ES2392647T3 - Compuestos tetracíclicos quirales que inducen la biosíntesis de interferón - Google Patents
Compuestos tetracíclicos quirales que inducen la biosíntesis de interferón Download PDFInfo
- Publication number
- ES2392647T3 ES2392647T3 ES05855766T ES05855766T ES2392647T3 ES 2392647 T3 ES2392647 T3 ES 2392647T3 ES 05855766 T ES05855766 T ES 05855766T ES 05855766 T ES05855766 T ES 05855766T ES 2392647 T3 ES2392647 T3 ES 2392647T3
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- Spain
- Prior art keywords
- aryl
- group
- alkyl
- heteroaryl
- heterocyclyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 277
- 230000015572 biosynthetic process Effects 0.000 title claims description 25
- 102000014150 Interferons Human genes 0.000 title description 3
- 108010050904 Interferons Proteins 0.000 title description 3
- 229940079322 interferon Drugs 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 222
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 208
- 125000003118 aryl group Chemical group 0.000 claims abstract description 194
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 186
- 125000001424 substituent group Chemical group 0.000 claims abstract description 143
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 125
- -1 arylalkylenyl Chemical group 0.000 claims abstract description 115
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 111
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 104
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 84
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 79
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 77
- 150000002367 halogens Chemical group 0.000 claims abstract description 70
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 67
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 52
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 51
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 45
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 38
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims abstract description 35
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 35
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 35
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 35
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 20
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims abstract description 19
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 18
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims abstract description 18
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 18
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims abstract description 18
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims abstract description 18
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims abstract description 18
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims abstract description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 48
- 241001465754 Metazoa Species 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 201000010099 disease Diseases 0.000 claims description 29
- 102000004127 Cytokines Human genes 0.000 claims description 28
- 108090000695 Cytokines Proteins 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000005549 heteroarylene group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 16
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
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- 230000003612 virological effect Effects 0.000 claims description 11
- 125000005466 alkylenyl group Chemical group 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 230000001613 neoplastic effect Effects 0.000 claims description 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 230000001939 inductive effect Effects 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 219
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 163
- 239000000243 solution Substances 0.000 description 163
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 124
- 239000011541 reaction mixture Substances 0.000 description 109
- 230000002829 reductive effect Effects 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 239000012267 brine Substances 0.000 description 46
- 239000010410 layer Substances 0.000 description 46
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 45
- 229910052938 sodium sulfate Inorganic materials 0.000 description 45
- 235000011152 sodium sulphate Nutrition 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 238000005160 1H NMR spectroscopy Methods 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 35
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 18
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 17
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64061404P | 2004-12-30 | 2004-12-30 | |
| US640614P | 2004-12-30 | ||
| US69725705P | 2005-07-07 | 2005-07-07 | |
| US697257P | 2005-07-07 | ||
| PCT/US2005/047258 WO2006074003A2 (en) | 2004-12-30 | 2005-12-29 | CHIRAL FUSED [1,2]IMIDAZO[4,5-c] RING COMPOUNDS |
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| ES2392647T3 true ES2392647T3 (es) | 2012-12-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| ES05855766T Active ES2392647T3 (es) | 2004-12-30 | 2005-12-29 | Compuestos tetracíclicos quirales que inducen la biosíntesis de interferón |
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| EP (1) | EP1831226B1 (enExample) |
| JP (1) | JP5543068B2 (enExample) |
| AU (1) | AU2005322898B2 (enExample) |
| CA (1) | CA2592904C (enExample) |
| ES (1) | ES2392647T3 (enExample) |
| WO (1) | WO2006074003A2 (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH078366B2 (ja) | 1986-10-03 | 1995-02-01 | 株式会社クボタ | 熱間圧延用溶接肉盛ロ−ル |
| US6797718B2 (en) | 2002-06-07 | 2004-09-28 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| AU2004266658A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
