JP2010526129A5 - - Google Patents
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- Publication number
- JP2010526129A5 JP2010526129A5 JP2010507003A JP2010507003A JP2010526129A5 JP 2010526129 A5 JP2010526129 A5 JP 2010526129A5 JP 2010507003 A JP2010507003 A JP 2010507003A JP 2010507003 A JP2010507003 A JP 2010507003A JP 2010526129 A5 JP2010526129 A5 JP 2010526129A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- imidazo
- propyl
- quinolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 145
- -1 cyano, hydroxyl Chemical group 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 31
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 13
- 239000011780 sodium chloride Substances 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- DZDHFZCICVMMQD-UHFFFAOYSA-N 2-butyl-3H-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(NC(CCCC)=N3)C3=C(N)N=C21 DZDHFZCICVMMQD-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- XIQQEASYCSFTBJ-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propylamino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNCC1=CC=C(CC(=O)OC)C=C1 XIQQEASYCSFTBJ-UHFFFAOYSA-N 0.000 claims 2
- NIOHPZFOZHREKH-UHFFFAOYSA-N methyl 2-[4-[[acetyl-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 NIOHPZFOZHREKH-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 150000002829 nitrogen Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- AGGHKNBCHLWKHY-UHFFFAOYSA-N sodium;triacetyloxyboron(1-) Chemical compound [Na+].CC(=O)O[B-](OC(C)=O)OC(C)=O AGGHKNBCHLWKHY-UHFFFAOYSA-N 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 208000002205 Allergic Conjunctivitis Diseases 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 206010060945 Bacterial infection Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000002672 Hepatitis B Diseases 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims 1
- 208000006641 Skin Disease Diseases 0.000 claims 1
- 102100006355 TLR7 Human genes 0.000 claims 1
- 101700075266 TLR7 Proteins 0.000 claims 1
- 208000001756 Virus Disease Diseases 0.000 claims 1
- 230000000240 adjuvant Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 201000005794 allergic hypersensitivity disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims 1
- ITATYELQCJRCCK-UHFFFAOYSA-N methyl 2-hydroxy-2-phenylacetate Chemical compound COC(=O)C(O)C1=CC=CC=C1 ITATYELQCJRCCK-UHFFFAOYSA-N 0.000 claims 1
- 230000000051 modifying Effects 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000414 obstructive Effects 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91658607P | 2007-05-08 | 2007-05-08 | |
| US60/916,586 | 2007-05-08 | ||
| US2495708P | 2008-01-31 | 2008-01-31 | |
| US60/024,957 | 2008-01-31 | ||
| PCT/GB2008/050328 WO2008135791A1 (en) | 2007-05-08 | 2008-05-06 | Imidazoquinolines with immuno-modulating properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010526129A JP2010526129A (ja) | 2010-07-29 |
| JP2010526129A5 true JP2010526129A5 (pt-PT) | 2011-06-02 |
| JP5400763B2 JP5400763B2 (ja) | 2014-01-29 |
Family
ID=39596464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010507003A Expired - Fee Related JP5400763B2 (ja) | 2007-05-08 | 2008-05-06 | 免疫調節特性を有するイミダゾキノリン類 |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US8436178B2 (pt-PT) |
| EP (1) | EP2155743B1 (pt-PT) |
| JP (1) | JP5400763B2 (pt-PT) |
| KR (1) | KR20100016289A (pt-PT) |
| CN (1) | CN101687867B (pt-PT) |
| AR (1) | AR066492A1 (pt-PT) |
| AU (1) | AU2008247165B2 (pt-PT) |
| BR (1) | BRPI0811125A2 (pt-PT) |
| CA (1) | CA2686163A1 (pt-PT) |
| CL (1) | CL2008001357A1 (pt-PT) |
| CO (1) | CO6251247A2 (pt-PT) |
| CY (1) | CY1113339T1 (pt-PT) |
| DK (1) | DK2155743T3 (pt-PT) |
| EC (1) | ECSP099750A (pt-PT) |
| ES (1) | ES2393037T3 (pt-PT) |
| HK (1) | HK1138849A1 (pt-PT) |
| HR (1) | HRP20120895T1 (pt-PT) |
| IL (1) | IL201572A0 (pt-PT) |
| MX (1) | MX2009011802A (pt-PT) |
| MY (1) | MY150519A (pt-PT) |
| PE (1) | PE20090276A1 (pt-PT) |
| PL (1) | PL2155743T3 (pt-PT) |
| PT (1) | PT2155743E (pt-PT) |
| RU (1) | RU2475487C2 (pt-PT) |
| TW (1) | TW200902529A (pt-PT) |
| UY (1) | UY31069A1 (pt-PT) |
| WO (1) | WO2008135791A1 (pt-PT) |
| ZA (1) | ZA200907547B (pt-PT) |
Families Citing this family (55)
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|---|---|---|---|---|
| TWI414525B (zh) | 2004-03-26 | 2013-11-11 | Dainippon Sumitomo Pharma Co | ９-取代-８-氧基腺嘌呤化合物 |
| WO2008004948A1 (en) * | 2006-07-05 | 2008-01-10 | Astrazeneca Ab | 8-oxoadenine derivatives acting as modulators of tlr7 |
| TW200831105A (en) | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| EP2139894B1 (en) * | 2007-03-19 | 2011-10-26 | AstraZeneca AB | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7) modulators |
