) | 2018-11-06 |
| WO2017040234A1 (en) | 2017-03-09 |
| JP6956071B2 (ja) | 2021-10-27 |
| CN107922416A (zh) | 2018-04-17 |
| JP2018525427A (ja) | 2018-09-06 |
| CN113402518A (zh) | 2021-09-17 |
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