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| JP2007504269A (ja) | 2003-09-05 | 2007-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | Ｃｄ５＋ｂ細胞リンパ腫の治療方法 |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| AU2004315876B2 (en) | 2003-10-03 | 2011-05-26 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| AU2004291101A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| EP1682544A4 (en) | 2003-11-14 | 2009-05-06 | 3M Innovative Properties Co | HYDROXYLAMINE SUBSTITUTED IMIDAZO RING COMPOUNDS |
| AU2004293078B2 (en) | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| CA2552101A1 (en) * | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds |
| EP1701955A1 (en) | 2003-12-29 | 2006-09-20 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
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| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
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| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
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| US8034938B2 (en) * | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| AU2005322898B2 (en) * | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| EP1877056A2 (en) | 2005-02-09 | 2008-01-16 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazoloý4,5-c¨ring compounds and methods |
| CA2597324C (en) | 2005-02-09 | 2015-06-30 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| AU2006213746A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods |
| EP1845988A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Substituted imidazoquinolines and imidazonaphthyridines |
| JP2008531567A (ja) | 2005-02-23 | 2008-08-14 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ヒドロキシアルキル置換イミダゾキノリン化合物および方法 |
| EP1851220A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| EP1851224A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| WO2006091647A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| CA2602683A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| AU2006287270A1 (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 |
| EP1948173B1 (en) | 2005-11-04 | 2013-07-17 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2007106852A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Substituted fused[1,2]imidazo[4,5-c] ring compounds and methods |
| 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 |
| US8178539B2 (en) | 2006-09-06 | 2012-05-15 | 3M Innovative Properties Company | Substituted 3,4,6,7-tetrahydro-5H-1,2a,4a,8-tetraazacyclopenta[cd]phenalenes and methods |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| CN103800906B (zh) | 2009-03-25 | 2017-09-22 | 德克萨斯大学系统董事会 | 用于刺激哺乳动物对病原体的先天免疫抵抗力的组合物 |
| RS55819B1 (sr) | 2010-08-17 | 2017-08-31 | 3M Innovative Properties Co | Kompozicije sa lipidiranim modifikatorom imuno-odgovora, formulacije, i postupci |
| MX347240B (es) | 2011-06-03 | 2017-04-20 | 3M Innovative Properties Co | Ligadores heterobifuncionales con segmentos polietilenglicol y conjugados modificadores de la respuesta inmunitaria elaborados a partir de los mismos. |
| MX355623B (es) | 2011-06-03 | 2018-04-25 | 3M Innovative Properties Co | Hidrazino-1h-imidazoquinolin-4-aminas y conjugados elaborados a partir de las mismas. |
| SI2941233T1 (sl) | 2013-01-07 | 2021-01-29 | The Trustees Of The University Of Pennsylvania | Sestavki in postopki za zdravljenje kutanega T celičnega limfoma |
| WO2016044839A2 (en) | 2014-09-19 | 2016-03-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for treating viral infections through stimulated innate immunity in combination with antiviral compounds |
| US10526309B2 (en) | 2015-10-02 | 2020-01-07 | The University Of North Carolina At Chapel Hill | Pan-TAM inhibitors and Mer/Axl dual inhibitors |
| AU2017292934B9 (en) | 2016-07-07 | 2024-08-29 | Bolt Biotherapeutics, Inc. | Antibody adjuvant conjugates |
| EP3504215B1 (en) * | 2016-08-26 | 2022-04-06 | 3M Innovative Properties Company | Fused [1,2]imidazo[4,5-c]ring compounds substituted with guanidino groups |
| JP7197244B2 (ja) | 2017-12-20 | 2022-12-27 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤として使用するための分岐鎖連結基を有するアミド置換イミダゾ［４，５－ｃ］キノリン化合物 |
| WO2019166946A1 (en) | 2018-02-28 | 2019-09-06 | Pfizer Inc. | Il-15 variants and uses thereof |
| EP3759107B1 (en) * | 2018-02-28 | 2024-12-04 | Solventum Intellectual Properties Company | Substituted imidazo[4,5-c]quinoline compounds with an n-1 branched group |
| TWI803637B (zh) | 2018-05-23 | 2023-06-01 | 美商輝瑞大藥廠 | 特異性針對gucy2c之抗體及其用途 |
| EP3797121B1 (en) | 2018-05-23 | 2024-06-19 | Pfizer Inc. | Antibodies specific for cd3 and uses thereof |
| WO2020109898A1 (en) | 2018-11-26 | 2020-06-04 | 3M Innovative Properties Company | N-1 branched alkyl ether substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| US20220370606A1 (en) | 2018-12-21 | 2022-11-24 | Pfizer Inc. | Combination Treatments Of Cancer Comprising A TLR Agonist |
| EP3937984A1 (en) | 2019-03-15 | 2022-01-19 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting her2 |
| KR20220114049A (ko) | 2019-12-17 | 2022-08-17 | 화이자 인코포레이티드 | Cd47, pd-l1에 특이적인 항체, 및 그의 용도 |
| IL299939A (en) | 2020-07-17 | 2023-03-01 | Pfizer | Therapeutic antibodies and their uses |
| CN112679522B (zh) * | 2020-12-29 | 2023-02-14 | 南京正济医药研究有限公司 | 一种巴洛沙韦中间体的制备方法 |
| WO2025104289A1 (en) | 2023-11-17 | 2025-05-22 | Medincell S.A. | Antineoplastic combinations |
Family Cites Families (340)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| DE1645976A1 (de) | 1966-06-18 | 1971-01-21 | Ajinomoto Kk | Verfahren zur Herstellung von Adenosin und 2',3'-O-Isopropylidenadenosin |
| ZA704419B (en) | 1969-07-21 | 1971-04-28 | Ici Australia Ltd | Injectable aqueous solutions of tetramisole |
| US3692907A (en) | 1970-10-27 | 1972-09-19 | Richardson Merrell Inc | Treating viral infections with bis-basic ethers and thioethers of fluorenone and fluorene and pharmaceutical compositons of the same |
| US3917624A (en) | 1972-09-27 | 1975-11-04 | Pfizer | Process for producing 2-amino-nicotinonitrile intermediates |
| US4006237A (en) | 1973-10-11 | 1977-02-01 | Beecham Group Limited | Tetrahydrocarbostyril derivatives for the prophylaxis of asthma, hayfever and rhinitis |
| US3891660A (en) | 1974-02-07 | 1975-06-24 | Squibb & Sons Inc | Derivatives of 1H-imidazo{8 4,5-c{9 pyridine-7-carboxylic acids and esters |
