P
USRE49233EActiveUtilityPatentIndex 84

Ionizable cationic lipid for RNA delivery

Assignee: ARCTURUS THERAPEUTICS INCPriority: Nov 18, 2013Filed: Mar 12, 2019Granted: Oct 4, 2022
Est. expiryNov 18, 2033(~7.4 yrs left)· nominal 20-yr term from priority
Inventors:PAYNE JOSEPH ECHIVUKULA PADMANABH
C07J 41/0055C07C 333/04C07C 323/25C12N 2320/32C07C 323/60C12N 15/111C07C 323/52C12N 2310/14C11C 3/04A61P 35/00C07C 235/12C07C 237/12A61P 29/00C07C 271/22A61K 47/20C12N 15/1137A61K 47/18C12N 15/113
84
PatentIndex Score
2
Cited by
39
References
25
Claims

Abstract

What is described is a compound of formula (1)whereinR1 and R2 are the same or different, each a linear or branched alkyl with 1-9 carbons, or an alkenyl or alkynyl with 2 to 11 carbon atoms;L1 and L2 are the same or different, each a linear alkyl having 5 to 18 carbon atoms, or form a heterocycle with N;X1 is a bond, or is —CO—O— whereby L2-CO—O—R2 is formed;X2 is S or O; L3 is a bond or a lower alkyl, or form a heterocycle with N;R3 is a lower alkyl; and R4 and R5 are the same or different, each a lower alkyl;or a pharmaceutically acceptable salt thereof.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound of formula: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  and R 2  are the same or different and each a linear or branched alkyl consisting of 1 to 9 carbons, are an alkenyl or alkynyl consisting, of 2 to 11 carbons, or cholesteryl, 
 L 1  and L 2  are the same or different, each a linear al b lone or alkenylene consisting of 5 to 18 carbons, 
 X 1  is —CO—O— whereby -L 2 -CO—O—R 2  is formed, 
 X 2  is S or O, 
 X 3  is —CO—O— whereby -L 1 -CO—O—R 1  is formed, 
 
       L 3  is a bond,
 R 3    3  is a linear or branched alkylene consisting of 1 to 6 carbons, and 
 R 4  and R 5  are the same or different, each hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
       2. The compound of  claim 1 , wherein the X 2  is S. 
     
     
       3. The compound of  claim 1 , wherein the R 3  is ethylene. 
     
     
       4. The compound of  claim 1 , wherein the R 3  is n-propylene or isobutylene. 
     
     
       5. The compound of  claim 1 , wherein the R 4  and R 5  are separately methyl, ethyl, or isopropyl. 
     
     
       6. The compound of  claim 1 , wherein L 1  and L 2  are the same. 
     
     
       7. The compound of  claim 1 , wherein L 1  and L 2  differ. 
     
     
       8. The compound of  claim 1 , wherein L 1  or L 2  consists of a linear alkylene having seven carbons. 
     
     
       9. The compound of  claim 1 , wherein L 1  or L 2  consists of a linear alkylene having nine carbons. 
     
     
       10. The compound of  claim 1 , wherein R 1  and R 2  are the same. 
     
     
       11. The compound of  claim 1 , wherein R 1  and R 2  differ. 
     
     
       12. The compound of  claim 10 , wherein R 1  and R 2  each consists of an alkenyl. 
     
     
       13. The compound of  claim 10 , wherein R 1  and R 2  each consists of an alkyl. 
     
     
       14. The compound of claim  12  1, wherein the alkenyl of R 1 and R 2  consists of a single double bond. 
     
     
       15. The compound of claim  10  1, wherein R1 R 1  or R2 R 2  consists of nine carbons. 
     
     
       16. The compound of claim  10  1, wherein R1 R 1  or R2 R 2  consists of eleven carbons. 
     
     
       17. The compound of claim  10  1, wherein R1 R 1  or R2 R 2  consists of seven carbons. 
     
     
       18. The compound of  claim 1 , wherein L 3  is a bond, R 3  is ethylene, X 2  is S, and R 4  and R 5  are each methyl. 
     
     
       19. The compound of  claim 1 , wherein L 3  is a bond, R 3  is n-propylene, X 2  is S, R 4  and R 5  are each methyl. 
     
     
       20. The compound of  claim 1 , wherein L 3  is a bond, R 3  is ethylene, X 2  is S, and R 4  and R 5  are each ethyl. 
     
     
       21. The A compound of  claim 1 , selected from the group consisting of the compounds of formula ATX-001 to ATX-028, and ATX-031 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
       22. A compound of formula I 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  and R 2  are the same or different, each a linear or branched alkyl consisting of 1 to 9 carbons, an alkenyl or alkynyl consisting of 2 to 11 carbons, or cholesteryl, 
 L 1  and L 2  are the same or different, each a linear alkylene or alkenylene consisting of 3 or 4 carbons, 
 X 1  is —CO—O— whereby -L 2 -CO—O—R 2  is formed, 
 X 2  is S or O, 
 X 3  is —CO—O— whereby -L 1 -CO—O—R 1  is formed, 
 L 3  is a bond, 
 R 3  is a linear or branched alkylene consisting of 1 to 6 carbons, and R 4  and R 5  are the same or different, each hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
       23. The compound of  claim 22  consisting of the compound of formula ATX-029 
       
         
           
           
               
               
           
         
       
       
        
       
     
     
       24. The compound of claim 21, wherein the compound is 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof.  
     
     
       25. The compound of claim 21, wherein the compound is 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof.

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