US2017291893A1PendingUtilityA1

Plasminogen activator inhibitor-1 inhibitors and methods of use thereof

Assignee: UNIV MICHIGAN REGENTSPriority: Oct 31, 2012Filed: Jun 27, 2017Published: Oct 12, 2017
Est. expiryOct 31, 2032(~6.3 yrs left)· nominal 20-yr term from priority
C07D 209/34C07D 207/48C07C 235/34C07C 235/80C07D 271/113C07C 311/48C07D 249/08C07C 243/26C07C 275/64C07C 311/37C07D 277/34C07C 237/20C07C 323/60C07D 209/08C07C 311/29C07C 69/94C07C 271/16C07D 417/10C07D 417/04C07D 261/18C07D 213/42C07C 311/49C07C 311/17C07C 259/06C07C 251/76C07C 235/46C07C 233/56C07C 69/84C07C 233/13
48
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Claims

Abstract

The invention relates to plasminogen activator- 1 (PAI- 1 ) inhibitor compounds and uses thereof in the treatment of any disease or disorder associated with elevated PAI- 1 . The invention includes, but is not limited to, the use of such compounds to prevent or reduce thrombosis and fibrosis, to promote thrombolysis, and to modulate lipid metabolism and treat diseases or disorders associated with elevated PAI- 1 , cholesterol, or lipid levels.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A compound of formula I or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is selected from the group consisting of C 1  to C 12  alkyl, -L 1 -C 3 -C 6  cycloalkyl, -L 2 -C 2 -C 6  heterocycloalkyl, benzyl, -L 3 -aryl, and -L 4 -heteroaryl; 
         R 2  is selected from the group consisting of -L 5 -C(═O)R 3 , -L 6 -R 4 , and NHR 5 ; 
         R 3  is selected from the group consisting of OR 6 , NR 7 R 8 , and NHNHR 9 ; 
         R 5  is selected from the group consisting of OR 10 , C 1  to C 12  alkyl, -L 7 -C 3 -C 6  cycloalkyl, -L 8 -C 2 -C 6  heterocycloalkyl, benzyl, -L 9 -aryl, and -L 10 -heteroaryl; 
         R 8  is selected from the group consisting of OR 11 , N═R 12 R 13 , -L 11 R 14 , NHSO 2 R 15 , and NHR 16 ; 
         R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 17  are independently selected from the group consisting of H and C 1  to C 12  alkyl; 
         R 4 , R 14 , R 15 , R 16  are independently selected from the group consisting of -L 12 -C 3 -C 6  cycloalkyl, -L 13 -C 2 -C 6  heterocycloalkyl, benzyl, -L 14 -aryl, and -L 15 -heteroaryl; and 
         L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , L 9 , L 10 , L 11 , L 12 , L 13 , L 14 , and L 15  are independently selected from the group consisting of null, C 1  to C 12  alkylene, and C 1  to C 12  alkenylene. 
       
     
     
         2 . The compound of  claim 1  having a formula selected from the group consisting of II, III, IV, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         3 . The compound of  claim 1  having a formula selected from the group consisting of V, VI, VII, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , wherein R 1  is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       pentyl, and butyl. 
     
     
         5 . The compound of  claim 1 , wherein R 4  is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 1 , wherein R 5  is OH. 
     
     
         7 . The compound of  claim 1 , wherein R 8  is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         8 . The compound of  claim 1  having a formula selected from the group consisting of C256, C259, C265, C267, C276, C277, C288, C309, C311, C280, C300, C313, C314, C320, C323, C326, C328, C334, C342, C240, C241, C246, C248, C251, C255, C260, C261, C262, C263, C264, C266, C268, C278, C281, C282, C287, C289, C295, C296, C297, C301, C304, C305, C307, C310, C322, C336, C339, C340, C341, C362, C279, C285, C286, C299, C306, C330, C344, C345, C346, C347, C348, C356, C357, C358, C359, C360, C361, C363, C364, C284, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . A compound of formula VIII or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         W is C or N; 
         X 1 , X 2 , X 3 , X 4 , and X 5  are independently selected from the group consisting of —H, —OH, —OR, —F, —Cl, —Br, —I, —NO 2 , —NO, —N(R) 2 , —N(R) 3   + , —C(O)R, —C(O)OR, —CHO, —C(O)NH 2 , —C(O)SR, —CN, —S(O) 2 R, —SO 3 R, —SO 3 H, —SO 2 N(R) 2 , —S═O, C 1  to C 12  alkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl; 
         R is selected from the group consisting of C 1  to C 6  alkyl, C 3  to C 6  cycloalkyl, CH 2 —C 3 -C 6  cycloalkyl, phenyl, tolyl, and benzyl; 
         R a  is selected from the group consisting of C 1  to C 12  alkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6  heterocycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6  heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof; and 
         m is 1, 2, 3, 4, 5, or 6; 
         with the proviso that at most two of X 1 , X 2 , X 3 , X 4 , and X 5  are OH; and excluding a compound of formula 
       
