Aminophenol derivatives

Details Aminophenol derivatives Aminophenol derivatives

C - Chemistry, Metallurgy

07

D

167/179, 260/557

C07D 295/12 (2006.01) C07C 103/44 (1985.01) C07C 143/75 (1985.01)

Patent

CA 1253864

ABSTRACT AMINOPHENOL DERIVATIVES The invention provides compounds of the general formula (I) Image ( I ) wherein Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C1-6alkyl, C1-6alkoxy, nitro, -(CH2)qR, [where R is hydroxy, -NR3R4 (where R3 and R4 each represents a hydrogen atom, or a C1-4 alkyl group or -NR3R4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from -O- or -S- or a group -NH- or -N(CH3)-), -NR5COR6 (where R5 represents a hydrogen atom or a C1-4 alkyl group, and R6 represents a hydrogen atom or a C1-4 alkyl, C1-4 alkoxy, phenyl or -NR3R4 group), -NR5SO2R7 (where R7 represents a C1- 4 alkyl, phenyl or -NR3R4 group), -COR8 (where R8 represents hydroxy, C1-4 alkoxy or -NR3R4), -SR9 (where R9 is a hydrogen atom, or a C1-4 alkyl or phenyl group), -SOR9, -SO2R9, or -CN, and q represents an integer from 0 to 3], -(CH2)rR10, [where R10 is a C1-4 alkoxy group and r represents an integer from 1 to 3], or -O(CH2)tR11 [where R11 represents a hydroxy or C1- 4 alkoxy group and t is 2 or 3], of Ar is a phenyl group substituted by an alkylenedioxy group of formula -O(CH2)pO-, where p repre- sents 1 or 2; R1 and R2 each represent a hydrogen atom or a C1-3 alkyl group with the proviso that the sum total of carbon atoms in R1 and R2 is not more than 4; X represents a C1-7 alkylene, C2-7 alkenylene or C2-7 alkynylene chain; Y represents a bond, or a C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is 2 to 10; Q represents a group R12CO- R12NHCO- R12R13NSO2- or R14SO2, where R12 and R13 each represent a hydrogen atom or a C1-3 alkyl group, and R14 represents a C1-4 alkyl group; with the proviso that when X represents C1-7 alkylene, and Y represents a bond or C1-6 alkylene, then the group Ar does not represent an unsubstituted phenyl group or a phenyl group substituted by one or more substituents selected solely from halogen atoms or C1-6 alkyl or C1-6 alkoxy groups or an alkylenedioxy group -O(CH2)pO-; and physiologically acceptable salts and solvates thereof. The compounds have a selective stimulant action at .beta.2-adrenoreceptors and may be used, inter alia, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

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