US2009318551A1PendingUtilityA1

Uses of analogs of 3-o-acetyl-11-keto-beta-boswellic acid

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Assignee: GOKARAJU GANGA RAJUPriority: Jun 18, 2004Filed: Aug 28, 2009Published: Dec 24, 2009
Est. expiryJun 18, 2024(expired)· nominal 20-yr term from priority
Inventors:Ganga Raju GokarajuRama Raju GokarajuVenkata Subbaraju GottumukkalaTrimurtulu Golakoti
A61P 35/00A61P 29/00C07J 63/008
60
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Claims

Abstract

This invention relates to novel AKBA analogs of the formula I given below: Where in R 1 , R 2 , R 3 , R 4 and R 5 in each of the said analogs are: 1. R 1 ═OCHO, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 2. R 1 ═OCOCH 2 Cl, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 3. R 1 =5′-O-methylgalloyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 4. R 1 ═OCOCH 2 CH 2 COOH, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 5. R 1 =8′,9′-Dihydro-4′-hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 6. R 1 =4′-Hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 7. R 1 =3′,4′-Dimethoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ′O 8. R 1 =3′,4′-Dihydroxy-5′-methoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 9. R 1 ═OCOCH 2 NH(tert-BOC), R 2 ═H, R 3 ═COOCH 3 , R 4 & R 5 ═O 10. R 1 ═OCOCH 2 NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 11. R 1 ═OCOCH(CH 3 )NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4 & R 5 ═O 12. R 1 ═H, R 2 ═OH, R 3 ═COOCH 3 , R 4 & R 5 ═O 13. R 1 ═H, R 2 ═Br, R 3 ═COOCH 3 , R 4 & R 5 ═O 14. R 1 ═CN, R 2 ═H, R 3 ═COOCH 3 , R 4 & R 5 ═O 15. R 1 ═SH, R 2 ═H, R 3 ═COOCH 3 , R 4 & R 5 ═O 16. R 1 & R 2 ═N(OH), R 3 ═COOCH 3 , R 4 & R 5 ═O 17. R 1 & R 2 ═H & OCOCH 3 R 3 ═H, R 4 & R 5 ═O 18. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═COOCH 2 CH 2 N(CH 3 ) 2 , R 4 & R 5 ═O 19. R 1 ═OCOCH 3 , R 2 ═H R 3 ═CONH 2 , R 4 & R 5 ═O 20. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHNH 2 , R 4 & R 5 50 O 21. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 NH 2 , R 4 & R 5 ═O 22. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 OH, R 4 & R 5 ═O 23. R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CON(CH 2 CH 2 ) 2 NH, R 4 & R 5 ═O 24. R 1 ═OCOCH 3 , R 2 ═H R 3 ═NCO, R 4 & R 5 ═O 25. R 1 ═OCOCH 3 , R 2 ═H R 3 ═NH 2 , R 4 & R 5 ═O 26. R 1 ═OCOCH 3 , R 2 ═H R 3 ═CN, R 4 & R 5 ═O 27. R 1 ═OH, R 2 ═H R 3 ═COOH, R 4 & R 5 ═OH & H These compounds exhibited 5-Lipoxigenase inhibitory properties and these compounds may be used in pharmaceutical compositions for therapeutic applications against a variety of inflammations and hypersensitivity-based human diseases including asthma, arthritis, bowel diseases such as ulcerative colitis and circulatory disorders such as shock and ischaemia. These compounds also inhibited the growth of Brine Shrimp in cultures, which may be considered as a positive indication for cytotoxicity and antitumor activity.

Claims

exact text as granted — not AI-modified
1 - 34 . (canceled) 
   
   
       35 . Use of boswellic acid analogs represented by the formula I 
     
       
         
         
             
             
         
       
       wherein R 1 , R 2 , R 3 , R 4  and R 5  are: 
       R 1 ═OCOCH 2 Cl, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =5′-O-methylgalloyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═OCOCH 2 CH 2 COOH, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =8′,9′-Dihydro-4′-hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =4′-Hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =3′,4′-Dimethoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =3′,4′-Dihydroxy-5′-methoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═OCOCH 2 NH(tert-BOC), R 2 ═H, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 2 NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═OCOCH(CH 3 )NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═H, R 2 ═BR, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1 ═CN, R 2 ═H, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1 ═SH, R 2 ═H, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1  and R 2 ═N(OH), R 3 ═COOCH 3 , R 4  and R 4 ═O; 
       R 1  and R 2 ═OCOCH 3 , R 3 ═H, R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═COOCH 2 CH 2 N(CH 3 ) 2 , R4 and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONH 2 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHNH 2 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 NH 2 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 OH, R 4  and R 4 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R3═CON(CH 2 CH 2 ) 2 NH, R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═NCO, R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═NH 2 , R 4  and R 5 ═O; or 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CN, R 4  and R 5 ═O; 
     
     as anti-inflammatory and antitumor agents. 
   
   
       36 . A method treating of inflammatory and tumor diseases comprising the step of administering boswellic acid analogs of the general formula I 
     
       
         
         
             
             
         
       
       wherein R 1 , R 2 , R 3 , R 4  and R 5 are: 
       R 1 ═OCOCH 2 Cl, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =5′-O-methylgalloyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═OCOCH 2 CH 2 COOH, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =8′,9′-Dihydro-4′-hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =4′-Hydroxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =3′,4′-Dimethoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 =3′,4′-Dihydroxy-5′-methoxycinnamoyloxy, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═OCOCH 2 NH(tert-BOC), R 2 ═H, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 2 NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═OCOCH(CH 3 )NH 2 HCl, R 2 ═H, R 3 ═COOH, R 4  and R 5 ═O; 
       R 1 ═H, R 2 ═Br, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1 ═CN, R 2 ═H, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1 ═SH, R 2 ═H, R 3 ═COOCH 3 , R 4  and R 5 ═O; 
       R 1  and R 2 ═N(OH), R 3 ═COOCH 3 , R 4  and R 4 ═O; 
       R 1  and R 2 ═OCOCH 3 , R 3 ═H, R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═COOCH 2 CH 2 N(CH 3 ) 2 , R4 and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONH 2 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHNH 2 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 NH 2 , R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CONHCH 2 CH 2 OH, R 4  and R 4 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R3═CON(CH 2 CH 2 ) 2 NH, R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═NCO, R 4  and R 5 ═O; 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═NH 2 , R 4  and R 5 ═O; or 
       R 1 ═OCOCH 3 , R 2 ═H, R 3 ═CN, R 4  and R 5 ═O; 
     
     to persons in need thereof.

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