| DK2132209T3 (da) * | 2007-03-19 | 2014-04-14 | Astrazeneca Ab | 9-substituerede 8-oxo-adeninforbindelser som modulatorer af tlr7 (toll-like receptor 7) |
| PE20081887A1 (es) * | 2007-03-20 | 2009-01-16 | Dainippon Sumitomo Pharma Co | Nuevo compuesto de adenina |
| JPWO2008114819A1 (ja) | 2007-03-20 | 2010-07-08 | 大日本住友製薬株式会社 | 新規アデニン化合物 |
| BRPI0811125A2 (pt) * | 2007-05-08 | 2017-05-09 | Astrazeneca Ab | imidazoquinolinas com propriedades imunomoduladoras |
| US7968544B2 (en) * | 2007-06-29 | 2011-06-28 | Gilead Sciences, Inc. | Modulators of toll-like receptor 7 |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| PE20091156A1 (es) | 2007-12-17 | 2009-09-03 | Astrazeneca Ab | Sales de (3-{[[3-(6-amino-2-butoxi-8-oxo-7,8-dihidro-9h-purin-9-il)propil](3-morfolin-4-ilpropil)amino]metil}fenil)acetato de metilo |
| US20110054168A1 (en) * | 2008-01-17 | 2011-03-03 | Ayumu Kurimoto | Method for preparing adenine compound |
| KR20100125245A (ko) | 2008-01-17 | 2010-11-30 | 다이닛본 스미토모 세이야꾸 가부시끼가이샤 | 아데닌 화합물의 제조 방법 |
| MY150481A (en) * | 2008-03-03 | 2014-01-30 | Irm Llc | Compounds and compositions as tlr activity modulators |
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| TW201639852A (zh) | 2008-12-09 | 2016-11-16 | 吉李德科學股份有限公司 | 用於製備可用作類鐸受體調節劑之化合物的中間體化合物 |
| GB0908772D0 (en) | 2009-05-21 | 2009-07-01 | Astrazeneca Ab | New salts 756 |
| ES2443952T3 (es) | 2009-09-02 | 2014-02-21 | Novartis Ag | Composiciones inmunógenas que incluyen moduladores de la actividad de TLR |
| PL2477987T3 (pl) * | 2009-09-14 | 2018-06-29 | Gilead Sciences, Inc. | Modulatory receptorów toll-podobnych |
| 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 |
| WO2011068233A1 (en) * | 2009-12-03 | 2011-06-09 | Dainippon Sumitomo Pharma Co., Ltd. | Imidazoquinolines which act via toll - like receptors (tlr) |
| WO2011084725A1 (en) * | 2009-12-21 | 2011-07-14 | 3M Innovative Properties Company | 4-AMINO-2-(ETHOXYMETHYL)-1-(2-HYDROXY-2-METHYLPROPYL)-1H-IMIDAZO[4,5-c]QUINOLIN-5-IUM 1-HYDROXYNAPHTHALENE-2-CARBOXYLATE COMPOSITIONS AND METHODS |
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| EP2719395A1 (en) | 2010-09-01 | 2014-04-16 | Novartis AG | Adsorption of immunopotentiators to insoluble metal salts |
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| JP6191082B2 (ja) | 2011-03-02 | 2017-09-06 | グラクソスミスクライン バイオロジカルズ ソシエテ アノニム | より低用量の抗原および／またはアジュバントを有する混合ワクチン |
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| US20150030630A1 (en) | 2012-03-07 | 2015-01-29 | Novartis Ag | Adjuvanted formulations of rabies virus immunogens |
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| WO2013172479A1 (en) | 2012-05-18 | 2013-11-21 | Dainippon Sumitomo Pharma Co., Ltd. | Carboxylic acid compounds |
| AU2013311702A1 (en) | 2012-09-06 | 2015-02-19 | Novartis Ag | Combination vaccines with serogroup B meningococcus and D/T/P |
| WO2015103989A1 (en) | 2014-01-10 | 2015-07-16 | Shanghai Birdie Biotech, Inc. | Compounds and compositions for immunotherapy |
| TWI691335B (zh) | 2014-07-09 | 2020-04-21 | 英屬開曼群島商博笛生物科技有限公司 | 用於治療腫瘤的抗pd-l1組合 |
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| SI3194401T1 (sl) | 2014-09-16 | 2020-12-31 | Gilead Sciences, Inc. | Trdne oblike modulatorja toličnega receptorja |
| CN106943597A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-egfr组合 |
| CN106943596A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-cd20组合 |
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| TWI674261B (zh) | 2017-02-17 | 2019-10-11 | 美商英能腫瘤免疫股份有限公司 | Nlrp3 調節劑 |
| CA3057813A1 (en) | 2017-03-29 | 2018-10-04 | Sumitomo Dainippon Pharma Co., Ltd. | Vaccine adjuvant formulation |
| CN118515666A (zh) | 2017-04-27 | 2024-08-20 | 博笛生物科技有限公司 | 2-氨基-喹啉衍生物 |
| RU2020102453A (ru) | 2017-06-23 | 2021-07-23 | Бирди Байофармасьютикалз, Инк. | Фармацевтические композиции |
| US12012421B2 (en) | 2017-07-07 | 2024-06-18 | Hoffmann-La Roche Inc. | Solid forms of [(1S)-1-[(2S,4R,5R)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl] acetate |
| WO2019048036A1 (en) * | 2017-09-06 | 2019-03-14 | Biontech Ag | SUBSTITUTED IMIDAZOQUINOLINES |
| US12012420B2 (en) | 2017-11-21 | 2024-06-18 | Hoffmann-La Roche, Inc. | Solid forms of [(1S)-1-[(2S,4R,5R)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl] acetate |
| CA3086439A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| EP3730152A4 (en) | 2017-12-21 | 2022-01-12 | Sumitomo Dainippon Pharma Co., Ltd. | COMBINATION DRUGS WITH TLR7 AGONIST |
| US12059462B2 (en) | 2018-07-23 | 2024-08-13 | Japan As Represented By Director General Of National Institute Of Infectious Diseases | Composition containing influenza vaccine |
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