| US3899508A (en) | 1974-04-12 | 1975-08-12 | Lilly Co Eli | 5-(2-Aminophenyl)pyrazole-3-carboxylic acids and esters thereof |
| DE2423389A1 (de) | 1974-05-14 | 1975-12-04 | Hoechst Ag | Arzneimittel mit psychotroper wirkung und verfahren zu ihrer herstellung |
| JPS6016438B2 (ja) | 1976-10-14 | 1985-04-25 | ウェルファイド株式会社 | イミダゾキノリン誘導体 |
| US4381344A (en) | 1980-04-25 | 1983-04-26 | Burroughs Wellcome Co. | Process for producing deoxyribosides using bacterial phosphorylase |
| DE3204126A1 (de) | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Pyrazoloxazine, -thiazine, -chinoline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4758574A (en) | 1982-05-03 | 1988-07-19 | Eli Lilly And Company | 2-phenylimidazio (4,5-c) pyridines |
| US4563525A (en) | 1983-05-31 | 1986-01-07 | Ici Americas Inc. | Process for preparing pyrazolopyridine compounds |
| 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 |
| 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 |
| CA1271477A (en) | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| JPS61112075A (ja) | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| US4593821A (en) | 1985-04-25 | 1986-06-10 | Laros Equipment Company, Inc. | Belt separator for blow molding parts |
| US4668686A (en) | 1985-04-25 | 1987-05-26 | Bristol-Myers Company | Imidazoquinoline antithrombrogenic cardiotonic agents |
| US4698346A (en) | 1985-05-08 | 1987-10-06 | Usv Pharmaceutical Corporation | Thiazolo[5,4-h]quinoline compounds useful as anti-allergy agents |
| US4826830A (en) | 1985-07-31 | 1989-05-02 | Jui Han | Topical application of glyciphosphoramide |
| CA1306260C (en) | 1985-10-18 | 1992-08-11 | Shionogi & Co., Ltd. | Condensed imidazopyridine derivatives |
| HU197019B (en) | 1985-11-12 | 1989-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing thiqzolo (4,5-c) quinoline derivatives and pharmaceuticals comprising same |
| US4837378A (en) | 1986-01-15 | 1989-06-06 | Curatek Pharmaceuticals, Inc. | Topical metronidazole formulations and therapeutic uses thereof |
| JPS6310787A (ja) | 1986-03-06 | 1988-01-18 | Takeda Chem Ind Ltd | ヌクレオシド類縁体、その製造法および抗ウイルス剤 |
| US4775674A (en) | 1986-05-23 | 1988-10-04 | Bristol-Myers Company | Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors |
| CA1287061C (en) | 1986-06-27 | 1991-07-30 | Roche Holding Ltd. | Pyridine ethanolamine derivatives |
| US5500228A (en) | 1987-05-26 | 1996-03-19 | American Cyanamid Company | Phase separation-microencapsulated pharmaceuticals compositions useful for alleviating dental disease |
| US4880779A (en) | 1987-07-31 | 1989-11-14 | Research Corporation Technologies, Inc. | Method of prevention or treatment of AIDS by inhibition of human immunodeficiency virus |
| US4774339A (en) | 1987-08-10 | 1988-09-27 | Molecular Probes, Inc. | Chemically reactive dipyrrometheneboron difluoride dyes |
| JPH01180156A (ja) | 1988-01-12 | 1989-07-18 | Nec Corp | パケットスイッチング回路 |
| US5536743A (en) | 1988-01-15 | 1996-07-16 | Curatek Pharmaceuticals Limited Partnership | Intravaginal treatment of vaginal infections with buffered metronidazole compositions |
| US5225183A (en) | 1988-12-06 | 1993-07-06 | Riker Laboratories, Inc. | Medicinal aerosol formulations |
| 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 |
| 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 |
| DE69029212T2 (de) | 1989-02-27 | 1997-05-22 | Riker Laboratories Inc | 4-Amino-1H-Imidazo(4,5-c)chinoline als antivirale Mittel |
| US5457183A (en) | 1989-03-06 | 1995-10-10 | Board Of Regents, The University Of Texas System | Hydroxylated texaphyrins |
| US4929624A (en) | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | 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 |
| US5750134A (en) | 1989-11-03 | 1998-05-12 | Riker Laboratories, Inc. | Bioadhesive composition and patch |
| JPH05503517A (ja) | 1989-12-18 | 1993-06-10 | バージニア・コモンウェルス・ユニバーシティ | シグマレセプターリガンド及びその用途 |
| US5274113A (en) | 1991-11-01 | 1993-12-28 | Molecular Probes, Inc. | Long wavelength chemically reactive dipyrrometheneboron difluoride dyes and conjugates |
| BR9106391A (pt) | 1990-04-30 | 1993-04-27 | Isis Pharmaceuticals Inc | Oligonucleotideo ou analogo de oligonucleotideo,processo para modular o metaboslismo do acido araquidonico em um animal,e,processo para tratar um anumal suspeito de ter uma doenca que e modulada por mudancas na sintese ou no metabolismo do acido arquidonico |
| EP0461040A1 (fr) | 1990-06-08 | 1991-12-11 | Roussel Uclaf | Dérivés de l'imidazole, leur procédé de préparation, les intermédiaires obtenus, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant |
| JP2660086B2 (ja) | 1990-07-03 | 1997-10-08 | 明治製菓株式会社 | 脳及び心機能障害改善剤 |
| CA2093132C (en) | 1990-10-05 | 2002-02-26 | John F. Gerster | Process for the preparation of imidazo[4,5-c]quinolin-4-amines |
| MX9203481A (es) | 1990-10-18 | 1992-07-01 | Minnesota Mining & Mfg | Formulaciones. |
| US5248782A (en) | 1990-12-18 | 1993-09-28 | Molecular Probes, Inc. | Long wavelength heteroaryl-substituted dipyrrometheneboron difluoride dyes |
| 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 |
| JPH04327587A (ja) | 1991-04-26 | 1992-11-17 | Asahi Chem Ind Co Ltd | ６’−ｃ−アルキル−３−デアザネプラノシンａ誘導体、その製造法およびその用途 |
| US5187288A (en) | 1991-05-22 | 1993-02-16 | Molecular Probes, Inc. | Ethenyl-substituted dipyrrometheneboron difluoride dyes and their synthesis |
| US5268376A (en) | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| TW300219B (enExample) | 1991-09-14 | 1997-03-11 | Hoechst Ag | |
| PH31245A (en) | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US5266575A (en) | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| US5378848A (en) | 1992-02-12 | 1995-01-03 | Shionogi & Co., Ltd. | Condensed imidazopyridine derivatives |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| ATE155681T1 (de) | 1992-05-18 | 1997-08-15 | Minnesota Mining & Mfg | Einrichtung zur transmucosalen wirkstoffabgabe |
| US5352680A (en) | 1992-07-15 | 1994-10-04 | Regents Of The University Of Minnesota | Delta opioid receptor antagonists to block opioid agonist tolerance and dependence |
