Patent EP-0106799-B1 (EP)
IPC: C07C49/245
Filed: 1983-10-03
Granted: 1986-03-19
Abstract: 1. A compound of formula I   see diagramm : EP0106799,P47,F3   wherein p is 1, 2 or 3, q is 0, 1 or 2, with the proviso that (p+q) =< 3, and wherein R is a group of formula II   see diagramm : EP0106799,P47,F4   and, when p is 2 or 3, the groups R are the same or, within the scope of the above definitions, different and are in the 2-, 4- or 6-positions, and n is an integer from 2 to 30, and k is 1 or 2, and Q is selected from the radicals : a) -COOR**4 or -CONR**4 R**5 , wherein R**4 is hydrogen ; straight chain or branched C1 -C20 alkyl which may be interrupted by 1 to 5 oxygen atoms and is unsubstituted or substituted by -OR**6 groups, wherein R**6 is C3 -C12 cycloalkyl, straight chain or branched C3 -C20 alkenyl, C6 -C10 aryl which is unsubstituted or substituted by one or two C1 -C4 alkyl groups, or is C7 -C13 aralkyl ; and R4 is additionally divalent straight chain or branched C2 -C20 -alkylene ; straight chain or branched C3 -C20 alkenyl ; C3 -C12 -cycloalkyl ; C6 -C10 aryl which is unsubstituted or substituted by a C1 -C4 alkyl group ; or is C7 -C13 aralkyl ; or is a 5- or 6-membered oxygen-containing heterocyclic ring which is unsubstituted or substituted by one or two straight chain or branched C1 -C4 alkyl groups ; or R4 is methyl which is unsubstituted or substituted by a 5- or 6-membered oxygen-containing heterocyclic ring which is unsubstituted or substituted by one or two C1 -C4 alkyl groups, with the proviso that, when k is 2, the two carbon atoms to which the -COOR**4 groups are attached are not adjacent ; and R**5 is hydrogen or straight chain or branched C1 -C20 alkyl ; or R**4 and R**5 , together with the nitrogen atom to which they are attached, form a 5- or 6- membered heterocyclic ring which is unsubstituted or substituted by one or two C1 -C4 alkyl groups ; b) -OX, wherein X has the same meaning as R**5 , or is -COR**7 , wherein R**7 is hydrogen, straight chain or branched C1 -C20 -alkyl, straight chain or branched C3 -C20 alkenyl, C3 -C12 -cycloalkyl, C7 -C13 aralkyl, or is C6 -C10 aryl which may be unsubstituted or substituted by one or two C1 -C4 alkyl groups ; c) -NR**8 R**9 , wherein R**8 is hydrogen or straight chain or branched C1 -C4 alkyl, and R**9 is hydrogen, straight chain or branched C1 -C4 alkyl, or is -COR**7 , wherein R**7 is as defined above, or R**8 and R**9 , together with the nitrogen atom to which they are attached, form a 5- or 6-membered ring which is unsubstituted or substituted by one or two C1 -C4 alkyl groups ; d) -PO(OR**10 )[O]x -R**11 , wherein x is 0 or 1, and, when x is 1, R**10 and R**11 are the same or different and are each independently hydrogen or straight chain or branched C1 -C20 alkyl, or R**10 and R**11 are linked together to form a C2 -C3 alkylene chain which may be unsubstituted or substituted by one or more C1 -C20 alkyl groups, or, when x is 0, R**10 is hydrogen or straight chain or branched C1 -C20 alkyl, and R**11 is straight chain C1 -C5 alkyl ; e) -CN, halogen or -NO2 ; or f) -COR**12 , wherein R**12 is hydrogen, straight chain or branched C1 -C20 alkyl or halogen ; and R**2 and R**3 in formula II are the same or, within the scope of the above definitions, different and are straight chain or branched C1 -C5 alkyl, or R**2 or R**3 may be substituted by a -COOR**4 group, but only if Q is -COOR**4 , the radicals R**4 being independent of one another, or R**2 or R**3 is so linked to the radical Cn H2n+1-k as to form a C5 -C12 cycloalkylene radical which is substituted by -(CO2 R**4 )k groups, the radicals R**4 being independent of one another and R**4 and k being as defined above, or R**2 or R**3 is so linked to the radical -Cn H2n+1-k as to form, when Q is COR**12 , a C5 -C12 -cycloalkylene radical which may be substituted by a -COR**12 group, and, when Q is -COOR**4 and R**4 is C2 -C20 -alkylene, then p and k are 1, and the compound is of formula Ia   see diagramm : EP0106799,P48,F1   wherein R**40 is a divalent straight chain or branched C2 -C20 -alkylene chain ; and, when Q is -CONR**4 R**5 and R**4 is C2 -C20 alkylene, then p and k are 1, and the compound is of formula Ib   see diagramm : EP0106799,P48,F2   wherein R**41 is a straight chain or branched C2 -C20 alkylene chain ; and in which formulae, reverting to formula I, R**1 is straight chain or branched C1 -C12 alkyl, C7 -C9 aralkyl, halogen, CF3 , SH, SR**13 , COOH, COOR**13 , COR**13 , COC6 H5 , CONH2 , CN, SO3 H, SO2 NH2 , PO(OH)2 , PO(OR**13 ) or NO2 , with R**13 being C1 -C4 alkyl, and, when q is 2, the groups R**1 may be the same or, within the scope of the above definitions, different, and, when q is 1, the group R**1 may additionally be a radical of formula III or IV   see diagramm : EP0106799,P49,F1     see diagramm : EP0106799,P49,F2   wherein R and R**1 are as defined above, r is 0, 1 or 2, s is 0 or 1, with the proviso that (r+s) =< 2, and wherein M is a direct bond, -(R**14 )C(R**15 )-, -S-, -S-S- -SO-, -SO2 -, -CH2 SCH2 -, -O-, -CH2 OCH2 - or -NR**16 -, wherein each of R**14 and R**15 independently of the other may be hydrogen or straight chain or branched C1 -C20 alkyl which may be interrupted by 1 to 3 sulfur atoms, or may be C6 -C10 aryl, or R**14 and R**15 , together with the carbon atom to which they are attached, form a 5- or 6-membered ring which may be unsubstituted or substituted by one or two C1 -C8 alkyl groups, and R**16 is hydrogen, straight chain or branched C1 -C20 alkyl, or is phenyl ; with the proviso that the compound of formula I contains only one radical of the formula III or IV, and that this radical is in the 2-, 4- or 6-position relative to the hydroxyl group of formula I, and, when p is 1, R**1 is C1 -C12 alkyl, R**2 and R**3 are C1 -C5 alkyl, k is 1, Q is -COOR**4 and R**4 is hydrogen, and n is not 2 ; or a salt of a compound of formula I with an organic or inorganic acid or base.