Novel aromatic nitro compounds

Abstract

Pharmaceutical compositions comprising at least one compound of e.g. the formulas (Ie) and a pharmaceutically acceptable carrier which is useful in a medicine wherein the symbols and substituents have the following meaning—X— is e.g. and Y is e.g. or the pharmaceutically acceptable salts, esters or amides and prodrugs of the above identified compounds can be applied to modulate the in-vitro and in-vivo binding processes mediated by E-, P- or L-selectin binding.

1 - 12 . (canceled) 
     
     
         13 . A chemical compound of the formula (Ib) or (Ic) or (Ie) or (If): 
       
         
           
           
               
               
           
         
         wherein the symbols and substituents have the following meaning: 
       
       
         
           
           
               
               
           
         
         with m=0, 1; n=an integer from 1 to 3 
       
       
         
           
           
               
               
           
         
         in which s is 0 or 1, 
         R 2  is CO 2 H, CO 2 Alkyl, CO 2 Aryl, CO 2 NH 2 , CO 2 Aralkyl, SO 3 H, SO 2 NH 2 , PO(OH) 2 , 1-H-tetrazolyl-, CHO, COCH 3 , CH 2 OH, NH 2 , NHAlkyl, N(Alkyl)Alkyl′, OCH 3 , CH 2 OCH 3 , SH, F, Cl, Br, I, CH 3 , CH 2 CH 3 , CN, or CF 3 ; 
         R 3  independently from R 2  is H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, I, CN, or NO 2 ; 
         R 4  independently from R 2  and R 3  is H, CH 3 , CH 2 CH 3 , CF 3 , F, Cl, Br, I, CN, NO 2 , or R 2 ; 
         R 5  is H, NO 2 , CF 3 , F, Cl, Br, I, CN, CH 3 , OCH 3 , SH, or NH 2 ; 
         —W— is —(CH 2 —) v , cis-CH═CH— or trans-CH═CH—, and v is 0, 1, or 2; 
         in case that —W— is cis-CH═CH— or trans-CH═CH—, R 2  must not be NH 2  or SH; 
       
       
         
           
           
               
               
           
         
         in which t is 0, 1, or 2; 
       
       
         
           
           
               
               
           
         
         R 6  independently from R 2  is H, F, Cl, Me, tert-Bu, CN, or NH 2 ; 
       
       
         
           
           
               
               
           
         
         R 7  independently from R 2  is H, NO 2 , CF 3 , F, Cl, Br, I, CN, CH 3 , OCH 3 , SH, or NH 2 ; 
       
       
         
           
           
               
               
           
         
         in which K is NH, NMe, O, or S; 
       
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt, ester, or amide thereof and prodrugs of the above identified compounds of formula (Ib) or (Ic) or (Ie) or (If). 
     
     
         14 . The chemical compound of  claim 13  defined by formula (A2) or (A3) or (A5) or (A6) or (B2) or (B3) or (B5) or (B6) 
       
         
           
           
               
               
           
         
         wherein —X′— and —Y are as defined in  claim 13  and wherein —X″— is 
       
       
         
           
           
               
               
           
         
         and wherein —Y′ is 
       
       
         
           
           
               
               
           
         
         wherein all indices, symbols, and substituents are as defined in  claim 13 . 
       
     
     
         15 . The chemical compound of  claim 13  defined by formula (C2) or (C3) or (C5) or (C6): 
       
         
           
           
               
               
           
         
         wherein —X″— is 
       
       
         
           
           
               
               
           
         
         and wherein —Y′ is 
       
       
         
           
           
               
               
           
         
         wherein all indices, symbols, and substituents are as defined in  claim 13 . 
       
     
     
         16 . The chemical compound of  claim 13  defined by formula (D2) or (D3) or (D5) or (D6): 
       
         
           
           
               
               
           
         
         wherein —X″— is 
       
       
         
           
           
               
               
           
         
         and wherein —Y″ is 
       
       
         
           
           
               
               
           
         
         wherein R 9  is CO 2 H, CO 2 alkyl, CO 2 aryl, CO 2 NH 2 , CO 2 aralkyl, 1-H-tetrazolyl, CHO, COCH 3 , CH 2 OH, or CH 2 OCH 3 , 
         wherein all indices, symbols, and substituents are as defined in  claim 13 . 
       
     
     
         17 . A method of treating or preventing Chronic Obstructive Pulmonary Disease (COPD), acute lung injury (ALI), cardiopulmonary bypass, acute respiratory distress syndrome (ARDS), Crohn's disease, septic shock, sepsis, chronic inflammatory diseases such as psoriasis, atopic dermatitis, and rheumatoid arthritis, and reperfusion injury that occurs following heart attacks, strokes, atherosclerosis, and organ transplants, traumatic shock, multi-organ failure, autoimmune diseases like multiple sclerosis, percutaneous transluminal angioplasty, asthma and inflammatory bowel disease, comprising the administration of a therapeutic amount of at least one compound having the structure of formula (Ib) or (Ic) or (Ie) or (If) as defined in  claim 13 . 
     
     
         18 . A method of treating, diagnosing, or preventing inflammatory disorders, comprising the administration of a therapeutic amount of at least one compound having the structure of formula (Ib) or (Ic) or (Ie) or (If) as defined in  claim 13 . 
     
     
         19 . A cosmetic or dermatological composition, comprising at least one compound having the structure of formula (Ib) or (Ic) or (Ie) or (If) as defined in  claim 13 . 
     
     
         20 . A cosmetic composition comprising at least one compound of the formula (Ib) or (Ic) or (Ie) or (If) as defined in  claim 13  and at least one cosmetically tolerable component. 
     
     
         21 . A dermatological composition comprising at least one compound of formula (Ib) or (Ic) or (Ie) or (If) as defined in  claim 13  and at least one dermatologically tolerable component. 
     
     
         22 . A pharmaceutical composition comprising at least one chemical compound of  claim 13  and a pharmaceutically acceptable excipient. 
     
     
         23 . A pharmaceutical composition comprising at least one chemical compound of  claim 14  and a pharmaceutically acceptable excipient. 
     
     
         24 . A pharmaceutical composition comprising at least one chemical compound of  claim 15  and a pharmaceutically acceptable excipient. 
     
     
         25 . A pharmaceutical composition comprising at least one chemical compound of  claim 16  and a pharmaceutically acceptable excipient.