| US6608201B2 (en) | 1992-08-28 | 2003-08-19 | 3M Innovative Properties Company | Process for preparing 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| CA2156408C (en) | 1993-03-17 | 2005-02-15 | Daniel C. Duan | Aerosol formulation containing a polyester dispersing aid |
| DE4309969A1 (de) | 1993-03-26 | 1994-09-29 | Bayer Ag | Substituierte heteroanellierte Imidazole |
| DE69314318T2 (de) | 1993-04-27 | 1998-04-09 | Agfa Gevaert Nv | Verfahren zum Einfügen von einer Wasserumlöslichen Verbindung in eine hydrophile Schicht |
| US5648516A (en) | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| ES2149276T3 (es) * | 1993-07-15 | 2000-11-01 | Minnesota Mining & Mfg | Imidazo(4,5-c)piridin-4-aminas. |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| CA2131680C (en) | 1993-09-17 | 2006-11-07 | Gerhard Stucky | Process for preparing imidazopyridine derivatives |
| US5837809A (en) | 1995-08-11 | 1998-11-17 | Oregon Health Sciences University | Mammalian opioid receptor ligand and uses |
| JPH07163368A (ja) | 1993-12-15 | 1995-06-27 | Hayashibara Biochem Lab Inc | 組換えｄｎａとその組換えｄｎａを含む形質転換体 |
| TW574214B (en) | 1994-06-08 | 2004-02-01 | Pfizer | Corticotropin releasing factor antagonists |
| US6207646B1 (en) | 1994-07-15 | 2001-03-27 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| DE69535036T3 (de) | 1994-07-15 | 2011-07-07 | The University of Iowa Research Foundation, IA | Immunomodulatorische oligonukleotide |
| US6239116B1 (en) | 1994-07-15 | 2001-05-29 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| US5612377A (en) | 1994-08-04 | 1997-03-18 | Minnesota Mining And Manufacturing Company | Method of inhibiting leukotriene biosynthesis |
| US5644063A (en) | 1994-09-08 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]pyridin-4-amine intermediates |
| GB9420168D0 (en) | 1994-10-06 | 1994-11-23 | Boots Co Plc | Therapeutic agents |
| US5571819A (en) | 1994-11-22 | 1996-11-05 | Sabb; Annmarie L. | Imidazopyridines as muscarinic agents |
| US5482936A (en) | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| US6071949A (en) | 1995-03-14 | 2000-06-06 | The United States Of America As Represented By The Department Of Health And Human Services | Use of lipoxygenase inhibitors as anti-cancer therapeutic and intervention agents |
| US5585612A (en) | 1995-03-20 | 1996-12-17 | Harp Enterprises, Inc. | Method and apparatus for voting |
| FR2732605B1 (fr) | 1995-04-07 | 1997-05-16 | Pasteur Merieux Serums Vacc | Composition destinee a l'induction d'une reponse immunitaire mucosale |
| US5766789A (en) | 1995-09-29 | 1998-06-16 | Energetics Systems Corporation | Electrical energy devices |
| DK0778277T3 (da) | 1995-12-08 | 2003-10-27 | Pfizer | Substituerede heterocycliske derivater som CRF antagonister |
| 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 |
| US5939047A (en) | 1996-04-16 | 1999-08-17 | Jernberg; Gary R. | Local delivery of chemotherapeutic agents for treatment of periodontal disease |
| US5861268A (en) | 1996-05-23 | 1999-01-19 | Biomide Investment Limited Partnership | Method for induction of tumor cell apoptosis with chemical inhibitors targeted to 12-lipoxygenase |
| 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 |
| ATE283855T1 (de) | 1996-07-03 | 2004-12-15 | Sumitomo Pharma | Neue purinderivate |
| US6387938B1 (en) | 1996-07-05 | 2002-05-14 | Mochida Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| HUP9904665A3 (en) | 1996-10-25 | 2000-11-28 | Minnesota Mining And Mfg Co Sa | Immune response modifier compounds for treatment of th2 mediated and related diseases |
| 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 |
| US6406705B1 (en) | 1997-03-10 | 2002-06-18 | University Of Iowa Research Foundation | Use of nucleic acids containing unmethylated CpG dinucleotide as an adjuvant |
| US6426334B1 (en) | 1997-04-30 | 2002-07-30 | Hybridon, Inc. | Oligonucleotide mediated specific cytokine induction and reduction of tumor growth in a mammal |
| US6303347B1 (en) | 1997-05-08 | 2001-10-16 | Corixa Corporation | Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors |
| US6113918A (en) | 1997-05-08 | 2000-09-05 | Ribi Immunochem Research, Inc. | Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors |
| EP1003531B1 (en) | 1997-05-20 | 2007-08-22 | Ottawa Health Research Institute | Processes for preparing nucleic acid constructs |
| US6123957A (en) | 1997-07-16 | 2000-09-26 | Jernberg; Gary R. | Delivery of agents and method for regeneration of periodontal tissues |
| KR100528112B1 (ko) | 1997-08-20 | 2006-03-17 | 소니 가부시끼 가이샤 | 원반형 기록 매체의 제조 장치 및 방법 |
| US6309623B1 (en) | 1997-09-29 | 2001-10-30 | Inhale Therapeutic Systems, Inc. | Stabilized preparations for use in metered dose inhalers |
| CA2311742C (en) | 1997-11-28 | 2009-06-16 | Sumitomo Pharmaceuticals Co., Ltd. | 6-amino-9-benzyl-8-hydroxypurine derivatives |
| US6121323A (en) | 1997-12-03 | 2000-09-19 | 3M Innovative Properties Company | Bishydroxyureas |
| 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 |
| TW572758B (en) | 1997-12-22 | 2004-01-21 | Sumitomo Pharma | Type 2 helper T cell-selective immune response inhibitors comprising purine derivatives |
| 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 |
| US6114058A (en) | 1998-05-26 | 2000-09-05 | Siemens Westinghouse Power Corporation | Iron aluminide alloy container for solid oxide fuel cells |
| 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 |
| US5962636A (en) | 1998-08-12 | 1999-10-05 | Amgen Canada Inc. | Peptides capable of modulating inflammatory heart disease |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| 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 |
| EP1495758A3 (en) | 1999-01-08 | 2005-04-13 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| NZ512628A (en) | 1999-01-08 | 2004-03-26 | 3M Innovative Properties Co | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6558951B1 (en) | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| US6294271B1 (en) | 1999-02-12 | 2001-09-25 | Shin-Etsu Chemical Co., Ltd. | Flip-chip type semiconductor device sealing material and flip-chip type semiconductor device |
