Difunctionalized aromatic compounds and polymers therefrom

Abstract

The present invention relates to compounds of formula I, which are difunctionalized aromatic compounds, and polymers formed from the same. [R′—(X) a —OC(O)] p —Ar—[NR′—(Y) b —R′] q   I Polymers formed from the difunctionalized aromatics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.

1 . A compound of formula I or a pharmaceutically acceptable salt thereof:
   [R′—(X) a —OC(O)] p —Ar—[NR′—(Y) b —R′] q   I
   wherein:   Ar is an aromatic ring substituted with 1, 2, or 3 R groups;   X is independently at each occurrence selected from: —CH 2 COO—; —CH(CH 3 )COO—; —CH 2 CH 2 OCH 2 COO—; —CH 2 CH 2 CH 2 CH 2 CH 2 CO O—; —(CH 2 ) y COO—; and, —(CH 2 CH 2 O) z CH 2 COO—, where y is independently selected from 2,3,4 and 6-24 and z is independently selected from 2-24;   Y is independently at each occurrence selected from: —COCH 2 O—; —COCH(CH 3 )O—; —COCH 2 OCH 2 CH 2 O—; —COCH 2 CH 2 CH 2 CH 2 CH 2  O—; —CO(CH 2 ) m O—; and, —COCH 2 O(CH 2 CH 2 O) n —, where m is selected from 2-4 and 6-24 and n is selected from 2-24;   R′ is selected from hydrogen, benzyl, and C 1-6  alkyl;   p and q are independently selected from 0, 1, 2, 3, and 4, provided that p+q total 2, 3, or 4;   a and b, are independently selected from 0, 1, 2, 3, and 4, provided that a+b total from 1, 2, 3, 4, 5, or 6;   R is independently selected from —O—(X) c —R′ and —O—(Y) c —R′;   c is independently selected from 0, 1, 2, 3, and 4;   alternatively, R is independently selected from H, ═O, O-glycosides, —(CH 2 ) 0-2 —OR a , —(CH 2 ) 0-2 —C 6 H 5 , —(CH 2 ) 0-2 —CHO, Cl, F, Br, I, —(CH 2 ) 0-2 —OC(O)—R a , —(CH 2 ) 0-2 —CO 2 —R a , —(C(CH 3 )) 0-2 —CO 2 —R a , —(CH 2 ) 1-2 —CO 2 —(CH 2 ) 1-2   13  CO 2 —R 2 , —(C(CH 3 )) 1-2 —CO 2 —(CH 2 ) 1-2 —CO 2 —R a , —(CH 2 ) 0-2 —CO—R a , —O(CH 2 ) 0-2 —C 6 H 5 , —O( 2 —CO 2 R 2 , —O(C(CH 3 )) 1-2 —CO 2 —R a , —O(CH 2 ) 1-2 —CO—R a , —(CH 2 ) 0-2 —NO 2 , —(CH 2 ) 0-2 —NR a R a , —(CH 2 ) 0-2 —NR a COR a , —(CH 2 ) 1-2 —NR a C(O)(CH 2 ) 1-2 OR a , —C 6 H 5 , —C 6 H 5 OR a , and —C 6 H 5 —CH═CHCO 2 R a ; and,   R a  is independently selected from H and C 1-6  alkyl.   
     
     
         2 . A compound according to  claim 1 , wherein
 X is independently at each occurrence selected from: —CH 2 COO—; —CH(CH 3 )COO—; —CH 2 CH 2 OCH 2 COO—; and, —CH 2 CH 2 CH 2 CH 2 CH 2 COO—;   Y is independently at each occurrence selected from: —COCH 2 O—; —COCH(CH 3 )O—; —COCH 2 OCH 2  CH 2 O—; —COCH 2 CH 2 CH 2 CH 2 CH 2 O—;   p and q are independently selected from 0, 1, 2, and 3, provided that p+q total 2 or 3;   a and b, are independently selected from 0, 1, 2, and 3, provided that a+b total from 1, 2, 3, or 4; and,   c is independently selected from 0, 1, 2, and 3.   
     
     
         3 . A compound according to  claim 2 , wherein
 X is independently at each occurrence selected from: —CH 2 COO— and —CH(CH 3 )COO—;   Y is independently at each occurrence selected from: —COCH 2 O— and —COCH(CH 3 )O—;   a and b, are independently selected from 0, 1, and 2, provided that a+b total from 1, 2, 3, or  4; and,      c is independently selected from 0, 1, and 2.   
     
     
         4 . A compound according to  claim 2 , wherein:
 Ar is an aromatic ring substituted with 1, 2, or 3 R groups and the aromatic ring consists of 1-6 phenyl rings.   
     
     
         5 . A compound according to  claim 2 , wherein:
 Ar is an aromatic ring substituted with 1, 2, or 3 R groups and the aromatic ring consists of 1-3 phenyl rings.   
     
     
         6 . A compound according to  claim 2 , wherein:
 Ar is selected from phenyl and naphthyl and is substituted with 1, 2, or 3 R.   
     
     
         7 . A compound according to  claim 1 , wherein the compound is of formula Ia-Ic: 
       
         
           
           
               
               
           
         
       
     
     
         8 . A compound according to  claim 1 , wherein the compound is of formula IIa-IIc: 
       
         
           
           
               
               
           
         
       
     
     
         9 . A compound according to  claim 1 , wherein the compound is of formula IIIa IIIc: 
       
         
           
           
               
               
           
         
       
     
     
         10 . A compound according to  claim 1 , wherein the compound is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         11 . A composition, comprising: at least two different compounds of  claim 2 . 
     
     
         12 . A solvent for a drug, comprising: at least one compound of  claim 2 . 
     
     
         13 . A cosmetic composition, comprising at least one compound of  claim 2  and a cosmetic ingredient. 
     
     
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