IP Library Granted Patent US 12,201,688
Granted Patent B2
US 12,201,688 · App. 18/059,726 · Granted Jan 21, 2025

Lipidated immune response modifier compound compositions, formulations, and methods

Inventor: Paul D. Wightman (St. Paul, MN)
Assignee: Solventum Intellectual Properties Company
A61K39/39A61K9/0019A61K9/10A61K9/127A61K31/437A61K31/47A61K39/0011A61K39/145A61K47/26C07D471/04C12N7/00A61K2039/54A61K2039/55511A61K2039/55555A61K2039/55572A61K2039/572C12N2760/16134Y02A50/30
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Quick Facts
Patent No.
US 12,201,688
App. No.
18/059,726
Granted
Jan 21, 2025
Kind
B2
Abstract

The compound N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide is a useful drug compound for enhancing immune response and can be used, for example, as a retrovirus vaccine adjuvant.

Claims (11)

1. A pharmaceutical composition comprising:

a compound of formula:

a pharmaceutically acceptable carrier; and

an antigen comprising a retrovirus vaccine.

2. The pharmaceutical composition of claim 1 , wherein the antigen comprises a lentivirus vaccine.

3. The pharmaceutical composition of claim 1 , wherein the antigen comprises a human immunodeficiency virus (HIV) vaccine.

4. A pharmaceutical composition of claim 1 further comprising liposomes.

5. The pharmaceutical composition of claim 1 , wherein the compound and antigen are admixed into a single composition.

6. The pharmaceutical composition of claim 1 , wherein the compound and antigen are present in separate components of the composition to be administered in combination.

7. A method of enhancing the effectiveness of a vaccine antigen by administering as a vaccine adjuvant the compound N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide, or a pharmaceutically acceptable salt thereof.

