US2014328876A1PendingUtilityA1

Synthetic derivatives of mpl and uses thereof

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Assignee: VARIATION BIOTECHNOLOGIES INCPriority: Nov 18, 2011Filed: Nov 16, 2012Published: Nov 6, 2014
Est. expiryNov 18, 2031(~5.3 yrs left)· nominal 20-yr term from priority
A61K 39/099C12N 2760/16034A61K 2039/55555A61K 39/39A61K 39/0275A61K 9/127C07H 13/04A61K 9/19A61K 39/292A61K 39/21C07H 15/12A61K 39/29A61K 39/107C12N 2760/16234A61P 31/12C12N 2760/16134A61K 9/0019C07H 13/06A61K 2039/55572A61K 39/145A61P 37/04A61K 39/12Y02A50/30A61K 39/00
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Claims

Abstract

In one aspect, the present disclosure provides compounds of formulae (I) and (II). In another aspect, a compound of formula (I) or (II) is formulated into compositions with an antigen, optionally with a vesicle. In some embodiments, compositions are administered intramuscularly.

Claims

exact text as granted — not AI-modified
1 . A compound of formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are independently selected from C x  alkyl or C x+1  alkyl; and 
 x is an integer from 6 to 20. 
 
     
     
         2 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are the same. 
     
     
         3 . The compound of  claim 1 , wherein R 1 , R 3 , R 5 , and R 6  are the same. 
     
     
         4 . The compound of  claim 1 , wherein R 2  and R 4  are the same. 
     
     
         5 . The compound of  claim 1 , wherein R 1 , R 3 , R 5 , and R 6  are C x  alkyl, and R 2  and R 4  are C x+1  alkyl. 
     
     
         6 . The compound of  claim 1 , wherein R 1 , R 3 , R 5 , and R 6  are C x+1  alkyl, and R 2  and R 4  are C x  alkyl. 
     
     
         7 . The compound of  claim 1 , wherein x is 6, 7, 8, 9, 10, or 11. 
     
     
         8 . The compound of  claim 1 , wherein x is 6. 
     
     
         9 . The compound of  claim 1 , wherein x is 8. 
     
     
         10 . The compound of  claim 1 , wherein x is 11. 
     
     
         11 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are C 6  alkyl. 
     
     
         12 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are n-hexyl. 
     
     
         13 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are C 8  alkyl. 
     
     
         14 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are n-octyl. 
     
     
         15 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are C n  alkyl. 
     
     
         16 . The compound of  claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are n-undecyl. 
     
     
         17 . A compound of formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1′ , R 3′ , R 5′ , and R 6′  are C y  alkyl; 
 R 2′  and R 4′  are independently C y  alkyl, C y+1  alkyl, or C y+2  alkyl; and 
 y is 6 or 7. 
 
     
     
         18 . The compound of  claim 17 , wherein R 2′  and R 4′  are C y  alkyl. 
     
     
         19 . The compound of  claim 18 , wherein y is 6. 
     
     
         20 . The compound of  claim 17 , wherein R 2′  and R 4′  are C y+1  alkyl. 
     
     
         21 . The compound of  claim 17 , wherein R 2′  and R 4′  are C y+2  alkyl. 
     
     
         22 . The compound of  claim 21 , wherein y is 6. 
     
     
         23 . A composition comprising a compound of  claim 1  and an antigen. 
     
     
         24 . The composition of  claim 23 , wherein the antigen is a virus. 
     
     
         25 . The composition of  claim 24 , wherein the virus is an attenuated virus. 
     
     
         26 . The composition of  claim 24 , wherein the virus is an inactivated virus. 
     
     
         27 . The composition of  claim 24 , wherein the virus is a whole virus. 
     
     
         28 . The composition of  claim 24 , wherein the virus is a split virus. 
     
     
         29 . The composition of  claim 24 , wherein the virus is hepatitis A. 
     
     
         30 . The composition of  claim 24 , wherein the virus is influenza. 
     
     
         31 . The composition of  claim 23 , wherein the antigen is selected from the group consisting of  Bordetella pertussis, Vibrio cholerae  and  Salmonella typhi.    
     
     
         32 . The composition of  claim 23 , wherein the antigen is a polypeptide. 
     
     
         33 . The composition of  claim 32 , wherein the polypeptide is a recombinant polypeptide. 
     
     
         34 . The composition of  claim 32 , wherein the polypeptide is a viral polypeptide. 
     
     
         35 . The composition of  claim 34 , wherein the polypeptide is a hepatitis A polypeptide. 
     
     
         36 . The composition of  claim 34 , wherein the polypeptide is a hepatitis B polypeptide. 
     
     
         37 . The composition of  claim 36 , wherein the polypeptide is HBsAg. 
     
     
         38 . The composition of  claim 34 , wherein the polypeptide is a hepatitis C polypeptide. 
     
     
         39 . The composition of  claim 34 , wherein the polypeptide is an HIV polypeptide. 
     
     
         40 . The composition of  claim 34 , wherein the polypeptide is an influenza polypeptide. 
     
     
         41 . The composition of  claim 40 , wherein the polypeptide is hemagglutinin, neuraminidase, or a combination thereof. 
     
     
         42 . The composition of  claim 23 , wherein the composition comprises a mixture of antigens. 
     
     
         43 . The composition of  claim 42 , wherein the composition comprises a mixture of polypeptides. 
     
     
         44 . The composition of  claim 43 , wherein the mixture of polypeptides comprises a mixture of polypeptides from the same virus. 
     
     
         45 . The composition of  claim 23 , wherein the antigen is a polynucleotide. 
     
     
         46 . The composition of  claim 23 , wherein the antigen is a polysaccharide. 
     
     
         47 . The composition of  claim 23 , wherein the antigen is a virus-like particle. 
     
     
         48 . The composition of  claim 23 , wherein the antigen is a peptide antigen. 
     
     
         49 . The composition of  claim 48 , wherein the peptide antigen includes one or more fragments of an HIV polypeptide. 
     
     
         50 . The composition of  claim 48 , wherein the peptide antigen includes one or more fragments of an influenza polypeptide. 
     
     
         51 . The composition of  claim 23 , further comprising a vesicle which comprises a non-ionic surfactant. 
     
     
         52 . (canceled) 
     
     
         53 . (canceled) 
     
     
         54 . (canceled) 
     
     
         55 . (canceled) 
     
     
         56 . (canceled) 
     
     
         57 . (canceled) 
     
     
         58 . (canceled) 
     
     
         59 . (canceled) 
     
     
         60 . (canceled) 
     
     
         61 . (canceled) 
     
     
         62 . (canceled) 
     
     
         63 . (canceled) 
     
     
         64 . (canceled) 
     
     
         65 . (canceled) 
     
     
         66 . (canceled) 
     
     
         67 . The composition of  claim 51 , wherein the vesicle comprises 1-monopalmitoyl glycerol, dicetylphospate and cholesterol. 
     
     
         68 . A method comprising administering to a patient in need thereof a therapeutically effective amount of the composition of  claim 51 . 
     
     
         69 . The method of  claim 68 , wherein the composition is administered by intramuscular injection.

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