Patent EP-0322251-A3 (EP)
Title: Benzothiopyran derivatives
IPC: C07D335/06
Filed: 1988-12-23
Abstract: A compound of formula (I): 
  
or, where appropriate, a pharmaceutically acceptable 
salt thereof, or a pharmaceutically acceptable solvate 
thereof  
wherein:  
A represents >C=X, wherein  
X represents oxygen or sulphur, or A represents a bond;   
 
Y represents N or N⁺-O⁻ or a moiety CR₈ wherein 
R₈ is as defined below;  
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;  
when A represents >C=X, then R₅ 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  
R₆ represents hydrogen or alkyl; 
or R₅ and R₆ together represent a linking chain of 
formula -A¹-A²-, A¹ being attached to the nitrogen atom 
of the moiety -N-A- and A² being attached to the group 
A on the said moiety, and wherein A¹ represents a 
substituted or unsubstituted methylene group, A² 
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 a 
bond, then R₅ and R₆ 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; 
R₇ and R₈ are each independently selected from the 
class of hydrogen, substituted or unsubstituted alkyl, 
alkoxy, C₃₋₈ cycloalkyl, hydroxy, nitro, cyano, halo, 
formyl, carboxy, a group of formula R a T¹-, R b R c NT-, 
R a T²NH-, R d CO.O-, R d CS.O-, R d  (OH)CH-, R d (SH)CH-, 
R d C(=N.OH)-, R d C(=N.NH₂)- or alkenyl optionally 
substituted by alkylcarbonyl, nitro or cyano, providing 
 
 
that when Y is CR₈ then at least one of R₇ or R₈ is not 
hydrogen;  
R a  represents R d  or R d O- and R d  represents substituted 
or unsubstituted alkyl, substituted or unsubstituted 
aryl or substituted or unsubstituted heteroaryl, 
optional substituents for R d  being up to 3 substituents 
selected from alkyl, alkoxy, halo, haloalkyl, nitro and 
cyano;  
R b  and R c  each independently represent hydrogen, alkyl 
or alkylcarbonyl;  
T represents a bond or T¹, T¹ represents -CS- or T² and 
T² represents -CO-, -SO- or -SO₂-; and  
p represents zero or an integer 2; a process for 
preparing such a compound, a pharmaceutical composition 
containing such a compound and the use of such a 
compound or composition in medicine.