8. The method of claim 7 wherein the compound is incorporated into a liposome formulation.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066438/0301 →
Continuity (9)
Continuation 16949136 · Oct 15, 2020
Continuation 16504716 · Jul 8, 2019
Division 16043394 · Jul 24, 2018
Continuation 15822556 · Nov 27, 2017
Continuation 15241166 · Aug 19, 2016
Continuation 14969483 · Dec 15, 2015
Division 13817214
Provisional Application 61374512 · Aug 17, 2010
Related Publication 20230090437A1 · Mar 23, 2023
References Cited (302)
US 3314941A · Ruddy et al. · 1967 [cited by applicant]
US 4689338A · Gerster · 1987 [cited by applicant]
US 4698348A · Gerster · 1987 [cited by applicant]
US 4929624A · Gerster et al. · 1990 [cited by applicant]
US 4988815A · Andre et al. · 1991 [cited by applicant]
US 5037986A · Gerster · 1991 [cited by applicant]
US 5175296A · Gerster · 1992 [cited by applicant]
US 5238944A · Schultz et al. · 1993 [cited by applicant]
US 5266575A · Gerster et al. · 1993 [cited by applicant]
US 5268376A · Gester · 1993 [cited by applicant]
US 5346905A · Gerster · 1994 [cited by applicant]
US 5352784A · Nikolaides et al. · 1994 [cited by applicant]
US 5367076A · Gerster · 1994 [cited by applicant]
US 5389640A · Gerster et al. · 1995 [cited by applicant]
US 5395937A · Nikolaides et al. · 1995 [cited by applicant]
US 5444065A · Nikolaides et al. · 1995 [cited by applicant]
US 5446153A · Lindstrom et al. · 1995 [cited by applicant]
US 5482936A · Lindstrom · 1996 [cited by applicant]
US 5494916A · Lindstrom et al. · 1996 [cited by applicant]
US 5525612A · Gerster · 1996 [cited by applicant]
US 5627281A · Nikolaides et al. · 1997 [cited by applicant]
US 5644063A · Lindstrom et al. · 1997 [cited by applicant]
US 5648516A · Nikolaides et al. · 1997 [cited by applicant]
US 5693811A · Lindstrom · 1997 [cited by applicant]
US 5714608A · Gerster · 1998 [cited by applicant]
US 5741908A · Gerster et al. · 1998 [cited by applicant]
US 5756747A · Gerster · 1998 [cited by applicant]
US 5886006A · Nikolaides et al. · 1999 [cited by applicant]
US 5939090A · Beaurline et al. · 1999 [cited by applicant]
US 6039969A · Tomai et al. · 2000 [cited by applicant]
US 6069149A · Nanba et al. · 2000 [cited by applicant]
US 6083505A · Miller et al. · 2000 [cited by applicant]
US 6110929A · Gerster et al. · 2000 [cited by applicant]
US 6194425B1 · Gerster et al. · 2001 [cited by applicant]
US 6200592B1 · Tomai et al. · 2001 [cited by applicant]
US 6245776B1 · Skwierczynski et al. · 2001 [cited by applicant]
US 6331539B1 · Crooks et al. · 2001 [cited by applicant]
US 6365166B2 · Beaurline et al. · 2002 [cited by applicant]
US 6376669B1 · Rice et al. · 2002 [cited by applicant]
US 6440992B1 · Gerster et al. · 2002 [cited by applicant]
US 6451810B1 · Coleman et al. · 2002 [cited by applicant]
US 6486168B1 · Skwierczynski et al. · 2002 [cited by applicant]
US 6514985B1 · Gerster et al. · 2003 [cited by applicant]
US 6518265B1 · Kato et al. · 2003 [cited by applicant]
US 6525064B1 · Dellaria et al. · 2003 [cited by applicant]
US 6541485B1 · Crooks et al. · 2003 [cited by applicant]
US 6545016B1 · Dellaria et al. · 2003 [cited by applicant]
US 6545017B1 · Dellaria et al. · 2003 [cited by applicant]
US 6558951B1 · Tomai et al. · 2003 [cited by applicant]
US 6573273B1 · Crooks et al. · 2003 [cited by applicant]
US 6610319B2 · Tomai et al. · 2003 [cited by applicant]
US 6627638B2 · Gerster et al. · 2003 [cited by applicant]
US 6627640B2 · Gerster et al. · 2003 [cited by applicant]
US 6630588B2 · Rice et al. · 2003 [cited by applicant]
US 6638944B2 · Mickelson · 2003 [cited by applicant]
US 6656938B2 · Crooks et al. · 2003 [cited by applicant]
US 6660735B2 · Crooks et al. · 2003 [cited by applicant]
US 6660747B2 · Crooks et al. · 2003 [cited by applicant]
US 6664260B2 · Charles et al. · 2003 [cited by applicant]
US 6664264B2 · Dellaria et al. · 2003 [cited by applicant]