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 9 , wherein at most three of X 1 , X 2 , X 3 , X 4 , and X 5  are H. 
     
     
         11 . The compound of  claim 9  having a formula selected from the group consisting of C152, C155, C173, C189, C191, C197, C224, C292, C293, C294, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         12 . A compound of formula IX or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein R a  is selected from the group consisting of aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof; and 
         m is 1, 2, 3, 4, 5, or 6. 
       
     
     
         13 . The compound of  claim 12 , wherein R a  is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein: W is C or N; and 
         R 1  and R 2  are independently selected from the group consisting of —H, —F, —Cl, —Br, —I, —CF 3 , C 1  to C 12  alkyl, and phenyl. 
       
     
     
         14 . The compound of  claim 12  having a formula selected from the group consisting of C153, C162, C163, C165, C188, C195, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         15 . A compound having a formula selected from the group consisting of C157, C158, C182, C183, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         16 . A compound of formula X or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R a  is C 1  to C 12  alkyl, 
         R b  is selected from the group consisting of C 1  to C 12  alkyl, aryl, heteroaryl, (CH 2 ) m —R, and 
       
       
         
           
           
               
               
           
         
       
       or
 R a  and R b  taken together with the N atom to which they are bonded form an optionally substituted 3-, 4-, 5-, 7-, or 8-membered heterocyclic ring; 
 m is 1, 2, 3, 4, 5, or 6; 
 n is 0, 1, 2, 3, 4, 5, or 6; 
 Y is selected from the group consisting of NH 2  and OH; and 
 R selected from the group consisting of 
 
       
         
           
           
               
               
           
         
       
       substituted phenyl and heteroaryl. 
     
     
         17 . The compound of  claim 16 , wherein R a  is selected from the group consisting of butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl. 
     
     
         18 . The compound of  claim 16 , wherein R b  is selected from the group consisting of butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, fluorophenyl, chlorophenyl, bromophenyl, iodophenyl, trifluoromethylphenyl, and dichlorohydroxyphenyl. 
     
     
         19 . The compound of  claim 16  having a formula selected from the group consisting of C170, C171, C172, C175, C177, C179, C180, C186, C193, C205, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         20 . A compound of formula XI or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R b  is selected from the group consisting of aryl, heteroaryl, (CH 2 ) m —R, and 
       
       
         
           
           
               
               
           
         
         m is 1, 2, 3, 4, 5, or 6; 
         n is 0, 1, 2, 3, 4, 5, or 6; 
         Y is selected from the group consisting of NH 2  and OH; and 
         R selected from the group consisting of 
       
       
         
           
           
               
               
           
         
       
       CO 2 H, phenyl, substituted phenyl and heteroaryl. 
     
     
         21 . The compound of  claim 20  having a formula selected from the group consisting of C160, C187, C190, C198, C232, C233, C249, C270, C271, C272, C273, C274, C275, C303, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         22 . A compound of formula XII or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R b  is selected from the group consisting of aryl, heteroaryl, (CH 2 ) m —R, and 
       
       
         
           
           
               
               
           
         
         m is 1, 2, 3, 4, 5, or 6; 
         n is 0, 1, 2, 3, 4, 5, or 6; 
         Y is selected from the group consisting of NH 2  and OH; and 
         R selected from the group consisting of 
       
       
         
           
           
               
               
           
         
       
       CO 2 H, phenyl, substituted phenyl and heteroaryl. 
     