| 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 |
| EP1171609B1 (en) | 1999-04-12 | 2008-06-25 | Lexicon Pharmaceuticals, Inc. | Lipoxygenase proteins and polynucleotides encoding the same |
| 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 |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6315985B1 (en) | 1999-06-18 | 2001-11-13 | 3M Innovative Properties Company | C-17/21 OH 20-ketosteroid solution aerosol products with enhanced chemical stability |
| ES2233426T3 (es) | 1999-08-13 | 2005-06-16 | Hybridon, Inc. | Modulacion de la estimulacion inmunitaria medida por cpg de oligonucleotido por modificacion de la posicion de los nucleosidos. |
| US6432989B1 (en) | 1999-08-27 | 2002-08-13 | Pfizer Inc | Use of CRF antagonists to treat circadian rhythm disorders |
| CO5271670A1 (es) | 1999-10-29 | 2003-04-30 | Pfizer Prod Inc | Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas |
| EP1666028B1 (en) | 1999-10-29 | 2010-03-24 | Novartis AG | Dry powder compositions having improved dispersivity |
| US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6313156B1 (en) | 1999-12-23 | 2001-11-06 | Icos Corporation | Thiazole compounds as cyclic-AMP-specific phosphodiesterase inhibitors |
| US20040023870A1 (en) | 2000-01-21 | 2004-02-05 | Douglas Dedera | Methods of therapy and diagnosis using targeting of cells that express toll-like receptor proteins |
| GB0001704D0 (en) | 2000-01-25 | 2000-03-15 | Glaxo Group Ltd | Protein |
| KR20020073211A (ko) | 2000-02-09 | 2002-09-19 | 호쿠리쿠 세이야쿠 가부시키가이샤 | 1 에이치-이미다조피리딘유도체 |
| WO2001070663A2 (en) | 2000-03-17 | 2001-09-27 | Corixa Corporation | Novel amphipathic aldehydes and their use as adjuvants and immunoeffectors |
| US20010046968A1 (en) | 2000-03-23 | 2001-11-29 | Zagon Ian S. | Opioid growth factor modulates angiogenesis |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| EP1270578A4 (en) | 2000-03-30 | 2004-11-03 | Shionogi & Co | NOVEL PROCESS FOR PRODUCING MOLTEN IMIDAZOPYRIDINE DERIVATIVE AND NOVEL CRYSTALLINE FORM |
| US20020137101A1 (en) | 2000-05-19 | 2002-09-26 | Meyers Rachel A. | 46638, a novel human lipoxygenase family member and uses thereof |
| DE10020465A1 (de) | 2000-04-26 | 2001-11-08 | Osram Opto Semiconductors Gmbh | Strahlungsemittierendes Halbleiterbauelement mit Lumineszenzkonversionselement |
| DE10029580C1 (de) | 2000-06-15 | 2002-01-10 | Ferton Holding Sa | Vorrichtung zum Entfernen von Körpersteinen mit einem intrakorporalen Lithotripter |
| US6387383B1 (en) | 2000-08-03 | 2002-05-14 | Dow Pharmaceutical Sciences | Topical low-viscosity gel composition |
| US6900016B1 (en) | 2000-09-08 | 2005-05-31 | Applera Corporation | Polymorphisms in known genes associated with inflammatory autoimmune disease, methods of detection and uses thereof |
| WO2002022809A2 (en) | 2000-09-15 | 2002-03-21 | Coley Pharmaceutical Gmbh | PROCESS FOR HIGH THROUGHPUT SCREENING OF CpG-BASED IMMUNO-AGONIST/ANTAGONIST |
| US20020055517A1 (en) | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| GB0023008D0 (en) | 2000-09-20 | 2000-11-01 | Glaxo Group Ltd | Improvements in vaccination |
| WO2002046479A1 (fr) | 2000-12-07 | 2002-06-13 | Aoyama Seisakusho Co., Ltd. | Procede de cuisson d'element d'acier |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6664264B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| UA75622C2 (en) | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US20020107262A1 (en) | 2000-12-08 | 2002-08-08 | 3M Innovative Properties Company | Substituted imidazopyridines |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| US20060142202A1 (en) | 2000-12-08 | 2006-06-29 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6660747B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6667312B2 (en) | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US20020110840A1 (en) | 2000-12-08 | 2002-08-15 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| US6664260B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| KR100455713B1 (ko) | 2001-01-29 | 2004-11-06 | 호남석유화학 주식회사 | 올레핀 중합용 다중핵 메탈로센 촉매 및 이를 이용한중합방법 |
| US20020182274A1 (en) | 2001-03-21 | 2002-12-05 | Kung-Ming Lu | Methods for inhibiting cancer growth, reducing infection and promoting general health with a fermented soy extract |
| DE60228229D1 (de) | 2001-04-17 | 2008-09-25 | Dainippon Sumitomo Pharma Co | Neue adeninderivate |
| US20020193729A1 (en) | 2001-04-20 | 2002-12-19 | Cormier Michel J.N. | Microprojection array immunization patch and method |
| ATE463505T1 (de) | 2001-04-20 | 2010-04-15 | Inst Systems Biology | Toll-ähnlichen-rezeptor-5-liganden und verwendungsverfahren |
| US6627639B2 (en) | 2001-04-26 | 2003-09-30 | Wyeth | Uses for indoletetrahydropyridine derivatives of 2,3-dihydro-7H-[1,4]dioxino-[2,3-e]indole |
| US7226928B2 (en) | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| US6756399B2 (en) | 2001-06-29 | 2004-06-29 | The United States Of America As Represented By The Department Of Health And Human Services | Use of lipoxygenase inhibitors and PPAR ligands as anti-cancer therapeutic and intervention agents |
| CN1250550C (zh) | 2001-07-16 | 2006-04-12 | 盐野义制药株式会社 | 脒衍生物的制备方法 |
| WO2003020889A2 (en) | 2001-08-30 | 2003-03-13 | 3M Innovative Properties Company | Methods of maturing plasmacytoid dendritic cells using immune response modifier molecules |
| WO2003030902A1 (en) | 2001-10-09 | 2003-04-17 | Tularik Inc. | Imidazole derivates as anti-inflammatory agents |
| US20030139364A1 (en) | 2001-10-12 | 2003-07-24 | University Of Iowa Research Foundation | Methods and products for enhancing immune responses using imidazoquinoline compounds |
| EP1719511B1 (en) | 2001-11-16 | 2008-12-10 | 3M Innovative Properties Company | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, a pharmaceutical composition comprising the same and use thereof |
| US20050009858A1 (en) | 2001-11-17 | 2005-01-13 | Martinez-Colon Maria I | Imiquimod therapies |