US 6664265B2 · Crooks et al. · 2003 [cited by applicant]
US 6667312B2 · Bonk et al. · 2003 [cited by applicant]
US 6670372B2 · Charles et al. · 2003 [cited by applicant]
US 6677347B2 · Crooks et al. · 2004 [cited by applicant]
US 6677348B2 · Heppner et al. · 2004 [cited by applicant]
US 6677349B1 · Griesgraber · 2004 [cited by applicant]
US 6683088B2 · Crooks et al. · 2004 [cited by applicant]
US 6696076B2 · Tomai et al. · 2004 [cited by applicant]
US 6696465B2 · Dellaria et al. · 2004 [cited by applicant]
US 6703402B2 · Gerster et al. · 2004 [cited by applicant]
US 6706728B2 · Hedenstrom et al. · 2004 [cited by applicant]
US 6716988B2 · Dellaria et al. · 2004 [cited by applicant]
US 6720333B2 · Dellaria et al. · 2004 [cited by applicant]
US 6720334B2 · Dellaria et al. · 2004 [cited by applicant]
US 6720422B2 · Dellaria et al. · 2004 [cited by applicant]
US 6743920B2 · Lindstrom et al. · 2004 [cited by applicant]
US 6756382B2 · Coleman et al. · 2004 [cited by applicant]
US 6797718B2 · Dellaria et al. · 2004 [cited by applicant]
US 6800624B2 · Crooks et al. · 2004 [cited by applicant]
US 6809203B2 · Gerster et al. · 2004 [cited by applicant]
US 6818650B2 · Griesgraber · 2004 [cited by applicant]
US 6825350B2 · Crooks et al. · 2004 [cited by applicant]
US 6841678B2 · Merli et al. · 2005 [cited by applicant]
US 6852861B2 · Merli et al. · 2005 [cited by applicant]
US 6878719B2 · Lindstrom et al. · 2005 [cited by applicant]
US 6888000B2 · Crooks et al. · 2005 [cited by applicant]
US 6894060B2 · Slade · 2005 [cited by applicant]
US 6897221B2 · Crooks et al. · 2005 [cited by applicant]
US 6903113B2 · Heppner et al. · 2005 [cited by applicant]
US 6916925B1 · Rice et al. · 2005 [cited by applicant]
US 6921826B2 · Dellaria et al. · 2005 [cited by applicant]
US 6924293B2 · Lindstrom · 2005 [cited by applicant]
US 6943225B2 · Lee et al. · 2005 [cited by applicant]
US 6949649B2 · Bonk et al. · 2005 [cited by applicant]
US 6953804B2 · Dellaria et al. · 2005 [cited by applicant]
US 6969722B2 · Heppner et al. · 2005 [cited by applicant]
US 6989389B2 · Heppner et al. · 2006 [cited by applicant]
US 7030129B2 · Miller et al. · 2006 [cited by applicant]
US 7030131B2 · Crooks et al. · 2006 [cited by applicant]
US 7038053B2 · Lindstrom et al. · 2006 [cited by applicant]
US 7049439B2 · Griesgraber · 2006 [cited by applicant]
US 7078523B2 · Griesgraber · 2006 [cited by applicant]
US 7091214B2 · Hays et al. · 2006 [cited by applicant]
US 7098221B2 · Heppner et al. · 2006 [cited by applicant]
US 7112677B2 · Griesgraber · 2006 [cited by applicant]
US 7115622B2 · Crooks et al. · 2006 [cited by applicant]
US 7125890B2 · Dellaria et al. · 2006 [cited by applicant]
US 7132429B2 · Griesgraber et al. · 2006 [cited by applicant]
US 7132438B2 · Frenkel et al. · 2006 [cited by applicant]
US 7148232B2 · Gerster et al. · 2006 [cited by applicant]
US 7157453B2 · Crooks et al. · 2007 [cited by applicant]
US 7163947B2 · Griesgraber et al. · 2007 [cited by applicant]
US 7179253B2 · Graham et al. · 2007 [cited by applicant]
US 7199131B2 · Lindstrom · 2007 [cited by applicant]
US 7214675B2 · Griesgraber · 2007 [cited by applicant]
US 7220758B2 · Dellaria et al. · 2007 [cited by applicant]
US 7226928B2 · Mitra et al. · 2007 [cited by applicant]
US 7276515B2 · Dellaria et al. · 2007 [cited by applicant]
US 7288550B2 · Dellaria et al. · 2007 [cited by applicant]
US 7301027B2 · Colombo et al. · 2007 [cited by applicant]
US 7375180B2 · Gorden et al. · 2008 [cited by applicant]
US 7387271B2 · Noelle et al. · 2008 [cited by applicant]
US 7393859B2 · Coleman et al. · 2008 [cited by applicant]
US 7427629B2 · Kedl et al. · 2008 [cited by applicant]
US 7485432B2 · Fink et al. · 2009 [cited by applicant]
US 7544697B2 · Hays et al. · 2009 [cited by applicant]
US 7576068B2 · Averett · 2009 [cited by applicant]
US 7578170B2 · Mayer et al. · 2009 [cited by applicant]