     
         23 . The compound of  claim 22  having a formula selected from the group consisting of C210 and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         24 . A compound having a formula selected from the group consisting of C168, C176, C184, C185, C196, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         25 . A compound having a formula selected from the group consisting of C156, C161, C200, C204, C236, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         26 . A compound of formula XIII or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein 
         n is 0 or 1; 
         R a  and R b  are independently selected from the group consisting of C 1  to C 12  alkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6  heterocycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6  heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof; and 
         m is 1, 2, 3, 4, 5, or 6. 
       
     
     
         27 . The compound of  claim 26 , wherein R a  and R b  are independently selected from the group consisting of butyl, pentyl, cyclopropyl, phenyl, difluorophenyl, and hydroxyphenyl. 
     
     
         28 . The compound of  claim 26  having a formula selected from the group consisting of C201, C208, C213, C216, C220, C221, C222, C223, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         29 . A compound of formula XIV or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of phenyl and substituted biphenyl. 
       
     
     
         30 . The compound of  claim 29  having a formula selected from the group consisting of C199, C207, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         31 . A compound of formula XV or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         V is selected from the group consisting of (CH 2 ) n , C 3  to C 8  cycloalkyl, (CH 2 ) n —C 3 -C 8  cycloalkyl-(CH 2 ) p , aryl, (CH 2 ) n -aryl-(CH 2 ) p , heteroaryl, (CH 2 ) n -heteroaryl-(CH 2 ) p , 
       
       
         
           
           
               
               
           
         
       
       and substituted derivatives thereof;
 n and p are independently 0, 1, 2, 3, 4, 5, or 6; 
 X 1 , X 2 , X 3 , X 4 , X 5  and X 6  are independently selected from the group consisting of H, —OH, —OR, —F, —Cl, —Br, —I, —NO 2 , —NO, —N(R) 2 , —N(R) 3   + , —C(O)R, —C(O)OR, —CHO, —C(O)NH 2 , —C(O)SR, —CN, —S(O) 2 R, —SO 3 R, —SO 3 H, —SO 2 N(R) 2 , —S═O, C 1  to C 12  alkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl; 
 R is selected from the group consisting of C 1  to C 6  alkyl, C 3  to C 6  cycloalkyl, CH 2 —C 3 -C 6  cycloalkyl, phenyl, tolyl, and benzyl; 
 Y 1  is selected from the group consisting of O, NH, NR a , S, and CH 2 ; 
 Y 2  is selected from the group consisting of O, NH, NR b , S, and CH 2 ; 
 R a  and R b  are independently selected from the group consisting of C 1  to C 12  alkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6  heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof; 
 m is 1, 2, 3, 4, 5, or 6; and 
 Z 1 , Z 2 , Z 3 , and Z 4  are independently selected from the group consisting of C, P—OH, S, and S═O. 
 
     
     
         32 . The compound of  claim 31  having a formula XVI or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
       
     
     
         33 . The compound of  claim 31  having a formula selected from the group consisting of C225, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         34 . A compound of formula XVII or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         X 1 , X 2 , X 3 , X 4 , X 5  and X 6  are independently selected from the group consisting of H, —OH, —OR, —F, —Cl, —Br, —I, —NO 2 , —NO, —N(R) 2 , —N(R) 3   + , —C(O)R,—C(O)OR, —CHO, —C(O)NH 2 , —C(O)SR, —CN, —S(O) 2 R, —SO 3 R, —SO 3 H, —SO 2 N(R) 2 , —S═O, C 1  to C 12  alkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl; 
         R is selected from the group consisting of C 1  to C 6  alkyl, C 3  to C 6  cycloalkyl, CH 2 —C 3 -C 6  cycloalkyl, phenyl, tolyl, and benzyl; 
         R b  is selected from the group consisting of H, C 1  to C 12  alkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6 heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof; 
         m is 1, 2, 3, 4, 5, or 6; and 
         Z 4  is selected from the group consisting of C, P—OH, S, and S═O. 
       
     
     
         35 . The compound of  claim 34  having a formula XVIII or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
       
     
     
         36 . The compound of  claim 34 , wherein X 1  and X 2  are independently selected from the group consisting of —OH and —OR. 
     
