US2004253206A1PendingUtilityA1

Drug-oligomer conjugates

Priority: Sep 13, 1999Filed: Mar 29, 2004Published: Dec 16, 2004
Est. expirySep 13, 2019(expired)· nominal 20-yr term from priority
A61P 35/00A61P 43/00A61P 35/04A61P 35/02A61K 47/50A61K 47/60
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Claims

Abstract

Drug-oligomer conjugates and pharmaceutical compositions prepared therefrom. Methods of making and using the drug-oligomer conjugates and pharmaceutical compositions.

Claims

exact text as granted — not AI-modified
We claim:  
     
         1 . A conjugate comprising: 
 (a) at least one therapeutic compound; and    (b) one or more PEG polymers and/or oligomers, each joined to a bonding site on the therapeutic compound by a hydrolyzable bond, said PEG polymers and/or oligomers each: 
 (i) comprising a straight or branched PEG segment consisting of 1 to 25 polyethylene glycol units; and  
 (ii) comprising a salt-forming moiety.  
   
     
     
         2 . The conjugate of  claim 1 , wherein the conjugate is a prodrug.  
     
     
         3 . The conjugate of  claim 1 , wherein the straight or branched PEG segment consists of from 2 to 20 polyethylene glycol units.  
     
     
         4 . The conjugate of  claim 1 , wherein the polyethylene glycol oligomer has a number of polyethylene glycol units selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, and 9.  
     
     
         5 . The conjugate of  claim 1 , wherein the salt-forming moiety is selected from the group consisting of: ammonium, carboxylate, phosphate, sulfate and mesylate.  
     
     
         6 . The conjugate of  claim 1 , wherein the therapeutic compound is derivatized by from 1 up to the maximum number of sites of attachment for the polyethylene glycol oligomer(s).  
     
     
         7 . The conjugate of  claim 1 , which, when delivered via the oral route of administration to treat a mammalian subject having a disease condition responsive to the therapeutic compound, provides a therapeutically effective dose of the therapeutic compound to the blood.  
     
     
         8 . The conjugate of  claim 1 , wherein the therapeutic compound is a peptide.  
     
     
         9 . The conjugate of  claim 1 , wherein the therapeutic compound is a protein.  
     
     
         10 . A pharmaceutical composition comprising: 
 (a) a conjugate of  claim 1;  and    (b) a pharmaceutically acceptable carrier.    
     
     
         11 . The pharmaceutical composition of  claim 10 , wherein the conjugate is a prodrug.  
     
     
         12 . The pharmaceutical composition of  claim 10  in a form suitable for oral administration.  
     
     
         13 . A conjugate comprising a therapeutic compound joined by hydrolysable bond(s) to one or more PEG oligomer(s) selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 7, m is from 2 to 25, and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25, and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, m and r are each independently from 2 to 25, and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25 and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25, R is hydrogen or lower alkyl, and X −  is a negative ion;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25, and R 1  and R 2  are each independently hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8 and m is from 2 to 25;  
       
         
           
           
               
               
           
         
       
       wherein n and p are each independently from 1 to 6, m is from 2 to 25 and X 30   is a positive ion;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 5, m is from 2 to 25, X −  is a negative ion, and wherein R 1  and R 2  are each independently hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, m is from 2 to 25 and X −  is a negative ion; and  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 12, m is from 2 to 25, p is from 2 to 12, X 30   is a positive ion and Z −  is a negative ion.  
     
     
         14 . The conjugate of  claim 13 , wherein the conjugate is a prodrug.  
     
     
         15 . The conjugate of  claim 13 , wherein the therapeutic compound is derivatized by from 1 up to the maximum number of sites of attachment for the polyethylene glycol oligomer(s).  
     
     
         16 . The conjugate of  claim 13 , wherein the therapeutic compound is a peptide.  
     
     
         17 . The conjugate of  claim 13 , wherein the therapeutic compound is a protein.  
     
     
         18 . A pharmaceutical composition comprising: 
 (a) a conjugate of  claim 13;  and    (b) a pharmaceutically acceptable carrier.    
     
     
         19 . The pharmaceutical composition of  claim 18 , wherein the conjugate is a prodrug.  
     
     
         20 . The pharmaceutical composition of  claim 18  in a form suitable for oral administration.  
     
     
         21 . A method of treating a mammalian subject having a disease condition responsive to a therapeutic compound, said method comprising administering to the subject of an effective disease treating amount of a conjugate comprising: 
 (a) at least one therapeutic compound; and    (b) one or more PEG polymers and/or oligomers, each joined to a bonding site on the therapeutic compound by a hydrolyzable bond, said PEG polymers and/or oligomers each: 
 (i) comprising a straight or branched PEG segment consisting of 1 to 25 polyethylene glycol units; and  
 (ii) comprising a salt-forming moiety.  
   
     
     
         22 . The method of  claim 21 , wherein the conjugate is a prodrug.  
     
     
         23 . The conjugate of  claim 21 , wherein the therapeutic compound is a peptide.  
     
     
         24 . The conjugate of  claim 21 , wherein the therapeutic compound is a protein.  
     
     
         25 . A method of treating a mammalian subject having a disease condition responsive to a therapeutic compound, said method comprising administering to the subject of an effective disease treating amount of a conjugate comprising the therapeutic compound joined by hydrolyzable bond(s) to one or more PEG oligomer(s) selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 7, m is from 2 to 25, and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25, and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, m and r are each independently from 2 to 25, and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25 and R is hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25, R is hydrogen or lower alkyl, and X −  is a negative ion;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8, m is from 2 to 25, and R 1  and R 2  are each independently hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, p is from 2 to 8 and m is from 2 to 25;  
       
         
           
           
               
               
           
         
       
       wherein n and p are each independently from 1 to 6, m is from 2 to 25 and X 30   is a positive ion;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 5, m is from 2 to 25, X −  is a negative ion, and wherein R 1  and R 2  are each independently hydrogen or lower alkyl;  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 6, m is from 2 to 25 and X −  is a negative ion; and  
       
         
           
           
               
               
           
         
       
       wherein n is from 1 to 12, m is from 2 to 25, p is from 2 to 12, X 30   is a positive ion and Z −  is a negative ion.  
     
     
         26 . The method of  claim 25 , wherein the conjugate is a prodrug.  
     
     
         27 . The conjugate of  claim 25 , wherein the therapeutic compound is a peptide.  
     
     
         28 . The conjugate of  claim 25 , wherein the therapeutic compound is a protein.

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