US2021024581A1PendingUtilityA1

Conjugates containing hydrophilic spacer linkers

69
Assignee: ENDOCYTE INCPriority: Jun 25, 2007Filed: Jul 2, 2020Published: Jan 28, 2021
Est. expiryJun 25, 2027(~1 yrs left)· nominal 20-yr term from priority
A61K 47/545C07H 15/24A61K 47/65A61P 35/00C07K 9/003A61K 47/60A61P 35/02A61P 31/04A61P 31/10A61P 33/02A61P 33/10A61P 31/00A61P 33/04A61P 33/00A61P 31/12
69
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Claims

Abstract

Described herein are compositions and methods for use in targeted drug delivery using cell receptor binding drug delivery conjugates containing hydrophilic spacer linkers for use in imaging, diagnosing, and/or treating diseases and disease states caused by pathogenic cell populations.

Claims

exact text as granted — not AI-modified
1 .- 39 . (canceled) 
     
     
         40 . A compound of the formula
   B-L-A   wherein
 B is of the formula 
   
       
         
           
           
               
               
           
         
         wherein ** represents a covalent bond to L;
 L is a releasable linker comprising a first hydrophilic spacer linker portion is of the formula 
 
       
       
         
           
           
               
               
           
         
         wherein R is H, alkyl, cycloalkyl, or arylalkyl; m is an independently selected integer from 1 to 3; n is an integer from 1 to 6, p is an integer from 1 to 5, ** represents a covalent bond to B; and 
         * represents a covalent bond a first spacer linker portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein * represents a covalent bond to the first hydrophilic spacer linker portion, and *** represents a covalent bond to a second hydrophilic spacer linker portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein R is H, alkyl, cycloalkyl, or arylalkyl; m is an integer from 1 to 3; n is an integer from 1 to 6, p is an integer from 1 to 5, *** represents a covalent bond to the first spacer linker portion, and * represents a covalent bond to a second spacer linker portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein * represents a covalent bond to the second hydrophilic spacer linker portion, and **** represents a covalent bond to an additional hydrophilic spacer linker portion or an additional spacer linker portion; and a releasable disulfide portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein ** represents a covalent bond to in the additional hydrophilic spacer linker portion or the additional spacer linker portion, and * represents a covalent bond to the rest of the compound; and
 A is therapeutic agent selected from the group consisting of DAVLBH, bortezomib, thiobortezomib, a tubulysin, aminopterin, rapamycin, paclitaxel, docetaxel, doxorubicin, daunorubicin, everolimus, α-amanatin, verucarin, didemnin B, geldanomycin, purvalanol A, everolimus, ispinesib, budesonide, and dasatinib. 
 
       
     
     
         41 . The compound of  claim 40 , wherein p in the first hydrophilic spacer linker portion is 1. 
     
     
         42 . The compound of  claim 41 , wherein p in the second hydrophilic spacer linker portion is 1. 
     
     
         43 . The compound of  claim 42 , wherein m in the first hydrophilic spacer linker portion is 2. 
     
     
         44 . The compound of  claim 43 , wherein m in the second hydrophilic spacer linker portion is 2. 
     
     
         45 . The compound of  claim 44 , wherein n in the first hydrophilic spacer linker portion, when present, is 5. 
     
     
         46 . The compound of  claim 45 , wherein n in the second hydrophilic spacer linker portion, when present, is 5. 
     
     
         47 . The compound of  claim 46 , wherein R in the first hydrophilic spacer linker portion, when present, is H. 
     
     
         48 . The compound of  claim 47 , wherein R in the second hydrophilic spacer linker portion, when present, is H. 
     
     
         49 . The compound of  claim 48 , wherein A is DAVLBH. 
     
     
         50 . The compound of  claim 48 , wherein A is a tubulysin. 
     
     
         51 . A compound of the formula
   B-L-A   wherein
 B is of the formula 
   
       
         
           
           
               
               
           
         
         
           wherein ** represents a covalent bond to L; 
           L is a releasable linker comprising a first hydrophilic spacer linker portion is of the formula 
         
       
       
         
           
           
               
               
           
         
         wherein R is H; m is 2; n is 5, p is 1, ** represents a covalent bond to B; and * represents a covalent bond a first spacer linker portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein * represents a covalent bond to the first hydrophilic spacer linker portion, and *** represents a covalent bond to a second hydrophilic spacer linker portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein R is H; m is 2; n is 5, p is 1, *** represents a covalent bond to the first spacer linker portion, and * represents a covalent bond to a second spacer linker portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein * represents a covalent bond to the second hydrophilic spacer linker portion, and **** represents a covalent bond to an additional hydrophilic spacer linker portion or an additional spacer linker portion; and a releasable-disulfide portion of the formula 
       
       
         
           
           
               
               
           
         
         wherein ** represents a covalent bond to in the additional hydrophilic spacer linker portion or the additional spacer linker portion, and * represents a covalent bond to the rest of the compound; and
 A is an anti-inflammatory agent. 
 
       
     
     
         52 . A pharmaceutical composition comprising (a) an effective amount of a compound of  claim 40 , and optionally one or more of a carrier, a diluent, or an excipient. 
     
     
         53 . A pharmaceutical composition comprising (a) an effective amount of a compound of  claim 48 , and optionally one or more of a carrier, a diluent, or an excipient. 
     
     
         54 . A pharmaceutical composition comprising (a) an effective amount of a compound of  claim 51 , and optionally one or more of a carrier, a diluent, or an excipient. 
     
     
         55 . A method for treating a disease in a patient comprising administering an effective amount of the compound of  claim 40  to the patient. 
     
     
         56 . The method of  claim 55 , wherein the disease is inflammation. 
     
     
         57 . A method for treating a disease in a patient comprising administering an effective amount of the compound of  claim 48  to the patient. 
     
     
         58 . The method of  claim 57 , wherein the disease is inflammation. 
     
     
         59 . A method for treating inflammation in a patient comprising administering an effective amount of the compound of  claim 51  to the patient.

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