Patent EP-0322251-A2 (EP)
Inventor: SMITH DAVID GLYNN BEECHAM PHAR
IPC: A61K31/40
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.