| GEP20074099B (en) | 2001-11-27 | 2007-05-10 | Anadys Pharmaceuticals Inc | 3-β-D-RIBOFURANO-SYLTHIAZOLO[4,5-d]PYRIDIMINE NUCLEOSIDES AND USES THEREOF |
| DK1450804T3 (da) | 2001-11-29 | 2009-01-05 | 3M Innovative Properties Co | Farmaceutiske formulelringer, der omfatter et immunsvarmodificerende middel |
| US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6775514B2 (en) | 2002-01-11 | 2004-08-10 | Xerox Corporation | Substrate size monitoring system for use in copier/printers |
| US6525028B1 (en) | 2002-02-04 | 2003-02-25 | Corixa Corporation | Immunoeffector compounds |
| US20050281813A1 (en) | 2002-02-14 | 2005-12-22 | Nuvelo, Inc. | Methods of therapy and diagnosis using targeting of cells that express toll-like receptor proteins |
| EP1478327B1 (en) | 2002-02-22 | 2015-04-29 | Meda AB | Method of reducing and treating uvb-induced immunosuppression |
| ATE491471T1 (de) | 2002-03-19 | 2011-01-15 | Powderject Res Ltd | Adjuvantien für dns impstoffe basierend auf imidazochinoline |
| US20030185835A1 (en) | 2002-03-19 | 2003-10-02 | Braun Ralph P. | Adjuvant for vaccines |
| RU2302865C2 (ru) | 2002-04-04 | 2007-07-20 | Коли Фармасьютикал Гмбх | Иммуностимулирующие g, u-содержащие олигорибонуклеотиды |
| CA2484192C (en) | 2002-04-30 | 2012-10-02 | Unigen Pharmaceuticals, Inc. | Formulation of a mixture of free-b-ring flavonoids and flavans as a therapeutic agent |
| GB0211649D0 (en) | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| WO2003101949A2 (en) | 2002-05-29 | 2003-12-11 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| US6797718B2 (en) | 2002-06-07 | 2004-09-28 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| PT1543002E (pt) | 2002-07-23 | 2006-11-30 | Teva Gyogyszergyar Zartkoeruen | Preparação de intermediários 1h-imidazo ( 4,5-c )quinolin-4-aminas via 1h- imidazo (4,5-c ) quinolina-4-ftalimida |
| JP2005537287A (ja) | 2002-07-26 | 2005-12-08 | テバ ジョジセルジャール レースベニュタールシャシャーグ | 新規１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−シアノ及び１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−カルボキサミド中間体による１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−アミン類の製造 |
| ATE488246T1 (de) | 2002-08-15 | 2010-12-15 | 3M Innovative Properties Co | Immunstimulatorische zusammensetzungen und verfahren zur stimulierung einer immunantwort |
| EP1542688A4 (en) | 2002-09-26 | 2010-06-02 | 3M Innovative Properties Co | 1H-imidazo dimers |
| US7199119B2 (en) | 2002-10-31 | 2007-04-03 | Amgen Inc. | Antiinflammation agents |
| WO2004043913A2 (en) | 2002-11-08 | 2004-05-27 | Trimeris, Inc. | Hetero-substituted benzimidazole compounds and antiviral uses thereof |
| AU2003287316A1 (en) | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| AU2003287324A1 (en) | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| US7091214B2 (en) | 2002-12-20 | 2006-08-15 | 3M Innovative Properties Co. | Aryl substituted Imidazoquinolines |
| EP1578419A4 (en) | 2002-12-30 | 2008-11-12 | 3M Innovative Properties Co | IMMUNOSTIMULATING COMBINATIONS |
| US7375180B2 (en) | 2003-02-13 | 2008-05-20 | 3M Innovative Properties Company | Methods and compositions related to IRM compounds and Toll-like receptor 8 |
| EP1599726A4 (en) | 2003-02-27 | 2009-07-22 | 3M Innovative Properties Co | SELECTIVE MODULATION OF TLR-MEDIATED BIOLOGICAL ACTIVITY |
| WO2004078138A2 (en) | 2003-03-04 | 2004-09-16 | 3M Innovative Properties Company | Prophylactic treatment of uv-induced epidermal neoplasia |
| US20040176367A1 (en) | 2003-03-07 | 2004-09-09 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| US7163947B2 (en) | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| AU2004220466A1 (en) | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods for diagnosing skin lesions |
| BRPI0408476A (pt) | 2003-03-13 | 2006-04-04 | 3M Innovative Properties Co | métodos para melhorar a qualidade da pele |
| US7179253B2 (en) | 2003-03-13 | 2007-02-20 | 3M Innovative Properties Company | Method of tattoo removal |
| US20040192585A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| EP1613956A2 (en) | 2003-03-25 | 2006-01-11 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
| US7893096B2 (en) | 2003-03-28 | 2011-02-22 | Novartis Vaccines And Diagnostics, Inc. | Use of small molecule compounds for immunopotentiation |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| WO2004108072A2 (en) | 2003-04-10 | 2004-12-16 | 3M Innovative Properties Company | Delivery of immune response modifier compounds using metal-containing particulate support materials |
| US20040214851A1 (en) | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| US7731967B2 (en) | 2003-04-30 | 2010-06-08 | Novartis Vaccines And Diagnostics, Inc. | Compositions for inducing immune responses |
| US6943255B2 (en) | 2003-06-06 | 2005-09-13 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| US20050032829A1 (en) | 2003-06-06 | 2005-02-10 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| EA200600069A1 (ru) | 2003-06-20 | 2006-08-25 | Коли Фармасьютикал Гмбх | Низкомолекулярные антагонисты toll-подобных рецепторов (tlr) |
| MY157827A (en) | 2003-06-27 | 2016-07-29 | 3M Innovative Properties Co | Sulfonamide substituted imidazoquinolines |
| US20050106300A1 (en) | 2003-06-30 | 2005-05-19 | Purdue Research Foundation | Method for producing a material having an increased solubility in alcohol |
| BRPI0413143A (pt) | 2003-07-31 | 2006-10-03 | 3M Innovative Properties Co | composições para encapsulação e liberação controlada |
| US20050070460A1 (en) | 2003-08-05 | 2005-03-31 | 3M Innovative Properties Company | Infection prophylaxis using immune response modifier compounds |
| AU2004266658A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| PL1653959T3 (pl) | 2003-08-14 | 2015-10-30 | 3M Innovative Properties Co | Modyfikatory odpowiedzi immunologicznej modyfikowane lipidami |
| JP2007503268A (ja) | 2003-08-25 | 2007-02-22 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答修飾化合物の送達 |
| AU2004266162A1 (en) | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| US7897597B2 (en) | 2003-08-27 | 2011-03-01 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004268665A1 (en) | 2003-09-02 | 2005-03-10 | 3M Innovative Properties Company | Methods related to the treatment of mucosal associated conditions |
