Patent IE-893953-L (IE)
Title: Benzopyrans
IPC: C07D215/233
Filed: 1989-12-11
Abstract: A compound of formula (I): <CHEM> or, where appropriate, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof wherein: one of A1 or A2 represents hydrogen and the other represents a group CF3-Y- wherein Y represents -CF2-, >C=O, or -CH(OH)-; Y1 represents -O- -CH2- or NR<o> wherein R<o> is hydrogen, alkyl or alkylcarbonyl;R1 and R2 independently represent hydrogen or alkyl; or R1 and R2 together represent a C2-7 polymethylene moiety; R3 represents hydrogen, hydroxy, alkoxy or acyloxy and R4 is hydrogen or R3 and R4 together represent a bond; R5 represents either a moiety of formula (a): <CHEM> wherein A represents >C=X wherein X is O, S or NR8 wherein R8 represents CN, NO2, COR9 wherein R9 is alkyl, amino, monoalkylamino, fluoroalkyl, phenyl or substituted phenyl or R8 is SO2R9 wherein R9 is as defined above, or A represents a bond; when A represents >C=X wherein X is O or S, then R6 is hydrogen; alkyl optionally substituted by one or more groups or atoms selected from halogen, hydroxy, alkoxy, alkoxycarbonyl, carboxy or an ester or amide thereof, amino, monoalkylamino or dialkylamino; alkenyl; amino optionally substituted by an alkyl or alkenyl group or by an alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by alkyl, alkoxy or halogen; substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl; and R7 represents hydrogen or alkyl; or R6 and R7 together represent a linking chain of formula -A3-A4-, A3 being attached to the nitrogen atom of the moiety -N-A- and A4 being attached to the group A on the said moiety, and wherein A3 represents a substituted or unsubstituted methylene group, A4 represents 2 or 3 linking members, one of the linking members optionally representing O, S or NR and the other linking members each independently representing a substituted or unsubstituted methylene group; R represents hydrogen, alkyl, alkanoyl, phenyl C1-4- alkyl, arylcarbonyl wherein the aryl group may be substituted or unsubstituted; or R is mono- or bi-cyclic- heteroarylcarbonyl; when A represents >C=X wherein X represents NR8, then R6 represents -NH.R10 wherein R10 is hydrogen, alkyl, C3-6 cycloalkyl, alkenyl or alkynyl and R7 is hydrogen or alkyl; or R7 and R10 together represent C2-4 polymethylene; when A represents a bond, then R6 and R7 together with the nitrogen atom to which they are attached, form an unsaturated heterocyclic ring having 5 to 7 ring atoms, which ring atoms comprise up to 2 further nitrogen atoms and a carbon atom, the carbon atom being substituted with either an oxo group or a thioxo group, the remaining ring atoms being substituted or unsubstituted; or R5 represents a moiety of formula (b): <CHEM> wherein T1 represents >C-OH or N(O)n wherein n is zero or 1 and T2 together with C-T1, when T1 is >C-OH, represents an optionally substituted aryl group or T2 together with CT1, when T1 is N(O)n, represents an optionally substituted, N- heteroaryl group; or R5 represents a moiety of formula (c): <CHEM> wherein L1 represents O or NR11 wherein R11 represents hydrogen, alkyl, formyl, acetyl or hydroxymethyl, L2 represents N or CL4 wherein L4 is hydrogen, halogen, formyl or hydroxymethyl, L3 represents CH2, O, S, >CHL5 wherein L5 is halogen or NL6 wherein L6 is hydrogen or alkyl and R12 and R13 each independently represent hydrogen or alkyl or R12 together with R13 represents oxo or thioxo; and p represents 1,2 or 3; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of such a compcund and composition in medicine.
[EP0376524A1]