     
         37 . The compound of  claim 34  having a formula selected from the group consisting of C227, C228, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         38 . A compound of formula XIX or a salt, ester, or prodrug thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         X 3 , X 4 , and X 6  are independently selected from the group consisting of —H, —OH, —OR, —F, —Cl, —Br, —I, —NO 2 , —NO, —N(R) 2 , —N(R) 3   + , —C(O)R, —C(O)OR, —CHO, —C(O)NH 2 , —C(O)SR, —CN, —S(O) 2 R, —SO 3 R, —SO 3 H, —SO 2 N(R) 2 , —S═O, aryl, substituted aryl, heteroaryl, and substituted heteroaryl; 
         R is selected from the group consisting of C 1  to C 6  alkyl, C 3  to C 6  cycloalkyl, CH 2 —C 3 -C 6  cycloalkyl, phenyl, tolyl, and benzyl; 
         Y 1  is selected from the group consisting of CHR a R b , OR a , NHR a , NR a R b , and SR a ; 
         R a  and R b  are independently selected from the group consisting of C 1  to C 12  alkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6  heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, —U, (CH 2 ) m —U, and substituted derivatives thereof, or R a  and R b  taken together with the N atom to which they are bonded form a 3- to 8-membered heterocyclic ring; 
         U is selected from the group consisting of —NR c R d , —NR c C(O)R e , —NR c C(O)OR e , —NR c C(O)NR f R e , —NR c C(O)SR e , —NR c P(O)(OH)R e , —NR c P(O)(OH)OR e , —NR c P(O)(OH)NR f R c , —NR c P(O)(OH)SR c , —NR c S(O)R c , —NR c S(O)OR c , —NR c S(O)NR f R e , —NR c S(O)SR e , —NR c S(O) 2 R e , —NR c S(O) 2 OR e , —NR c S(O) 2 NR f R e , —NR c S(O) 2 SR e , —OR f , —OC(O)R e , —OC(O)OR e , —OC(O)NR f R e , —OC(O)SR e , —OP(O)(OH)R c , —OP(O)(OH)OR c , —OP(O)(OH)NR d R c , —OP(O)(OH)SR c , —OS(O)R c , —OS(O)OR e , —OS(O)NR d R e , —OS(O)SR e , —OS(O) 2 R e , —OS(O)  2 OR e , —OS(O) 2 NR d R e , —OS(O) 2 SR, —C(O)OR c , —C(O)NR c R d , —C(O)SR c , and —C(O)R c ; 
         R c  and R d  are independently selected from the group consisting of H, C 1  to C 12  alkyl, C 1  to C 12  haloalkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6 heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof, or R c  and R d  taken together with the N atom to which they are bonded form a 3- to 8-membered heterocyclic ring; 
         R e , R f , and R g  are independently selected from the group consisting of H, C 1  to C 12  alkyl, C 1  to C 12  haloalkyl, C 3  to C 6  cycloalkyl, (CH 2 ) m —C 3 -C 6  cycloalkyl, C 2  to C 6  heterocycloalkyl, (CH 2 ) m —C 2 -C 6 heterocycloalkyl, benzyl, aryl, (CH 2 ) m -aryl, heteroaryl, (CH 2 ) m -heteroaryl, and substituted derivatives thereof; 
         m is 1, 2, 3, 4, 5, or 6; and 
         Z 1  and Z 4  are independently selected from the group consisting of C, P—OH, S, and S═O. 
       
     
     
         39 . The compound of  claim 38  having a formula selected from the group consisting of C229, and salts, esters, or prodrugs thereof: 
       
         
           
           
               
               
           
         
       
     
     