US 7579359B2 · Krepski et al. · 2009 [cited by applicant]
US 7598382B2 · Hays et al. · 2009 [cited by applicant]
US 7612083B2 · Griesgraber · 2009 [cited by applicant]
US 7648997B2 · Kshirsagar et al. · 2010 [cited by applicant]
US 7655672B2 · Statham et al. · 2010 [cited by applicant]
US 7687628B2 · Gutman et al. · 2010 [cited by applicant]
US 7696159B2 · Owens et al. · 2010 [cited by applicant]
US 7699057B2 · Miller et al. · 2010 [cited by applicant]
US 7731967B2 · O'Hagan et al. · 2010 [cited by applicant]
US 7799800B2 · Wightman · 2010 [cited by applicant]
US 7879849B2 · Hays et al. · 2011 [cited by applicant]
US 7884207B2 · Stoermer et al. · 2011 [cited by applicant]
US 7888349B2 · Kshirsagar et al. · 2011 [cited by applicant]
US 7897597B2 · Lindstrom et al. · 2011 [cited by applicant]
US 7897609B2 · Niwas et al. · 2011 [cited by applicant]
US 7897767B2 · Kshirsagar et al. · 2011 [cited by applicant]
US 7902209B2 · Statham et al. · 2011 [cited by applicant]
US 7902210B2 · Statham et al. · 2011 [cited by applicant]
US 7902211B2 · Statham et al. · 2011 [cited by applicant]
US 7902212B2 · Statham et al. · 2011 [cited by applicant]
US 7902213B2 · Statham et al. · 2011 [cited by applicant]
US 7902214B2 · Statham et al. · 2011 [cited by applicant]
US 7902215B2 · Statham et al. · 2011 [cited by applicant]
US 7902216B2 · Statham et al. · 2011 [cited by applicant]
US 7902242B2 · Statham et al. · 2011 [cited by applicant]
US 7902243B2 · Statham et al. · 2011 [cited by applicant]
US 7902244B2 · Statham et al. · 2011 [cited by applicant]
US 7902245B2 · Statham et al. · 2011 [cited by applicant]
US 7902246B2 · Statham et al. · 2011 [cited by applicant]
US 7906506B2 · Griesgraber et al. · 2011 [cited by applicant]
US 7915281B2 · Moser et al. · 2011 [cited by applicant]
US 7939526B2 · Radmer et al. · 2011 [cited by applicant]
US 7943609B2 · Griesgraber et al. · 2011 [cited by applicant]
US 7968562B2 · Skwierczynski et al. · 2011 [cited by applicant]
US 7968563B2 · Kshirsagar et al. · 2011 [cited by applicant]
US 7993659B2 · Noelle et al. · 2011 [cited by applicant]
US 8017779B2 · Merrill et al. · 2011 [cited by applicant]
US 8026366B2 · Prince et al. · 2011 [cited by applicant]
US 8034938B2 · Griesgraber et al. · 2011 [cited by applicant]
US 9242980B2 · Wightman · 2016 [cited by applicant]
US 20020055517A1 · Smith · 2002 [cited by applicant]
US 20020058674A1 · Hedenstrom et al. · 2002 [cited by applicant]
US 20020107262A1 · Lindstrom · 2002 [cited by applicant]
US 20030133913A1 · Tomai et al. · 2003 [cited by applicant]
US 20030139364A1 · Krieg et al. · 2003 [cited by applicant]
US 20040014779A1 · Gorden et al. · 2004 [cited by applicant]
US 20040132079A1 · Gupta et al. · 2004 [cited by applicant]
US 20040175336A1 · Egging et al. · 2004 [cited by applicant]
US 20040180919A1 · Miller et al. · 2004 [cited by applicant]
US 20040191833A1 · Fink et al. · 2004 [cited by applicant]
US 20040197865A1 · Gupta et al. · 2004 [cited by applicant]
US 20040202720A1 · Wightman et al. · 2004 [cited by applicant]
US 20040214851A1 · Birmachu et al. · 2004 [cited by applicant]
US 20040258698A1 · Wightman et al. · 2004 [cited by applicant]
US 20040265351A1 · Miller et al. · 2004 [cited by applicant]
US 20050048072A1 · Kedl et al. · 2005 [cited by applicant]
US 20050059072A1 · Birmachu et al. · 2005 [cited by applicant]
US 20050070460A1 · Hammerbeck et al. · 2005 [cited by applicant]
US 20050096259A1 · Tomai et al. · 2005 [cited by applicant]
US 20050106300A1 · Chen et al. · 2005 [cited by applicant]
US 20050158325A1 · Hammerbeck et al. · 2005 [cited by applicant]
US 20050165043A1 · Miller et al. · 2005 [cited by applicant]
US 20050171072A1 · Tomai et al. · 2005 [cited by applicant]
US 20050239735A1 · Miller et al. · 2005 [cited by applicant]
US 20050245562A1 · Garcia-Echeverria et al. · 2005 [cited by applicant]
