Patent EP-0070097-A1 (EP)
Inventor: BAYS DAVID EDMUND
IPC: C07D249/14
Filed: 1982-06-11
Abstract: This invention relates to compounds of the general formula (I)
     and physiologically acceptable salts, hydrates and bioprecursors thereof in which 
     R 1  represents C 1-14  alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heteroaralkyl, trifluoroalkyl or alkyl substituted by hydroxy, alkoxy, amino, alkylamino, dialkylamino or cycloalkyl; and R 2  represents hydrogen or C 1-4  alkyl; or R 1  and R 2  may together with the nitrogen atom to which they are attached form a 5 to 10 membered ring which may be saturated or may contain at least one double bond, may be unsubstituted or may be substituted by one or more C 1-3  alkyl groups or a hydroxy group and/or may contain another heteroatom which is oxygen or sulphur; 
     Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; 
     Q represents a furan or tiophen ring in which incorporation into the rest of the molecule is through bonds at the 2-and 5-positions, the furan or thiophen optionally bearing a further substituent R 6  adjacent to the group R 1 R 2 N-Alk; or Q represents a tiophen ring in which incorporation into the rest of the molecule is through bonds at the 2- and 4- positions, the tiophen ring optionally bearing a further substituent R 6  adjacent to the group R 1 R 2 N-Alk with the proviso that when the group R 1 R 2 NAlk is in the 4-position then the group R 6  is in the 5-position; or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions;
     R 6  represents halogen or C 1-4  alkyl which may be substituted by hydroxy or C 1-4  alkoxy;   X represents oxygen, sulphur, -NH-, methylene or a bond;   n represents zero, 1 or 2; and m represents an integer from 2 to 5; with the proviso that when X represents -NH- then Q is a benzene ring;   R 3  represents hydrogen, alkyl, alkenyl, aralkyl, or C 2-6  alkyl substituted by hydroxy or alkoxy;   Alk" represents a straight or branched alkylene chain containing from 1 to 6 carbon atoms;   R 4  represents the group -ZCOR s  where R 5  represents hydroxy or alkoxy or the group
     in which the symbols R 1 ', R 2 ', Alk', Q', n', X', n' and R 3 ' have meanings which are as defined above for the symbols R 1 , R 2 , Alk, Q, n, X, m and R 3  respectively but which, in each case, may be the same as or different to the meaning of the latter symbol;   
     Alk b  represents a straight or branched alkylene chain containing from 1 to 6 carbon atoms; 
     Z represents an alkylene chain containing from 1 to 16 carbon atoms optionally substituted by one or two C 1-3  alkyl groups and optionally containing a double or triple bond; or optionally interrupted by a heteroatom, or by a disulphide (S-S) group; or optionally interrupted by a cycloalkyl or a phenyl group, or Z represents a cycloalkyl or a phenyl group; or 
     R 4  represents a C 1-6  straight or branched hydroxyalkyl group (optionally substituted by hydroxy or amino) or an aminoalkyl group (optionally substituted by amino, SH, C0 2 H or aryl). 
     The compounds show pharmacological activity as selective histamine H2-antagonists.