| JP2007504269A (ja) | 2003-09-05 | 2007-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | Ｃｄ５＋ｂ細胞リンパ腫の治療方法 |
| WO2005025583A2 (en) | 2003-09-05 | 2005-03-24 | Anadys Pharmaceuticals, Inc. | Tlr7 ligands for the treatment of hepatitis c |
| GB0321615D0 (en) | 2003-09-15 | 2003-10-15 | Glaxo Group Ltd | Improvements in vaccination |
| WO2005029037A2 (en) | 2003-09-17 | 2005-03-31 | 3M Innovative Properties Company | Selective modulation of tlr gene expression |
| US7687628B2 (en) | 2003-10-01 | 2010-03-30 | Taro Pharmaceuticals U.S.A., Inc. | Method of preparing 4-amino-1H-imidazo(4,5-c)quinolines and acid addition salts thereof |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| AU2004315876B2 (en) | 2003-10-03 | 2011-05-26 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| US20090075980A1 (en) | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| US20050239733A1 (en) | 2003-10-31 | 2005-10-27 | Coley Pharmaceutical Gmbh | Sequence requirements for inhibitory oligonucleotides |
| WO2005041891A2 (en) | 2003-10-31 | 2005-05-12 | 3M Innovative Properties Company | Neutrophil activation by immune response modifier compounds |
| ITMI20032121A1 (it) | 2003-11-04 | 2005-05-05 | Dinamite Dipharma Spa In Forma Abbr Eviata Dipharm | Procedimento per la preparazione di imiquimod e suoi intermedi |
| AU2004291101A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| EP1682544A4 (en) | 2003-11-14 | 2009-05-06 | 3M Innovative Properties Co | HYDROXYLAMINE SUBSTITUTED IMIDAZO RING COMPOUNDS |
| CU23404A1 (es) | 2003-11-19 | 2009-08-04 | Ct Ingenieria Genetica Biotech | Polisacáridos capsulares de neisseria meningitidis como inmunopotenciadores mucosales y formulaciones resultantes |
| AR046845A1 (es) | 2003-11-21 | 2005-12-28 | Novartis Ag | Derivados de 1h-imidazo[4,5-c]quinolina para tratamiento de enfermedades dependientes de las proteino-quinasas |
| KR20060117329A (ko) | 2003-11-21 | 2006-11-16 | 노파르티스 아게 | 단백질 키나제 저해제로서의 1ｈ-이미다조퀴놀린 유도체 |
| AU2004293078B2 (en) | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| WO2005051324A2 (en) | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| EP1689361A4 (en) | 2003-12-02 | 2009-06-17 | 3M Innovative Properties Co | THERAPEUTIC COMBINATIONS AND PROCESSES WITH IRM COMPOUNDS |
| US20050226878A1 (en) | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| JP2007513170A (ja) | 2003-12-04 | 2007-05-24 | スリーエム イノベイティブ プロパティズ カンパニー | スルホン置換イミダゾ環エーテル |
| EP1701955A1 (en) | 2003-12-29 | 2006-09-20 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| CA2552101A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds |
| EP1699398A4 (en) | 2003-12-30 | 2007-10-17 | 3M Innovative Properties Co | IMPROVING THE IMMUNE RESPONSE |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| WO2005065678A1 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Immunomodulatory combinations |
| US20070167479A1 (en) | 2004-03-15 | 2007-07-19 | Busch Terri F | Immune response modifier formulations and methods |
| EP1730143A2 (en) | 2004-03-24 | 2006-12-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005110013A2 (en) | 2004-04-09 | 2005-11-24 | 3M Innovative Properties Company | Methods, compositions, and preparations for delivery of immune response modifiers |
| EP1755665A4 (en) | 2004-04-28 | 2010-03-03 | 3M Innovative Properties Co | COMPOSITIONS AND METHODS FOR MUCOSAL VACCINATION |
| US20050267145A1 (en) | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
| US20080015184A1 (en) | 2004-06-14 | 2008-01-17 | 3M Innovative Properties Company | Urea Substituted Imidazopyridines, Imidazoquinolines, and Imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006009832A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| EP1765348B1 (en) | 2004-06-18 | 2016-08-03 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006093514A2 (en) | 2004-06-18 | 2006-09-08 | 3M Innovative Properties Company | Aryl and arylalkylenyl substituted thiazoloquinolines and thiazolonaphthyridines |
| US20060045885A1 (en) | 2004-08-27 | 2006-03-02 | Kedl Ross M | Method of eliciting an immune response against HIV |
| WO2006026470A2 (en) | 2004-08-27 | 2006-03-09 | 3M Innovative Properties Company | Hiv immunostimulatory compositions |
| US20060045866A1 (en) * | 2004-09-01 | 2006-03-02 | Chris Chappelow | Novel high purity and high molecular weight mPEG alcohol compositions |
| WO2006026760A2 (en) | 2004-09-02 | 2006-03-09 | 3M Innovative Properties Company | 1-amino imidazo-containing compounds and methods |
| CA2578975A1 (en) | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 2-amino 1h imidazo ring systems and methods |
| WO2006028962A2 (en) | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 1-alkoxy 1h-imidazo ring systems and methods |
| WO2006028451A1 (en) | 2004-09-03 | 2006-03-16 | 3M Innovative Properties Company | 1-amino 1-h-imidazoquinolines |
| US20080193468A1 (en) | 2004-09-08 | 2008-08-14 | Children's Medical Center Corporation | Method for Stimulating the Immune Response of Newborns |
| CN101056877B (zh) | 2004-09-14 | 2010-06-09 | 诺华疫苗和诊断公司 | 咪唑并喹啉化合物 |
| US20070243215A1 (en) | 2004-10-08 | 2007-10-18 | Miller Richard L | Adjuvant for Dna Vaccines |
| JP2008523084A (ja) | 2004-12-08 | 2008-07-03 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫賦活用合剤および方法 |
| WO2006063072A2 (en) | 2004-12-08 | 2006-06-15 | 3M Innovative Properties Company | Immunomodulatory compositions, combinations and methods |
| US8080560B2 (en) | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| ZA200706251B (en) | 2004-12-30 | 2008-11-26 | Coley Pharm Group Inc | Immune response modifier formulations and methods |
| US8034938B2 (en) | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| US20080188513A1 (en) | 2004-12-30 | 2008-08-07 | Taked Pharmaceutical Company Limited | 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Ethanesulfonate and 1-(2-Methylpropyl)-1H-Imidazo[4,5-C](1,5]Naphthyridin-4-Amine Methanesulfonate |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| SI1830876T1 (sl) | 2004-12-30 | 2015-08-31 | Meda Ab | Uporaba imikvimoda za zdravljenje kožnih metastaz, ki izhajajo iz rakavega tumorja dojke |