US 20060045885A1 · Kedl et al. · 2006 [cited by applicant]
US 20060045886A1 · Kedl · 2006 [cited by applicant]
US 20060051374A1 · Miller et al. · 2006 [cited by applicant]
US 20060088542A1 · Braun · 2006 [cited by applicant]
US 20060142202A1 · Alkan et al. · 2006 [cited by applicant]
US 20060142235A1 · Miller et al. · 2006 [cited by applicant]
US 20060171962A1 · Enjuanes et al. · 2006 [cited by applicant]
US 20060195067A1 · Wolter et al. · 2006 [cited by applicant]
US 20060216333A1 · Miller et al. · 2006 [cited by applicant]
US 20070060754A1 · Lindstrom et al. · 2007 [cited by applicant]
US 20070066639A1 · Kshirsagar et al. · 2007 [cited by applicant]
US 20070072893A1 · Krepski et al. · 2007 [cited by applicant]
US 20070099901A1 · Krepski et al. · 2007 [cited by applicant]
US 20070123559A1 · Statham et al. · 2007 [cited by applicant]
US 20070166384A1 · Zarraga · 2007 [cited by applicant]
US 20070167479A1 · Busch et al. · 2007 [cited by applicant]
US 20070213355A1 · Capraro et al. · 2007 [cited by applicant]
US 20070219196A1 · Krepski et al. · 2007 [cited by applicant]
US 20070243215A1 · Miller et al. · 2007 [cited by applicant]
US 20070259881A1 · Dellaria, Jr. et al. · 2007 [cited by applicant]
US 20070259907A1 · Prince · 2007 [cited by applicant]
US 20070292456A1 · Hammerbeck et al. · 2007 [cited by applicant]
US 20080015184A1 · Kshirsagar et al. · 2008 [cited by applicant]
US 20080039533A1 · Sahouani et al. · 2008 [cited by applicant]
US 20080063714A1 · Sahouani et al. · 2008 [cited by applicant]
US 20080119508A1 · Slade et al. · 2008 [cited by applicant]
US 20080188513A1 · Skwierczynski et al. · 2008 [cited by applicant]
US 20080193468A1 · Levy et al. · 2008 [cited by applicant]
US 20080193474A1 · Griesgraber et al. · 2008 [cited by applicant]
US 20080207674A1 · Stoesz et al. · 2008 [cited by applicant]
US 20080213308A1 · Valiante et al. · 2008 [cited by applicant]
US 20080262021A1 · Capraro et al. · 2008 [cited by applicant]
US 20080262022A1 · Lee et al. · 2008 [cited by applicant]
US 20080306252A1 · Crooks et al. · 2008 [cited by applicant]
US 20080306266A1 · Martin et al. · 2008 [cited by applicant]
US 20080312434A1 · Lindstrom et al. · 2008 [cited by applicant]
US 20080318998A1 · Prince et al. · 2008 [cited by applicant]
US 20090005371A1 · Rice et al. · 2009 [cited by applicant]
US 20090005376A1 · Krepski et al. · 2009 [cited by applicant]
US 20090017076A1 · Miller et al. · 2009 [cited by applicant]
US 20090023720A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090023722A1 · Coleman et al. · 2009 [cited by applicant]
US 20090029988A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090030030A1 · Bonk et al. · 2009 [cited by applicant]
US 20090030031A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090035323A1 · Stoermer et al. · 2009 [cited by applicant]
US 20090062272A1 · Bonk et al. · 2009 [cited by applicant]
US 20090069299A1 · Merrill et al. · 2009 [cited by applicant]
US 20090069314A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090075980A1 · Hays et al. · 2009 [cited by applicant]
US 20090099161A1 · Rice et al. · 2009 [cited by applicant]
US 20090105295A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090124611A1 · Hays et al. · 2009 [cited by applicant]
US 20090124652A1 · Ach et al. · 2009 [cited by applicant]
US 20090163532A1 · Ma et al. · 2009 [cited by applicant]
US 20090163533A1 · Hays et al. · 2009 [cited by applicant]
US 20090176821A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090202443A1 · Miller et al. · 2009 [cited by applicant]
US 20090221551A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090221556A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090240055A1 · Krepski et al. · 2009 [cited by applicant]
US 20090246174A1 · Rook et al. · 2009 [cited by applicant]
US 20090253695A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090270443A1 · Stoermer et al. · 2009 [cited by applicant]