         40 . A composition comprising an isolated compound according to any one of Formulas I to XIX, C256, C259, C265, C267, C276, C277, C288, C309, C311, C280, C300, C313, C314, C320, C323, C326, C328, C334, C342, C240, C241, C246, C248, C251, C255, C260, C261, C262, C263, C264, C266, C268, C278, C281, C282, C287, C289, C295, C296, C297, C301, C304, C305, C307, C310, C322, C336, C339, C340, C341, C362, C279, C285, C286, C299, C306, C330, C344, C345, C346, C347, C348, C356, C357, C358, C359, C360, C361, C363, C364, C284, C152, C155, C173, C189, C191, C197, C224, C292, C293, C294, C153, C162, C163, C165, C188, C195, C157, C158, C182, C183, C170, C171, C172, C175, C177, C179, C180, C186, C193, C205, C160, C187, C190, C198, C232, C233, C249, C270, C271, C272, C273, C274, C275, C303, C210, C168, C176, C184, C185, C196, C156, C161, C200, C204, C236, C201, C208, C213, C216, C220, C221, C222, C223, C199, C207, C225, C227, C228, or C229, or a salt, ester, or prodrug thereof, wherein said compound is present in an amount effective to inhibit PAI- 1 . 
     
     
         41 . A composition comprising the compound according to any one of Formulas I to XIX, C256, C259, C265, C267, C276, C277, C288, C309, C311, C280, C300, C313, C314, C320, C323, C326, C328, C334, C342, C240, C241, C246, C248, C251, C255, C260, C261, C262, C263, C264, C266, C268, C278, C281, C282, C287, C289, C295, C296, C297, C301, C304, C305, C307, C310, C322, C336, C339, C340, C341, C362, C279, C285, C286, C299, C306, C330, C344, C345, C346, C347, C348, C356, C357, C358, C359, C360, C361, C363, C364, C284, C152, C155, C173, C189, C191, C197, C224, C292, C293, C294, C153, C162, C163, C165, C188, C195, C157, C158, C182, C183, C170, C171, C172, C175, C177, C179, C180, C186, C193, C205, C160, C187, C190, C198, C232, C233, C249, C270, C271, C272, C273, C274, C275, C303, C210, C168, C176, C184, C185, C196, C156, C161, C200, C204, C236, C201, C208, C213, C216, C220, C221, C222, C223, C199, C207, C225, C227, C228, or C229, or a salt, ester, or prodrug thereof and a pharmaceutically acceptable carrier. 
     
     
         42 . A method of treating or preventing a disease or disorder associated with an elevated level of PAI- 1  in a subject comprising administering an effective amount of a composition comprising the compound according to any one of Formulas I to XXIX, C256, C259, C265, C267, C276, C277, C288, C309, C311, C280, C300, C313, C314, C320, C323, C326, C328, C334, C342, C240, C241, C246, C248, C251, C255, C260, C261, C262, C263, C264, C266, C268, C278, C281, C282, C287, C289, C295, C296, C297, C301, C304, C305, C307, C310, C322, C336, C339, C340, C341, C362, C279, C285, C286, C299, C306, C330, C344, C345, C346, C347, C348, C356, C357, C358, C359, C360, C361, C363, C364, C284, C152, C155, C173, C189, C191, C197, C224, C292, C293, C294, C153, C162, C163, C165, C188, C195, C157, C158, C182, C183, C170, C171, C172, C175, C177, C179, C180, C186, C193, C205, C160, C187, C190, C198, C232, C233, C249, C270, C271, C272, C273, C274, C275, C303, C210, C168, C176, C184, C185, C196, C156, C161, C200, C204, C236, C201, C208, C213, C216, C220, C221, C222, C223, C199, C207, C225, C227, C228, or C229, or a salt, ester, or prodrug thereof and a pharmaceutically acceptable carrier to decrease the elevated level of PAI- 1  in the subject. 
     
     
         43 . The method of  claim 42 , wherein the disease or disorder is cancer, septicemia, obesity, insulin resistance, a disease or disorder associated with dysregulation of lipid metabolism, a disease or disorder associated with an elevated level of VLDL or LDL, high cholesterol, a proliferative disease or disorder, fibrosis and fibrotic disease, coagulation homeostasis, cerebrovascular disease, microvascular disease, hypertension, dementia, atherosclerosis, osteoporosis, osteopenia, arthritis, asthma, heart failure, arrhythmia, angina, hormone insufficiency, Alzheimer's disease, hypertension, inflammation, sepsis, fibrinolytic disorder, stroke, dementia, coronary heart disease, myocardial infarction, stable and unstable angina, vascular disease, peripheral arterial disease, acute vascular syndrome, thrombosis, prothrombosis, deep vein thrombosis, pulmonary embolism, cerebrovascular disease, microvascular disease, hypertension, diabetes, hyperglycemia, hyperinsulinemia, malignant lesions, premalignant lesions, gastrointestinal malignancies, liposarcoma, epithelial tumor, and psoriasis, an extracellular matrix accumulation disorder, neoangiogenesis, myelofibrosis, fibrinolytic impairment, polycystic ovary syndrome, bone loss induced by estrogen deficiency, angiogenesis, neoangiogenesis, myelofibrosis, or fibrinolytic impairment. 
     
