Dichloroaniline derivatives

C - Chemistry – Metallurgy – 07 – C

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167/179, 260/557

C07C 237/20 (2006.01) C07C 311/32 (2006.01) C07D 295/192 (2006.01)

Patent

CA 1296335

ABSTRACT DICHLOROANILINE DERIVATIVES The invention provides compounds of the general formula (I) Image ( I ) wherein X represents a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene chain and Y represents a bond, or a C1-4 alkylene, C2-4 alkenylene or C2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8; Ar represents a phenyl group substituted by one or more substituents selected from nitro, -(CH2)qR [where R is C1-3 alkoxy, -NR3R4 (where R3 and R4 each represent 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 or -NR3R4 group), and q represents an integer from 1 to 3], -(CH2)rR7 [where R7 represents -NR5SO2R8 (where R8 epresents a C1-4 alkyl, phenyl or -NR3R4 group) -NR5COCH2N(R5)2 (where each of the groups R5 represents a hydrogen atom or a C1-4 alkyl group), -COR9 (where R represents hydroxy, C1-4 alkoxy or NR3R4), -SR10 (where R10 is a hydrogen atom, or a C1-4 alkyl group optionally substituted by hydroxy, C1-4 alkoxy or NR3R4), -SOR10, -SO2R10, -CN or -NR11R12 (where R11 and R12 represent a hydrogen atom or a C1-4 alkyl group, at least one of which is C2-4 alkyl substituted by a hydroxy, C1-4 alkoxy or NR3R4 group), and r represents an integer from 0 to 3], -O(CH2)qCOR9 (where q and R9 are as defined above), or -O(CH2)tR13 [where R13 represents hydroxy, NR3R4, NR11R12 or a C1-4alkoxy group optionally substituted by hydroxy, C1-4 alkoxy or NR3R4, and t is an integer 2 or 3]. R1 and R2 each represents 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; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds have a stimulant action at .beta.2-adreno-receptors and may be used in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

520447

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