US 20090298821A1 · Kshirsagar et al. · 2009 [cited by applicant]
US 20090306388A1 · Zimmerman et al. · 2009 [cited by applicant]
US 20100028381A1 · Gorski et al. · 2010 [cited by applicant]
US 20100056557A1 · Benninghoff et al. · 2010 [cited by applicant]
US 20100096287A1 · Stoesz et al. · 2010 [cited by applicant]
US 20100113565A1 · Gorden et al. · 2010 [cited by applicant]
US 20100152230A1 · Dellaria, Jr. et al. · 2010 [cited by applicant]
US 20100158928A1 · Stoermer et al. · 2010 [cited by applicant]
US 20100173906A1 · Griesgraber · 2010 [cited by applicant]
US 20100180902A1 · Miller et al. · 2010 [cited by applicant]
US 20100240693A1 · Lundquist, Jr. et al. · 2010 [cited by applicant]
US 20110021554A1 · Stoesz et al. · 2011 [cited by applicant]
US 20160175433A1 · Wightman · 2016 [cited by applicant]
EP 0394026B1 · 1993 [cited by applicant]
EP 1104764A1 · 2001 [cited by applicant]
JP 60123488A · 1985 [cited by applicant]
JP 09176116A · 1997 [cited by applicant]
JP 09208584A · 1997 [cited by applicant]
JP 1180156A · 1999 [cited by applicant]
JP 11222432A · 1999 [cited by applicant]
JP 2000247884A · 2000 [cited by applicant]
WO 2002036592A1 · 2002 [cited by applicant]
WO 2004032829A2 · 2004 [cited by applicant]
WO 2005003064A2 · 2005 [cited by applicant]
WO 2005018555A2 · 2005 [cited by applicant]
WO 2005051317A2 · 2005 [cited by applicant]
WO 2006028451A1 · 2006 [cited by applicant]
WO 2006028962A2 · 2006 [cited by applicant]
WO 2006063072A2 · 2006 [cited by applicant]
WO 2006121528A2 · 2006 [cited by applicant]
WO 2007030775A2 · 2007 [cited by applicant]
WO 2012167081A1 · 2012 [cited by applicant]
Bachman, “Synthesis of Substituted Quinolylamines. Derivatives of 4-Amino-7-Chloroquinoline.”, The Journal of Organic Chemistry, vol. 15. 1950, pp. 1278-1284. [cited by applicant]
Baranov, “Pyrazoles, Imidazoles, and Other 5-Membered Rings”, Chemical Abstract, vol. 85, 1976, 94362. [cited by applicant]
Berényi, “Ring Transformation of Condensed Dihydro-as-Triazines”, Journal of Heterocyclic Chemistry, vol. 18, No. 8, 1981, pp. 1537-1540. [cited by applicant]
Brennan, Automated Bioassay of Interferons in Micro-test Plates., Biotechniques. Jun.Jul., 78, 1983. [cited by applicant]
Chollet, “Development of a Topically Active Imiquimod Formulation”, Pharmaceutical Development and Technology, vol. 4, No. 1, 1999, pp. 35-43. [cited by applicant]
Gerster, “Synthesis and Structure-Activity-Relationships of 1 H -Imidazo[4,5- c ]quinolines That Induce Interferon Production”, Journal of Medicinal Chemistry, vol. 48, No. 10, 2005, pp. 3481-3491. [cited by applicant]
International Search Report for PCT Application No. PCT/US2011/047901, mailed on PCTUS2011047901, 9 pages. [cited by applicant]
Izumi, “1H-Imidazo[4,5-c]quinoline Derivatives as Novel Potent TNF-α Suppressors: Synthesis and Structure-Activity Relationship of 1-, 2-and 4-Substituted 1H-imidazo[4,5-c]quinolines or 1H-imidazo[4,5-c]pyridines”y, Bio… [cited by applicant]
Jain, “Chemical and Pharmacological Investigations of some. Omega.-Substituted Alkylamino-3-Aminopyridines”, Journal of Medicinal Chemistry, vol. 11, No. 1, 1968, pp. 87-92. [cited by applicant]
Ruyun, Dictionary of Pharmacy, Shanghai Science and Technology Press, 2006 pp. 1093-1094. [cited by applicant]
Smirnov, “Vaccine Adjuvant Activity of 3M-052: An Imidazoquinoline Designed for Local Activity without Systemic Cytokine Induction”, Vaccine, vol. 29, No. 33, Jul. 26, 2011, pp. 5434-5442. [cited by applicant]
Testerman, “Cytokine induction by the Immunomodulators Imiquimod and S-27609.”, Journal of Leukocyte Biology. vol. 58, Sep. 1995, pp. 365-372. [cited by applicant]
Wozniak et al., “The Amination of 3-nitro-1, 5-naphthyridines by Liquid AmmoniaPotassium Permanganate12. A New and Convenient Amination Method.”, Journal of the Roval Netherlands Chemical Society, vol. 102, Dec. 12, 198… [cited by applicant]