     
         44 . The method of  claim 43 , wherein the disease or disorder involving thrombosis or prothrombosis is formation of atherosclerotic plaques, venous thrombosis, arterial thrombosis, myocardial ischemia, atrial fibrillation, deep vein thrombosis, a coagulation syndrome, pulmonary thrombosis, cerebral thrombosis, a thromboembolic complication of surgery, and peripheral arterial occlusion. 
     
     
         45 . The method of  claim 43 , wherein the disease or disorder is fibrosis. 
     
     
         46 . The method of  claim 43 , wherein the extracellular matrix accumulation disorder is renal fibrosis, chronic obstructive pulmonary disease, polycystic ovary syndrome, restenosis, renovascular disease, diabetic nephropathy, or organ transplant rejection. 
     
     
         47 . A method of modulating cholesterol, lipid clearance, and/or lipid uptake in a subject with an elevated level of PAI- 1  comprising administering an effective amount of a composition comprising the compound according to any one of Formulas Ito XXIX, C256, C259, C265, C267, C276, C277, C288, C309, C311, C280, C300, C313, C314, C320, C323, C326, C328, C334, C342, C240, C241, C246, C248, C251, C255, C260, C261, C262, C263, C264, C266, C268, C278, C281, C282, C287, C289, C295, C296, C297, C301, C304, C305, C307, C310, C322, C336, C339, C340, C341, C362, C279, C285, C286, C299, C306, C330, C344, C345, C346, C347, C348, C356, C357, C358, C359, C360, C361, C363, C364, C284, C152, C155, C173, C189, C191, C197, C224, C292, C293, C294, C153, C162, C163, C165, C188, C195, C157, C158, C182, C183, C170, C171, C172, C175, C177, C179, C180, C186, C193, C205, C160, C187, C190, C198, C232, C233, C249, C270, C271, C272, C273, C274, C275, C303, C210, C168, C176, C184, C185, C196, C156, C161, C200, C204, C236, C201, C208, C213, C216, C220, C221, C222, C223, C199, C207, C225, C227, C228, or C229, or a salt, ester, or prodrug thereof and a pharmaceutically acceptable carrier in an amount effective to decrease the elevated level of PAI and modulate cholesterol, lipid clearance, and/or lipid uptake in the subject. 
     
     
         48 . The method of  claim 47 , wherein the composition increases circulating high density lipoprotein (HDL) and/or decreases circulating very low density lipoprotein (VLDL) in the subject. 
     
     
         49 . The method of  claim 47 , wherein the composition inhibits apolipoprotein E (ApoE) or apolipoprotein A (ApoA) binding to VLDL-R. 
     
     
         50 . The method of  claim 47 , wherein the composition affects HDL or apolipoprotein E (ApoE) or apolipoprotein A (ApoA) binding to an ApoA receptor. 
     
     
         51 . The method of  claim 47 , wherein the composition decreases PAI- 1  binding to apolipoprotein E (ApoE). 
     
     
         52 . The method of  claim 47 , wherein the composition decreases PAI- 1  binding to apolipoprotein A (ApoA). 
     
     
         53 . The method of  claim 47 , wherein the composition decreases PAI- 1  binding to VLDL. 
     
     
         54 . The method of  claim 47 , wherein the composition binds to PAI- 1  in the presence of vitronectin. 
     
     
         55 . The method of  claim 47 , wherein the composition binds to PAI- 1  in the presence of urokinase type plasminogen activator (uPA). 
     
     
         56 . The method of any one of  claims 42 - 55  wherein the subject is human.

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