| 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 |
| CN101160518B (zh) | 2005-02-02 | 2010-08-04 | 膜康公司 | 探测和报告气密包装中泄漏大小的仪器和方法 |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| EP1877056A2 (en) | 2005-02-09 | 2008-01-16 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazoloý4,5-c¨ring compounds and methods |
| CA2597324C (en) | 2005-02-09 | 2015-06-30 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| EP1845988A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Substituted imidazoquinolines and imidazonaphthyridines |
| AU2006213746A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods |
| CA2597595A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Substituted fused [1,2]imidazo[4,5-c] ring compounds and methods |
| WO2006091647A2 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| EP1851220A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| JP2008531567A (ja) | 2005-02-23 | 2008-08-14 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ヒドロキシアルキル置換イミダゾキノリン化合物および方法 |
| EP1851224A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| WO2006099275A2 (en) | 2005-03-14 | 2006-09-21 | 3M Innovative Properties Company | Method of treating actinic keratosis |
| CA2602683A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| AU2006244635A1 (en) | 2005-04-01 | 2006-11-16 | Coley Pharmaceutical Group, Inc. | Ring closing and related methods and intermediates |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| WO2006107771A2 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | PYRAZOLO[3,4-c]QUINOLINES, PYRAZOLO[3,4-c]NAPHTHYRIDINES, ANALOGS THEREOF, AND METHODS |
| EP1874345B1 (en) | 2005-04-25 | 2012-08-15 | 3M Innovative Properties Company | Immunostimulatory compositions |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| CN101253173A (zh) | 2005-09-02 | 2008-08-27 | 辉瑞有限公司 | 羟基取代的1h-咪唑并吡啶和方法 |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| AU2006287270A1 (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 |
| WO2007035935A1 (en) | 2005-09-23 | 2007-03-29 | Coley Pharmaceutical Group, Inc. | METHOD FOR 1H-IMIDAZO[4,5-c]PYRIDINES AND ANALOGS THEREOF |
| EP1948173B1 (en) | 2005-11-04 | 2013-07-17 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods |
| WO2007062043A1 (en) | 2005-11-23 | 2007-05-31 | Coley Pharmaceutical Group Inc. | Method of activating murine toll-like receptor 8 |
| MX2008007864A (es) | 2005-12-16 | 2009-03-04 | Coley Pharm Group Inc | Imidazoquinolinas, imidazonaftiridinas, e imidazopiridinas sustituidas, composiciones y metodos. |
| WO2007079146A1 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc | Treatment for non-hodgkin's lymphoma |
| WO2007079202A2 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute lymhoblastic leukemia |
| WO2007079086A1 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Pyrazoloalkyl substituted imidazo ring compounds and methods |
| JP2009522296A (ja) | 2005-12-28 | 2009-06-11 | スリーエム イノベイティブ プロパティズ カンパニー | 皮膚のｔ細胞リンパ腫の治療 |
| WO2007079171A2 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for hodgkin's lymphoma |
| WO2007079169A2 (en) | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Treatment for acute myeloid leukemia |
| US20090306388A1 (en) | 2006-02-10 | 2009-12-10 | Pfizer Inc. | Method for substituted ih-imidazo[4,5-c] pyridines |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2007106852A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Substituted fused[1,2]imidazo[4,5-c] ring compounds and methods |
| WO2007106854A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods |
| WO2007143526A2 (en) | 2006-06-05 | 2007-12-13 | Coley Pharmaceutical Group, Inc. | Substituted tetrahydroimidazonaphthyridines and methods |
| WO2007149802A2 (en) | 2006-06-19 | 2007-12-27 | 3M Innovative Properties Company | Formulation for delivery of immune response modifiers |
| RU2009102282A (ru) | 2006-06-27 | 2010-08-10 | Шеринг-Плау Хельскер Продактс, Инк. (Us) | Аэрозольные композиции лосьонов |
| 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 |
| WO2008016475A2 (en) | 2006-07-31 | 2008-02-07 | 3M Innovative Properties Company | Immune response modifier compositions and methods |
| US8178539B2 (en) | 2006-09-06 | 2012-05-15 | 3M Innovative Properties Company | Substituted 3,4,6,7-tetrahydro-5H-1,2a,4a,8-tetraazacyclopenta[cd]phenalenes and methods |
| WO2008036312A1 (en) | 2006-09-19 | 2008-03-27 | Coley Pharmaceutical Group, Inc. | Fungicidal methods using immune response modifier compounds |
| WO2008045543A1 (en) | 2006-10-13 | 2008-04-17 | Coley Pharmaceutical Group, Inc. | Substituted 4h-imidazo [4, 5, 1-ij] [1, 6] naphthyridine-9-amines and their pharmaceutical use |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
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2005
- 2005-12-29 AU AU2005322898A patent/AU2005322898B2/en not_active Ceased
- 2005-12-29 EP EP05855766A patent/EP1831226B1/en not_active Not-in-force
- 2005-12-29 WO PCT/US2005/047258 patent/WO2006074003A2/en not_active Ceased
- 2005-12-29 CA CA2592904A patent/CA2592904C/en not_active Expired - Fee Related
- 2005-12-29 JP JP2007549590A patent/JP5543068B2/ja not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2005322898B2 (en) | 2011-11-24 |
| US20080269192A1 (en) | 2008-10-30 |
| US20110207725A1 (en) | 2011-08-25 |
| US8207162B2 (en) | 2012-06-26 |
| EP1831226A4 (en) | 2008-11-05 |
| CA2592904C (en) | 2015-04-07 |
| US7943609B2 (en) | 2011-05-17 |
| CA2592904A1 (en) | 2006-07-13 |
| WO2006074003A2 (en) | 2006-07-13 |
| EP1831226B1 (en) | 2012-08-08 |
| EP1831226A2 (en) | 2007-09-12 |
| WO2006074003A3 (en) | 2007-11-22 |
| JP2008526754A (ja) | 2008-07-24 |
| AU2005322898A1 (en) | 2006-07-13 |
| US8546383B2 (en) | 2013-10-01 |
| US20120232057A1 (en) | 2012-09-13 |
| JP5543068B2 (ja) | 2014-07-09 |
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